Identification and biomimetic synthesis of iphionanes and cyperanes from Artemisia hedinii and their anti-hepatic fibrosis activity.
10.1016/S1875-5364(25)60915-0
- Author:
Xiaofei LIU
1
;
Xing WANG
1
;
Chunping TANG
2
;
Changqiang KE
2
;
Bintao HU
3
;
Sheng YAO
4
;
Yang YE
5
Author Information
1. State Key Laboratory of Drug Research & Natural Products Research 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.
2. State Key Laboratory of Drug Research & Natural Products Research Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
3. State Key Laboratory of Drug Research & Natural Products Research Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. Electronic address: hubintao@simm.ac.cn.
4. State Key Laboratory of Drug Research & Natural Products Research 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; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan 528400, China. Electronic address: yaosheng@simm.ac.cn.
5. State Key Laboratory of Drug Research & Natural Products Research 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; School of Life Science and Technology, Shanghai Tech University, Shanghai 201210, China. Electronic address: yye@simm.ac.cn.
- Publication Type:Journal Article
- Keywords:
Anti-hepatic fibrosis;
Artemisia hedinii;
Biomimetic synthesis;
Cyperane;
Iphionane;
New skeleton
- MeSH:
Artemisia/chemistry*;
Sesquiterpenes/chemical synthesis*;
Molecular Structure;
Humans;
Liver Cirrhosis/genetics*;
Biomimetics;
Plant Extracts/pharmacology*
- From:
Chinese Journal of Natural Medicines (English Ed.)
2025;23(7):871-880
- CountryChina
- Language:English
-
Abstract:
Two novel skeleton sesquiterpenoids (1 and 6), along with four new iphionane-type sesquiterpenes (2-5) and six new cyperane-type sesquiterpenes (7-11), were isolated from the whole plant of Artemisia hedinii (A. hedinii). The two novel skeleton compounds (1 and 6) were derived from the decarbonization of iphionane and cyperane-type sesquiterpenes, respectively. Their structures were elucidated through a comprehensive analysis of spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and 1D and 2D nuclear magnetic resonance (NMR) spectra. The absolute configurations were determined using electronic circular dichroism (ECD) spectra, single-crystal X-ray crystallographic analyses, time-dependent density functional theory (TDDFT) ECD calculation, density functional theory (DFT) NMR calculations, and biomimetic syntheses. The biomimetic syntheses of the two novel skeletons (1 and 6) were inspired by potential biogenetic pathways, utilizing a predominant eudesmane-type sesquiterpene (A) in A. hedinii as the substrate. All compounds were evaluated in LX-2 cells for their anti-hepatic fibrosis activity. Compounds 2, 8, and 10 exhibited significant activity in downregulating the expression of α-smooth muscle actin (α-SMA), a protein involved in hepatic fibrosis.
