Chemical constituents of <i>Pseudobrickellia brasiliensis</i> leaves(Spreng.) R.M. King &amp; H. Rob. (Asteraceae)

DE AMORIM, M.L.L.; GODINHO, W.M.; ARCHANJO, F.C.; GRAEL, C.F.F.

doi:10.1590/1983-084X/15_185

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Artigos • Rev. bras. plantas med. 18 (2) • Apr-Jun 2016 • https://doi.org/10.1590/1983-084X/15_185 copy

Chemical constituents of Pseudobrickellia brasiliensis leaves(Spreng.) R.M. King & H. Rob. (Asteraceae)

Constituintes químicos das folhas de Pseudobrickellia brasiliensis (Spreng.) R.M. King & H. Rob. (Asteraceae).

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

Pseudobrickelliabrasiliensisis aspecies endemic toBrazil, popularlyknown as “arnica”/ “arnica-do-campo”/ “arnica-do-mato” and used for itsanalgesicand anti-inflammatoryproperties. The objective of this research was thephytochemical studyof the essential oilandhexaneandethyl acetateextracts of the leaves of this species. The essential oilwasextracted byhydrodistillation using a Clevengerapparatusand was analyzed byGC/MS, 25components were identified, with a predominance ofmonoterpenes. The extractswere subjected toclassicalchromatographyand the fractionswere analyzed byGC/MS, 1D ¹H-NMR, ¹³C-NMR and ¹³C-NMR-DEPT 135.α-amyrin, α-amyrin acetate, β-amyrin, β-amyrin acetate, lupeol, lupeolacetate, pseudotaraxasterol andtaraxasterol (triterpenes), andkaurenoicacid (diterpene) were identified.Theseterpenesarechemo-taxonomicallyrelated to theEupatorieaetribe(Asteraceae) and may be responsible for the anti-inflammatory activity attributed to the plant.

Key words
Pseudobrickellia brasiliensis; Asteraceae; medicinal plant; phytochemistry; terpenes

Constituents^* * In order of elution	Relative area (%)	RRI cal	RRI lit
1. α-Thujene	17.21	924	931
2. α-Pinene	32.61	932	939
3. N.I.	0.18	939	-
4. N.I.	0.22	948	-
5. Sabinene	4.44	971	976
6. β-Pinene	7.55	977	980
7. β-Myrcene	3.22	987	991
8. α-Phellandrene	8.86	1007	1005
9. α-Terpinene	0.08	1016	1018
10. p-Cymene	0.52	1023	1026
11. Limonene	3.41	1028	1031
12. N.I.	0.05	1030	-
13. Z-β-Ocimene	0.10	1033	1040
14. E-β-Ocimene	4.15	1044	1050
15. γ-Terpinene	0.33	1056	1062
16. α-Terpinolene	0.16	1084	1088
17. N.I.	0.17	1112	-
18. α-Terpineol	0.31	1179	1189
19. δ-Elemene	0.13	1332	1339
20. α-Copaene	1.28	1372	1376
21. E-Caryophyllene	6.87	1415	1418
22. N.I.	0.23	1426	-
23. α-Humulene	0.15	1450	1454
24. Germacrene D	3.40	1476	1480
25. Bicyclogermacrene	1.54	1490	1494
26. α-Muurolene	0.19	1494	1499
27. δ-Cadinene	0.85	1514	1524
28. Germacrene B	1.12	1552	1556
29. Spathulenol	0.46	1571	1576
30. Caryophyllene oxide	0.21	1576	1581

Terpene	Spectrum	Relevant signals of the experimentally obtained spectra^a a Mass spectra fragments: m/z; NMR spectra: δH and δC in ppm and s = singlet.	Literature
Kaurenoic acid (1)	¹H-NMR	2.64 (1H) allylic hydrogen attached to carbon C-13, characteristic of kaurene skeleton diterpenes. This structural type was confirmed by the characteristic signals related to hydrogens H-18 (1.24; s; 3H), H-20 (0.95; s; 3H), H-17 (4.80; s; 1H), and H-17 (4.74; s; 1H).	Vilegas et al., 1997VILEGAS, J.H.Y. et al. Extraction of low-polarity compounds (with emphasis on coumarin and kaurenoic acid) from Mikania glomerata (‘guaco’) leaves. Phytochemical Analysis, v.8, n.5, p.266-70, 1997.; Neto et al., 2008NETO, J.S.L. et al. Constituintes químicos dos frutos de Copaifera langsdorffii Desf. Química Nova, v.31, n.5, p.1078-80, 2008..
	¹³C-NMR	183.6 = carboxyl group (C-19); 155.3 (C-16) and 102.4 (C-17), related to the exocyclic double bond of the kaurene skeleton; and 56.4 (C-5) = trans-axial location between the carboxyl group and the H-5.
	DEPT 135	Signals corresponding to 2 methyl carbons (C-18 and C-20), 10 methylene carbons, 3 methine carbons (C-5, C-9, C-13) and 5 non-hydrogenated carbons. 302 (M⁺), 287 (M⁺ - CH₃), [Remark 3] 259, 241 (M⁺ - CH₃ and - HCOO),
	MS	148, 121 (C₉H₁₃⁺), 109, 105 (C₈H₉⁺), 91 (tropylium ion) [100%]
α-Amyrin (2) and β-Amyrin (4) ^b b Isomers : ursene (2) and oleanene (4) skeletons.	MS	426 (M⁺), 218 (fragment from Diels–Alder retro rearrangement: A and B + rings part of C or D and E rings + part of C) [100%], 203 (218-CH₃ fragment).	Silva et al., 1998SILVA, J.R.A. et al. Ésteres triterpênicos de Himatanthus sucuuba (Spruce. Woodson. Química Nova, v.21, n.6, p.702-4, 1998.; Jeong & Lachance, 2001JEONG, W.S.; LACHANCE, P.A. Phytosterols and fatty acids in fig (Ficus carica, var. mission) fruit and tree components. Food and Chemical Toxicology, v.66, p.278-81, 2001..
α- Amyrin acetate (3) and β-Amyrin acetate (5) ^c c Isomers: ursene (3) and oleanene (5) acetylated.	MS	- 468 (M+), 218 (fragment from Diels-Alder retro rearrangement) [100%], 203 (218-CH₃ fragment)
Lupeol (6),	MS	426 (M+), 203 (D and E rings + part of C), 189(characteristic of lupane skeleton).
Lupeol acetate (7)		468 (M+), 189
Pseudotaraxasterol (8) and Taraxasterol (9) ^d d Positional isomers: urs-20-ene (8) and urs-20 (30)-ene (9)	MS	426 (M+), 189 [100%]

Fraction	Terpene	Area (%)	RRI cal	RRI stan
EHE1	Kaurenoic acid	77.09	0.7891	-
	β-Amyrin acetate	3.34	2.2977	2.305
	α-Amyrin acetate	2.19	2.4736	2.471
	Lupeol acetate	4.86	2.5022	2.505
EHE4	β-Amyrin	8.20	2.1818	2.184
	α-Amyrin	8.03	2.3706	2.370
	Lupeol	29.73	2.3889	2.390
EHE5	Kaurenoic acid	3.18	0.7914	-
	β-Amyrin	16.31	1.3368	1.334
	Lupeol	47.48	1.3854	1.383
	Pseudotaraxasterol	0.50	1.4835	1.480
	Taraxasterol	0.83	1.4977	1.494
AE1	Kaurenoic acid	25.01	0.7970	-
	β-Amyrin	0.25	1.3324	1.334
	Lupeol	0.96	1.3801	1.383

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[1] * cris.grael@ufvjm.edu.br