Antibacterial sesquiterpenes from the stems and roots of Thuja sutchuenensis

Miaomiao Wang; Liyun Zhao; Kai Chen; Yaxuan Shang; Jiafeng Wu; Xueyin Guo; Yihong Chen; Hongxin Liu; Haibo Tan; Sheng-Xiang Qiu

doi:10.1016/j.bioorg.2020.103645

Antibacterial sesquiterpenes from the stems and roots of Thuja sutchuenensis

Bioorg Chem. 2020 Mar:96:103645. doi: 10.1016/j.bioorg.2020.103645. Epub 2020 Feb 1.

Authors

Miaomiao Wang¹, Liyun Zhao², Kai Chen³, Yaxuan Shang², Jiafeng Wu², Xueyin Guo², Yihong Chen⁴, Hongxin Liu², Haibo Tan⁵, Sheng-Xiang Qiu⁶

Affiliations

¹ Program of Natural Product Medicinal Chemistry, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
² Program of Natural Product Medicinal Chemistry, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China.
³ State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, People's Republic of China; School of Materials Science and Engineering, Central South University of Forestry and Technology, Changsha 410004, People's Republic of China.
⁴ Guangzhou Green Health Biotechnology Co., Ltd., Guangzhou 510070, People's Republic of China.
⁵ Program of Natural Product Medicinal Chemistry, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China. Electronic address: tanhaibo@scbg.ac.cn.
⁶ Program of Natural Product Medicinal Chemistry, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, People's Republic of China. Electronic address: sxqiu@scbg.ac.cn.

PMID: 32036166
DOI: 10.1016/j.bioorg.2020.103645

Abstract

Eight new sesquiterpenes with diverse skeletons involving four cuparenes, denominated thujasutchins F-I (1-4), one eudesmane and one cedrol, named thujasutchin J (5) and thujasutchin K (6), as well as two thujopsenes thujasutchins L-M (7-8) together with three known congener compounds (9-11) were isolated from EtOAc soluble fraction of ethanolic extract of the stems and roots of Thuja sutchuenensis. Their structures including absolute configurations were unambiguously established by extensive interpretation of the NMR and mass spectroscopic data, X-ray diffractions, and ECD measurements powered by molecular calculations. The biological assays disclosed that 5 and 9 displayed potent inhibitory effect against Staphylococcus. aureus (CMCC 26003), methicillin-resistant Staphylococcus aureus (JCSC 4744), Bacillus cereus (ATCC 10876), and Staphylococcus epidermidis (ATCC 12228) with MICs ranging from 6.25 to 25 μg/mL.

Keywords: Antibacterial activity; Chemical constituent; Sesquiterpene; Thuja sutchuenensis.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology*
Crystallography, X-Ray
Humans
Methicillin-Resistant Staphylococcus aureus / drug effects
Models, Molecular
Sesquiterpenes / chemistry*
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*
Staphylococcal Infections / drug therapy
Staphylococcus aureus / drug effects
Staphylococcus epidermidis / drug effects
Thuja / chemistry*

Substances

Anti-Bacterial Agents
Sesquiterpenes