A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar

Thae Thae San; Yue-Hu Wang; Dong-Bao Hu; Jun Yang; Dong-Dong Zhang; Meng-Yuan Xia; Xue-Fei Yang; Yong-Ping Yang

doi:10.1016/j.bmcl.2020.127682

A new sesquineolignan and four new neolignans isolated from the leaves of Piper betle, a traditional medicinal plant in Myanmar

Bioorg Med Chem Lett. 2021 Jan 1:31:127682. doi: 10.1016/j.bmcl.2020.127682. Epub 2020 Nov 15.

Authors

Thae Thae San¹, Yue-Hu Wang², Dong-Bao Hu³, Jun Yang², Dong-Dong Zhang², Meng-Yuan Xia⁴, Xue-Fei Yang⁵, Yong-Ping Yang⁶

Affiliations

¹ Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences, Yezin, Nay Pyi Taw 05282, Myanmar; Key Laboratory of Economic Plants and Biotechnology and the Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
² Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences, Yezin, Nay Pyi Taw 05282, Myanmar; Key Laboratory of Economic Plants and Biotechnology and the Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
³ School of Chemical Biology and Environment, Yuxi Normal University, Yuxi 653100, People's Republic of China.
⁴ Key Laboratory of Economic Plants and Biotechnology and the Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
⁵ Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences, Yezin, Nay Pyi Taw 05282, Myanmar; Key Laboratory of Economic Plants and Biotechnology and the Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China. Electronic address: [email protected].
⁶ Key Laboratory for Plant Diversity and Biogeography of East Asia, Institute of Tibetan Plateau Research at Kunming, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China. Electronic address: [email protected].

PMID: 33207281
DOI: 10.1016/j.bmcl.2020.127682

Abstract

One new sesquineolignan, piperneolignan A (1), four new neolignans, piperneolignans B-E (2-5), and eight known compounds were isolated from the leaves of Piper betle (Piperaceae) collected from Myanmar. These new structures were determined by analysis of MS and NMR data, and the absolute configuration of piperneolignan A was elucidated by electronic circular dichroism (ECD) calculations. Piperneolignan A (1), piperneolignan B (2), hydroxychavicol (6), p-hydroxycinnamaldehyde (10), and diallylcatechol (13) possessed anti-inflammatory activity against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells with IC₅₀ values of 9.87, 45.94, 4.80, 26.40, and 40.45 μM, respectively, compared with the positive control NG-monomethyl-l-arginine (l-NMMA, IC₅₀ = 33.84 μM). The two hydroxy groups in the structure of hydroxychavicol are essential for activity, and dimerization or trimerization of hydroxychavicol decreases activity.

Keywords: Anti-inflammatory; Myanmar; Neolignans; Piper betle; Piperaceae.

Publication types

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

MeSH terms

Animals
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Dose-Response Relationship, Drug
Lignans / chemistry
Lignans / isolation & purification
Lignans / pharmacology*
Lipopolysaccharides / antagonists & inhibitors*
Lipopolysaccharides / pharmacology
Medicine, Traditional
Mice
Molecular Structure
Myanmar
Nitric Oxide / antagonists & inhibitors*
Nitric Oxide / biosynthesis
Piper betle / chemistry*
Plant Leaves / chemistry
Plants, Medicinal / chemistry*
RAW 264.7 Cells
Structure-Activity Relationship

Substances

Anti-Inflammatory Agents, Non-Steroidal
Lignans
Lipopolysaccharides
Nitric Oxide