Structure of a cyanoglucoside of Lithospermum purpureo-caeruleum

Cyanogenic glycosides and menisdaurin from Guazuma ulmifolia, Ostrya virginiana, Tiquilia plicata, and Tiquilia canescens

“…Although the structure of menisdaurin (2) has been reported previously (Sosa et al, 1977;Takahashi et al, 1978;Nahrstedt and Wray, 1990) and the presence of long-range couplings noted, the nature and extent of coupling was not investigated, nor was a complete set of coupling constants, chemical shifts, and NOE interactions reported. This substance also was considered not to be cyanogenic (Nahrstedt and Wray, 1990), but was noted to liberate small amounts of cyanide under conditions of the ''sandwich method'' of TLC analysis in the present study and under certain other conditions (Lechtenberg and Nahrstedt, 1999).…”

“…In addition, acyclic nitrile glucosides have been reported from several families; the Rosaceae is especially important among these (Lechtenberg and Nahrstedt, 1999). Known cyclohexenylcyanomethylene structures include simmondsin (3) from jojoba [Simmondsia chinensis (Link) C. Schneider, Simmondsiaceae] (Elliger et al, 1973(Elliger et al, , 1974, bauhinin (4) [Bauhinia championii Bentham (Fabaceae)] (Chen et al, 1985) and lithospermoside (5) (Sosa et al, 1977;Wu et al, 1979). More recently, additional series of nitrile glucosides from Lophira alata Banks (Ochnaceae) (Murakami et al, 1993;Tih et al, 1994) and E. philippinensis A. DC.…”

“…Nitrile glucosides with cyclohexenylcyanomethylene structures are found in other boraginaceous species, such as Lithospermum purpureocaeruleum L. and Lithospermum officinale L. (Sosa et al, 1977) and Ehretia philippinensis (Simpol et al, 1994).…”

Modern strategy for new medicine research: study of pharmacological activities of riachin, a non-cyanogenic cianoglycoside extracted from Bauhinia pentandra

“…The basic structure of this class has been set [15] and characterized later as a non-cyanogenic cianoglicosídeo [16], but under specific conditions may release a small amount of cyanide [17].…”

Lithospermum Species

“…Various amino acids were detected, as were 0.03% scyllitol and bornesite. A cyanogenic glycoside was isolated and identified [1]. Gallotannins and tannins of the catechin type were also found.…”