Headspace GC/MS for identification of bioactive compounds of <i>Curcuma longa</i> L<i>.</i> leaf extract: Industrial application as antioxidant for soybean oil

Alves, Izabel de Paula Duarte; Jesus Maria, Zamira Abel de; Pereira, Julião; Martins, Gardênia; Oliveira, Tatianne Ferreira de

doi:10.1590/1413-7054202347013922

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Food Science and Technology • Ciênc. agrotec. 47 • 2023 • https://doi.org/10.1590/1413-7054202347013922 copy

Headspace GC/MS for identification of bioactive compounds of Curcuma longa L. leaf extract: Industrial application as antioxidant for soybean oil

Headspace GC/MS para identificação de compostos bioativos do extrato da folha de Curcuma longa L.: Aplicação industrial como antioxidante para óleo de soja

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

The use of natural antioxidants extracted from plants is an alternative to the application of synthetic antioxidants. In this study, we evaluated the oxidative stability of soybean oil after the addition of Curcuma longa L. leaf extracts compared to its oxidative stability with the synthetic antioxidant butylated hydroxytoluene (BHT Different concentrations (0.5%, 1.0%, and 1.5%) of ethanolic extract of Curcuma longa L. leaves were added to the oil, and the mixture was heated at 60 ±2 °C for 12 days. Several parameters of oxidative stability, including the peroxide index (PI), thiobarbituric acid reactive substances (TBARS), and conjugated dienes and trienes, were analyzed every three days. The results were promising, the oils to which the Curcuma longa L. leaf extract was added showed a reduction in all parameters, indicating oxidative deterioration under the influence of the concentration of the extract and the duration of treatment. The extract was less effective at low concentrations (0.5%), the parameters did not vary considerably. The PI was low in all treatments until the third day. The PI of the soybean oil treated with 1.5% extract was lower than that after treatment with the synthetic antioxidant and the blank treatment on days 6 to 12. The highest production of TBARS was observed in the blank treatment on days 6 to 12, and the lowest values of TBARS were recorded in the soybean oil treated with 1.5% extract. For the same concentration, the conjugated dienes varied from 2.05 to 8.6, and the trienes from 0.57 to 1.59.

Index terms:
Natural antioxidants; oxidative stability; peroxide index; plants

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[1] ^*Corresponding author: maria2345678@discente.ufg.br

No.	Name	Molecular Formula	Retention Time (RT)	Relative content (%)	MS Similarity (%)
1	Methyl Alcohol	CH4O	3.027	5.33	97
2	Butanal, 3-methyl-	C5H10O	3.192	0.47	86
3	2,3-Butanedione	C4H6O2	4.017	0.26	86
4	Tricyclo [2.2.1.0(2,6)]heptane, 1,3,3-trimethyl-	C10H16	4.336	0.42	94
5	(1R)-2,6,6-Trimethylbicyclo [3.1.1]hept-2-ene	C10H16	4.587	2.99	96
6	Bicyclo [3.1.0]hex-2-ene, 4-methyl-1-(1-methylethyl)-	C10H16	4.689	0.27	80
7	Camphene	C10H16	5.353	5.32	95
8	Bicyclo [3.1.1]heptane, 6,6-dimethyl- 2-methylene-, (1S)-	C10H16	6.048	3.29	95
9	Bicyclo [3.1.0]hexane, 4-methylene-1-(1-methylethyl)-	C10H16	6.324	0.25	96
10	β.-Myrcene	C10H16	7.276	0.33	96
11	D-Limonene	C10H16	8.079	2.11	94
12	Eucalyptol	C10H18O	8.514	42.82	95
13	o-Cymene	C10H14	10.107	0.26	96
14	Acetic acid	C2H4O2	15.286	0.20	78
15	Cyclohexene, 4-ethenyl-4-methyl-3-(1-methylethenyl)-1-(1-methylethyl)-, (3R-trans)-	C15H24	15.371	0.19	90
16	trans-Linalool oxide (furanoid)	C10H18O2	15.496	0.27	91
17	(-)-.beta.-Bourbonene	C15H24	16.480	1.66	90
18	(+)-2-Bornanone	C10H16O	16.552	14.09	96
19	Linalool	C10H18O	17.430	1.04	97
20	(S,1Z,6Z)-8-Isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene	C15H24	17.848	0.32	89
21	Cyclohexane, 1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, [1S-(1.alpha.,2.beta.,4.beta.)]-	C15H24	18.308	3.13	96
22	Caryophyllene	C15H24	18.418	1.60	95
23	Bicyclo [2.2.1]heptan-2-ol, 2,3,3-trimethyl-	C10H18O	18.583	0.28	92
24	3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-, (R)-	C10H18O	18.724	0.57	95
25	Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, [1R-(1.alpha.,7.beta.,8a.alpha.)]-	C15H24	19.045	0.27	91
26	(S,1Z,6Z)-8-Isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene	C15H24	19.500	0.27	93
27	Bicyclo [3.1.1]heptan-3-ol, 6,6-dimethyl-2-methylene-, [1S-(1.alpha.,3.alpha.,5.alpha.)]-	C10H16O	19.961	0.16	95
28	Isoborneol	C10H18O	20.254	2.76	97
29	Cyclohexanemethanol, .alpha.,.alpha.-dimethyl-4-methylene-	C10H18O	20.374	0.36	92
30	L-.alpha.-Terpineol	C10H18O	20.960	1.71	93
31	Bicyclo [2.2.1]heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)-	C10H18O	21.024	1.53	87
32	Naphthalene, decahydro-4a-methyl-1-methylene-7-(1-methylethenyl)-, [4aR-(4a.alpha.,7.alpha.,8a.beta.)]-	C15H24	21.306	0.54	97
33	Naphthalene, 1,2,3,4,4a,5,6,8a-octahydro-4a,8-dimethyl-2-(1-methylethenyl)-, [2R-(2.alpha.,4a.alpha.,8a.beta.)]-	C15H24	21.430	0.38	93
34	(-)-Carvone	C10H140	21.796	0.23	92
35	Benzofuran, 6-ethenyl-4,5,6,7-tetrahydro-3,6-dimethyl-5-isopropenyl-, trans-	C15H20O	24.730	0.39	95
36	Caryophyllene oxide	C15H24O	26.829	0.65	91
37	Isospathulenol	C15H24O	27.087	0.19	81
38	Epicurzerenone	C15H18O2	30.002	0.52	94
39	Curcumenol	C15H2202	31.510	0.24	82
40	Cyclodeca [b]furan-2(3H)-one, 3a,4,5,8,9,11a-hexahydro-3,6,10-trimethyl-, [3S-(3R,3aR,6E,10E,11aR*)]-	C15H2202	31.828	0.54	73
41	Cyclohexene, 4-pentyl-1-(4-propylcyclohexyl)-	C20H36	32.070	0.68	72
42	Curcumenol	C15H2202	33.744	1.09	94

Solvent	TPC mg GAE (100 g^-1 dry matter)	DPPH (mg TE 100 g^-1)	FRAP (µMol FeSO₄ 100 g^-1)
E/W	2422.04	1847.08	217.99

Peroxide index
Concentration (%)	Time (days)
Concentration (%)	0	3	6	9	12
0.5%	1.7219^a	3.4811^b	13.1892^c	19.1918 ^d	70.1865 ^e
1.0%	1.9912 ^a	3.4575 ^b	4.4519 ^c	11.1386 ^d	65.1163 ^e
1.5%	1.8242 ^a	4.6945 ^b	3.4666 ^c	9.3543 ^d	31.4712 ^e
Blank	1.7349 ^a	3.7299 ^b	29.1885 ^c	45.2020 ^d	103.2724 ^e
Control (BHT)	1.2273 ^a	1.7219 ^b	16.2080 ^c	28.8447 ^d	85.7655 ^e

TBARS
Concentration (%)	Time (days)
Concentration (%)	0	3	6	9	12
0.5%	0.1677^a	0.3237^b	0.2574^c	0.4485^d	1.1973ª
1.0%	0.1521^a	0.2652 ^b	0.2691 ^c	0.351 ^d	1.092^e
1.5%	0.1014 ^a	0.1053 ^b	0.1911 ^b	0.2418^c	0.7176^d
Blank	0.234 ^a	0.3198 ^b	0.6708 ^c	0.6669^d	1.4469^e
Control (BHT)	0.2028 ^a	0.3393 ^b	0.3939 ^b	0.4875^c	1.0335^d

Conjugated Dienes
Concentration (%)	Time (days)
Concentration (%)	0	3	6	9	12
0.5%	4.3944^a	1.9865^b	1.2596 ^b	6.9102^c	10.8607^d
1.0%	3.8094 ^a	0.7234 ^b	0.5665^c	3.0093^d	12.0694^e
1.5%	2.0584 ^a	0.9325 ^b	0.2946^a	0.9077^c	8.6473^d
Blank	5.6591 ^a	5.4182^a	11.4173 ^b	1.9073^c	15.6597^d
Control (BHT)	5.5523 ^a	5.0960^a	6.3554 ^b	11.3211^c	12.9167^d
Conjugated Trienes
Concentration (%)	Time (days)
Concentration (%)	0	3	6	9	12
0.5%	1.5581^a	0.6914^b	0.6677^b	1.5986^c	1.6291^c
1.0%	1.2376^a	0.5623^b	0.5665^b	1.0426^a	1.7694^c
1.5%	0.5756^a	0.3153^b	0.0902^c	0.6552^a	1.5925^d
Blank	1.8591^a	1.7500^a	1.9252^a	1.9073^a	1.6528^a
Control (BHT)	1.9186^a	1.7483^a	1.7727^a	1.8862^a	0.7541^b