NCBI Taxonomy: 1679376

Dichapetalum gelonioides (ncbi_taxid: 1679376)

found 36 associated metabolites at species taxonomy rank level.

Ancestor: Dichapetalum

Child Taxonomies: none taxonomy data.

Betulinic acid

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

C30H48O3 (456.36032579999994)


Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. Betulinic acid is a natural product found in Ficus auriculata, Gladiolus italicus, and other organisms with data available. Betulinic Acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal and brain tumor cells. A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. See also: Jujube fruit (part of); Paeonia lactiflora root (part of). Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53 A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Epibetulinic acid exhibits potent inhibitory effects on NO and prostaglandin E2 (PGE2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin with IC50s of 0.7 and 0.6 μM, respectively. Anti-inflammatory activity[1].

   

betulinic acid

betulinic acid

C30H48O3 (456.36032579999994)


Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].

   

Mairin

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid

C30H48O3 (456.36032579999994)


C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].

   

(3s,5r)-3-[(1r,2r,3r,5r,6r,9s,14r,15r,17r,18s,19s)-3,17-dihydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

(3s,5r)-3-[(1r,2r,3r,5r,6r,9s,14r,15r,17r,18s,19s)-3,17-dihydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

C38H50O6 (602.36072)


   

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18s,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18s,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

C38H48O5 (584.3501557999999)


   

(3s,5r)-3-[(1r,2r,3r,5r,6r,9s,14s,15r,17r,18s,19s)-3,17-dihydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

(3s,5r)-3-[(1r,2r,3r,5r,6r,9s,14s,15r,17r,18s,19s)-3,17-dihydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

C38H50O6 (602.36072)


   

(4r,4ar,5r,6as,6br,8ar,12ar,12bs,14ar,14bs)-5-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-3-one

(4r,4ar,5r,6as,6br,8ar,12ar,12bs,14ar,14bs)-5-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-3-one

C30H50O2 (442.38106)


   

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

C38H48O5 (584.3501557999999)


   

(4r,4as,5r,6as,6br,8ar,12ar,12bs,14ar,14bs)-5-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-3-one

(4r,4as,5r,6as,6br,8ar,12ar,12bs,14ar,14bs)-5-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-3-one

C30H50O2 (442.38106)


   

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18r,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18r,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

C38H50O5 (586.365805)


   

(4r,4as,5r,6as,6br,8as,12as,12bs,14ar,14bs)-5-hydroxy-8a-(hydroxymethyl)-4,4a,6b,11,11,12b,14a-heptamethyl-tetradecahydro-1h-picen-3-one

(4r,4as,5r,6as,6br,8as,12as,12bs,14ar,14bs)-5-hydroxy-8a-(hydroxymethyl)-4,4a,6b,11,11,12b,14a-heptamethyl-tetradecahydro-1h-picen-3-one

C30H50O3 (458.37597500000004)


   

(3s,5r)-3-[(1r,2r,3r,5r,6r,9s,14s,15r,17r,18s,19s)-3,17-dihydroxy-9-(4-methoxyphenyl)-2,6,14-trimethyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

(3s,5r)-3-[(1r,2r,3r,5r,6r,9s,14s,15r,17r,18s,19s)-3,17-dihydroxy-9-(4-methoxyphenyl)-2,6,14-trimethyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docos-11-en-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

C39H52O7 (632.3712842)


   

(3s,5r)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18s,19s)-3-hydroxy-9-(4-methoxyphenyl)-2,6,14-trimethyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]oxolan-2-one

(3s,5r)-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18s,19s)-3-hydroxy-9-(4-methoxyphenyl)-2,6,14-trimethyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]oxolan-2-one

C39H50O6 (614.3607199999999)


   

methyl (2s,4as,4br,8as,10as)-6-hydroxy-2,4a,8a-trimethyl-8-methylidene-7-oxo-3,4,4b,9,10,10a-hexahydro-1h-phenanthrene-2-carboxylate

methyl (2s,4as,4br,8as,10as)-6-hydroxy-2,4a,8a-trimethyl-8-methylidene-7-oxo-3,4,4b,9,10,10a-hexahydro-1h-phenanthrene-2-carboxylate

C20H28O4 (332.19874880000003)


   

(2s,4as,4br,8as,10as)-6-hydroxy-2,4a,8a-trimethyl-8-methylidene-7-oxo-3,4,4b,9,10,10a-hexahydro-1h-phenanthrene-2-carboxylic acid

(2s,4as,4br,8as,10as)-6-hydroxy-2,4a,8a-trimethyl-8-methylidene-7-oxo-3,4,4b,9,10,10a-hexahydro-1h-phenanthrene-2-carboxylic acid

C19H26O4 (318.1830996)


   

(2s,4as,4br,8as,10as)-7-hydroxy-2,4a,8,8a-tetramethyl-6-oxo-1,3,4,4b,5,9,10,10a-octahydrophenanthrene-2-carboxylic acid

(2s,4as,4br,8as,10as)-7-hydroxy-2,4a,8,8a-tetramethyl-6-oxo-1,3,4,4b,5,9,10,10a-octahydrophenanthrene-2-carboxylic acid

C19H28O4 (320.19874880000003)


   

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18r,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

(3s,5r)-3-[(1s,2r,3r,5r,6r,9s,14s,15r,18r,19s)-3-hydroxy-2,6,14-trimethyl-9-phenyl-8-oxahexacyclo[16.3.1.0¹,¹⁸.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹]docosa-11,16-dien-19-yl]-5-[(1e)-3-hydroxy-2-methylprop-1-en-1-yl]oxolan-2-one

C38H48O5 (584.3501557999999)