An unusual stress metabolite induced by CuCl(2) and other constituents from the leaves of Chloranthus anhuiensis

A 6-eremophilene derivative 2 with an unusual pendant was produced as phytoalexin in the fresh leaves of Chloranthus anhuiensis K. F. Wu in response to abiotic stress elicitation by CuCl(2). The phytoalexin was characterized as a sesquiterpene with a (2,6-dimethoxy-4-hydroxy)benzyl moiety pendant. Two new Sesquiterpenes, (3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid (1) and (3R,4S,5R,6R,8R,10S)-3,6,8-trihydroxy-7(11)-eremophilen-12,8-olide (3), one new sesquiterpene glycoside, anhuienoside A (4), one new caffeoyl phenylethanoid diglycoside with an unusual cyclic structure, anhuienoside B (5), and one new tyramine derivative, N-acetyltyramine 1-O-beta-d-glucoside (6), and three known compounds were also isolated. Their structures and relative configurations were established by spectroscopic means. The absolute configurations of 1-3 were defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra.