Cytotoxicity of capsaicin and its analogs <i>in vitro</i>

Santos, V. A. M.; Bressiani, P. A.; Zanotto, A. W.; Almeida, I. V.; Berti, A. P.; Lunkes, A. M.; Vicentini, V. E. P.; Düsman, E.

doi:10.1590/1519-6984.268941

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Brazilian Journal of Biology

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Original Article • Braz. J. Biol. 83 • 2023 • https://doi.org/10.1590/1519-6984.268941 copy

Cytotoxicity of capsaicin and its analogs in vitro

Citotoxicidade da capsaicina e seus análogos in vitro

Authorship SCIMAGO INSTITUTIONS RANKINGS

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.

Keywords:
biological activity; Capsicum; MTT assay; pepper; pungency

Compound	Modification in the vanillyl ring	Size of the acyl chain	Abbreviation
Capsaicin (8-methyl-N-vanylyl-6-nonenamide)	X₁= MeO -	R= C₉H₁₇	CAP
	X₂= HO -
N-Benzylbutanamide	X₁= H -	R= C₃H₇	AN1
	X₂= H -
N-(3-methoxybenzyl) butanamide	X₁= MeO -	R= C₃H₇	AN2
	X₂= H -
N-(4-hydroxy-3-methoxybenzyl) butanamide	X₁= MeO -	R= C₃H₇	AN3
	X₂= HO -
N-(4-hydroxy-3-methoxybenzyl) hexanamide	X₁= MeO -	R= C₅H₁₁	AN4
	X₂= HO -
N-(4-hydroxy-3-methoxybenzyl) tetradecanamide	X₁= MeO -	R= C₁₃H₂₇	AN5
	X₂= HO -

Groups	VC [%]
	CAP		AN1		AN2		AN3		AN4		AN5
	24 h	48 h	24 h	48 h	24 h	48 h	24 h	48 h	24 h	48 h	24 h	48 h
CO-	100.00	100.00	100.00	100.00	100.00	100.00	100.00	100.00	100.00	100.00	100.00	100.00
CO+	34.83	29.74	57.27	40.45	55.84	58.27	76.64	77.59	75.04	69.76	35.62	6131
10 μM	88.04	90.63	112.58	104.64	79.31	59.10	93.33	100.71	91.93	109.00	87.83	60.16
25 μM	89.51	111.41	100.52	109.63	80.34	64.18	87.78	98.25	92.31	105.43	63.62	64.84
50 μM	90.10	113.15	102.68	91.58	74.36	68.67	97.56	100.95	86.57	108.53	63.35	51.03
75 μM	86.84	111.43	104.38	106.87	81.43	70.79	94.63	101.19	86.96	106.22	79.31	73.30
100 μM	80.93	137.77	103.18	95.16	86.56	77.83	96.26	104.23	92.97	113.43	74.62	76.16
125 μM	84.05	115.30	96.98	95.95	78.75	88.26	94.60	104.05	86.28	111.03	66.86	70.50
150 μM	80.28	114.87	99.89	84.89	82.78	93.15	92.39	102.78	90.39	118.66	83.72	58.94
175 μM	77.94	114.36	95.28	77.55	88.50	99.73	87.21	97.12	79.50	118.87	90.71	70.62
200 μM	74.99	123.83	101.89	87.35	84.51	112.80	100.00	102.60	93.35	119.43	71.82	73.11

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