Constituents from the leaves of Clausena lansium and their anti-inflammatory activity

De-Yang Shen; Ping-Chung Kuo; Shiow-Chyn Huang; Tsong-Long Hwang; Yu-Yi Chan; Po-Chuen Shieh; Nguyen Thi Ngan; Tran Dinh Thang; Tian-Shung Wu

doi:10.1007/s11418-016-1033-x

Constituents from the leaves of Clausena lansium and their anti-inflammatory activity

J Nat Med. 2017 Jan;71(1):96-104. doi: 10.1007/s11418-016-1033-x. Epub 2016 Aug 18.

Authors

De-Yang Shen¹, Ping-Chung Kuo¹, Shiow-Chyn Huang², Tsong-Long Hwang^{3

4

5}, Yu-Yi Chan⁶, Po-Chuen Shieh⁷, Nguyen Thi Ngan⁸, Tran Dinh Thang⁸, Tian-Shung Wu^{9

10}

Affiliations

¹ School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan, 701, Taiwan, ROC.
² Department of Pharmacy, Chia-Nan University of Pharmacy and Science, Tainan, 71710, Taiwan, ROC.
³ Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, 333, Taiwan, ROC.
⁴ Research Center for Industry of Human Ecology, Research Center for Chinese Herbal Medicine, and Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan, 333, Taiwan, ROC.
⁵ Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan, 333, Taiwan, ROC.
⁶ Department of Biotechnology, Southern Taiwan University of Science and Technology, Tainan, 71005, Taiwan.
⁷ Department of Pharmacy, Tajen University, Pingtung, 90741, Taiwan, ROC.
⁸ Department of Chemistry, Vinh University, Vinh City, Vietnam.
⁹ School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan, 701, Taiwan, ROC. tswu@mail.ncku.edu.tw.
¹⁰ Department of Pharmacy, Tajen University, Pingtung, 90741, Taiwan, ROC. tswu@mail.ncku.edu.tw.

PMID: 27539584
DOI: 10.1007/s11418-016-1033-x

Abstract

Five new acyclic amides, clausenalansamides C-G (1-5), clausenaline G (6) and (±)-5-(4-methylphenyl)-γ-valerolactone (7) reported from the natural source for the first time, were characterized from the leaves of Clausena lansium. Their structures were established by spectroscopic and spectrometric methods, and the absolute configurations of new compounds 1-5 were determined by electronic circular dichroism and single-crystal X-ray diffraction analyses. Eighteen compounds were evaluated for their anti-inflammatory activity and only imperatorin (11) and wampetin (12) displayed significant inhibition of fMLP/CB-induced superoxide anion generation with IC₅₀ values of 1.7 ± 0.3 and 6.8 ± 1.1 μM, respectively.

Keywords: Anti-inflammatory; Clausenalansamide; Electronic circular dichroism; Single-crystal X-ray diffraction analysis; Superoxide anion generation.

MeSH terms

Anti-Inflammatory Agents / chemistry*
Anti-Inflammatory Agents / pharmacology
Clausena / chemistry*
Molecular Structure
Plant Leaves / chemistry*

Substances

Anti-Inflammatory Agents