Capsicum capsaicin from

Nicolazzo et al. [52] considered the use of the lipophilic skin penetration enhancers, octisalate and padimate (both used in sunscreens), in comparison to Azone on the buccal absorption of various drugs in vitro. They were found to have limited effect in enhancing the permeation of triamcinolone acetonide (although some increase in tissue uptake was proposed in some cases) relative to Azone, while reducing the penetration of estradiol and caffeine. One interesting report is that of the effect of capsaicin from capsicum, a commonly used food ingredient, which has been reported to enhance the permeability of sulfathiazole in human volunteers [53] presumably by a direct irritation effect on the mucosa. This raised an interesting issue of the effect of diet on oral mucosal permeability. 

Rizvi and Srivastava (1999) studied the protective effect of capsaicin on the osmotic fragility of human erythrocytes. Capsaicin (from capsicum) exerted a stabilizing effect on human erythrocytes, making them more resistant to lysis under hypotonic stress. The protective effect of capsaicin was due probably to a direct interaction of capsaicin with the erythrocyte membrane rather than due to any alteration in the intracellular metabolism of erythrocytes. 

Tyihak et al. validated this technique using the separation of the synthetic dyes indophenol, Sudan G, and Butter Yellow. Natural products such as capsaicin from Capsicum annum and fiirocoumarins from Heracleum sphondylium have been separated by Nyirdey et al. (14). 

Solanaceae). The active principle is capsaicin. Both capsicum resin and capsaicin are incorporated into medicines with COUNTER-IRRITANT (rubefacient or topical analgesic) actions, and when rubbed into the skin cause a feeling of warmth and that offsets the pain from underlying muscles, joints or internal organs. 

Capsaicin is the most important of a number of vanillyl fatty acid amides from capsicum, referred to as capsaicinoids, and is largely responsible for the hot pungent effect of chilies. Capsaicin causes the release of... 

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. 

The pungent principle of Capsicum was first isolated in 1876 by Tresh (1876), who assigned to it the name capsaicin. From Cayenne pepper obtained on the market Nelson (1919) isolated 12g of crude capsaicin from 40 pounds of pepper. A vanilla like odour caused by treating an alcoholic solution of capsaicin with platinic... 

Dfaz J, Pomar F, Bernal A, Merino F (2004) Peroxidases and the metabolism of capsaicin in Capsicum annuum L. Phytochem Rev 3 141-157 Dini I, Tenore GC, Dini A (2006) New polyphenol derivative in Ipomoea batatas tubers and its antioxidant activity. J Agric Food Chem 54 8733-8737 Dubey P, Khare N, Gupta PC (1982) A new flavonoid glycoside from the leaves of Ipomoea fistu-losa. Curr Sci 51 351-352... 

Capsaicin 4-en-Capsaicin Dihydrocapsaicin 5-en-7-methyl-Capsaicin FIGURE 3 Capsaicinoids from Capsicum genus (Solanaceae). 

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. 

Capsaicin (52 Qutenza , NeurogesX, 2009), an active component of chili peppers belonging to genus Capsicum, was first isolated in pure and crystalline form by John Clough Thresh in 1876." Capsaicin is currently used in topical ointments to reheve the pain of peripheral neuropathy the burning and painful sensations associated with capsaicin (capsaicin does not actually cause a chemical bum, or any direct tissue damage at all) result from its chemical interaction with sensory neurons. Capsaicin, being a member of the vanilloid family, binds to the ion channel receptor vanilloid... 

Vanillylamine [(4-hydroxy-3-methoxy-phenyl)methylamine] is the substrate of choice for the formation of vanillin with the help of amine oxidase. It can be obtained by cleavage of capsaicin (N-[(4-hydroxy-3-methoxy-phenyl)methyl]-8-methyl-6-nonenamide) isolated from pepper and capsicum [83]. As natural vanillin extracted from beans of Vanilla planifolia is rare and extremely expensive, this pathway for the production of natural vanillin is regarded to have a great potential. The vanillin obtained by the process can be labelled as natural if the cleavage of capsaicin is performed enzymatically. 

Synthesis The synthesis of capsaicin is shown below (Gannett et al., 1988). For clinical use capsaicin is isolated from chilli pepper (Capsicum annum). 

This pungent product is responsible for the intense irritant effects of topical Capsicum preparations. Repeated application of capsaicin can deplete and prevent reaccumulation of substance P, an endogenous mediator of pain impulses from the periphery to the CNS. Since the early 1990s, capsaicin cream has been available in the U.S. as an approved drug for relief of postherpetic neuralgia and pain due to diabetic neuropathy and osteoarthritis. 

Capsaicin is a bioactive molecule synthesized by enzymatic (putative capsaicin synthase) condensation of vanillylamine, a phenyl propanoid intermediate with 8-methyl-nonenoic acid, a fatty acid derivative from the leucine/valine pathway. Analysis of levels of 8-methyl-nonenoic acid and phenyl propanoid intermediates in high-, medium- and low-pungent Capsicum genotypes revealed that the 8-methyl-nonenoic acid pool plays a crucial role in determining the efficacy of capsaicin levels. Cerulenin-mediated inhibition of 8-methyl-nonenoic... 

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... 

The formation of acyl conjugates of vanillamine (capsaicinoids, 20) or vanillic alcohol (capsinoids, 21) with various Cg/Ci3 alkenoic and alkanoic acids is a unique chemical trait of plants from the genus Capsicum. Hot peppers are characterized by the presence of vanillyl conjugates of the amide type, absent or replaced by their nonpungent ester isosters (capsinoids) in bell (sweet) peppers [19]. Indeed, the difference between the sensory properties of capsaicin (la) and its naturally occurring ester analog capsiate (22) is a remarkable example of the biological relevance of isosterism. 

The combination of these elements generates the diversity of capsaicinoids reported to date. Generally, the major constituent of the capsaicinoid soup are capsaicin (la) and its dihydroderivative (lb). Commercial capsaicin potvder is an approximately 5 1 mixture of capsaicin and dihydrocapsaicin, while analytical (>95 %) capsaicin contains mainly nonivamide as impurity. Despite its trivial name of synthetic capsaicin, nonivamide is a natural trace constituent of capsicum oleoresin, and concentration >3 % are indicative of adulteration [26]. The addition of nonivamide to capsicum oleoresin has been detected in products from both the food and the pharmaceutical markets. Some of them have been found to contain exclusively nonivamide, even though capsaicin is the only individual constituent of capsicum oleoresin to be approved by the FDA for human use [26]. 

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