13-Methyl-3,4-seco-ent-podocarpanes, rare C18-diterpenoids from the roots of Flueggea virosa

Chih-Hua Chao; Ju-Chien Cheng; De-Yang Shen; Hui-Chi Huang; Yang-Chang Wu; Tian-Shung Wu

doi:10.1039/C6RA00843G

13-Methyl-3,4-seco-ent-podocarpanes, rare C18-diterpenoids from the roots of Flueggea virosa†

Chih-Hua Chao,*^ab Ju-Chien Cheng,^c De-Yang Shen,^d Hui-Chi Huang,^e Yang-Chang Wu^abfg and Tian-Shung Wu*^dh

* Corresponding authors

^a School of Pharmacy, China Medical University, Taichung 40402, Taiwan
E-mail: chaochihhua@hotmail.com
Fax: +886-4-22078083
Tel: +886-4-22053366 ext. 5157

^b Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40402, Taiwan

^c Department of Medical Laboratory Science and Biotechnology, China Medical University, Taichung 40402, Taiwan

^d Department of Pharmacy, National Cheng Kung University, Tainan 70101, Taiwan
E-mail: tswu@mail.ncku.edu.tw
Fax: +886-6-2740552
Tel: +886-6-2757575 ext. 65333

^e Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 40402, Taiwan

^f Center for Molecular Medicine, China Medical University Hospital, Taichung 40447, Taiwan

^g Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 80708, Taiwan

^h Department of Pharmacy and Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 90741, Taiwan

Abstract

As a part of our continuing search for anti-HCV agents from a medicinal plant, Flueggea virosa, we identified fourteen new ingredients, including 13-methyl-3,4-seco-ent-podocarpanes (1–13) and a new naphthalene derivative (14). Their structures were determined by analysis of 2D NMR spectroscopic data, while their absolute configurations were determined by comparison of specific optical rotations with related analogues in the literature. The therapeutic potential against hepatitis C virus (HCV) infection was evaluated for the isolates. Compound 8 showed the most potent anti-HCV activity with a therapeutic index (TI = IC₅₀/EC₅₀) of 100.5.

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DOI: https://doi.org/10.1039/C6RA00843G
Article type: Paper
Submitted: 11 Jan 2016
Accepted: 14 Mar 2016
First published: 08 Apr 2016

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RSC Adv., 2016,6, 34708-34714

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13-Methyl-3,4-seco-ent-podocarpanes, rare C18-diterpenoids from the roots of Flueggea virosa

C. Chao, J. Cheng, D. Shen, H. Huang, Y. Wu and T. Wu, RSC Adv., 2016, 6, 34708 DOI: 10.1039/C6RA00843G

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13-Methyl-3,4-seco-ent-podocarpanes, rare C18-diterpenoids from the roots of Flueggea virosa†

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13-Methyl-3,4-seco-ent-podocarpanes, rare C18-diterpenoids from the roots of Flueggea virosa

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