Subscribe to RSS
DOI: 10.1055/s-0030-1249955
© Georg Thieme Verlag KG Stuttgart · New York
Three Dimeric Naphtho-γ-Pyrones from the Mangrove Endophytic Fungus Aspergillus tubingensis Isolated from Pongamia pinnata
Publication History
received February 25, 2010
revised March 31, 2010
accepted April 20, 2010
Publication Date:
26 May 2010 (online)
![](https://www.thieme-connect.de/media/plantamedica/201016/lookinside/thumbnails/10.1055-s-0030-1249955-1.jpg)
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.
Key words
Aspergillus tubingensis - Pongamia pinnata - Fabaceae - endophytic fungus - metabolite - naphtho‐γ‐pyrone - tyrosinase inhibitor
- Supporting Information for this article is available online at
- Supporting Information .
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
- www.thieme-connect.de/ejournals/toc/plantamedica