β-Amyrenonol

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.

Product information

CAS Number: 38242-02-3

Molecular Weight: 440.70

Formula: C30H48O2

Synonym:

11-Oxo-β-amyrin

Chemical Name: (4aR,6aS,6bR,8aR,10S,12aS,12bR,14bR)-8a,12b,14b-trihydrogenio-10-hydroxy-2,2,4a,6a,6b,9,9,12a-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicen-13-one

Smiles: C[C@@]12CC[C@@]3(C)CCC(C)(C)C[C@H]3C1=CC(=O)[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C

InChiKey: UKAIYBGRLWQHDQ-KWRVYEIKSA-N

InChi: InChI=1S/C30H48O2/c1-25(2)13-14-27(5)15-16-29(7)19(20(27)18-25)17-21(31)24-28(6)11-10-23(32)26(3,4)22(28)9-12-30(24,29)8/h17,20,22-24,32H,9-16,18H2,1-8H3/t20-,22-,23-,24+,27+,28-,29+,30+/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

β-Amyrenonol (11-Oxo-β-amyrin) inhibits cell growth of HL60 cells with an IC50 value of 26.3 µM. β-Amyrenonol (11-Oxo-β-amyrin) (100 μM) significantly reduces lipopolysaccharide-induced TNFα release in THP-1 cells. 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.

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.

Products are for research use only. Not for human use.