Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp.

Chemical profiling of the Streptomyces sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A−C (1−3...

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Main Authors:	Munhyung Bae, Joon Soo An, Seong-Heon Hong, Eun Seo Bae, Beomkoo Chung, Yun Kwon, Suckchang Hong, Ki-Bong Oh, Jongheon Shin, Sang Kook Lee, Dong-Chan Oh
Format:	Article
Language:	English
Published:	MDPI AG 2020-02-01
Series:	Marine Drugs
Subjects:	molecular modeling electronic circular dichroism quantum mechanics-based computation angucyclinone <i>streptomyces</i> cytotoxicity
Online Access:	https://www.mdpi.com/1660-3397/18/2/121

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spelling	doaj-8c9912b696b748bca16986e2ef01cf012020-11-25T01:40:01ZengMDPI AGMarine Drugs1660-33972020-02-0118212110.3390/md18020121md18020121Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp.Munhyung Bae0Joon Soo An1Seong-Heon Hong2Eun Seo Bae3Beomkoo Chung4Yun Kwon5Suckchang Hong6Ki-Bong Oh7Jongheon Shin8Sang Kook Lee9Dong-Chan Oh10Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaDepartment of Agricultural Biotechnology, College of Agriculture & Life Sciences, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 08826, KoreaDepartment of Agricultural Biotechnology, College of Agriculture & Life Sciences, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, KoreaChemical profiling of the <i>Streptomyces</i> sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A−C (<b>1</b>−<b>3</b>). The structures of <b>1</b>−<b>3</b> were found to be rearranged, multicyclic, angucyclinone-class compounds according to nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The configurations of their stereogenic centers were successfully assigned using a combination of quantum mechanics−based computational methods for calculating the NMR shielding tensor (DP4 and CP3) as well as electronic circular dichroism (ECD) along with a modified version of Mosher’s method. Donghaecyclinones A−C (<b>1</b>−<b>3</b>) displayed cytotoxicity against diverse human cancer cell lines (IC<sub>50</sub>: 6.7−9.6 μM for <b>3</b>).https://www.mdpi.com/1660-3397/18/2/121molecular modelingelectronic circular dichroismquantum mechanics-based computationangucyclinone<i>streptomyces</i>cytotoxicity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Munhyung Bae Joon Soo An Seong-Heon Hong Eun Seo Bae Beomkoo Chung Yun Kwon Suckchang Hong Ki-Bong Oh Jongheon Shin Sang Kook Lee Dong-Chan Oh
spellingShingle	Munhyung Bae Joon Soo An Seong-Heon Hong Eun Seo Bae Beomkoo Chung Yun Kwon Suckchang Hong Ki-Bong Oh Jongheon Shin Sang Kook Lee Dong-Chan Oh Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp. Marine Drugs molecular modeling electronic circular dichroism quantum mechanics-based computation angucyclinone <i>streptomyces</i> cytotoxicity
author_facet	Munhyung Bae Joon Soo An Seong-Heon Hong Eun Seo Bae Beomkoo Chung Yun Kwon Suckchang Hong Ki-Bong Oh Jongheon Shin Sang Kook Lee Dong-Chan Oh
author_sort	Munhyung Bae
title	Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp.
title_short	Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp.
title_full	Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp.
title_fullStr	Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp.
title_full_unstemmed	Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp.
title_sort	donghaecyclinones a–c: new cytotoxic rearranged angucyclinones from a volcanic island-derived marine <i>streptomyces</i> sp.
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2020-02-01
description	Chemical profiling of the <i>Streptomyces</i> sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A−C (<b>1</b>−<b>3</b>). The structures of <b>1</b>−<b>3</b> were found to be rearranged, multicyclic, angucyclinone-class compounds according to nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The configurations of their stereogenic centers were successfully assigned using a combination of quantum mechanics−based computational methods for calculating the NMR shielding tensor (DP4 and CP3) as well as electronic circular dichroism (ECD) along with a modified version of Mosher’s method. Donghaecyclinones A−C (<b>1</b>−<b>3</b>) displayed cytotoxicity against diverse human cancer cell lines (IC<sub>50</sub>: 6.7−9.6 μM for <b>3</b>).
topic	molecular modeling electronic circular dichroism quantum mechanics-based computation angucyclinone <i>streptomyces</i> cytotoxicity
url	https://www.mdpi.com/1660-3397/18/2/121
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Donghaecyclinones A–C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine <i>Streptomyces</i> sp.

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