MELISSOPALINOLOGICAL, PHYSICOCHEMICAL ANALYSIS, ANTIRADICALAR ACTIVITY AND CHEMICAL PROFILE BY UPLC-DAD-qTOF-MS/MS OF <i>FRIESEOMELITTA DOEDERLEINI</i> (ABELHA BRANCA) HONEY BEE: COMPARISON WITH THE FLOWERS OF <i>MIMOSA TENUIFLORA</i> (JUREMA PRETA)

Santisteban, Rogelio M.; Cabrera, Sonia P.; Neto, José F.; Silva, Eva M. S.; Correia, Rebert C.; Alves, Rodolfo F.; Santos, Francisco de A. R. dos; Camara, Celso A.; Silva, Tania M. S.

doi:10.21577/0100-4042.20170407

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Artigo • Quím. Nova 42 (8) • Aug 2019 • https://doi.org/10.21577/0100-4042.20170407 copy

MELISSOPALINOLOGICAL, PHYSICOCHEMICAL ANALYSIS, ANTIRADICALAR ACTIVITY AND CHEMICAL PROFILE BY UPLC-DAD-qTOF-MS/MS OF FRIESEOMELITTA DOEDERLEINI (ABELHA BRANCA) HONEY BEE: COMPARISON WITH THE FLOWERS OF MIMOSA TENUIFLORA (JUREMA PRETA)

Authorship SCIMAGO INSTITUTIONS RANKINGS

Melissopalynological, physicochemical analysis, mineral content, antiradical activity and profile of compounds by Ultra-Performance Liquid Chromatography coupled with a Diode Array Detector and quadrupole Time of Flight Mass Spectrometry (UPLC-DAD-qTOF-MS/MS) of Frieseomelitta doederleini honeys from semiarid region of the Northeast of Brazil are presented. The melissopalynological analysis showed two principal pollen types of Mimosa tenuiflora (jurema preta) and Shinus sp (aroeira). The chemical profile data obtained by UPLC-DAD-qTOF-MS/MS of the Mimosa tenuiflora flowers (principal pollen of honey) and the five samples of F. doederleini honeys both flowers and honey showed similar profile. Abelha branca honeys samples had similar characteristic profile of phenolic compounds (flavonoids), and also antiradical activity. The main flavonoids identified in the honey samples in the jurema preta flowers were flavonols/flavone and flavanols/flavanones aglycones. All the flavonoids identified showing that the nectar collected by the bees may be from this plant species. The antiradical activity of the honey samples strongly correlated with their phenolic content. Among the minerals analyzed, potassium was the most abundant, followed by magnesium.

Keywords:
stingless bee; honey; Mimosa tenuiflora; chemical profile; antiradical activity

Tipos polínicos	Méis de abelha branca (%)
Tipos polínicos	1	2	3	4	5
Anacardiaceae
Schinus	21,9	11,1	32,2	34,8	36,1
Spondias	2,1	1,9	1,1	1,9	0,9
Euphorbiaceae
Croton	8,1	10,8	24,4	19,9	22,8
Fabaceae
Anadenanthera	0,6	0,3	0,8	0,3	0,3
Caesalpinia	14,1	3,4	3,3	5,4	9,0
Fabaceae 1		2,1
Mimosa tenuiflora	27,9	33,1	28,9	33,9	29,0
Mimosa subenervis		0,3	0,3
Prosopis	0,3
Senna macranthera	0,6		0,6	0,3
Myrtaceae
Myrcia	0,3	0,8		0,3	0,6
Malvaceae
Pseudobombax			1,7	1,6	0,3
Waltheria		1,3
Sida					0,3
Poaceae
Poaceae 1
Solanaceae
Solanum			0,3
Indeterminados^* * Frequência de tipos polínicos (quantidade de tipos polínicos).	24,0 (3)	34,9 (1)	6,4 (1)	1,6 (2)	0,6 (1)

Amostras	pH	Acidez livre (meq kg^-1)	Atividade de Agua (aw)	Umidade	Condutividade (µS cm^-1)	Açúcar redutor (%)	HMF (mg kg^-1)	Teor de cinzas (%)
1	3,68 ± 0,01	103,33 ± 1,40	0,75 ± 0,01	26,83 ± 0,28	595,33 ± 0,57	60,76 ± 0,33	4,49 ± 0,29	0,25 ± 0,05
2	3,79 ± 0.01	94,16 ± 1,44	0,73 ± 0,01	26,66 ± 0,57	651,66 ± 0,57	60,56 ± 0,33	4,13 ± 0,31	0,22 ± 0,01
3	3,82 ± 0,01	94,16 ± 1,44	0,76 ± 0,01	27,33 ± 0,57	587,66 ± 0,57	60,00 ± 0,32	3,04 ± 0,17	0,18 ± 0,03
4	3,92 ± 0,01	90,00 ± 2,50	0,75 ± 0,01	27,33 ± 0,57	631,33 ± 0,57	60,00 ± 0,32	5,23 ± 0,68	0,20 ± 0,03
5	3,91 ± 0,01	85,83 ± 1,44	0,70 ± 0,02	27,46 ± 0,05	631,33 ± 0,57	59,44 ± 0,31	4,74 ± 0,22	0,26 ± 0,01

Amostra de mel	K	Mg	Na	Ca
1	1259,60 ± 16,90	40,31 ± 0,56	11,81 ± 0,50	6,58 ± 0,50
2	1260,98 ± 33,57	40,23 ± 0,66	9,92 ± 0,49	6,21 ± 0,43
3	1287,41 ± 38,04	35,98 ± 0,81	12,66 ± 0,28	5,16 ± 0,44
4	1145,73 ± 8,53	35,19 ± 0,56	17,13 ± 1,92	5,58 ± 0,59
5	1334,07 ± 37,64	40,22 ± 0,46	13,20 ± 1,54	5,50 ± 0,43

	RT (min)	λ_max (nm)	[M-H]^- (m/z)	[M-H]^- (m/z) Calculado		Tentativa de identificação
1	2,15	364	300,9997	300,9990	257,0072 [M-H-CO₂]^-, 229,9945 [M-H-CO₂-CO]^-, 185,0241 [M-H-CO₂-CO]^-	Ácido elágico^* * Comparado com padrão autentico.
2	2,49	293	177,0193	177,0193	133,0292 [M-H-CO₂]^-, 105,0334 [M-H-CO]^-, 89,0383 [M-H-2CO₂]^-	Dihidroxicumarina
3	2,77	-	543,2815	-		Não identificado
4	3,52	-	573,2867	-		Não identificado
5	3,65	345	477,1039	477,1039	315,0502 [M-H-glicose]^-	Isoramnetina-glicosídeo
6	3,99	287	287,0558	287,0561	259,9099 [M-H-CO]^-	Tetrahidroxi-flavanona
7	4,15	359	285,0400	285,0405	257,0378 [M-H-CO]^-	Luteolina^* * Comparado com padrão autentico.
8	4,36	345	301,0305	301,0353	283,0178 [M-H-H₂O]^-, 273,0399[M-H-CO]^-	Quercetina^* * Comparado com padrão autentico.
9	4,52	345	331,0437	331,0459	316,0200 [M-H-CH₃]^-, 301,0304 [M-H-2CH₃]^-, 272,0483 [M-2H-2CH₃-CO]^-	Pentahidroxi-metoxi-flavona
10	4,59	356	315, 0576	315,0510	300,0258 [M-H-CH₃]^-, 271,0230 [M-2H-CH₃-CO]^-, 272,0288 [M-H-CH₃-CO]^-, 255,0301 [M-2H-CH₃-CO-H₂O]^-	Tetra-hidroxi-metoxi-flavona
11	4,74	358	345,0608	345,0608	330,0374 [M-H-CH₃]^-, 315,0137 [M-H-2CH₃]^-, 287,0194 [M-H-2CH₃-CO]^-	Pentahidroxi-dimetoxi-flavona
12	4,80	288	271,0606	271,0611	253,0455 [M-H-H₂O]^-	Naringerina^* * Comparado com padrão autentico.
13	4,89	345	269,0451	269,0455	241,3104 [M-H-CO]^-	Apigenina^* * Comparado com padrão autentico.
14	5,04	290	301,0790	301,0716	286,0473 [M-H-CH₃]^-	Trihidroxi-metoxi-flavanona
15	5,10	288	301,0710	301,0716	285,0385 [M-2H-CH₃]^-	Trihidroxi-metoxi-flavanona
16	5,16	360	315,0505	315,0510	300,0261 [M-H-CH₃]^-, 272,0299 [M-H-CH₃-CO]^-, 271,0230 [M-2H-CH₃-CO]^-, 243,0287 [M-2H-CH₃-2CO]^-	Tetrahidroxi-metoxi-flavona
17	5,22	286	301,0701	301,0716	286,0464 [M-H-CH₃]^-	Trihidroxi-metoxi-flavanona
18	5,28	345	315,0506	315,0510	300,0238 [M-H-CH₃]^-, 283,0275 [M-H-CH₃-H₂O]^-, 271,0248 [M-2H-CH₃-CO]^-, 255,0301 [M-2H-CH₃-CO-H₂O]^-,227,0358 [M-2H-CH₃-H₂O-2CO]^-	Isoramnetina^* * Comparado com padrão autentico.

19	5,35	346	329,0638	329,0666	314,0409 [M-H-CH₃]^-, 299,0177 [M-H-2CH₃]^-, 271,0231 [M-H-2CH₃-CO]^-	Tetrahidroxi-dimetoxi-flavona
20	5,44	349	299,0558	299,0561	284,0302 [M-H-CH₃]^-, 255,0276 [M-2H-CH₃-CO]^-, 227,0328 [M-2H-CH₃-2CO]^-	Trihidroxi-metoxi-flavona
21	5,61	339	329,0663	329,0666	314,0415 [M-H-CH₃]^-, 299,0180 [M-H-2CH₃]^-, 271,0232 [M-H-2CH₃-CO]^-	Trihidroxi-dimetoxi-flavona
22	5,67	355	329,0663	329,0666	314,0394 [M-H-CH₃]^-, 299,0163 [M-H-2CH₃]^-, 271,0261[M-H-2CH₃-CO]^-, 243,0272	Trihidroxi-dimetoxi-flavona
23	5,84	346	359,0772	359,0772	344,0544 [M-H-CH₃]^-, 329,0302 [M-H-2CH₃]^-, 301,0359 [M-H-2CH₃-CO]^-, 286,0110 [M-H-3CH₃-CO]^-	Trihidroxi-trimetoxi-flavona
24	5,98	286	301,0716	301,0716	283,0501 [M-H-H₂O]^-	Trihidroxi-metoxi-flavanona
25	6,12	287	315,0878	315,0874	285,0410 [M-H-2CH₃]^-	Dihidroxi-metoxi-flavanona
26	6,23	333	313,0714	313,0717	298,0471 [M-H-CH₃]^-, 283,0235 [M-H-2CH₃]^-, 255, 0291 [M-H-2CH₃-CO]^-	Dihidroxi-dimetoxi-flavona
27	6,30	359	329,0666	329,0666	314,0435 [M-H-CH₃]^-, 299,0202 [M-H-2CH₃]^-, 271,0266 [M-H-2CH₃-CO]^-	Trihidroxi-dimetoxi-flavona
28	6,59	357	329,0655	329,0666	314,0415 [M-H-CH₃]^-, 299,0178 [M-H-2CH₃]^-, 271,0234 [M-H-2CH₃-CO]^-	Trihidroxi-dimetoxi-flavona
29	6,72	245	343,0808	343,0823	328,0567 [M-H-CH₃]^-, 313,0329 [M-H-2CH₃]^-, 298,0099 [M-H-3CH₃]^-	Dihidroxi-trimetoxi-flavona
30	6,94	287	285,0762	285,0768	269,0383 [M-2H-CH₃]^-	7-metoxi-naringenina^* * Comparado com padrão autentico.
31	7,11	345	283,0610	283,0611	268,0362 [M-H-CH₃]^-	Dihidroxi-metoxi-flavona
32	7,32	346	313,0714	313,0718	298,0453 [M-H-CH₃]^-, 283,0211 [M-H-2CH₃]^-, 255, 0273 [M-H-2CH₃-CO]^-	Dihidroxi-dimetoxi-flavona
33	7,59	357	313,0694	313,0718	298,0453 [M-H-CH₃]^-, 283,0211 [M-H-2CH₃]^-, 255, 0267 [M-H-2CH₃-CO]^-	Dihidroxi-dimetoxi-flavona
34	7,82	345	343,0811	343,0813	328,0560 [M-H-CH₃]^-, 313,0325 [M-H-2CH₃]^-, 285,0378 [M-H-2CH₃-CO]^-, 270,0139 [M-H-3CH₃-CO]^-	Hidroxi-trimetoxi-flavona

	[M-H]^-	Flavonoides	^0,2A^-	^0,2B^-	^0,4B^-	^1,3A^-	^1,3B^-	[M-H-B]^-	[M-H-B-CH₃]^-
6	287,0558	Tetrahidroxi-flavanona		135,0444		151,0029
7	285,0400	Luteolina				151,0029	133,0291	193,0128
8	301,0305	Quercetina				151,0036	133,0266
9	331,0437	Pentahidroxi-metoxi-flavona						223,0232	208,0002
10	315,0576	Tetrahidroxi-metoxi-flavona				151,0057	148,0146
11	345,0608	Pentahidroxi-dimetoxi-flavona			175,0050
12	271,0606	Naringerina		119,0494		151,0027		177,0188
13	269,0451	Apigenina		119,0499		151,0031
14	301,0790	Trihidroxi-metoxi-flavanona	165,9903	119,0496		151,0935
15	301,0710	Trihidroxi-metoxi-flavanona				151,0031		177,0190
16	315,0505	Tetrahidroxi-metoxi-flavona				165,9903
17	301,0701	Trihidroxi-metoxi-flavanona				151,0023
18	315,0506	Isoramnetina	163,0033	149,0207		151,0029	162,9986
19	329,0638	Trihidroxi-dimetoxi-flavona				151,0029		193,0130
20	299,0558	Trihidroxi-metoxi-flavona	183,0439
21	329,0663	Trihidroxi-dimetoxi-flavona	165,9888
22	329,0663	Trihidroxi-dimetoxi-flavona						193,0482
23	359,0772	Trihidroxi-trimetoxi-flavona	195,8101
24	301,0716	Trihidroxi-metoxi-flavanona	165,0181						135,0441
25	315,0878	Dihidroxi-metoxi-flavanona	165,0184
26	313,0714	Dihidroxi-dimetoxi-flavona	163,0037			151,0030
27	329,0666	Trihidroxi-dimetoxi-flavona	199,0377
28	329,0655	Trihidroxi-dimetoxi-flavona	181,0505
29	343,0808	Dihidroxi-trimetoxi-flavona	197,0455
30	285,0762	7-metoxi-naringenina*	177,0483	119,0772		165,0466	119,0772
31	283,0610	Dihidroxi-metoxi-flavona	151,0031
32	313,0714	Dihidroxi-dimetoxi-flavona
34	313,0694	Dihidroxi-dimetoxi-flavona	183,0424
35	343,0811	Hidroxi-trimetoxi-flavona						193,0808

Amostras	Teor de fenólicos (mg EAG g^-1 Mel)	Teor de flavonoides (mg EQ g^-1 Mel)	DPPH CE₅₀ (mg mL^-1)	ABTS CE₅₀ (mg mL^-1)
B1	1,21 ± 0,02	0,15 ± 0,02	14,32 ± 0,82	4,76 ± 0,04
B2	1,16 ± 0,01	0,18 ± 0,02	13,81 ± 0,31	5,51 ± 0,08
B3	1,21 ± 0,06	0,16 ± 0,01	13,17 ± 0,81	4,21 ± 0,97
B4	1,15 ± 0,03	0,16 ± 0,00	10,38 ± 0,45	5,26 ± 0,19
B5	1,23 ± 0,02	0,15 ± 0,00	15,24 ± 0,11	4,95 ± 0,08

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