Capsidiol

Other common phytoalexins in food materials are pisatin, cinnamylphenols, glyceolin, phaseolin [13401 -40-6] (14), and 5-deoxykieritol in peas, beans, soybeans, and lima beans viniferin in grapes momilactones and ory2alexins in rice a-tomatine in tomato lubimen in eggplant and capsidiol in green peppers. 

F. Ewing. 5-Epi-aristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol. Phytochemistry 1989 28(3) 775-779. Borys, D. J., S. C. Setzer, L. J. Ling. CNS depression in an infant after the ingestion of tobacco A case report. Vet Hum Toxicol 1988 30(1) 20-22. Deutsch, H. M., K. Green, and L. H. Zalkow. Water soluble high molecular weight components from plants with potent intraocular pressure lowering activity. Curr Eye Res 1987 6(7) 949-950. 

Capsidiol - [FLAVORS AND SPICES -SPICES] (Vol 11) - [FOOD TOXICANTS, NATURALLY OCCURRING] (Vol 11) - [FUNGICIDES,AGRICULTURAL] (Vol 12)... 

Fig. 2 Biosynthetic route to terpenes. Geranyl diphosphate (5) famesyl diphosphate (6) gera-nylgeranyl diphosphate (7) (-)-limonene (8) (-)-camphene (9) taxadiene (10) casbene (II) capsidiol (12). IPP = isopentenyl diphosphate, DMAPP = dimethylallyl diphosphate...

Fig. 4 Synthesis of (+)-5-epi-aristolochene (2) from the natural product capsidiol (12)...

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.

Figure 10.11 A proposed pathway for the biosynthesis of capsidiol in elicitor-treated tobacco cell cultures. Earlier work had not resolved how 5-epi-aristolochene, synthesized from FPP by the action of 5-epi-aristolochene synthase, was converted to capsidiol.

Figure 10.12 Gas chromatograms of the reaction products formed upon incubation of microsomes isolated from yeast over-expressing a tobacco terpene hydroxylase gene (panels A C) (CYP71D20) or harboring only the expression vector DNA (control) (B D). Microsomes were incubated with 5-epi-aristolochene (A B) or 1-deoxycapsidiol (C D) in the presence (blue line) or absence (red line) of NADPH. 5-epi-aristolochene, 1-deoxycapsidiol and capsidiol were all verified by MS.58...

Whitehead, I.M., Threlfall, D.R., Ewing, D.F., 5-epi-aristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol, Phytochemistry, 1989,28,775-779. 

Bicyclic sesquiterpenes include a variety of bioactive compounds including the Solanaceae phytoalexins capsidiol (G61G6) from Capsicum frutescms (pepper) and the Solanum tuberosum (potato) antifungals rishitin (G61C6) and solavetivone (G6-G5) the Ipomoea batatus... 

Capsidiol Mcotiana sylvestris [elicited cultured COX (PCS) [phytoalexm,... 

Keller, H., Czernic, P, Ponchet, M., Ducrot, P.H., Back, K., Chappell, J., Ricci, P. and Marco, Y. (1998a) Sesquiterpene cyclase is not a determining factor for elicitor-induced and pathogen-induced capsidiol accumulation in tobacco. Planta, 205, 467-76. 

Direct-defense compounds can be either constitutively present in (specific parts of) the plant or be produced after induction by pathogens or herbivores. The latter compound will be less costly for the plant. For example, elicitor-induced accumulation of the antimicrobial sesquiterpenoid capsidiol correlated with the induction of 5-ept-aristolochene synthase, which is a branch-point sesquiterpene cyclase involved in the synthesis of sesquiterpene phytoalexins (8). In rice Oryza saliva L.), 14 diterpenoid phytoalexins have been identified. All these compounds are accumulated in rice leaves after inoculation with the... 

A new HPLC technique has been developed for the rapid analysis of sesquiterpene phytoalexins such as capsidiol, rishitin, luminin, and phytuberol. This method employs a cyanopropyl-bonded phase column with an isocratic mixture of hexane and isopropanol. Flame ionization and UV detection were used for the analysis of capsidiol, rishitin, lubimin, phytuberol, and debneyol. Although both detectors proved to be useful, the signal response with the flame ionization detector was proportional to the mass of each of the phytoalexins, while the signal with the UV detector was proportional to the number of carbon—carbon bonds in each of the compounds. 

An investigation of the metabolism of sesquiterpenoid phytoalexins has shown that pepper or potato cell cultures can convert capsidiol (485) and rishitin (450) into their 13-hydroxy-derivatives cf. p. 136). Solavetivane derivatives of this type have previously been isolated from flue-cured tobacco (Vol. 8, p. 107). New chemical and spectroscopic evidence has led to a revised configuration for the 3-hydroxy- or 3-acyloxy-substituent in furanofukinol (486) (Petasites japonica Maxim.) and the related esters (487) and (488), previously isolated from Farfugium hiberniflorum Kitam. ... 

Gordon et al.,71 have reported the isolation of capsidiol (143) an antifungal compound which is produced by the fruit of sweet peepers in response to inoculation with fungi Recently Bailey et al.,72 have isolated capsidiol (143) from Nicotiana tabacum and Nicotiana clevelandii following infection with tobacco necrosis virus. (TNV) It has been assigned the following structure... 

The biological investigations on capsidiol show that the results obtained are very similar to those obtained with various legumes74 and with Nicotiana glutinosa. These results provide further evidence that tissues which are necrotic as a result of infection with virus generally contain antifungal compounds. Therefore probably from sweet pepper capsidiol was isolated71 as phytoallexin. Thus capsidiol may have similar... 

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