Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina.
Yan LiLaura GrausoSilvia ScarpatoNunzio Antonio CacciolaFrancesca BorrelliChristian ZidornAlfonso MangoniPublished in: Organic letters (2021)
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.
Keyphrases
- magnetic resonance
- high resolution
- solid state
- density functional theory
- mass spectrometry
- multiple sclerosis
- machine learning
- squamous cell carcinoma
- ms ms
- electronic health record
- big data
- deep learning
- molecular docking
- locally advanced
- case control
- radiation therapy
- artificial intelligence
- cell death
- cell cycle arrest
- cell proliferation
- signaling pathway
- pi k akt
- rectal cancer