bryonolic acid
bryonolic acid Basic information
- Product Name:
- bryonolic acid
- Synonyms:
-
- (20R)-3β-Hydroxy-D:C-friedoolean-8-en-29-oic acid
- 3beta-Hydroxy-D-C-friedoolean-8-en-29-oic acid
- D:C-Friedoolean-8-en-29-oic acid, 3-hydroxy-, (3beta,20beta)-
- Bryolic acid
- bryonolic acid
- 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)-
- UNII-J7YR6A878I
- CAS:
- 24480-45-3
- MF:
- C30H48O3
- MW:
- 456.71
- Mol File:
- 24480-45-3.mol
bryonolic acid Chemical Properties
- 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)
bryonolic acid Usage And Synthesis
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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