Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim.

Isoflavonoids, an interesting and restricted group of secondary metabolites of legumes, exhibit estrogenic, antiangiogenic, and anticancer activities and are now popular as dietary supplements. Plant cell cultures that possess an increased ability to synthesize these metabolites were examined. During the investigation, cell cultures of the Far Eastern relict tree Maackia amurensis (Leguminosae) were established. A selection of seed-derived cell aggregates yielded the callus line designated A-18. This culture produces 20 isoflavonoids, namely, the isoflavones genistein, daidzein, formononetin, calycosin, derrone, and pseudobaptigenin and their glycosylated conjugates genistin, 6''-O-malonylgenistin, ononin, 6''-O-malonylononin, daidzin, 3'-methoxydaidzin, 4'-O-beta-D-glucopyranosyldaidzin, 4'-O-beta-D-glucopyranosylgenistin, and 7-O-beta-D-glucopyranosylcalycosin; the pterocarpans maackiain and medicarpin and their glycosylated conjugates 6'-O-malonyl-3-O-beta-D-glucopyranosylmaackiain and 6'-O-malonyl-3-O-beta-D-glucopyranosylmedicarpin; and the new pterocarpan glucoside 6'-O-malonyl-3-O-beta-D-glucopyranosyl-6,6a-dehydromaackiain. These isoflavonoids, possessing a hepatoprotective activity, were stably produced by the A-18 calli for prolonged periods of observation.

Caffeic acid metabolites from Eritrichium sericeum cell cultures.

Eritrichium sericeum (Boraginaceae) callus and root cultures were established and analyzed for caffeic acid metabolite (CAM) production. Two substances, (-)-rabdosiin and rosmarinic acid, were identified as main CAMs produced by these cultures. The E. sericeum Er-1 root culture accumulated up to 1.5 % and 4.5 % DW of (-)-rabdosiin and rosmarinic acid, respectively. Rabdosiin in the Lithospermum erythrorhizon callus cultures was produced exclusively as the (+)-enantiomer while in both Eritrichium cultures it occurred as the (-)-enantiomer. The E. sericeum Er-1 culture accumulated 3-fold higher levels of CAMs than the L. erythrorhizon culture. A new compound, named eritrichin, was isolated from the cultured E. sericeum cells. The structure of this compound was established as (2R)-3-(3,4-dihydroxyphenyl)-2-[4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-naphthoyloxy]propanoic acid on the basis of spectral data.