| Identification | Back Directory | [Name]
bryonolic acid | [CAS]
24480-45-3 | [Synonyms]
Bryolic acid
bryonolic acid
UNII-J7YR6A878I
3beta-Hydroxy-D-C-friedoolean-8-en-29-oic acid
(20R)-3β-Hydroxy-D:C-friedoolean-8-en-29-oic acid
D:C-Friedoolean-8-en-29-oic acid, 3-hydroxy-, (3beta,20beta)-
26-Norolean-8-en-29-oicacid, 3-hydroxy-13-methyl-, (3b,13a,14b,20b)-
26-Norolean-8-en-29-oic acid, 3-hydroxy-13-methyl-, (3β,13α,14β,20β)- | [Molecular Formula]
C30H48O3 | [MDL Number]
MFCD20260609 | [MOL File]
24480-45-3.mol | [Molecular Weight]
456.71 |
| Chemical Properties | Back Directory | [Melting point ]
303.5 °C | [Boiling point ]
553.3±50.0 °C(Predicted) | [density ]
1.10±0.1 g/cm3(Predicted) | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
4.79±0.70(Predicted) | [color ]
White to off-white | [LogP]
8.404 (est) |
| Hazard Information | Back Directory | [Uses]
Bryonolic acid is an active triterpenoid compound with immunomodulatory, anti-inflammatory, antioxidant and anticancer activities[1][2][3]. | [Definition]
ChEBI: 20-epi-bryonolic acid is a pentacyclic triterpenoid of D:C-friedooleanane-type triterpenoids isolated from the stems of Lagenaria siceraria and roots of Coriaria intermedia and has been found to exhibit antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. | [in vivo]
Bryonolic acid (500 mg/kg; i.p.; once) potently induces HO-1 in a manner dependent on the Nrf2-Keap1 pathway[3]. | Animal Model: | Wild-type and Nrf2-/- mice[3] | | Dosage: | 500 mg/kg
| | Administration: | i.p.; once | | Result: | Induced HO-1 in a manner dependent on the Nrf2-Keap1 pathway. |
| [target]
NO | NOS | HO-1 | Nrf2 | cAMP | Calcium Channel | Bcl-2/Bax | [References]
[1] Pornpatsorn Lertphadungkit, et al. Enhanced Production of Bryonolic Acid in Trichosanthes cucumerina L. (Thai Cultivar) Cell Cultures by Elicitors and Their Biological Activities. Plants (Basel). 2020 Jun 2;9(6):709. DOI:10.3390/plants9060709
[2] Farid Khallouki, et al. Bryonolic Acid Blocks Cancer Cell Clonogenicity and Invasiveness through the Inhibition of Fatty Acid: Cholesteryl Ester Formation. Biomedicines. 2018 Feb 12;6(1):21. DOI:10.3390/biomedicines6010021
[3] Tonibelle N Gatbonton-Schwager , et al. Bryonolic acid transcriptional control of anti-inflammatory and antioxidant genes in macrophages in vitro and in vivo. J Nat Prod. 2012 Apr 27;75(4):591-8. DOI:10.1021/np200823p |
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