NCBI Taxonomy: 182387

Monarda punctata (ncbi_taxid: 182387)

found 59 associated metabolites at species taxonomy rank level.

Ancestor: Monarda

Child Taxonomies: none taxonomy data.

Rosmarinic acid

BENZENEPROPANOIC ACID, .ALPHA.-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (.ALPHA.R)-

C18H16O8 (360.0845136)


Rosmarinic acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid. It is commonly found in species of the Boraginaceae and the subfamily Nepetoideae of the Lamiaceae. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. Rosmarinic acid is one of the polyphenolic substances contained in culinary herbs such as perilla (Perilla frutescens L.), rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), mint (Mentha arvense L.), and basil (Ocimum basilicum L.). These herbs are commonly grown in the garden as kitchen herbs, and while used to add flavor in cooking, are also known to have several potent physiological effects (PMID: 12482446, 15120569). BioTransformer predicts that rosmarinic acid is a product of methylrosmarinic acid metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in humans and human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223). (R)-rosmarinic acid is a stereoisomer of rosmarinic acid having (R)-configuration. It has a role as a plant metabolite and a geroprotector. It is a conjugate acid of a (R)-rosmarinate. It is an enantiomer of a (S)-rosmarinic acid. Rosmarinic acid is a natural product found in Dimetia scandens, Scrophularia scorodonia, and other organisms with data available. See also: Rosemary Oil (part of); Comfrey Root (part of); Holy basil leaf (part of) ... View More ... D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors Isolated from rosemary, mint, sage, thyme, lemon balm and other plants D002491 - Central Nervous System Agents > D000700 - Analgesics A stereoisomer of rosmarinic acid having (R)-configuration. 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. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively.

   

Apiin

7-(((2S,3R,4S,5S,6R)-3-(((2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

C26H28O14 (564.1478988)


Apiin is a beta-D-glucoside having a beta-D-apiosyl residue at the 2-position and a 5,4-dihydroxyflavon-7-yl moiety at the anomeric position. It has a role as an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor and a plant metabolite. It is a beta-D-glucoside, a dihydroxyflavone and a glycosyloxyflavone. It is functionally related to an apigenin. It is a conjugate acid of an apiin(1-). Apiin is a natural product found in Crotalaria micans, Limonium axillare, and other organisms with data available. See also: Chamomile (part of); Chamaemelum nobile flower (part of). Apiin is found in celery leaves. Apiin is a constituent of parsley (Petroselinum crispum) and of the flowers of Anthemis nobilis (Roman chamomile). First isolated in 1843 Apiin is a chemical compound isolated from parsley and celery Constituent of parsley (Petroselinum crispum) and of the flowers of Anthemis nobilis (Roman chamomile). First isol. in 1843 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2350 Apiin, a major constituent of Apium graveolens leaves with anti-inflammatory properties. Apiin shows significant inhibitory activity on nitrite (NO) production (IC50 = 0.08 mg/mL) in-vitro and iNOS expression (IC50 = 0.049 mg/ mL) in LPS-activated J774.A1 cells[1]. Apiin, a major constituent of Apium graveolens leaves with anti-inflammatory properties. Apiin shows significant inhibitory activity on nitrite (NO) production (IC50 = 0.08 mg/mL) in-vitro and iNOS expression (IC50 = 0.049 mg/ mL) in LPS-activated J774.A1 cells[1].

   

Cosmosiin

5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one;Apigenin 7-Glucoside

C21H20O10 (432.105642)


Cosmosiin, also known as apigenin 7-O-glucoside or apigetrin, 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. Cosmosiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cosmosiin can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Cosmosiin can also be found in dandelion coffee and in Teucrium gnaphalodes (Wikipedia). Cosmosiin can also be found plants such as wild celery and anise. Cosmosiin has been shown to exhibit anti-platelet function (PMID: 21834233). Apigenin 7-O-beta-D-glucoside is a glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a non-steroidal anti-inflammatory drug, a metabolite and an antibacterial agent. It is a beta-D-glucoside, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to an apigenin. It is a conjugate acid of an apigenin 7-O-beta-D-glucoside(1-). It is an enantiomer of an apigenin 7-O-beta-L-glucoside. Cosmosiin is a natural product found in Galeopsis tetrahit, Carex fraseriana, and other organisms with data available. See also: Chamomile (part of). Apiumetrin, also known as 7-O-beta-D-glucosyl-5,7,4-trihydroxyflavone or cosmosiin, 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. Apiumetrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apiumetrin can be found in wild celery, which makes apiumetrin a potential biomarker for the consumption of this food product. Acquisition and generation of the data is financially supported in part by CREST/JST. Annotation level-1 Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

   

Caffeic acid

(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C9H8O4 (180.0422568)


Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

Luteolin 7-glucuronide

(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

C21H18O12 (462.0798228)


Luteolin 7-glucuronide, also known as cyanidenon-7-O-B-D-glucuronate or luteolin 7-O-beta-D-glucuronopyranoside, is a member of the class of compounds known as flavonoid-7-o-glucuronides. Flavonoid-7-o-glucuronides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Luteolin 7-glucuronide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Luteolin 7-glucuronide can be found in a number of food items such as globe artichoke, wild carrot, carrot, and lettuce, which makes luteolin 7-glucuronide a potential biomarker for the consumption of these food products. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.

   

5-Isopropyl-2-methylphenol

InChI=1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H

C10H14O (150.1044594)


5-Isopropyl-2-methylphenol, also known as 2-hydroxy-p-cymene or 2-p-cymenol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. 5-Isopropyl-2-methylphenol is a very hydrophobic molecule, practically insoluble in water, but fairly soluble in organic solvents. Thus, 5-Isopropyl-2-methylphenol is considered to be an isoprenoid lipid molecule. Thymol is found in the essential oil of thyme and in the essential oils of several different plants. It can be extracted from Thymus vulgaris (common thyme), Ajwain and various other kinds of plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol has also been identified as a volatile compound found in cannabis samples obtained from police seizures (PMID:26657499 ). Carvacrol is a phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). It has a role as a volatile oil component, a flavouring agent, an antimicrobial agent, an agrochemical and a TRPA1 channel agonist. It is a member of phenols, a p-menthane monoterpenoid and a botanical anti-fungal agent. It derives from a hydride of a p-cymene. Carvacrol is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. Carvacrol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Oregano Leaf Oil (part of). A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1). Constituent of many essential oils. Especies found in the Labiatae. Thyme oil (=70\\\\%) and Origanum oil (=80\\\\%) are rich sources. Flavouring ingredient COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Carvacrol is a monoterpenoid phenol isolated from Thymus mongolicus Ronn., with antioxidant, anti-inflammatory and anticancer properties. Carvacrol causes cell cycle arrest in G0/G1, downregulates Notch-1, and Jagged-1, and induces apoptosis[1]. Carvacrol is a monoterpenoid phenol isolated from Thymus mongolicus Ronn., with antioxidant, anti-inflammatory and anticancer properties. Carvacrol causes cell cycle arrest in G0/G1, downregulates Notch-1, and Jagged-1, and induces apoptosis[1].

   

6'-Malonylcosmosiin

3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]propanoic acid

C24H22O13 (518.1060362000001)


Apigenin 7-O-(6-malonyl-beta-D-glucoside) is a member of flavonoids and a glycoside. Apigenin 7-(6-malonylglucoside) is a natural product found in Monarda punctata and Cynara cardunculus with data available. 6-Malonylcosmosiin is found in herbs and spices. 6-Malonylcosmosiin is isolated from Petroselinum crispum (parsley). Isolated from Petroselinum crispum (parsley). 6-Malonylcosmosiin is found in herbs and spices. Apigenin 7-O-malonylglucoside is found in chrysanthemum flowers[1].

   

Thymol

Thymol, Pharmaceutical Secondary Standard; Certified Reference Material

C10H14O (150.1044594)


Thymol is a phenol that is a natural monoterpene derivative of cymene. It has a role as a volatile oil component. It is a member of phenols and a monoterpenoid. It derives from a hydride of a p-cymene. A phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed) Thymol is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available. A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent. See also: Paeonia lactiflora root (part of); Elymus repens root (part of); Eucalyptol; thymol (component of) ... View More ... Thymol is a phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. Thymol is a monoterpene phenol derivative of cymene, C10H13OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. It is also called "hydroxy cymene". In a 1994 report released by five top cigarette companies, thymol is one of the 599 additives to cigarettes. Its use or purpose, however, is unknown, like most cigarette additives. Found in many essential oils. Especies found in the Labiatae. Rich sources are thyme oil, seed oil of Ptychotis ajowan and oils of horsemint (Monarda punctata) and Ocimum subspecies Flavouring ingredient C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents > D000935 - Antifungal Agents A phenol that is a natural monoterpene derivative of cymene. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1]. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1].

   

Acetaldehyde

Acetic aldehyde

C2H4O (44.0262134)


Acetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde exists in all living species, ranging from bacteria to humans. Within humans, acetaldehyde participates in a number of enzymatic reactions. In particular, acetaldehyde can be biosynthesized from ethanol which is mediated by the enzyme alcohol dehydrogenase 1B. Acetaldehyde can also be converted to acetic acid by the enzyme aldehyde dehydrogenase (mitochondrial) and aldehyde dehydrogenase X (mitochondrial). The main method of production is the oxidation of ethylene by the Wacker process, which involves oxidation of ethylene using a homogeneous palladium/copper system: 2 CH2CH2 + O2 → 2 CH3CHO. In the 1970s, the world capacity of the Wacker-Hoechst direct oxidation process exceeded 2 million tonnes annually. In humans, acetaldehyde is involved in disulfiram action pathway. Acetaldehyde is an aldehydic, ethereal, and fruity tasting compound. Outside of the human body, acetaldehyde is found, on average, in the highest concentration in a few different foods, such as sweet oranges, pineapples, and mandarin orange (clementine, tangerine) and in a lower concentration in . acetaldehyde has also been detected, but not quantified in several different foods, such as malabar plums, malus (crab apple), rose hips, natal plums, and medlars. This could make acetaldehyde a potential biomarker for the consumption of these foods. In condensation reactions, acetaldehyde is prochiral. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases such as alcoholism, ulcerative colitis, nonalcoholic fatty liver disease, and crohns disease; also acetaldehyde has been linked to the inborn metabolic disorders including aldehyde dehydrogenase deficiency (III) sulfate is used to reoxidize the mercury back to the mercury. Acetaldehyde was first observed by the Swedish pharmacist/chemist Carl Wilhelm Scheele (1774); it was then investigated by the French chemists Antoine François, comte de Fourcroy and Louis Nicolas Vauquelin (1800), and the German chemists Johann Wolfgang Döbereiner (1821, 1822, 1832) and Justus von Liebig (1835). At room temperature, acetaldehyde (CH3CHO) is more stable than vinyl alcohol (CH2CHOH) by 42.7 kJ/mol: Overall the keto-enol tautomerization occurs slowly but is catalyzed by acids. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. The water industry generally recognizes 20–40 ppb as the taste/odor threshold for acetaldehyde. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity. Flavouring agent and adjuvant used to impart orange, apple and butter flavours; component of food flavourings added to milk products, baked goods, fruit juices, candy, desserts and soft drinks [DFC]

   

Rosmarinic acid

(S)-rosmarinic acid

C18H16O8 (360.0845136)


The (S)-stereoisomer of rosmarinic acid. The 1-carboxy-2-(2,4-dihydroxyphenyl)ethyl ester of trans-caffeic acid. Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.731 Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively.

   

Apigenin

(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid

C21H18O11 (446.0849078)


Apigenin 7-glucuronide is a member of flavonoids and a glucosiduronic acid. Apigenin 7-glucuronide is a natural product found in Galeopsis tetrahit, Galeopsis ladanum, and other organisms with data available. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively.

   

Luteolin

(2S,3S,4S,5R,6S)-6-((2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

C21H18O12 (462.0798228)


Luteolin 7-O-beta-D-glucosiduronic acid is a luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position. It has a role as a metabolite. It is a trihydroxyflavone, a glycosyloxyflavone, a monosaccharide derivative and a luteolin O-glucuronoside. It is a conjugate acid of a luteolin 7-O-beta-D-glucosiduronate and a luteolin 7-O-beta-D-glucosiduronate(2-). Luteolin 7-glucuronide is a natural product found in Galeopsis tetrahit, Galeopsis ladanum, and other organisms with data available. A luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.

   

Isorhoifolin

5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

C27H30O14 (578.163548)


Isorhoifolin is a natural product found in Astragalus onobrychis, Phillyrea latifolia, and other organisms with data available. Isorhoifolin is found in citrus. Isorhoifolin is isolated from leaves of Citrus paradisi (grapefruit) and other plant species. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2]. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2].

   

Luteolin 7-glucuronide

Luteolin 7-O-glucuronide

C21H18O12 (462.0798228)


Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively. Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.

   

cis-Caffeic acid

(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid

C9H8O4 (180.0422568)


Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g). D020011 - Protective Agents > D000975 - Antioxidants Found in olive oil, peanuts and other plant sources Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

Apigenin 7-glucuronide

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

C21H18O11 (446.0849078)


Apigenin 7-o-glucuronide is a member of the class of compounds known as flavonoid-7-o-glucuronides. Flavonoid-7-o-glucuronides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Apigenin 7-o-glucuronide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Apigenin 7-o-glucuronide can be found in globe artichoke, which makes apigenin 7-o-glucuronide a potential biomarker for the consumption of this food product. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively. Apigenin-7-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 12.87, 22.39, 17.52, 0.27 μM for MMP-3, MMP-8, MMP-9, MMP-13, respectively.

   

Apiin

7-(((2S,3R,4S,5S,6R)-3-(((2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

C26H28O14 (564.1478988)


Apiin is a beta-D-glucoside having a beta-D-apiosyl residue at the 2-position and a 5,4-dihydroxyflavon-7-yl moiety at the anomeric position. It has a role as an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor and a plant metabolite. It is a beta-D-glucoside, a dihydroxyflavone and a glycosyloxyflavone. It is functionally related to an apigenin. It is a conjugate acid of an apiin(1-). Apiin is a natural product found in Crotalaria micans, Limonium axillare, and other organisms with data available. See also: Chamomile (part of); Chamaemelum nobile flower (part of). A beta-D-glucoside having a beta-D-apiosyl residue at the 2-position and a 5,4-dihydroxyflavon-7-yl moiety at the anomeric position. Apiin, a major constituent of Apium graveolens leaves with anti-inflammatory properties. Apiin shows significant inhibitory activity on nitrite (NO) production (IC50 = 0.08 mg/mL) in-vitro and iNOS expression (IC50 = 0.049 mg/ mL) in LPS-activated J774.A1 cells[1]. Apiin, a major constituent of Apium graveolens leaves with anti-inflammatory properties. Apiin shows significant inhibitory activity on nitrite (NO) production (IC50 = 0.08 mg/mL) in-vitro and iNOS expression (IC50 = 0.049 mg/ mL) in LPS-activated J774.A1 cells[1].

   

Caffeate

(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C9H8O4 (180.0422568)


D020011 - Protective Agents > D000975 - Antioxidants KEIO_ID C107 Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

Caffeic Acid

3,4-dihydroxy cinnamic acid

C9H8O4 (180.0422568)


A hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. 3,4-dihydroxycinnamic acid, also known as caffeic acid or trans-caffeate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3,4-dihydroxycinnamic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxycinnamic acid can be found in fats and oils and nuts, which makes 3,4-dihydroxycinnamic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxycinnamic acid exists in all eukaryotes, ranging from yeast to humans. Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal components of plant biomass and its residues . Caffeic acid is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food. (PMID:16870009) [HMDB]. Caffeic acid is found in many foods, some of which are cardoon, coriander, common persimmon, and irish moss. D020011 - Protective Agents > D000975 - Antioxidants Annotation level-2 CONFIDENCE standard compound; INTERNAL_ID 167 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.412 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.403 Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

ch3cho

Acetaldehyde [UN1089] [Flammable liquid]

C2H4O (44.0262134)


The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.

   

Thymol

InChI=1\C10H14O\c1-7(2)9-5-4-8(3)6-10(9)11\h4-7,11H,1-3H

C10H14O (150.1044594)


Thymol, also known as 1-hydroxy-5-methyl-2-isopropylbenzene or 2-isopropyl-5-methylphenol, is a member of the class of compounds known as aromatic monoterpenoids. Aromatic monoterpenoids are monoterpenoids containing at least one aromatic ring. Thus, thymol is considered to be an isoprenoid lipid molecule. Thymol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Thymol can be synthesized from p-cymene. Thymol can also be synthesized into thymol sulfate and thymol sulfate(1-). Thymol is a camphor, herbal, and medicinal tasting compound and can be found in a number of food items such as anise, common oregano, caraway, and highbush blueberry, which makes thymol a potential biomarker for the consumption of these food products. Thymol can be found primarily in saliva and urine, as well as in human liver and skeletal muscle tissues. Thymol exists in all eukaryotes, ranging from yeast to humans. C254 - Anti-Infective Agent > C28394 - Topical Anti-Infective Agent D000890 - Anti-Infective Agents > D000935 - Antifungal Agents Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1]. Thymol is the main monoterpene phenol occurring in essential oils isolated from plants belonging to the Lamiaceae family, and other plants such as those belonging to the Verbenaceae, Scrophulariaceae, Ranunculaceae and Apiaceae families. Thymol has antioxidant, anti-inflammatory, antibacterial and antifungal effects[1].

   

(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(5-isopropyl-2-methylphenoxy)tetrahydro-2H-pyran-3,4,5-triol

(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(5-isopropyl-2-methylphenoxy)tetrahydro-2H-pyran-3,4,5-triol

C16H24O6 (312.1572804)


   

cosmetin

5-hydroxy-2-(4-hydroxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromenone

C21H20O10 (432.105642)


Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

   

AI3-63211

InChI=1\C9H8O4\c10-7-3-1-6(5-8(7)11)2-4-9(12)13\h1-5,10-11H,(H,12,13)\b4-2

C9H8O4 (180.0422568)


D020011 - Protective Agents > D000975 - Antioxidants Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

Antioxine

InChI=1\C10H14O\c1-7(2)9-5-4-8(3)10(11)6-9\h4-7,11H,1-3H

C10H14O (150.1044594)


COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Carvacrol is a monoterpenoid phenol isolated from Thymus mongolicus Ronn., with antioxidant, anti-inflammatory and anticancer properties. Carvacrol causes cell cycle arrest in G0/G1, downregulates Notch-1, and Jagged-1, and induces apoptosis[1]. Carvacrol is a monoterpenoid phenol isolated from Thymus mongolicus Ronn., with antioxidant, anti-inflammatory and anticancer properties. Carvacrol causes cell cycle arrest in G0/G1, downregulates Notch-1, and Jagged-1, and induces apoptosis[1].

   

AIDS-026336

Benzenepropanoic acid, .alpha.-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-, (.alpha.R)-

C18H16O8 (360.0845136)


D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002491 - Central Nervous System Agents > D000700 - Analgesics D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively. Rosmarinic acid is a widespread phenolic ester compound in the plants. Rosmarinic acid inhibits MAO-A, MAO-B and COMT enzymes with IC50s of 50.1, 184.6 and 26.7 μM, respectively.

   

Isorhoifolin

5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one

C27H30O14 (578.163548)


Apigenin 8-c-rhamnosyl-glucoside, also known as isorhoifoline or apigenin-7-O-rutinoside, 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. Apigenin 8-c-rhamnosyl-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Apigenin 8-c-rhamnosyl-glucoside can be found in oat, which makes apigenin 8-c-rhamnosyl-glucoside a potential biomarker for the consumption of this food product. Isorhoifolin is found in citrus. Isorhoifolin is isolated from leaves of Citrus paradisi (grapefruit) and other plant species. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2]. Isorhoifolin is a flavonoid glycoside from Hemistepta lyrata. Isorhoifolin displays an anti-leakage effect[1][2].

   

7-MAG

3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]propanoic acid

C24H22O13 (518.1060362000001)


Apigenin 7-O-(6-malonyl-beta-D-glucoside) is a member of flavonoids and a glycoside. Apigenin 7-(6-malonylglucoside) is a natural product found in Monarda punctata and Cynara cardunculus with data available. Apigenin 7-O-malonylglucoside is found in chrysanthemum flowers[1].