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Synthesis of the reported structure of homocereulide and its vacuolation assay.

Abstract：

:Homocereulide, isolated from marine bacterium Bacillus cereus, is an analog of emetic toxin cereulide. There is no report on its structure determination and involvement in B. cereus-associated food poisoning. Homocereulide is a cyclic dodecadepsipeptide composed of l-O-Val-l-Val-d-O-Leu-d-Ala and l-O-allo-Ile-d-Val-d-O-Leu-d-Ala. Here, we synthesized homocereulide using liquid phase fragment condensation. The NMR spectrum of synthesized homocereulide confirmed the intended structure and LC-MS results were consistent with natural products. Morphological evaluation using HEp-2 cells showed higher toxicity with homocereulide (1.39 nM) than cereulide (3.95 nM). Though cereulide is the main component in broth culture, homocereulide is also likely involved in B. cereus-associated food poisoning.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Naka T,Hattori Y,Takenaka H,Ohta Y,Kirihata M,Tanimori S

doi

10.1016/j.bmcl.2019.01.007

subject

Has Abstract

pub_date

2019-03-01 00:00:00

pages

734-739

issue

5

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(19)30007-1

journal_volume

29

pub_type

杂志文章

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