Citation:
Ri-Dao Chen, Zheng Yan, Jian-Hua Zou, Nan Wang, Jun-Gui Dai. Rubratoxin C, a new nonadride derivative from an endophytic fungus Penicillium sp. F-14[J]. Chinese Chemical Letters,
;2014, 25(9): 1308-1310.
doi:
10.1016/j.cclet.2014.03.040
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One new nonadride derivative rubratoxin C (1) together with a known compound rubratoxin B (2) were isolated from an endophytic fungus Penicillium sp. F-14. Their structures were elucidated by various spectroscopicmethods. Bioassays showed that 2 had moderate cytotoxic effect against HCT-8, BEL-7402, Ketr3, A2780, MCF-7 and BGC-823 human cancer cell lines, and 1 exhibited weak activity.
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[1]
[1] H.W. Zhang, Y.C. Song, R.X. Tan, Biology and chemistry of endophytes, Nat. Prod. Rep. 23 (2006) 753-771.
-
[2]
[2] R.X. Tan, W.X. Zou, Endophytes: a rich source of functional metabolites, Nat. Prod. Rep. 18 (2001) 448-459.
-
[3]
[3] S. Kaul, S. Gupta, M. Ahmed, M.K. Dhar, Endophytic fungi from medicinal plants: a treasure hunt for bioactive metabolites, Phytochem. Rev. 11 (2012) 487-505.
-
[4]
[4] Wuringege, Z.K. Guo, W. Wei, et al., Polyketides from the plant endophytic fungus Cladosporium sp. IFB3lp-2, J. Asian Nat. Prod. Res. 15 (2013) 928-933.
-
[5]
[5] Z.F. Fang, S.S. Yu, W.Q. Zhou, et al., A new isocoumarin from metabolites of the endophytic fungus Alternaria tenuissima (Nees & T. Nees: Fr.) Wiltshire, Chin. Chem. Lett. 23 (2012) 317-320.
-
[6]
[6] A. Stierle, G. Strobel, D. Stierle, Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew, Science 260 (1993) 214-216.
-
[7]
[7] J.M. Wang, G.Z. Ding, L. Fang, et al., Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum, J. Nat. Prod. 73 (2010) 1240-1249.
-
[8]
[8] J.M. Wang, N. Jiang, J. Ma, et al., Study on absolute configurations of a/a0 chiral carbons of thiodiketopiperazines by experimental and calculated circular dichroism spectra, Tetrahedron 69 (2013) 1195-1201.
-
[9]
[9] H.L. Ge, D.W. Zhang, L. Li, et al., Two new terpenoids from endophytic fungus Periconia sp. F-31, Chem. Pharm. Bull. 59 (2011) 1541-1544.
-
[10]
[10] D.W. Zhang, H.L. Ge, D. Xie, et al., Periconiasins A-C, new cytotoxic cytochalasans with an unprecedented 9/6/5 tricyclic ring system from endophytic fungus Periconia sp., Org Lett. 15 (2013) 1674-1677.
-
[11]
[11] S. Natori, S. Sakaki, H. Kurata, et al., Production of rubratoxin B by Penicillium purpurogenum Stoll, Appl. Microbiol. 19 (1970) 613-617.
-
[12]
[12] H. Nagashima, K. Nakamura, T. Goto, Stress-activated MAP kinases regulate rubratoxin B-caused cytotoxicity and cytokine secretion in hepatocyte-derived HepG2 cells, Toxicol. Lett. 155 (2005) 259-267.
-
[13]
[13] T. Wang, Y. Zhang, Y. Wang, Y.H. Pei, Anti-tumor effects of rubratoxin B on cell toxicity, inhibition of cell proliferation, cytotoxic activity and matrix metalloproteinase-2,9, Toxicol. in Vitro 21 (2007) 646-650.
-
[14]
[14] V. Fimiani, A. Richetti, Antitumor effect of a mycotoxin: rubratoxin B, Chemotherapy 39 (1993) 59-62.
-
[15]
[15] S. Nieminen, C. Tamm, 1H-und 13C-NMR spektroskopie der nonadride, Helv. Chim. Acta 64 (1981) 2791-2801.
-
[16]
[16] G. Buechi, K.M. Snader, J.D. White, J. Zanos Gougoutas, S. Singh, Structures of rubratoxins A and B, J. Am. Chem. Soc. 92 (1970) 6638-6641.
-
[17]
[17] J.D. White, J. Kim, N.E. Drapela, Enantiospecific synthesis of (+)-byssochlamic acid, a nonadride from the ascomycete Byssochlamys fulva, J. Am. Chem. Soc. 122 (2000) 8665-8671.
-
[18]
[18] Y.B. Liu, G.Z. Ding, Y. Li, et al., Structures and absolute configurations of penicillactones A-C from an endophytic microorganism, Penicillium dangeardii Pitt, Org. Lett. 15 (2013) 5206-5209.
-
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