Composição fenólica de Jussara (Euterpe edulisMartius) de Minas Gerais e Espírito Santo, Brasil, determinada por cromatografia líquida de alta eficiência acoplada à detecção de arranjo de diodos e espectrometria de massa contendo sistema de ionização por eletrospray (HPLC-DAD-ESI MS/MS)

Dadalto, Carolina Tatagiba da Rocha; Hermosín-Gutiérrez, Isidro; Pérez-Navarro, José; Ojeda-Amador, Rosa Maria; Gómez-Alonso, Sergio; Stringheta, Paulo César; Paula, Daniele de Almeida; Pinto, Marcos Roberto Moacir Ribeiro; Ramos, Afonso Mota

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FOOD TECHNOLOGY • Cienc. Rural 53 (7) • 2023 • https://doi.org/10.1590/0103-8478cr20210900 copiar

Composição fenólica de Jussara (Euterpe edulisMartius) de Minas Gerais e Espírito Santo, Brasil, determinada por cromatografia líquida de alta eficiência acoplada à detecção de arranjo de diodos e espectrometria de massa contendo sistema de ionização por eletrospray (HPLC-DAD-ESI MS/MS)

Autoria SCIMAGO INSTITUTIONS RANKINGS

RESUMO:

O objetivo desta pesquisa foi avaliar a composição fenólica da polpa de Jussara dos Estados brasileiros de Minas Gerais (MG) e Espírito Santo (ES) usando HPLC-DAD-MS / MS. Dezessete antocianinas foram detectadas, dentre elas, derivadas de cianidina, pelargonidina e peonidina. Dentre os compostos fenólicos não antociânicos, foram identificados flavonóis (derivados de caempferol, quercetina e isorhamnetina), flavan-3-ols (catequina, epicatequina, procianidinas do tipo B e dímeros desconhecidos) e resveratrol em sua forma glicosilada. Catequina (32,41-60,56 mg 100g^-1) e epicatequina (18,86-40,92 mg 100g^-1) foram os principais flavan-3-óis presentes nas frutas. As amostras apresentaram pequenas concentrações de glicosídeos resveratrol (0,02-0,91 mg 100g^-1). A metodologia analítica utilizada (HPLC-DAD-ESI-MS / MS) permitiu a identificação de novos compostos relatados presentes na composição da polpa de Jussara.

Palavras-chave:
antocianinas; flavonóis; derivados do ácido hidroxicinâmico; flavan-3-ols; fruta jussara; HPLC-DAD-ESI-MS/MS

Autoria

Carolina Tatagiba da Rocha Dadalto

Departamento de Ciência e Tecnologia de Alimentos, Universidade Federal de Viçosa (UFV), Viçosa, MG, Brasil.Universidade Federal de Viçosa (UFV)BrazilViçosa, MG, BrazilDepartamento de Ciência e Tecnologia de Alimentos, Universidade Federal de Viçosa (UFV), Viçosa, MG, Brasil.

https://orcid.org/0000-0003-3080-626X

Isidro Hermosín-Gutiérrez

Universidad de Castilla-La Mancha, Ciudad Real, Castilla-La Mancha, ES.Universidad de Castilla-La ManchaSpainCiudad Real, Castilla-La Mancha, SpainUniversidad de Castilla-La Mancha, Ciudad Real, Castilla-La Mancha, ES.

https://orcid.org/0000-0003-2343-5157

José Pérez-Navarro

https://orcid.org/0000-0003-1614-0633

Rosa Maria Ojeda-Amador

https://orcid.org/0000-0002-1047-0677

Sergio Gómez-Alonso

https://orcid.org/0000-0002-2358-6636

Paulo César Stringheta

https://orcid.org/0000-0002-1229-7038

Daniele de Almeida Paula ^*E-mail: daniele.paula@ifpr.edu.br. *Corresponding author

Instituto Federal de Educação, Ciência e Tecnologiado Paraná (IFPR), 85935-000, Assis Chateaubriand, PR, Brasil..Instituto Federal de Educação, Ciência e Tecnologiado Paraná (IFPR)BrazilAssis Chateaubriand, PR, BrazilInstituto Federal de Educação, Ciência e Tecnologiado Paraná (IFPR), 85935-000, Assis Chateaubriand, PR, Brasil..

https://orcid.org/0000-0002-6327-3503

Marcos Roberto Moacir Ribeiro Pinto

Instituto Federal de Educação, Ciência e Tecnologia do Espírito Santo (IFES), Venda Nova do Imigrante, ES, Brasil.Instituto Federal de Educação, Ciência e Tecnologia do Espírito Santo (IFES)BrazilVenda Nova do Imigrante, ES, BrazilInstituto Federal de Educação, Ciência e Tecnologia do Espírito Santo (IFES), Venda Nova do Imigrante, ES, Brasil.

https://orcid.org/0000-0002-7971-203X

Afonso Mota Ramos

https://orcid.org/0000-0001-9435-7745

E-mail: daniele.paula@ifpr.edu.br. ^*Corresponding author

Editors: Leandro Souza da Silva(0000-0002-1636-6643)

Juliane Welke(0000-0003-0365-3683)

DECLARATION OF CONFLICT OF INTEREST

There is no conflict of interest regarding the development and publication of the study.

AUTHORS’ CONTRIBUTIONS

All authors contributed equally for the conception and writing of the manuscript. All authors critically revised the manuscript and approved of the final version.

SCIMAGO INSTITUTIONS RANKINGS

Figuras | Tabelas

Figuras (2)
Tabelas (4)

Thumbnail

Figure 1
HPLC-DAD chromatogram (detection at 520 nm) for the anthocyanins from Jussara fruit pulp (sample from Araponga, MG, Brazil). Peaks numbering indicated in the table 2.

Thumbnail

Figure 2
HPLC-DAD chromatogram (detectionat360 nm) for the flavanols from Jussara fruit pulp (sample from Araponga, MG, Brazil). Peaks numbering indicated in the table 3.

Thumbnail

Table 1
Geographic data of the regions where the jussara samples were collected.

Thumbnail

Table 2
Retention time, mass spectra and molar percentage of anthocyanins identified in the Jussara fruit pulp.

Thumbnail

Table 3
Retention time, mass spectra and molar percentage of flavonols identified in the Jussara fruit pulp.

Thumbnail

Table 4
Retention time, mass spectra and molar percentage of the flavan-3-ol monomers and dimers, and stilbenes identified in samples of the Jussara fruit pulp by means of MRM^* experiments.

Figure 1 HPLC-DAD chromatogram (detection at 520 nm) for the anthocyanins from Jussara fruit pulp (sample from Araponga, MG, Brazil). Peaks numbering indicated in the table 2.

Figure 2 HPLC-DAD chromatogram (detectionat360 nm) for the flavanols from Jussara fruit pulp (sample from Araponga, MG, Brazil). Peaks numbering indicated in the table 3.

Table 1 Geographic data of the regions where the jussara samples were collected.

Região	UF	Month of harvest	Latitude^*	Longitude^*	Altitude^*
Rio Novo do Sul	ES	May	S20º48`34.529”	W40º56`05.826”	452
Viçosa	MG	June	S20º47`28.082”	W42º52`45.120”	685
Rio Pomba	MG	June	S21º9`6.062”	W43º8`19.397”	839
Canaã	MG	July	S20º41`16.881”	W42º36`15.417”	759
Araponga	MG	July	S20º41`06.609”	W42º32`12.001”	959
Rosário de Limeira	MG	September	S20º53`58.275”	W42º32`41.884”	1092
Vargem Alta	ES	November	S20°31'47.900"	W40°58'33.500"	1058

^*Data obtained by GPS. Altitude (m).UF: Federative Unit. MG: Minas Gerais. ES: Espírito Santo.

Table 2 Retention time, mass spectra and molar percentage of anthocyanins identified in the Jussara fruit pulp.

-----------------------------------------------------------------% Molar----------------------------------------------------------------------

eak¹

Assignment^*

λ_max (nm)

_t(min)

M]⁺(m/z)

S/MS (m/z)

ARA

CAN

VIC

cy-3,5-diglc

94, 508

.21

49, 287

0.09±0.01

cy-3-gal

79, 515

.32

0.57±0.08^a

0.19±0.06^b

cy-3-soph

279, 515

.50

0.17±0.01^a

0.05± 0.00^b

0.12±0.04^a

0.13±0.01^a

0.12±0.02^a

cy-3-glc

80, 514

0.31

52.43±0.56^a

34.57±2.75^c

42.93±6.54^bc

41.68±2.16^bc

43.81±1.23^ab

37.77±1.16^bc

39.44±4.32^bc

cy-3-pentgal

80, 514

0.60

49, 287

0.45±0.05^b

0.58±0.09^ab

0.76± 0.11^a

0.55±0.02^ab

0.66±0.21^ab

0.54±0.07^ab

0.47±0.07^ab

cy-3-rhmgal

80, 514

1.00

49, 287

1.01±0.10^a

0.91±0.04^ab

1.02±0.11^a

0.95±0.24^a

0.57±0.15^b

1.01±0.10^a

0.85±0.07^ab

cy-3-pentglc

80, 514

1.10

49, 287

2.92±0.05^bc

3.45±0.23^ab

4.14±0.76^a

2.89±0.46^bc

2.14± 0.32^c

2.48± 0.13^bc

2.39±0.35^bc

cy-3-rhmglc

81, 516

2.75

49/287

38.09±0.29^c

59.17±3.12^a

48.34±7.29^b

51.14±2.48^ab

51.11±1.11^ab

56.72±1.07^ab

54.47±4.54^ab

pg-3-glc

81, 516

3.39

2.44±0.17^a

0.26±0.19^b

1.14±0.98 ^b

0.66±0.34 ^b

0.69±0.09 ^b

0.39± 0.07 ^b

0.66±0.25 ^b

pg-3-rhmglc

6.06

33, 271

0.65±0.08^ab

0.23±0.12^b

0.46± 0.43^b

0.45±0.06^b

1.02±0.15^a

0.41±0.03^b

0.54±0.17^ab

cy-3-rhm

6.16

0.47±0.06^abc

0.19±0.03^d

0.47±0.10^bc

0.52±0.12^ab

0.28±0.08^cd

0.68±0.02^a

pn-3-glc

6.50

0.12±0.00^ab

0.08±0.01^b

0.13±0.03^ab

0.15±0.04^a

cy-3-pent

6.81

0.17±0.02^a

0.10±0.01^b

0.17±0.02^a

0.14±0.03^ab

pn-3-rhmglc

72, 517

8.67

463, 301

0.22±0.02^b

0.29±0.06^ab

0.20±0.06^b

0.34±0.07^ab

0.28±0.02^ab

0.50±0.20^a

cy-3-rhm-iso

80, 519

2.13

0.10±0.02^ab

0.05±0.01^b

0.12±0.04^ab

0.13±0.03^a

385-glc

87, 527

4.66

0.05±0.00^a

0.02±0.00^b

0.03±0.01^ab

385-rhmglc

4.92

47, 385

0.04±0.00^a

0.04±0.01^a

0.05±0.02^a

Total cy

96.48±0.21^b

99.07±0.31^a

98.08±1.46^ab

98.32±0.27^ab

98.29±0.08^ab

98.92±0.08^a

97.85±0.92^ab

Total pg

3.09±0.20^a

0.50±0.30^b

1.60±1.40^ab

1.10±0.40^b

1.71±0.08^ab

0.80±0.09^b

1.20±0.42^b

Total pn

0.34±0.01^a

0.37± 0.07^a

0.33±0.08^a

0.49±0.10^a

0.28±0.02^a

0.50±0.20^a

Total²

96.37±11.00^b

737.00±341.00^a

98.10±30.90^b

318.60±120.50^b

11.97±6.08^b

96.36±2.91^b

61.30±22.70^b

^*cy, cyanidin; pg, pelargonidin; pn, peonidin; diglc, diglucoside; gal, galactoside; soph, sophoroside; glc, glucoside; pent, pentoside; rhm, rhamnoside; ARA, Araponga; CAN, Canaã; RL, Rosário de Limeira; RN, Rio Novo do Sul; RP, Rio Pomba; VA, Vargem Alta; VIC, Viçosa; Underlined m/z value in the MS/MS spectra indicated the most intense signal. ¹Peak numbers used in Figure 1.²expressed in mg of cy 3-rhmglc/100 g of fruit. ³NQ, non quantified.. Different superscript letters between regions denote significant differences.

Table 3 Retention time, mass spectra and molar percentage of flavonols identified in the Jussara fruit pulp.

% Molar⁴

Peak¹

Assignment^*

λ_max (nm)

R_t (min)

[M+H]⁺ (m/z)

MS/MS (m/z)

ARA

CAN

VIC

q-3-gal

255, 288 sh, 322 sh, 341

23.2

465

303

2.79±0.82^ab

1.34±0.52^bc

3.68±0.90 ^a

1.45±0.68^bc

2.41±0.36^ab

0.33±0.09^c

q-3-glc

360

26.6

465

303

3.20±0.82^b

11.05±4.68^a

8.76±2.62^ab

9.40±0.27^ab

7.88±0.78^ab

11.98±0.40^a

9.28±2.72^ab

k-3-gal

284, 312 sh, 347

27.1

449

287

q-3-rhmglc

255, 289 sh, 346

27.9

611

465, 303

23.41±0.28^b

54.91±5.02^a

44.32±8.48^a

45.91±5.42^a

50.64±1.52^a

54.64±0.78^a

45.78±8.78^a

k-3-glc

352

29.3

449

287

48.15±1.52^a

16.78±6.00^bc

19.87±4.09^b

20.20±2.79^b

7.58±0.71^cd

1.79±0.43^d

9.86±7.16^bcd

q-3-(6”-mal)-glc

30.9

551

303

1.22±0.18^bc

0.89± 0.36^c

2.04±0.50^ab

1.80±0.51^abc

1.60±0.21^abc

2.23±0.11^a

k-3-rhmglc

265, 284 sh, 346

38.1

595

449, 287

15.81±0.98^abc

7.73±4.60^c

14.39±6.11^abc

12.35±3.86^bc

22.87±1.31^a

16.78±0.58^abc

16.99±0.41^ab

i-3-gal

39.7

479

317

i-3-glc

42.5

479

317

0.49±0.29^b

1.01±0.12^a

0.56± 0.09^b

0.45±0.03^b

k-3-(6”-mal)-glc

347

43.0

535

287

0.85±0.04^a

0.54±0.10^b

i-3-rhmglc

356

43.8

625

317

2.90±0.04^c

6.64±1.74^b

5.15±0.93^bc

5.97±1.16^bc

8.22±0.65^ab

10.25±0.94^a

6.73±1.77^b

k-3-(2”-mal)-glc

46.5

535

449, 287

1.18±0.19^b

1.53±0.35^b

2.93±1.00^b

2.69±1.36^b

7.80±0.71^a

Total kaempferol

65.99±1.23^a

26.05±10.17^bc

37.19±8.78^b

35.24±5.21^bc

30.45±0.62^bc

18.57±0.17^c

35.19±7.96^bc

Total quercetin

30.62±0.95^b

67.31±9.12^a

57.66±9.64^a

58.79±6.35^a

60.32±1.20^a

70.62±1.13^a

57.63±6.20^a

Total isoramnetin

3.39±0.28^d

6.64±1.74^bcd

5.15±0.934^cd

5.97±1.16^bcd

9.23±0.65^ab

10.81±1.03^a

7.18±1.77^bc

Total flavonols²

28.52±4.84 ^b

89.20±39.00^a

15.08±4.19^b

42.27±3.48^b

7.90±1.25^b

15.99±0.88^b

18.90±1.99^b

^*Q, quercetin; K, kaempferol; I, isorhamnetin; gal, galactoside; glc, glucoside; rhmglc, 6”-rhamnosyl-glucoside; (6”-mal)-glc, 6”-malonyl-glucoside; ARA, Araponga; CAN, Canaã; RL, Rosário de Limeira; RN, Rio Novo do Sul; RP, Rio Pomba; VA, Vargem Alta; VIC, Viçosa; Underlined m/z value in the MS/MS spectra indicated the most intense signal; ¹Peak numbers used in Figure 2. ²expressed in mg of kaempferol-3-glucoside/100 g of fruit.³NQ, nonquantified. ⁴Results as mean ± SD from triplicates. Different superscript letters between regions denote significant differences.

Table 4 Retention time, mass spectra and molar percentage of the flavan-3-ol monomers and dimers, and stilbenes identified in samples of the Jussara fruit pulp by means of MRM^* experiments.

				------------------------------------------------------------------------%Molar--------------------------------------------------------------------------------
Compound	R_t (min)	[M-H]^- (m/z)	MS/MS (m/z)	ARA	CAN	RL	RN	RP	VA	VIC
---------------------------------------------------------------------------------------------------------------Flavan-3-ols----------------------------------------------------------------------------------------------------------------
(+)-catechin	25.60	289	164, 137	42.69±5.31^b	36.53±11.29^b	46.49±4.55^ab	32.41±4.95^b	60.56±0.56^a	35.98±1.83^b	32.77±9.06^b
(-)-epicatechin	32.64	289	164, 137	36.82±3.54^a	39.40±4.90^a	32.58±0.81^a	40.84±7.49^a	18.86±0.59^b	39.11±2.15^a	40.92±7.32^a
PB1	21.80	577	425; 407	7.09±1.12^ab	7.50±1.75^ab	7.37±2.53^ab	7.36±1.12^ab	6.08±0.61^b	5.84±0.07^b	10.24±1.25^a
PB2	27.40	577	425; 407	1.14±0.19^bc	2.12±0.48^ab	0.96±0.07^c	2.40±0.85^a	1.06±0.13^bc	2.15±0.36^ab	1.47±0.10^abc
PB4	23.10	577	425; 407	0.17± 0.04^b	nq	0.18±0.03^b	0.34±0.10^a	nq	nq	nq
dimer-3	20.43	577	425; 407	8.00±0.15^a	10.05±3.13^a	8.83±2.45^a	10.06±3.94^a	10.06±0.91^a	11.17± 0.51^a	8.17± 0.91^a
dimer-4	26.10	577	425; 407	2.80±0.65^ab	3.79±1.11^ab	2.20±0.72^ab	4.99±1.63^a	1.88±0.34^b	4.45±1.30^ab	4.86±1.43^ab
dimer-5	30.80	577	425; 407	0.64±0.04^a	nq	0.70±0.22^a	0.78±0.09^a	0.68±0.19^a	0.53±0.11^a	0.80±0.12^a
dimer-6	32.00	577	425; 407	0.50±0.05^a	0.58± 0.11^a	0.55±0.19^a	0.57±0.08^a	0.66±0.04^a	0.66±0.04^a	0.54±0.18^a
dimer-7	38.30	577	425; 407	0.14±0.016^ab	nq	0.13± 0.01^b	0.25±0.05^a	0.16±0.02^ab	0.20± 0.06^ab	0.21±0.06^ab
Total flavan-3-ols¹				39.02±14.80^ab	36.42±15.77^ab	15.82±4.26^ab	49.9±27.7^a	9.75±3.86^b	14.42±4.87^ab	22.59±10.54^ab
----------------------------------------------------------------------------------------------------------------Stilbenes-------------------------------------------------------------------------------------------------------------------
trans-resveratrol-3-O-glucoside	38.25	389	227; 185	52.18±2.59^ab	90.79±3.88^a	68.76±6.61^ab	48.77±9.69^ab	42.00±41.70^ab	40.93±4.06^ab	25.00±43.20^b
cis-resveratrol-3-O-glucoside	43.80	389	227; 185	47.82±2.59^ab	9.21±3.88^b	31.24±6.61^ab	51.23±9.69^ab	58.00±41.70^ab	59.07±4.06^ab	75.00±43.20^a
Total resveratrol²				0.09±0.01^b	0.91±0.61^a	0.12±0.05^ab	0.69±0.45^ab	0.01± 0.00^b	0.09±0.05^b	0.02±0.01^b

^*ARA, Araponga; CAN, Canaã; RL, Rosário de Limeira; RN, Rio Novo do Sul; RP, Rio Pomba; VA, Vargem Alta; VIC, Viçosa; The m/z value in the [M-H]^-column corresponds to the deprotonated molecule generated in the MS spectra, whereas the couple of m/z values in the MS/MS column are the selected fragment ions used for the identification of each compound.¹mg of catechin/100 g of fruit.²mg of resveratrol glycoside/100 g of fruit..Different superscript letters between regions denote significant differences.

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Métricas

Composição fenólica de Jussara (Euterpe edulisMartius) de Minas Gerais e Espírito Santo, Brasil, determinada por cromatografia líquida de alta eficiência acoplada à detecção de arranjo de diodos e espectrometria de massa contendo sistema de ionização por eletrospray (HPLC-DAD-ESI MS/MS)

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[1] E-mail: daniele.paula@ifpr.edu.br. ^*Corresponding author