Formation of long-chain <i>N</i>-vanillyl-acylamides from plant oils

Kobata, Kenji; Takemura, Ikue; Tago, Gaku; Moriya, Takayuki; Kubota, Kaori; Nakatani, Sachie; Wada, Masahiro; Watanabe, Tatsuo

doi:10.1080/09168451.2014.912118

Cited by 3 publications

(10 citation statements)

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“…N-AVAM capsaicin analogues have been generated by the nucleophilic amidation reaction using vanillylamine (12) and plant oils. 30 The yield of the N-AVAM capsaicin analogues depended upon the fatty acid composition of the plant oil used in the reaction. The compound 12 was mixed with olive oil and the resultant mixture was heated to 180 °C for 1 h to generate a mixture of N-AVAM capsaicin analogues (3−7, Scheme 3).…”

Section: Isolation Of N-avam Capsaicinmentioning

confidence: 99%

“…It is probable that natural N-AVAM capsaicin analogues in Capsaicum oleoresin were evolutionarily generated from the reaction of 12 and the oils found in the oleoresin. 29,30 3.3. Chemical Synthesis of N-AVAM Capsaicin Analogues.…”

Section: Isolation Of N-avam Capsaicinmentioning

confidence: 99%

“…29 The reaction of 12 with olive oil (catalyzed by lipase B, lipase D, lipase R, or Novozym435) yielded 5. 30 When safflower oil was used in the above reaction, the product obtained was a mixture of 5 and 6. Similarly, lipase-catalyzed reaction of 12 with perilla oil generated 7.…”

Section: Isolation Of N-avam Capsaicinmentioning

confidence: 99%

“…Similarly, lipase-catalyzed reaction of 12 with perilla oil generated 7. 30 The rate limiting step of this lipase-catalyed synthesis of 5 was the release of 12 from its hydrochloride salt (Scheme 13). Reyes-Duarte et al increased the efficacy of the lipase-catalyzed reaction by adding DIPEA along with vanillylamine hydrochloride salt (24).…”

Section: Isolation Of N-avam Capsaicinmentioning

confidence: 99%

“…N-AVAM capsaicin analogues have been generated by the nucleophilic amidation reaction using vanillylamine ( 12 ) and plant oils . The yield of the N-AVAM capsaicin analogues depended upon the fatty acid composition of the plant oil used in the reaction.…”

Section: Preparation Of N-avam Capsaicin Analoguesmentioning

confidence: 99%

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Nonpungent N-AVAM Capsaicin Analogues and Cancer Therapy

et al. 2021

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Capsaicin displays robust growth-inhibitory activity in multiple human cancers. However, the feasibility of capsaicin as a clinically relevant anticancer drug is hampered by its adverse side effects. This concern has led to extensive research focused on the isolation and synthesis of second-generation nonpungent capsaicin analogues with potent antineoplastic activity. A major class of nonpungent capsaicin-like compounds belongs to the N-acyl-vanillylamide (N-AVAM) derivatives of capsaicin (hereafter referred as N-AVAM capsaicin analogues). This perspective discusses the isolation of N-AVAM capsaicin analogues from natural sources as well as their synthesis by chemical and enzymatic methods. The perspective describes the pharmacokinetic properties and anticancer activity of N-AVAM capsaicin analogues. The signaling pathways underlying the growth-inhibitory effects of N-AVAM capsaicin analogues have also been highlighted. It is hoped that the insights obtained in this perspective will facilitate the synthesis of a second generation of N-AVAM capsaicin analogues with improved stability and growth-suppressive activity in human cancer.

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Section: Isolation Of N-avam Capsaicinmentioning

confidence: 99%

Section: Isolation Of N-avam Capsaicinmentioning

confidence: 99%