New Terpendole Congeners, Inhibitors of Sterol O-Acyltransferase, Produced by Volutella citrinella BF-0440

New terpendoles N-P (1–3) were isolated along with 8 structurally related known compounds including terpendoles and voluhemins from a culture broth of the fungus Volutella citrinella BF-0440. The structures of 1–3 were elucidated using various...

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Main Authors:	Elyza Aiman Azizah Nur, Keisuke Kobayashi, Ai Amagai, Taichi Ohshiro, Hiroshi Tomoda
Format:	Article
Language:	English
Published:	MDPI AG 2020-07-01
Series:	Molecules
Subjects:	terpendole sterol <i>O</i>-acyltransferase SOAT inhibitor fungal metabolite
Online Access:	https://www.mdpi.com/1420-3049/25/13/3079

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spelling	doaj-172289c24ec6437d9cdc4cbf5ef7044b2020-11-25T03:36:22ZengMDPI AGMolecules1420-30492020-07-01253079307910.3390/molecules25133079New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440Elyza Aiman Azizah Nur0Keisuke Kobayashi1Ai Amagai2Taichi Ohshiro3Hiroshi Tomoda4Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, JapanDepartment of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, JapanDepartment of Microbial Chemistry, School of Pharmacy, Kitasato University, Tokyo 108-8641, JapanDepartment of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, JapanDepartment of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, JapanNew terpendoles N-P (<b>1–3</b>) were isolated along with 8 structurally related known compounds including terpendoles and voluhemins from a culture broth of the fungus <i>Volutella citrinella </i>BF-0440. The structures of <b>1–3</b> were elucidated using various spectroscopic experiments including 1D- and 2D-NMR. All compounds <b>1–3</b> contained a common indole–diterpene backbone. Compounds <b>2</b> and <b>3</b> had 7 and 6 consecutive ring systems with an indole ring, respectively, whereas <b>1</b> had a unique indolinone plus 4 consecutive ring system. Compounds <b>2</b> and <b>3</b> inhibited both sterol <i>O</i>-acyltransferase 1 and 2 isozymes, but <b>1</b> lost the inhibitory activity. Structure–activity relationships of fungal indole–diterpene compounds are discussed.https://www.mdpi.com/1420-3049/25/13/3079terpendolesterol <i>O</i>-acyltransferaseSOATinhibitorfungal metabolite
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Elyza Aiman Azizah Nur Keisuke Kobayashi Ai Amagai Taichi Ohshiro Hiroshi Tomoda
spellingShingle	Elyza Aiman Azizah Nur Keisuke Kobayashi Ai Amagai Taichi Ohshiro Hiroshi Tomoda New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440 Molecules terpendole sterol <i>O</i>-acyltransferase SOAT inhibitor fungal metabolite
author_facet	Elyza Aiman Azizah Nur Keisuke Kobayashi Ai Amagai Taichi Ohshiro Hiroshi Tomoda
author_sort	Elyza Aiman Azizah Nur
title	New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440
title_short	New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440
title_full	New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440
title_fullStr	New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440
title_full_unstemmed	New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440
title_sort	new terpendole congeners, inhibitors of sterol <i>o</i>-acyltransferase, produced by <i>volutella citrinella</i> bf-0440
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2020-07-01
description	New terpendoles N-P (<b>1–3</b>) were isolated along with 8 structurally related known compounds including terpendoles and voluhemins from a culture broth of the fungus <i>Volutella citrinella </i>BF-0440. The structures of <b>1–3</b> were elucidated using various spectroscopic experiments including 1D- and 2D-NMR. All compounds <b>1–3</b> contained a common indole–diterpene backbone. Compounds <b>2</b> and <b>3</b> had 7 and 6 consecutive ring systems with an indole ring, respectively, whereas <b>1</b> had a unique indolinone plus 4 consecutive ring system. Compounds <b>2</b> and <b>3</b> inhibited both sterol <i>O</i>-acyltransferase 1 and 2 isozymes, but <b>1</b> lost the inhibitory activity. Structure–activity relationships of fungal indole–diterpene compounds are discussed.
topic	terpendole sterol <i>O</i>-acyltransferase SOAT inhibitor fungal metabolite
url	https://www.mdpi.com/1420-3049/25/13/3079
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New Terpendole Congeners, Inhibitors of Sterol <i>O</i>-Acyltransferase, Produced by <i>Volutella citrinella</i> BF-0440

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