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Original Article • Braz. J. Biol. 82 • 2022 • https://doi.org/10.1590/1519-6984.267856 copiar

Caracterização espectral e avaliação biológica de biomoléculas das cascas de três frutos de laranja: um estudo comparativo

Autoria SCIMAGO INSTITUTIONS RANKINGS

Resumo

O presente trabalho almejou investigar a presença de produtos químicos bioativos nas misturas de reação (MRs) de cascas de Valência, Tangerina e laranja umbigo africana, por meio de estudos de GC-MS e FT-IR. Assim, constatou-se que limoneno, um composto único, está presente nos RMs das três cascas de laranja. Além disso, o éster 2-hidroxi-1-(hidroximetil) etílico do ácido hexadecanóico foi identificado nos RMs de todas as cascas de três laranjas. A RM da tangerina exibiu potente efeito citotóxico contra células de câncer de mama humano (HBC) MCF-7 ATCC. Todos os três RMs exibiram atividade antibacteriana moderada contra as bactérias patogênicas humanas dos seguintes tipos: Staphylococcus aureus (ATCC 25923), Staphylococcus epidermidis (ATCC 12228), Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC 25922), Klebsiella pneumoniae (ATCC 700603), Salmonella choleraesis (ATCC 10708), Pseudomonas aeruginosa (ATCC 27853) e Proteus mirabilis (ATCC 299).

Palavras-chave:
frutas; laranjas; componentes bioativos; citotoxicidade; antibacterianos

S.no	Compound name	Molecular formula	Molecular weight	Retention time (Min)	Probability Index	Percent area of curve
1	Limonene	C₁₀H₁₆	136	19.21	25.93	32.87
2	9-Octadecenamide, (Z)-	C₁₈H₃₅NO	281	86.50	87.91	1.75
3	Hexadecanoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl	C₁₉H₃₈O₄	330	90.51	64.76	0.84
4	Octadecanoic acid, 2-hydroxy-1- (hydroxymethyl)ethyl	C₂₁H₄₂O₄	358	95.22	71.90	0.31
5	Tetradecanamide	C₁₄H₂₉NO	227	78.62	37.17	0.78
6	Hexadecanamide	C₁₆H₃₃NO	255	71.40	29.96	0.78
7	Ethyl iso-allocholate	C₂₆H₄₄O₅	436	67.33	16.08	0.58
8	Ethyl α-d-glucopyranoside	C₈H₁₆O₆	208	59.82	39.88	0.32
9	d-Glycero-d-galacto-heptose	C₇H₁₄O₇	210	52.90	10.78	0.78
10	α-Sitosterol	C₂₉H₅₀O	414	114.34	38.33	0.1
11	Vitamin E	C₂₉H₅₀O₂	430	108.02	66.17	0.1
12	4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-	C₂₀H₂₀O₇	372	109.57	79.05	0.1

S.no	Compound name	Molecular formula	Molecular weight	Retention time (Min)	Probability Index	Percent area of curve
1	Limonene	C₁₀H₁₆	136	19.27	16.70	36.31
2	Octadecanoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl	C₂₁H₄₂O₄	358	95.22	55.79	0.78
3	Hexadecanoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl	C₁₉H₃₈O₄	330	90.51	63.90	1.5
4	Tetradecanamide	C₁₄H₂₉NO	227	78.65	47.55	0.92
5	n-Hexadecanoic acid	C₁₆H₃₂O₂	256	71.41	78.31	0.74
6	α-D-Mannofuranoside, 1-O-(10-undecenyl)-	C₁₇H₃₂O₆	332	65.70	27.79	0.31
7	3-Deoxy-d-mannoic lactone	C₆H₁₀O₅	162	58.62	65.30	0.30
8	Desulphosinigrin	C₁₀H₁₇NO₆S	279	51.26	17.77	0.8
9	2-Methoxy-4-vinyl phenol	C₉H₁₀O₂	150	41.09	58.27	0.32
10	Decanal	C₁₀H₂₀O	156	33.04	42.10	0.12
11	Vitamin E	C₂₉H₅₀O₂	430	108.01	53.86	0.08
12	1-Monolinoleoylglycerol trimethylsilyl ether	C₂₇H₅₄O₄Si₂	498	107.77	35.34	0.02

S.no	Compound name	Molecular formula	Molecular weight	Retention time (Min)	Probability Index	Percent area of curve
1	Limonene	C₁₀H₁₆	136	19.29	19.98	39.06
2	Hexadecanoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl	C₁₉H₃₈O₄	330	90.51	65.93	1.25
3	9,12-Octadecadienoic acid (Z,Z)-, methyl ester	C₁₉H₃₄O₂	294	74.93	31.57	0.64
4	Terephthalic acid, di(2-ethylhexyl) ester	C₂₄H₃₈O₄	390	95.60	35.24	0.14
5	α-Sitosterol	C₂₉H₅₀O	414	114.33	40.06	0.15
6	α-D-Glucopyranose, 4-O-α-D-galactopyranosyl-	C₁₂H₂₂O₁₁	342	51.90	11.86	0.12
7	2-Methoxy-4-vinylphenol	C₉H₁₀O₂	150	41.07	66.82	0.27
8	Eugenol	C₁₀H₁₂O₂	164	44.52	27.97	0.14
9	cis-Vaccenic acid	C₁₈H₃₄O₂	282	76.88	18.68	1.00
10	Decanal	C₁₀H₂₀O	156	33.05	49.18	0.14
11	Vitamin E	C₂₉H₅₀O₂	420	108.02	48.07	0.16
12	Dichloroxylenol	C₈H₈C_l2O	190	46.67	53.36	0.12

Wave number (cm^-1)	Intensity Estimation	Functional Groups/Class	Compounds
3327	Strong	O-H str. (hydroxyl)	Glycosides, Flavonoids, Saponins, Polysaccharides, Lignin
2946	Strong	C-H str. (Alkene)	Limonene, beta-Sitosterol, Lignin, Aliphatic chains present in the lignocellulose,
2946	Strong	C-H str. (Aldehyde/ketones)
2834	Strong	CH₂ str. (Symmetrical)	Aliphatic compounds, beta-Sitosterol
2834	Strong	CH₂ str. (Symmetrical)	Saponins, Fatty acids
1649	Strong	C=O str (Carboxylic group)	Fatty amides (Hexadecanamide, 9-Octadecenamide, (Z) etc.), Pectin, Lignin, Flavonoids, Proteins, Fatty acids
		C=C str (Aromatic)
		C=C str (Alkenes)	Sitosterol, Limonene
1450	Medium	C-H (Asymmetrical bending)	Flavonoids, Limonene
1320	Weak	CH₂ bend (Alkane, Symmetrical)	Steroidal glycosides, Flavonoids, Saponins, hexose sugars
1110	Strong	C-O-C str (Ether, Ester)	Glycosides, Pectin, Polysaccharides, Lignin, Cellulose, Flavonoids
1017	Strong	C-O str.	Glycogens

Wave number (cm^-1)	Intensity Estimation	Functional Groups/Class	Compounds
3331	S	O-H str. (hydroxyl)	Eugenol, Vitamin E, Glycosides, Flavonoids, Saponins, Lignin, Polysaccharides, Glucopyranose, Dichloroxylenol
2944	S	C-H str. (Alkene)	Limonene, beta-Sitosterol, Lignin, Aliphatic chains present in the lignocellulose, Vitamin E
2944	S	C-H str. (Aldehyde/ketones)
2833	S	CH₂ str. (Symmetrical)	Aliphatic compounds, beta-Sitosterol, Saponins, Fatty acids, Vitamin E
1654	S	C=O str (Carboxylic & Aldehyde group)	Fatty amides (Hexadecanamide, 9-Octadecenamide, (Z), Vaccenic acid etc.), Decanal, Pectin, Lignin, Flavonoids, Sitosterol, Limonene, Proteins, Fatty acids, Esters, Eugenol
		C=C str (Aromatic)
		C=C str (Alkenes)
1449	M	C-H (Asymmetrical bending)	Limonene, Flavonoids
1300	W	CH₂ bend (Alkane, Symmetrical)	Steroidal glycosides, Saponins, hexose sugars, Flavonoids
1115	S	C-O-C str	Glycosides, Polysaccharides, Lignin, Cellulose, Flavonoids, Tocopherol, Glucopyranose, Pectin
1018	S	C-O str	Eugenol, Glycogens

Wave number (cm^-1)	Intensity Estimation	Functional Groups/Class	Compounds
3331	S	O-H str. (hydroxyl)	Vitamin E, Glycosides, Flavonoids, Saponins, Lignin, Polysaccharides
2945	S	C-H str. (Alkene)	beta-Sitosterol, Limonene, Lignin, Aliphatic chains present in the lignocellulose, Vitamin E
2945	S	C-H str. (Aldehyde/ketones)
2832	S	CH₂ str. (Symmetrical)	Aliphatic compounds, beta-Sitosterol, Saponins, Fatty acids, Vitamin E
1658	S	C=O str (Carboxylic group)		Fatty amides (Hexadecanamide, 9-Octadecenamide, (Z) etc.), Pectin, Lignin, Flavonoids, Sitosterol, Limonene, Proteins, Fatty acids
		C=C str (Aromatic)
		C=C str (Alkenes)
1449	M	C-H (Asymmetrical bending)	Limonene, Flavonoids
1310	W	CH₂ bend (Alkane, Symmetrical)	Flavonoids, Steroidal glycosides, Saponins, hexose sugars
1111	S	C-O-C str	Pectin, Glycosides, Polysaccharides, Lignin, Cellulose, Flavonoids, Tocopherol
1019	S	C-O str.	Glycogens

Organisms	Concentration CFU$/mL	Zone of Inhibition (mm)
Organisms	Concentration CFU$/mL	Test 1	Test 2	Test 3	Ciprofloxacin (5 µg/Disc)
Staphylococcus aureus ATCC 25923	2 × 10^-5	12.33 ± 1.15	11 ± 1	10.6 ± 0.47	33.6 ± 1.25
Staphylococcus epidermidis ATCC 12228	3 × 10^-5	10.3 ± 0.55	10.6 ± 0.57	11 ± 1.4	33.3 ± 1
Enterococcus faecalis ATCC 29212	2 × 10^-4	10.6 ± 0.8	10.3 ± 0.6	11.3 ± 1.2	25.3 ± 0.5
Escherichia coli ATCC 25922	4 × 10^-6	12.3 ± 2.08	10.6 ± 0.57	12.3 ± 1.6	35.6 ± 0.94
Klebsiella pneumoniae ATCC 700603	2 × 10^-3	12.6 ± 1.15	10.6 ± 0.7	10.3 ± 0.5	26 ± 1.14
Salmonella choleraesuis ATCC 10708	2 × 10^-5	10.3 ± 0.57	10.3 ± 0.57	12.3 ± 0.47	33.23 ± 1.24
Pseudomonas aeruginosa ATCC 27853	2 × 10^-5	13.3 ± 0.5	10.7 ± 2.5	11.6 ± 0.5	33 ± 0.81
Proteus mirabilis ATCC 299	3 × 10^-5	12.3 ± 1.5	12.6 ± 0.57	12.6 ± 0.48	23.6 ± 1.25

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