Isolation and identification of two new diterpene glycosides from Nicotiana tabacum.
Two new diterpene glycosides containing 20-hydroxygeranyllinalool were isolated and identified from Nicotiana tabacum. These compounds consisted of five molecules of glucose and/or rhamnose. The locations of the aglycone and glycosides in the molecules were determined by 2D-NMR with the HMBC technique. The structures were (6E,10E,14Z)-20-hydroxygeranyllinalyl-3-O- [alpha-L-rhamnopyranosyl (1 --> 4)]-beta-D-glucopyranoside-20-O- [beta-D-glucopyranosyl (1 --> 2)]-[alpha-L-rhamnopyranosyl (1 --> 6)]-beta-D- glucopyranoside and (6E,10E,14Z)-20-hydroxygeranyllinalyl-3-O- [alpha-L-rhamnopyranosyl (1 --> 4)]-beta-D-glycopyranoside-20-O- [alpha-L-rhamnopyranosyl (1 --> 4)]-[alpha-L-rhamnopyranosyl (1 --> 6)]-beta-D- glucopyranoside.
Shinozaki
Y
Y
Product Technology Development Division, Japan Tobacco Inc., Tokyo, Japan.
Tobita
T
T
Mizutani
M
M
Matsuzaki
T
T
D002240:Carbohydrate Sequence; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D008970:Molecular Weight; D010936:Plant Extracts / Q000302:isolation & purification / Q000378:metabolism; D010947:Plants, Toxic; D014026:Nicotiana / Q000737:chemistry*
D004224:Diterpenes; D006027:Glycosides; D010936:Plant Extracts