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Cysteine-Derived Pleurotin Congeners from the Nematode-Trapping Basidiomycete Hohenbuehelia grisea

Author:
Sandargo, Birthe, Thongbai, Benjarong, Stadler, Marc, Surup, Frank
Source:
Journal of natural products 2018 v.81 no.2 pp. 286-291
ISSN:
1520-6025
Subject:
Hohenbuehelia, acetylcysteine, antimicrobial properties, cysteine, cytotoxicity, fungi, metabolites, nitrogen, nuclear magnetic resonance spectroscopy, spectral analysis, stable isotopes, Thailand
Abstract:
The discovery of a Hohenbuehelia grisea specimen during a field trip in Northern Thailand led to the isolation and identification of three novel sulfur-bearing derivatives of dihydropleurotinic acid (4). Thiopleurotinic acid A (1) was established by the interpretation of spectral data (HRESIMS, 2D-NMR) as a 2-hydroxy-3-mercaptopropanoic acid conjugate of dihydropleurotinic acid. Thiopleurotinic acid B (2) was shown to be the N-acetylcysteine conjugate of 4. A third compound (3) was established as a thiazole-containing derivative. Through feeding experiments with [U–¹³C₃, ¹⁵N]-l-cysteine the formation of all three metabolites was shown to involve cysteine condensation with 4. The decreased cytotoxicity and antimicrobial activities of the new derivatives 1–3, compared to the parent compound 4, indicate a possible detoxification pathway of filamentous fungi.
Agid:
6043032