Abstract
A new alternariol derivative, 2240B (1), together with alternariol (2), alternariol 4,10-dimethyl ether (3), and alternariol 4-methyl ether (4), was isolated from the ethyl acetate extract of the liquid medium GYT of No. 2240, the mangrove endophytic fungus from the South China Sea Coast. The structure of compound 1 was unambiguously elucidated as alternariol 4-methyl-10-acethyl ester by spectra including one/two-dimensional NMR, HREIMS, IR, and UV. The structures of compounds 2–4 were also established by spectroscopic analyses and comparison with related literature data. The anticancer tests showed that compounds 2 and 4 had strong activities against KB and KBv200 cells with IC50 values of 3.17, 3.12, and 4.82, 4.94 µg/mL, while compounds 1 and 3 exhibited weak activities against the two kinds of tumor lines with IC50 values of more than 50 µg/mL.
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References
R. X. Tan and W. X. Zou, Nat. Prod. Rep., 18, 488 (2001).
H. J. Li, Y. C. Lin, J. H. Yao, L. L. P. Vrijmoed, and E. B. Gareth, J. Asian Nat. Prod. Res., 6, 185 (2004).
G. Y. Chen, Y. C. Lin, L. Wen, L. L. P. Vrijmoed, and E. B. Gareth, Tetrahedron, 59, 4907 (2003).
X. Y. Wu, X. H. Liu, G. C. Jiang, Y. C. Lin, W. Chan, and L. L. P. Vrijmoed, Chem. Nat. Com., 41, 27 (2005).
Y. C. Lin, Z. Y. Shao, and G. C. Jiang, Tetrahedron, 56, 9607 (2000).
Y. C. Lin, X. Y. Wu, and S. Feng, J. Org. Chem., 66, 6252 (2001).
Y. C. Lin, X. Y. Wu, and S. Feng, Tetrahedron Lett., 42, 449 (2001).
X. Y. Wu, X. H. Liu, Y. C. Lin, J. H. Luo, Z. G. She, H. J. Li, W. L. Chan, S. Antus, T. Kurtan, B. Elsasser, and K. Krohn, Eur. J. Org. Chem., 40, 4061 (2005).
E. M. Brugger, J. Wagner, and D. M. Schumacher, Toxicol. Lett., 164, 221 (2006).
T. J. Schrader, W. Cherry, and K. Soper, Mutation Research-Genetic Toxicology and Environmental Mutagenesis, 606, 61 (2006).
K. Koch, J. Podlech, E. Pfeiffer, and M. Metzler, J. Org. Chem., 70, 3275 (2005).
Y. H. An, T. Z. Zhao, J. Miao, G. T. Liu, Y. Z. Zhen, Y. M. Xu, and R. L. V. Etten, J. Agric. Food Chem., 37, 1341 (1989).
G. G. Freeman, Phytochemistry, 5, 719 (1966).
Acknowledgement
We wish to acknowledge financial support from the National Natural Science Foundation of China (20072058, 20572136), the 863 Foundation of China (2003AA624010, 2006AA09Z422), the Natural Science Foundation of Guangdong Province, China (021732, 2003A3050401), and the Star Lake Biotechnology Co. Inc., Zhaoqing, Guangdong, China. We are also grateful to Jianye Zhang (Research Department, Cancer Center, Sun Yat-sen University) for his assistance in the anticancer tests.
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Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 235–238, May–June, 2008.
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Tan, N., Tao, Y., Pan, J. et al. Isolation, structure elucidation, and mutagenicity of four alternariol derivatives produced by the mangrove endophytic fungus No. 2240. Chem Nat Compd 44, 296–300 (2008). https://doi.org/10.1007/s10600-008-9046-7
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DOI: https://doi.org/10.1007/s10600-008-9046-7