Planta Med 2010; 76(16): 1888-1891
DOI: 10.1055/s-0030-1249955
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Three Dimeric Naphtho-γ-Pyrones from the Mangrove Endophytic Fungus Aspergillus tubingensis Isolated from Pongamia pinnata

Hong-Bo Huang1 , Xiao-Jun Feng1 , Lan Liu1 , Bin Chen1 , Yong-Jun Lu2 , 3 , Lin Ma1 , Zhi-Gang She1 , 3 , Yong-Cheng Lin1 , 3
  • 1School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou, P. R. China
  • 2School of Life Sciences, Sun Yat-sen University, Guangzhou, P. R. China
  • 3Guangdong Province Key Laboratory of Functional Molecules in Oceanic Microorganism (Sun Yat-sen University), Bureau of Education of Guangdong, Guangzhou, P. R. China
Further Information

Publication History

received February 25, 2010 revised March 31, 2010

accepted April 20, 2010

Publication Date:
26 May 2010 (online)

Abstract

Three new dimeric naphtho-γ-pyrones, named rubasperone A (1), rubasperone B (2), and rubasperone C (3), together with two known compounds, rubrofusarin (4) and rubrofusarin B (5), were isolated from the mangrove endophytic fungus Aspergillus tubingensis (GX1-5E). Their structures were determined by spectroscopic methods, including IR, MS, and 1D and 2D NMR. The structures of 1 and 2 were further confirmed by X-ray crystallography. In the bioactivity assays against tyrosinase and α-glucosidase, rubrofusarin (4) exhibited moderate tyrosinase inhibitory activity, with an IC50 value of 65.6 µM, and rubasperone C (3) showed mild α-glucosidase inhibitory activity, with an IC50 value of 97.3 µM.

References

  • 1 Mincer T, Jensen P, Kauffman C, Fenical W. Widespread and persistent populations of a major new marine actinomycete taxon in ocean sediments.  Appl Environ Microbiol. 2002;  68 5005-5011
  • 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 Ma H Y, Song Y C, Mao Y Y, Jiang J H, Tan R X, Luo L. Endophytic fungalmetabolite fumigaclavine C causes relaxation of isolated rat aortic rings.  Planta Med. 2006;  72 87-92
  • 4 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, Steingrove 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
  • 5 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
  • 6 Pan J H, Jones E B G, She Z G, Pang J Y, Lin Y C. Review of bioactive compounds from fungi in the South China Sea.  Bot Mar. 2008;  51 179-190
  • 7 Liu F, Cai X L, Yang H, Xia X K, Guo Z Y, Yuan J, Li M F, She Z G, Lin Y C. Bioactive metabolites of the mangrove endophytic fungus Talaromyces sp. ZH-154 isolated from Kandelia candel (L.) Druce.  Planta Med. 2010;  76 185-189
  • 8 Akiyama K, Teraguchi S, Hamasaki Y, Mor M, Tatsum K, Ohnishi K, Hayashi H. New dimeric naphthopyrones from Aspergillus niger.  J Nat Prod. 2003;  66 136-139
  • 9 Campos F R, Barison A, Daolio C, Ferreira G A, Rodrigues-Fo E. Complete 1H and 13C NMR assignments of aurasperone A and fonsecinone A, two bis-naphthopyrones produced by Aspergillus aculeatus.  Magn Reson Chem. 2005;  43 962-965
  • 10 Liu J, Cao R, Yi W, Ma C, Wan Y, Zhou B, Ma L, Song H. A class of potent tyrosinase inhibitors: alkylidenethiosemicarbazide compounds.  Eur J Med Chem. 2009;  44 1773-1778
  • 11 Du Z Y, Liu R R, Shao W Y, Mao X P, Ma L, Gu L Q, Huang Z S, Chan A S C. Alpha-glucosidase inhibition of natural curcuminoids and curcumin analogs.  Eur J Med Chem. 2006;  41 213-218
  • 12 Wang S, Li X M, Teuscher F, Li D L, Diesel A, Ebel R, Proksch P, Wang B G. Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata.  J Nat Prod. 2006;  69 1622-1625

Prof. Zhi-Gang She
Prof. Lin  Ma
Prof. Yong-Cheng Lin

School of Chemistry and Chemical Engineering
Sun Yat-sen University

No.135, West Xingang Road

Guangzhou 510 275

People's Republic of China

Phone: +8 60 20 84 03 40 96

Fax: +8 60 20 84 03 40 96

Email: cesshzhg@mail.sysu.edu.cn

Email: cesmal@mail.sysu.edu.cn

Email: ceslyc@mail.sysu.edu.cn

>