Chemical Characterization and Antiradical Properties of Pyroligneous Acid from a Preserved Bamboo, Guadua angustifolia Kunth

Gomez, Juliana Peña; Velez, Juan Pablo Arrubla; Pinzon, María Alejandra; Arango, Jorge Augusto Montoya; Muriel, Andrés Prieto

doi:10.1590/1678-4324-2021190730

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Article - Biological and Applied Sciences • Braz. arch. biol. technol. 64 • 2021 • https://doi.org/10.1590/1678-4324-2021190730 copy

Chemical Characterization and Antiradical Properties of Pyroligneous Acid from a Preserved Bamboo, Guadua angustifolia Kunth

Authorship SCIMAGO INSTITUTIONS RANKINGS

HIGHLIGHTS

Chemical characterization of PA extracts has high content of phenolic compounds.

PA extracts from G. angustifolia may be used in the pharmaceutical industry and agriculture.

A total of 66 compounds with approximate match percentage ≥ 89% were identified.

The PA extracts showed a high content of antioxidant properties.

Abstract

Pyroligneous acid (PA) was obtained by condensation of the vapors produced in the thermal decomposition of culms residues from Guadua angustifolia Kunth (G. angustifolia) cultivated in Colombia, with and without previous preservation treatment with borax salts. Chemical characterization by GC-MS showed that PA extracts has high content of phenolic compounds. Mequinol, isocreosol, 4-ethylphenol, 4-ethyl-2-methoxyphenol, 3,5-dimethoxy-4-hydroxytoluene and 2,6-dimethoxyphenol were the most abundant substances, identified. The total phenolic content (TPC) and DPPH free radical scavenging activity, were investigated. TPC showed a concentration of 1.959 mg GA g^-1±0.010 and 3.844 mg GA g^-1±0.027 to PAC and PAS samples. These samples also exhibited high DPPH activity of 70.975%±0.921 and, 16.667%±0.298, respectively. The chemical composition, TPC and DPPH results indicate that the PA extracts obtained from G. angustifolia may be used as a raw material in the food industry as natural preservative, in medicine as alternative to antibiotics and in agriculture as insect repellent and foliar fertilizer.

Keywords:
Guadua angustifolia Kunth; pyroligneous acid; gas chromatography - mass spectrometry; antioxidant activity; wood vinegar

GRAPHICAL ABSTRACT

					PAC		PAS
N°	Retention Time (min)	Compound	Molecular Formula	Molar Mass (g mol^-1)	Similarity (%)	Area (%)	Similarity (%)	Area (%)
		Furan and pyran derivatives				5.99		3.3
1	2.57	2,5-Dimethyltetrahydrofuran	C₆ H₁₂O	100.16	94	0.12	--	nq
2	2.98	2-Methoxytetrahydrofuran	C₅ H₁₀O₂	101.13	96	0.85	97	0.47
3	4.61	2-Furanmethanol	C₅ H₆O₂	98.09	--	nq	94	0.19
4	5.96	1-(2-Furanyl)- ethanone	C₆ H₆O₂	110.11	94	1.71	90	0.91
5	7.72	Methyl 2-furoate	C₆ H₆O₃	126.11	89	0.38	92	0.34
6	8.60	Tetrahydro-2-furanmethanol	C₅H₁₀O₂	102.13	89	0.19	93	0.57
7	8.70	1-(2-Furanyl)-1-propanone	C₇H₈O₂	124.13	95	0.29	94	0.16
		Organic acid				2.45		0.66
8	2.83	2-Methylpropanoic acid	C₄H₈O₂	88.11	95	0.43	94	0.08
9	3.25	Butanoic acid	C₄H₈O₂	88.11	98	1.38	96	0.45
10	3.83	Crotonic acid	C₄H₆O₂	86.09	94	0.10	93	0.07
11	4.39	2-Methylbutanoic acid	C₅H₁₀O₂	102.13	95	0.16	---	nq
12	5.12	Pentanoic acid	C₅H₁₀O₂	102.13	97	0.28	---	nq
13	6.84	4-Methylpentanoic acid	C₆H₁₂O₂	117.15	93	0.10	91	0.06
		Ketones				8.45		5.41
14	3.39	2,4-Dimethyl-3-pentanone	C₇H₁₄O	114.19	89	0.09	---	nq
15	3.52	Cyclopentanone	C₅H₈O	84.11	96	0.30	97	0.15
16	4.44	2-Methycyclopentanone	C₆H₁₀O	98.14	94	0.11	95	0.07
17	5.65	Cyclohexanone	C₆H₁₀O	98.14	90	0.09	--	nq
18	5.85	2-Methyl-2-cyclopenten-1-one	C₆H₈O	96.13	94	1.01	95	0.63
19	6.36	2,5-Hexanedione	C₆H₁₀O₂	114.14	94	0.25	90	0.08
20	7.30	3,3-Dimethyl-2-butanone	C₆H₁₂O	100.16	--	nq	90	0.15
21	7.39	3-Methyl-2-cyclopenten-1-one	C₆H₈O	96.13	83	1.93	91	1.02
22	8.23	3,4-Dimethyl-2-cyclopenten-1-one	C₇H₁₀O	110.15	94	0.44	89	0.40
23	9.14	3-Methyl-1,2-cyclopentanedione	C₆H₈O₂	112.13	88	1.26	92	1.02
24	9.53	2,3-Dimethyl-2-cyclopenten-1-one	C₇H₁₀O	110.16	95	1.81	92	0.99
25	10.66	Acetophenone	C₈H₈O	120.15	--	nq	97	0.18

26	12.73	3-Ethyl-2-hydroxy-2-cyclopenten-1-one	C₇H₁₀O₂	126.15	89	0.95	92	0.93
27	22.28	1-(2,5-Dihydroxyphenyl) ethanone	C₈H₈O₃	152.14	88	0.13	89	0.32
28	23.72	3-Butyl-2-hydroxy-2-cyclopenten-1-one	C₉H₁₄O₂	154.20	85	0.08	90	0.16
29	31.84	Guaiacylacetone	C₁₀H₁₂O₃	180.20	--	nq	93	0.30
		Alkyl aryl ether				4.54		6.31
30	5.08	o-Xylene	C₈H₁₀	106.16	---	nq	96	1.14
31	20.83	1-Ethyl-4-methoxybenzene	C₉H₁₂O	136.19	--	nq	95	1.38
32	23.92	1,2,3-Trimethoxybenzene	C₉H₁₂0₃	168.19	89	0.18	84	0.44
33	31.77	1,2,3-Trimethoxy-5-methylbenzene	C₁₀H₁₄O₃	182.21	85	4.36	85	3.35
		Aldehydes				0.13		0.00
34	28.16	3-Hidroxy-4-methoxybenzaldehyde	C₈H₈O₃	152.15	91	0.13	--	nq
		Esters				0.98		0.76
35	2.64	Methyl butyrate	C₅H₁₀O₂	102.13	94	0.08	97	0.19
36	4.87	Ethylene glycol diacetate	C₆H₁₀O₄	146.14	96	0.23	--	nq
37	8.04	Methyl levulinate	C₆H₁₀O₃	130.14	94	0.30	86	0.17
38	31.64	Methyl vanillate	C₉H₁₀O₄	182.17	92	0.20	82	0.20
39	34.45	Methyl 3-(4-hidroxy-3-methoxyphenyl) propanoate	C₁₁H₁₄O₄	210.23	91	0.17	82	0.20
		Alcohols				0.23		0.20
40	8.90	4,5-Dimethyl-2-hepten-3-ol	C₉H₁₈O	142.24	92	0.23	92	0.20
		Amides				0.34		0.33
41	41.59	Oleamide	C₁₈H₃₅NO	281.50	93	0.34	94	0.33
		Phenol and derivatives				62.60		55.29
42	7.82	Phenol	C₆H₆O	94.11	97	3.38	98	3.20
43	10.13	o-Cresol	C₇H₈O	108.13	95	2.50	96	2.41
44	10.39	o-Guaiacol	C₇H₈O₂	124.14	87	0.37	87	0.33
45	10.93	p-Cresol	C₇H₈O	108.13	94	3.69	95	3.22
46	11.47	Mequinol	C₇H₈O₂	124.14	98	15.83	97	9.87
47	12.39	2,6-Dimethylphenol	C₈H₁₀O	122.16	82	0.27	96	0.66
48	13.73	2-Methoxy-3-methylphenol	C₈H₁₀O₂	138.16	86	0.03	--	nq
49	13.87	2-Ethylphenol	C₈H₁₀O	122.16	76	0.53	89	0.87
50	14.56	2,4-Dimethylphenol	C₈H₁₀O	122.16	96	0.83	96	1.48
51	15.71	4-Ethylphenol	C₈H₁₀O	122.16	98	7.14	98	6.33
52	15.85	3-Ethylphenol	C₈H₁₀O	122.16	79	0.01	86	0.39
53	17.44	Isocreosol	C₈H₁₀O₂	138.17	97	9.47	96	6.81
54	17.69	3,5-Dimethylphenol	C₈H₁₀O	122.16	92	0.08	92	0.55
55	20.26	p-Cumenol	C₉H₁₂O	136.19	91	0.22	--	nq
56	20.83	2-Ethyl-4-methylphenol	C₉H₁₂O	136.19	93	0.48	90	0.13
57	22.13	2,3,5-Trimethylphenol	C₉H₁₂O	136.19	86	0.12	91	0.22
58	22.41	4-Ethyl-2-methoxyphenol	C₉H₁₂O₂	152.19	93	5.04	94	8.75
59	25.72	2,6-Dimethoxyphenol	C₈H₁₀O₃	154.17	94	7.48	94	5.09
60	26.06	Eugenol	C₁₀H₁₂O₂	164.20	95	0.24	95	0.67
61	26.62	2-Methoxy-4-propylphenol	C₁₀H₁₄O₂	166.22	89	0.12	92	0.81
62	29.85	3,5-Dimethoxy-4-hydroxytoluene	C₉H₁₂O₃	168.18	92	3.94	92	2.25
63	30.02	trans-Isoeugenol	C₁₀H₁₂O₂	164.20	--	nq	92	0.36
64	30.89	1-(4-Hidroxy-3-methoxyphenyl) ethanone	C₉H₁₀O₃	166.17	93	0.13	--	nq
65	32.22	2,6-Dimethoxy-4-(2-propenyl) phenol	C₁₁H₁₄O₃	194.23	94	0.62	93	0.73
66	34.31	(E)-2,6-Dimethoxy-4-(prop-1-en-1-yl) phenol	C₁₁H₁₄O₃	194.22	83	0.08	84	0.16
Total						84.73		72.26

Extracts	Antioxidant activity
	TPC assay		DPPH assay
	Absorbance	Gallic acid equivalents (mg GAE g^-1)	Absorbance	Free radical scavenging activity (%)
PAC	0.429 ± 0.002	1.96 ± 0.01	0.162 ± 0.005	70.98 ± 0.92
PAS	0.525 ± 0.003	3.84 ± 0.03	0.427 ± 0.002	16.67 ± 0.30

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