NCBI Taxonomy: 41503

Cynaropicrin

C19H22O6 (346.1416312)

Constituent of Cynara scolymus (artichoke). Cynaropicrin is found in cardoon, globe artichoke, and root vegetables. Cynaropicrin is found in cardoon. Cynaropicrin is a constituent of Cynara scolymus (artichoke). Cynaropicrin is a sesquiterpene lactone. Cynaropicrin is a natural product found in Pleiotaxis rugosa, Pseudostifftia kingii, and other organisms with data available. See also: Cynara scolymus leaf (part of). D009676 - Noxae > D003603 - Cytotoxins Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling. Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

Naringenin

C15H12O5 (272.0684702)

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs. Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4, 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7. Naringenin (not to be confused with naringin) is a flavanone that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater. This substance has also been shown to repair DNA. Scientists exposed cells to 80 micomoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24 percent in that very short period of time. Unfortunately, this bioflavonoid is difficult to absorb on oral ingestion. Only 15\\\\\\\% of ingested naringenin will get absorbed, in the human gastrointestinal tract, in the best case scenario. A full glass of orange juice will supply about enough naringenin to achieve a concentration of about 0.5 micromoles per liter. Naringenin is a biomarker for the consumption of citrus fruits. (S)-naringenin is the (S)-enantiomer of naringenin. It has a role as an expectorant and a plant metabolite. It is a naringenin and a (2S)-flavan-4-one. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin. Naringenin is a natural product found in Elaeodendron croceum, Garcinia multiflora, and other organisms with data available. See also: Naringin (related). Most widely distributed flavanone. Citrus fruits (grapefruit, oranges and pummelos) are especially good sources. Glycosides also widely distributed The (S)-enantiomer of naringenin. [Raw Data] CB070_Naringenin_pos_20eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_10eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_40eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_30eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_50eV_CB000030.txt [Raw Data] CB070_Naringenin_neg_10eV_000021.txt [Raw Data] CB070_Naringenin_neg_30eV_000021.txt [Raw Data] CB070_Naringenin_neg_50eV_000021.txt [Raw Data] CB070_Naringenin_neg_20eV_000021.txt [Raw Data] CB070_Naringenin_neg_40eV_000021.txt (±)-Naringenin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=67604-48-2 (retrieved 2024-07-09) (CAS RN: 67604-48-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Vanillic acid

C8H8O4 (168.0422568)

Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity (PMID: 16899266). Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072, 10543794, 11728709, 9579070). Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity. (PMID: 16899266). Vanillic acid is a monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a monohydroxybenzoic acid and a methoxybenzoic acid. It is a conjugate acid of a vanillate. Vanillic acid is a natural product found in Ficus septica, Haplophyllum cappadocicum, and other organisms with data available. Vanillic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. Vanillic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=121-34-6 (retrieved 2024-06-29) (CAS RN: 121-34-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

Protocatechuic acid

C7H6O4 (154.0266076)

Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

Luteolin

C15H10O6 (286.047736)

Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Genkwanin

C16H12O5 (284.0684702)

Genkwanin, also known as 5,4-dihydroxy-7-methoxyflavone or 7-methylapigenin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, genkwanin is considered to be a flavonoid lipid molecule. Genkwanin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Genkwanin is a bitter tasting compound and can be found in a number of food items such as winter savory, sweet basil, rosemary, and common sage, which makes genkwanin a potential biomarker for the consumption of these food products. Genkwanin is an O-methylated flavone, a type of flavonoid. It can be found in the seeds of Alnus glutinosa, and the leaves of the ferns Notholaena bryopoda and Asplenium normale . Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities. Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.

Ferulic acid

C10H10O4 (194.057906)

trans-Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. Ferulic acid is a phenolic acid that can be absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernel. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer disease (PMID:17127365, 1398220, 15453708, 9878519). Ferulic acid can be found in Pseudomonas and Saccharomyces (PMID:8395165). Ferulic acid is a ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. It has a role as an antioxidant, a MALDI matrix material, a plant metabolite, an anti-inflammatory agent, an apoptosis inhibitor and a cardioprotective agent. It is a conjugate acid of a ferulate. Ferulic acid is a natural product found in Haplophyllum griffithianum, Visnea mocanera, and other organisms with data available. Ferulic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Angelica sinensis root (part of). Widely distributed in plants, first isolated from Ferula foetida (asafoetida). Antioxidant used to inhibit oxidn. of fats, pastry products, etc. Antifungal agent used to prevent fruit spoilage. trans-Ferulic acid is found in many foods, some of which are deerberry, peach, shea tree, and common bean. A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D002491 - Central Nervous System Agents > D000700 - Analgesics D000975 - Antioxidants > D016166 - Free Radical Scavengers D006401 - Hematologic Agents > D000925 - Anticoagulants D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H074 (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

Syringin

C17H24O9 (372.14202539999997)

Syringin is a monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. It has a role as a hepatoprotective agent and a plant metabolite. It is a beta-D-glucoside, a monosaccharide derivative, a primary alcohol and a dimethoxybenzene. It is functionally related to a trans-sinapyl alcohol. Syringin is a natural product found in Salacia chinensis, Codonopsis lanceolata, and other organisms with data available. See also: Codonopsis pilosula root (part of). A monosaccharide derivative that is trans-sinapyl alcohol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2]. Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2].

Pinoresinol

C20H22O6 (358.1416312)

Epipinoresinol is an enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration. It has a role as a plant metabolite and a marine metabolite. Epipinoresinol is a natural product found in Pandanus utilis, Abeliophyllum distichum, and other organisms with data available. An enantiomer of pinoresinol having (+)-(1R,3aR,4S,6aR)-configuration. (+)-pinoresinol is an enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. It has a role as a hypoglycemic agent, a plant metabolite and a phytoestrogen. Pinoresinol is a natural product found in Pandanus utilis, Zanthoxylum beecheyanum, and other organisms with data available. See also: Acai fruit pulp (part of). An enantiomer of pinoresinol having (+)-1S,3aR,4S,6aR-configuration. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.907 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.905 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.897 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.895 Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Costunolide

C15H20O2 (232.14632200000003)

Costunolide is a germacranolide with anthelminthic, antiparasitic and antiviral activities. It has a role as an anthelminthic drug, an antiinfective agent, an antineoplastic agent, an antiparasitic agent, an antiviral drug and a metabolite. It is a germacranolide and a heterobicyclic compound. (+)-Costunolide is a natural product found in Magnolia garrettii, Critonia morifolia, and other organisms with data available. Constituent of costus root (Saussurea lappa). Costunolide is found in tarragon, sweet bay, and herbs and spices. Costunolide is found in herbs and spices. Costunolide is a constituent of costus root (Saussurea lappa) D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D000890 - Anti-Infective Agents > D000998 - Antiviral Agents INTERNAL_ID 2266; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2266 D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors Costunolide ((+)-Costunolide) is a naturally occurring sesquiterpene lactone, with antioxidative, anti-inflammatory, antiallergic, bone remodeling, neuroprotective, hair growth promoting, anticancer, and antidiabetic properties. Costunolide can induce cell cycle arrest and apoptosis on breast cancer cells[1][2][3]. Costunolide ((+)-Costunolide) is a naturally occurring sesquiterpene lactone, with antioxidative, anti-inflammatory, antiallergic, bone remodeling, neuroprotective, hair growth promoting, anticancer, and antidiabetic properties. Costunolide can induce cell cycle arrest and apoptosis on breast cancer cells[1][2][3].

Afzelin

C21H20O10 (432.105642)

Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. [Raw Data] CBA27_Afzelin_neg_30eV_1-1_01_1585.txt [Raw Data] CBA27_Afzelin_pos_20eV_1-1_01_1549.txt [Raw Data] CBA27_Afzelin_pos_10eV_1-1_01_1540.txt [Raw Data] CBA27_Afzelin_neg_10eV_1-1_01_1576.txt [Raw Data] CBA27_Afzelin_neg_20eV_1-1_01_1584.txt [Raw Data] CBA27_Afzelin_neg_40eV_1-1_01_1586.txt [Raw Data] CBA27_Afzelin_pos_30eV_1-1_01_1550.txt [Raw Data] CBA27_Afzelin_pos_50eV_1-1_01_1552.txt [Raw Data] CBA27_Afzelin_pos_40eV_1-1_01_1551.txt [Raw Data] CBA27_Afzelin_neg_50eV_1-1_01_1587.txt Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

Oleanolic acid

C30H48O3 (456.36032579999994)

Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

Stearic acid

C18H36O2 (284.2715156)

Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Matairesinol

C20H22O6 (358.1416312)

Matairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, matairesinol is found, on average, in the highest concentration in a few different foods such as sesame, burdocks, and flaxseeds, and in a lower concentration in oats, asparagus, and poppies. Matairesinol has also been detected, but not quantified in, several different foods, such as silver lindens, tamarinds, cherry tomato, skunk currants, and fireweeds. This could make matairesinol a potential biomarker for the consumption of these foods. Matairesinol is composed of gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). (-)-matairesinol is a lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). It has a role as a phytoestrogen, a plant metabolite, an angiogenesis inhibitor and an anti-asthmatic agent. It is a polyphenol, a lignan and a gamma-lactone. Matairesinol is a natural product found in Crossosoma bigelovii, Brassica oleracea var. sabauda, and other organisms with data available. See also: Arctium lappa fruit (part of); Pumpkin Seed (part of). Matairesinol is a plant lignan. It occurs with secoisolariciresinol in numerous foods such as oil seeds, whole grains, vegetables, and fruits. (-)-Matairesinol is found in many foods, some of which are caraway, pecan nut, cereals and cereal products, and longan. A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1]. Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1].

(-)-Arctigenin

C21H24O6 (372.1572804)

(-)-Arctigenin is found in burdock. (-)-Arctigenin is isolated from Cnicus benedictus, Forsythia viridissima, Arctium lappa, Ipomoea cairica and others (CCD).Arctigenin is a lignan found in certain plants of the Asteraceae , including the Greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral and anticancer effects. It is the aglycone of arctiin. (Wikipedia (-)-Arctigenin is a lignan. Arctigenin is a natural product found in Centaurea cineraria, Forsythia suspensa, and other organisms with data available. See also: Arctium lappa Root (part of); Arctium lappa fruit (part of); Pumpkin Seed (part of) ... View More ... Isolated from Cnicus benedictus, Forsythia viridissima, Arctium lappa, Ipomoea cairica and others (CCD) Arctigenin ((-)-Arctigenin), a biologically active lignan, can be used as an antitumor agent. Arctigenin exhibits potent antioxidant, anti-inflammatory and antiviral (influenza A virus) activities. Arctigenin can be used for the research of metabolic disorders, and central nervous system dysfunctions[1][2][3]. Arctigenin ((-)-Arctigenin), a biologically active lignan, can be used as an antitumor agent. Arctigenin exhibits potent antioxidant, anti-inflammatory and antiviral (influenza A virus) activities. Arctigenin can be used for the research of metabolic disorders, and central nervous system dysfunctions[1][2][3].

Scutellarein

C15H10O6 (286.047736)

Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

Onopordopicrin

C19H24O6 (348.1572804)

Heptanal

C7H14O (114.10445940000001)

Heptanal, also known as enanthal or N-heptaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, heptanal is considered to be a fatty aldehyde lipid molecule. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Heptanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptanal exists in all eukaryotes, ranging from yeast to humans. Heptanal is an aldehydic, citrus, and fat tasting compound. heptanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and sweet oranges and in a lower concentration in lemons, wild carrots, and carrots. heptanal has also been detected, but not quantified, in several different foods, such as horned melons, common beets, dills, red bell peppers, and malus (crab apple). This could make heptanal a potential biomarker for the consumption of these foods. The formation of heptanal in the fractional distillation of castor oil was already described in 1878. The large-scale production is based on the pyrolytic cleavage of ricinoleic acid ester (Arkema method) and on the hydroformylation of 1-hexene with rhodium 2-ethylhexanoate as a catalyst upon addition of some 2-ethylhexanoic acid (Oxea method):Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus). Heptanal is a potentially toxic compound. Heptanal has been found to be associated with several diseases such as ulcerative colitis, crohns disease, uremia, and nonalcoholic fatty liver disease; also heptanal has been linked to the inborn metabolic disorders including celiac disease. The compound has a flash point of 39.5 °C. The explosion range is between 1.1\\% by volume as the lower explosion limit (LEL) and 5.2\\% by volume as the upper explosion limit. Heptanal or heptanaldehyde is an alkyl aldehyde. Full hydrogenation provides the branched primary alcohol 2-pentylnonan-1-ol, also accessible from the Guerbet reaction from heptanol. A by-product of the given reaction is the unpleasant rancid smelling (Z)-2-pentyl-2-nonenal. Heptanal forms flammable vapor-air mixtures. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor, which is miscible with alcohols and practically insoluble in water. Heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90\\%) to alpha-pentylcinnamaldehyde (also called jasmine aldehyde because of the typical jasmine odor), which is mostly used in many fragrances as a cis/trans isomer mixture. Found in essential oils of ylang-ylang, clary sage, California orange, bitter orange and others. Flavouring agent

Artemisiifolin

C15H20O4 (264.13615200000004)

Zaluzanin C

C15H18O3 (246.1255878)

A sesquiterpene lactone that is decahydroazuleno[4,5-b]furan-2(3H)-one substituted by methylidene groups at positions 3, 6 and 9 and a hydroxy group at position 8.

fenchone

C10H16O (152.12010859999998)

A carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group. It is a component of essential oil from fennel (Foeniculum vulgare). Fenchone is a natural organic compound classified as a monoterpene and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery. Only 2 stereoisomers are possible: D-fenchone (enantiomer 1S,4R is dextrogyre (+)) and L-fenchone (enantiomer 1R,4S is levogyre (-)). Due to the small size of the cycle, the 2 other diastereoisomers (1S4S and 1R4R) are not possible. [Wikipedia]. Fenchone is found in many foods, some of which are ceylon cinnamon, sweet basil, saffron, and dill. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1]. (-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].

6-Hydroxyluteolin

C15H10O7 (302.042651)

Isolated from Valerianella eriocarpa (Italian corn salad). 6-Hydroxyluteolin is found in many foods, some of which are common thyme, mexican oregano, green vegetables, and lemon verbena. 6-Hydroxyluteolin is found in common thyme. 6-Hydroxyluteolin is isolated from Valerianella eriocarpa (Italian corn salad).

Sambunigrin

C14H17NO6 (295.1055822)

Isolated from leaves of elderberry (Sambucus nigra) and from other plants. Sambunigrin is found in passion fruit, fruits, and black elderberry. Sambunigrin is found in black elderberry. Sambunigrin is isolated from leaves of elderberry (Sambucus nigra) and from other plant

Genkwanin

C16H12O5 (284.0684702)

Genkwanin is a monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated. It has a role as a metabolite. It is a dihydroxyflavone and a monomethoxyflavone. It is functionally related to an apigenin. It is a conjugate acid of a genkwanin(1-). Genkwanin is a natural product found in Odontites viscosus, Eupatorium capillifolium, and other organisms with data available. A monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated. Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities. Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.

Vitexin

C21H20O10 (432.105642)

Vitexin is an apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet It has a role as a platelet aggregation inhibitor, an EC 3.2.1.20 (alpha-glucosidase) inhibitor, an antineoplastic agent and a plant metabolite. It is a C-glycosyl compound and a trihydroxyflavone. It is functionally related to an apigenin. It is a conjugate acid of a vitexin-7-olate. Vitexin is a natural product found in Itea chinensis, Salacia chinensis, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of); Cytisus scoparius flowering top (part of); Fenugreek seed (part of) ... View More ... An apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Pinoresinol

C20H22O6 (358.1416312)

4-[6-(4-Hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol is a natural product found in Zanthoxylum riedelianum, Forsythia suspensa, and other organisms with data available. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Naringenin

C15H12O5 (272.0684702)

Naringenin is a trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4. It is a trihydroxyflavanone and a member of 4-hydroxyflavanones. 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one is a natural product found in Prunus mume, Helichrysum cephaloideum, and other organisms with data available. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4. D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Vitexin

C21H20O10 (432.105642)

Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

3,4-Dihydrocadalene

C15H20 (200.15649200000001)

Constituent of hop, sweet flag, Juniperus and other oils. 3,4-Dihydrocadalene is found in many foods, some of which are root vegetables, rosemary, herbs and spices, and alcoholic beverages. 3,4-Dihydrocadalene is found in alcoholic beverages. 3,4-Dihydrocadalene is a constituent of hop, sweet flag, Juniperus and other oils.

Quercimeritrin

C21H20O12 (464.09547200000003)

Quercimeritrin, isolated from the leaves of Ixeridium dentatum, exhibits significant amylase activity[1]. Quercimeritrin, isolated from the leaves of Ixeridium dentatum, exhibits significant amylase activity[1].

Vicinin 2

C27H30O17 (626.148293)

Vicinin 2 is found in citrus. Vicinin 2 is a constituent of lemon (Citrus limon) peel and sugar cane syrup. Constituent of lemon (Citrus limon) peel and sugar cane syrup. Vicinin 2 is found in citrus.

Negletein

C16H12O5 (284.0684702)

Negletein is a neuroprotectant enhances the action of nerve growth factor and induces neurite outgrowth in PC12 cells. Negletein shows promising anti-inflammatory activity via inhibition of TNF-α and IL-1β with IC50 values of 16.4 and 10.8 μM, respectively[1]. Negletein is a neuroprotectant enhances the action of nerve growth factor and induces neurite outgrowth in PC12 cells. Negletein shows promising anti-inflammatory activity via inhibition of TNF-α and IL-1β with IC50 values of 16.4 and 10.8 μM, respectively[1].

1-Pentadecene

C15H30 (210.234738)

1-Pentadecene, also known as pentadec-1-ene, belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. 1-Pentadecene is an unbranched fifteen-carbon alkene with one double bond between C-1 and C-2. These compounds contain one or more double or triple bonds. Thus, 1-pentadecene is considered to be a hydrocarbon lipid molecule. 1-Pentadecene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Pentadecene is found, on average, in the highest concentration within safflowers. 1-Pentadecene has also been detected, but not quantified, in burdocks and watermelons. This could make 1-pentadecene a potential biomarker for the consumption of these foods. Occurs in beef and oakmoss oleoresin. 1-Pentadecene is found in many foods, some of which are animal foods, burdock, safflower, and watermelon.

Oroxylin A glucoronide

C22H20O11 (460.100557)

3h-Sucrose

C12H22O11 (342.11620619999997)

Sweetening agent and food source assimilated by most organismsand is also used in food products as a preservative, antioxidant, moisture control agent, stabiliser and thickening agent. Widespread in seeds, leaves, fruits, flowers and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynth. Annual world production is in excess of 90 x 106 tons mainly from the juice of sugar cane and sugar beet which contain respectively ca. 20\\% and ca. 17\\% of the sugar. Sucrose is found in many foods, some of which are rowanberry, brassicas, calabash, and hedge mustard.

Afzelin

C21H20O10 (432.105642)

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one can be found in a number of food items such as endive, linden, peach, and ginkgo nuts, which makes 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one a potential biomarker for the consumption of these food products. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

alpha-Amyrin

C30H50O (426.386145)

Epi-alpha-amyrin, also known as epi-α-amyrin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Epi-alpha-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Epi-alpha-amyrin can be found in herbs and spices, pomes, and rosemary, which makes epi-alpha-amyrin a potential biomarker for the consumption of these food products.

Epipinoresinol

C20H22O6 (358.1416312)

(+)-pinoresinol is a member of the class of compounds known as furanoid lignans. Furanoid lignans are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units (+)-pinoresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-pinoresinol can be found in a number of food items such as chanterelle, pecan nut, pine nut, and common hazelnut, which makes (+)-pinoresinol a potential biomarker for the consumption of these food products. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2]. Pinoresinol is a lignol of plant origin serving for defense in a caterpillar. Pinoresinol drastically sensitizes cancer cells against TNF-related apoptosis-inducing ligand (TRAIL) -induced apoptosis[1][2].

Vitexin

C21H20O10 (432.105642)

Vitexin is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin can be found in a number of food items such as flaxseed, prairie turnip, mung bean, and tree fern, which makes vitexin a potential biomarker for the consumption of these food products. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn . Isovitexin is a flavonoid isolated from passion flower, Cannabis and, and the palm, possesses anti-inflammatory and anti-oxidant activities; Isovitexin acts like a JNK1/2 inhibitor and inhibits the activation of NF-κB. Isovitexin is a flavonoid isolated from passion flower, Cannabis and, and the palm, possesses anti-inflammatory and anti-oxidant activities; Isovitexin acts like a JNK1/2 inhibitor and inhibits the activation of NF-κB. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Luteolin 7-(2'-apiosylglucoside)

C26H28O15 (580.1428138)

Luteolin 7-(2-apiosylglucoside) is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Luteolin 7-(2-apiosylglucoside) is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Luteolin 7-(2-apiosylglucoside) can be found in a number of food items such as parsley, italian sweet red pepper, celery leaves, and yellow bell pepper, which makes luteolin 7-(2-apiosylglucoside) a potential biomarker for the consumption of these food products.

1-Heptadecene

C17H34 (238.2660364)

1-heptadecene is a member of the class of compounds known as unsaturated aliphatic hydrocarbons. Unsaturated aliphatic hydrocarbons are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. These compounds contain one or more double or triple bonds. Thus, 1-heptadecene is considered to be a hydrocarbon lipid molecule. 1-heptadecene can be found in burdock and safflower, which makes 1-heptadecene a potential biomarker for the consumption of these food products.

Patuletin 7-glucoside

C22H22O13 (494.1060362)

Patuletin 7-glucoside is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Patuletin 7-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Patuletin 7-glucoside can be found in german camomile, which makes patuletin 7-glucoside a potential biomarker for the consumption of this food product.

Negletein

C16H12O5 (284.0684702)

Negletein is a member of flavonoids and an ether. Negletein is a natural product found in Stachys palustris, Desmos chinensis, and other organisms with data available. Negletein is a neuroprotectant enhances the action of nerve growth factor and induces neurite outgrowth in PC12 cells. Negletein shows promising anti-inflammatory activity via inhibition of TNF-α and IL-1β with IC50 values of 16.4 and 10.8 μM, respectively[1]. Negletein is a neuroprotectant enhances the action of nerve growth factor and induces neurite outgrowth in PC12 cells. Negletein shows promising anti-inflammatory activity via inhibition of TNF-α and IL-1β with IC50 values of 16.4 and 10.8 μM, respectively[1].

Scutellarein

C15H10O6 (286.047736)

Scutellarein is flavone substituted with hydroxy groups at C-4, -5, -6 and -7. It has a role as a metabolite. It is functionally related to an apigenin. It is a conjugate acid of a scutellarein(1-). Scutellarein is a natural product found in Scoparia dulcis, Artemisia douglasiana, and other organisms with data available. Flavone substituted with hydroxy groups at C-4, -5, -6 and -7. Scutellarein, also known as 6-hydroxyapigenin or 4,5,6,7-tetrahydroxyflavanone, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, scutellarein is considered to be a flavonoid lipid molecule. Scutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Scutellarein can be synthesized from apigenin. Scutellarein is also a parent compound for other transformation products, including but not limited to, scutellarin, 4,6-dihydroxy-5,7-dimethoxyflavone, and 6-hydroxy-4,5,7-trimethoxyflavone. Scutellarein is a bitter tasting compound found in mexican oregano and sweet orange, which makes scutellarein a potential biomarker for the consumption of these food products. Scutellarein is a flavone that can be found in Scutellaria lateriflora and other members of the genus Scutellaria, as well as the fern Asplenium belangeri . Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

Velutin

C17H14O6 (314.0790344)

Velutin is a dimethoxyflavone that is luteolin in which the hydroxy groups at positions 7 and 3 are replaced by methoxy groups. It has a role as an anti-inflammatory agent, a plant metabolite, a melanin synthesis inhibitor, an antibacterial agent, an antioxidant and an anti-allergic agent. It is a dimethoxyflavone and a dihydroxyflavone. It is functionally related to a 4,5,7-trihydroxy-3-methoxyflavone. Velutin is a natural product found in Avicennia officinalis, Lantana montevidensis, and other organisms with data available. See also: Acai (part of). A dimethoxyflavone that is luteolin in which the hydroxy groups at positions 7 and 3 are replaced by methoxy groups. [Raw Data] CB095_Velutin_neg_50eV_000026.txt [Raw Data] CB095_Velutin_neg_40eV_000026.txt [Raw Data] CB095_Velutin_neg_30eV_000026.txt [Raw Data] CB095_Velutin_neg_20eV_000026.txt [Raw Data] CB095_Velutin_neg_10eV_000026.txt [Raw Data] CB095_Velutin_pos_50eV_CB000040.txt [Raw Data] CB095_Velutin_pos_40eV_CB000040.txt [Raw Data] CB095_Velutin_pos_30eV_CB000040.txt [Raw Data] CB095_Velutin_pos_20eV_CB000040.txt [Raw Data] CB095_Velutin_pos_10eV_CB000040.txt Velutin is an aglycone extracted from Flammulina velutipes, with inhibitory activity against melanin biosynthesis. Velutin reduces osteoclast differentiation and down-regulates HIF-1α through the NF-κB pathway[1][2]. Velutin is an aglycone extracted from Flammulina velutipes, with inhibitory activity against melanin biosynthesis. Velutin reduces osteoclast differentiation and down-regulates HIF-1α through the NF-κB pathway[1][2]. Velutin is an aglycone extracted from Flammulina velutipes, with inhibitory activity against melanin biosynthesis. Velutin reduces osteoclast differentiation and down-regulates HIF-1α through the NF-κB pathway[1][2].

Quercimeritrin

C21H20O12 (464.09547200000003)

Quercetin 7-O-beta-D-glucoside is a quercetin O-glucoside in which a glucosyl residue is attached at position 7 of quercetin via a beta-glycosidic linkage. It has a role as an antioxidant and a metabolite. It is a beta-D-glucoside, a monosaccharide derivative, a member of flavonols, a tetrahydroxyflavone and a quercetin O-glucoside. Quercimeritrin is a natural product found in Salix atrocinerea, Dendroviguiera sphaerocephala, and other organisms with data available. See also: Chamomile (part of). Quercimeritrin, isolated from the leaves of Ixeridium dentatum, exhibits significant amylase activity[1]. Quercimeritrin, isolated from the leaves of Ixeridium dentatum, exhibits significant amylase activity[1].

Centaurein

C24H26O13 (522.1373346)

Patuletin 7-glucoside

C22H22O13 (494.1060362)

20-Hydroxyecdysone

C27H44O7 (480.3086874)

Afzelin

C21H20O10 (432.105642)

Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. Acquisition and generation of the data is financially supported in part by CREST/JST. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

Vitexin

C21H20O10 (432.105642)

Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Luteolin

C15H10O6 (286.047736)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.976 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.975 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.968 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.971 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Genkwanin

C16H12O5 (284.0684702)

Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities. Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.

Cynaropicrin

C19H22O6 (346.1416312)

Cynaropicrin is a sesquiterpene lactone. Cynaropicrin is a natural product found in Pleiotaxis rugosa, Pseudostifftia kingii, and other organisms with data available. See also: Cynara scolymus leaf (part of). D009676 - Noxae > D003603 - Cytotoxins Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling. Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

4-(3-Hydroxypropyl)-2,6-dimethoxyphenol

C11H16O4 (212.10485359999998)

heptadeca-1,8,11-triene

C17H30 (234.234738)

Oleanolic Acid

C30H48O3 (456.36032579999994)

Costunolide

C15H20O2 (232.14632200000003)

Costunolide is a germacranolide with anthelminthic, antiparasitic and antiviral activities. It has a role as an anthelminthic drug, an antiinfective agent, an antineoplastic agent, an antiparasitic agent, an antiviral drug and a metabolite. It is a germacranolide and a heterobicyclic compound. (+)-Costunolide is a natural product found in Magnolia garrettii, Critonia morifolia, and other organisms with data available. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics A germacranolide with anthelminthic, antiparasitic and antiviral activities. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors Costunolide ((+)-Costunolide) is a naturally occurring sesquiterpene lactone, with antioxidative, anti-inflammatory, antiallergic, bone remodeling, neuroprotective, hair growth promoting, anticancer, and antidiabetic properties. Costunolide can induce cell cycle arrest and apoptosis on breast cancer cells[1][2][3]. Costunolide ((+)-Costunolide) is a naturally occurring sesquiterpene lactone, with antioxidative, anti-inflammatory, antiallergic, bone remodeling, neuroprotective, hair growth promoting, anticancer, and antidiabetic properties. Costunolide can induce cell cycle arrest and apoptosis on breast cancer cells[1][2][3].

syringin

C17H24O9 (372.14202539999997)

Syringin, also known as eleutheroside b or beta-terpineol, is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Syringin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Syringin can be found in caraway, fennel, and lemon, which makes syringin a potential biomarker for the consumption of these food products. Syringin is a natural chemical compound first isolated from the bark of lilac (Syringa vulgaris) by Meillet in 1841. It has since been found to be distributed widely throughout many types of plants. It is also called eleutheroside B, and is found in Eleutherococcus senticosus (Siberian ginseng). It is also found in dandelion coffee . Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2]. Syringin is a main bioactive phenolic glycoside in Acanthopanax senticosus, with anti-osteoporosis activity. Syringin prevents cardiac hypertrophy induced by pressure overload through the attenuation of autophagy[1][2].

Matairesinol

C20H22O6 (358.1416312)

Annotation level-1 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 17 INTERNAL_ID 17; CONFIDENCE Reference Standard (Level 1) relative retention time with respect to 9-anthracene Carboxylic Acid is 0.920 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.921 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.910 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.909 Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1]. Matairesinol confers anti-allergic effects in an allergic dermatitis mouse model. DfE-induced changes in IL-4 and IFN-γ mRNA expression in the ears of NC/Nga mice were reversed by matairesinol application[1].

Ferulic acid

C10H10O4 (194.057906)

(E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

Vanillic Acid

C8H8O4 (168.0422568)

Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

stearic acid

C18H36O2 (284.2715156)

Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266076)

2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C12H22O11 (342.11620619999997)

Octadecanoic acid

C18H36O2 (284.2715156)

A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

Asahina

C15H12O5 (272.0684702)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Epi-a-amyrin

C30H50O (426.386145)

Vicinin 2

C27H30O17 (626.148293)

Heptanal

C7H14O (114.10445940000001)

1-PENTADECENE

C15H30 (210.234738)

An unbranched fifteen-carbon alkene with one double bond between C-1 and C-2.

3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

C20H22O6 (358.1416312)

Vanillate

C8H8O4 (168.0422568)

Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

Arctigenen

C21H24O6 (372.1572804)

Arctigenin ((-)-Arctigenin), a biologically active lignan, can be used as an antitumor agent. Arctigenin exhibits potent antioxidant, anti-inflammatory and antiviral (influenza A virus) activities. Arctigenin can be used for the research of metabolic disorders, and central nervous system dysfunctions[1][2][3]. Arctigenin ((-)-Arctigenin), a biologically active lignan, can be used as an antitumor agent. Arctigenin exhibits potent antioxidant, anti-inflammatory and antiviral (influenza A virus) activities. Arctigenin can be used for the research of metabolic disorders, and central nervous system dysfunctions[1][2][3].

linoleic

C18H32O2 (280.2402172)

Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].

Heptadecene

C17H34 (238.2660364)

(1S,2E,10R)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene

C15H24 (204.18779039999998)

3,4-Dihydrocadalene

C15H20 (200.15649200000001)

3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

C10H10O4 (194.057906)

(S)-Prunasin

C14H17NO6 (295.1055822)

(3ar,4s,6ar,8s,9r,9as,9bs)-8-(acetyloxy)-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl (2s)-2-methyloxirane-2-carboxylate

C21H24O8 (404.1471104)

tetradeca-4,6-dien-8,10,12-triyn-1-yl acetate

C16H16O2 (240.1150236)

(3ar,4s,6ar,8s,9r,9as,9bs)-8-(acetyloxy)-9-hydroxy-9-(hydroxymethyl)-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

C21H26O9 (422.15767460000006)

(3ar,4s,5ar,6r,9s,9as,9br)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-octahydro-3ah-naphtho[1,2-b]furan-4-yl (2e)-4-(acetyloxy)-2-(hydroxymethyl)but-2-enoate

C22H28O9 (436.17332380000005)

(3ar,4s,6ar,8s,9ar,9br)-4,8-dihydroxy-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

C15H18O4 (262.1205028)

hexadeca-7,14-dien-10,12-diyn-1-ol

C16H22O (230.1670562)

5,8-dihydroxy-3,6,9-trimethylidene-4-(2-methylpropoxy)-octahydroazuleno[4,5-b]furan-2-one

C19H26O5 (334.1780146)

deca-2,8-dien-4,6-diyne-1,10-diol

C10H10O2 (162.06807600000002)

hexadeca-6,8-dien-10,12,14-triynal

C16H16O (224.12010859999998)

(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,8,9-trihydroxy-3,6-dimethylidene-octahydroazuleno[4,5-b]furan-2-one

C15H19ClO5 (314.0920954)

(2e,6e)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene

C15H24 (204.18779039999998)

5,7-dihydroxy-2-phenyl-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

C21H20O9 (416.110727)

6-[(2-{4-[(6-{[(3-carboxypropanoyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]phenyl}-5-hydroxy-4-oxochromen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

C31H32O19 (708.1537722)

(3s,3as,11ar)-10-(hydroxymethyl)-3,6-dimethyl-3h,3ah,5h,8h,9h,11ah-cyclodeca[b]furan-2,4-dione

C15H20O4 (264.13615200000004)

(1r,2r,5s,6s,7r)-5-isopropyl-2-methyl-8-methylidene-11-oxatricyclo[5.3.1.0²,⁶]undecane

C15H24O (220.18270539999997)

8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-methyloxirane-2-carboxylate

C19H22O6 (346.1416312)

6-ethenyl-7-(3-hydroxyprop-1-en-2-yl)-5-methyl-3-methylidene-2-oxo-hexahydro-1-benzofuran-4-yl 3,4-dihydroxy-2-methylidenebutanoate

C20H26O7 (378.1678446)

5-(acetyloxy)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl acetate

C19H22O7 (362.1365462)

10-(hydroxymethyl)-3,6-dimethyl-3h,3ah,5h,8h,9h,11ah-cyclodeca[b]furan-2,4-dione

C15H20O4 (264.13615200000004)

10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylpropanoate

C19H26O6 (350.1729296)

pentadeca-5,7,13-trien-9,11-diyn-1-yl acetate

C17H20O2 (256.146322)

(3ar,4s,11ar)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2-methylprop-2-enoate

C19H24O5 (332.1623654)

(2e)-dec-2-en-4,6-diyne-1,10-diol

C10H12O2 (164.0837252)

2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C22H22O12 (478.1111212)

(3ar,4s,11ar)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (2z)-2-(hydroxymethyl)but-2-enoate

C20H26O6 (362.17292960000003)

1-(acetyloxy)pentadeca-5,7,13-trien-9,11-diyn-3-yl acetate

C19H22O4 (314.1518012)

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7,8-trimethoxychromen-4-one

C19H18O8 (374.1001628)

(3as,4r,5r,6ar,8s,9ar,9br)-5,8-dihydroxy-3,6,9-trimethylidene-4-(2-methylpropoxy)-octahydroazuleno[4,5-b]furan-2-one

C19H26O5 (334.1780146)

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12-(hydroxymethylidene)-17,21,26-trimethyl-4-oxo-22-(3-oxo-3-{[(2e,7s,11s)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,5(26),6,8,10,13(25),14,16,18(24),19-decaene-3-carboxylate

C55H72N4O6 (884.5451572)

tetradeca-4,6,12-trien-8,10-diyne-1,3-diol

C14H16O2 (216.1150236)

(3r,4r)-4-{[(2s,3r)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl}-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-methyloxolan-2-one

C31H34O9 (550.2202714)

(9e,11e,13e,15e)-octadeca-9,11,13,15-tetraenal

C18H28O (260.2140038)

(2s,3s,4r,5r,6s)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-{[(2s)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

C26H28O15 (580.1428138)

3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C22H22O12 (478.1111212)

tetradec-12-en-8,10-diyne-1,3,14-triol

C14H20O3 (236.14123700000002)

tetradec-8-en-11,13-diyn-2-one

C14H18O (202.1357578)

(4e,6e)-tetradeca-4,6-dien-8,10,12-triyn-1-ol

C14H14O (198.1044594)

β-cyclocostunolide

C15H20O2 (232.14632200000003)

(1s,2s,3r,4r,5s)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl (3s)-3,4-dihydroxy-2-methylidenebutanoate

C21H30O8 (410.194058)

(1s,2r,4r,7e,10s,11r)-4,8-dimethyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.0²,⁴]tetradec-7-en-10-yl (2e)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

C20H26O7 (378.1678446)

1,14-bis(acetyloxy)tetradeca-4,6,12-trien-8,10-diyn-3-yl acetate

C20H22O6 (358.1416312)

8-hydroxy-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate

C32H52O3 (484.3916242)

4-(hydroxymethyl)-6-isopropyl-8a-methyl-octahydronaphthalene-1,4,5-triol

C15H28O4 (272.19874880000003)

(2s,4ar,4br,6as,8r,10ar,10br,12ar)-1,1,4a,8,10a,10b-hexamethyl-8-(4-methyl-3-oxopentyl)-7-oxo-dodecahydrochrysen-2-yl acetate

C32H52O4 (500.3865392)

octadeca-9,16-dien-12,14-diynal

C18H24O (256.1827054)

9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-octahydro-3ah-naphtho[1,2-b]furan-4-yl 4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

C22H28O9 (436.17332380000005)

7-hydroxy-8a-methyl-3,5-dimethylidene-octahydronaphtho[2,3-b]furan-2-one

C15H20O3 (248.14123700000002)

(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2s)-2-methyloxirane-2-carboxylate

C19H23ClO7 (398.1132238)

2-chlorotrideca-3,11-dien-5,7,9-triyn-1-ol

C13H11ClO (218.0498386)

(3ar,4s,6ar,8s,9r,9as,9bs)-9-[(acetyloxy)methyl]-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-(hydroxymethyl)prop-2-enoate

C21H26O9 (422.15767460000006)

citronellol, (+-)-

C10H20O (156.151407)

(3as,4r,10s,11ar)-6-(hydroxymethyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,7h,8h,9h,10h,11h,11ah-cyclodeca[b]furan-4-yl (2e)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

C20H28O7 (380.1834938)

3-{[(2s,3s,4r,5r,6s)-4,5-dihydroxy-6-methyl-3-{[(2s,3s,4s,5r,6r)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

C27H30O15 (594.158463)

4-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

C15H22O4 (266.1518012)

8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 3-chloro-2-hydroxy-2-methylpropanoate

C19H23ClO6 (382.1183088)

pentadeca-5,7,11,13-tetraen-9-ynal

C15H18O (214.1357578)

(3r,3ar,4s,6ar,8s,9ar,9br)-4,8-dihydroxy-3-methyl-6,9-dimethylidene-octahydro-3h-azuleno[4,5-b]furan-2-one

C15H20O4 (264.13615200000004)

2-(tetradeca-5,12-dien-8,10-diyn-1-yl)octadeca-2,9,16-trien-12,14-diyn-1-ol

C32H40O (440.307899)

10-(acetyloxy)dec-2-en-4,6-diyn-1-yl acetate

C14H16O4 (248.10485359999998)

(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2r)-3-chloro-2-hydroxy-2-methylpropanoate

C19H24Cl2O7 (434.0899014)

(3r,4e,6e)-tetradeca-4,6-dien-8,10,12-triyne-1,3-diol

C14H14O2 (214.09937440000002)

(2s,3s,4s,5r,6s)-6-{[2-(4-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}phenyl)-5-hydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

C30H30O19 (694.138123)

1,14-bis(acetyloxy)tetradec-12-en-8,10-diyn-7-yl acetate

C20H26O6 (362.17292960000003)

8-hydroxy-4'-methyl-6,9-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-3,2'-oxetan]-4-yl 2-(hydroxymethyl)prop-2-enoate

C21H26O7 (390.1678446)

(2s,3e,5e)-2-hydroxytrideca-3,5-dien-7,9,11-triyn-1-yl acetate

C15H14O3 (242.0942894)

(3ar,4s,6ar,8s,9r,9as,9bs)-8-hydroxy-3,6-dimethylidene-2-oxo-octahydrospiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl (2s)-3-chloro-2-hydroxy-2-methylpropanoate

C19H23ClO7 (398.1132238)

methyl (3r,21s,22s)-16-ethenyl-11-ethyl-12-formyl-17,21,26-trimethyl-4-oxo-22-(3-oxo-3-{[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1(23),2(6),5(26),7,9,11,13,15,17,19-decaene-3-carboxylate

C55H72N4O6 (884.5451572)

1-chlorotridec-3-en-5,7,9,11-tetrayn-2-ol

C13H9ClO (216.03418939999997)

(2z)-n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidic acid

C20H20N2O4 (352.14230000000003)

(8z)-tetradec-8-en-11,13-diyn-2-one

C14H18O (202.1357578)

(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal

C18H16O6 (328.0946836)

(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-4,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl benzoate

C22H23ClO6 (418.1183088)

(3s,3as,5r,11as)-5-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

C15H22O4 (266.1518012)

(7ar)-1,1,7-trimethyl-4-methylidene-octahydrocyclopropa[e]azulen-7-ol

C15H24O (220.18270539999997)

(3ar,4s,6ar,8s,9ar,9br)-8-(acetyloxy)-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl 2-[(acetyloxy)methyl]prop-2-enoate

C23H26O8 (430.1627596)

2-(nona-4,6,8-trien-2-yn-1-ylidene)-5h-furan

C13H12O (184.08881019999998)

(1r,2s,6s,7s,8r)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene

C15H24 (204.18779039999998)

octadeca-8,10,14,16-tetraen-12-ynal

C18H24O (256.1827054)

3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-octahydroazuleno[4,5-b]furan-2-one

C15H20O5 (280.13106700000003)

(2r,3s,4s,5r,6s)-6-{4-[(1s,3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-5-{[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)oxane-3,4-diol

C31H40O15 (652.236709)

hexadeca-7,9,11,13-tetraen-1-yl 3-methylbutanoate

C21H34O2 (318.2558664)

(3ar,4s,6ar,8s,9ar,9br)-8-{[(2e)-4-hydroxy-2-methylbut-2-enoyl]oxy}-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-4-hydroxy-2-methylbut-2-enoate

C25H30O8 (458.194058)

(2z)-n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enimidic acid

C19H18N2O3 (322.1317358)

(7e,9e,11e,13e)-hexadeca-7,9,11,13-tetraen-1-yl 3-methylbutanoate

C21H34O2 (318.2558664)

(3ar,4s,11ar)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl (2z)-4-(acetyloxy)-2-methylbut-2-enoate

C22H28O7 (404.1834938)

pentadeca-5,7,13-trien-9,11-diyn-1-ol

C15H18O (214.1357578)

(3ar,4s,5ar,6r,9s,9as,9br)-4,6-dihydroxy-5a-methyl-3-methylidene-2-oxo-octahydro-3ah-naphtho[1,2-b]furan-9-carbaldehyde

C15H20O5 (280.13106700000003)

5-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6-{4-[4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-2-(hydroxymethyl)oxane-3,4-diol

C31H40O15 (652.236709)

2-hydroxytrideca-3,11-dien-5,7,9-triyn-1-yl acetate

C15H14O3 (242.0942894)

(3r,4e,6e,12e)-tetradeca-4,6,12-trien-8,10-diyne-1,3,14-triol

C14H16O3 (232.1099386)

2-(undec-9-en-1,3,5,7-tetrayn-1-yl)oxirane

C13H8O (180.0575118)

3-{[(2s,3r,4s,5s,6r)-6-{[(3-carboxypropanoyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

[C31H35O19]+ (711.177246)

2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-3-ol

C20H24O7 (376.1521954)

4-hydroxy-4'-methyl-6,9-dimethylidene-octahydrospiro[azuleno[4,5-b]furan-3,2'-oxetan]-2-one

C17H22O4 (290.1518012)

(3r,4e,6z)-tetradeca-4,6-dien-8,10,12-triyne-1,3-diol

C14H14O2 (214.09937440000002)

(3ar,4s,6ar,8s,9s,9as,9bs)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2e)-2-(hydroxymethyl)but-2-enoate

C20H25ClO7 (412.128873)

5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one

C21H20O11 (448.100557)

(3r,3ar,6ar,9s,9ar,9br)-3-(hydroxymethyl)-9-methyl-6-methylidene-2,8-dioxo-octahydroazuleno[4,5-b]furan-3-yl acetate

C17H22O6 (322.1416312)

(3r,5z,7e,13e)-1-(acetyloxy)pentadeca-5,7,13-trien-9,11-diyn-3-yl acetate

C19H22O4 (314.1518012)

(6e,8e,14e)-hexadeca-1,6,8,14-tetraen-10,12-diyne

C16H18 (210.1408428)

5,7-dihydroxy-2-(3-hydroxy-4-{[(2s,4r,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one

C21H20O11 (448.100557)

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

C21H18O11 (446.0849078)

methyl 2-[(1r,2r,3r,4s,6s)-4-ethenyl-2,6-dihydroxy-3-(3-hydroxyprop-1-en-2-yl)-4-methylcyclohexyl]prop-2-enoate

C16H24O5 (296.1623654)

(3s,3ar,4s,11ar)-4-hydroxy-10-(hydroxymethyl)-3,6-dimethyl-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-one

C15H22O4 (266.1518012)

7-isopropyl-1,2,10,15,19,19-hexamethyl-6-oxahexacyclo[12.8.0.0²,¹¹.0⁵,⁷.0⁵,¹⁰.0¹⁵,²⁰]docosan-18-ol

C30H50O2 (442.38106)

9-(chloromethyl)-4,8,9-trihydroxy-3,6-dimethylidene-octahydroazuleno[4,5-b]furan-2-one

C15H19ClO5 (314.0920954)

deca-2,8-dien-4,6-diyn-1-ol

C10H10O (146.073161)

(2s,3s,4r,4as,5s,8r,8ar)-5-formyl-4,8-dihydroxy-3-(3-methoxy-3-oxoprop-1-en-2-yl)-8a-methyl-octahydro-1h-naphthalen-2-yl (3s)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

C23H32O10 (468.1995372)

(2e)-n-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enimidic acid

C19H18N2O3 (322.1317358)

(3r,4e,6e,12e)-3-hydroxytetradeca-4,6,12-trien-8,10-diyn-1-yl acetate

C16H18O3 (258.1255878)

(3s,4e,6e,12e)-1-(acetyloxy)tetradeca-4,6,12-trien-8,10-diyn-3-yl acetate

C18H20O4 (300.13615200000004)

(3ar,4s,5ar,6r,9r,9as,9br)-4,6-dihydroxy-5a-methyl-3-methylidene-2-oxo-octahydro-3ah-naphtho[1,2-b]furan-9-carbaldehyde

C15H20O5 (280.13106700000003)

2-(but-3-en-1-yn-1-yl)-5-(penta-1,3-diyn-1-yl)thiophene

C13H8S (196.0346688)

(3ar,4s,5ar,6r,9s,9as,9br)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-octahydro-3ah-naphtho[1,2-b]furan-4-yl (3r)-4-(acetyloxy)-3-hydroxy-2-methylidenebutanoate

C22H28O9 (436.17332380000005)

tetradeca-6,12-dien-8,10-diyne-1,5,14-triol

C14H18O3 (234.1255878)

{7-hydroperoxy-4-hydroxy-3,6-dimethylidene-2-oxo-3ah,4h,5h,7h,8h,9h,11ah-cyclodeca[b]furan-10-yl}methyl acetate

C17H22O7 (338.1365462)

(3s,3ar,4s,6ar,8s,9ar,9br)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-octahydro-3h-azuleno[4,5-b]furan-4-yl (2s)-2-methyloxirane-2-carboxylate

C19H24O6 (348.1572804)

(3ar,4r,6ar,8s,9ar,9br)-4-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-8-yl acetate

C17H20O5 (304.13106700000003)

(3s,3ar,4s,5ar,6r,9s,9as,9br)-9-formyl-6-hydroxy-3,5a-dimethyl-2-oxo-decahydronaphtho[1,2-b]furan-4-yl 4-hydroxy-2-methylidenebutanoate

C20H28O7 (380.1834938)

tetradeca-5,12-dien-8,10-diyne-1,7,14-triol

C14H18O3 (234.1255878)

tetradeca-4,6-dien-8,10,12-triyne-1,3-diol

C14H14O2 (214.09937440000002)