NCBI Taxonomy: 128640

Lindera umbellata (ncbi_taxid: 128640)

found 104 associated metabolites at species taxonomy rank level.

Ancestor: Lindera

Child Taxonomies: Lindera umbellata var. umbellata, Lindera umbellata var. membranacea

Epicatechin

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C15H14O6 (290.079)


Epicatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechin is a tannin peculiar to green and white tea because the black tea oxidation process reduces catechins in black tea. Catechin is a powerful, water soluble polyphenol and antioxidant that is easily oxidized. Several thousand types are available in the plant world. As many as two thousand are known to have a flavon structure and are called flavonoids. Catechin is one of them. Green tea is manufactured from fresh, unfermented tea leaves; the oxidation of catechins is minimal, and hence they are able to serve as antioxidants. Researchers believe that catechin is effective because it easily sticks to proteins, blocking bacteria from adhering to cell walls and disrupting their ability to destroy them. Viruses have hooks on their surfaces and can attach to cell walls. The catechin in green tea prevents viruses from adhering and causing harm. Catechin reacts with toxins created by harmful bacteria (many of which belong to the protein family) and harmful metals such as lead, mercury, chrome, and cadmium. From its NMR espectra, there is a doubt on 2 and 3 atoms configuration. It seems to be that they are in trans position. Epicatechin, also known as (+)-cyanidanol-3 or 2,3-cis-epicatechin, is a member of the class of compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Thus, epicatechin is considered to be a flavonoid lipid molecule. Epicatechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epicatechin can be found in cashew nut, which makes epicatechin a potential biomarker for the consumption of this food product. Epicatechin can be found primarily in blood, feces, and urine, as well as throughout most human tissues. Epicatechin is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite. It belongs to the group of flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids . (-)-epicatechin is a catechin with (2R,3R)-configuration. It has a role as an antioxidant. It is a polyphenol and a catechin. It is an enantiomer of a (+)-epicatechin. Epicatechin has been used in trials studying the treatment of Pre-diabetes. (-)-Epicatechin is a natural product found in Visnea mocanera, Litsea rotundifolia, and other organisms with data available. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. See also: Crofelemer (monomer of); Bilberry (part of); Cats Claw (part of) ... View More ... A catechin with (2R,3R)-configuration. [Raw Data] CB030_(-)-Epicatechin_pos_20eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_50eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_40eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_10eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_30eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_neg_50eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_30eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_10eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_40eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_20eV_000009.txt Epicatechin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=490-46-0 (retrieved 2024-07-09) (CAS RN: 490-46-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB.

   

Catechin

(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C15H14O6 (290.079)


Catechin, also known as cyanidanol or catechuic acid, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Catechin also belongs to the group of compounds known as flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids. Catechin is one of the 4 catechin known diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin. The most common catechin isomer is the (+)-catechin. The other stereoisomer is (-)-catechin or ent-catechin. The most common epicatechin isomer is (-)-epicatechin. Catechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Catechin is a bitter tasting compound and is associated with the bitterness in tea. Catechin is a plant secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Catechin is an antioxidant flavonoid, occurring especially in woody plants as both Catechin and (-)-Catechin (cis) forms. Outside of the human body, Catechin is found, on average, in the highest concentration in foods, such as blackcurrants (Ribes nigrum), evergreen blackberries (Rubus laciniatus), and blackberries (Rubus) and in a lower concentration in dills (Anethum graveolens), hot chocolates, and medlars (Mespilus germanica). Catechin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), apple ciders, peanuts (Arachis hypogaea), fruit juices, and red teas. This could make catechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Catechin. (+)-catechin is the (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. It has a role as an antioxidant and a plant metabolite. It is an enantiomer of a (-)-catechin. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Cianidanol is a natural product found in Visnea mocanera, Salacia chinensis, and other organisms with data available. Catechin is a metabolite found in or produced by Saccharomyces cerevisiae. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. See also: Gallocatechin (related); Crofelemer (monomer of); Bilberry (part of) ... View More ... Present in red wine. Widespread in plants; found in a variety of foodstuffs especies apricots, broad beans, cherries, chocolate, grapes, nectarines, red wine, rhubarb, strawberries and tea The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. Catechin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=154-23-4 (retrieved 2024-07-12) (CAS RN: 154-23-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1]. (±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1]. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

   

(S)-Boldine

4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol

C19H21NO4 (327.1471)


Boldine is an aporphine alkaloid. Boldine is a natural product found in Lindera umbellata, Damburneya salicifolia, and other organisms with data available. See also: Peumus boldus leaf (part of). (S)-Boldine is found in sweet bay. (S)-Boldine is an alkaloid from Sassafras and the leaves of Peumus boldus (boldo). (S)-Boldine is a flavouring ingredient. Alkaloid from Sassafras and the leaves of Peumus boldus (boldo). Flavouring ingredient. (S)-Boldine is found in sweet bay. D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents > D009466 - Neuromuscular Blocking Agents D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects. Boldine suppresses osteoclastogenesis, improves bone destruction by down-regulating the OPG/RANKL/RANK signal pathway and may be a potential therapeutic agent for rheumatoid arthritis[1]. Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects. Boldine suppresses osteoclastogenesis, improves bone destruction by down-regulating the OPG/RANKL/RANK signal pathway and may be a potential therapeutic agent for rheumatoid arthritis[1].

   

5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one

2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)- (9CI)

C14H12O3 (228.0786)


5,6-Dehydrokawain is an aromatic ether and a member of 2-pyranones. Desmethoxyyangonin is a natural product found in Alpinia blepharocalyx, Alpinia rafflesiana, and other organisms with data available. See also: Piper methysticum root (part of). 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one is found in beverages. 5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one is found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damag Found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B. Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B.

   

Pinocembrin

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (S)-(-)-

C15H12O4 (256.0736)


Pinocembrin is a dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea. It has a role as an antioxidant, an antineoplastic agent, a vasodilator agent, a neuroprotective agent and a metabolite. It is a dihydroxyflavanone and a (2S)-flavan-4-one. Pinocembrin is a natural product found in Prunus leveilleana, Alpinia rafflesiana, and other organisms with data available. Pinocembrin is found in mexican oregano and is isolated from many plants including food plants. Pinocembrin belongs to the family of flavanones. These are compounds containing a flavan-3-one moiety, which structure is characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. A dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea. Isolated from many plants including food plants. (S)-Pinocembrin is found in mexican oregano and pine nut. (±)-Pinocembrin ((±)-5,7-Dihydroxyflavanone) is a GPR120 ligand able to promote wound healing in HaCaT cell line[1]. (±)-Pinocembrin ((±)-5,7-Dihydroxyflavanone) is a GPR120 ligand able to promote wound healing in HaCaT cell line[1]. Pinocembrin ((+)-Pinocoembrin) is a flavonoid found in propolis, acts as a competitive inhibitor of histidine decarboxylase, and is an effective anti-allergic agent, with antioxidant, antimicrobial and anti-inflammatory properties[1]. Pinocembrin ((+)-Pinocoembrin) is a flavonoid found in propolis, acts as a competitive inhibitor of histidine decarboxylase, and is an effective anti-allergic agent, with antioxidant, antimicrobial and anti-inflammatory properties[1].

   

Procyanidin B2

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)


Procyanidin B2 is a proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 8 in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cats claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine. It has a role as a metabolite and an antioxidant. It is a hydroxyflavan, a proanthocyanidin, a biflavonoid and a polyphenol. It is functionally related to a (-)-epicatechin. Procyanidin B2 is a natural product found in Begonia fagifolia, Saraca asoca, and other organisms with data available. See also: Cocoa (part of); Primula veris flower (part of). A proanthocyanidin consisting of two molecules of (-)-epicatechin joined by a bond between positions 4 and 8 in a beta-configuration. Procyanidin B2 can be found in Cinchona pubescens (Chinchona, in the rind, bark and cortex), in Cinnamomum verum (Ceylon cinnamon, in the rind, bark and cortex), in Crataegus monogyna (Common hawthorn, in the flower and blossom), in Uncaria guianensis (Cats claw, in the root), in Vitis vinifera (Common grape vine, in the leaf), in Litchi chinensis (litchi, in the pericarp), in the apple, in Ecdysanthera utilis and in red wine. Present in red wine. Procyanidin B2 is found in many foods, some of which are alcoholic beverages, sherry, bilberry, and yellow zucchini. Procyanidin B2 is found in alcoholic beverages. Procyanidin B2 is present in red wine. Procyanidin B2 is a natural flavonoid, with anti-cancer, antioxidant activities. Procyanidin B2 is a natural flavonoid, with anti-cancer, antioxidant activities.

   

Laurolitsine

4,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-5,15-diol

C18H19NO4 (313.1314)


Laurolistine is an aporphine alkaloid that is noraporphine substituted by hydroxy groups at positions 2 and 9 and methoxy groups at positions 1 and 10. Isolated from Litsea glutinosa and Lindera chunii, exhibits inhibitory activity against HIV-1 integrase. It has a role as a metabolite and a HIV-1 integrase inhibitor. It is a member of phenols, an aromatic ether and an aporphine alkaloid. It is functionally related to an aporphine. Laurolitsine is a natural product found in Damburneya salicifolia, Neolitsea sericea, and other organisms with data available. Laurolitsine is an alkaloid from Sassafras and the leaves of Peumus boldus (boldo). Laurolitsine is a flavouring ingredient. Alkaloid from Sassafras and the leaves of Peumus boldus (boldo). Flavouring ingredient

   

3,7-Dimethyl-1,6-octadien-3-ol

Linalool, certified reference material, TraceCERT(R)

C10H18O (154.1358)


3,7-Dimethyl-1,6-octadien-3-ol, also known simply as linalool is a naturally occurring terpene alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalool has a role as a plant metabolite, a volatile oil component, an antimicrobial agent and a fragrance. There are two stereoisomers of Linalool ‚Äö√Ñ√¨ (S)-linalool and (R)-linalool. Linalool is used as a scent in 60\\\\\% to 80\\\\\% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions. Linalool is also used by pest professionals as a flea, fruit fly, and cockroach insecticide. Linalool is found in more than 200 different species of plants, including many flowers and spice plants. (S)-linalool is found, for example, as a major constituent of the essential oils of coriander (Coriandrum sativum L.), cymbopogon (Cymbopogon martini var. martinii), and sweet orange (Citrus sinensis) flowers. (R)-linalool is present in lavender (Lavandula officinalis), bay laurel (Laurus nobilis), and sweet basil (Ocimum basilicum), among others. Linalool is also found in plants from the Lamiaceae family (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), Cinnamomum tamala, Solidago Meyen, Artemisia vulgaris (mugwort), Humulus lupulus. Linalool is also one of several monoterpenes that are found in cannabis plants (PMID:6991645 ). There are more than 140 known terpenes in cannabis and the combination of these terepenoids produces the skunky, fruity odor characteristic of C. savita. Like the majority of monoterpenes, linalool starts with the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl pyrophosphate (GPP) (PMID:7640522 ). Linalool is then synthesized with the aid of linalool synthase (LIS) (PMID:12572612 ). Linalool has a citrus, floral, rose, woody aroma and a citrus, orange, waxy taste. Linalool is found in a few different foods and spices, such as spearmints, corianders, common thymes, limes, grapes, lemons, grapefruit, oranges, pineapples, blackcurrants, basil, and common oregano. This could make, Linalool a potential biomarker for the consumption of these foods. Linalool is also synthesized, de novo, by yeast (C. cerevisiae) and may contribute to the floral tones found in some wines (PMID:15668008 ). Linalool is a monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum. It has a role as a plant metabolite, a volatile oil component, an antimicrobial agent and a fragrance. It is a tertiary alcohol and a monoterpenoid. Linalool is a natural product found in Nepeta nepetella, Teucrium montanum, and other organisms with data available. 3,7-Dimethyl-1,6-octadien-3-ol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Cinnamon Leaf Oil (part of); Clary Sage Oil (part of); Cannabis sativa subsp. indica top (part of) ... View More ... A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum. Flavouring agent. Widespread natural occurrence as the optically active and racemic forms in over 200 essential oilsand is) also present in numerous fruits. D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals Linalool is natural monoterpene in essential olis of coriander, acts as a competitive antagonist of Nmethyl d-aspartate (NMDA) receptor, with anti-tumor, anti-cardiotoxicity activity[1].Linalool is a PPARα ligand that reduces plasma TG levels and rewires the hepatic transcriptome and plasma metabolome[2]. Linalool is a natural monoterpene which is a competitive NMDA receptor antagonist. Linalool is orally active and crosses the blood-brain barrier. Linalool has anticancer, antibacterial, anti-inflammatory, neuroprotective, anxiolytic, antidepressant, anti-stress, cardioprotective, hepatoprotective, nephroprotective and pulmonary protective activities[1][2][3][4][5]. Linalool is natural monoterpene in essential olis of coriander, acts as a competitive antagonist of Nmethyl d-aspartate (NMDA) receptor, with anti-tumor, anti-cardiotoxicity activity[1].Linalool is a PPARα ligand that reduces plasma TG levels and rewires the hepatic transcriptome and plasma metabolome[2].

   

Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin

InChI=1/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46

C45H36O18 (864.1902)


Cinnamtannin B-1 is a proanthocyanidin found in Cinnamomum cassia and Cinnamomum zeylanicum. It has a role as a cyclooxygenase 2 inhibitor and a plant metabolite. Cinnamtannin B1 is a natural product found in Cinnamomum aromaticum, Cinnamomum burmanni, and other organisms with data available. See also: Cinnamon (part of). Isolated from cinnamon bark (Cinnamomum zeylanicum) and from cowberry (Vaccinium vitis-idaea). Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin is found in many foods, some of which are fruits, herbs and spices, ceylon cinnamon, and lingonberry. Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin is found in ceylan cinnamon. Epicatechin-(2beta->7,4beta->8)-epicatechin-(4beta->8)-epicatechin is isolated from cinnamon bark (Cinnamomum zeylanicum) and from cowberry (Vaccinium vitis-idaea). A proanthocyanidin found in Cinnamomum cassia and Cinnamomum zeylanicum. Cinnamtannin B-1 is a proanthocyanidin with multiple biological functions, including antioxidant effects and inhibiting the production of reactive oxygen species (ROS). Cinnamtannin B-1 inhibits RANKL-induced osteoclastogenesis and prevents ovariectomy-induced osteoporosis in vivo. Cinnamtannin B-1 can be used for the research osteoporosis and colon cancers[1][2].

   

Geranyl acetate

Geranyl acetate, food grade (71\\% geranyl acetate, 29\\% citronellyl acetate)

C12H20O2 (196.1463)


Geranyl acetate is a clear colorless liquid with an odor of lavender. (NTP, 1992) Geranyl acetate is a monoterpenoid that is the acetate ester derivative of geraniol. It has a role as a plant metabolite. It is an acetate ester and a monoterpenoid. It is functionally related to a geraniol. Geranyl acetate is a natural product found in Nepeta nepetella, Xylopia sericea, and other organisms with data available. See also: Lemon oil, cold pressed (part of); Coriander Oil (part of); Java citronella oil (part of). Neryl acetate is found in cardamom. Neryl acetate is found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries. Neryl acetate is a flavouring agent A monoterpenoid that is the acetate ester derivative of geraniol. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2]. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2].

   

Isoteolin

4H-Dibenzo(de,g)quinolinediol, 5,6,6a,7-tetrahydro-2,9(or 2,10)-dimethoxy-6-methyl-, (S)-

C19H21NO4 (327.1471)


Isoboldine is an aporphine alkaloid. (+)-Isoboldine is a natural product found in Fumaria capreolata, Thalictrum foetidum, and other organisms with data available. See also: Peumus boldus leaf (part of).

   

procyanidin B2

(2S,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol

C30H26O12 (578.1424)


Annotation level-1 Acquisition and generation of the data is financially supported in part by CREST/JST. Procyanidin B2 is a natural flavonoid, with anti-cancer, antioxidant activities. Procyanidin B2 is a natural flavonoid, with anti-cancer, antioxidant activities.

   

1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenyl-1-propanone

1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenyl-1-propanone

C16H16O4 (272.1049)


1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenyl-1-propanone is isolated from Populus balsamifera (balsam poplar) oi Isolated from Populus balsamifera (balsam poplar) oil.

   

Pinostrobin

(2R)-5-hydroxy-7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

C16H14O4 (270.0892)


A monohydroxyflavanone that is (2S)-flavanone substituted by a hydroxy group at position 5 and a methoxy group at position 7 respectively. Pinostrobin is a natural product found in Uvaria chamae, Zuccagnia punctata, and other organisms with data available.

   

Palmitone

hentriacontan-16-one

C31H62O (450.48)


Constituent of Piper nigrum (pepper). Palmitone is found in herbs and spices, pepper (spice), and potato. Palmitone is found in herbs and spices. Palmitone is a constituent of Piper nigrum (pepper)

   

(S)-Carvone

D-Carvone 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one

C10H14O (150.1045)


Carvone, with R and S isomers, also known as carvol or limonen-6-one, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m-menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Carvone is a neutral compound. Carvone is a naturally occurring organic compound found in many essential oils but is most abundant in the oils from caraway seeds (Carum carvi), spearmint (Mentha spicata), and dill (PMID:27427817). Carvone is occasionally found as a component of biological fluids in normal individuals. Both carvones (R, S) are used in the food and flavor industry (http//doi:10.1016/j.foodchem.2005.01.003). R-carvone is also used in air freshening products and in essential oils used in aromatherapy and alternative medicine. Caraway was used for medicinal purposes by the ancient Romans, but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in 1841 (PMID:5556886 , 2477620 ). Carvone may help in the management of diseases (PMID:30374904) and had been considered as an adjuvant for treatment of cancer patients (PMID:30087792) and patients with epilepsy (PMID:31239862). It also has been successfully used as a biopesticide (PMID:30250476). D-carvone appears as pale yellow or colorless liquid. (NTP, 1992) (+)-carvone is a carvone having (S) configuration. It is an enantiomer of a (-)-carvone. d-Carvone is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. See also: Caraway Oil (part of). A carvone having (S) configuration.

   

Cinnamtannin D1

(1R,5R,6R,7S,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-7-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19,21-pentol

C45H36O18 (864.1902)


Cinnamtannin D1 is found in fruits. Cinnamtannin D1 is isolated from cowberry (Vaccinium vitis-idaea). Isolated from cowberry (Vaccinium vitis-idaea). Cinnamtannin D1 is found in fruits and lingonberry.

   

Pinostrobin chalcone

2-Propen-1-one, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-, (E)-; Chalcone, 2,6-dihydroxy-4-methoxy- ; 2,6-Dihydroxy-4-methoxychalcone

C16H14O4 (270.0892)


Pinostrobin chalcone is a member of chalcones. Pinostrobin chalcone is a natural product found in Onychium siliculosum, Populus koreana, and other organisms with data available. Pinostrobin chalcone is found in pulses. Pinostrobin chalcone is isolated from Cajanus cajan (pigeon pea). Isolated from Cajanus cajan (pigeon pea). Pinostrobin chalcone is found in pulses. Pinostrobin chalcone is found to be potent natural cytotoxic compounds against MDA-MB-231 and HT-29 colon cancer cell lines(IC50 = 20.42±2.23 and 22.51±0.42 μg/mL)[1]. Pinostrobin chalcone is found to be potent natural cytotoxic compounds against MDA-MB-231 and HT-29 colon cancer cell lines(IC50 = 20.42±2.23 and 22.51±0.42 μg/mL)[1].

   

Laurotetanine

4,15,16-trimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaen-5-ol

C19H21NO4 (327.1471)


Laurotetanine is found in cherimoya. Laurotetanine is an alkaloid from the leaves of Peumus boldus (boldo Alkaloid from the leaves of Peumus boldus (boldo). Laurotetanine is found in cherimoya.

   

2,4,6-Trihydroxydihydrochalcone

2,4,6-Trihydroxydihydrochalcone

C15H14O4 (258.0892)


   

3'-O-methyl-(-)-epicatechin

(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C16H16O6 (304.0947)


3-O-methyl-(-)-epicatechin is an urinary and gut-derived metabolite of epicatechin.

   

Tsuzuic acid

(4Z)-tetradec-4-enoic acid

C14H26O2 (226.1933)


Tsuzuic acid is a fatty acid. Tsuzuic acid is found in the seeds of some plants from the Lauraceae family, and is occasionally found in human adipose tissue and biofluids. It has been part of a screening analysis to identify fatty acid beta-oxidation disorders. (CAN 136:180078, PMID: 3372640, 11750281, 17805664) [HMDB] Tsuzuic acid is a fatty acid. Tsuzuic acid is found in the seeds of some plants from the Lauraceae family, and is occasionally found in human adipose tissue and biofluids. It has been part of a screening analysis to identify fatty acid beta-oxidation disorders. (CAN 136:180078, PMID: 3372640, 11750281, 17805664).

   

cis-4-Decenoic acid

(4Z)-dec-4-enoic acid

C10H18O2 (170.1307)


cis-4-Decenoic acid, also known as obtusilic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. cis-4-Decenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Decenoic acid (and other intermediates of unsaturated fatty acid oxidation) has been found in increased amounts in liver, skeletal muscle, and heart obtained post mortem from patients with medium-chain acyl-CoA dehydrogenase deficiency (MCADD), multiple acyl-CoA dehydrogenase deficiency (MADD), and very-long-chain acyl-CoA dehydrogenase deficiency (VLCADD) (PMID: 11486898). Occurs in hops and beer. Comly. available flavour ingredient. 4-Decenoic acid is found in alcoholic beverages.

   

Carvone

2-Methyl-5-(1-methyl-1-ethenyl)-2-cyclohexen-1-one

C10H14O (150.1045)


Carvone is found in anise. Carvone is a flavouring ingredient Flavouring ingredient. Constituent of gingergrass oil

   

Arachidoside

2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C16H16O6 (304.0947)


Arachidoside is found in nuts. Arachidoside is isolated from shells of peanuts (Arachis hypogaea). Isolated from shells of peanuts (Arachis hypogaea). Arachidoside is found in nuts.

   

(2R)-5-Hydroxy-7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

(2R)-5-hydroxy-7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

C16H14O4 (270.0892)


Pinostrobin, also known as 5-hydroxy-7-methoxyflavanone, 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, pinostrobin is considered to be a flavonoid lipid molecule. Pinostrobin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pinostrobin can be found in a number of food items such as roman camomile, soursop, rocket salad, and angelica, which makes pinostrobin a potential biomarker for the consumption of these food products.

   

linderatone

(2S)-2,3-Dihydro-5,7-dihydroxy-6-[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]-2-phenyl-4H-1-benzopyran-4-one

C25H28O4 (392.1987)


   

Neolinderatone

(2S)-2,3-Dihydro-5,7-dihydroxy-6,8-bis[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]-2-phenyl-4H-1-benzopyran-4-one

C35H44O4 (528.3239)


   

Linderic acid

4-dodecenoic acid

C12H22O2 (198.162)


   

Desmethoxyyangonin

Desmethoxyyangonin

C14H12O3 (228.0786)


Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B. Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B.

   

2,4,6-Trihydroxydihydrochalcone

3-Phenyl-1- (2,4,6-trihydroxyphenyl) -1-propanone

C15H14O4 (258.0892)


   

Methyllinderatin

2,6-Dihydroxy-3- (6-isopropyl-3-methylcyclohex-2-enyl) -4-methoxydihydrochalcone

C26H32O4 (408.23)


   

(-)-Linderatin

(1S-trans)-3-Phenyl-1-[2,4,6-trihydroxy-3-[3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl]-propanone

C25H30O4 (394.2144)


   

Linderachalcone

(2E)-3-Phenyl-1-[2,4,6-trihydroxy-3-[(1S,6S)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl]-2-propen-1-one

C25H28O4 (392.1987)


   

Neolinderachalcone

(3"S,4"R,3"S,4"R) -2,4,6-Trihydroxy-3,5-bis (4-isopropyl-1-methylcyclohex-1-en-3-yl) chalcone

C35H44O4 (528.3239)


   

Neolinderatin

3-Phenyl-1-[2,4,6-trihydroxy-3,5-bis[(1R,6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]phenyl]-1-propanone

C35H46O4 (530.3396)


   

Pashanone

2-Propen-1-one, 1-(2,6-dihydroxy-3,4-dimethoxyphenyl)-3-phenyl-, (E)-; (2E)-1-(2,6-Dihydroxy-3,4-dimethoxyphenyl)-3-phenyl-2-propen-1-one

C17H16O5 (300.0998)


Pashanone is a natural product found in Onychium siliculosum, Lindera erythrocarpa, and other organisms with data available.

   

Symplocosidin

(2R,3R) -3,5,7,4-Tetrahydroxy-3-methoxyflavan

C16H16O6 (304.0947)


   

Catechin

(+)-Catechin Hydrate

C15H14O6 (290.079)


Annotation level-1 Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

   

DODEC-4-ENOIC ACID

DODEC-4-ENOIC ACID

C12H22O2 (198.162)


   

4-Decenoic acid

4-Decenoic acid

C10H18O2 (170.1307)


   

pinocembrine

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)-

C15H12O4 (256.0736)


4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R)- is a natural product found in Alpinia nutans, Alpinia zerumbet, and Boesenbergia rotunda with data available.

   

Pinocembrin

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (S)-(-)-

C15H12O4 (256.0736)


(2s)-pinocembrin, also known as 5,7-dihydroxyflavanone or dihydrochrysin, is a member of the class of compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, (2s)-pinocembrin is considered to be a flavonoid lipid molecule (2s)-pinocembrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (2s)-pinocembrin can be found in a number of food items such as acorn, lentils, mulberry, and sorghum, which makes (2s)-pinocembrin a potential biomarker for the consumption of these food products. (s)-pinocembrin, also known as 5,7-dihydroxyflavanone or dihydrochrysin, is a member of the class of compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3 (s)-pinocembrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-pinocembrin is a bitter tasting compound found in mexican oregano and tarragon, which makes (s)-pinocembrin a potential biomarker for the consumption of these food products. relative retention time with respect to 9-anthracene Carboxylic Acid is 1.069 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.067 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.071 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.070 5,7-Dihydroxyflavanone is a natural product found in Pinus contorta var. latifolia, Piper nigrum, and other organisms with data available. (±)-Pinocembrin ((±)-5,7-Dihydroxyflavanone) is a GPR120 ligand able to promote wound healing in HaCaT cell line[1]. (±)-Pinocembrin ((±)-5,7-Dihydroxyflavanone) is a GPR120 ligand able to promote wound healing in HaCaT cell line[1]. Pinocembrin ((+)-Pinocoembrin) is a flavonoid found in propolis, acts as a competitive inhibitor of histidine decarboxylase, and is an effective anti-allergic agent, with antioxidant, antimicrobial and anti-inflammatory properties[1]. Pinocembrin ((+)-Pinocoembrin) is a flavonoid found in propolis, acts as a competitive inhibitor of histidine decarboxylase, and is an effective anti-allergic agent, with antioxidant, antimicrobial and anti-inflammatory properties[1].

   

Boldine

4H-Dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6aS)-

C19H21NO4 (327.1471)


Boldine is an aporphine alkaloid. Boldine is a natural product found in Lindera umbellata, Damburneya salicifolia, and other organisms with data available. See also: Peumus boldus leaf (part of). D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents > D009466 - Neuromuscular Blocking Agents D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents (s)-boldine is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof (s)-boldine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-boldine can be found in sweet bay, which makes (s)-boldine a potential biomarker for the consumption of this food product. Origin: Plant; Formula(Parent): C19H21NO4; Bottle Name:Boldine hydrochloride; PRIME Parent Name:Boldine; PRIME in-house No.:V0322; SubCategory_DNP: Isoquinoline alkaloids, Benzylisoquinoline alkaloids Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.487 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.480 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.482 IPB_RECORD: 841; CONFIDENCE confident structure Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects. Boldine suppresses osteoclastogenesis, improves bone destruction by down-regulating the OPG/RANKL/RANK signal pathway and may be a potential therapeutic agent for rheumatoid arthritis[1]. Boldine is an aporphine isoquinoline alkaloid extracted from the root of Litsea cubeba and also possesses these properties, including antioxidant, anti-inflammatory and cytoprotective effects. Boldine suppresses osteoclastogenesis, improves bone destruction by down-regulating the OPG/RANKL/RANK signal pathway and may be a potential therapeutic agent for rheumatoid arthritis[1].

   

Catechol

(+)-Catechin Hydrate

C15H14O6 (290.079)


Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

   

1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one

NCGC00384536-01!1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one

C16H16O4 (272.1049)


   

3-phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one

NCGC00168937-02!3-phenyl-1-(2,4,6-trihydroxyphenyl)propan-1-one

C15H14O4 (258.0892)


   

Laurotetanine

Laurotetanine

C19H21NO4 (327.1471)


   
   

caryophyllene

(-)-beta-Caryophyllene

C15H24 (204.1878)


A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

   

Tsuzuic acid

4-tetradecenoic acid

C14H26O2 (226.1933)


   

(+)-Linderatin

(+)-Linderatin

C25H30O4 (394.2144)


   

Arachidoside

2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C16H16O6 (304.0947)


   

FA 14:1

2-Heptylcyclopropanebutanoic acid

C14H26O2 (226.1933)


   

palmitone

hentriacontan-16-one

C31H62O (450.48)


   

Pinocembrin-7-methyl ether

5-hydroxy-7-methoxy-2-phenylchroman-4-one

C16H14O4 (270.0892)


   

Geranyl acetate

[(2E)-3,7-dimethylocta-2,6-dienyl] acetate

C12H20O2 (196.1463)


Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2]. Geranyl acetate has been reported in Cymbopogon martinii, Cymbopogon distans

   

AIDS-224739

2H-Pyran-2-one, 4-methoxy-6-(2-phenylethenyl)-, (E)- (9CI)

C14H12O3 (228.0786)


Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B. Desmethoxyyangonin is one of the six major kavalactones found in the Piper methysticum (kava) plant; reversible inhibitor of MAO-B.

   

KB-53

2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-trans)-

C15H14O6 (290.079)


Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

   

Carvol

2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5S)-

C10H14O (150.1045)


   

3'-O-methyl-(-)-epicatechin

(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C16H16O6 (304.0947)


3-O-methyl-(-)-epicatechin is an urinary and gut-derived metabolite of epicatechin. A polyphenol metabolite detected in biological fluids [PhenolExplorer]

   

16-Hentriacontanone

hentriacontan-16-one

C31H62O (450.48)


A dialkyl ketone that is hentriacontane in which the hydrogens at position 16 are replaced by an oxo group.

   

1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one

1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one

C16H16O4 (272.1049)


   

Cinnamtannin D1

Cinnamtannin D1

C45H36O18 (864.1902)


   

cinnamtannin D-1

cinnamtannin D-1

C45H36O18 (864.1902)


A proanthocyanidin found in Cinnamomum cassia.

   

(2s)-5,7-dihydroxy-8-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2s)-5,7-dihydroxy-8-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C25H28O4 (392.1987)


   

3-phenyl-1-[2,4,6-trihydroxy-3,5-bis(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]propan-1-one

3-phenyl-1-[2,4,6-trihydroxy-3,5-bis(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]propan-1-one

C35H46O4 (530.3396)


   

(2r)-5,7-dihydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2r)-5,7-dihydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C25H28O4 (392.1987)


   

(2s)-5-hydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2s)-5-hydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C26H30O4 (406.2144)


   

1-{2,6-dihydroxy-3-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-4-methoxyphenyl}-3-phenylpropan-1-one

1-{2,6-dihydroxy-3-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-4-methoxyphenyl}-3-phenylpropan-1-one

C26H32O4 (408.23)


   

3-phenyl-1-[2,4,6-trihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]prop-2-en-1-one

3-phenyl-1-[2,4,6-trihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]prop-2-en-1-one

C25H28O4 (392.1987)


   

1-{5,10-dihydroxy-13-isopropyl-3-methoxy-10-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5-trien-6-yl}-3-phenylprop-2-en-1-one

1-{5,10-dihydroxy-13-isopropyl-3-methoxy-10-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5-trien-6-yl}-3-phenylprop-2-en-1-one

C26H30O5 (422.2093)


   

1-[2,6-dihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-4-methoxyphenyl]-3-phenylpropan-1-one

1-[2,6-dihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-4-methoxyphenyl]-3-phenylpropan-1-one

C26H32O4 (408.23)


   

3-phenyl-1-[2,4,6-trihydroxy-3,5-bis(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]prop-2-en-1-one

3-phenyl-1-[2,4,6-trihydroxy-3,5-bis(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]prop-2-en-1-one

C35H44O4 (528.3239)


   

(2e)-3-phenyl-1-{2,4,6-trihydroxy-3-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]phenyl}prop-2-en-1-one

(2e)-3-phenyl-1-{2,4,6-trihydroxy-3-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]phenyl}prop-2-en-1-one

C25H28O4 (392.1987)


   

2-(3,4-dimethoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

2-(3,4-dimethoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C17H18O6 (318.1103)


   

(1r,3ar,3br,7s,9ar,9br,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3ar,3br,7s,9ar,9br,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H50O (414.3861)


   

1-[2,6-dihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-4-methoxyphenyl]-3-phenylprop-2-en-1-one

1-[2,6-dihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-4-methoxyphenyl]-3-phenylprop-2-en-1-one

C26H30O4 (406.2144)


   

5-hydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

5-hydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C26H30O4 (406.2144)


   

(2e)-1-[(1s,9r,10r,13r)-5,10-dihydroxy-13-isopropyl-3-methoxy-10-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5-trien-6-yl]-3-phenylprop-2-en-1-one

(2e)-1-[(1s,9r,10r,13r)-5,10-dihydroxy-13-isopropyl-3-methoxy-10-methyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5-trien-6-yl]-3-phenylprop-2-en-1-one

C26H30O5 (422.2093)


   

5-hydroxy-6-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

5-hydroxy-6-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C26H30O4 (406.2144)


   

(2e)-1-[(1s,9r,10r,13s)-5,10-dihydroxy-3-methoxy-10-methyl-13-propyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-2,4,6-trien-6-yl]-3-phenylprop-2-en-1-one

(2e)-1-[(1s,9r,10r,13s)-5,10-dihydroxy-3-methoxy-10-methyl-13-propyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-2,4,6-trien-6-yl]-3-phenylprop-2-en-1-one

C26H30O5 (422.2093)


   

(12s)-17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaen-18-ol

(12s)-17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaen-18-ol

C18H17NO4 (311.1158)


   

(9s)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,16-diol

(9s)-4,15-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,16-diol

C19H21NO4 (327.1471)


   

2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3,4-dihydro-2h-1-benzopyran-3,7-diol

2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3,4-dihydro-2h-1-benzopyran-3,7-diol

C17H18O6 (318.1103)


   

(9s)-4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,15-diol

(9s)-4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,15-diol

C19H21NO4 (327.1471)


   

(2s)-5-hydroxy-8-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2s)-5-hydroxy-8-[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C26H30O4 (406.2144)


   

(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2h-1-benzopyran-3-ol

(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2h-1-benzopyran-3-ol

C18H20O6 (332.126)


   

(2r,3r)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

(2r,3r)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)


   

4,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-5,15-diol

4,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-5,15-diol

C18H19NO4 (313.1314)


   

(2e)-1-{2,6-dihydroxy-3-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-4-methoxyphenyl}-3-phenylprop-2-en-1-one

(2e)-1-{2,6-dihydroxy-3-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-4-methoxyphenyl}-3-phenylprop-2-en-1-one

C26H30O4 (406.2144)


   

(2r,3r,4r)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

(2r,3r,4r)-2-(3,4-dihydroxyphenyl)-4-[(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2h-1-benzopyran-8-yl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C30H26O12 (578.1424)


   

5-hydroxy-8-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

5-hydroxy-8-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-7-methoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C26H30O4 (406.2144)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)


   

5,7-dihydroxy-8-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one

5,7-dihydroxy-8-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C25H28O4 (392.1987)


   

4-[2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-5-methoxybenzene-1,3-diol

4-[2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-5-methoxybenzene-1,3-diol

C17H20O6 (320.126)


   

(2r,3r)-2-(3,4-dimethoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

(2r,3r)-2-(3,4-dimethoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

C17H18O6 (318.1103)


   

(2r)-5,7-dihydroxy-6,8-bis[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2r)-5,7-dihydroxy-6,8-bis[(1s,6s)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C35H44O4 (528.3239)


   

4-[(2s)-2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-5-methoxybenzene-1,3-diol

4-[(2s)-2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propyl]-5-methoxybenzene-1,3-diol

C17H20O6 (320.126)


   

2-(4-hydroxy-3-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2h-1-benzopyran-3-ol

2-(4-hydroxy-3-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2h-1-benzopyran-3-ol

C18H20O6 (332.126)


   

17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaen-18-ol

17-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),14,16,18-hexaen-18-ol

C18H17NO4 (311.1158)


   

3-phenyl-1-[2,4,6-trihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]propan-1-one

3-phenyl-1-[2,4,6-trihydroxy-3-(6-isopropyl-3-methylcyclohex-2-en-1-yl)phenyl]propan-1-one

C25H30O4 (394.2144)


   

(2s)-5,7-dihydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

(2s)-5,7-dihydroxy-6-[(1r,6r)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C25H28O4 (392.1987)


   

(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3,4-dihydro-2h-1-benzopyran-3,7-diol

(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3,4-dihydro-2h-1-benzopyran-3,7-diol

C17H18O6 (318.1103)