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Planta Med 2010; 76(5): 447-453
DOI: 10.1055/s-0029-1186221
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Acetogenin and Prenylated Flavonoids from Helminthostachys zeylanica with Inhibitory Activity on Superoxide Generation and Elastase Release by Neutrophils

Yuan-Chao Huang1 , Tsong-Long Hwang2 , Yu-Liang Yang3 , Shih-Hsiung Wu3 , Mei-Hua Hsu1 , Jih-Pyang Wang4 , Sheng-Chih Chen1 , Li-Jiau Huang1 , Chih-Chuang Liaw1 , 5
  • 1Graduate Institute of Pharmaceutical Chemistry, College of Pharmacy, China Medical University, Taichung, Taiwan
  • 2Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan, Taiwan
  • 3Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan
  • 4Department of Education and Research, Taichung Veterans General Hospital, Taichung, Taiwan
  • 5Department of Life Sciences, National Chung-Hsing University, Taichung, Taiwan
Further Information

Publication History

received April 9, 2009 revised Sept. 17, 2009

accepted Sept. 23, 2009

Publication Date:
20 October 2009 (online)

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Abstract

One new acetogenin, 6-hydroxy-8-pentadecyloxocane-2,7-dione (1), and four new prenylated flavonoids, 4′′a,5′′,6′′,7′′,8′′,8′′a-hexahydro-5,3′,4′-trihydroxy-5′′,5′′,8′′a-trimethyl-4H-chromeno[2′′,3′′:7,6]flavone (2), 4′′a,5′′,6′′,7′′,8′′,8′′a-hexahydro-5,3′,4′,‐trihydroxy-5′′,5′′,8′′a-trimethyl-4H-chromeno[2′′,3′′:7,8]flavone (3), 2-(3,4-dihydroxyphenyl)-6-((2,2-dimethyl-6-methylenecyclohexyl)methyl)-5,7-dihydroxy-chroman-4-one (4), and 2-(3,4-dihydroxy-2-[(2,6,6-trimethylcyclohex-2-enyl)methyl]phenyl)-3,5,7-trihydroxy-4H-chromen-4-one (5), together with six known compounds, were isolated and purified from the rhizomes of Helminthostachys zeylanica by column chromatography and high performance liquid chromatography (HPLC) via bioactivity-guided fractionation isolation. The structures of the new isolates were elucidated by spectroscopic methods. Compounds 1, 3, and 5 showed inhibitory activities on either superoxide anion generation or elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (FMLP/CB).

Key words

Helminthostachys zeylanica - Ophioglossaceae - acetogenin - prenylated flavonoids - superoxide generation - elastase release

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Dr. Chih-Chuang Liaw

Graduate Institute of Pharmaceutical Chemistry
College of Pharmacy
China Medical University

91 Hsueh-Shih Road

40402 Taichung

Taiwan

Phone: + 88 64 22 05 33 66 ext. 56 11

Fax: + 88 64 22 07 80 83

Email: Ccliaw@mail.cmu.edu.tw

    www.thieme-connect.de/ejournals/toc/plantamedica