Callyspongiamides A and B, sterol O-acyltransferase inhibitors, from the Indonesian marine sponge Callyspongia sp

Magie M Kapojos; Delfly B Abdjul; Hiroyuki Yamazaki; Taichi Ohshiro; Henki Rotinsulu; Defny S Wewengkang; Deiske A Sumilat; Hiroshi Tomoda; Michio Namikoshi; Ryuji Uchida

doi:10.1016/j.bmcl.2018.03.077

Callyspongiamides A and B, sterol O-acyltransferase inhibitors, from the Indonesian marine sponge Callyspongia sp

Bioorg Med Chem Lett. 2018 Jun 1;28(10):1911-1914. doi: 10.1016/j.bmcl.2018.03.077. Epub 2018 Mar 30.

Authors

Affiliations

¹ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan; Faculty of Nursing, University of Pembangunan Indonesia, Bahu, Manado 95115, Indonesia.
² Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan; North Sulawesi Research and Development Agency, 17 Agustus Street, Manado 95117, Indonesia; Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia.
³ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan. Electronic address: yamazaki@tohoku-mpu.ac.jp.
⁴ Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, Japan.
⁵ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan; Faculty of Mathematic and Natural Sciences, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia.
⁶ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan; Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia.
⁷ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan.
⁸ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan. Electronic address: uchidar@tohoku-mpu.ac.jp.

PMID: 29631961
DOI: 10.1016/j.bmcl.2018.03.077

Abstract

Callyspongiamides A (1) and B (2), two new sterol O-acyltransferase (SOAT) inhibitors, were isolated from the Indonesian marine sponge Callyspongia sp. together with a known congener, dysamide A (3). The structures of 1 and 2 were elucidated to be polychlorine-containing modified dipeptides based on their spectroscopic data. Compounds 1-3 inhibited both of the SOAT isozymes, SOAT1 and SOAT2, in cell-based and enzyme-based assays.

Keywords: Callyspongiamide; Inhibitor; Marine sponge Callyspongia sp.; Polychlorine-containing modified dipeptide; Sterol O-acyltransferase.

Publication types

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

MeSH terms

Animals
Callyspongia / chemistry*
Callyspongia / metabolism
Dipeptides / chemistry
Dipeptides / isolation & purification
Dipeptides / pharmacology*
Enzyme Assays
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology*
Indonesia
Inhibitory Concentration 50
Isoenzymes / antagonists & inhibitors
Isoenzymes / metabolism
Magnetic Resonance Spectroscopy
Molecular Conformation
Sterol O-Acyltransferase / antagonists & inhibitors*
Sterol O-Acyltransferase / metabolism

Substances

Dipeptides
Enzyme Inhibitors
Isoenzymes
callyspongiamide A
callyspongiamide B
Sterol O-Acyltransferase