• Journal of Applied Biological Chemistry
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• v.44 no.2
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• pp.84-86
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• 2001

Capsaicin synthesis by suspension cultured cells of Jalapeno pepper (Capcicum annuum L.) was assessed in vitro under various conditions including temperature (23 and $30^{\circ}C$), light intensity (with light and without light), and shaking speed (110 and 200 rpm). Capsaicin production increased, while the cell biomass growth decreased possibly due to the production of a secondary metabolite. Capsaicin synthesis was primarily affected by light condition. Cells cultivated at 110 rpm and $23^{\circ}C$ under light condition yielded the highest fresh weight, while those cultivated under the same condition, but without light resulted in the lowest cell mass. Capsaicin content in cells of 18-day-old pepper grown at 110 rpm and $23^{\circ}C$ under light was 0.125% of the cell mass. However, without light treatment, the capsaicin content in cells at the same shaking speed and temperature increased up to 169%, indicating no light is favored in the capsaicin synthesis by Jalapeno pepper. Increasing the shaking speed from 110 to 200 rpm without light enhanced the capsaicin synthesis. Results of this study demonstrate that light condition is the limiting factor in the synthesis of capsaicin in tissue-cultured Jalapeno pepper cells.

• Archives of Pharmacal Research
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• v.19 no.3
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• pp.246-247
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• 1996

In the previous reports (Park et al., 1991, and 1993), we described the synthesis and analgesic effects of various homovanillic amides as analogs of capsaicin. In the study, we tried to enhance the analgesic actvity of capsaicin by structural modification. Our study has been performed in three directions. First, the amide bond of capsaicin was transposed. Second, a phenyl ring was introduced to replace a double bond of capsaicin. Finally, aminoethylation was performed on 4-hydroxy group of capsaicin to improve oral bioavailability. These studies have led to N-(3-phenylpropyl)homovanillic amide 2 which has high analgesic activity. Our continuing efforts in this area have focused on the introduction of various substituents on the phenyl ring of 2 as well as their pharmacological studies. We report herein the synthesis of homovanillic amide derivatives and their analgesic activity.

• Bulletin of the Korean Chemical Society
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• v.20 no.7
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• pp.857-859
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• 1999

• Biomolecules & Therapeutics
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• v.5 no.1
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• pp.94-99
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• 1997

Capsaicin is known to be an analgesic agent, affecting the synthesis, storage, , transport and release of substance p, the principal neurotransmitter of pain from periphery to the central nervous system(CNS). DA-5018, a newly synthesized capsaicin derivative has shown potent analgesic effect comparable to that of morphine in various rat models of experimentally inducted acute pairs. In this study the mechanism of analgesic actlvity of DA-5018 was examined. First, the electrically-evoked contraction of guinea pig trachea was inhibited by DA-5018 and these inhibition was recovered by incubation with capsafepine(3$\muM$), capsaicin receptor antagonist and this result suggested that DA-5018 has affinity on capsaicin receptor. The correlation between the norciceptive threshold and the release of substance P was evaluated. In vivo perfusion of slices of the rat spinal cord with DA-5018(10, 100$\muM$) produced a significant increase of the release of substance P and this increase was less than that of capsaicin(10$\muM$). The norciceptive threshold of rat treated with DA-5018(1 mg/kg, p.o) in tall pinch test increased from 2.9$\pm$0.3 to 23.5 $\pm$6.61. Tail pinch latency increased to a maximun at 15 min after DA-5018 treatment and then declined to control values by 120 min. The capsaicin-evoked release ot substance P from the spinal cord slices of rat treated with DA-5018 reduced from 2.38$\pm$ 0.79 to 0.69$\pm$ 0.26 pg/mg wet weight. This reduction reached to a minium at 15 min after DA-5018 treatment and then recovered to control value by 120 min. These results mean that analgesic activity of DA-5018 is due to release of substance P The effect of DA-5018 cream on electrically-evoked neurogenic inflammation of rat saphenous nerve was compared with capsaicin (zostrix-HP). DA-5018 showed 34% inhibition of the neurogenic extravasation while capsaicin showed significant 67% inhibition. This result indicates that the potency of DA-5018 in the release of substance P is less than that of capsaicin. These results suggest that the release of substance P is partially involved in the mechanism of analgesic action of DA-50l8.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.364.2-364.2
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• 2002

(S) and (R) 12-HETE. endogenous eicosanoids. have recently been discovered to be implicated in a number of important biological activities. In particular. it has recently been reported by us that both the capsaicin-activated channel of sensory neurons and the cloned capsaicin receptor (VR1) are activated by the eicosanoids including these metabolites. We report herein a novel and efficient asymmetric synthesis of highly enantiomerically enriched 12(S)-HETE via enzymatic kinetic resolution of the key allylic alcohol synthon. (omitted)

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.339.3-340
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• 2002

Capsaicin is hot taste ingredient of chili pepper and was isolated in 1876 and in 1919 its structure is sympathized compound. induces pain and when persistently dosed. the fact will bring insensible condition to other chemical and mechanical thermal stimulation by incapacitating sensory neuron is known. The analgesic effect by desensitization of such capsaicin is differ from the mechanism by analgesic action by opiate receptor of the existing analgesia or by prostaglandin mediation and the efficacy was known as similar with morphine. (omitted)

• Journal of the Korean Association of Oral and Maxillofacial Surgeons
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• v.50 no.2
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• pp.63-69
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• 2024

This current systematic review aimed to evaluate the current evidence on the effect of topical capsaicin application to alleviate symptoms related to burning mouth syndrome (BMS). PubMed, Ovid SP, and Cochrane were searched from 1980 to 2022 to identify relevant literature. A total of 942 titles (PubMed, 84; Ovid SP, 839; Cochrane, 19) was retrieved, of which 936 were excluded based on the title and abstract. A total of 11 studies were further evaluated for full text analysis, of which 7 were excluded. As a result, 4 articles were included for qualitative synthesis of data. Capsaicin as a mouthwash can have potential application in the treatment of symptoms related to burning mouth. The quality of available studies is moderate to low, and a well-designed randomized multicentric study comparing capsaicin with other active agents is planned to obtain more definitive conclusions.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.355.1-355.1
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• 2002

Recently. we have reported that several lipoxygenases products directly activate the capsaicin-activated channel as intracellular messengers in neuron. In particular, 12-(S)-hydroperoxyeicosatetraenoic acid turned out to be the most potent endogenous VR activator. This finding prompted us to search for a novel non-vaniloid VR agonists and antagonists. We have designed and synthesized a series of non-vanilloid VR binding ligands based on the structural simllarity between 12-HPETE and capsaicin, the natural VR agonist. Our recent studies on the development of selective vanilloid receptor agonists and antagonists will be presented.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.244.1-244.1
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• 2003

Advances in understanding of pain and analgesia have been made. Over the past few years, we have designed and synthesized a series of VR agonists, based on the structures of 12-HPETE and capsaicin. the natural VR agonist. But for the development of analgesic drugs, these synthetic VR agonists had problems like burning sensation. hypothermia. etc. So our recent studoes have focused on designs and syntheses of VR antagonists based on the structure of capsaicin(natural VR agonist), and capsazepine(synthetic VR antagonist). (omitted)

• Applied Biological Chemistry
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• v.14 no.1
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• pp.29-34
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• 1971

Changes in hot-taste component during the after-ripening period of hot pepper fruit were surveyed and summarized as follows; (1) Capsaicinoid contents were steadily increased as the after-ripening proceeded when physiological activity of the sample was suppressed during each stage of the ripening with the vacuum dry freezing. (2) It was assumed by determining phenylalanine contents and activities of phenylalanine ammonialyase to see synthetical process of capsaicin in the metabolic part of vanillylamine that there is a gradual synthesis and accumulation of capsaicin during the after-ripening period. (3) Lignin-like substances, as in the case of capsaicinoid, showed a steady increase during the after-ripening period. (4) The contents of polyphenolic compounds and polyphenol oxidase activity were higher with low temperature treatment.