Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium

Kaori Ozaki; Arihiro Iwasaki; Dai Sezawa; Haruka Fujimura; Tomoyoshi Nozaki; Yumiko Saito-Nakano; Kiyotake Suenaga; Toshiaki Teruya

doi:10.1021/acs.jnatprod.9b00749

Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium

J Nat Prod. 2019 Oct 25;82(10):2907-2915. doi: 10.1021/acs.jnatprod.9b00749. Epub 2019 Sep 24.

Authors

Kaori Ozaki¹, Arihiro Iwasaki², Dai Sezawa², Haruka Fujimura², Tomoyoshi Nozaki³, Yumiko Saito-Nakano⁴, Kiyotake Suenaga², Toshiaki Teruya¹

Affiliations

¹ Graduate School of Engineering and Science , University of the Ryukyus , 1 Senbaru , Nishihara , Okinawa 903-0213 , Japan.
² Department of Chemistry, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama , Kanagawa 223-8522 , Japan.
³ Department of Biomedical Chemistry, Graduate School of Medicine , The University of Tokyo , 7-3-1 Hongo , Bunkyo-ku, Tokyo 113-0033 , Japan.
⁴ Department of Parasitology , National Institute of Infectious Diseases , 1-23-1 Toyama , Shinjuku-ku, Tokyo 162-8640 , Japan.

PMID: 31549837
DOI: 10.1021/acs.jnatprod.9b00749

Abstract

The bioassay-guided fractionation of an Okeania sp. marine cyanobacterium collected in Okinawa led to the isolation of the lipopeptide mabuniamide (1). The gross structure of 1 was determined by spectroscopic analyses, and its absolute configuration was determined using Marfey's analysis of the acid hydrolysate of 1. The absolute configuration of 1 was confirmed by total synthesis. Mabuniamide (1) stimulated glucose uptake in cultured rat L6 myotubes. In addition, mabuniamide (1) and its stereoisomer (2) exhibited moderate antimalarial activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antimalarials / pharmacology
Cells, Cultured
Cyanobacteria / chemistry*
Lipopeptides / chemical synthesis
Lipopeptides / isolation & purification*
Lipopeptides / pharmacology
Marine Biology
Molecular Conformation
Rats

Substances

Antimalarials
Lipopeptides