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

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

doi:10.1590/2175-7860202071045

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

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

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Myrcia splendens is popularly known as “guamirim-de-folha-miúda”, and its occurrence ranges from Mexico to southern Brazil. The aim of this work was to identify and quantify phenolic compounds in the crude hydroalcoholic (EBH), ethyl acetate (EBAE) and dichloromethane (EBDM) extracts using the HPLC-ESI- MS/MS. In total, 15 compounds, including protocatecuic acid, syringic acid, p-coumaric acid, salicylic acid, isoquercetin, ellagic acid, ferulic acid, umbelliferone, coniferaldehyde, sinapaldehyde, carnosol, gallic acid, syringaldehyde, umbelliferone, coniferaldehyde, myricetin and kaempferol were identified. Ellagic acid was the major compound in all extracts.

Key words:
HPLC-ESI-MS/MS; Myrcia splendens; phenolics; quantification

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