Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina | Zendy

Yan Li | Zendy; Laura Grauso | Zendy; Silvia Scarpato | Zendy; Nunzio Antonio Cacciola | Zendy; Francesca Borrelli | Zendy; Christian Zidorn | Zendy; Alfonso Mangoni | Zendy

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Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina

Author(s) -

Yan Li,

Laura Grauso,

Silvia Scarpato,

Nunzio Antonio Cacciola,

Francesca Borrelli,

Christian Zidorn,

Alfonso Mangoni

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c02537

Subject(s) - chemistry , zostera marina , tautomer , cytotoxic t cell , stereochemistry , seagrass , catechol , steric effects , biochemistry , in vitro , ecology , ecosystem , biology

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 IC 50 3.6 ± 1.1 μM at 48 h.

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