Two new ursane-type nortriterpenes from Lonicera macranthoides and their iNOS-inhibitory activities

Yu-Dan Mei; Nan Zhang; Wei-Yang Zhang; Jin-Shan Tang; Hua Zhou; Yang Yu; Xin-Sheng Yao

doi:10.1016/S1875-5364(19)30006-8

Two new ursane-type nortriterpenes from Lonicera macranthoides and their iNOS-inhibitory activities

Chin J Nat Med. 2019 Jan;17(1):27-32. doi: 10.1016/S1875-5364(19)30006-8.

Authors

Yu-Dan Mei¹, Nan Zhang², Wei-Yang Zhang³, Jin-Shan Tang⁴, Hua Zhou³, Yang Yu⁵, Xin-Sheng Yao⁶

Affiliations

¹ Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China; XiangXue Academician workstation, Xiangxue Pharmaceutical Co., Ltd., Guangzhou 510663, China.
² College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China.
³ Faculty of Chinese Medicine, Macau University of Science and Technology and State Key Laboratory of Quality Research in Chinese Medicine (Macau University of Science and Technology), Macau 999078, China.
⁴ Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China.
⁵ Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China. Electronic address: 1018yuyang@163.com.
⁶ Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, China; College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China. Electronic address: tyaoxs@jnu.edu.cn.

PMID: 30704620
DOI: 10.1016/S1875-5364(19)30006-8

Abstract

The flower buds of Lonicera macranthoides (Shan Yin-Hua), represent an important traditional Chinese medicine and food ingredient. A phytochemical investigation of the 70% EtOH extract of the flower buds of L. macranthoides resulted in the isolation of 12 triterpenoids (1-12), including two new ursane-type nortriterpenes, 2α, 24-dihydroxy-23-nor-ursolic acid (1) and 2α, 4α-dihydroxy-23-nor-ursolic acid (2). Their structures were established by multiple spectroscopic methods and comparison with literature data. All isolated compounds were evaluated for their anti-inflammatory effects in LPS-activated RAW264.7 cells. Compounds 1 and 2 exhibited inhibitory effects on iNOS at the concentration of 30 μmol·L^-1.

Keywords: Anti-inflammation; Lonicera macranthoides; Lonicerae Flos; Ursane-type nortriterpenes; iNOS.

MeSH terms

Animals
Anti-Inflammatory Agents / chemistry
Anti-Inflammatory Agents / pharmacology
Drugs, Chinese Herbal / chemistry
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / pharmacology*
Ethanol / chemistry
Flowers / chemistry
Lonicera / chemistry*
Macrophages / drug effects
Macrophages / metabolism
Mice
Molecular Structure
Nitric Oxide / metabolism
Nitric Oxide Synthase Type II / antagonists & inhibitors*
Plant Extracts / chemistry
Plants, Edible / chemistry
RAW 264.7 Cells
Triterpenes / chemistry*
Triterpenes / pharmacology*
Ursolic Acid

Substances

Anti-Inflammatory Agents
Drugs, Chinese Herbal
Enzyme Inhibitors
Plant Extracts
Triterpenes
ursane
Nitric Oxide
Ethanol
Nitric Oxide Synthase Type II
Nos2 protein, mouse