Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge Dysidea sp. and Stereochemical Reassignment of 12-epi-Phyllactone D/E

The chemical investigation of the marine sponge Dysidea sp., which was collected from Bohol province in the Philippines, resulted in the identification of 15 new scalarane-type sesterterpenoids (1–14, <...

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Autores principales:	A-Young Shin, Arang Son, Changhoon Choi, Jihoon Lee
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Dysidea</i> sesterterpenoid scalarane marine sponge marine natural product anticancer activity Biology (General) QH301-705.5
Acceso en línea:	https://doaj.org/article/0dadabbd592e401bbf98749d37f9a14c
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spelling	oai:doaj.org-article:0dadabbd592e401bbf98749d37f9a14c2021-11-25T18:12:55ZIsolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E10.3390/md191106271660-3397https://doaj.org/article/0dadabbd592e401bbf98749d37f9a14c2021-11-01T00:00:00Zhttps://www.mdpi.com/1660-3397/19/11/627https://doaj.org/toc/1660-3397The chemical investigation of the marine sponge <i>D</i><i>ysidea</i> sp., which was collected from Bohol province in the Philippines, resulted in the identification of 15 new scalarane-type sesterterpenoids (<b>1</b>–<b>1</b><b>4</b>, <b>1</b><b>6</b>), together with 15 known compounds. The chemical structures of the new compounds were elucidated based on NMR spectroscopy and HRMS. The structure of 12-<i>epi</i>-phyllactone D/E (<b>15</b>) isolated during this study was originally identified in 2007. However, careful inspection of our experimental <sup>13</sup>C NMR spectrum revealed considerable discrepancies with the reported data at C-9, C-12, C-14, and C-23, leading to the correction of the reported compound to the C-12 epimer of <b>15</b>, phyllactone D/E. The biological properties of compounds <b>1</b>–<b>16</b> were evaluated using the MDA-MB-231 cancer cell line. Compound <b>7</b>, which bears a pentenone E-ring, exhibits significant cytotoxicity with a GI<sub>50</sub> value of 4.21 μM.A-Young ShinArang SonChanghoon ChoiJihoon LeeMDPI AGarticle<i>Dysidea</i>sesterterpenoidscalaranemarine spongemarine natural productanticancer activityBiology (General)QH301-705.5ENMarine Drugs, Vol 19, Iss 627, p 627 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Dysidea</i> sesterterpenoid scalarane marine sponge marine natural product anticancer activity Biology (General) QH301-705.5
spellingShingle	<i>Dysidea</i> sesterterpenoid scalarane marine sponge marine natural product anticancer activity Biology (General) QH301-705.5 A-Young Shin Arang Son Changhoon Choi Jihoon Lee Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E
description	The chemical investigation of the marine sponge <i>D</i><i>ysidea</i> sp., which was collected from Bohol province in the Philippines, resulted in the identification of 15 new scalarane-type sesterterpenoids (<b>1</b>–<b>1</b><b>4</b>, <b>1</b><b>6</b>), together with 15 known compounds. The chemical structures of the new compounds were elucidated based on NMR spectroscopy and HRMS. The structure of 12-<i>epi</i>-phyllactone D/E (<b>15</b>) isolated during this study was originally identified in 2007. However, careful inspection of our experimental <sup>13</sup>C NMR spectrum revealed considerable discrepancies with the reported data at C-9, C-12, C-14, and C-23, leading to the correction of the reported compound to the C-12 epimer of <b>15</b>, phyllactone D/E. The biological properties of compounds <b>1</b>–<b>16</b> were evaluated using the MDA-MB-231 cancer cell line. Compound <b>7</b>, which bears a pentenone E-ring, exhibits significant cytotoxicity with a GI<sub>50</sub> value of 4.21 μM.
format	article
author	A-Young Shin Arang Son Changhoon Choi Jihoon Lee
author_facet	A-Young Shin Arang Son Changhoon Choi Jihoon Lee
author_sort	A-Young Shin
title	Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E
title_short	Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E
title_full	Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E
title_fullStr	Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E
title_full_unstemmed	Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E
title_sort	isolation of scalarane-type sesterterpenoids from the marine sponge <i>dysidea</i> sp. and stereochemical reassignment of 12-<i>epi</i>-phyllactone d/e
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/0dadabbd592e401bbf98749d37f9a14c
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Isolation of Scalarane-Type Sesterterpenoids from the Marine Sponge <i>Dysidea</i> sp. and Stereochemical Reassignment of 12-<i>epi</i>-Phyllactone D/E

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