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Thielavins: tuned biosynthesis and LR-HSQMBC for structure elucidation
Zeinab Y Al Subeh1, Huzefa A Raja1, Amanda Maldonado2
1Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, NC, USA.
Abstract:
A series of thielavins I, V, and Q (1-3) and the previously undescribed thielavin Z8 (4) were isolated from cultures of a fungal Shiraia-like sp. (strain MSX60519) that were grown under a suite of media and light conditions, with enhanced biosynthesis noted using rice as a substrate with 12:12 h light:dark cycles. Conversely, oatmeal medium and continuous white light-emitting diode light exposure negatively affected the production of these compounds, at least by strain MSX60519. The structure of 4 was determined using NMR spectroscopic data and mass fragmentation patterns. Of note, the utility of LR-HSQMBC and NOESY NMR experiments in the structural elucidation of these hydrogen-deficient natural products was demonstrated. Compounds 1-4 exhibited cytotoxic activity at the micromolar level against human breast, ovarian, and melanoma cancer cell lines.
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