A novel amino acid glycoside and three amino acids from Allium sativum.
A novel amino acid glycoside (-)-N-(1'-deoxy-1'-beta-D-fructopyranosyl)-S-allyl-L-cysteine sulfoxide [1], was isolated from a hydrophilic extract of the leaves of Allium sativum (Alliaceae), together with three known compounds: (+)-S-allyl-L-cysteine sulfoxide [2],(+)-S-methyl-L-cysteine sulfoxide [3], and (+)-S-(trans-1-propenyl)-L-cysteine sulfoxide [4]. The latter two substances were isolated for the first time from garlic. The structure elucidation of 1 was performed by extensive chemical, spectroscopic (ir, fabms, 1D and 2D(1)H- and (13)C-nmr measurements) and chromatographic experiments. For the first time, detailed nmr data and the unambiguous assignment of all (13)C-nmr data for compounds 2-4 were reported. Compound 1, the amino acid glycoside, revealed a significant inhibition of in vitro platelet aggregation induced by ADP and epinephrine, whereas none of the amino acids tested displayed any activity.
Mütsch-Eckner
M
M
Department of Pharmacy, Swiss Federal Institute of Technology, Zurich, Switzerland.
Erdelmeier
C A
CA
Sticher
O
O
Reuter
H D
HD
D000596:Amino Acids / Q000302:isolation & purification* / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000302:isolation & purification / Q000494:pharmacology; D005737:Garlic / Q000737:chemistry*; D006027:Glycosides / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010946:Plants, Medicinal; D010974:Platelet Aggregation / Q000187:drug effects; D010975:Platelet Aggregation Inhibitors / Q000302:isolation & purification / Q000494:pharmacology
D000596:Amino Acids; D000890:Anti-Infective Agents; D006027:Glycosides; D010975:Platelet Aggregation Inhibitors