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

Research output: Contribution to journalArticle

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.

Original languageEnglish
JournalJournal of Natural Products
DOIs
Publication statusAccepted/In press - 2019 Jan 1

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Lipopeptides
Stereoisomerism
Bioassay
Skeletal Muscle Fibers
Antimalarials
Cyanobacteria
Fractionation
Biological Assay
Rats
Glucose
Acids

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium. / Ozaki, Kaori; Iwasaki, Arihiro; Sezawa, Dai; Fujimura, Haruka; Nozaki, Tomoyoshi; Saito-Nakano, Yumiko; Suenaga, Kiyotake; Teruya, Toshiaki.

In: Journal of Natural Products, 01.01.2019.

Research output: Contribution to journalArticle

Ozaki, Kaori ; Iwasaki, Arihiro ; Sezawa, Dai ; Fujimura, Haruka ; Nozaki, Tomoyoshi ; Saito-Nakano, Yumiko ; Suenaga, Kiyotake ; Teruya, Toshiaki. / Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium. In: Journal of Natural Products. 2019.
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