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Discovery and Photoisomerization of New Pyrrolosesquiterpenoids Glaciapyrroles D and E, from Deep-Sea Sediment Streptomyces sp.
- Title
- Discovery and Photoisomerization of New Pyrrolosesquiterpenoids Glaciapyrroles D and E, from Deep-Sea Sediment Streptomyces sp.
- Authors
- Ko K.; Kim S.-H.; Park S.; Han H.S.; Lee J.K.; Cha J.W.; Hwang S.; Choi K.Y.; Song Y.-J.; Nam S.-J.; Shin J.; Nam S.-I.; Kwon H.C.; Park J.-S.; Oh D.-C.
- Ewha Authors
- 남상집
- SCOPUS Author ID
- 남상집
- Issue Date
- 2022
- Journal Title
- Marine Drugs
- ISSN
- 1660-3397
- Citation
- Marine Drugs vol. 20, no. 5
- Keywords
- deep-sea sediment; glaciapyrrole; photoisomerization; pyrrolosesquiterpene; Streptomyces; structure elucidation
- Publisher
- MDPI
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- Two new pyrrolosesquiterpenes, glaciapyrroles D (1) and E (2) were discovered along with the previously reported glaciapyrrole A (3) from Streptomyces sp. GGS53 strain isolated from deep-sea sediment. This study elucidated the planar structures of 1 and 2 using nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV), and infrared (IR) spectroscopic data. The absolute configurations of the glaciapyrroles were determined by Mosher’s method, circular dichroism spectroscopy, and X-ray crystallography. Under 366 nm UV irradiation, the glaciapyrroles were systematically converted to the corresponding photoglaciapyrroles (4–6) via photoisomerization, resulting in the diversification of the glaciapyrrole family compounds. The transformation of the glaciapyrrole Z to E isomers occurred in a 1:1 ratio, based on virtual validation of the photoisomer-ization of these olefinic compounds by1 H-NMR spectroscopy and liquid chromatography/mass spectrometry (LC/MS) analysis. Finally, when encapsulated in poly(lactic-co-glycolic acid) nanopar-ticles, glaciapyrrole E and photoglaciapyrrole E displayed significant inhibitory activity against influenza A virus. This is the first report of antiviral effects from glaciapyrrole family compounds, whose biological functions have only been subjected to limited studies so far. © 2022 by the authors. Licensee MDPI, Basel, Switzerland.
- DOI
- 10.3390/md20050281
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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