NCBI Taxonomy: 751790

Clinopodium chilense (ncbi_taxid: 751790)

found 66 associated metabolites at species taxonomy rank level.

Ancestor: Clinopodium

Child Taxonomies: none taxonomy data.

Ursolic acid

(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


Ursolic 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. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663). Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane. Ursolic acid is a natural product found in Gladiolus italicus, Freziera, and other organisms with data available. Ursolic Acid is a pentacyclic triterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities. See also: Holy basil leaf (part of); Jujube fruit (part of); Lagerstroemia speciosa leaf (part of). D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent Found in wax of apples, pears and other fruits. V. widely distributed in plants D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

   

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].

   

Epicubenol

4,7-dimethyl-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-4a-ol

C15H26O (222.1983546)


1alpha-4-Cadinen-1-ol is found in cloves. 1alpha-4-Cadinen-1-ol is a constituent of oil of cubeb pepper (Piper cubeba). Constituent of cubeb pepper (Piper cubeba) oil. Epicubenol is found in herbs and spices.

   

Thymol

[5-methyl-2-(propan-2-yl)phenyl]oxidanesulfonic acid

C10H14O (150.1044594)


Thymol Sulfate is also known as Thymol sulfuric acid. Thymol Sulfate is considered to be practically insoluble (in water) and acidic. Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), C10H14O, is a natural monoterpenoid phenol derivative of p-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris (common thyme), ajwain,[4] and various other 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 is only slightly soluble in water at neutral pH, but it is extremely soluble in alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant (pKa) is 10.59±0.10.[5] Thymol absorbs maximum UV radiation at 274 nm.[6] Ancient Egyptians used thyme for embalming.[9] The ancient Greeks used it in their baths and burned it as incense in their temples, believing it was a source of courage. The spread of thyme throughout Europe was thought to be due to the Romans, as they used it to purify their rooms and to "give an aromatic flavour to cheese and liqueurs".[10] In the European Middle Ages, the herb was placed beneath pillows to aid sleep and ward off nightmares.[11] In this period, women also often gave knights and warriors gifts that included thyme leaves, because it was believed to bring courage to the bearer. Thyme was also used as incense and placed on coffins during funerals, because it was supposed to ensure passage into the next life.[12] The bee balms Monarda fistulosa and Monarda didyma, North American wildflowers, are natural sources of thymol. The Blackfoot Native Americans recognized these plants' strong antiseptic action and used poultices of the plants for skin infections and minor wounds. A tisane made from them was also used to treat mouth and throat infections caused by dental caries and gingivitis.[13] Thymol was first isolated by German chemist Caspar Neumann in 1719.[14] In 1853, French chemist Alexandre Lallemand[15] (1816-1886) named thymol and determined its empirical formula.[16] Thymol was first synthesized by Swedish chemist Oskar Widman[17] (1852-1930) in 1882.[18]

   

delta-Cadinol

(8R)-2,5-dimethyl-8-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-2-ol

C15H26O (222.1983546)


Delta-cadinol, also known as delta-cadinol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Delta-cadinol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Delta-cadinol is a herbal tasting compound and can be found in a number of food items such as cloves, parsley, lemon balm, and common sage, which makes delta-cadinol a potential biomarker for the consumption of these food products. Delta-cadinol, also known as δ-cadinol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Delta-cadinol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Delta-cadinol is a herbal tasting compound and can be found in a number of food items such as cloves, parsley, lemon balm, and common sage, which makes delta-cadinol a potential biomarker for the consumption of these food products.

   

Ursolic Acid

3-Hydroxy-12-ursen-28-oic acid

C30H48O3 (456.36032579999994)


Origin: Plant; SubCategory_DNP: Triterpenoids relative retention time with respect to 9-anthracene Carboxylic Acid is 1.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.640 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.638 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.642 Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

   

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].

   

epicubenol

4,7-dimethyl-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-4a-ol

C15H26O (222.1983546)


   

Urson

(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid

C30H48O3 (456.36032579999994)


D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

   
   

(5s,6s,7ar)-7a-hydroxy-3,3,6-trimethyl-6,7-dihydro-5h-1,2-benzodioxol-5-yl acetate

(5s,6s,7ar)-7a-hydroxy-3,3,6-trimethyl-6,7-dihydro-5h-1,2-benzodioxol-5-yl acetate

C12H18O5 (242.1154178)


   

(2r,3r,4as,4bs,7s,8ar,9s,10ar)-3-(acetyloxy)-7-ethenyl-2,8a-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-9-yl acetate

(2r,3r,4as,4bs,7s,8ar,9s,10ar)-3-(acetyloxy)-7-ethenyl-2,8a-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-9-yl acetate

C24H38O6 (422.2668248)


   

(1r,4r,4ar,8as)-1-isopropyl-4,7-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-4a-ol

(1r,4r,4ar,8as)-1-isopropyl-4,7-dimethyl-2,3,4,5,6,8a-hexahydro-1h-naphthalen-4a-ol

C15H26O (222.1983546)


   

(4as,4br,7s,8ar,9s,10as)-7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-2-oxo-octahydro-3h-phenanthren-9-yl acetate

(4as,4br,7s,8ar,9s,10as)-7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-2-oxo-octahydro-3h-phenanthren-9-yl acetate

C22H34O4 (362.24569640000004)


   

8a-hydroxy-4,7-dimethyl-5,6,7,8-tetrahydro-3h-1,2-benzodioxin-6-yl acetate

8a-hydroxy-4,7-dimethyl-5,6,7,8-tetrahydro-3h-1,2-benzodioxin-6-yl acetate

C12H18O5 (242.1154178)


   

(6r,7s,8ar)-8a-hydroxy-4,7-dimethyl-5,6,7,8-tetrahydro-3h-1,2-benzodioxin-6-yl acetate

(6r,7s,8ar)-8a-hydroxy-4,7-dimethyl-5,6,7,8-tetrahydro-3h-1,2-benzodioxin-6-yl acetate

C12H18O5 (242.1154178)


   

(1r,4r,4as,8as)-4-isopropyl-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalen-1-ol

(1r,4r,4as,8as)-4-isopropyl-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalen-1-ol

C15H26O (222.1983546)


   

(3bs,5ar,7s,9as,9bs)-7-ethenyl-7,9b-dimethyl-3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-5a-ol

(3bs,5ar,7s,9as,9bs)-7-ethenyl-7,9b-dimethyl-3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-5a-ol

C20H28O2 (300.2089188)


   

(3br,5ar,7s,9ar,9bs)-7-ethenyl-5a-hydroxy-7,9b-dimethyl-3h,3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-1-one

(3br,5ar,7s,9ar,9bs)-7-ethenyl-5a-hydroxy-7,9b-dimethyl-3h,3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-1-one

C20H28O3 (316.2038338)


   

3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydronaphtho[2,1-b]pyran-6a,10-diol

3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydronaphtho[2,1-b]pyran-6a,10-diol

C20H34O3 (322.25078140000005)


   

(3bs,5ar,7s,9as,9bs)-7-ethenyl-5a-hydroxy-7,9b-dimethyl-3h,3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-1-one

(3bs,5ar,7s,9as,9bs)-7-ethenyl-5a-hydroxy-7,9b-dimethyl-3h,3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-1-one

C20H28O3 (316.2038338)


   

3-(acetyloxy)-7-ethenyl-2,8a-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-9-yl acetate

3-(acetyloxy)-7-ethenyl-2,8a-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-9-yl acetate

C24H38O6 (422.2668248)


   

(2s,4as,4br,7s,8ar,9s,10as)-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-2-yl acetate

(2s,4as,4br,7s,8ar,9s,10as)-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-2-yl acetate

C22H36O4 (364.2613456)


   

(3r,4ar,6ar,10s,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydronaphtho[2,1-b]pyran-6a,10-diol

(3r,4ar,6ar,10s,10as,10br)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydronaphtho[2,1-b]pyran-6a,10-diol

C20H34O3 (322.25078140000005)


   

(3br,5ar,7s,9ar,9bs)-7-ethenyl-7,9b-dimethyl-3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-5a-ol

(3br,5ar,7s,9ar,9bs)-7-ethenyl-7,9b-dimethyl-3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-5a-ol

C20H28O2 (300.2089188)


   

7a-hydroxy-3,3,6-trimethyl-6,7-dihydro-5h-1,2-benzodioxol-5-yl acetate

7a-hydroxy-3,3,6-trimethyl-6,7-dihydro-5h-1,2-benzodioxol-5-yl acetate

C12H18O5 (242.1154178)


   

7-ethenyl-5a-hydroxy-7,9b-dimethyl-3h,3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-1-one

7-ethenyl-5a-hydroxy-7,9b-dimethyl-3h,3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-1-one

C20H28O3 (316.2038338)


   

7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-2-oxo-octahydro-3h-phenanthren-9-yl acetate

7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-2-oxo-octahydro-3h-phenanthren-9-yl acetate

C22H34O4 (362.24569640000004)


   

7-ethenyl-7,9b-dimethyl-3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-5a-ol

7-ethenyl-7,9b-dimethyl-3bh,4h,5h,6h,8h,9h,9ah,10h,11h-phenanthro[1,2-c]furan-5a-ol

C20H28O2 (300.2089188)


   

7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-2-yl acetate

7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-decahydrophenanthren-2-yl acetate

C22H36O4 (364.2613456)