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A Cytotoxic Heterodimeric Cyclic Diarylheptanoid with a Rearranged Benzene Ring from the Seagrass Zostera marina .
- Source :
-
Journal of natural products [J Nat Prod] 2022 Oct 28; Vol. 85 (10), pp. 2468-2473. Date of Electronic Publication: 2022 Oct 19. - Publication Year :
- 2022
-
Abstract
- The widespread seagrass Zostera marina contains a new diarylheptanoid heterodimer, zosterabisphenone C ( 1 ), featuring an unprecedented rearrangement of one of its benzene rings to a cyclopentenecarbonyl unit. The planar structure and absolute configuration of zosterabisphenone C were elucidated by a combination of spectroscopic (MS, ECD, and low-temperature NMR) and computational (DFT-NMR and DFT-ECD) evidence. Consistent with the previously isolated zosterabisphenones, compound 1 was selectively cytotoxic against HCT 116 adenocarcinoma colon cancer cells, reducing their viability by 73% at 10 μM (IC <subscript>50</subscript> of 7.6 ± 1.1 μM). The biosynthetic origin of zosterabisphenone C ( 1 ) from an oxidative rearrangement of zosterabisphenone A ( 4 ) is proposed.
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 85
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 36261887
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.2c00796