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Thielavins: tuned biosynthesis and LR-HSQMBC for structure elucidation.

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.

SUBMITTER: Al Subeh ZY

PROVIDER: S-EPMC8084880 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Thielavins: tuned biosynthesis and LR-HSQMBC for structure elucidation.

Al Subeh Zeinab Y ZY Raja Huzefa A HA Maldonado Amanda A Burdette Joanna E JE Pearce Cedric J CJ Oberlies Nicholas H NH

The Journal of antibiotics 20210125 5

A series of thielavins I, V, and Q (1-3) and the previously undescribed thielavin Z<sub>8</sub> (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 s ...[more]

PMID: 33495550

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