Pallamins A-C, ent-labdane and pallavicinin based dimers from the Chinese liverwort Pallavicinia ambigua (mitt.) stephani

Yi Li; Xiao-Bin Li; Jin-Chuan Zhou; Ze-Jun Xu; Ming-Zhu Zhu; Yan Zong; Jiao-Zhen Zhang; Jing-Jing Han; Ya-Jie Tang; Hong-Xiang Lou

doi:10.1016/j.phytochem.2023.113702

Pallamins A-C, ent-labdane and pallavicinin based dimers from the Chinese liverwort Pallavicinia ambigua (mitt.) stephani

Phytochemistry. 2023 Aug:212:113702. doi: 10.1016/j.phytochem.2023.113702. Epub 2023 May 4.

Authors

Yi Li¹, Xiao-Bin Li², Jin-Chuan Zhou³, Ze-Jun Xu⁴, Ming-Zhu Zhu⁴, Yan Zong⁴, Jiao-Zhen Zhang⁴, Jing-Jing Han⁴, Ya-Jie Tang⁵, Hong-Xiang Lou⁶

Affiliations

¹ Department of Natural Product Chemistry, Key Lab of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan, 250012, PR China; Department of Central Laboratory, Shandong Provincial Hospital Affiliated to Shandong First Medical University, No. 324 Jingwu Road, Jinan, 250021, PR China.
² Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), No 28789 Jingshi Dong Road, Jinan, 250103, PR China.
³ School of Pharmacy, Linyi University, Linyi, 276000, PR China.
⁴ Department of Natural Product Chemistry, Key Lab of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan, 250012, PR China.
⁵ State Key Laboratory of Microbial Technology, Shandong University, Qingdao, 266237, PR China.
⁶ Department of Natural Product Chemistry, Key Lab of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan, 250012, PR China. Electronic address: [email protected].

PMID: 37149119
DOI: 10.1016/j.phytochem.2023.113702

Abstract

Three unprecedented ent-labdane and pallavicinin based dimers pallamins A-C formed via [4 + 2] Diels-Alder cycloaddition, together with eight biosynthetically related monomers were isolated from Pallavicinia ambigua. Their structures were determined by the extensive analysis of HRESIMS and NMR spectra. The absolute configurations of the labdane dimers were determined by single crystal X-ray diffraction of the homologous labdane units, and ¹³C NMR and ECD calculations. Moreover, a preliminary evaluation of the anti-inflammatory activities of the isolated compounds was performed using the zebrafish model. Three of the monomers demonstrated significant anti-inflammatory activity.

Keywords: Anti-inflammatory activity; Diterpene dimers; Pallavicinia ambigua; Pallaviciniaceae; Theoretical calculations; [4 + 2] diels-alder cycloaddition.

MeSH terms

Animals
China
Diterpenes* / chemistry
Diterpenes* / pharmacology
Hepatophyta* / chemistry
Molecular Structure
Zebrafish

Substances

Diterpenes
labdane
pallavicinin