Chapter 4 Constituents of Red Pepper Species: Chemistry, Biochemistry, Pharmacology, and food Science of the Pungent Principle of Capsicum Species

Suzuki, Tetsuya; Iwai, Kazuo

doi:10.1016/s0099-9598(08)60072-3

Cited by 95 publications

(92 citation statements)

References 250 publications

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“…Leete and Louden and other groups demonstrated that variable acyl moieties (Fig. 1, structures a-i) were derived from catabolism of amino acids that were subsequently elongated by the fatty acid synthase (Leete and Louden, 1968;Kopp and Jurenitsch, 1981;Suzuki and Iwai, 1984;Markai et al, 2002), a biosynthesis similar to that known for the membrane lipids of Bacillus subtilis. Congeners are found where vanillyl alcohol (Fig.…”

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confidence: 93%

“…Most prominently, they are found as sugar esters in exudates from glandular trichomes that cover the aerial epidermis of plants of the Nicotiana, Datura, Petunia, and Solanum genera (Severson et al, 1985;King et al, 1987King et al, , 1990King and Calhoun, 1988;Chortyk et al, 1997). Capsicum is not known to have glandular trichomes, but it has glandular regions in the fruit that accumulate branched fatty acids as capsaicinoids (Suzuki and Iwai, 1984;Zamski et al, 1987;Stewart et al, 2007;Fig. 2).…”

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confidence: 99%

“…These compounds are marked with asterisks. The discovery of capsaicinoids 1a to 1i has been reviewed by Suzuki and Iwai (1984). References to the other compounds are found in the text.…”

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A Dynamic Interface for Capsaicinoid Systems Biology

et al. 2009

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(M.M.J.) Capsaicinoids are the pungent alkaloids that give hot peppers (Capsicum spp.) their spiciness. While capsaicinoids are relatively simple molecules, much is unknown about their biosynthesis, which spans diverse metabolisms of essential amino acids, phenylpropanoids, benzenoids, and fatty acids. Pepper is not a model organism, but it has access to the resources developed in model plants through comparative approaches. To aid research in this system, we have implemented a comprehensive model of capsaicinoid biosynthesis and made it publicly available within the SolCyc database at the SOL Genomics Network (http://www.sgn.cornell.edu). As a preliminary test of this model, and to build its value as a resource, targeted transcripts were cloned as candidates for nearly all of the structural genes for capsaicinoid biosynthesis. In support of the role of these transcripts in capsaicinoid biosynthesis beyond correct spatial and temporal expression, their predicted subcellular localizations were compared against the biosynthetic model and experimentally determined compartmentalization in Arabidopsis (Arabidopsis thaliana). To enable their use in a positional candidate gene approach in the Solanaceae, these genes were genetically mapped in pepper. These data were integrated into the SOL Genomics Network, a clade-oriented database that incorporates community annotation of genes, enzymes, phenotypes, mutants, and genomic loci. Here, we describe the creation and integration of these resources as a holistic and dynamic model of the characteristic specialized metabolism of pepper.

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A Dynamic Interface for Capsaicinoid Systems Biology

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“…Capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide), the major pungent ingredient in red pepper, has long been used in food additives and drugs (10,11).…”

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Capsaicin Inhibits in Vitro and in Vivo Angiogenesis

Kim¹,

Han

Kim³

et al. 2004

Cancer Research

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Capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide), a natural product of Capsicum species, is known to induce excitation of nociceptive terminals involved in pain perception. Recent studies have also shown that capsaicin not only has chemopreventive properties against certain carcinogens and mutagens but also exerts anticancer activity. Here, we demonstrated the antiangiogenic activity of capsaicin using in vitro and in vivo assay systems. In vitro, capsaicin inhibited vascular endothelial growth factor (VEGF) -induced proliferation, DNA synthesis, chemotactic motility, and capillary-like tube formation of primary cultured human endothelial cells. Capsaicin inhibited both VEGF-induced vessel sprouting in rat aortic ring assay and VEGF-induced vessel formation in the mouse Matrigel plug assay. Moreover, capsaicin was able to suppress tumorinduced angiogenesis in chick chorioallantoic membrane assay. Capsaicin caused G 1 arrest in endothelial cells. This effect correlated with the down-regulation of the expression of cyclin D1 that led to inhibition of cyclin-dependent kinase 4-mediated phosphorylation of retinoblastoma protein. Signaling experiments show that capsaicin inhibits VEGFinduced p38 mitogen-activated protein kinase, p125 FAK , and AKT activation, but its molecular target is distinct from the VEGF receptor KDR/ Flk-1. Taken together, these results demonstrate that capsaicin is a novel inhibitor of angiogenesis and suggest that it may be valuable to develop pharmaceutical drugs for treatment of angiogenesis-dependent human diseases such as tumors.

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“…Consequently, in recent decades, looking for new drugs for gastric cancer treatment has been gaining more considerable research focus in many laboratories worldwide. Capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide) is a unique alkaloid found primarily in the fruit of the Capsicum genus and is what provides its spicy flavor (Cordell et al, 1993;Suzuki et al, 1994). It is a crystalline, lipophilic, colorless and odorless alkaloid with the molecular formula C 18 H 27 NO 3 , molecular weight 305.40 g/mol.…”

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Effects of Capsaicin and Its Analogs on the Growth of Gastric Cancer Cells and Their Structure-activity Relationships In Vitro

Zun-chen

Shen

et al. 2013

FSTR

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Capsaicin is an organic compound in chili peppers which are consumed by over one quarter of the world's population daily. Studies have shown that capsaicin can prohibit proliferation in some cancer cells. In the present study, both gastric cancer and normal epithelial cell lines were employed and treated with capsaicin and its analogs and examined for the structure-activity relationship as well. 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide yellow tetrazole (MTT) assay results showed the order of effectiveness of capsaicin analogs in the used cell culture system was as follows: dihydrocapsaicin > capsaicin > 6-gingerol > vanillin ≥ vanillylamine, and, reactive oxygen species (ROS) and malondialdehyde (MDA) contents were markedly increased; the biological activity pathway of Superoxide dismutase (SOD) and Glutathione Peroxidase (GSH-Px) was up-regulated, whereas, the catalase (CAT) activity was down-regulated by dihydrocapsaicin, capsaicin and 6-gingerol. In conclusion, the results implied that B and C region are indispensable for the anti-cancer activity of capsaicin and CAT activity down-regulation was responsible for apoptosis of gastric cancer cells induced by capsaicin and its analogs.

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Chapter 4 Constituents of Red Pepper Species: Chemistry, Biochemistry, Pharmacology, and food Science of the Pungent Principle of Capsicum Species

Cited by 95 publications

References 250 publications

A Dynamic Interface for Capsaicinoid Systems Biology

A Dynamic Interface for Capsaicinoid Systems Biology

Capsaicin Inhibits in Vitro and in Vivo Angiogenesis

Effects of Capsaicin and Its Analogs on the Growth of Gastric Cancer Cells and Their Structure-activity Relationships In Vitro

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