Hyfraxins A and B, cytotoxic ergostane-type steroid and lanostane triterpenoid glycosides from the invasive ash dieback ascomycete Hymenoscyphus fraxineus.

Abstract:

:A virulent culture of Hymenoscyphus fraxineus, the causal agent of ash dieback, was investigated for its production of secondary metabolites in a 70 L batch fermentation. Chemical analysis of the mycelial extract by means of flash chromatography and preparative HPLC led to the isolation of a new ergostane-type steroid (1) and a new related lanostane triterpenoid (2), both revealing the same glycosylation pattern. While their planar structures were elucidated by HR-ESIMS and NMR data, relative stereochemistry was assigned by ROESY correlations in conjunction with H,H and C,H coupling constants. Absolute configuration was determined based on ROESY correlations between the aglycons and the sugar moieties, which were identified in both cases as d-mannose by GC/MS analysis of the trimethylsilylated derivatives. The isolated compounds, for which we propose the trivial names hyfraxins A (1) and B (2), were found to be cytotoxic against the mouse fibroblast cell line L929 and exhibited moderate to weak activity against Gram-positive bacteria.

journal_name

Steroids

journal_title

Steroids

authors

Surup F,Halecker S,Nimtz M,Rodrigo S,Schulz B,Steinert M,Stadler M

doi

10.1016/j.steroids.2018.03.007

subject

Has Abstract

pub_date

2018-07-01 00:00:00

pages

92-97

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(18)30060-6

journal_volume

135

pub_type

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