Investigation of the EtOAc-soluble fraction of the 95% EtOH extract of rice fermented with the endophytic fungus Annulohypoxylon sp. led to the isolation of one new furan-3-one derivative, designated as annulofuranone (1), together with five known compounds, 2-methylcardol (2), 2-hydroxy-5-methoxy-3-tridecyl-1,4-benzoquinone (3), 3-methoxy-5-pentylphenol (4), 3-methoxy-5-hexylphenol (5), and ergosta-4,6,8(14),22-tetraen-3-one (6). Their structures were elucidated by 1D and 2D NMR spectroscopy together with MS analysis, and comparison of the spectroscopic data with those reported for structurally related compounds. All compounds were found in this fungus for the first time.
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References
G. A. Strobel and D. M. Long, ASM News, 64, 263 (1998).
G. A. Strobel, Crit. Rev. Biotechnol., 22, 315 (2002).
G. Strobel, B. Daisy, U. Castillo, and J. Harper, J. Nat. Prod., 67, 257 (2004).
L. P. Bush, H. H. Wilkinson, and C. L. Schardl, Plant Physiol., 114, 1 (1997).
R. X. Tan and W. X. Zou, Nat. Prod. Rep., 18, 448 (2001).
C. Lu and Y. Shen, J. Antibiot., 56, 415 (2003).
H. M. Hsieh and Y. M. Ju, Mycol., 97, 844 (2005).
Y. M. Ju and J. D. Rogers, Mycotaxon, 73, 371 (1999).
A. J. S. Whalley and R. L. Edwards, Can. J. Bot., 73, 802 (1995).
I. Zabetakis, J. W. Gramshaw, and D. S. Robinson, Food Chem., 65, 139 (1999).
T. Furumoto, T. Hamasaki, and H. Nakajima, Tetrahedron Lett., 38, 5523 (1997).
J. He, E. M. Kithsiri Wijeratne, B. P. Bashyal, J. Zhan, C. J. Seliga, M. X. Liu, E. E. Pierson, L. S. Pierson, H. D. VanEtten, and A. A. Leslie Gunatilaka, J. Nat. Prod., 67, 1985 (2004).
C. Li, D. K. Yue, P. B. Bu, and Y. F. Sun, Zhongguo Zhongyao Zazhi, 31, 562 (2006).
H. Ogawa and S. Natori, Chem. Pharm. Bull., 16, 1709 (1968).
W. Horper and F. J. Marner, Nat. Prod. Lett., 6, 163 (1995).
W. A. Ayer, L. M. Browne, and S. H. Lovell, Phytochemistry, 22, 2267 (1983).
G. Jinming, H. Lin, and L. Jikai, Steroids, 66, 771 (2001).
Acknowledgment
This investigation was supported by a grant from the Ministry of Economic Affairs of the Republic of China. The authors also thank Senior Technician Dr. Chyi-Jia Wang of the Center for Resources, Research and Development (CRRD) of Kaohsiung Medical University for measuring the 2D NMR data.
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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2013, pp. 381–383.
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Cheng, MJ., Wu, MD., Chen, IS. et al. A new furan-3-one derivative from the endophytic fungus Annulohypoxylon sp.. Chem Nat Compd 49, 446–449 (2013). https://doi.org/10.1007/s10600-013-0635-8
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DOI: https://doi.org/10.1007/s10600-013-0635-8