Practical Synthesis of α-Amyrin, β-Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase

Dongyin Chen; Fengguo Xu; Pu Zhang; Jie Deng; Hongbin Sun; Xiaoan Wen; Jun Liu

doi:10.1002/ardp.201700178

Practical Synthesis of α-Amyrin, β-Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase

Arch Pharm (Weinheim). 2017 Dec;350(12). doi: 10.1002/ardp.201700178. Epub 2017 Oct 13.

Authors

Dongyin Chen^{1

2}, Fengguo Xu¹, Pu Zhang¹, Jie Deng¹, Hongbin Sun¹, Xiaoan Wen¹, Jun Liu¹

Affiliations

¹ Jiangsu Key Laboratory of Drug Discovery for Metabolic Disease and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, China.
² Department of Medicinal Chemistry, School of Pharmacy, Nanjing Medical University, Nanjing, China.

PMID: 29027714
DOI: 10.1002/ardp.201700178

Abstract

A practical synthesis of α-amyrin (1), β-amyrin (2), and lupeol (3) was accomplished in total yields of 32, 42, and 40% starting from easily available ursolic acid (4), oleanolic acid (5), and betulin (6), respectively. Remarkably, these three natural pentacyclic triterpenes exhibited potential inhibitory activity against human oxidosqualene cyclase.

Keywords: Lupeol; Oxidosqualene cyclase inhibitor; Synthesis; α-Amyrin; β-Amyrin.

MeSH terms

Drug Design
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Humans
Intramolecular Transferases / antagonists & inhibitors*
Oleanolic Acid / analogs & derivatives*
Oleanolic Acid / chemical synthesis
Oleanolic Acid / chemistry
Oleanolic Acid / pharmacology
Pentacyclic Triterpenes / chemical synthesis*
Pentacyclic Triterpenes / chemistry
Pentacyclic Triterpenes / pharmacology

Substances

Enzyme Inhibitors
Pentacyclic Triterpenes
Oleanolic Acid
Intramolecular Transferases
lanosterol synthase
beta-amyrin
lupeol