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Four new diterpenes from the mangrove Ceriops tagal and structure revision of four dolabranes with a 4,18-epoxy group

Zhang, Xiaohui, Li, Wanshan, Shen, Li, Wu, Jun
Fitoterapia 2017
Ceriops tagal, X-ray diffraction, breast neoplasms, copper, cytotoxicity, diterpenoids, human cell lines, inhibitory concentration 50, medicinal plants, nuclear magnetic resonance spectroscopy, spectral analysis
Four new diterpenes named tagalons A-D (1–4), comprising an isopimarane (1), two 16-nor-pimaranes (2–3), and a dolabrane (4), were isolated from the Chinese mangrove, Ceriops tagal, together with four known dolabranes containing a 4,18-epoxy group, viz. tagalene I (5), 4-epitagalene I (6), tagalsin A (7), and tagalsin B (8). The structures of these compounds were unambiguously established by HR-ESIMS and NMR spectroscopic data. Based on the new criteria of NOE interactions between H2-18/H3-19 and H2-18/H3-20, previously reported relative configurations of the above four known dolabranes were correctly revised as their C-4 epimers, respectively. The relative configuration of tagalon B (2) and the absolute configuration of tagalene I (5) were established by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation. Most notably, tagalons C (3) and D (4) exhibited selective cytotoxicities against the human breast cancer cell line MT-1 with IC50 values of 3.75 and 8.07μM, respectively; whereas tagalene I (5) displayed potent cytotoxic effects against four human breast cancer cell lines MDA-MB-453, MDA-MB-231, SK-BR-3, and MT-1 with IC50 values of 8.97, 8.97, 4.62, and 3.93μM, respectively.