Diterpenes from buds of Wikstroemia chamaedaphne showing anti-hepatitis B virus activities

Shi-Fei Li; Ying-Ying Jiao; Zhi-Qiang Zhang; Jian-Bin Chao; Jie Jia; Xun-Long Shi; Li-Wei Zhang

doi:10.1016/j.phytochem.2018.01.021

Diterpenes from buds of Wikstroemia chamaedaphne showing anti-hepatitis B virus activities

Phytochemistry. 2018 Jul:151:17-25. doi: 10.1016/j.phytochem.2018.01.021. Epub 2018 Apr 6.

Authors

Shi-Fei Li¹, Ying-Ying Jiao², Zhi-Qiang Zhang³, Jian-Bin Chao⁴, Jie Jia³, Xun-Long Shi⁵, Li-Wei Zhang⁶

Affiliations

¹ Key Laboratory of Chemical Biology and Molecular Engineering of Education Ministry, Institute of Molecular Science, Shanxi University, Taiyuan, 030006, PR China. Electronic address: lisf@sxu.edu.cn.
² Key Laboratory of Chemical Biology and Molecular Engineering of Education Ministry, Institute of Molecular Science, Shanxi University, Taiyuan, 030006, PR China; College of Chemistry & Chemical Engineering, Shanxi University, Taiyuan, 030006, PR China.
³ Key Laboratory of Chemical Biology and Molecular Engineering of Education Ministry, Institute of Molecular Science, Shanxi University, Taiyuan, 030006, PR China.
⁴ Scientific Instrument Center, Shanxi University, Taiyuan, 030006, PR China.
⁵ Department of Biosynthetic Medicinal Chemistry, School of Pharmaceutical Sciences, Fudan University, Shanghai, 200032, PR China. Electronic address: xunlongshi@fudan.edu.cn.
⁶ Key Laboratory of Chemical Biology and Molecular Engineering of Education Ministry, Institute of Molecular Science, Shanxi University, Taiyuan, 030006, PR China. Electronic address: lwzhang@sxu.edu.cn.

PMID: 29631103
DOI: 10.1016/j.phytochem.2018.01.021

Abstract

Phytochemical study of the buds of Wikstroemia chamaedaphne Meisn. led to the isolation of seven previously undescribed diterpenes, including one tigliane diterpene (wikstchalide A), two daphnane diterpenes (wikstroelides W-X), and four lathyrane diterpenes (laurifoliosides A-B and 2-epi-laurifoliosides A-B), along with four known diterpenes. The structures of these compounds were established by extensive spectroscopic evidence and electronic circular dichroism (ECD) calculations. Wikstchalide A possesses a 5,6-epoxy ring in the tigliane skeleton. Two compounds exhibited potential anti-hepatitis B virus activities, with IC₅₀ values of 46.5 and 88.3 μg/mL against hepatitis B virus (HBV) surface antigen (HBsAg), and six compounds showed certain inhibitory effects on HBV-DNA replication with the inhibition ratios ranging from 2.0% to 33.0% at the concentrations ranging from 0.39 to 6.25 μg/mL.

Keywords: Daphnane diterpene; Lathyrane diterpene; Thymelaeaceae; Tigliane diterpene; Wikstroemia chamaedaphne Meisn.; anti-Hepatitis B virus.

MeSH terms

Antiviral Agents / chemistry
Antiviral Agents / isolation & purification
Antiviral Agents / pharmacology*
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Dose-Response Relationship, Drug
Flowers / chemistry*
Hepatitis B virus / drug effects*
Microbial Sensitivity Tests
Molecular Conformation
Structure-Activity Relationship
Wikstroemia / chemistry*

Substances

Antiviral Agents
Diterpenes