Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

Kobata, Kenji; Kawaguchi, Manami; Watanabe, Tatsuo

doi:10.1271/bbb.66.319

Cited by 53 publications

(42 citation statements)

References 29 publications

(35 reference statements)

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“…Capsaicinoids were synthesized by the condensation of vanillylamine hydrochloride with the corresponding acyl chlorides in dry pyridine (Rangoonwala and Seitz, 1970). Capsinoids were synthesized enzymatically (Kobata et al, 2002). The purity of all compounds was confirmed to be over 95% by reversed phase HPLC.…”

Section: Methodsmentioning

confidence: 99%

Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1

et al. 2006

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Section: Methodsmentioning

confidence: 99%

Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1

et al. 2006

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“…8 As a control solution, we used the capsiate vehicle, that is, a solution containing 0.9% NaCl, 3% ethanol and 10% Tween 80 as described elsewhere. 9 During a 14-day period, animals were daily administrated per os with the control or the capsiate (100 mg kg À1 body weight) solution.…”

Section: Experimental Protocolsmentioning

confidence: 99%

Capsiate administration results in an uncoupling protein-3 downregulation, an enhanced muscle oxidative capacity and a decreased abdominal fat content in vivo

et al. 2009

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Objectives: The involvement of skeletal muscle mitochondrial uncoupling protein-3 (UCP3) in the control of energy expenditure in skeletal muscle and at the whole-body level is still a matter of debate. We previously reported that UCP3 downregulation is linked to an enhanced mitochondrial energy metabolism in rat skeletal muscle as a result of acute capsiate treatment. Here, we aimed at investigating noninvasively the effects of chronic capsiate ingestion on metabolic changes occurring in exercising gastrocnemius muscle and at the whole-body level. Methods: We used an original experimental setup allowing a complete noninvasive investigation of gastrocnemius muscle function in situ using 31-phosphorus magnetic resonance spectroscopy. Whole-body fat composition was determined using magnetic resonance imaging and UCP3 gene expression was measured by quantitative real-time RT-PCR analysis. Results: We found that a 14-day daily administration of capsiate (100 mg kg À1 body weight) reduced UCP3 gene expression and increased phosphocreatine level at baseline and during the stimulation period in gastrocnemius muscle. During muscle stimulation, pH i showed a larger alkalosis in the capsiate group suggesting a lower glycolysis and a compensatory higher aerobic contribution to ATP production. Although the capsiate-treated rats were hyperphagic as compared to control animals, they showed a lower weight gain coupled to a decreased abdominal fat content. Conclusion: Overall, our data indicated that capsiate administration contributes to the enhancement of aerobic ATP production and the reduction of body fat content coupled to a UCP3 gene downregulation.

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“…Because capsiate is scarcely present in natural foods, enzymatic synthesis of capsiate by lipase-catalyzed acylation of vanillyl alcohol with fatty acid derivatives has been attempted (Kobata et al 2002). In lipase-catalyzed acylation, an acyl donor (8-methyl-trans-6-nonenoic acid; an acyl moiety in the capsiate molecule) is first synthesized chemically (Crombie et al 1955) or is prepared by hydrolysis of capsaicin (Kobata et al 2002).…”

Section: Introductionmentioning

confidence: 99%

“…In lipase-catalyzed acylation, an acyl donor (8-methyl-trans-6-nonenoic acid; an acyl moiety in the capsiate molecule) is first synthesized chemically (Crombie et al 1955) or is prepared by hydrolysis of capsaicin (Kobata et al 2002). However, because these procedures required separate preparation of the acyl donor, we investigated a one-procedure synthesis of capsiate from capsaicin.…”

Section: Introductionmentioning

confidence: 99%

One-procedure synthesis of capsiate from capsaicin by lipase-catalyzed dynamic transacylation

Ishihara

Kwon

Masuoka

et al. 2010

World J Microbiol Biotechnol

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Capsiate has a structure similar to capsaicin but no oral pungency. Furthermore, capsiate displayed antioxidant activity and inhibited angiogenesis and vascular permeability, and therefore, showed potential as a medicine and food supplement. Capsaicin is now commercially available, however capsiate is scarcely present in natural foods. We investigated the direct enzymatic conversion of a capsaicinoid to a capsinoid. It was observed that the rate of lipase-catalyzed acylation of vanillyl alcohol with nonanoic acid was faster than that of hydrolysis of N-vanillylnonanamide to vanillyl amide and nonanoic acid in n-hexane at 70°C. As a result, we performed a one-procedure synthesis of capsiate from capsaicin via lipase-catalyzed transacylation.

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Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

Cited by 53 publications

References 29 publications

Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1

Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1

Capsiate administration results in an uncoupling protein-3 downregulation, an enhanced muscle oxidative capacity and a decreased abdominal fat content in vivo

One-procedure synthesis of capsiate from capsaicin by lipase-catalyzed dynamic transacylation

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