Chemical composition and antinociceptive activity of volatile fractions of the aerial parts of Solidago chilensis (Compositae)

Valverde, Simone Sacramento; Souza, Stefânia Priscilla de; Oliveira, Temistocles Barroso de; Kelly, Andressa Maia; Costa, Nathalia Ferreira; Calheiros, Andrea Surrage; Lima, Keila dos Santos Cople; Frutuoso, Valber da Silva; Lima, Antônio Luís dos Santos

doi:10.1590/2175-7860202071053

Simone Sacramento Valverde ⁵5 Author for correspondence: simonevalverde@far.fiocruz.br

Military Institute of Engineering, Chemical Engineering Department, General Tibúrcio Square 80, Urca, 22290-270, Rio de Janeiro, RJ, Brazil.

FIOCRUZ - Farmanguinhos, Pharmaceutical Technology Institute, Sizenando Nabuco Street 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil.

https://orcid.org/0000-0001-9043-3739

Stefânia Priscilla de Souza

Military Institute of Engineering, Chemical Engineering Department, General Tibúrcio Square 80, Urca, 22290-270, Rio de Janeiro, RJ, Brazil.

Temistocles Barroso de Oliveira

FIOCRUZ - Farmanguinhos, Pharmaceutical Technology Institute, Sizenando Nabuco Street 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil.

Andressa Maia Kelly

FIOCRUZ - Farmanguinhos, Pharmaceutical Technology Institute, Sizenando Nabuco Street 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil.

Nathalia Ferreira Costa

FIOCRUZ - Oswaldo Cruz Institute, Sizenando Nabuco Street 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil.

Andrea Surrage Calheiros

FIOCRUZ - Oswaldo Cruz Institute, Sizenando Nabuco Street 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil.

Keila dos Santos Cople Lima

Military Institute of Engineering, Chemical Engineering Department, General Tibúrcio Square 80, Urca, 22290-270, Rio de Janeiro, RJ, Brazil.

Valber da Silva Frutuoso

FIOCRUZ - Oswaldo Cruz Institute, Sizenando Nabuco Street 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil.

Antônio Luís dos Santos Lima

Military Institute of Engineering, Chemical Engineering Department, General Tibúrcio Square 80, Urca, 22290-270, Rio de Janeiro, RJ, Brazil.

5 Author for correspondence: simonevalverde@far.fiocruz.br

Area Editor: Dr. Leopoldo Baratto

Conflicts of interest

The authors declare no conflict of interest.

Compound² 2 Compounds are listed in order of their elution from a DB-5 column.	Linear retention index³ 3 RI = retention indices relative to C8 - C28 n-alkanes.	Electron impact mass spectrometric data	Relative content (%)
	sample	Electron impact mass spectrometric data	CSV	DIV	FIV
α-pinene	942	93; 91; 92; 77; 121; 136	4.62	3.23	5.59
camphene	953	93; 121; 79; 107; 136	-	1.28	2.36
β-pinene	983	93; 41; 69; 91,136	1.78	1.79	3.41
β-myrcene	992	93; 41; 69; 91; 136	-	-	2.29
α-phellandrene	1007	93; 91; 77; 92; 136	2.6	1.5	4.42
o-cymene	1025	119; 134; 91; 117	1.38	1.27	-
β-phellandrene	1033	93; 77; 91; 136	-	-	1.26
limonene	1034	68; 67; 93; 79; 121; 136	6.77	7.54	20.95
(Z)-β-ocimene	1040	93; 91; 79; 77; 41; 136	-	1.3	6.08
bornyl acetate	1284	95; 43; 93; 136; 121; 196	12.95	9.03	16.72
α-cubebene	1353	119; 105; 161	1.85	-	-
copaene	1378	161; 91; 105; 119; 133	3.84	3.21	1.92
β-bourbonene	1385	81; 29; 80; 123; 161; 204	11.87	7.58	2.1
isocaryophyllene	1411	69; 161; 93; 41; 93;105; 204	4.18	-	-
β-caryophyllene	1420	93; 133; 91; 41; 79; 69; 204	10.91	10.72	4.94
γ-elemene	1434	93; 81; 67; 41; 107; 147; 161	11.68	8.14	5.97
α-humulene	1443	93; 80; 121; 41; 204	3.58	3.68	1.32
(Z)-β-farnesene	1445	119; 93; 41; 91; 204	-	11.82	1.42
γ-muurolene	1479	161; 93; 105; 119; 204	1.31	-	-
germacrene D	1482	161; 105; 91; 119; 79; 204	19.35	22.43	20.8

Compound² 2 Compounds are listed in order of their elution from a DB-5 column.	Linear retention index³ 3 RI = retention indices relative to C8 - C28 n-alkanes.	Electron impact mass spectrometric data	Relative content ^a(%)
	sample	Electron impact mass spectrometric data	EOCS	EODI	EOFI
α-pinene	940	93; 91; 92; 77; 121; 136	3.89	2.24	3.1
camphene	951	93; 121; 79; 107; 136	-	-	0.98
β-pinene	982	93; 41; 69; 91,136	1.39	0.9	1.2
β-myrcene	994	93; 41; 69; 91; 136	-	-	0.76
α-phellandrene	1005	93; 91; 77; 92; 136	2.67	-	2.07
o-cymene	1023	119; 134; 91; 117	1.69	-	-
limonene	1032	68; 67; 93; 79; 121; 136	4.41	5.745	10.07
(Z)-β-ocimene	1043	93; 91; 79; 77; 41; 136	-	0.6	2.13
bornyl acetate	1284	95; 43; 93; 136; 121; 196	8.19	6.9	7.06
α-cubebene	1352	119; 105; 161	1.2	2.18	-
copaene	1379	161; 91; 105; 119; 133	1.85	2.23	1.27
β-bourbonene	1383	81; 29; 80; 123; 161; 204	7.32	6.39	2.03
Isolongifolene	1388	131; 187; 91; 146; 202	2.24	1.84	1.62
β-cubebene	1389	161; 105; 119; 91; 204	-	0.69	2.69
α-gurjunene	1412	105; 161; 204; 119; 91	1.19	1.16	-
β-caryophyllene	1419	93; 133; 91; 41; 79; 69; 204	6.87	9.03	5.51
γ-elemene	1428	93; 81; 67; 41; 107; 161	8.40	7.54	7.78
aromadendrene	1439	145; 159; 202; 131; 105; 204	2.93	1.86	2.34
α-guaiene	1440	105; 107; 93; 147; 204	3.81	2.3	-
α-humulene	1441	93; 80; 121; 41; 204	2.52	2.69	1.28
(Z)-β-farnesene	1443	119; 93; 41; 91; 204	2.17	9.69	2.64
γ-muurolene	1480	161; 93; 105; 119; 204	-	0.74	-
germacrene D	1483	161; 105; 91; 119; 79; 204	12.11	22.01	23.3
α-bisabolene	1507	93; 119; 41; 105; 204	-	0.83	-
δ-cadinene	1526	161; 134; 105; 119; 204	-	0.91	-
δ-calacorene	1540	157; 142; 141; 200; 183	1.79	-	-
germacrene B	1563	121; 93; 41; 107; 204	-	1.51	-
spathulenol	1573	43; 41; 205; 119; 220	7.93	3.38	3.52
caryophyllene oxide	1583	91; 67; 41; 109; 121; 138	1.88	1.54	0.66
δ- cadinol	1638	161; 43; 119; 105; 41; 204; 222	-	0.7	1.72
cedren-13-ol	1644	119; 41;91;105; 220	1.02	0.65	1.58
α-cadinol	1656	43; 95; 121; 41; 204; 222	-	1.04	2.61
acorenone	1685	220; 41;159;91;191; 105	2	1.56	-
(E)-phytol	1945	71; 57;43; 123; 295	2.33	-	0.81
solidagenone	2385	82; 81; 41; 111; 95; 316	0.9	0.67	1.85

Aerial part	Major compounds	Method of detection/extraction
Central stems	Germacrene D, bornyl acetate, γ-elemene, β-caryophyllene, limonene	SPME
Central stems	Germacrene D, γ-elemene, bornyl acetate, spathulenol, β-caryophyllene	hydrodistillation
Dry inflorescences	Germacrene D, (Z)- β-farnesene, β-caryophyllene, bornyl acetate	SPME
Dry inflorescences	Germacrene D, β-caryophyllene, γ-elemene, bornyl acetate	hydrodistillation
Fresh inflorescences	Limonene, germacreno D, bornyl acetate	SPME
Fresh inflorescences	Germacrene D, limonene, γ-elemene, β-caryophyllene	hydrodistillation

Treatment	Dose (mg/Kg)	Number of writhings² 2 Values represent mean ± S.E.M.;	% Inhibition
Saline	-	45.14 ± 3.3	0%
EOCS	1	29.42 ± 4.6	34.84^ P < 0.01;
EOI	1	23.08 ± 1.4	48.86^ P < 0.01;
EOFI	1	21.25 ± 4.2	52.93^* ***** P < 0.001.
Diclofenac	50	14.83 ± 3.1	67.14

[1] 5 Author for correspondence: simonevalverde@far.fiocruz.br

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Chemical composition and antinociceptive activity of volatile fractions of the aerial parts of Solidago chilensis (Compositae)

Abstract