New Cembranoids from Tobacco, II

Abstract

The methylethers 4-O,8-O-dimethyl-(1S, 2E, 4R, 6E, 8S, 11E)-2,6,11-cembratriene-4,8-diol (9), 4-O-methyl-(1S, 2E, 4R, 7E, 11E)-2,7,11-cembratriene-4,6-diol (4) und 4-O,6-O-methyl-(1S, 2E, 4R, 7E, 11E)-2,7,11-cembratriene-4,6-diol (8) were identified as new natural products from tobacco. They were isolated from processed tobacco as well as from leaf surface gum of fresh tobacco.The spectral data of all six methylethers of (1S, 2E, 4S, 6R, 7E, 11E)- and (1S, 2E, 4R, 6R, 7E, 11E)-2,7,11-cembratrienen-4,6-diol are given.

Cembranoids From the Leaves of Nicotiana tabacum and Their Neuroprotective Activities

“…By comparing their observed and reported spectroscopic data, 9 known compounds were determined as (1 S ,2 E ,4 S ,6 R ,7 E ,11 E )-2,7,11-cembratriene-4,6-diol ( 2 , α -CBT-diol), 8 (1 S ,2 E ,4 R , 6 E ,8 S ,11 E )-2,6,11-cembratriene-4,8-diol ( 3 ), 9 (1 S ,2 E ,4 S ,6 E , 8 S ,11 E )-2,6,11-cembratriene-4,8-diol ( 4 ), 9 4- O -methyl-(1 S ,2 E ,4 R ,6 E ,11 E )-2,7,11-cembratriene-4,6-diol ( 5 ), 10 (1 S ,2 E ,4 S ,6 E ,8 R ,11 E )-2,6, 11-cembratriene-4,8-diol ( 6 ), 9 (1 S ,2 E ,4 R ,6 R ,7 E ,11 E )-2,7,11-cembratriene-4,6-diol ( 7 , β -CBT-diol), 8 (1 S ,2 E ,4 R ,6 E , 8 R ,11 S ,12 E )-8,11-epoxy-2,6,12-cembratriene-4-ol ( 8 ), 11 (1 S ,2 E ,4 S , 6 R ,7 E ,10 S , 11 S )-10, 11-epoxy-2,7,12(20)-cembratriene-4,6-diol ( 9 ), 12 and (1 S ,2 E ,4 S ,6 R ,7 E ,10 R ,11 R )-10,11-epoxy-2,7,12(20)-cembratriene-4,6-diol ( 10 ). 12…”