Methyl capsaicin

Solanaceae), acts as competitive inhibitor for ubiquinone in Complex I. Methyl capsaicin is more potent than capsaicin, indicating that the phenolic OH is not essential for the activity [297]. Other natural inhibitors of Complex I are annonaceous acetogenins. These compounds belong to a wide group of natural products isolated from several species of the Annonaceae family, which include more than 250 molecules with diverse chemical structures. Among the various classes, it seems that monotetrahydrofuranic derivatives are less potent than other acetogenins [296, 299]. 

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

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 hit, SB-452533, (23a) was discovered by HTS of an in-house library at GSK [86]. Compound (23a) could potently and reversibly inhibit activation of TRPVl by capsaicin, low pH and heat. Quaternization of (23a) by N-methylation afforded (24), unlikely to cross the cell membranes, but that eould nevertheless retain a certain degree of inhibitory activity on TRPVl activation. When (24) was applied intracellularly, no activity could be detected. The binding of eaps-aicin to TRPVl has traditionally been considered intracellular, but this and other observations actually suggest a more complex situation. 

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),... 

FIGURE 13.1 Methyl anthranilate deters birds from feeding and stimulates feeding in mammals. Capsaicin deters mammals from feeding but stimulates birds. 

Birds may have a trigeminal receptor for o-aminoacetophenone and methyl anthranilate, analogous to the capsaicin receptor in mammals (Clark and Shah, 1994). 

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. 

In addition to mating-disruption pheromones, there are a number of naturally occurring, nonpheromonal attractants and repellents. Many are typically used as food additives or in cosmetics or perfumes, and are derived from diverse plant and animal sources. Capsaicin [44], the spicy component of chili peppers, is used in several bird, deer, and rodent repellents. Maple lactone [45], a common food additive and flavoring, is used in traps to attract cockroaches with its stale beer odor. Methyl... 

Figure 12.6 Structures of capsaicin, maple lactone, and methyl anthranilate.

Capsaicin ( -A-[(4-hydroxy-3-methoxyphenyl)-methyl]-8-niethyl-6-nonenamide) [404-86-4]... 

Capsaicin is the most important of the capsaicinoids. Pure capsaicin, or 8-methyl-jV-vanillyl-6-nonenamide, is colourless crystals, soluble in alcohol, but insoluble in cold water, which is why drinking water helps to alleviate the burning sensation when it is eaten. 

Capsaicin, also known as N-vanillyl-8-methyl-6-(E)-nonenamide, is the most pungent among capsaicinoids that can be isolated. It is sparingly soluble in water but very soluble in fats, oils and alcohol. 

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... 

Prasad, B.C.N., Cururaj, H.B., Kumar, V., Ciridhar, P., Parimalan, R., Sharma, A. and Ravishankar, G.A. (2006) Influence of 8-methyl-nonenoic acid on capsaicin biosynthesis in in vivo and in vitro cell cultures of Capsicum spp. Journal of Agricultural and Food Chemistry 54(5), 1 854-1859. 

Capsaicin (= hmy-8-Methyl- Capsicum annuum, C.jrutescens VAN-R (e.g. Vl-R) agonist... 

Phenolic Capsaicin (= tow-8-Methyl- Sarothamnus, Spartium spp. (Fabaceae), Aconitum napellus (Ranunculaceae) Capsicum annuum (sweet pepper, stimulant, oxytocic, toxic] 4.3Cp V-K+ CH (VAN-R, V-Na+... 

Electron chains. The respiratory chain and ATP synthesis in mitochondria demand the controlled flux of electrons. This target seems to be attacked by ellipticine, pseudane, pseudene, alpinigenine, sanguinarine, tetrahydropalmatine, CH3-(CH2)i4-2,6-methyl-piperidines, capsaicin, the hydroxamic acid DIMBOA, and solenopsine. As mentioned before, however, only a few alkaloids have been evaluated in this context (Table V). 

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