Dereplication of macrocyclic trichothecenes from extracts of filamentous fungi through UV and NMR profiles.

The Journal of Antibiotics
Arlene A Sy-CorderoNicholas H Oberlies

Abstract

Macrocyclic trichothecenes (MTs), which have potent cytotoxicity, have been isolated from many different fungal species. These compounds were evaluated clinically by the US National Cancer Institute in the 1970s and 1980s. However, they have yet to be advanced into viable drugs because of severe side effects. Our team is investigating a diverse library of filamentous fungi for new anticancer leads. To avoid reisolating MTs through bioactivity-directed fractionation studies, a protocol for their facile dereplication was developed. The method uses readily available photodiode array detectors to identify one of two types of characteristic UV spectra for these compounds. In addition, diagnostic signals can be observed in the (1)H-NMR spectra, particularly for the epoxide and conjugated diene moieties, even at the level of a crude extract. Using these techniques in a complementary manner, MTs can be dereplicated rapidly.

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Citations

Jan 25, 2014·Journal of Natural Products·Tamam El-ElimatNicholas H Oberlies
Jul 21, 2015·Journal of Natural Products·Vincent P SicaNicholas H Oberlies
Aug 4, 2016·Future Medicinal Chemistry·Mariana González-MedinaJosé L Medina-Franco
Jan 12, 2017·The Journal of Antibiotics·Noemi D PaguiganNicholas H Oberlies
Aug 3, 2011·Natural Product Reports·Braulio M Fraga
Oct 14, 2016·Magnetic Resonance in Chemistry : MRC·Clark D RidgeSimon F R Hinkley
May 22, 2019·Natural Product Reports·Nicholas H OberliesHuzefa A Raja

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

Galaxie Chromatography Workstation

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