β-Amyrenonol

Names

[ Name ]:
β-Amyrenonol

[Synonym ]:
β-Amyrenonol
Olean-12-en-11-one, 3-hydroxy-, (3β)-
b-Amyrenonol
(3β)-3-Hydroxyolean-12-en-11-one
11-oxo-β-amyrin

Biological Activity

[Description]:

β-Amyrenonol (11-Oxo-β-amyrin), an oleanolic-type triterpenoid in licorice roots, is a precursor of Glycyrrhetinic acid. β-Amyrenonol has anti-proliferative and anti-inflammatory activities, and β-Amyrenonol could function as the skeleton for the synthesis of many triterpenoids[1][2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Inflammation/Immunology

[In Vitro]

β-Amyrenonol (11-Oxo-β-amyrin) inhibits cell growth of HL60 cells with an IC50 value of 26.3 µM[1]. β-Amyrenonol (11-Oxo-β-amyrin) (100 μM) significantly reduces lipopolysaccharide-induced TNFα release in THP-1 cells[1]. CYP88D6 is characterized by in vitro enzymatic activity assays and shown to catalyze the sequential two-step oxidation of β-amyrin at C-11 to produce β-Amyrenonol (11-Oxo-β-amyrin). CYP88D6 coexpressed with β-amyrin synthase in yeast also catalyzed in vivo oxidation of β-amyrin to β-Amyrenonol[3].

[References]

[1]. James Reed, et al. A Translational Synthetic Biology Platform for Rapid Access to Gram-Scale Quantities of Novel Drug-Like Molecules. Metab Eng. 2017 Jul;42:185-193.

[2]. Ming Zhu, et al. Boosting 11-oxo-β-amyrin and Glycyrrhetinic Acid Synthesis in Saccharomyces Cerevisiae via Pairing Novel Oxidation and Reduction System From Legume Plants. Metab Eng. 2018 Jan;45:43-50.

[3]. Hikaru Seki, et al. Licorice Beta-Amyrin 11-oxidase, a Cytochrome P450 With a Key Role in the Biosynthesis of the Triterpene Sweetener Glycyrrhizin. Proc Natl Acad Sci U S A. 2008 Sep 16;105(37):14204-9.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
524.0±49.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₀H₄₈O₂

[ Molecular Weight ]:
440.701

[ Flash Point ]:
221.3±22.4 °C

[ Exact Mass ]:
440.365417

[ PSA ]:
37.30000

[ LogP ]:
8.61

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.545

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds

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