Sesquiterpenes from Chloranthus holostegius with anti-inflammatory activities

Huan Yan; Li-Li Xu; Xue-Fang Zheng; Xin-Feng Zou; Long-Gao Xiao; Yong-Sheng Zhou; Li He; Hai-Yang Liu

doi:10.1016/j.fitote.2023.105766

Sesquiterpenes from Chloranthus holostegius with anti-inflammatory activities

Fitoterapia. 2024 Jan:172:105766. doi: 10.1016/j.fitote.2023.105766. Epub 2023 Dec 4.

Authors

Huan Yan¹, Li-Li Xu², Xue-Fang Zheng², Xin-Feng Zou², Long-Gao Xiao³, Yong-Sheng Zhou³, Li He⁴, Hai-Yang Liu⁵

Affiliations

¹ State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Characteristic Plant Extraction Laboratory, Kunming 650106, China; University of Chinese Academy of Sciences, Beijing 100039, China; Yunnan Key Laboratory of Plant Reproductive Adaptation and Evolutionary Ecology and Centre for Invasion Biology, Institute of Biodiversity, School of Ecology and Environmental Science, Yunnan University, Kunming 650500, China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Characteristic Plant Extraction Laboratory, Kunming 650106, China.
³ State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Characteristic Plant Extraction Laboratory, Kunming 650106, China; University of Chinese Academy of Sciences, Beijing 100039, China.
⁴ Skin Health Research Center, Yunnan Characteristic Plant Extraction Laboratory, Kunming 650000, China; Department of Dermatology, The First Affiliated Hospital of Kunming Medical University, Kunming 650032, China.
⁵ State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China; Yunnan Characteristic Plant Extraction Laboratory, Kunming 650106, China. Electronic address: haiyangliu@mail.kib.ac.cn.

PMID: 38056697
DOI: 10.1016/j.fitote.2023.105766

Abstract

The phytoconstituents of the whole plants of Chloranthus holostegius were investigated. As a result, thirteen undescribed sesquiterpenes (chloranholosins A-M, 1-13), including ten acorane-type sesquiterpenes (1-10), one germacrene-type sesquiterpene (11), and two lindenane-type sesquiterpenes (12-13), together with fifteen known sesquiterpenes were isolated. Their structures and absolute configurations were elucidated by a comprehensive method including the spectroscopic data, electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction. Chloranholosin L (12) was elucidated as a rare lindenane-type sesquiterpene featuring 14α-Me and 5-OH moieties. And chloranholosin M (13) was the first lindenane-type sesquiterpene possessing β-cyclopropane, 14α-Me, and 5β-H configuration from the family Chloranthaceae. Furthermore, twelve new isolates and some known sesquiterpenes were evaluated for their inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophage cells. Among them, compounds 12, 16, and 23 showed comparable inhibitory activity to that of the positive control, with IC₅₀ values of 47.9, 41.5, and 48.3 μM, respectively.

Keywords: Anti-inflammatory activity; Chloranholosins A–M; Chloranthus holostegius; Sesquiterpenes.

MeSH terms

Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / pharmacology
Circular Dichroism
Magnoliopsida* / chemistry
Molecular Structure
Sesquiterpenes* / chemistry
Sesquiterpenes* / pharmacology

Substances

Sesquiterpenes
Anti-Inflammatory Agents