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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.

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