Organic Letters
Organic Letters
4 years ago

Four Hybrid Flavan–Chalcones, Caesalpinnone A Possessing a 10,11-Dioxatricyclic [5.3.3.01,6]Tridecane-Bridged System and Caesalpinflavans A–C from Caesalpinia enneaphylla

Four Hybrid Flavan–Chalcones, Caesalpinnone A Possessing a 10,11-Dioxatricyclic [5.3.3.01,6]Tridecane-Bridged System and Caesalpinflavans A–C from Caesalpinia enneaphylla
Guang-Hui Xia, De-Wen Bi, Lan-Jun Zhang, Li-Qin Wang, Liu Yang, Wei-Hua Mu, Xiao-Nian Li, Yuan-Ping Li, Xue-Song Liang, Jiangmiao Hu
Caesalpinnone A (1), an unprecedented hybrid of flavan and chalcone, possessing a 10,11-dioxatricyclic [5.3.3.01,6]tridecane-bridged system, and caesalpinflavans A–C (2–4), three new hybrid flavan–chalcones, were isolated from the twigs and leaves of Caesalpinia enneaphylla. Their structures were elucidated by a combination of spectroscopic analyses and single-crystal X-ray diffraction. Caesalpinnone A showed the highest cytotoxicity against the HL-60, SMMC-7721, A-549, MCF-7, and SW-480 human tumor cell lines with an IC50 in the range of 0.54–0.87 μM.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01955

DOI: 10.1021/acs.orglett.7b01955

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