Planta Med 2011; 77(15): 1735-1738
DOI: 10.1055/s-0030-1271040
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Two New Derivatives of Griseofulvin from the Mangrove Endophytic Fungus Nigrospora sp. (Strain No. 1403) from Kandelia candel (L.) Druce

Xuekui Xia1 , 2 , Qing Li1 , Jia Li1 , Changlun Shao1 , Jianye Zhang3 , Yonggang Zhang2 , Xin Liu2 , Yongcheng Lin1 , Changheng Liu2 , Zhigang She1
  • 1School of Chemistry and Chemical Engineering, Sun Yatsen University, Guangzhou, P. R. China
  • 2Key Laboratory for Applied Microbiology of Shandong Province, Biotechnology Center of the Shandong Academy of Sciences, Jinan, P. R. China
  • 3Research Department, Cancer Center, Sun Yatsen University, Guangzhou, Guangdong, P. R. China
Further Information

Publication History

received February 12, 2011 revised March 29, 2011

accepted March 31, 2011

Publication Date:
21 April 2011 (online)

Abstract

Two new compounds, methyl 3-chloro-6-hydroxy-2-(4-hydroxy-2-methoxy-6-methylphenoxy)-4-methoxybenzoate (1) and (2S,5′R,E)-7-hydroxy-4,6-dimethoxy-2-(1-methoxy-3-oxo-5-methylhex-1-enyl)-benzofuran-3(2H)-one (2), together with four known compounds, griseofulvin (3), dechlorogriseofulvin (4), bostrycin (5), and deoxybostrycin (6), were isolated from the marine endophytic fungus Nigrospora sp. (No. 1403) collected from the South China Sea. The structures were elucidated by spectroscopic methods, 1D, 2D NMR, and HREIMS. Compounds 5 and 6 showed moderate antitumor and moderate antimicrobial activity.

References

  • 1 Blunt J W, Copp B R, Hu W P, Munro M H G, Northcote P T, Prinsep M R. Marine natural products.  Nat Prod Rep. 2009;  26 170-244
  • 2 Prachya S, Wiyakrutta S, Sriubolmas N, Ngamrojanavanich N, Mahidol C, Ruchirawat S, Kittakoop P. Cytotoxic mycoepoxydiene derivatives from an endophytic fungus Phomopsis sp. isolated from Hydnocarpus anthelminthicus.  Planta Med. 2007;  73 1418-1420
  • 3 Wen L, Cai X L, Xu F, She Z G, Chan W L, Vrijmoed L L P, Jones E B G, Lin Y C. Three metabolites from the mangrove endophytic fungus Sporothrix sp. (#4335) from the South China Sea.  J Org Chem. 2009;  74 1093-1098
  • 4 Liu F, Cai X L, Yang H, Xia X K, Guo Z Y, Yuan J, Li M F, She Z G, Lin Y C. The bioactive metabolites of the mangrove endophytic fungus Talaromyces sp. ZH-154 isolated from Kandelia candel (L.) druce.  Planta Med. 2010;  76 185-189
  • 5 Xia X K, Huang H R, She Z G, Shao C L, Liu F, Cai X L, Vrijmoed L L P, Lin Y C. 1H and 13C NMR assignments for five anthraquinones from the mangrove endophytic fungus Halorosellinia sp. (No. 1403).  Magn Reson Chem. 2007;  45 777-780
  • 6 Mads H R, Pernille H, Charlotte H G, Thomas O L, Mads H C. Synthesis and single crystal X-ray analysis of two griseofulvin metabolites.  Tetrahedron Lett. 2010;  51 5881-5882
  • 7 Jarvis B B, Zhou Y, Jiang J, Wang S. Toxigenic molds in water-damaged buildings: Dechlorogriseofulvins from Memnoniella echinata.  J Nat Prod. 1996;  59 553-554
  • 8 Noda T, Take T, Miyauchi K, Watanabe T, Abe J. Structure of bostrycin.  Tetrahedron Lett. 1968;  6087-6090
  • 9 Noda T, Take T, Watanabe T, Abe J. The structure of bostrycin.  Tetrahedron. 1970;  26 1339-1346
  • 10 Charudattan R, Rao K V. Bostrycin and 4-deoxybostrycin: two nonspecific phytotoxins produced by Alternaria eichhorniaet.  Appl Environ Microbiol. 1982;  43 846-849
  • 11 Albert S, Unwin C H, Stothers J B. On the biosynthesis of some polyketide metabolites in Alternaria solani: 13C and 2HMR studies.  Can J Chem. 1983;  61 372-377
  • 12 Ge M H, Song Y C, Shan C Y, Ye Y H, Tan R X. New and cytotoxic anthraquinones from Pleospora sp. IFB-E006, an endophytic fungus in Imperata cylindrical.  Planta Med. 2005;  71 1063-1065
  • 13 Fromtling R A, Galgiani J N, Pfaller M A, Espinel-Ingroff A, Bartizal K F, Bartlett M S, Body B A, Frey C, Hall G, Roberts G D. Multicenter evaluation of a broth macrodilution antifungal susceptibility test for yeasts.  Antimicrob Agents Chemother. 1993;  37 39-45

Prof. Changheng Liu

Key Laboratory for Applied Microbiology of Shandong Province
Biotechnology Center of the Shandong Academy of Sciences

No. 19, Keyuan Road

Jinan 250014

P. R. China

Phone: +86/531/82605355

Fax: +86/531/82965634

Email: liuchh@keylab.net

Prof. Zhigang She

School of Chemistry and Chemical Engineering
Sun Yatsen University

No. 135, West Xingang Road

Guangzhou 510275

P. R. China

Phone: +86 20 84 03 40 96

Fax: +86 20 84 03 40 96

Email: cesshzhg@mail.sysu.edu.cn

>