Planta Med 2012; 78(2): 172-176
DOI: 10.1055/s-0031-1280347
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Metabolites of the Mangrove Fungus Xylaria sp. BL321 from the South China Sea

Yong-Xiang Song1 , 3 , Jun Wang2 , Shi-Wu Li1 , Bin Cheng1 , Li Li4 , Bin Chen1 , Lan Liu1 , 3 , Yong-Cheng Lin1 , 3 , Yu-Cheng Gu5
  • 1School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou, P. R. China
  • 2School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, P. R. China
  • 3Guangdong Province Key Laboratory of Functional Molecules in Oceanic Microorganism, Bureau of Education of Guangdong, Guangzhou, P. R. China
  • 4Institute of Materia Medica, CAMS & PUMC, Beijing, P. R. China
  • 5Syngenta Jealott's Hill International Research Centre, Bracknell, Berkshire, UK
Further Information

Publication History

received August 24, 2010 revised September 20, 2011

accepted October 14, 2011

Publication Date:
14 November 2011 (online)

Abstract

Two new lactones, 1 and 2, together with five known compounds, 37, were isolated from the marine mangrove fungus Xylaria sp. BL321. Their structures were determined by comprehensive analysis of their MS and NMR spectroscopic data. The absolute configurations of 1 and 2 were established on the basis of electronic circular dichroism calculations. It was found that the exocyclic double bond of 1 rearranged into a cyclic double bond to form a new crystal compound (1a) in diluted NaOH solution. Compound 3 was isolated for the first time as a natural product; its absolute configuration was determined by single-crystal X-ray crystallography. Compounds 47 displayed cytotoxicity against human breast cancer cell lines MCF-7 and MDA-MB-435, while compounds 13 were inactive (IC50 > 50 µM).

Supporting Information

References

  • 1 McDonald L A, Barbieri L R, Bernan V S, Janso J, Lassota P, Garter G T. 07H239-A, a new cytotoxic eremophilane sesquiterpene from the marine-derived Xylariaceous fungus LL-07H239.  J Nat Prod. 2004;  67 1565-1567
  • 2 Pittayakhajonwut P, Usuwan A, Intaraudom C, Veeranondha S, Srikitikulchai P. Sesquiterpene lactone 12, 8-eudesmanolides from the fungus Xylaria ianthinovelutina.  Planta Med. 2009;  75 1431-1435
  • 3 Boonphong S, Kittakoop P, Isaka M, Pittayakhajonwut D, Tanticharoen M, Thebtaranonth Y. Multiplolides A and B, new antifungal 10-membered lactones from Xylaria multiplex.  J Nat Prod. 2001;  64 965-967
  • 4 Healy P C, Hocking A, Tran-Dinh N, Pitt J I, Shivas R G, Mitchell J K, Kotiw M, Davis R A. Xanthones from a microfungus of the genus Xylaria.  Phytochemistry. 2004;  65 2373-2378
  • 5 Aldridge D C, Turner W B. Structures of cytochalasins C and D.  J Chem Soc (C). 1969;  923-928
  • 6 Abate D, Abraham W R, Meyer H. Cytochalasins and phytotoxins from the fungus Xylarila obobata.  Phytochemistry. 1997;  44 1443-1448
  • 7 Lin Y C, Wu X Y, Feng S, Jiang G C, Luo J H, Zhou S N, Vrijmoed L L P, Jones E B G, Krohn K, Steingrçver K, Zsila F. Five unique compounds: xyloketals from mangrove fungus Xylaria sp. from the south China Sea Coast.  J Org Chem. 2001;  66 6252-6256
  • 8 Wu X Y, Liu X H, Lin Y C, Luo J H, She Z G, Li H J, Chan L W, Antus S, Kurtan T, Elsasser B, Krohn K. Xyloketal F: A strong L-calcium channel blocker from the mangrove fungus Xylaria sp. (#2508) from the South China Sea coast.  Eur J Org Chem. 2005;  4061-4064
  • 9 Wu X Y, Liu X H, Jiang G C, Lin Y C, Chan W, Vrijmoed L L P. Xyloketal G, a novel metabolite from the mangrove fungus Xylaria sp. 2508.  Chem Nat Compd. 2005;  41 27-29
  • 10 Liu X, Xu F, Zhang Y, Liu L, Huang H, Cai X, Lin Y, Chan W. Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508.  Russ Chem B. 2006;  6 1091-1092
  • 11 Lin Y, Wu X, Feng S, Jiang G, Zhou S, Vrijmoed L L P, Jones E B G. A novel N-cinnamoylcyclopeptide containing an allenic ether from the fungus Xylaria sp. (strain c2508) from the South China Sea.  Tetrahedron Lett. 2001;  42 449-451
  • 12 Huang H R, She Z G, Lin Y C, Vrijmoed L L P, Lin W H. Cyclic peptides from an endophytic fungus obtained from a mangrove leaf (Kandelia candel).  J Nat Prod. 2007;  70 1696-1699
  • 13 Wang S Y, Xu Z H, Mao W W, She Z G, Tan N, Li C R, Lin Y C. Four new aromatic allenic ethers from the fungus Xylaria sp. No. 2508.  Nat Prod Res. 2008;  22 612-617
  • 14 Xu F, Zhang Y, Wang J J, Pang J Y, Huang C H, Wu X Y, She Z G, Vrijmoed L L P, Jones E B G, Lin Y C. Benzofuran derivatives from the mangrove endophytic fungus Xylaria sp. (#2508).  J Nat Prod. 2008;  71 1251-1253
  • 15 Singh S B, Felock P, Hazuda D J. Chemical and enzymatic modifications of integric acid and HIV-1 integrase inhibitory activity.  Bioorg Med Chem Lett. 2000;  10 235-238
  • 16 Ahmad H, Snatzke G, Atta-ur-Rahman. The CD in situ complexation method as a tool for determination of absolute configurations of cottonogenic derivatives.  J Am Chem Soc. 1993;  115 12533-12544
  • 17 Gaussian03. Gaussian, Inc. Available at http://www.gaussian.com Accessed 2011

Prof. Dr. Lan Liu
Prof. Dr. Yong-Cheng Lin

School of Chemistry and Chemical Engineering
Sun Yat-sen University

135 Xingang West Road

Guangzhou 510275

P. R. China

Phone: +86 20 84 03 96 23

Fax: +86 20 84 03 96 23

Email: ceslyc@mail.sysu.edu.cn

Email: cesllan@mail.sysu.edu.cn