Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium

Arihiro Iwasaki; Takato Tadenuma; Shimpei Sumimoto; Taichi Ohshiro; Kaori Ozaki; Keisuke Kobayashi; Toshiaki Teruya; Hiroshi Tomoda; Kiyotake Suenaga

doi:10.1021/acs.jnatprod.7b00137

Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium

Arihiro Iwasaki, Takato Tadenuma, Shimpei Sumimoto, Taichi Ohshiro, Kaori Ozaki, Keisuke Kobayashi, Toshiaki Teruya, Hiroshi Tomoda, Kiyotake Suenaga

Department of Chemistry

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

13 Citations (Scopus)

Abstract

Biseokeaniamides A, B, and C (1-3), structurally novel sterol O-acyltransferase (SOAT) inhibitors, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Biseokeaniamide B (2) exhibited moderate cytotoxicity against human HeLa cancer cells, and compounds 1-3 inhibited both SOAT1 and SOAT2, not only at an enzyme level but also at a cellular level. Biseokeaniamides (1-3) are the first linear lipopeptides that have been shown to exhibit SOAT-inhibitory activity.

Original language	English
Pages (from-to)	1161-1166
Number of pages	6
Journal	Journal of Natural Products
Volume	80
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00137
Publication status	Published - 2017 Apr 28

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)

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10.1021/acs.jnatprod.7b00137

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@article{da50ba0baa4e491e9817ba68e226fbab,

title = "Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium",

abstract = "Biseokeaniamides A, B, and C (1-3), structurally novel sterol O-acyltransferase (SOAT) inhibitors, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Biseokeaniamide B (2) exhibited moderate cytotoxicity against human HeLa cancer cells, and compounds 1-3 inhibited both SOAT1 and SOAT2, not only at an enzyme level but also at a cellular level. Biseokeaniamides (1-3) are the first linear lipopeptides that have been shown to exhibit SOAT-inhibitory activity.",

author = "Arihiro Iwasaki and Takato Tadenuma and Shimpei Sumimoto and Taichi Ohshiro and Kaori Ozaki and Keisuke Kobayashi and Toshiaki Teruya and Hiroshi Tomoda and Kiyotake Suenaga",

note = "Funding Information: We are grateful to Prof. L. L. Rudel (Wake Forest University, Winston-Salem, NC, USA) for kindly providing SOAT1-CHO and SOAT2-CHO cells. This work was supported by JSPS KAKENHI Grant Number 16H03285 and the Naito Foundation.",

year = "2017",

month = apr,

day = "28",

doi = "10.1021/acs.jnatprod.7b00137",

language = "English",

volume = "80",

pages = "1161--1166",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium

AU - Iwasaki, Arihiro

AU - Tadenuma, Takato

AU - Sumimoto, Shimpei

AU - Ohshiro, Taichi

AU - Ozaki, Kaori

AU - Kobayashi, Keisuke

AU - Teruya, Toshiaki

AU - Tomoda, Hiroshi

AU - Suenaga, Kiyotake

N1 - Funding Information: We are grateful to Prof. L. L. Rudel (Wake Forest University, Winston-Salem, NC, USA) for kindly providing SOAT1-CHO and SOAT2-CHO cells. This work was supported by JSPS KAKENHI Grant Number 16H03285 and the Naito Foundation.

PY - 2017/4/28

Y1 - 2017/4/28

N2 - Biseokeaniamides A, B, and C (1-3), structurally novel sterol O-acyltransferase (SOAT) inhibitors, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Biseokeaniamide B (2) exhibited moderate cytotoxicity against human HeLa cancer cells, and compounds 1-3 inhibited both SOAT1 and SOAT2, not only at an enzyme level but also at a cellular level. Biseokeaniamides (1-3) are the first linear lipopeptides that have been shown to exhibit SOAT-inhibitory activity.

AB - Biseokeaniamides A, B, and C (1-3), structurally novel sterol O-acyltransferase (SOAT) inhibitors, were isolated from an Okeania sp. marine cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Biseokeaniamide B (2) exhibited moderate cytotoxicity against human HeLa cancer cells, and compounds 1-3 inhibited both SOAT1 and SOAT2, not only at an enzyme level but also at a cellular level. Biseokeaniamides (1-3) are the first linear lipopeptides that have been shown to exhibit SOAT-inhibitory activity.

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U2 - 10.1021/acs.jnatprod.7b00137

DO - 10.1021/acs.jnatprod.7b00137

M3 - Article

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AN - SCOPUS:85018408637

SN - 0163-3864

VL - 80

SP - 1161

EP - 1166

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 4

ER -

Biseokeaniamides A, B, and C, Sterol O-Acyltransferase Inhibitors from an Okeania sp. Marine Cyanobacterium

Abstract

ASJC Scopus subject areas

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