Paganelli, Camila Jeriane; Siebert, Diogo Alexandre; Vitali, Luciano; Micke, Gustavo Amadeu; Alberton, Michele Debiasi

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Sumário

Pharmacognosy • Rodriguésia 71 • 2020 • https://doi.org/10.1590/2175-7860202071045 copiar

Quantitative analysis of phenolic compounds in crude extracts of Myrcia splendens leaves by HPLC-ESI-MS/MS

Autoria SCIMAGO INSTITUTIONS RANKINGS

Resumo

Myrcia splendens é conhecida popularmente por “guamirim-de-folha-miúda”, e sua ocorrência vai desde o México até o sul do Brasil. Poucos estudos sobre sua composição química existem na literatura, sendo assim, este trabalho teve por objetivo identificar e quantificar substâncias fenólicas nos extratos brutos hidroalcoólico (EBH), acetato de etila (EBAE) e diclorometano (EBDM) através da técnica de HPLC-ESI-MS/MS. Ao total, 15 substâncias foram identificadas, incluindo ácido protocatecuico, ácido siríngico, ácido p-cumárico, ácido salicílico, isoquercetina, ácido elágico, ácido ferúlico, umbeliferona, coniferaldeído, sinapaldeído, carnosol, ácido gálico, siringaldeído, coniferaldeído, miricetina e kaempferol. O ácido elágico foi a substância majoritária em todos os extratos.

Palavras-chave:
HPLC-ESI-MS/MS; Myrcia splendens; fenólicos; quantificação

Phenolic compound	LOQ	LOD	Linear regression equation	Coeficient of determination
Gallic acid	0.39	0.11	$y = 347467 x + 388.76$	0.9742
Protocatecuic acid	0.03	0.02	$y = 1642487.86 x - 12319$	0.9865
Syringic acid	0.16	0.05	$y = 138076 x + 2427.4$	0.9985
p- Coumaric acid	0.11	0.03	$y = 1175394.92 x - 10911$	0.9907
Ferulic acid	0.03	0.02	$y = 227484 x + 2299.9$	0.9788
Syringaldehyde	0.15	0.11	$y = 48205 x + 187.54$	0.9938
Salicylic acid	0.17	0.05	$y = 1518670.32 x + 121196$	0.9895
Umbelliferone	0.04	0.03	$y = 16889 x - 2866.6$	0.9913
Myricetin	2.61	0.78	$y = 206351 x - 8351.8$	0.9952
Coniferaldehyde	0.07	0.05	$y = 454847 x - 3255.9$	0.9913
Synapaldehyde	0.24	0.07	$y = 161791 x + 1932.3$	0.9816
Ellagic acid	2.71	0.81	$y = 31742 x + 468.24$	0.9864
Kaempferol	0.91	0.57	$y = 254489 x - 127.51$	0.9943
Carnosol	0.19	0.05	$y = 714376 x + 36527$	0.9880

Phenolic compound	Rt (min)	MF	TM (Da)	EM (M-H, m/z)	MS/MS (m/z)	EBDM	EBH	EBAE	Previous studies in Myrcia
Gallic acid	3.71	C₇H₆O₅	170.12	168.90	125.00	< LOD	47.69 ± 0.196	6.29 ± 0.170	*Guldbrandsen et al. (2015)*Guldbrandsen N, De Mieri M, Gupta M, Seiser T, Wiebe C, Dickhaut J, Reingruber R, Sorgenfrei O & Hamburger M (2015) Screening of Panamanian Plant Extracts for Pesticidal Properties and HPLC-Based Identification of Active Compounds. Scientia Pharmaceutica 83: 353-367.
Protocatecuic acid	6.27	C₇H₆O₄	154.12	152.92	109.00	0.03 ± 0.005	0.36 ± 0.004	0.57 ± 0.005	*Souza Filho et al. (2006)*Souza Filho APS, Santos RA, Santos LS, Guilhon GMP, Santos AS, Arruda MSP, Muller AH & Arruda AC (2006) Allelophatic potential of Myrcia guianensis. Planta Daninha 24: 649- 656.
Syringic acid	9.91	C₉H₁₀O₅	198.17	196.93	121.10	1.18 ± 0.030	0.67 ± 0.003	0.41 ± 0.006	New in genus
p-Coumaric acid	10.32	C₉H₈O₃	164.05	162.92	119.10	0.28 ± 0.008	0.65 ± 0.018	2.15 ± 0.160	New in genus
Ferulic acid	10.65	C₁₀H₁₀O₄	194.18	192.95	134.00	0.03 ± 0.001	< LOD	< LOD	New in genus
Syringaldehyde	10.67	C₉H₁₀O₄	182.17	180.94	151.00	< LOD	< LOD	0.19 ± 0.080	New in genus
Salicylic acid	10.75	C₇H₆O₃	138.12	136.94	93.00	1.09 ± 0.008	0.75 ± 0.010	1.66 ± 0.020	New in genus
Umbelliferone	10.78	C₉H₆O₃	162.14	160.94	133.10	0.05 ± 0.001	< LOD	0.05 ± 0.001	New in genus
Isoquercetin	10.79	C₂₁H₂₀O₁₂	464.38	463.15	300.00	n.q.	n.q.	n.q.	*Saldanha et al. (2013)*Saldanha LL, Vilegas W & Dokkedal A (2013) Characterization of Flavonoids and Phenolic Acids in Myrcia bella Cambess. Using FIA-ESI-IT-MSn and HPLC-PAD-ESI-IT-MS combined with NMR. Molecules 18: 8402-8416.
Myricetin	11.22	C₁₅H₁₀O₈	318.23	316.99	151.00	< LOD	2.86 ± 0.020	< LOD	*Moresco et al. (2014)*Moresco HH, Pereira M, Bretanha LC, Micke GA, Pizzolatti MG & Brighente IMC (2014) Myricitrin as the main constituent of two species of Myrcia. Journal of Applied Pharmaceutical Science 4: 001-007.
Coniferaldehyde	11.24	C₁₀H₁₀O₃	178.18	177.01	162.00	0.24 ± 0.002	< LOD	0.08 ± 0.002	New in genus
Synapaldehyde	11.33	C₁₁H₁₂O₄	208.21	207.04	177.00	0.77 ± 0.010	< LOD	< LOD	New in genus
Ellagic acid	11.78	C₁₄H₆O₈	302.19	300.95	145.00	3.84 ± 0.080	47.97 ± 2.180	10.68 ± 0.010	*Wubshet et al. (2015)*Wubshet SG, Moresco HH, Tahtah Y, Brighente IM & Staerk D (2015) High-resolution bioactivity profiling combined with HPLC-HRMS-SPE-NMR: α-Glucosidase inhibitors and acetylated ellagic acid rhamnosides from Myrcia palustris DC. (Myrtaceae). Phytochemistry 116: 246-252.
Kaempferol	12.20	C₁₅H₁₀O₆	286.23	284.99	93.00	< LOD	0.97 ± 0.040	< LOD	*Saldanha et al. (2013)*Saldanha LL, Vilegas W & Dokkedal A (2013) Characterization of Flavonoids and Phenolic Acids in Myrcia bella Cambess. Using FIA-ESI-IT-MSn and HPLC-PAD-ESI-IT-MS combined with NMR. Molecules 18: 8402-8416.
Carnosol	13.87	C₂₀H₂₆O₄	330.42	329.16	285.20	0.24 ± 0.014	< LOD	< LOD	New in genus

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[1] 4 Author for correspondence: michele@furb.br