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A Series of Novel Esters of Capsaicin Analogues Catalyzed by Candida antarctica Lipases

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  • Enzyme Technology and Protein Engineering
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Abstract

Capsaicin analogues are typically synthetized by condensation of the amide group of vanillylamine with a fatty acid derivative. The enzyme of choice to perform this reaction is Candida antarctica lipase B; however, this enzyme is unable to react with the phenolic substiruents of the vanillyl ring. So far, this can only be achieved chemically, resulting in capsaicin esters with higher lipophilicity and less irritation than the parent compound. In need of searching for new capsaicin derivatives, we investigated the transesterification of the phenolic OH group of capsaicin and several capsaicin analogues by Candida antarctica lipase A (CALA) with vinyl esters. Capsaicin esters were successfully synthetized with a reaction yield of 80.6% and 57.5% with vinyl butyrate and vinyl laurate, respectively. When the reactions were performed with capsaicin analogues of different acyl chain lengths, CALA exhibited a noticeable transesterification preference for medium-length capsaicin analogues. In an attempt to explore the catalytic limits of CALA, we performed the transesterification of capsaicin from Capsicum oleoresin. The results showed similar transesterification yields to those obtained with semi-pure capsaicin. Within our knowledge, this is the first report to achieve the synthesis of phenolic OH esters of capsaicin and capsaicin analogues by enzymatic means.

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Acknowledgements

This work was supported by SEP-CONACYT grant 242544-2014. T.D-V. thanks CONACYT for her doctoral fellowship. The authors would like to express their gratitude to Dr. Torres and Mr. Rosales for their generous gifts of vanillylamine hydrochloride and Capsicum oleoresin.

The authors declare no conflict of interest.

Neither ethical approval nor informed consent was required for this study.

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  1. Biotecnología Industrial, Centro de Investigación y Asistencia en Tecnología y Diseño del Estado de Jalisco, CIATEJ, 45019, Zapopan, Jalisco, Mexico

    Tania Diaz-Vidal, Juan C. Mateos-Díaz & Jorge A. Rodríguez

  2. Departamento de Ingeniería Química, Universidad de Guadalajara, 44430, Guadalajara, Jalisco, Mexico

    Luis Carlos Rosales-Rivera

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  1. Tania Diaz-Vidal
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Diaz-Vidal, T., Rosales-Rivera, L.C., Mateos-Díaz, J.C. et al. A Series of Novel Esters of Capsaicin Analogues Catalyzed by Candida antarctica Lipases. Biotechnol Bioproc E 25, 94–103 (2020). https://doi.org/10.1007/s12257-019-0290-4

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