Two Enantiomeric Pairs of Meroterpenoids from Rhododendron capitatum

Hai-Bing Liao; Chun Lei; Li-Xin Gao; Jing-Ya Li; Jia Li; Ai-Jun Hou

doi:10.1021/acs.orglett.5b02515

Two Enantiomeric Pairs of Meroterpenoids from Rhododendron capitatum

Org Lett. 2015 Oct 16;17(20):5040-3. doi: 10.1021/acs.orglett.5b02515. Epub 2015 Oct 1.

Authors

Hai-Bing Liao¹, Chun Lei¹, Li-Xin Gao², Jing-Ya Li², Jia Li², Ai-Jun Hou¹

Affiliations

¹ Department of Pharmacognosy, School of Pharmacy, Fudan University , 826 Zhang Heng Road, Shanghai 201203, China.
² National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 189 Guo Shou Jing Road, Shanghai 201203, China.

PMID: 26426956
DOI: 10.1021/acs.orglett.5b02515

Abstract

Two enantiomeric pairs of meroterpenoids, (-)- and (+)-rhodonoids A (1a and 1b) and B (2a and 2b), were isolated unprecedentedly from partially racemic mixtures that naturally occurred in Rhododendron capitatum. Their structures were fully determined by spectroscopic data, X-ray crystallography, and electronic circular dichroism analysis. Compounds 1a and 1b are the first examples of meromonoterpenes featuring a unique 6/6/6/4 ring system. Compounds 2a and 2b showed PTP1B inhibitory activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Chromatography, High Pressure Liquid
Circular Dichroism
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Molecular Structure
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
Rhododendron / chemistry*
Stereoisomerism
Terpenes / chemistry
Terpenes / isolation & purification*
Terpenes / pharmacology

Substances

Terpenes
rhodonoid A
rhodonoid B
Protein Tyrosine Phosphatase, Non-Receptor Type 1