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

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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 language	English
Pages (from-to)	2907-2915
Number of pages	9
Journal	Journal of Natural Products
Volume	82
Issue number	10
DOIs	https://doi.org/10.1021/acs.jnatprod.9b00749
Publication status	Published - 2019 Oct 25

ASJC Scopus subject areas

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.jnatprod.9b00749

Cite this

@article{8bcc4d97442b4026957d0630468e427c,

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

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.",

author = "Kaori Ozaki and Arihiro Iwasaki and Dai Sezawa and Haruka Fujimura and Tomoyoshi Nozaki and Yumiko Saito-Nakano and Kiyotake Suenaga and Toshiaki Teruya",

note = "Funding Information: We thank Y. Umeki for technical assistance and the Japanese Red Cross Society for providing human RBCs and plasma. The P. falciparum 3D7 line was obtained from MR4 (contributed by D. J. Carucci, MRA-102). This work was supported in part by a Grant-in-Aid for 15K01803, 18K05337, 18K14346, and 16H03285 from the Ministry of Education, Culture, Sports, Science and Technology, Japan. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society and American Society of Pharmacognosy.",

year = "2019",

month = oct,

day = "25",

doi = "10.1021/acs.jnatprod.9b00749",

language = "English",

volume = "82",

pages = "2907--2915",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium

AU - Ozaki, Kaori

AU - Iwasaki, Arihiro

AU - Sezawa, Dai

AU - Fujimura, Haruka

AU - Nozaki, Tomoyoshi

AU - Saito-Nakano, Yumiko

AU - Suenaga, Kiyotake

AU - Teruya, Toshiaki

N1 - Funding Information: We thank Y. Umeki for technical assistance and the Japanese Red Cross Society for providing human RBCs and plasma. The P. falciparum 3D7 line was obtained from MR4 (contributed by D. J. Carucci, MRA-102). This work was supported in part by a Grant-in-Aid for 15K01803, 18K05337, 18K14346, and 16H03285 from the Ministry of Education, Culture, Sports, Science and Technology, Japan. Publisher Copyright: Copyright © 2019 American Chemical Society and American Society of Pharmacognosy.

PY - 2019/10/25

Y1 - 2019/10/25

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85073108529&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85073108529&partnerID=8YFLogxK

U2 - 10.1021/acs.jnatprod.9b00749

DO - 10.1021/acs.jnatprod.9b00749

M3 - Article

C2 - 31549837

AN - SCOPUS:85073108529

SN - 0163-3864

VL - 82

SP - 2907

EP - 2915

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 10

ER -

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

Abstract

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this