Sesquiterpenoids from flue-cured tobacco leaves

Structures of new solanascone glucosides from flue-cured tobacco leaves.

“…NMR spectra were obtained with a Bruker AM500, and optical rotation was measured on a JASCODIP-181 polarimeter using a 5cm long quartz cell at 23°C. tabacum L., OCL)was the same as that described in the 10p-hydroxysolanascone-p-glucopyranoside tetraacetate (4 …”

Tobacco isoprenoids

“…A study of air-cured Burley tobacco has added a-curcumene 24, 8-cadinene 26, cadinenol 27, calamenene 28, cuparene 29, a-cedrene 30, cedrol 32, a-humulene 32, and p-elemene 35 to the group of ~esquiterpenoids,'~.~~ whereas y-cadinene 25, 2,3didehydrosolanascone 50, and occidol 53 are new representatives that have been obtained from flue-cured Virginia tobacco. 20 Like capsidiol 52, which is an eremophilane that had previously been found to be produced in response to infection with tobacco necrosis virus,32 several of the new tobacco sesqui terpenoids are apparently part of the defence system of members of the Solanaceae. This seems to be true for solavetivone 41 and solanascone 49, which were initially isolated from sound Burley tobacco in small a r n o u n t ~~~.…”

Oxidative Prins-Pinacol Tandem Process Mediated by a Hypervalent Iodine Reagent: Scope, Limitations, and Applications

“…Such spiro­[4,5]­decanyl scaffolds 4 are found in several natural products having interesting biological properties such as (+)-anhydro-β-rotunol 5 , an antifungal agent, (+)-dehydrosolanascone 6 , an antibacterial product resulting from a potential [2 + 2] cycloaddition process from 5 , (−)-scopadulcic acid A 7 , an antiviral agent against herpes simplex virus type 1, and (+)-magellaninone 8 , a compound belonging to the lycopodium family (Figure ).…”