New Acylated Cyanogenic Diglycosides from Fruits of Anthemis cairica.

Three new cyanogenic diglycosides of the mandelonitrile series have been isolated from fruits of ANTHEMIS CAIRICA (Compositae) and their structures identified by degradation and spectral methods mainly (1)H-NMR, (13)C-NMR, FAB-MS. Minor compounds are 2-beta-primeverosyloxy-2-phenyl-2S-acetonitrile (epilucumin) and its 4''-p(beta-D-glucopyranosyloxyl-(E)cinnamate; the main compound is the 4''-p(beta-primeverosyloxy)-(E)cinnamate of epilucumin.

Gynocardin and tetraphyllin B from Carpotroche brasiliensis.

Gynocardin and Tetraphyllin B were isolated from the seeds and pericarp of Carpotroche brasiliensis (Raddi) Endl. (Flacourtiaceae). The cyanogenic glycosides occur in an approximately equimolar mixture in the seeds and in the pericarp. Their structures were confirmed by (1)H-NMR.

[The occurrence of hydrocyanic acid in Cormophytes. 18th. Communication. New observations in leguminosae-Papilionoideae (Galegeae, Genisteae, Loteae, Phaseoleae)]. / Die Verbreitung der Blausäure bei den Cormophyten.

Cyanogenesis in Galegeae, Genisteae, Loteae and Phaseoleae, four tribes of Leguminosae-Papilionoideae, is discussed thoroughly. Oxytropis campestris (Galegeae) is shown to be facultatively cyanogenic (table I); cyanophoric plants contain a zierin-like glucoside. Lotononis crumaniana (Genisteae) is strongly cyanogenic and contains prunasin. Lotaustralin, accompanied by up to 5% Linamarin was demonstrated to be present in three taxa belonging to Dorycnium pentaphyllum sensu lato (table I). Leaves and stems of Phaseolus lunatus contain linamarin and perhaps trace amounts of lot-australin, but no taxiphyllin- or dhurrin-type glucosides.

[Distribution of hydrocyanic Acid in cormophyta: 15.1 new observations on cyanogenesis in Rosaceae]. / Die Verbreitung der Blausäure bei den Cormophyten.

Prunasin was isolated from leaves and roots of Aruncus silvester (= A. dioicus), leaves of Gillenia trifoliata and seedlings of Kageneckia lanceolata (all Spiraeoideae). Chamaebatiaria millefolium (Spiraeoideae - Sorbarieae) was found to be cyanogenic; in this instance the cyanogenic constituent seems to be different from prunasin, however. Prunasin was isolated also from buds and very young shoots of Crataegus irrasa (Maloideac - Crataegeae). Very young leaves of Crataegus cuneata and C. pedicellata also contain prunasin-like glycosides. Adenostoma fasciculatum, A. sparsifolium, all taxa of Cercocarpus tested and Coleogyne ramosissima were shown to have more or less strongly cyanogenic leaves. Together with Kerria, Neviusia and Rhodotypos these genera deviate from true Rosoideae by being cyanogenic and by having the basic chromosome number 9 instead of 7. The cyanogenic compounds of these taxa seem not to be derived from phenylalanine. Prinsepia uniflora (Prunoideae) has cyanogenic young shoots which do not contain prunasin or a similar compound. Within the species Aruncus silvester, Sorbus aria and Sorbus aucuparia cyanogenesis of leaves was found to be a highly variable character. The taxonomic meaning of cyanophoric compounds in Rosaceae is discussed briefly.