Sesquiterpenes from tobacco

Kodama, H., T. Fujimori, and K. Kato. Glucosides of ionone-related compounds in several Nicotiana species. Phytochemistry 1984 23(3) 583-585. Kodama, H., T. Fujimori, and K. Kato. A nor-sesquiterpene glycoside, rishitin-beta-sophoroside, from tobacco. Phytochemistry 1984 23(3) 690-692. 

Murai, A., M. Ono, and T. Masamune Structure revision of 1-keto-a -cyperone , a sesquiterpene isolated from tobacco Chem. Lett. (1978) 1005. 

R. S. Burden, J. A. Bailey and G. G. Vincent, "Glutinosone, A New Antifungal Sesquiterpene from Nicotlana glutlnosa Infected with Tobacco Mosaic Virus", Phytochemistry, lA, 221-223 (1975). 

Roberts. Vetispirane sesquiterpene glucosides from flue-cured Virginia tobacco structure, absolute stereochemistry, and synthesis. X-ray structure of the P-bromobenzenesulphonate of one of the derived aglycones. Chem Com- NT488 mun 1977 1977 27. 

The formation of the sesquiterpene (+)-5-epi-aristolochene (2) represents, from a biosynthetic point of view, the transformation requiring the fewest steps among those discussed in this review. A single enzyme, tobacco 5-epi-aristolochene synthase (TEAS), converts the biosynthetic precursor, farnesyl diphosphate (6), to... 

Figure 10.5 Plant cell cultures have proven to be very useful for studying plant-pathogen interactions and isoprenoid metabolism. Tobacco cell cultures respond rapidly to the addition of fungal elicitors (0.5 pg cellulase/ml of culture) by browning (A) (analogous to a hypersensitive response) and the production of phytoalexins (B). Media was collected from elicited cell cultures at the indicated times, partitioned against an organic solvent, and concentrated aliquots run on a silica TLC plate. The plates were then sprayed with a suspension of Cladosporium cucumerinum spores and incubated in a humid environment for 5 days before viewing (B). The compound released from the elicitor-treated tobacco cells that inhibits spore germination is capsidiol, a sesquiterpene.

VOGELI, U., FREEMAN, J.W., CHAPPELL, J., Purification and characterization of an inducible sesquiterpene cyclase from elicitor-treated tobacco cell suspension cultures, Plant Physiol., 1989,93, 182-187. 

Picaud et al. purified recombinant AMDS and determined its pH optimum to 6.5 [24]. Several sesquiterpene synthases show maximum activity in this range examples are tobacco 5-epz-aristolochene synthase [25,26], germa-crene A synthase from chickory [26] and nerolidol synthase from maize [27]. Terpenoid synthases are, however, not restricted to a pH optimum in this range. Intriguing examples are the two (-l-)-(5-cadinene synthase variants from cotton, which exhibit maximum activity at pH 8.7 and 7-7.5, respectively [28] and 8-epi-cedrol synthase from A. annua [29] with the pH optimum around... 

Hlubucek, J.R., A.J. Aasen, S.O. Almqvist, and C.R. EnzeU Tobacco chemistry. 25. Two new drimane sesquiterpene alcohols from Greek Nicotiana tabacum Acta Chem. Scand. B28 (1974) 289-294. 

A sesquiterpene phytoalexin, C17H26O4, Mr 294.39, oil, [ain -35.9° (CHCI3) formed, together with rish-itin and many other components (including vetispi-ranes), by potatoes Solarium tuberosum) after infection by the putrefactive bacterium Erwinia carotovora. Deacetylation furnishes phytuberol, C,5H240j, Mr 252.35, oil. P. can also be isolated from the culture medium of potato cell cultures after elicitation with Phy-tophthora infestans. Some sorts of tobacco Nicotiana tabacum) produce P. after infection with various Pseudomonas spp. or the tobacco mosaic virus pretreatment with a cellulase shows the same effect. 

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