Issue 17, 2021

Miharadienes A–D with unique cyclic skeletons from a marine-derived Streptomyces miharaensis

Abstract

A new type of natural products, miharadienes A–D (1–4), was isolated from the marine-derived Streptomyces miharaensis 151KO-143. Their structures were elucidated using a combination of NMR spectroscopy, acid hydrolysis, modified Mosher's method, electronic circular dichroism (ECD) and single crystal X-ray diffraction data. Interestingly, compounds 1 and 4 featured an unusual 2,10-dioxabicyclo[5.3.1]undecane ring system and a rare 5/5 furo[3,4-c]furan ring system, respectively, and all compounds 1–4 possessed a E,E-diene moiety at a side chain. Miharadiene D (4) exhibited moderate inhibitory effect of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglia cells.

Graphical abstract: Miharadienes A–D with unique cyclic skeletons from a marine-derived Streptomyces miharaensis

Supplementary files

Article information

Article type
Research Article
Submitted
18 May 2021
Accepted
12 Jun 2021
First published
01 Jul 2021

Org. Chem. Front., 2021,8, 4845-4852

Miharadienes A–D with unique cyclic skeletons from a marine-derived Streptomyces miharaensis

B. Choi, D. Cho, D. Choi and H. J. Shin, Org. Chem. Front., 2021, 8, 4845 DOI: 10.1039/D1QO00773D

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