Isolation and structure determination of a new analog of polycavernosides from marine Okeania sp. cyanobacterium

Kairi Umeda; Naoaki Kurisawa; Ghulam Jeelani; Tomoyoshi Nozaki; Kiyotake Suenaga; Arihiro Iwasaki

doi:10.3762/bjoc.20.57

Isolation and structure determination of a new analog of polycavernosides from marine Okeania sp. cyanobacterium

Beilstein J Org Chem. 2024 Mar 21:20:645-652. doi: 10.3762/bjoc.20.57. eCollection 2024.

Authors

Kairi Umeda¹, Naoaki Kurisawa¹, Ghulam Jeelani², Tomoyoshi Nozaki², Kiyotake Suenaga¹, Arihiro Iwasaki³

Affiliations

¹ Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
² Department of Biomedical Chemistry, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
³ Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

Abstract

Polycavernoside E (1), a new polycavernoside analog, was isolated from a marine Okeania sp. cyanobacterium. The relative configuration was elucidated primarily by analyzing the two dimensional nuclear magnetism resonance (2D NMR) data. The absolute configuration was clarified by comparing the electronic circular dichroism (ECD) data of 1 with those of known analogs. Polycavernoside E (1) exhibited moderate antitrypanosomal activity against Trypanosoma brucei rhodesiense. Furthermore, the isolation of polycavernoside E (1) from marine cyanobacteria provides additional evidence that marine cyanobacteria, and not red algae, are responsible for the biosynthesis of polycavernosides.

Keywords: macrolide glycoside; marine cyanobacterium; marine natural products; polycavernosides; terminal alkyne.

Grants and funding

This work was supported by JSPS KAKENHI (Grant Numbers 21K14747 and 20H02870) and The Naito Foundation.