Shvets S A, Gutsu O N, Kintia P K
Institute of Genetics, Academy of Science, Chisinau, Moldovia.
Adv Exp Med Biol. 1996;405:247-57. doi: 10.1007/978-1-4613-0413-5_22.
Steroidal glycosides of the spirostane and furostane series have been isolated from the methanolic extract of Nicotiana tabacum L. seeds by using gel filtration on silica gel and chromatography on a silica gel column. They were tentatively named nicotianosides A (1), B (2), C (3), D (4), E (5), F (6), and G (7). It has been shown that nicotianosides A (1), B (2), C (3), and D (4) are 3-O-beta-D-glucopyranoside-; 3-O-alpha-L-rhamnopyranosyl (1-->2)-O-beta-D-glucopyranoside-; 3-O-¿[alpha-L-rhamnopyranosyl (1-->2)].[alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside¿: 3-O-¿[alpha-L-rhamnopyranosyl (1-->2)-alpha-L-rhamnopyranosyl (1-->3)]-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside¿: neotigogenin, respectively. The structures of nicotianosides E (5), F (6), and G (7) have been established as: 3-O-alpha-L-rhamnopyranosyl (1-->2)-O-beta-D-glucopyranoside; 3-O-¿[alpha-L-rhamnopyranosyl-(1-->2)]-[alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside¿: 3-O-¿[alpha-L-rhamnopyranosyl (1-->2)-[alpha-L-rhamnopyranosyl (1-->3)]-alpha-L-rhamnopyranosyl (1-->4)]-beta-D-glucopyranoside): (25S)-5-alpha-furostane-3 beta, 22 alpha, 26-triol [-26-O-beta-D-glucopyranoside]. Growth-stimulating activities, prevention of virus attacks on tobacco, and a possible mechanism of action were established for the nicotianosides.
