From the seeds of the traditional medicinal plant Ziziphus jujuba growing in Uzbekistan, the fungal endophyte Alternaria sp. was isolated. Extracts of this fungus grown on solid rice and liquid Wickerham culture media yielded 21 natural products. These natural products include the new phthalide natural product (±)7-methoxyphthalide-3-acetic acid (1) in addition to 20 known compounds including 19 polyketides and one alkaloid. Moreover, the OSMAC (One Strain MAny Compounds) approach is applied in this study. The unambiguous structure of the new compound was elucidated on the basis of one- and two-dimensional NMR spectroscopy in addition to HR-ESI-MS. Compounds 2, 3, 4, and 7 exhibited a cytotoxic activity against mouse lymphoma cell lines (L5178Y) with IC50 values of 1.7, 7.8, 6.8, and 6.2 μM, respectively when compared with the positive control kahalalide F (IC50 4.3 μM).
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References
K. D. Hyde and K. Soytong, Fungal Divers., 33, 163 (2008).
C. W. Bacon and J. F. White, Microbial Endophytes, Marcel Dekker, New York, 2000.
G. A. Strobel and D. M. Long, ASM News, 64, 263 (1998).
T. N. Sieber, Fungal Biol. Rev., 21, 75 (2007).
R. X. Tan and W. X. Zhou, Nat. Prod. Rep., 18, 448 (2001).
A. A. L. Gunatilaka, J. Nat. Prod., 69, 509 (2006).
H. W. Zhang, Y. C. Song, and R. X. Tan, Nat. Prod. Rep., 23, 753 (2006).
V. C. Verma, R. N. Kharwar, and G. A. Strobel, Nat. Prod. Commun., 4, 1511 (2009).
R. N. Kharwar, A. Mishra, S. K. Gond, A. Stierle, and D. B. Stierle, Nat. Prod. Rep., 28, 1208 (2011).
A. H. Aly, A. Debbab, and P. Proksch, Pharmazie, 68, 499 (2013).
G. Strobel and B. Daisy, Microbiol. Mol. Biol. Rev., 67, 491 (2003).
W. Y. Huang, Y. Cai, K. D. Hyde, H. Corke, and M. Sun, World J. Microbiol. Biotechnol., 23, 1253 (2007).
M. A. Gamboa, S. Laureano, and P. Bayman, Mycopathologia, 156, 41 (2002).
R. T. Mahajan and M. Z. Chopda, Pharmacogn. Rev., 3, 320 (2009).
D. W. Knight and D. A. Portas, Tetrahedron Lett., 51, 4543 (1977).
S. O. Silva, J. N. Reed, R. J. Billedeau, X. Wang, D. J. Norris, and V. Snieckus, Tetrahedron, 48, 4863 (1992).
P. A. Onocha, D. A. Okorie, J. D. Connolly, and D. S. Roycroft, Phytochemistry, 40, 1183 (1995).
E. Stinson, W. B. Wise, R. A. Moreau, A. J. Jurewicz, and P. E. Pfeffer, Can. J. Chem., 64, 1590 (1986).
A. Hassan, Novel Natural Products from Endophytic Fungi of Egyptian Medicinal Plants, Chemical and Biological Characterization, Dissertation, Heinrich-Heine-University, 2007.
K. Krohn, M. John, H. J. Aust, S. Draeger, and B. Schulz, Nat. Prod. Lett., 14, 31 (1999).
A. Arnone, G. Nasini, L. Merlini, and G. Assante, J. Chem. Soc. Perkin Trans., 1, 525 (1986).
K. Kameda and M. Namiki, Chem. Lett., 3, 1491 (1974).
Y. Kimura, T. Mizuno, H. Nakajima, and T. Hamasaki, Biosci. Biotechnol. Biochem., 56, 1664 (1992).
S. E. Sajjadi, Y. Shokoohinia, and N. Moayedi, J. Nat. Pharm. Prod., 7, 159 (2012).
S. Lai, Y. Shizuri, S. Yamamura, K. Kawai, and H. Furukawa, Heterocycles, 32, 297 (1991).
G. A. Ellestad, F. M. Lovell, N. A. Perkinson, R. T. Hargreaves, and W. J. McGahren, J. Org. Chem., 43, 2339 (1978).
A. Ichihara, M. Hashimoto, T. Hirai, I. Takeda, Y. Sasamura, S. Sakamura, R. Sato, and A. Tajimi, Chem. Lett., 14, 95 (1989).
T. O. Larsen and J. Breinholt, J. Nat. Prod., 62, 1182 (1999).
J. Kjer, A. Debbab, A. H. Aly, and P. Proksch, Nat. Protoc., 5, 479 (2010).
H-J. Schiewe and A. Zeeck, J. Antibiot., 52, 635 (1999).
M. Ashour, R. Edrada, R. Ebel, V. Wray, W. Watjen, K. Padmakumar, W. E. G. Muller, W.- H. Lin, and P. Proksch, J. Nat. Prod., 69, 1547 (2006).
Acknowledgment
The KSU are gratefully acknowledged for (R. S. O). We are indebted to Prof. W. E. G. Muller (Johannes Gutenberg University, Mainz, Germany) for performing the cytotoxicity assay.
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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2017, pp. 878–880.
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Orfali, R.S., Ebrahim, W. & El-Shafae, A.M. Secondary Metabolites from Alternaria sp., a Fungal Endophyte Isolated from the Seeds of Ziziphus jujuba . Chem Nat Compd 53, 1031–1034 (2017). https://doi.org/10.1007/s10600-017-2195-9
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DOI: https://doi.org/10.1007/s10600-017-2195-9