Stereostructure of plagiochiline A and conversion of plagiochiline A and stearoylvelutinal into hot-tasting compounds by human saliva.
The stereostructure of plagiochiline A (1) isolated from the liverwort Plagiochila fruticosa has been established by X-ray crystallographic analysis. Plagiochiline A was converted into plagiochilal B (2) and furanoplagiochilal (3) by human saliva, and stearoylvelutinal (4) isolated from the fungus Lactarius vellerus was converted into velleral (5), also by human saliva.
Hashimoto
T
T
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Tanaka
H
H
Asakawa
Y
Y
D001572:Benzofurans / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology; D001711:Biotransformation; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology; D006801:Humans; D008968:Molecular Conformation; D011714:Pyrans / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology; D012463:Saliva / Q000378:metabolism*; D013228:Stearates / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology; D013649:Taste / Q000187:drug effects*
D001572:Benzofurans; D004852:Epoxy Compounds; D011714:Pyrans; D013228:Stearates; C089886:plagiochilin A; C089885:stearoylvelutinal