Capsaicinoids in peppers

Balbaa, S. I., Karawya, S., Grrgis, A. N. (1968) Uoydia, 31, 272-274. (a) For recent studies on the distribution of capsaicinoids in pepper plants, see Kirshbaum-Titze, P., Mueller-Seitz, E., Petz, M. (2002) Journal of Agricultural and Food Chemistry, 50, 1260-1263. (b) Kirshbaum-Titze, P., Mueller-Seitz,... 

Barbero, G. R, Pahna, M., and Barroso, C. G. 2006. Determination of capsaicinoids in peppers by microwave-assisted extraction-highperformance liquid chromatography with fluorescence detection. Anal. Chim. Acta 578 227-233. 

Thomas, B. V., Schreiber, A. A., and Weisskopf, C. P. 1998. Simple method for quantitation of capsaicinoids in peppers using capillary gas chromatography. J. Agric. Food Chem. 46 2655-2663. 

Quantitative analysis of capsaicinoids in peppers and pepper spray products)... 

I. Perucka and W. Oleszek, Extraction and determination of capsaicinoids in fruit of hot pepper Capsicum annuum L. by spectrophotometry and high-performance liquid chromatography. Food Chem. 71 (2000) 287-291. 

The nitrogenous compounds produced in pepper fruit, which cause a burning sensation, are called capsaicinoids. Capsaicinoids are purported to have antimicrobial effects for food preservation [46], and their most medically relevant use is as an... 

Analysis of chemical constituents in fruits of red pepper (cv. Bugang) revealed five natural capsaicinoids. They were capsaicin, nordihydrocapsaicin, dihydrocapsaicin, vanillyl decanamide and homodihydrocap-saicin. The concentration of total capsaicinoids in fruits was 5.4mg/100g FW. Eleven carotenoids were identified, with a total concentration of 65 mg/100g FW. The con-... 

Reilly, C.A., Crouch, D.J. and Yost, G.S. (2001) Quantitative analysis of capsaicinoids in fresh peppers, oleoresin capsicum and pepper spray products. Journal of Forensic Sciences 46(3), 502-509. 

Saga, K. and Sato, G. (2003) Varietal differences in phenolic, flavonoid and capsaicinoid contents in pepper fruits (Capsicum annuum L.). Journal of the Japanese Society for Horticultural Science 72(4), 335-341. 

Since hot pepper is important for the food and the pharmaceutical industries, a range of different methods have been developed for the analysis of capsaicinoids in plant material and finished products. The separation of CPS (la) and nonivamide (11) is especially challenging, since these compounds have similar behavior in many chromatographic conditions. Since synthetic nonivamide is the most common adulterant of capsicum oleoresin, various strategies have been suggested to overcome this problem. Capillary GC does not require previous derivatization of capsaicinoids, but its separatory power seems lower than that of HPLC, currently the most popular technique for the quantization of capsaicinoids. GC is, however, the method of choice for the analysis of the acyl moieties of capsaicinoids as methyl esters. These can be directly produced from capsaicinoids by oxidative N-dealkylation with DDQ (2,3-dichloro-5,6-dicyanobenzoquinone), followed by alcoholysis of the resulting amides with methanol in the presence of an acidic resin (Scheme 4.4) [41]. 

The availability of sophisticated analytical methods to separate and quantify capsaicinoids, has made it possible to study their distribution and kinetics of formation. Capsaicinoids are unevenly distributed in pepper plants and fruits. 

Source and Composition. OC is an oily reddish-brown extract of pepper plants of the genus Capsicum, principally from Capsicum an-nuum and Capsicum frutescens. Depending on the variety of the chilli pepper, OC contains from 0.01 to 1.0% capsaicinoids on a dry mass basis. The extract is a complex mixture of fat-soluble phenols (capsaicinoids), some of which are listed in Table 4. The composition of OC is highly variable and depends on factors such as the conditions of extraction, maturity of the fruit and environmental conditions in which the Capsicum plants were grown. Thus, the capsaicinoid content of extracts used in pepper spray varies between manufacturers (1.2-12.6% Smith and Stopford, 1999). Capsaicin and dihydrocapsaicin make up to 80-90% of the total capsaicinoids in OC extract. 

Table 4. Some capsaicinoids in extract of pepper plants (Capsicum annuum and Capsicumfrutescen.es) (with approximate % in extract and CAS numbers) ...

Disease resistance in peppers is correlated with the presence of capsaicin, although other compounds, such as the sesquiterpene capsidiol, may also be involved. In animals, these compounds produce strong irritation and inflammation of the skin, mucous membranes, and eyes, and can even be fatal if large doses are given at one time. In smaller doses, capsaicin stimulates the flow of digestive juices and has a laxative effect on the colon. Consumption of capsaicinoids causes increases in respiration and vasoconstriction and ele-... 

The main objectives of this chapter are to gain widespread knowledge on Capsicum and its extracted compounds, which are responsible for its pungent taste. This chapter includes a brief description on the extraction and various biological activities of the capsaicinoids isolated from pepper fruits. The chapter has also focused on the clinical applications and recent advances in the study of these capsaicinoids compounds. A detailed discussion of UPLC-MS technique used for the separation and determination of capsaicinoids in various capsicum species is also presented. 

The UAE technique is based on the employment of the energy derived from ultrasounds that facilitate the extraction of analytes from the solid sample by the organic solvent [66]. The enhancement of extraction efficiency of organic compounds by UAE is attributed to the phenomenon of cavitation produced in the solvent by the passage of ultrasonic waves [67]. The uses of higher temperatures in UAE lead to an increase in the efficiency of the extraction process [67-69]. The ultrasound-assisted extraction of capsaicinoids from pepper has also been carried out by Barbero et al. in... 

Perucka and Oleszek have reported extraction and determination of capsaicinoids in fresh fruit of hot pepper using spectrophotometry and HPLC techniques [79]. Cooper et al. developed a reversed-phase HPLC method utilizing a conventional Cjg column to separate capsaicin, dihydrocapsaicin, and nordihydrocapsaicin present in hot peppers [121]. The isocratic mobile phase (60 40 [v/v] methanol/water at a flow rate of 1.5 mL/min) was employed and achieved the separation of these three capsaicinoids in 28 min [121]. Krajewska and Power developed a reversed-phase HPLC... 

Table 10.4 Influence of technological processing on the content of capsaicinoids in Jalapeho peppers.

Capsaicin, also known as N-Vanillyl-8-methyl-6-(E)-noneamide, is the most pungent of the group of compounds called capsaicinoids It is a common ingredient in varieties of pepper such as habanero, Thai, tabasco, cayenne etc. One target with which capsaicin interacts is the capsaicin receptor, an ion channel belonging to the superfamily of TRP channels. Because of the structural relation to other TRP channels and because the vanilloid moiety is an essential component of capsaicin, the capsaicin receptor is also called TRPVI or vanilloid receptor (VR1). It is involved in heat and pain perception. 

The pungent components of chili peppers belong to a class of substances known as capsaicinoids. The most pungent and most common substance in this family is capsaicin (Fig. 7.2.1) (N-[4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide). Other members of this family include dihydrocapsaicin (Fig. 7.2.2), nodihydrocapsaicin (dihydrocapsaicin with a (CH2)s linkage instead of (CH2)6),... 

Because of their complementary character, TLC and HPLC can be used simultaneously for the easier solution of complicated separation problems. Thus, the determination of cap-saicinoids in fruit of hot pepper Capsicum annuum L. by spectrophotometry, TLC and HPLC has been reported. Samples were homogenized with acetone followed by a homogenization with acetone-petroleum ether 1 1 v/v until the tissue was nearly white. The extract was filtered and the acetone was washed out by small amounts (0.01 ml) of water. The ether phase was dried with anhydrous NajSC and concentrated in vacuum at 30°C. The extract was separated on silica TLC plates using a petroleum ether-acetate-methanol (75 20 5) mobile phase. The capsaicinoids were scraped off the layer and further analysed by HPLC. The Rp values of carotenoids and capsaicinoids are listed in Table 2.2. It was stated that the method can be employed for the measurement of carotenoids in hot peppers [19]. 

Screening for no-heat mutants in Capsicum collections and populations is a common practice for pepper breeders, as capsaicinoid accumulation is unique to the members of genus. A second locus for control of capsaicinoid production exists in at least two other species, C. chinense and C. chacoense [82], and the mutation that revealed this second locus is called loss of vesicle (Lov). The blisters on the placental surface that fill with capsaicinoids are absent in these no-heat mutants. The gene product and map location of this mutation are not known. 

Although most consumers appreciate the fieriness of chile, capsaicinoids are not perceived through odor or taste receptors but through the nociceptive pain receptors described earlier. The compounds in chile fruit that create the flavor and aroma are produced in the fruit wall. Buttery et al. [90] generated vacuum steam distilled oil from green bell pepper macerate, with well over 40 peaks on subsequent GC/MS analysis. Of these peaks, the major flavor compound associated with bell pepper aroma was 2-methoxy-3-isobutylpyrazine (Fig. 8.1). They also reported several monoterpenoids in abundance, limonene, trans- 3-ocimene, and linalool as well as other aliphatic aldehydes and ketones. The flavor composition of dried red bell pepper powder (sweet paprika) extracted with ether identified 44 key peaks by GC/MS [91]. In these dried samples the key compounds were P-ionone and several furanones. The post-harvest processing and the different fruit maturities as well as possible varietal differences are all causes for the different aromatic profiles. 

Hall R, Holden M, Yeoman M (1987) The accumulation of phenylpropanoid and capsaicinoid compounds in cell cultures and whole fruit of the chili pepper, Capsicum frutescens MiU. Plant Cell Tissue Organ Cult 8 163-176... 

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