Planta Med 2007; 73(5): 484-490
DOI: 10.1055/s-2007-967189
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

New Sesquiterpene Lactone and Neolignan Glycosides with Antioxidant and Anti-Inflammatory Activities from the Fruits of Illicium oligandrum

Wen-Zhao Tang1 , Yun-Bao Liu1 , Shi-Shan Yu1 , Jing Qu1 , Dong-Min Su1
  • 1Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, P. R. China
Further Information

Publication History

Received: November 11, 2006 Revised: February 27, 2007

Accepted: March 13, 2007

Publication Date:
26 April 2007 (online)

Abstract

Phytochemical investigations of the fruits of Illicium oligandrum resulted in a new sesquiterpene lactone, 3β-benzoyloxy-10-deoxyfloridanolide (1), and three new neolignan glycosides, including two dihydrobenzofuran neolignan glycosides, (7R,8S)-9-O-β-D-xylopyranosyl-9′-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (2) and (7R,8S)-9-O-shikimoyl-4-O-β-D-glucopyranosyldihydrodehydrodiconiferyl alcohol (3) and one 8-O-4′ neolignan glycoside, (7S,8R)-1-[4-O-(β-D-glucopyranosyl)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (4), together with three known sesquiterpene lactones (5 - 7) and two known neolignan glycosides (8 and 9). Their structures were elucidated on the basis of 1D, 2D NMR, HR-MS and chemical evidence. Compounds 3 and 4 showed moderate antioxidant activity with the inhibitory rates 13.30 % and 9.30 % at 1.0 × 10-5 M, respectively. Compounds 3 and 9 exhibited anti-inflammatory activity with the inhibitory rates 67.0 % and 51.0 % at 1.0 × 10-5 M, respectively.

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Shi-Shan Yu

Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine

Ministry of Education

Institute of Materia Medica

Chinese Academy of Medical Sciences and Peking Union Medical College

Beijing 100050

People’s Republic of China

Phone: +86-10-6316-5324

Fax: +86-10-6301-7757

Email: yushishan@imm.ac.cn