Pungent principles

Many spices are processed (2) to produce essential oils, oleoresins, essences, tinctures, extracts, resinoids, etc. These processes separate nonflavor components and further concentrate the aromatic or pungent principles of the spices. Such products allow a wider variety of uses and appHcations of the vital spice components. 

The chemistry of pepper has long been studied and the pungent principle of black pepper—a piperidine alkaloid, piperine 134—was isolated as early as 1877 (201). Its synthesis from the acid and piperidine was accomplished in 1882. (202). The corresponding pyrrolidine alkaloid trichostachyne (135) was isolated some 100 years later from several Piper species (see below). The cooccurence of piperidine and pyrrolidine alkaloids is a common feature of the chemistry of pepper. In many cases, the crude alkaloid extract is first cleaved with acids or bases and then each alkaloid is reconstituted by selective amidation. For the sake of unity, this chapter will be limited to comments on pyrrolidines, even in cases where they are minor alkaloids. 

Vanillin is the starting point for several chemicals. Thus capsaicin, the pungent principle of red pepper (Capsicum annuum), used in pepper-spray and pain killing ointments, is made in two steps from vanillin. 

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... 

Iwai K, Lee K-R, Kobashi M, Suzuki T (1977) Formation of pungent principles in fruits of sweet pepper, Capsicum annuum L. var. grossum during post-harvest ripening under continuous light. Agric Biol Chem 41 1873-1876... 

ZO024 Park, K. K., K. S. Chum, ]. M. Lee, S. S. Lee, and Y. ]. Surh. Inhibitory effects of [6]-gingerol, a major pungent principle of ginger, on phorbol ester-induced inflammation, epidermal ornithine decarboxylase activity and skin tumor promotion in ICR mice. Cancer Lett 1998 129(2) 139-144. 

ZO107 Denniff, P., and D. A. Whiting. Bio-synthesis of (6) gingerol, pungent principle of Zingiber officinale. Chem Commun 1976 711. 

Clark. Pungent principles of ginger Z0139 (Zingiber officinale) are thermogenic in the perfused rat hindlimb. Int J Obesity 1992 16 755-763. 

Nomura, H. Pungent principles of ginger. I. A new ketone, zingiberone, 20319 occuring in ginger. Sci Rep Tohoku ImpUnivl917 6 41-52. 

Fujioka, and K. Shiraki. Studies on the pungent principles of ginger (Zingiber officinale) by GC-MS (gas chromatog-raphy-mass spectrometry). Yakugaku Z0321 Zasshi 1973 93(3) 318-321. 

Nelson, E.K. Constitution of capsaicin, the pungent principle of ginger. II. 

In the cyclopentanoid monoterpene family, compounds containing an iridoid-structure exhibit various bioactivities in Nature. For example, dehydroiridodiol, isolated from dry leaves of the cat-attracting plant Actinidia polygama Miq., is known to be an attractant for the male adults of the Chrysopidae and shows activity in amounts as small as lO"" pg [35]. Dehydroiridodial, a more oxidized product, was isolated as a pungent principle of Actinidia polygama Miq. and was characterized by T. Sakan et al. in 1978 [36]. 

Since piperine (Pi) is universally accepted as the predominant pungent principle in pepper, the quality of pepper and oleoresin is dependent largely on its content, and so methods for estimat-... 

DeCleyn and Verzele (3Q.3J-.32) isolated the four possible isomers from piperinic acid irradiated in an ultra-violet reactor, by counter-current distribution and also the piperidides obtained synthetically from the treated piperinic acid by high pressure liquid chromatography (figure 4). The structures of the isomers were derived mainly from NMR data. Their pungency was recorded, but possibly not by rigorous methods (31.32). The results confirmed the observation of Grewe t ail. (29) that piperine is the pungent principle of pepper, and that other isomers have little taste. ... 

The pungent principles of commercial Japanese ginger have been studied by two groups of workers who found [6]-gingerol to be the major constituent, together with smaller quantities of [8]- and [10]-gingerols (Chen et al., 1986). 

He et al. (1998) developed a gradient elution reversed-phase HPLC technique for separation of pungent principles. HPLC-UV-electrospray MS was used successfully to identify the individual pungent constituents in the chromatogram of ginger extract. Seven compounds were identified positively as the major pungent constituents of... 

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