Classification Term: 168598

Oleanane triterpenoids [PR010615] (ontology term: c4ad1f5eecd3099f8fd957134b7cc31e)

Oleanane triterpenoids [PR010615]

found 61 associated metabolites at molecular_framework metabolite taxonomy ontology rank level.

Ancestor: C30 isoprenoids (triterpenes) [PR0106]

Child Taxonomies: There is no child term of current ontology term.

Glycyrrhetinic acid

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

C30H46O4 (470.3395916)


Glycyrrhetinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30. It has a role as an immunomodulator and a plant metabolite. It is a pentacyclic triterpenoid, a cyclic terpene ketone and a hydroxy monocarboxylic acid. It is a conjugate acid of a glycyrrhetinate. It derives from a hydride of an oleanane. Enoxolone (glycyrrhetic acid) has been investigated for the basic science of Apparent Mineralocorticoid Excess (AME). Enoxolone is a natural product found in Glycyrrhiza, Echinopora lamellosa, and other organisms with data available. Enoxolone is a pentacyclic triterpenoid aglycone metabolite of glycyrrhizin, which is a product of the plant Glycyrrhiza glabra (licorice), with potential expectorant, and gastrokinetic activities. After administration, enoxolone inhibits the metabolism of prostaglandins by both 15-hydroxyprostaglandin dehydrogenase [NAD(+)] and prostaglandin reductase 2. Therefore, this agent potentiates the activity of prostaglandin E2 and F2alpha, which inhibits gastric secretion while stimulating pancreatic secretion and the secretion of intestinal and respiratory mucus, leading to increased intestinal motility and antitussive effects. Additionally, this agent inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the conversion of cortisol to cortisone in the kidneys. An oleanolic acid from GLYCYRRHIZA that has some antiallergic, antibacterial, and antiviral properties. It is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation. See also: Glycyrrhizin (is active moiety of); Glycyrrhiza Glabra (part of). Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was first obtained from the herb liquorice. It is used in flavouring and it masks the bitter taste of drugs like aloe and quinine. It is effective in the treatment of peptic ulcer and also has expectorant (antitussive) properties (PMID:32106571). In glycyrrhetinic acid the functional group (R) is a hydroxyl group. Research in 2005 demonstrated that with a proper functional group a very effective glycyrrhetinic artificial sweetener can be obtained. When R is an anionic NHCO(CH2)CO2K side chain, the sweetening effect is found to 1200 times that of sugar (human sensory panel data). A shorter or longer spacer reduces the sweetening effect. One explanation is that the taste bud cell receptor has 1.3 nanometers (13 angstroms) available for docking with the sweetener molecule. In addition the sweetener molecule requires three proton donor positions of which two reside at the extremities to be able to interact efficiently with the receptor cavity. 18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2]. 18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2]. 18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhiza uralensis and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties. 18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhiza uralensis and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties.

   

Quillaic

(4aR,5R,6aS,6bR,8aR,9S,10S,12aR,12bR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid

C30H46O5 (486.3345066)


Quillaic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer). It has a role as an anti-inflammatory agent and a metabolite. It is a pentacyclic triterpenoid, a hydroxy monocarboxylic acid and an aldehyde. It is a conjugate acid of a quillate. It derives from a hydride of an oleanane. Quillaic acid is a natural product found in Silene firma, Gypsophila oldhamiana, and other organisms with data available. A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 3 and 16, an oxo group at position 23 and a carboxy group at position 28 (the 3beta,16alpha stereoisomer). Quillaic acid (Quillaja sapogenin) is a natural product used in pain relief research. Quillaic acid (Quillaja sapogenin) is a natural product used in pain relief research.

   

Oleanolic acid

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

C30H48O3 (456.36032579999994)


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

   

Gypsogenin

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

C30H46O4 (470.3395916)


Gypsogenin is a sapogenin that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3 and an oxo group at position 23. It is a pentacyclic triterpenoid, a sapogenin, an aldehyde and a monocarboxylic acid. It is functionally related to an oleanolic acid. It is a conjugate acid of a gypsogenin(1-). Gypsogenin is a natural product found in Silene firma, Gypsophila bicolor, and other organisms with data available. Gypsogenin shows antiangiogenic activity and the significant cytotoxicity against H460[1]. Gypsogenin shows antiangiogenic activity and the significant cytotoxicity against H460[1].

   

Gymnemic_acid

(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

C43H66O14 (806.4452336)


Gymnemic acid I is a triterpenoid saponin. Gymnemic acid I is a natural product found in Gymnema sylvestre with data available. Gymnemic acid I is a bioactive triterpene saponin found in Gymnema sylvestre. Gymnemic acid I decreases the apoptosis under the high glucose stress[1][2].

   

Amyrin

(3S,4aR,5R,6aR,6bR,8S,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-Octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydro-picen-3-ol

C30H50O (426.386145)


Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

   

Calenduloside E

(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

C36H56O9 (632.3924126000001)


Oleanolic acid 3-O-beta-D-glucosiduronic acid is a beta-D-glucosiduronic acid. It is functionally related to an oleanolic acid. Calenduloside E is a natural product found in Anredera baselloides, Polyscias scutellaria, and other organisms with data available. See also: Calendula Officinalis Flower (part of). Constituent of Calendula officinalis (pot marigold), Beta vulgaris (sugar beet) and Momordica cochinchinensis (Chinese cucumber). Oleanolic acid 3-glucuronide is found in common beet, green vegetables, and root vegetables. Calenduloside E is found in common beet. Calenduloside E is a constituent of Calendula officinalis (pot marigold), Beta vulgaris (sugar beet) and Momordica cochinchinensis (Chinese cucumber). Calenduloside E (CE) is a natural pentacyclic triterpenoid saponin extracted from Aralia elata. Calenduloside E (CE) has anti-apoptotic potent by targeting heat shock protein 90 (Hsp90)[1]. Calenduloside E (CE) is a natural pentacyclic triterpenoid saponin extracted from Aralia elata. Calenduloside E (CE) has anti-apoptotic potent by targeting heat shock protein 90 (Hsp90)[1].

   

Gypsogenin 3-O-rhamnosylglucuronide

28-hydroxy-23,28-dioxoolean-12-en-3beta-yl 3-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosiduronic acid

C42H64O14 (792.4295844)


   

3betaH-glycyrrhetinate

3alpha-hydroxy-11-oxoolean-12-en-30-oic acid

C30H46O4 (470.3395916)


   

3-Epioleanolic acid

(4aS,6aS,6bR,8aR,10R,12aR,12bR,14bS)-10-hydroxy-2,2,6a,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)


3-epioleanolic acid is a triterpenoid. It has a role as a metabolite. 3-Epioleanolic acid is a natural product found in Conandron ramondioides, Gardenia ternifolia, and other organisms with data available. 3-Epioleanolic acid is found in common sage. 3-Epioleanolic acid is isolated from sage Salvia officinalis and other plants. Isolated from sage Salvia officinalis and other plants. 3-Epioleanolic acid is found in common sage. A natural product found in Radermachera boniana. 3-Epioleanolic acid is an active component of Verbena officinalis Linn, with anti-inflammatory activity[1]. 3-Epioleanolic acid is an active component of Verbena officinalis Linn, with anti-inflammatory activity[1].

   

alpha-Boswellic acid

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

C30H48O3 (456.36032579999994)


alpha-Boswellic acid is a natural product found in Cyclocarya paliurus, Boswellia sacra, and other organisms with data available. alpha-Boswellic acid (α-Boswellic acid) is a pentacyclic triterpene compound from extracts of Frankincense, has anticonvulsant and anti-cancer properties[1]. alpha-Boswellic acid prevents and decreases the progression of Alzheimer’s hallmarks in vivo and can be used for Alzheimer’s disease research[2]. alpha-Boswellic acid (α-Boswellic acid) is a pentacyclic triterpene compound from extracts of Frankincense, has anticonvulsant and anti-cancer properties[1]. alpha-Boswellic acid prevents and decreases the progression of Alzheimer’s hallmarks in vivo and can be used for Alzheimer’s disease research[2]. alpha-Boswellic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=471-66-9 (retrieved 2024-08-21) (CAS RN: 471-66-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Bayogenin

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

C30H48O5 (488.3501558)


Bayogenin is a pentacyclic triterpenoid. It derives from a hydride of an oleanane. Bayogenin is a natural product found in Castanospermum australe, Phytolacca dodecandra, and other organisms with data available. Bayogenin is an alfalfa saponin, shows moderate potency of glycogen phosphorylase inhibition[1][2].

   

Medicagenic

(2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid

C30H46O6 (502.3294216)


Medicagenic acid is a triterpenoid. Medicagenic acid is a natural product found in Gladiolus italicus, Trigonella calliceras, and other organisms with data available. Medicagenic acid (Castanogenin) is isolated from the roots of Herniaria glabra, exhibits potent fungistatic effects against several plant pathogens and human dermatophytes[1]. Medicagenic acid (Castanogenin) has low enzyme inhibitory activities, the target enzymes are xanthine oxidase, collagenase, elastase, tyrosinase, ChE[2]. Medicagenic acid (Castanogenin) is isolated from the roots of Herniaria glabra, exhibits potent fungistatic effects against several plant pathogens and human dermatophytes[1]. Medicagenic acid (Castanogenin) has low enzyme inhibitory activities, the target enzymes are xanthine oxidase, collagenase, elastase, tyrosinase, ChE[2].

   

Glycyrrhizin

(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxy-tetrahydropyran-3-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

C42H62O16 (822.4037652)


Glycyrrhizinic acid is a triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid. It has a role as an EC 3.4.21.5 (thrombin) inhibitor and a plant metabolite. It is a glucosiduronic acid, a tricarboxylic acid, a pentacyclic triterpenoid, an enone and a triterpenoid saponin. It is a conjugate acid of a glycyrrhizinate(3-). Glycyrrhizic acid is extracted from the root of the licorice plant; Glycyrrhiza glabra. It is a triterpene glycoside with glycyrrhetinic acid that possesses a wide range of pharmacological and biological activities. When extracted from the plant, it can be obtained in the form of ammonium glycyrrhizin and mono-ammonium glycyrrhizin. Glycyrrhizic acid has been developed in Japan and China as a hepatoprotective drug in cases of chronic hepatitis. From January 2014, glycyrrhizic acid as part of the licorice extract was approved by the FDA as an existing food sweetener. It was approved by Health Canada to be used in over-the-counter products but all the products are currently on the status canceled post marketed. Glycyrrhizic acid is a natural product found in Hypomontagnella monticulosa, Abrus precatorius, and other organisms with data available. Glycyrrhizin is a saponin-like compound that provides the main sweet flavor for Glycyrrhiza glabra (licorice), with potential immunomodulating, anti-inflammatory, hepato- and neuro-protective, and antineoplastic activities. Glycyrrhizin modulates certain enzymes involved in inflammation and oxidative stress, and downregulates certain pro-inflammatory mediators, thereby protecting against inflammation- and reactive oxygen species (ROS)-induced damage. Glycerrhizin may also suppress the growth of susceptible tumor cells. Glycyrrhyzin is a metabolite found in or produced by Saccharomyces cerevisiae. A widely used anti-inflammatory agent isolated from the licorice root. It is metabolized to GLYCYRRHETINIC ACID, which inhibits 11-BETA-HYDROXYSTEROID DEHYDROGENASES and other enzymes involved in the metabolism of CORTICOSTEROIDS. Therefore, glycyrrhizic acid, which is the main and sweet component of licorice, has been investigated for its ability to cause hypermineralocorticoidism with sodium retention and potassium loss, edema, increased blood pressure, as well as depression of the renin-angiotensin-aldosterone system. See also: Enoxolone (has active moiety); Glycyrrhizinate Dipotassium (active moiety of); Glycyrrhiza uralensis Root (part of) ... View More ... A - Alimentary tract and metabolism > A05 - Bile and liver therapy > A05B - Liver therapy, lipotropics > A05BA - Liver therapy A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid. C1907 - Drug, Natural Product > C28269 - Phytochemical > C1905 - Triterpenoid Compound C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product D000893 - Anti-Inflammatory Agents Glycyrrhizic acid is a triterpenoid saponinl, acting as a direct HMGB1 antagonist, with anti-tumor, anti-diabetic activities. Glycyrrhizic acid is a triterpenoid saponinl, acting as a direct HMGB1 antagonist, with anti-tumor, anti-diabetic activities.

   

α-Boswellic acid

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

C30H48O3 (456.36032579999994)


alpha-Boswellic acid is a natural product found in Cyclocarya paliurus, Boswellia sacra, and other organisms with data available. alpha-Boswellic acid (α-Boswellic acid) is a pentacyclic triterpene compound from extracts of Frankincense, has anticonvulsant and anti-cancer properties[1]. alpha-Boswellic acid prevents and decreases the progression of Alzheimer’s hallmarks in vivo and can be used for Alzheimer’s disease research[2]. alpha-Boswellic acid (α-Boswellic acid) is a pentacyclic triterpene compound from extracts of Frankincense, has anticonvulsant and anti-cancer properties[1]. alpha-Boswellic acid prevents and decreases the progression of Alzheimer’s hallmarks in vivo and can be used for Alzheimer’s disease research[2].

   

Salaspermic acid

(3beta,20alpha)-3,24-epoxy-3-hydroxy-D:A-friedooleanan-29-oic acid

C30H48O4 (472.3552408)


A hexacyclic triterpenoid that is D:A-friedooleanan-29-oic acid substituted by a hydroxy group at position 3 and an epoxy group across positions 3 and 24 (the (3beta,20alpha stereoisomer). Isolated from Salacia macrosperma and Tripterygium wilfordii, it exhibits anti-HIV activity.

   

Maslinic Acid

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

C30H48O4 (472.3552408)


A pentacyclic triterpenoid that is 3alpha-hydroxy epimer of maslinic acid. Isolated from Prunella vulgaris and Isodon japonicus, it exhibits anti-inflammatory activity. Annotation level-1 Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation. Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation.

   

Gypsogenic acid

3beta-hydroxyolean-12-ene-23,28-dioic acid

C30H46O5 (486.3345066)


A pentacyclic triterpenoid that is olean-12-ene substituted by carboxy groups at positions 23 and 28 and a hydroxy group at position 3 (the 3beta stereoisomer).

   

Moronic acid

3-oxoolean-18-en-28-oic acid

C30H46O3 (454.34467659999996)


A pentacyclic triterpenoid that is olean-18-ene substituted at position 3 by an oxo group and position 28 by a carboxy group.

   

apoanagallosaponin IV

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-16alpha-acetoxy-3beta,22alpha,28-trihydroxyolean-12-ene

C54H88O23 (1104.5716098)


   

Enoxolone

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

C30H46O4 (470.3395916)


Glycyrrhetinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30. It has a role as an immunomodulator and a plant metabolite. It is a pentacyclic triterpenoid, a cyclic terpene ketone and a hydroxy monocarboxylic acid. It is a conjugate acid of a glycyrrhetinate. It derives from a hydride of an oleanane. Enoxolone (glycyrrhetic acid) has been investigated for the basic science of Apparent Mineralocorticoid Excess (AME). Enoxolone is a natural product found in Glycyrrhiza, Echinopora lamellosa, and other organisms with data available. Enoxolone is a pentacyclic triterpenoid aglycone metabolite of glycyrrhizin, which is a product of the plant Glycyrrhiza glabra (licorice), with potential expectorant, and gastrokinetic activities. After administration, enoxolone inhibits the metabolism of prostaglandins by both 15-hydroxyprostaglandin dehydrogenase [NAD(+)] and prostaglandin reductase 2. Therefore, this agent potentiates the activity of prostaglandin E2 and F2alpha, which inhibits gastric secretion while stimulating pancreatic secretion and the secretion of intestinal and respiratory mucus, leading to increased intestinal motility and antitussive effects. Additionally, this agent inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the conversion of cortisol to cortisone in the kidneys. An oleanolic acid from GLYCYRRHIZA that has some antiallergic, antibacterial, and antiviral properties. It is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation. See also: Glycyrrhizin (is active moiety of); Glycyrrhiza Glabra (part of). A pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30. D - Dermatologicals > D03 - Preparations for treatment of wounds and ulcers > D03A - Cicatrizants C471 - Enzyme Inhibitor > C54678 - Hydroxysteroid Dehydrogenase Inhibitor D000893 - Anti-Inflammatory Agents relative retention time with respect to 9-anthracene Carboxylic Acid is 1.588 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.587 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.585 18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2]. 18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2]. 18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhiza uralensis and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties. 18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhiza uralensis and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties.

   

9(11)-Dehydroglycyrrhetic acid

10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14b-octadecahydropicene-2-carboxylic acid

C30H46O3 (454.34467659999996)


Origin: Plant; SubCategory_DNP: Triterpenoids

   

Glycyrrhetinic Acid

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

C30H46O4 (470.3395916)


Origin: Plant; SubCategory_DNP: Triterpenoids 18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2]. 18α-Glycyrrhetinic acid, a diet-derived compound, is an inhibitor of NF-kB and an activator of proteasome, which serves as pro-longevity and anti-aggregation factor in a multicellular organism. 18α-Glycyrrhetinic acid induces apoptosis[1][2].

   

Protobassic acid

8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O6 (504.3450708)


A pentacyclic triterpenoid that is oleanolic acid substituted by hydroxy groups at positions 2, 6 and 23.

   

Arjunolic acid

(4aS,6aS,6bR,9R,10R,11R,12aR)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O5 (488.3501558)


   

Queretaroic acid

10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

C30H48O4 (472.3552408)


   

Bassic acid

10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a-carboxylic acid

C30H46O5 (486.3345066)


   

Bryonolic acid

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

C30H48O3 (456.36032579999994)


   

Katononic acid

2,4a,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

C30H46O3 (454.34467659999996)


   

Spinossaeure

3beta,19beta-dihydroxyolean-12-en-28-oic acid

C30H48O4 (472.3552408)


   

bayogenin 3-O-cellobioside

3beta-[O-beta-D-glucopyranosyl-(1->4)-beta-D-glucopyranosyloxy]-2beta,23-dihydroxyolean-12-en-28-oic acid

C42H68O15 (812.4557978)


A pentacyclic triterpenoid that is bayogenin substituted at the O-3 position by a cellobiosyl residue.

   

3-Oxoglycyrrhetinate

3,11-dioxoolean-12-en-30-oic acid

C30H44O4 (468.3239424)


   

11-Deoxoglycyrrhetinic acid

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

C30H48O3 (456.36032579999994)


   

16alpha-hydroxygypsogenic acidid

3beta,16alpha-dihydroxyolean-12-ene-23,28-dioic acid

C30H46O6 (502.3294216)


   

3,21-dioxoolean-18-en-28-oic acid

3,21-dioxoolean-18-en-28-oic acid

C30H44O4 (468.3239424)


A pentacyclic triterpenoid that is olean-18-ene substituted by a carboxy group at position 28 and oxo groups at positions 3 and 21 respectively. Isolated from the leaves of Acacia aulacocarpa, it exhibits inhibitory activity against Tie2 kinase (EC 2.7.10.1) as well as modest activity against a variety of cultured mammalian cells.

   

3-epikatonic acid

(20R)-3beta-Hydroxyolean-12-en-29-oic acid

C30H48O3 (456.36032579999994)


   

Acacic acid

3beta,16alpha,21beta-trihydroxyolean-12-en-28-oic acid

C30H48O5 (488.3501558)


A pentacyclic triterpenoid that is olean-12-ene substituted by carboxy group at position 28 and hydroxy groups at positions 3, 16 and 21 (the 3beta,16alpha,21beta stereoisomer).

   

Asprellic acid C

3-O-cis-p-coumaroyl-27-O-trans-p-coumaroyl-3beta,27-dihydroxy-olean-12-en-28-oic acid

C48H60O8 (764.428796)


A pentacyclic triterpenoid that is the diester obtained by the global condensation of the hydroxy groups of (3beta)-3,27-dihydroxyolean-12-en-28-oic acid with trans-4-coumaric acid and cis-4-coumaric acid respectively. It is isolated from the dried leaves of Ilex asprella and exhibits significant toxicity against KB (epidermoid carcinoma of the nasopharynx) and RPMI-7951 (melanoma) cell lines.

   

(20R)-3beta-hydroxy-D:C-friedoolean-7,9(11)-dien-29-oic acid

(20R)-3beta-hydroxy-D:C-friedoolean-7,9(11)-dien-29-oic acid

C30H46O3 (454.34467659999996)


   

quillaic acid alpha-L-Arap-(1->4)-alpha-L-Arap-(1->3)-beta-D-Xylp-(1->4)-alpha-L-Rhap-(1->2)-beta-D-fucopyranosyl ester

alpha-L-arabinopyranosyl-(1->4)-alpha-L-arabinopyranosyl-(1->3)-beta-D-xylopyranosyl-(1->4)-6-deoxy-alpha-L-mannopyranosyl-(1->2)-6-deoxy-1-O-[(3beta,16alpha)-3,16-dihydroxy-23,28-dioxoolean-12-en-28-yl]-beta-D-galactopyranose

C57H90O25 (1174.577089)


A triterpenoid saponin that is the pentasaccharide derivative of quillaic acid. Isolated from the roots of Gypsophila oldhamiana, it exhibits immunomodulatory activity.

   

3beta,19alpha,23-trihydroxy-6-oxo-olean-12-en-28-oic acid

3beta,19alpha,23-trihydroxy-6-oxo-olean-12-en-28-oic acid

C30H46O6 (502.3294216)


   

Cincholic acid

3beta-hydroxy-olean-12-en-27,28-dioic acid

C30H46O5 (486.3345066)


   

Cincholic acid 3beta-O-beta-D-fucopyranosyl-28-O-beta-D-glucopyranosyl ester

3beta-[O-beta-D-fucopyranosyl]-28-[O-beta-D-glucopyranosyloxy[-olean-12-en-27,28-dioic acid

C42H66O14 (794.4452336)


   

Cincholic acid 3beta-O-beta-D-glucopyranosyl-(1-4)-beta-D-fucopyranosyl-28-O-beta-D-glucopyranosyl ester

3beta-[O-beta-D-glucopyranosyl-(1-4)-beta-D-fucopyranosyl]-28-[O-beta-D-glucopyranosyloxy[-olean-12-en-27,28-dioic acid

C48H76O19 (956.4980545999999)


   

Cincholic acid 3beta-O-beta-D-glucopyranosyl-(1-4)-beta-D-fucopyranoside

3beta-[O-beta-D-glucopyranosyl-(1-4)-beta-D-fucopyranosyl]-olean-12-en-27,28-dioic acid

C42H66O14 (794.4452336)


   

2alpha,3beta,24-trihydroxyolean-12-en-28-oic acid 28-O-beta-d-glucopyranosyl-(1-2)-beta-d-glucopyranoside

2alpha,3beta,24-trihydroxyolean-12-en-28-oic acid 28-O-beta-d-glucopyranosyl-(1-2)-beta-d-glucopyranoside

C42H68O15 (812.4557978)


   

2alpha,3beta,19alpha,24-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-d-glucopyranosyl-(1-2)-beta-d-glucopyranoside

2alpha,3beta,19alpha,24-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-d-glucopyranosyl-(1-2)-beta-d-glucopyranoside

C42H68O16 (828.4507128)


   

Officinoterpenoside C

2alpha,3beta,24,29-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-d-glucopyranside

C37H60O11 (680.413541)


   

Brahucin A

1beta,3beta,24-trihydroxyolean-28,13beta-olide

C30H48O5 (488.3501558)


   

Brahucin B

1beta,3beta,23,24-trihydroxyolean-28,13beta-olide

C30H48O6 (504.3450708)


   

Arenaroside A

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-3beta,15alpha,16alpha,22alpha,28-pentahydroxyolean-12-ene

C52H86O23 (1078.5559606000002)


   

Arenaroside B

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-21beta,28-diacetoxy-3beta,15alpha,16alpha, 22alpha-tetrahydroxyolean-12-ene

C56H90O26 (1178.572004)


   

Arenaroside C

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-21beta,22alpha-diacetoxy-3beta,15alpha,16alpha,28-tetrahydroxyolean-12-ene

C56H90O26 (1178.572004)


   

Arenaroside D

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-22alpha-acetoxy-3beta,15alpha,16alpha,28-tetrahydroxyolean-12-ene

C54H88O24 (1120.5665248)


   

Arenaroside E

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-16alpha-acetoxy-3beta,15alpha,22alpha,28-tetrahydroxyolean-12-ene

C54H88O24 (1120.5665248)


   

Arenaroside F

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-28-acetoxy-3beta,15alpha,16alpha,22alpha-tetrahydroxyolean-12-ene

C54H88O24 (1120.5665248)


   

Arenaroside G

3-O-beta-d-glucopyranosyl-(1-2)-[beta-d-xylopyranosyl-(1-2)-beta-d-glucopyranosyl-(1-4)]-alpha-l-arabinopyranosyl-21beta,28-diacetoxy-3beta,15alpha,16alpha-trihydroxyolean-12-ene

C56H90O25 (1162.577089)


   

Recurvataside

3beta-glucopyranosyloxy-olean-13(18)-en-28-oic acid, 28 beta-D-glucopyranosyl ester

C42H68O13 (780.4659678)


   

delta-Oleanolic acid

Olean-13(18)-en-28-oic acid

C30H48O3 (456.36032579999994)


   
   

Momordin B

(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

C36H56O9 (632.3924126000001)


Oleanolic acid 3-O-beta-D-glucosiduronic acid is a beta-D-glucosiduronic acid. It is functionally related to an oleanolic acid. Calenduloside E is a natural product found in Anredera baselloides, Polyscias scutellaria, and other organisms with data available. See also: Calendula Officinalis Flower (part of). Calenduloside E (CE) is a natural pentacyclic triterpenoid saponin extracted from Aralia elata. Calenduloside E (CE) has anti-apoptotic potent by targeting heat shock protein 90 (Hsp90)[1]. Calenduloside E (CE) is a natural pentacyclic triterpenoid saponin extracted from Aralia elata. Calenduloside E (CE) has anti-apoptotic potent by targeting heat shock protein 90 (Hsp90)[1].