Obionin B: An o-pyranonaphthoquinone decaketide from an unidentified fungus (MSX 63619) from the Order Pleosporales
- PMID: 22025810
- PMCID: PMC3183506
- DOI: 10.1016/j.tetlet.2011.07.102
Obionin B: An o-pyranonaphthoquinone decaketide from an unidentified fungus (MSX 63619) from the Order Pleosporales
Abstract
A fungal extract (MSX 63619), from the Mycosynthetix library of over 50,000 fungi, displayed promising cytotoxicity against a human tumor cell panel. Bioactivity-directed fractionation led to the isolation of an o-pyranonaphthoquinone decaketide, which we termed obionin B (1). The structure of 1 was deduced via spectroscopic and spectrometric techniques. The IC(50) value of 1 was moderate, ranging from 3 to 13 μM, depending on the cell line tested.
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References
-
- Newman DJ, Cragg GM. J. Nat. Prod. 2007;70:461–477. - PubMed
-
- Pearce C, Eckard P, Gruen-Wollny I, Hanske FG. In: Natural Product Chemistry for Drug Discovery. Buss AD, Butler MS, editors. The Royal Society of Chemistry; Cambridge: 2010. pp. 215–244.
-
- Butler MS. Nat. Prod. Rep. 2008;25:475–516. - PubMed
-
- Strader CR, Pearce CJ, Oberlies NH. J. Nat. Prod. 2011;74:900–907. - PubMed
-
- Hawksworth DL, Rossman AY. Phytopathology. 1997;87:888–891. - PubMed
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