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

21 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

UN SDGs

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

SDG 3 Good Health and Well-being
SDG 14 Life Below Water

ASJC Scopus subject areas

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

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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.

UR - https://www.scopus.com/pages/publications/85018408637

UR - https://www.scopus.com/pages/publications/85018408637#tab=citedBy

U2 - 10.1021/acs.jnatprod.7b00137

DO - 10.1021/acs.jnatprod.7b00137

M3 - Article

C2 - 28294609

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

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ASJC Scopus subject areas

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