Biosynthesis of oleoside-, 10-hydroxyoleoside- and ligustaloside-type glucosides from secologanin

Citation
H. Kuwajima et al., Biosynthesis of oleoside-, 10-hydroxyoleoside- and ligustaloside-type glucosides from secologanin, CHEM PHARM, 47(11), 1999, pp. 1634-1637
Citations number
10
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
47
Issue
11
Year of publication
1999
Pages
1634 - 1637
Database
ISI
SICI code
0009-2363(199911)47:11<1634:BOO1AL>2.0.ZU;2-6
Abstract
A biosynthetic pathway from secologanin to oleoside-, 10-hydroxyoleoside- a nd ligustaloside-type secoiridoid glucosides was examined by feeding experi ments in which the respective C-8 stereoisomers of [8-H-3]-8,10-epoxysecolo ganin and [8-H-3]-8,10-epoxysecoxyloganin as well as [carbomethoxy-H-2(3)]s ecologanin were administered separately to three oleaceous plants. The resu lts showed that (8S)-8,10-epoxysecologanin was an intermediate between the secologanin and secoiridoid glucosides of the three types.