Distribution of metabolites in galled and non-galled leaves of Clusia lanceolata and its antioxidant activity

Ferreira, Rafaela O.; Carvalho Junior, Almir R. de; Silva, Telma M.G. da; Castro, Rosane N.; Silva, Tania M.S. da; Carvalho, Mário G. de

doi:10.1016/j.bjp.2014.11.005

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Original Articles • Rev. bras. farmacogn. 24 (6) • Nov-Dec 2014 • https://doi.org/10.1016/j.bjp.2014.11.005 copy

Distribution of metabolites in galled and non-galled leaves of Clusia lanceolata and its antioxidant activity

Authorship SCIMAGO INSTITUTIONS RANKINGS

Essential oils of galled and non-galled leaves of Clusia lanceolataCambess., Clusiaceae, were obtained by hydrodistillation and analyzed by GC and GC/MS. The chemical composition of both oils was similar, with a predominance of sesquiterpene caryophyllenes. The extracts from the leaves were evaluated regarding total phenols, flavonoids and proanthocyanidins. Galled leaves showed higher levels of phenolics and proanthocyanidins, since the content of flavonoids was higher in non-galled leaves. The chromatographic profiles of extracts were obtained by using HPLC/DAD and LC-ESI-MS. Electrospray ionisation (ESI) in positive and negative ion mode was used to identify four flavones C-glycosides in both extracts. The study constitutes a first report on the chemical research of C. lanceolata. The extract from galled leaves had a higher antioxidant activity.

Clusia lanceolata; Galls; Essential oil; Phenols; Flavones; Antioxidants

N°	KI^b b Retention index relative to n-alkanes (C8-20) on the VF-5 MS capillary column.	Area^a a Percentages based on FID peak area normalization. (%)
N°		Compounds^c c Compounds presented in order of elution from the VF-5 MS capillary column.	Galled leaves	Non-galled leaves
1	856	(2E)-hexenal	0.423	0.244
2	1338	δ-elemene	0.17	0.385
3	1381	α-copaene	1.074	0.881
4	1390	β-bourbonene	0.179	-
5	1395	β-elemene	0.689	0.433
6	1411	(Z)-caryophyllene	0.262	-
7	1423	β-caryophyllene	51.624	57.159
8	1436	β-copaene	0.286	0.134
9	1444	aromadendrene	0.622	0.498
10	1454	spirolepechinene	0.218	-
11	1463	α-caryophyllene	8.422	8.941
12	1467	allo-aromadendrene	5.430	6.389
13	1480	γ-muurolene	1.183	1.006
14	1487	germacrene D	4.333	6.906
15	1494	β-selinene	-	0.331
16	1497	viridiflorene	2.461	2.091
17	1502	bicyclogermacrene	2.582	2.942
18	1510	δ-amorphene	-	0.343
19	1517	γ-cadinene	0.671	0.563
20	1522	δ-cadinene	1.817	2.299
21	1562	germacrene B	0.815	0.974
22	1576	caryophyllenyl alcohol	-	0.316
23	1574	palustrol	0.532	-
24	1583	caryophyllene oxide	6.817	0.481
25	1591	globulol	0.642	0.432
26	1601	viridiflorol	0.833	-
27	1603	ledol	0.542	0.952
28	1611	eudesmol	-	1.065
29	1614	humulene 1,2-epoxide	1.263	-
30	1626	junenol	1.269	1.172
31	1647	epi-α-muurolol	0.899	0.905
32	1659	α-cadinol	1.532	1.293
Total			97.60	99.13

Peak	t_R (min)	λmax (nm)	[M+H]⁺/[M-H]^-	MS/MS (m/z) (ESI)^-	Compound identification
1	18.552	267, 348	449/447	357, 327	orientin
2	18.907	269, 349	449/447	429, 357, 327	isoorientin
3	20.170	268, 339	579/577	431, 413, 293	vitexin-2”-O-rhamnoside
4	21.531	270, 339	579/577	457, 431, 413, 293	isovitexin-2”-O-rhamnoside

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[1] *Corresponding author. E-mail: rafaellaoliveira@ufrrj.br (R.O. Ferreira).