Capsaicin analogue

In 1990, specific binding of [ H]resiniferatoxin (2, RTX), an ultrapotent capsaicin analogue isolated from the latex of the cactus-like plant Euphorbia resinifera, provided the first direct proof for the existence of a distinct capsaicin receptor [4]. Based on the chemical motif (a vanillyl moiety) shared by (1) and (2), this receptor was termed the vanilloid receptor VRl [1]. 

Capsaicin analogues that differ in only one functional group affect birds and mammals differently. A change from an acidic phenolic hydroxyl group in vanil-lyl acetamide to a methoxy group in veratryl acetamide reverses the effect on starlings and rats. The first was aversive to starlings, but attractive to rats, while the opposite was true for veratryl acetamide (Mason etal., 1991). 

Capsaicin.—It is known that phenylalanine acts as the source of the vanillylamine moiety of capsaicin (132) in Capsicum annuum and that valine (136) is used for the construction of the acyl part.2 It has been noted107 that whilst radioactive valine (136) was incorporated into capsaicin (132) and its dihydro-derivative (133), L-[U-14C]leucine [as (137)] labelled the capsaicin analogues (134) and (135) in Capsicum fruits both amino-acid precursors were very considerably better incorporated into capsaicinoid metabolites by using spheroplasts prepared from the placentas of Capsicum fruits. or-Ketoisovaleric acid (138) and cr-ketoisocaproic acid... 

Olvanil [inn, usan] (/V-vanillyloleamide) is a capsaicin analogue regarded as a vanilloid receptor AGONIST. It can be... 

There is evidence indicating that the structure-activity requirements for excitation and inhibition are different for capsaicin analogues. Thus, the incorporation of certain long chain fatty acids in capsaicin analogues resulted in desensitising and analgesic activity but also decreased pungency. [56]. 

Urban [20] described a capsaicin-analogue compound (SDZ 249-665), with antinociceptive and anti-hyperalgesic activity as well as reduced pungency. In addition, it does not cause bronchoconstriction or changes in blood pressure. 

Andrews, P.L.R. and Bhandari, P. (1993) Resiniferatoxin, an ultra potent capsaicin analogue, has antiemetic properties in the ferret. Neuropharmacology 32 799-806. 

Sana, A., Lembeck, F., and Skofitsch, G. 1981. Determination of capsaicin analogues by high performance liquid chromatography. J. Chromatogr. 208 41 6. 

The first competitive TRPVl antagonist is capsazepine (3), a conforma-tionally constrained (9-demethyl thiourea analogue of capsaicin that emerged from a programme aimed at the optimization of the agonistic properties of capsaicinoids [66]. The second competitive antagonist to be... 

Fujiwake H, Suzuki T, Iwai K (1982) Intracellular distributions of enzymes and intermediates involved in biosynthesis of capsaicin and its analogues in Capsicum fruits. Agric Biol Chem 46 2685-2689... 

Iwai K, Suzuki T, Fujiwake H (1979) Formation and accumulation of pungent principle of hot pepper fruits, capsaicin and its analogues in Capsicum annuum var. annuum cv. Karayatsubusa at different growth stages after flowering. Agric Biol Chem 43 2493-2498... 

Suzuki T, Kawada T, Iwai K (1981) The precursors affecting the composition of capsaicin and its analogues in the fruits of Capsicum annuum var. annuum cv. Karayatsubusa. Agric Biol Chem 45 535-537... 

Suzuki T, Fujiwake H, Iwai K (1980) Intracellular localization of capsaicin and its analogues, capsaicinoid, in Capsicum fruit. 1. Microscopic investigation of the structure of the placenta of Capsicum annuum var. annuum cv. Karayatsubusa. Plant Cell Physiol 21 839-853 Ohta Y (1963) Physiological and genetical studies on the pungency of Capsicum IV. Secretory organ, receptacles and distribution of capsaicin in the Capsicum fruits. Jap J Breed 12 179-183... 

Mason, J. R., Bean, N. J. Shah, P. S., and Clark, L. (1991). Taxon-specific differences in responsiveness to capsaicin and several analogues correlates between chemical structure and behavioral aversiveness. Journal of Chemical Ecology 17, 2539-2552. 

Campbell, E., Bevan, S., Drary, A. (1993). Clinical applications of capsaicin and its analogues. In Capsaicin in the Study of Pain (J. Wood, ed.), pp. 255-69. Harcourt Brace Co., London. 

Pelargonyl vanillamide, PAVA. Synthetic analogue of capsaicin qv. 

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