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Chirita drakei Burtt (now accepted as Primulina drakei (B.L.Burtt) Mich.Möller & A.Weber) is growing on limestone mountain slopes of Ha Long Bay islands in Vietnam. The chemical investigation of the aerial parts of C. drakei led to the isolation and structural elucidation of two new compounds named chiridrakoside A (1) and chiridrakoside B (2) besides twelve known compounds comprising five phenylethanoid glycosides (3–7), two lignans (8, 9), a phenyl propanoid (10), an anthraquinone (11), a furan derivative (12) and two triterpenes (13, 14). All described compounds, except 4, 5 and 11, were obtained for the first time from the genera Chirita or Primulina. The cytotoxic activity of the isolated compounds was evaluated against the four human cancer cell lines KB (mouth epidermal carcinoma), HepG2 (hepatocellular carcinoma), Lu (lung carcinoma) and MCF7 (breast carcinoma). Epoxyconiferyl alcohol (10) exhibited cytotoxic activity against the tested cell lines (IC50 from 46 to 128 μM).
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Two alkaloids have been isolated from Z. sativa fruits besides butane-2,3-diol and glycerol. The structures of alkaloids were established as stepharine and 1,2-dimethoxy,5,6,6a,7-tetrahydro-4H-dibenzo-quinoline by using MS, NMR spectroscopic data and by comparison with reported data.
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Three terpenoid acids have been isolated from an ethyl acetate extract of Z. sativa fruits. Their structures were established as betulinic, oleanolic and maslinic acids by means of MS, NMR spectroscopic data and by comparison with reported data.