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Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
- Source :
- Organic Letters
- Publication Year :
- 2021
- Publisher :
- American Chemical Society, 2021.
-
Abstract
- Two diarylheptanoid heterodimers, zosterabisphenones A (1) and B (2), were isolated from the seagrass Zostera marina. They feature unprecedented catechol keto tautomers, stable because of steric constraints. Their structure elucidation was based on extensive low-temperature NMR studies and ECD and MS data, with the essential aid of DFT prediction of NMR and ECD spectra. Zosterabisphenone B (2) was selectively cytotoxic against the adenocarcinoma colon cancer cell line HCT116 with IC50 3.6 ± 1.1 μM at 48 h.
- Subjects :
- Steric effects
Catechol
Letter
Magnetic Resonance Spectroscopy
biology
Molecular Structure
Stereochemistry
Zosteraceae
Organic Chemistry
Diarylheptanoid
Catechols
biology.organism_classification
Biochemistry
Tautomer
chemistry.chemical_compound
Seagrass
chemistry
Isomerism
Diarylheptanoids
Zostera marina
Cytotoxic T cell
Physical and Theoretical Chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 15237052 and 15237060
- Volume :
- 23
- Issue :
- 18
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....bca3739fa03da3605fcdf3d92102ce7e