Glycosides of 2-C-methyl-D-erythritol from the fruits of anise, coriander and cumin.
Eight glycosides of 2-C-methyl-D-erythritol (1) were isolated from the fruit of anise, and their structures were clarified as 1-O-beta-D-glucopyranoside, 3-O-beta-D-glucopyranoside, 4-O-beta-D-glucopyranoside, 1-O-beta-D-fructofuranoside, 3-O-beta-D-fructofuranoside, 4-O-beta-D-fructofuranoside, 1-O-beta-D-(6-O-4-hydroxybenzoyl)-glucopyranoside and 1-O-beta-D-(6-O-4-methoxybenzoyl)-glucopyranoside of 2-C-methyl-D-erythritol (2-9), respectively. Furthermore, 2 and 4 were isolated from the fruit of coriander, and 2, 3 and 4 were isolated from the fruit of cumin. Though the phosphate of 1 was known to be one of the first precursors of isoprenoids in the non-mevalonate pathway, and 1 is considered to be a common constituent in Umbelliferous plants, the glycosides of 1 are found for the first time.
Kitajima
Junichi
J
Showa Pharmaceutical University, Higashi-Tamagawagakuen 3, Machida, Tokyo 194-8543, Japan. kitajima@ac.shoyaku.ac.jp
Ishikawa
Toru
T
Fujimatu
Eiko
E
Kondho
Kyoko
K
Takayanagi
Tomomi
T
D028526:Coriandrum / Q000737:chemistry*; D028527:Cuminum / Q000737:chemistry*; D004896:Erythritol / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification*; D005638:Fruit / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D028042:Pimpinella / Q000737:chemistry*
D006027:Glycosides; C043904:3-C-methylerythritol; D004896:Erythritol