https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

Chemistry and Biology of Mycotoxins and Related Fungal Metabolites

Chemistry and biology of resorcylic acid lactones

This study investigates the direct estrogen receptor interactions and the character of the biological activities of three estrogenic resorcylic acid lactones in the immature rat uterus. These compounds are fungal metabolites (P-1492; zearalenone) or derivatives thereof (P-1496 and P-1560; epimeric zearalanols) that have been associated with estrogenizing syndromes in cattle fed mold-infected grain. The compounds compete with estradiol for binding to the cytoplasmic receptor (P- 1496, 13.6%; P-1492, 1.8%; P-1560, 0.8% that of estradiol), and they translocate estrogen receptor sites to the nucleus, with P- 1496 showing the most prolonged nuclear receptor interaction. The three compounds induce the synthesis of the uterine induced protein (P-1496 > P-1560 > P-1492) and increase uterine weight. Direct binding studies with the most potent compound P-1496, in tritium-labeled form indicates a Kd of 1.8 nM (compared to 0.12 nM for estradiol) for interaction with uterine cytoplasmic receptor. Cytoplasmic receptor ...

Zearalenones: Characterization of the Estrogenic Potencies and Receptor Interactions of a Series of Fungal β-Resorcylic Acid Lactones*

Aigialomycins A−E (2−6), new 14-membered resorcylic macrolides, were isolated together with a known hypothemycin (1) from the mangrove fungus, Aigialus parvus BCC 5311. Structures of these compounds, including absolute configuration, were elucidated by spectroscopic methods, chemical conversions, and X-ray crystallographic analysis. Hypothemycin and aigialomycin D (5) exhibited in vitro antimalarial activity with IC50 values of 2.2 and 6.6 μg/mL, respectively, while other analogues were inactive. Cytotoxicities of these compounds were also evaluated.

Nancy A. Perkinson

Papers

New zearalenone related macrolides and isocoumarins from an unidentified fungus

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4H-1,4-benzothiazine derivatives via a novel lead tetraacetate induced ring contraction.

(.beta.-Lysyloxy)myoinositol guanidino glycoside antibiotics

The synthesis of 4-substituted-4H-1,2,4-triazole-3-thiols and 3-methylthio-4-substituted-4H,2,4-triazoles