Isolation of Scalarane‐Type Sesterterpenoids from the Marine Sponge Dysidea sp. and Stereochemical Reassignment of 12‐epi‐phyllactone D/E
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Title
- Isolation of Scalarane‐Type Sesterterpenoids from the Marine Sponge Dysidea sp. and Stereochemical Reassignment of 12‐epi‐phyllactone D/E
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Author(s)
- Shin, A Young; Son, Arang; Choi, Changhoon; Lee, Jihoon
- KIOST Author(s)
- Shin, A Young(신아영); Lee, Ji Hoon(이지훈)
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Alternative Author(s)
- 신아영; 이지훈
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Publication Year
- 2021-11
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Abstract
- 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, 16), together with 15 known compounds. The chemical structures of the new compounds were elucidated based on NMR spectroscopy and HRMS. The structure of 12-epi-phyllactone D/E (15) isolated during this study was originally identified in 2007. However, careful inspection of our experimental 13C 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 15, phyllactone D/E. The biological properties of compounds 1–16 were evaluated using the MDA-MB-231 cancer cell line. Compound 7, which bears a pentenone E-ring, exhibits significant cytotoxicity with a GI50 value of 4.21 mM.
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ISSN
- 1660-3397
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/41687
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DOI
- 10.3390/md19110627
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Bibliographic Citation
- Marine Drugs, v.19, no.11, 2021
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Publisher
- Multidisciplinary Digital Publishing Institute (MDPI)
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Keywords
- Dysidea; sesterterpenoid; scalarane; marine sponge; marine natural product; anticancer activity; stereochemistry reassignment
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Type
- Article
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Language
- English
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Document Type
- Article
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