Synthesis of monoterpene alkaloid derivatives from the iridoid glucoside geniposide.
Nine novel monoterpene alkaloid derivatives (3(a)-(c), 4(a)-(c), 5(a)-(c)) were prepared as a reaction of genipin 2 with L-amino acid methyl hydrochlorides utilized the reaction of reductive amination. Genipin was obtained by beta-glucosidase, catalyzed hydrolysis of the iridoid glucoside geniposide 1. The chemical structures were confirmed by 1D-, 2D-NMR and MS.
Liu
Xiaohong
X
School of Pharmacy, Shandong University, Jinan, PR China.
Lou
Hongxiang
H
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D032062:Gardenia / Q000737:chemistry*; D057889:Iridoid Glycosides; D039823:Iridoids / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry* / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization
D000470:Alkaloids; D000596:Amino Acids; D057889:Iridoid Glycosides; D039823:Iridoids; D039821:Monoterpenes; D011714:Pyrans; C007835:geniposide; C007834:genipin