Sesquiterpenoids, phenolic and lignan glycosides from the roots and rhizomes of Clematis hexapetala Pall. and their bioactivities

Lu Cai; Si-Yuan Shao; Shao-Wei Han; Shuai Li

doi:10.1016/j.bioorg.2020.104312

Sesquiterpenoids, phenolic and lignan glycosides from the roots and rhizomes of Clematis hexapetala Pall. and their bioactivities

Bioorg Chem. 2020 Nov:104:104312. doi: 10.1016/j.bioorg.2020.104312. Epub 2020 Sep 24.

Authors

Lu Cai¹, Si-Yuan Shao¹, Shao-Wei Han¹, Shuai Li²

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, People's Republic of China.
² State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, People's Republic of China. Electronic address: [email protected].

PMID: 33142424
DOI: 10.1016/j.bioorg.2020.104312

Abstract

Approximately 17 compounds were isolated from a 60% EtOH aqueous extract of the roots and rhizomes of Clematis hexapetala Pall., including three new guaianolide sesquiterpenoids with 5/7/5-fused rings and 3S-configuration (1-3), five new prenylated tetra-substituted phenolic glycosides (4-8) with 6/6-fused 9H-benzopyran skeleton (5) and 6/7-fused 7,10-dihydro-benzoxepin skeleton (6-8), one new isoferulyl glucoside (9), two new furofuran lignan diglucosides (10-11), and six known compounds. The chemical structures of the new compounds were elucidated via spectroscopic data and electronic circular dichroism (ECD) analyses in combination with a modified Mosher's method. The possible biosynthetic relationships of prenylated tetra-substituted phenols were postulated. In the in vitro assays, compound 16 exhibited moderate TNF-α secretion inhibitory activity with IC₅₀ value of 3.419 μM. Compounds 14-16 displayed potent PTP1B enzymatic inhibitory activities with inhibition ratios of 48.30-86.00%. And compound 16 showed significant PTP1B enzymatic inhibition with IC₅₀ value of 4.623 μM.

Keywords: Anti-inflammatory activity; Clematis hexapetala Pall.; Guaianolide sesquiterpenoids; Lignan glycosides; PTP1B inhibition; Phenolic glycosides.

Publication types

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

MeSH terms

Animals
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / isolation & purification
Anti-Inflammatory Agents / pharmacology*
Clematis / chemistry*
Dose-Response Relationship, Drug
Glycosides / chemistry
Glycosides / isolation & purification
Glycosides / pharmacology*
Lignans / chemistry
Lignans / isolation & purification
Lignans / pharmacology*
Lipopolysaccharides / antagonists & inhibitors
Lipopolysaccharides / pharmacology
Mice
Molecular Structure
Nitric Oxide / antagonists & inhibitors
Nitric Oxide / biosynthesis
Phenols / chemistry
Phenols / isolation & purification
Phenols / pharmacology*
Plant Roots / chemistry
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
RAW 264.7 Cells
Rhizome / chemistry*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*
Structure-Activity Relationship
Tumor Necrosis Factor-alpha / antagonists & inhibitors
Tumor Necrosis Factor-alpha / biosynthesis

Substances

Anti-Inflammatory Agents
Glycosides
Lignans
Lipopolysaccharides
Phenols
Sesquiterpenes
Tumor Necrosis Factor-alpha
Nitric Oxide
Protein Tyrosine Phosphatase, Non-Receptor Type 1
Ptpn1 protein, mouse