Flueggenoids A - E, new dinorditerpenoids from Flueggea virosa

Xiao-Feng Wang; Fei-Fei Liu; Zhengdan Zhu; Qiang-Qiang Fang; Shi-Jin Qu; Weiliang Zhu; Li Yang; Jian-Ping Zuo; Chang-Heng Tan

doi:10.1016/j.fitote.2018.12.025

Flueggenoids A - E, new dinorditerpenoids from Flueggea virosa

Fitoterapia. 2019 Mar:133:96-101. doi: 10.1016/j.fitote.2018.12.025. Epub 2018 Dec 31.

Authors

Xiao-Feng Wang¹, Fei-Fei Liu², Zhengdan Zhu³, Qiang-Qiang Fang¹, Shi-Jin Qu⁴, Weiliang Zhu⁵, Li Yang⁶, Jian-Ping Zuo⁷, Chang-Heng Tan⁸

Affiliations

¹ Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; School of Pharmacy, University of Chinese Academy of Sciences, Beijing 100049, China.
² Laboratory of Immunopharmacology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; School of Pharmacy, University of Chinese Academy of Sciences, Beijing 100049, China.
³ Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; School of Pharmacy, University of Chinese Academy of Sciences, Beijing 100049, China.
⁴ Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁵ Key Laboratory of Receptor Research, Drug Discovery and Design Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁶ Laboratory of Immunopharmacology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. Electronic address: yangli@simm.ac.cn.
⁷ Laboratory of Immunopharmacology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
⁸ Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. Electronic address: chtan@simm.ac.cn.

PMID: 30605781
DOI: 10.1016/j.fitote.2018.12.025

Abstract

A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A - E (1-5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6-16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.

Keywords: 13-Methyl-ent-podocarpane; Anti-HCV; Flueggea virosa; Securinega alkaloids; TDDFT ECD.

MeSH terms

Cell Line, Tumor
China
Hepacivirus
Humans
Malpighiales / chemistry*
Molecular Structure
Phytochemicals / chemistry
Phytochemicals / isolation & purification
Plant Components, Aerial / chemistry
Terpenes / chemistry*
Terpenes / isolation & purification

Substances

Phytochemicals
Terpenes