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Bryonolic acid

Names

[ CAS No. ]:
24480-45-3

[ Name ]:
Bryonolic acid

[Synonym ]:
(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-icosahydro-2-picenecarboxylic acid
(2S,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-icosahydropicene-2-carboxylic acid
(2S,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-icosahydro-2-picenecarboxylic acid
2-Picenecarboxylic acid, 1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-eicosahydro-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-, (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-
2-Picenecarboxylic acid, 1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-eicosahydro-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-, (2S,4aS,6aS,8aR,10S,12aS,14aS,14bR)-

Biological Activity

[Description]:

Bryonolic acid is an active triterpenoid compound with immunomodulatory, anti-inflammatory, antioxidant and anticancer activities[1][2][3].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Immunology/Inflammation >> NO Synthase
Research Areas >> Inflammation/Immunology
Research Areas >> Neurological Disease

[In Vitro]

Bryonolic acid exerts anti-allergic activity by inhibiting homologous passive cutaneous anaphylaxis and delayed hypersensitivity. Bryonolic acid reduces nitric oxide by suppressing inducible nitric oxide synthase expression, indicating anti-inflammatory activity[1]. In rat adrenal pheochromocytoma (PC12) cells, Bryonolic acid against N-methyl-D-aspartate (NMDA)-induced neurotoxicity, indicating it as a candidate neuroprotective agent for cerebral ischemic treatment[1]. Bryonolic acid (1-200 μM) inhibits acyl-coA: cholesterol acyl transferase (ACAT) activity in rat liver microsomes in a concentration-dependent manner, blocking the biosynthesis of the cholesterol fatty acid ester tumour promoter. Bryonolic acid inhibits ACAT in intact cancer cells with an IC50 of 12.6 µM[2]. Bryonolic acid inhibits both clonogenicity and invasiveness in MCF-7 MB-231, U87 and 3T3-EA cells[2].

[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.

[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.

[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.

[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.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
553.3±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C30H48O3

[ Molecular Weight ]:
456.700

[ Flash Point ]:
302.5±26.6 °C

[ Exact Mass ]:
456.360352

[ PSA ]:
57.53000

[ LogP ]:
8.99

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.557

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds