Chemical Composition and Antioxidant Activity of Essential Oils from Populations of Baccharis dracunculifolia DC. in Southern Brazil

Tomazzoli, Maíra Maciel; Amaral, Wanderlei do; Cipriano, Roger Raupp; Tomasi, Jéssica de Cássia; Gomes, Erik Nunes; Ferriani, Aurea Portes; Maia, Beatriz H. L. de Noronha Sales; Deschamps, Cicero

doi:10.1590/1678-4324-2021190253

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Article - Biological and Applied Sciences • Braz. arch. biol. technol. 64 • 2021 • https://doi.org/10.1590/1678-4324-2021190253 copy

Chemical Composition and Antioxidant Activity of Essential Oils from Populations of Baccharis dracunculifolia DC. in Southern Brazil

Authorship SCIMAGO INSTITUTIONS RANKINGS

HIGHLIGHTS

Essential oils from populations of B. dracunculifolia were investigated.
β-pinene and (E)-nerolidol were the main compounds in B. dracunculifolia populations.
The difference in the chemical profile of the essential oils is quantitative only.
There is a negative correlation between the antioxidant activity and spathulenol.

Abstract

Baccharis dracunculifolia DC. is a Brazilian native plant, presenting wide chemical diversity and numerous pharmaceutical and industrial applications. This research assessed the yield, antioxidant activity and the chemical similarity of essential oils from 10 populations of B. dracunculifolia in the state of Paraná, southern Brazil. The extraction of the volatile compounds was carried out by hydrodistillation, the chemical composition was determined by GC/FID and GC/MS and the antioxidant activity by the DPPH method. The essential oil yield of wild B. dracunculifolia populations ranged from 0.14 to 0.87%. The oils were predominantly composed of oxygenated sesquiterpenes (34.16 - 51.01%), monoterpene hydrocarbons (18.02 - 46.17%) and sesquiterpenes hydrocarbons (9.60 - 17.70%). The major compounds found in all populations were β-pinene (7.65 - 29.8%) and (E)-nerolidol (9.11 - 21.68%). Essential oil solutions (20%) from different populations presented antioxidant capacity ranging from 27.78 to 91.67%. A negative correlation was found between the antioxidant activity and spathulenol (r = -0.696). Multivariate analyses separated the populations into three groups: (1) low concentrations of α-pinene (2.02 - 2.06%), (2) high concentrations of α-pinene (4.17 - 4.61%) and β-pinene (22.54 - 29.80%), and (3) intermediate concentrations of α-pinene (2.38 - 3.31%), β-pinene (12.77 - 19.03%) and spathulenol (6.02 - 9.06%).

Keywords:
β-pinene; (E)-nerolidol; Alecrim-do-campo; DPPH; Medicinal Plant; Asteraceae; Chemotype; Secondary metabolites; Aromatic plants

Populations	Voucher code	Latitude (S)	Longitude (W)	Altitude (m)	Precipitation (mm)	Radiation (W/m²)	Average temperature (°C)
P1	MBM-308.071	25°28’40’’	49°42’22’’	1055	12.8	1143	19.85
P2	MBM-326.212	25°28’13’’	49°43’42’’	1037	12.8	1143	19.85
P3	MBM-336.907	25°39’77’’	49°08’80’’	835	91.0	1065	20.24
P4	MBM-336.908	25°43’95’’	49°05’75’’	999	91.0	1065	20.24
P5	MBM-341.117	25°45’04’	49°01’91’’	886	91.0	1065	20.24
P6	MBM-343.530	25°32’19’’	49°04’35’’	908	92.2	1064	20.1
P7	MBM-348.144	25°30’64’’	49°02’06’’	916	92.2	1064	20.1
P8	MBM-350.603	25°30’30’	49°00’54’’	940	92.2	1064	20.1
P9	MBM-332.462	25°28’18’’	49°38’42’’	1194	92.0	1197	20.81
P10	MBM-334.697	25°19’80’’	49°48’35’’	1027	92.0	1197	20.81

Compounds	IR^lit	IR^cal	P1	P2	P3	P4	P5	P6	P7	P8	P9	P10
1- α-tujene	924	925	-	0.22 ± 0.04	-	0.71 ± 0.00	-	0.21 ± 0.01	0.22 ± 0.03	-	-	-
2- α-pinene	932	932	2.06 ± 0.03	4.61 ± 0.07	3.06 ± 0.01	3.16 ± 1.67	2.02 ± 0.26	2.38 ± 0.12	2.76 ± 0.45	4.17 ± 0.16	3.12± 0.04	3.31 ± 0.10
3- sabinene	969	972	-	-	-	0.72 ± 0.00	0.18 ± 0.05	-	-	0.37 ± 0.00	-	0.21 ± 0.00
4- β-pinene	974	976	17.85 ± 0.41	29.8 ± 4.20	16.34 ± 3.00	15.14 ± 3.86	7.65 ± 1.52	19.03 ± 0.38	19.03 ± 1.14	22.54 ± 1.15	16.40 ± 0.86	12.77 ± 0.99
5- myrcene	988	990	0.89 ± 0.39	1.93 ± 0.21	2.21 ± 0.02	1.14 ± 0.84	0.87 ± 0.17	1.81 ± 0.01	2.13 ± 0.04	1.86 ± 0.12	1.29 ± 0.46	1.62 ± 0.27
6- limonene	1024	1026	2.60 ± 0.07	8.46 ± 1.19	11.66 ± 0.19	9.61 ± 4.96	6.9 ± 1.87	11.24 ± 1.10	12.04 ± 0.04	15.13 ± 1.14	5.51 ± 0.01	12.58 ± 2.83
7- (E)-β-ocimene	1044	1045	1.17 ± 0.47	1.69 ± 0.21	1.03 ± 0.14	0.69 ± 0.46	0.40 ± 0.06	0.89 ± 0.04	1.53 ± 0.03	1.14 ± 0.06	0.75 ± 0.21	0.9 ± 0.13
8- terpinen-4-ol	1174	1174	0.27 ± 0.01	0.30 ± 0.03	0.38 ± 0.01	0.32 ± 0.14	0.14 ± 0.01	0.30 ± 0.00	0.22 ± 0.04	0.26 ± 0.03	0.26 ± 0.04	0.27 ± 0.04
9- α-terpineol	1186	1188	0.49 ± 0.14	0.47 ± 0.06	0.45 ± 0.02	0.44 ± 0.05	0.24 ± 0.04	0.47 ± 0.08	0.28 ± 0.08	0.67 ± 0.05	0.45 ± 0.04	0.63 ± 0.09
10- δ-elemene	1335	1333	0.17 ± 0.04	0.13 ± 0.00	-	0.16 ± 0.00	0.15 ± 0.03	0.23 ± 0.00	0.70 ± 0.09	-	0.12 ± 0.00	-
11- β-elemene	1389	1388	0.37 ± 0.07	0.25 ± 0.04	0.26 ± 0.02	0.33 ± 0.07	0.36 ± 0.05	0.30 ± 0.12	-	-	0.34 ± 0.03	0.15 ± 0.01
12- (E)-β-caryophyllene	1417	1413	2.75 ± 0.51	0.99 ± 0.11	1.57 ± 0.11	1.77 ± 0.55	2.10 ± 0.33	1.24 ± 0.09	2.89 ± 0.2	1.31 ± 0.14	2.30 ± 0.23	2.06 ± 0.03
13- aromadendrene	1439	1432	0.36 ± 0.08	0.19 ± 0.02	0.27 ± 0.03	0.29 ± 0.01	0.35 ± 0.01	0.29 ± 0.00	0.29 ± 0.12	0.28 ± 0.03	0.45 ± 0.04	0.47 ± 0.02
14- cabreuva oxide B	1462	1456	0.57 ± 0.09	0.32 ± 0.02	0.56 ± 0.11	0.64 ± 0.02	0.84 ± 0.13	0.60 ± 0.16	0.38 ± 0.17	0.54 ± 0.04	0.67 ± 0.05	0.83 ± 0.05
15- dauca-5,8-diene	1471	1468	0.20 ± 0.02	0.12 ± 0.01	-	0.20 ± 0.00	0.15 ± 0.00	0.19 ± 0.07	0.16 ± 0.04	0.14 ± 0.01	0.15 ± 0.01	0.14 ± 0.01
16- germacrene D	1484	1474	3.46 ± 0.64	1.84 ± 0.26	2.29 ± 0.68	2.65 ± 0.66	3.39 ± 0.23	3.02 ± 1.11	2.38 ± 0.97	2.18 ± 0.22	3.5 ± 0.24	1.87 ± 0.07
17- bicyclogermacrene	1500	1490	6.36 ± 1.25	3.82 ± 0.45	3.71 ± 1.07	4.39 ± 1.07	5.59 ± 0.97	4.84 ± 1.71	5.38 ± 0.81	3.75 ± 0.41	3.83 ± 0.46	3.54 ± 0.10
18- α-muurolene	1500	1495	0.42 ± 0.07	0.20 ± 0.06	-	0.33 ± 0.09	0.38 ± 0.03	0.37 ± 0.14	0.28 ± 0.06	0.21 ± 0.02	0.33 ± 0.03	0.21 ± 0.03
19- γ-cadinene	1513	1508	0.57 ± 0.09	0.36 ± 0.08	-	0.42 ± 0.13	0.52 ± 0.01	0.50 ± 0.17	0.51 ± 0.08	0.33 ± 0.02	0.45 ± 0.06	0.32 ± 0.04
20- δ-cadinene	1522	1519	2.47 ± 0.39	1.38 ± 0.19	1.62 ± 0.09	1.88 ± 0.05	2.07 ± 0.13	1.60 ± 0.02	1.43 ± 0.10	1.51 ± 0.10	1.77 ± 0.15	1.37 ± 0.15
21- (E)-nerolidol	1561	1564	14.93 ± 1.78	13.2 ± 1.71	19.35 ± 4.49	18.3 ± 3.64	20.71 ± 1.3	13.38 ± 2.5	13.98 ± 2.47	9.11 ± 0.16	22.6 ± 3.47	21.68 ± 3.35
22- spathulenol	1577	1570	7.02 ± 0.57	6.7 ± 0.63	6.68 ± 1.25	8.23 ± 1.68	8.49 ± 0.13	7.52 ± 1.21	9.6 ± 1.86	7.69 ± 0.51	6.02 ± 0.97	6.91 ± 0.42
23- β-Copaen-4α-ol	1590	1576	4.71 ± 0.72	2.79 ± 0.28	3.46± 0.91	3.88 ± 0.93	4.13 ± 0.11	3.42 ± 0.76	3.78 ± 0.96	3.22 ± 0.08	3.22 ± 0.53	4.22 ± 0.20
24- viridiflorol	1592	1583	1.13 ± 0.27	1.65 ± 0.29	2.70 ± 0.31	1.96 ± 0.10	2.10 ± 0.51	1.84 ± 0.15	2.23 ± 0.18	1.78 ± 0.13	2.24 ± 0.29	1.02 ± 0.03
25- cubeban-11-ol	1595	1586	0.28 ± 0.07	0.14 ± 0.02	-	0.31 ± 0.00	0.25 ± 0.02	0.22 ± 0.08	-	0.16 ± 0.02	0.18 ± 0.04	0.21 ± 0.01
26- ledol	1602	1594	2.18 ± 0.37	1.72 ± 0.17	1.55 ± 0.22	2.19 ± 0.20	2.55 ± 0.1	1.44 ± 0.06	1.59 ± 0.23	2.07 ± 0.08	2.11 ± 0.29	2.01 ± 0.10
27- β-oplopenone	1607	1604	0.28 ± 0.04	0.21 ± 0.03	0.27 ± 0.07	0.31 ± 0.11	0.33 ± 0.03	0.29 ± 0.07	0.26 ± 0.08	0.28 ± 0.02	0.27 ± 0.05	0.25 ± 0.02
28- junenol	1618	1615	0.25 ± 0.07	0.16 ± 0.01	0.27 ± 0.07	0.32 ± 0.00	0.23 ± 0.02	0.19 ± 0.06	0.33 ± 0.00	0.15 ± 0.01	0.20 ± 0.04	0.26 ± 0.01
29- 1-epi-cubenol	1627	1621	0.95 ± 0.14	0.53 ± 0.05	0.27 ± 0.07	0.71 ± 0.02	0.82 ± 0.08	0.46 ± 0.10	0.51 ± 0.12	0.47 ± 0.03	0.76 ± 0.08	0.42 ± 0.03
30- epi-α-muurolol	1640	1635	3.13 ± 0.56	1.91 ± 0.27	1.67 ± 0.05	2.33 ± 0.71	2.87 ± 0.12	1.66 ± 0.07	1.26 ± 0.14	2.00 ± 0.12	2.17 ± 0.22	1.89 ± 0.23
31- α-muurolol	1644	1640	0.94 ± 0.17	0.59 ± 0.09	0.66 ± 0.20	2.33 ± 0.71	1.11 ± 0.17	0.59 ± 0.16	0.54 ± 0.17	0.62 ± 0.04	0.75 ± 0.11	0.56 ± 0.05
32- α-cadinol	1652	1647	3.85 ± 0.03	2.56 ± 0.59	2.79 ± 0.03	2.95 ± 0.38	3.93± 0.16	3.00 ± 0.09	2.07 ± 0.53	2.75 ± 0.19	2.66 ± 0.36	2.21 ± 0.26
germacra--trien-1α-ol	1685	1678	1.87 ± 0.38	1.37 ± 0.31	1.14 ± 0.18	1.91 ± 0.1	2.51 ± 0.35	1.32 ± 0.10	1.10 ± 0.30	1.99 ± 0.15	2.25 ± 0.46	1.32 ± 0.17
34- isobicyclogermacrenal	1733	1724	0.34 ± 0.07	0.37 ± 0.07	0.41 ± 0.12	0.48 ± 0.19	0.60 ± 0.05	0.43 ± 0.13	0.26 ± 0.01	0.50 ± 0.04	0.42 ± 0.10	0.36 ± 0.03
35- khusimol	1741	1733	0.27 ± 0.06	0.26 ± 0.07	0.28 ± 0.10	0.33 ± 0.16	0.38 ± 0.00	0.29 ± 0.10	0.32 ± 0.14	0.37 ± 0.04	0.26 ± 0.08	0.25 ± 0.04
Monoterpene hydrocarbons			24.57	46.71	34.30	31.17	18.02	35.56	37.85	45.21	27.07	31.39
Oxygenated monoterpenes			0.76	0.77	0.83	0.76	0.38	0.77	0.50	0.93	0.71	0.90
Sesquiterpene hydrocarbons			17.70	9.60	10.28	13.06	15.90	13.18	14.40	10.25	13.91	10.96
Oxygenated sesquiterpenes			42.13	34.16	41.50	46.54	51.01	36.05	37.83	33.16	46.11	43.57
Identified compounds %			84.45	91.24	86.91	91.53	85.31	85.56	90.58	89.55	87.80	86.82

Composition	Main component
Composition	PC1	PC2	PC3
α-pinene	0.4332	-0.0669	0.1265
β-pinene	0.3310	0.1603	0.5306
Limonene	0.3220	0.2527	-0.4388
Germacrene D	-0.3942	-0.1144	0.2433
bicyclogermacrene	-0.374	0.3921	0.1880
(E)-nerolidol	-0.1869	-0.5681	-0.3871
spathulenol	-0.0862	0.6298	-0.3202
β-opaen-4-α-ol	-0.3564	0.1385	-0.2562
α-cadinol	-0.3657	0.0180	0.3116
Variance (eigenvalue)	4.555	1.727	1.467
Cumulative variance (%)	50.61	69.80	86.10

Composition	DPPH	p-value	Altitute	p-value	Rad	p-value	Temp(°C)	p-value	Prec	p-value
β-pinene	-0.24	0.68	0.04	0.64	0.04	0.62	-0.53	0.93	-0.54	0.1
α-pinene	0.01	0.73	0.17	0.77	0.17	0.62	-0.03	0.11	-0.15	0.66
limonene	0.03	0.92	-0.40	0.11	-0.40	0.24	0.10	0.77	0.57	0.08
spathulenol	-0.69*	0.03	0.53	0.11	-0.67*	0.03	-0.31	0.37	0.31	0.38
β-opaen-4-α-ol	-0.01	0.86	0.05	0.88	0.05	0.87	0.037	0.91	-0.05	0.87
bicyclogermacrene	-0.50	0.12	-0.14	0.69	0.26	0.46	-0.49	0.14	-0.30	0.38
α-cadinol	0.09	0.78	0.12	0.77	0.20	0.56	-0.35	0.31	-0.29	0.41
germacrene D	-0.11	0.71	0.25	0.48	0.01	0.95	0.047	0.89	0.01	0.99
(E)-nerolidol	0.47	0.267	0.27	0.43	0.45	0.19	0.76*	0.01	0.30	0.38

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[1] *Correspondence: mairatomazzoli@gmail.com(M.M.T.).