Cytotoxicity of capsaicin and its analogs in vitro

Abstract

Capsaicin (CAP) is the main compound responsible for the spicy flavor of Capsicum plants. However, its application can be inhibited due to its pungency and toxicity. This study aimed to evaluate and compare the cytotoxic effect of CAP and its analogs N-benzylbutanamide (AN1), N-(3-methoxybenzyl) butanamide (AN2), N-(4-hydroxy-3-methoxybenzyl) butanamide (AN3), N-(4-hydroxy-3-methoxybenzyl) hexanamide (AN4) and N-(4-hydroxy-3-methoxybenzyl) tetradecanamide (AN5) on the hepatoma cells of Rattus norvegicus using the MTT test. The results showed cytotoxicity of CAP at concentrations of 100, 150, 175, and 200 μM (24 hours), AN1 at 150 and 175 μM (48 hours), AN2 at 50 μM (24 hours) and 10, 25, 50, and 75 μM (48 hours), AN4 at 175 μM (24 hours), and AN5 at 50 μM (48 hours). Removing the hydroxyl radical from the vanillyl group of capsaicin, together with reducing the acyl chain to 3 carbons, which is the case of AN2, resulted in the best biological activity. Increasing the carbon chain in the acyl group of the capsaicin molecule, which is the case of AN5, also showed evident cytotoxic effects. The present study proves that the chemical modifications of capsaicin changed its biological activity.

Pharmacological activity of capsaicin: Mechanisms and controversies (Review)

“…The Indian population consumes several-fold more chili than populations in other countries, yet this does not appear to adversely affect growth, organ weight, nitrogen balance or blood chemistry ( 93 ). Previous studies in animals and mammalian cell lines have not suggested any mutagenic effects of capsaicin in somatic cells or the germline ( 94 ). Capsaicin cream has been used in the clinic for numerous years to relieve various types of pain, and long-term local application of capsaicin can be effective for treating skin cancer in mice ( 28 , 50 , 95 – 98 ).…”

Two New Amides from Physochlainae Radix

“…These compounds exhibit anti-inflammatory, antioxidant, immunomodulatory, and anti-tumor effects. [8][9] In this article, two new amides with an unusual (2formyl-5-hydroxymethyl)pyrroyl-butylamine moiety (1-2) were obtained from Physochlainae Radix (Figure 1). The isolation, structure elucidation were described below.…”

Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines

“…The broad applicability of capsaicin (8-methyl- N -vanillyl-6-nonenamide) and capsaicin analogues in the food, pharmacy, and health industry has led to a renewed interest in these compounds (Abdel-Salam 2014 ; Basith et al 2016 ; Santos et al 2023 ). Among the spectrum of applications, perhaps the most promising one is the apoptotic effect of capsaicin in several human cancer cell lines such as KB (Lin et al 2013 ), prostate cancer (Mori et al 2006 ), and glioblastoma cells (Lee et al 2000 ; Szoka and Palka 2020 ).…”