Capsinoid

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Capsinoids are alkaloid substances naturally present in chili peppers. Although they are structurally similar to capsaicin, the substance that causes pungency in hot peppers, they largely lack that characteristic. Capsinoids have an estimated "hot taste threshold" which is about 1/1000 that of capsaicin.[ citation needed ] Capsinoids were not reported in the scientific literature until 1989, [1] when biologists first isolated them in a unique variety of chili peppers, CH-19 Sweet, which does not contain capsaicin. Capsinoids include capsiate, dihydrocapsiate, and nordihydrocapsiate. [2] [3] [4]

Contents

Many health effects have been ascribed to capsaicin and capsinoids, both anecdotally and through scientific study, including anticancer, anti-inflammatory, and analgesic activities, and weight management. [5] [6] [7] [8] [9]

Structure

Structure of capsinoids, including capsiate, dihydrocapsiate, and nordihydrocapsiate. Capsinoids.svg
Structure of capsinoids, including capsiate, dihydrocapsiate, and nordihydrocapsiate.

Structural differences between capsaicin and members of the capsinoid family of compounds are illustrated below. Capsinoids have an ester bond in their structures, as compared with the amide bond characteristic of capsaicin. [2] [3]

Mechanisms of action: capsaicin vs. capsinoids

It is anecdotally said that hot peppers help people in the tropics “cool off.” This theory is consistent with the peripheral vasodilatory effect of capsaicin that has been shown to lower skin temperature in humans exposed to a hot environment. [10] Capsaicin feels hot in the mouth because it activates sensory receptors on the tongue otherwise used to detect thermal heat. [11] This receptor is called Transient Receptor Potential Vanilloid 1 (TRPV1). TRPV1 receptors are also located in the gut and in other organs. [12] Stimulation of TRPV1 receptors is known to bring about activation of the sympathetic nervous system (SNS). [13] Capsaicin has been shown to increase fat burning in humans and animals through stimulation of the SNS. [14] [15] [16]

Like capsaicin, capsinoids activate TRPV1 receptors, [17] although they are not hot in the mouth. Capsinoids cannot reach the TRPV1 oral cavity receptors, located slightly below the surface in the mouth, because of structural differences from capsaicin. On the other hand, both capsaicin and capsinoids activate TRPV1 receptors in the same manner. [17] Research has indicated that the TRPV1 receptors in the gut are important for the metabolic effects of capsaicin and capsinoids. [18]

Both energy metabolism [19] [20] and body temperature [21] [22] increases are observed in humans following extracted capsinoids or CH-19 Sweet administration. Animal studies also demonstrate these increases, as well as suppressed in body fat accumulation following capsinoids intake. [18] [23] The exact mechanisms and the relative importance of each remain under investigation, as are the effects of capsinoids on appetite and satiation. [24]

Safety testing

Purified extracts of the sweet chili pepper containing capsinoids have been extensively studied through rigorous safety tests, including evaluation of chronic toxicity, reproduction, genotoxicity, and teratology in animals, single oral administration and pharmacokinetics in humans. [25] [26] [27] [28] [29]

Capsinoids are hydrolyzed before absorption and break down to fatty acids and to vanillyl alcohol. According to human studies conducted to date, intact capsinoids are not present in the bloodstream following oral administration, [29] suggesting minimal concern about untoward activation of TRPV1 receptors in other parts of the body. Single dose oral administration of up to 30 mg capsinoids did not raise blood pressure or heart rate in healthy volunteers, [29] nor did administration of CH-19 Sweet. [22]

Major capsinoids in nature

Capsiate (4-hydroxy-3-methoxybenzyl (E)-8-methyl-6-nonenoate) (CAS No. 205687-01-0)

Dihydrocapsiate (4-hydroxy-3-methoxybenzyl 8-methylnonanoate) (CAS No. 205687-03-2)

Nordihydrocapsiate (4-hydroxy-3-methoxybenzyl 7-methyloctanoate) (CAS No. 220012-53-3)

Related Research Articles

<span class="mw-page-title-main">Scoville scale</span> Scale for measuring spiciness of peppers

The Scoville scale is a measurement of pungency of chili peppers and other substances, recorded in Scoville heat units (SHU). It is based on the concentration of capsaicinoids, among which capsaicin is the predominant component.

<span class="mw-page-title-main">Capsaicin</span> Pungent chemical compound in chili peppers

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a chemical irritant and neurotoxin for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent, crystalline to waxy solid compound.

<span class="mw-page-title-main">Chili pepper</span> Varieties of peppers belonging to several species of Capsicum genus

Chili peppers, from Nahuatl chīlli, are varieties of the berry-fruit of plants from the genus Capsicum, which are members of the nightshade family Solanaceae, cultivated for their pungency. Chili peppers are widely used in many cuisines as a spice to add "heat" to dishes. Capsaicin and related compounds known as capsaicinoids are the substances giving chili peppers their intensity when ingested or applied topically. Chili peppers exhibit a wide range of heat and flavor profiles. This diversity is the reason behind the availability of different types of paprika and chili powder, each offering its distinctive taste and heat level.

<span class="mw-page-title-main">Jalapeño</span> Hot pepper

The jalapeño is a medium-sized chili pepper pod type cultivar of the species Capsicum annuum. A mature jalapeño chili is 5–10 cm (2–4 in) long and hangs down with a round, firm, smooth flesh of 25–38 mm wide. It can have a range of pungency, with Scoville heat units of 4,000 to 8,500. Commonly picked and consumed while still green, it is occasionally allowed to fully ripen and turn red, orange, or yellow. It is wider and generally milder than the similar Serrano pepper.

<i>Capsicum pubescens</i> Species of plant

Capsicum pubescens is a plant of the genus Capsicum (pepper). The species name, pubescens, refers to the hairy leaves of this pepper. The hairiness of the leaves, along with the black seeds, make Capsicum pubescens distinguishable from other Capsicum species. Capsicum pubescens has pungent yellow, orange, red, green or brown fruits.

<i>Capsicum annuum <span style="font-style:normal;">var.</span> glabriusculum</i> Variety of chili pepper

Capsicum annuum var. glabriusculum, a chili-pepper variety of Capsicum annuum, is native to southern North America and northern South America. Common names include chiltepín, Indian pepper, grove pepper, chiltepe, and chile tepín, as well as turkey, bird’s eye, or simply bird peppers. Tepín is derived from a Nahuatl word meaning "flea". This variety is the most likely progenitor of the domesticated C. annuum var. annuum. Another similar-sized pepper, 'Pequin' is often confused with tepin, although the tepin fruit is round to oval where as the pequin's fruit is oval with a point, and the leaves, stems and plant structures are very different on each plant.

<i>Capsicum annuum</i> Species of flowering plant in the nightshade family Solanaceae

Capsicum annuum is a species of the plant genus Capsicum native to southern North America, the Caribbean, and northern South America. This species is the most common and extensively cultivated of the five domesticated capsicums. The species encompasses a wide variety of shapes and sizes of peppers, including sweet bell peppers and some chili pepper varieties such as jalapeños, New Mexico chile, and cayenne peppers, all of which are nightshades. Cultivars descended from the wild American bird pepper are still found in warmer regions of the Americas. In the past, some woody forms of this species have been called C. frutescens, but the features that were used to distinguish those forms appear in many populations of C. annuum and are not consistently recognizable features in C. frutescens species.

<span class="mw-page-title-main">Resiniferatoxin</span> Chemical compound

Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge, a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.

<span class="mw-page-title-main">TRPV1</span> Human protein for regulating body temperature

The transient receptor potential cation channel subfamily V member 1 (TRPV1), also known as the capsaicin receptor and the vanilloid receptor 1, is a protein that, in humans, is encoded by the TRPV1 gene. It was the first isolated member of the transient receptor potential vanilloid receptor proteins that in turn are a sub-family of the transient receptor potential protein group. This protein is a member of the TRPV group of transient receptor potential family of ion channels. Fatty acid metabolites with affinity for this receptor are produced by cyanobacteria, which diverged from eukaryotes at least 2000 million years ago (MYA). The function of TRPV1 is detection and regulation of body temperature. In addition, TRPV1 provides a sensation of scalding heat and pain (nociception). In primary afferent sensory neurons, it cooperates with TRPA1 to mediate the detection of noxious environmental stimuli.

<span class="mw-page-title-main">Capsazepine</span> Chemical compound

Capsazepine is a synthetic antagonist of capsaicin. It is used as a biochemical tool in the study of TRPV ion channels.

Colletotrichum capsici is a species of fungus and plant pathogen which causes leaf blight on Chlorophytum borivilianum, basil, chickpea and pepper as well as dieback in pigeonpea and anthracnose in poinsettia.

Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.

Relief from chronic pain remains a recognized unmet medical need. Consequently, the search for new analgesic agents is being intensively studied by the pharmaceutical industry. The TRPV1 receptor is a ligand gated ion channel that has been implicated in mediation of many types of pain and therefore studied most extensively. The first competitive antagonist, capsazepine, was first described in 1990; since then, several TRPV1 antagonists have entered clinical trials as analgesic agents. Should these new chemical entities relieve symptoms of chronic pain, then this class of compounds may offer one of the first novel mechanisms for the treatment of pain in many years.

Zucapsaicin (Civanex) is a medication used to treat osteoarthritis of the knee and other neuropathic pain. It is applied three times daily for a maximum of three months. Zucapsaicin is a member of phenols and a member of methoxybenzenes. It is a modulator of transient receptor potential cation channel subfamily V member 1 (TRPV-1), also known as the vanilloid or capsaicin receptor 1 that reduces pain, and improves articular functions. It is the cis-isomer of capsaicin. Civamide, manufactured by Winston Pharmaceuticals, is produced in formulations for oral, nasal, and topical use.

<span class="mw-page-title-main">Vanilloid</span> Chemical compounds containing a vanillyl group

The vanilloids are compounds which possess a vanillyl group. They include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid, homovanillic acid, capsaicin, etc. Isomers are the isovanilloids.

<i>Capsicum</i> Genus of flowering plants

Capsicum is a genus of flowering plants in the nightshade family Solanaceae, native to the Americas, cultivated worldwide for their chili pepper or bell pepper fruit.

<span class="mw-page-title-main">Phenylacetylrinvanil</span>

Phenylacetylrinvanil (IDN-5890) is a synthetic analogue of capsaicin which acts as a potent and selective agonist for the TRPV1 receptor, with slightly lower potency than resiniferatoxin, though still around 300 times the potency of capsaicin. It is an amide of vanillylamine and ricinoleic acid, with the hydroxyl group on ricinoleic acid esterified with phenylacetic acid. It is used to study the function of the TRPV1 receptor and its downstream actions, and has also shown anti-cancer effects in vitro.

<span class="mw-page-title-main">SB-705498</span> Chemical compound

SB-705498 is a drug which acts as a potent and selective blocker of the TRPV1 ion channel. It has been evaluated in clinical trials for the treatment of rhinitis and chronic cough.

References

  1. ↑ Yazawa S, et al., Content of capsaicinoids and capsaicinoid-like substances in fruit of pepper (Capsicum annuum L.) hybrids made with “CH-19 Sweet as a parent. J Jpn Soc Hortic Sci58:601-607, 1989.
  2. 1 2 Kobata, K., Todo, T., Yazawa, S., Iwi, K. and Watabe, T. (1998) Novel capsaicinoid-like substances, capsiate and dihydrocapsiate, from the fruits of a nonpungent cultivar, CH-19 sweet, of pepper (Capsicum annuum L.). Journal of Agriculture and Food Chemistry 46:1695-1697.
  3. 1 2 Kobata, K., Sutoh, K., Todo, T., Yazawa, S., Iwai, K. and Watanabe, T. (1999) Nordihydrocapsiate, a new capsinoid from the fruits of a nonpungent pepper, Capsicum annuum. Journal of Natural Products. 62:335-336.
  4. ↑ Yazawa, S., Yoneda, H., Hosokawa, M., Fushiki, T. and Watanabe, T. (2004) Novel capsaicinoid like substances in the fruits of new non-pungent cultivar CH/19 sweet of pepper (Capsicum annuum). Capsicum and Eggplant Newsletter 23:17-20.
  5. ↑ Antonio Macho, Concepción Lucena, Rocio Sancho, Nives Daddario, Alberto Minassi, Eduardo Muñoz, Giovanni Appendino. "Non-pungent Capsaicinoids from Sweet Pepper Synthesis and Evaluation of the Chemopreventive and Anticancer Potential." Eur. J. Nutr. 42 (2003): 2-9.
  6. ↑ Rocío Sancho, Concepción Lucena, Antonio Macho, Marco A. Calzado, Magdalena Blanco-Molina, Alberto Minassi, Giovanni Appendino and Eduardo Muñoz. "Immunosuppressive Activity of Capsaicinoids: Capsiate Derived from Sweet Peppers Inhibits NF-kappaB Activation and is a Potent Anti-inflammatory Compound in Vivo." Eur. J. Immunol. 32 (2002): 1753-1763.
  7. ↑ He G.-J. et al., European Journal of Medicinal Chemistry 44: 3345-3349, 2009
  8. ↑ Kawabata F. et al., Biosci Biotechnol Biochem 70:2824-2835, 2006.
  9. ↑ Sheldon Handler Ph.D., M.D.; David Rorvik: PDR for Nutritional Supplements Second Edition. Thomas Reuters; 2008.
  10. ↑ Nelson A.G. et al., Wilderness Environ Med;11:152-6, Fall 2000.
  11. ↑ Szallasi, A. and Blumberg, P.M., 1999. Vanilloid (Capsaicin) receptors and mechanisms. Pharmacology Reviews 51, 159–212.
  12. ↑ Nagy L. et al., Eur J Pharmacol 500: 351-369, 2004
  13. ↑ Iwai K. et al. Roles as metabolic regulators for the non-nutrients capsaicin and capsiate, supplemented to diet. Proc. Japan Acad., 79B (7) 207-212 (2003)
  14. ↑ Kawada T. et al., J Nutr 116:1272-1278, 1986.
  15. ↑ Kawada T. et al., Proc Soc Exp Biol Med 183:250-256, 1986.
  16. ↑ Yoshioka M. et al., British Journal of Nutrition 80: 503-510, 1998.
  17. 1 2 Iida T. et al., Neuropharmacol 44:958-967, 2003.
  18. 1 2 Ohnuki K. et al., J Nutr Sci Vitaminol 47:295-298, 2001.
  19. ↑ Snitker S. et al. Effects of novel capsinoids treatment on fatness and energy metabolism in humans: possible pharmacogenetic implications. Am, J. Clin. Nutr. 89 45-50 (2009)
  20. ↑ Inoue N. et al., Biosci Biotechnol Biochem 71: 380-389, 2007.
  21. ↑ Ohnuki K. et al., Biosci Biotechnol Biochem 65:2033-2036, 2001(a).
  22. 1 2 Sachiko Hachiya, Fuminori Kawabata, Koichiro Ohnuki, Naohiko Inoue, Hirotsugu Yoneda, Susumu Yazawa and Tohru Fushiki. "Effects of CH-19 Sweet, a Non-Pungent Cultivar of Red Pepper, on Sympathetic Nervous Activity, Body Temperature, Heart Rate, and Blood Pressure in Humans." Biosci. Biotechnol. Biochem. 71 (2007): 671-676.
  23. ↑ Ohnuki K. et al., Biosci Biotechnol Biochem 65:2735-2740, 2001.
  24. ↑ Reinbach H.C. et al., Clinical Nutrition 28: 260-265, 2009
  25. ↑ Kodama, T., E. Watanabe, T. Masuyama, S. Tsubuku, A. Otabe, M. Mochizuki, B.K. Bernard. "Studies of the Toxicological Potential of Capsinoids: II. A 26-Week Daily Gavage Dosing Toxicity Study of CH-19 Sweet Extract in Rats", Int. J. Toxicol. 27 (Suppl. 3) (2008): 11-28.
  26. ↑ Kodama, T., E. Watanabe, T. Masuyama, S. Tsubuku, A. Otabe, Y. Katsumata, B.K. Bernard."Studies of the Toxicological Potential of Capsinoids: III. A Two-Generation Reproduction Study of CH-19 Sweet Extract in Rats", Int. J. Toxicol. 27 (Suppl. 3) (2008): 29-40.
  27. ↑ Watanabe, E., T. Kodama, T. Masuyama, S. Tsubuku, A. Otabe, M. Mochizuki, M. Nakajima, S. Masumori, B.K. Bernard. "Studies of the Toxicological Potential of Capsinoids: I. Single-Dose Toxicity Study and Genotoxicity Studies of CH-19 Sweet Extract", Int. J. Toxicol. 27 (Suppl. 3) (2008): 1-10.
  28. ↑ Bernard, B.K., E. Watanabe, T. Kodama, S. Tsubuku, A. Otabe, Y. Katsumata, T. Matsuoka, T. Masuyama."Studies of the Toxicological Potential of Capsinoids: IV. Teratology Studies of CH-19 Sweet Extract in Rats and Rabbits", Int. J. Toxicol. 27 (Suppl. 3) (2008): 41-58.
  29. 1 2 3 Bernard, B.K., S. Tsubuku, T. Kayahara, K. Maeda, M. Hamada, T. Nakamura, Y. Shirai, A. Nakayama, S. Ueno, R. Mihara."Studies of the Toxicological Potential of Capsinoids: X Safety Assessment and Pharmacokinetics of Capsinoids in Healthy Male Volunteers after a Single Oral Ingestion of CH-19 Sweet Extract", Int. J. Toxicol. 27 (Suppl. 3) (2008): 137-147.
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