Classification Term: 168601

Taraxastane, ursane and bauerane triterpenoids [PR010618] (ontology term: 89dd874cf29b30c501055485d1406ab5)

Taraxastane, ursane and bauerane triterpenoids [PR010618]

found 32 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.

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)


Maslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.; Maslinic 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. Maslinic 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. (PMID: 17292619) Maslinic 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. Maslinic 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. (PMID: 17292619). Maslinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. It has a role as an antioxidant, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a dihydroxy monocarboxylic acid. It derives from a hydride of an oleanane. Maslinic acid is a natural product found in Chaenomeles speciosa, Salvia tomentosa, and other organisms with data available. See also: Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. 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.

   

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.

   

Boswellic acid

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

C30H48O3 (456.36032579999994)


Boswellic acid (BA) is an active component of Boswellia serrata (also known as Salai guggul). Extensive research in the past 30 years identified the active component of this resin as BA (a pentacyclic triterpenic acid) and its derivatives (acetyl-beta-boswellic acid, 11-keto-beta-boswellic acid and acetyl-11-keto-beta-boswellic acid). In animal models of inflammation, BA has been shown to be an effective adjuvant mitigating bovine serum albumin-induced arthritis and osteoarthritis. The anti-arthritic potential of BA is a result of its anti-inflammatory activity, mediated through inhibition of NF-kB, COX-2 and 5-LOX. ((PMID: 17475558, 3429205). Boswellic acid is a triterpenoid. beta-Boswellic acid is a natural product found in Cyclocarya paliurus, Boswellia papyrifera, and other organisms with data available. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Boswellic acid is isolated from the gum resin of Boswellia serrata. β-Boswellic acid is a nonreducing-type inhibitor of the 5-lipoxygenase (5-LO) product formation either interacting directly with the 5-LO or blocking its translocation[1]. β-Boswellic acid inhibits the synthesis of DNA, RNA and protein in human leukemia HL-60 cells[2]. β-Boswellic acid is isolated from the gum resin of Boswellia serrata. β-Boswellic acid is a nonreducing-type inhibitor of the 5-lipoxygenase (5-LO) product formation either interacting directly with the 5-LO or blocking its translocation[1]. β-Boswellic acid inhibits the synthesis of DNA, RNA and protein in human leukemia HL-60 cells[2]. β-Boswellic acid is isolated from the gum resin of Boswellia serrata. β-Boswellic acid is a nonreducing-type inhibitor of the 5-lipoxygenase (5-LO) product formation either interacting directly with the 5-LO or blocking its translocation[1]. β-Boswellic acid inhibits the synthesis of DNA, RNA and protein in human leukemia HL-60 cells[2].

   

11-Keto-beta-boswellic acid

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

C30H46O4 (470.3395916)


11-Keto-beta-boswellic acid is a natural product found in Boswellia papyrifera, Boswellia sacra, and Boswellia serrata with data available. See also: Indian frankincense (part of). 11-Keto-beta-boswellic acid is found in herbs and spices. 11-Keto-beta-boswellic acid is a constituent of Boswellia serrata (Indian olibanum). Constituent of Boswellia serrata (Indian olibanum). 11-Keto-beta-boswellic acid is found in herbs and spices. 11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid) is a pentacyclic triterpenic acid of the oleogum resin from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. 11-Keto-beta-boswellic acid has the anti-inflammatory activity is primarily due to inhibit 5-lipoxygenase (5-LOX) and subsequent leukotriene and nuclear factor-kappa B (NF-κB) activation and tumor necrosis factor alpha generation production[1]. 11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid) is a pentacyclic triterpenic acid of the oleogum resin from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. 11-Keto-beta-boswellic acid has the anti-inflammatory activity is primarily due to inhibit 5-lipoxygenase (5-LOX) and subsequent leukotriene and nuclear factor-kappa B (NF-κB) activation and tumor necrosis factor alpha generation production[1]. 11-Keto-beta-boswellic acid (11-Keto-β-boswellic acid) is a pentacyclic triterpenic acid of the oleogum resin from the bark of the Boswellia serrate tree, popularly known as Indian Frankincense. 11-Keto-beta-boswellic acid has the anti-inflammatory activity is primarily due to inhibit 5-lipoxygenase (5-LOX) and subsequent leukotriene and nuclear factor-kappa B (NF-κB) activation and tumor necrosis factor alpha generation production[1].

   

Taraxasterol

(3S,4aR,6aR,6aR,6bR,8aR,12S,12aR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-ol

C30H50O (426.386145)


Taraxasterol is a pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3. It has a role as a metabolite and an anti-inflammatory agent. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of a taraxastane. Taraxasterol is a natural product found in Eupatorium altissimum, Eupatorium perfoliatum, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is taraxastane with a beta-hydroxy group at position 3. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1]. Taraxasterol is a pentacyclic triterpenoid isolated from Taraxacum mongolicum. Taraxasterol has a role as a metabolite and an anti-inflammatory agent[1].

   

A-beta-BA

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

C32H50O4 (498.37089000000003)


3-Acetyl-beta-boswellic acid is a natural product found in Boswellia sacra and Boswellia serrata with data available. 3-Acetyl-beta-boswellic acid is a boswellic acid isolated from Boswellia serrata gum resin[1]. 3-Acetyl-beta-boswellic acid is a boswellic acid isolated from Boswellia serrata gum resin[1].

   

AcKBA

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

C32H48O5 (512.3501557999999)


3-Acetyl-11-keto-beta-boswellic acid is a triterpenoid. 3-Acetyl-11-keto-beta-boswellic acid is a natural product found in Boswellia papyrifera, Boswellia sacra, and Boswellia serrata with data available. See also: Indian frankincense (part of). AKBA (Acetyl-11-keto-β-boswellic acid) is an active triterpenoid compound from the extract of Boswellia serrate and a novel Nrf2 activator. AKBA (Acetyl-11-keto-β-boswellic acid) is an active triterpenoid compound from the extract of Boswellia serrate and a novel Nrf2 activator. AKBA (Acetyl-11-keto-β-boswellic acid) is an active triterpenoid compound from the extract of Boswellia serrate and a novel Nrf2 activator.

   

3,4-seco-urs-20(30)-en-3-oic acid

3,4-seco-urs-20(30)-en-3-oic acid

C30H50O2 (442.38106)


   

Taraxastane-3beta,16beta,20beta-triol

Taraxastane-3beta,16beta,20beta-triol

C30H52O3 (460.3916242)


   

(+)-20-Taraxasten-3beta-ol

(+)-20-Taraxasten-3beta-ol

C30H50O (426.386145)


   

(+)-3beta-Hydroxy-ursan-28-oic acid

(+)-3beta-Hydroxy-ursan-28-oic acid

C30H50O3 (458.37597500000004)


   

(-)-Ilexol

(-)-7-baueren-3beta-ol

C30H50O (426.386145)


   

Pomolic acid

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

C30H48O4 (472.3552408)


Randialic acid A (Pomolic acid) is a pentacyclic triterpene isolated from?Euscaphis japonica?(Tunb.). Randialic acid A (Pomolic acid) inhibits tumor cells growth and induces cell apoptosis. Randialic acid A (Pomolic acid) has a potential for the treatment of prostate cancer (PC)[2]. Randialic acid A (Pomolic acid) is a pentacyclic triterpene isolated from?Euscaphis japonica?(Tunb.). Randialic acid A (Pomolic acid) inhibits tumor cells growth and induces cell apoptosis. Randialic acid A (Pomolic acid) has a potential for the treatment of prostate cancer (PC)[2].

   

Micromeric acid

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

C30H46O3 (454.34467659999996)


   

Actinidic acid

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

C30H46O5 (486.3345066)


A pentacyclic triterpenoid that is ursa-12,20(30)-diene substituted by a carboxy group at position 28 and hydroxy groups at positions 2, 3 and 23. It is a phytoalexin isolated from the peel of unripe kiwi fruit Actinidia deliciosa.

   

Carissic acid

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)


   

6beta-hydroxyasiatic acid

(4R)-2alpha,3beta,6beta,23-Tetrahydroxyurs-12-en-28-oic acid

C30H48O6 (504.3450708)


   

Maprounic acid

3beta-Hydroxyurs-12-en-29-oic acid

C30H48O3 (456.36032579999994)


A pentacyclic triterpenoid isolated from Maprounea africana and has been shown to exhibit inhibitory activity against HIV-1 reverse transcriptase.

   

Chletric acid

3beta,19alpha,23,24-tetrahydroxyurs-12-en-28-oic acid methyl ester

C31H50O6 (518.36072)


   

Sabiracin

11,25-epoxy-3beta-hydroxyurs-12-en-28-oic acid

C30H46O4 (470.3395916)


   

Carissin

3beta-hydroxy-27-m-methoxy-p-hydroxy-E-cinnamoyloxyurs-12-en-28-oic acid

C40H56O7 (648.4025826)


   

24-dimethoxy-3beta,6beta,19alpha-trihydroxyurs-12-en-28-oic acid

24-dimethoxy-3beta,6beta,19alpha-trihydroxyurs-12-en-28-oic acid

C32H52O7 (548.3712842)


   

Uncariursanic acid

3beta,6beta,19alpha-trihydroxy-urs-12-en-28-oic acid-24-carboxylic acid methyl ester

C31H48O7 (532.3399858)


   

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

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

C30H46O6 (502.3294216)


   

3beta,6beta,19alpha-trihydroxy-urs-12-en-28-oic acid

3beta,6beta,19alpha-trihydroxy-urs-12-en-28-oic acid

C30H48O5 (488.3501558)


   

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

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

C42H68O15 (812.4557978)


   

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

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

C42H68O16 (828.4507128)


   

Officinoterpenoside B

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

C42H68O15 (812.4557978)


   

Taraxastane-3beta,20beta,28-triol

Taraxastane-3beta,20beta,28-triol

C30H52O3 (460.3916242)


   

3-palmitoyl-taraxast-20-ene-3beta,16beta,22alpha-triol

3-palmitoyl-taraxast-20-ene-3beta,16beta,22alpha-triol

C46H80O4 (696.605628)


   

Salvurmin B

3-oxo-30-hydroxy-urs-1,9,12-triene

C30H44O2 (436.3341124)


   

Salvurmin A

1beta-hydroxy-3beta-acetoxy-17,22-secours-9,12,17(28)-triene-22-oic acid

C30H46O4 (470.3395916)