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.