Synthesis of the reported structure of homocereulide and its vacuolation assay. Issue 5 (1st March 2019)

• Record Type: Journal Article
• Authors: Naka, Toshihito; Hattori, Yoshihide; Takenaka, Hiroshi; Ohta, Yoichiro; Kirihata, Mitsunori; Tanimori, Shinji
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 29:Issue 5(2019)
• Page Start: 734
• Page End: 739
• Publication Date: 2019-03-01
• Subjects: Homocereulide -- Total synthesis -- Bacillus cereus -- Emetic toxin -- Cereulide analogs; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2019.01.007
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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 ofl - O -Val-l -Val-d - O -Leu-d -Ala andl - 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.