HPLC-ESI-MS and GC-EI-MS Identification and Quantitation of Polyphenolics and Alkaloids in Moroccan Jujube Honeys

Farid Khallouki; Mourad Akdad; Toufik Bouddine; Lhoussain Hajji; Robert W. Owen

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HPLC-ESI-MS and GC-EI-MS Identification and Quantitation of Polyphenolics and Alkaloids in Moroccan Jujube Honeys

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| 18 gru 2020

Journal of Apicultural Science

Tom 64 (2020): Zeszyt 2 (December 2020)

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Article Category: Original paper

Data publikacji: 18 gru 2020

Zakres stron: 287 - 299

Otrzymano: 06 lut 2020

Przyjęty: 14 wrz 2020

DOI: https://doi.org/10.2478/jas-2020-0029

Słowa kluczowe
4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside, 4-hydroxyquinoline glucoside, 4-hydroxyquinoline, Jujube honey, kynurenic acid, methyl syringate, phenolic acid

© 2020 Farid Khallouki et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Analytical HPLC-DAD-ESI-MS chromatogram (at 278, 257 and 320 nm) of a Moroccan Jujube (Ziziphus lotus) honey (10g) dissolved in doubly distilled water (50.0 mL) I. 4-hydroxyquinoline glucoside, II. 4-hydroxyquinoline, III. p-hydroxybenzoic acid, IV. caffeic acid, V. kynurenic acid, VI. methyl syringate.

Analytical HPLC-DAD-ESI-MS chromatogram (at 257 and 320 nm) of a SPE (10% methanol) fraction of Moroccan Jujube (Ziziphus lotus) honey (10g) I. 4-hydroxyquinoline glucoside, II. 4-hydroxyquinoline, III. p-hydroxybenzoic acid.

Analytical HPLC-DAD-ESI-MS chromatogram (at 257 and 320 nm) of a SPE (25% methanol) fraction of Moroccan Jujube (Ziziphus lotus) honey (10 g) II. 4-hydroxyquinoline, III. p-hydroxybenzoic acid, IV. caffeic acid, V. kynurenic acid.

Analytical HPLC-DAD-ESI-MS chromatogram (at 257 and 320 nm) of a SPE (100% methanol) fraction of Moroccan Jujube (Ziziphus lotus) honey (10 g) VI. methyl syringate.

Analytical HPLC-DAD-ESI-MS chromatogram (at 320 nm) of an Italian Chestnut (Castania sativa Mill.) honey (10 g) dissolved in doubly distilled water (50.0 mL) VII. 4-(1′-hydroxy-1′-dimethyl)cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside, VIII. 3-pyrrolinyl-kynurenic acid (3-PKA), IX. caffeic acid, X. p-coumaric acid, XI. 4-(1′-hydroxy-1′-dimethyl)cyclohexa-1,3-diene-1 carboxylic acid-1, XII. kynurenic acid tautomer, XIII. gamma-lact-3-PKA, XIV. kynurenic acid.

Structures of the phenolic compounds detected and identified in Moroccan Jujube (Ziziphus lotus) honeys I. 4-hydroxyquinoline glucoside, II. 4-hydroxyquinoline, III. p-hydroxybenzoic acid, IV. caffeic acid, V. kynurenic acid, VI. methyl syringate.

Structures of the major polyphenolic compounds identified in Italien chestnut (Castania sativa Mill.) honey VII. 4-(1′-hydroxy-1′-dimethyl)cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside, VIII. 3-pyrrolinyl-kynurenic acid (3-PKA), IX. caffeic acid, X. p-coumaric acid, XI. 4-(1′-hydroxy-1′-dimethyl)cyclohexa-1,3-diene-1 carboxylic acid-1, XII. kynurenic acid tautomer, XIII. gamma-lact-3-PKA, XIV. kynurenic acid.

GC-EI-MS of aglycone polyphenolic and alkaloid compound TMS-derivatives detected in Jujube (Ziziphus lotus) honey

No	Polyphenolic compound	R_t (min.)	M⁺calc.	Major neutral fragments (m/z %)
II	4-Hydroxyquinoline	16.38	217	73(29), 101(13), 172(18), 202(100), 217(49)
III	p-Hydroxybenzoic acid	16.51	282	73(74), 193(56), 223(71), 267(100), 282(28)
IV	trans-Caffeic acid	29.30	396	73(100),191(14), 219(7), 307(11), 381(24), 396(99)
V	Kynurenic acid	27.67	333	73(85), 231(81), 288(21), 304(34), 318(100), 333(10)
VI	Methyl syringate	21.30	284	73(26), 223(24), 254(100), 269(46), 284(31)

HPLC-ESI-MS data in negative ion mode at a fragmentor voltage (100 V) of polyphenolic, alkaloid and terpenoid compounds detected in Jujube and Chestnut honey extracts

Number	Phenolic compound	Molecular formula	R_t (min)	Molecular weight (exact)	[M-H]⁻	[2M-H]⁻
Jujube honeys (Morocco)^*

I	4-Hydroxyquinoline glucoside	C₁₅H₁₇NO₆	11.97	307.106	306.2	613.1
II	4-Hydroxyquinoline	C₉H₇NO	17.45	145.053	144.2	289.1
III	p-Hydroxybenzoic acid	C₇H₆O₃	19.82	138.032	137.2	275.2
IV	Caffeic acid	C₉H₈O₄	22.11	180.042	179.1	359.1
V	Kynurenic acid	C₁₀H₇NO₃	26.03	189.043	188.1	377.1
VI	Methyl syringate	C₁₀H₁₂O₅	35.69	212.068	211.1	423.0

Chestnut honey (Italy)^#

VII	4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside	C₂₂H₃₄O₁₃	15.18	505.199	505.2	1011.4
VIII	3-PKA	C₁₄H₁₄N₂O₃	16.28	258.100	257.1	n.d.
IX	Caffeic acid	C₉H₈O₄	17.99	180.042	179.1	359.1
X	p-Coumaric acid	C₉H₈O₃	21.48	164.047	163.1	327.1
XI	4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid	C₁₀H₁₄O₃	22.31	182.094	181.2	363.1
XII	Kynurenic acid tautomer	C₁₀H₇NO₃	22.54	189.042	188.1	377.1
XIII	Gamma-Lact-3-PKA	C₁₄H₁₂N₂O₂	24.32	240.089	239.1	n.d.
XIV	Kynurenic acid	C₁₀H₇NO₃	30.62	189.042	188.1	377.1

Major polyphenolic compounds, alkaloids and terpenoids detected in Jujube honeys and Chestnut honey (Italy)

Number	Phenolic compound	Jujube honey samples (mg/kg)

		H1	H2	H3	H4

Jujube honeys (Morocco)

I	4-Hydroxyquinoline glucoside	3.58±0.28	3.67±0.19	2.61±0.10	8.11±0.32
II	4-Hydroxyquinoline	3.38±0.37	3.38±0.09	3.38±0.18	16.29±0.86
III	p-Hydroxybenzoic acid	1.55±0.06	1.60±0.28	1.16±0.11	2.43±0
IV	Caffeic acid	1.41±0.13	1.18±0.04	0.77±0.07	3.44±0
V	Kynurenic acid	7.08±0.30	6.69±0.30	3.89±0.30	8.58±0.20
VI	Methyl syringate	12.24±0.18	12.98±0.92	4.83±0.12	3.31±0.09

	Total (mg/kg)	29.24±1.42	29.50±1.27	16.64±0.67	42.16±1.07

Chestnut honey (Italy)

Number	Phenolic compound				H5

					mg/kg

VII	4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside				305±4
VIII	3-PKA				187±3
IX	Caffeic acid				13±0.1
X	p-Coumaric acid				7±0.1
XI	4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid				179±11
XII	Kynurenic acid tautomer				94±2
XIII	Gamma-Lact-3-PKA				43±2
XIV	Kynurenic acid				1246±17

Total terpenoids (mg/kg)					484
Total alkaloids (mg/kg)					1570
Total polyphenols (mg/kg)					20

Total (mg/kg)					2074

eISSN:: 2299-4831
Język:: Angielski

Częstotliwość wydawania:: 2 razy w roku
Dziedziny czasopisma:: Life Sciences, Zoology, other

Kanał RSS czasopisma

HPLC-ESI-MS and GC-EI-MS Identification and Quantitation of Polyphenolics and Alkaloids in Moroccan Jujube Honeys

Article Category: Original paper

Data publikacji: 18 gru 2020

Zakres stron: 287 - 299

Otrzymano: 06 lut 2020

Przyjęty: 14 wrz 2020

DOI: https://doi.org/10.2478/jas-2020-0029

Słowa kluczowe
4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside, 4-hydroxyquinoline glucoside, 4-hydroxyquinoline, Jujube honey, kynurenic acid, methyl syringate, phenolic acid

© 2020 Farid Khallouki et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Fig. 1

Fig. 2

Fig. 3

Fig. 4

Fig. 5

Fig. 6

Fig. 7

GC-EI-MS of aglycone polyphenolic and alkaloid compound TMS-derivatives detected in Jujube (Ziziphus lotus) honey

HPLC-ESI-MS data in negative ion mode at a fragmentor voltage (100 V) of polyphenolic, alkaloid and terpenoid compounds detected in Jujube and Chestnut honey extracts

Major polyphenolic compounds, alkaloids and terpenoids detected in Jujube honeys and Chestnut honey (Italy)

HPLC-ESI-MS and GC-EI-MS Identification and Quantitation of Polyphenolics and Alkaloids in Moroccan Jujube Honeys

Article Category: Original paper

Data publikacji: 18 gru 2020

Zakres stron: 287 - 299

Otrzymano: 06 lut 2020

Przyjęty: 14 wrz 2020

DOI: https://doi.org/10.2478/jas-2020-0029

Słowa kluczowe4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside, 4-hydroxyquinoline glucoside, 4-hydroxyquinoline, Jujube honey, kynurenic acid, methyl syringate, phenolic acid

© 2020 Farid Khallouki et al., published by Sciendo

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Fig. 1

Fig. 2

Fig. 3

Fig. 4

Fig. 5

Fig. 6

Fig. 7

GC-EI-MS of aglycone polyphenolic and alkaloid compound TMS-derivatives detected in Jujube (Ziziphus lotus) honey

HPLC-ESI-MS data in negative ion mode at a fragmentor voltage (100 V) of polyphenolic, alkaloid and terpenoid compounds detected in Jujube and Chestnut honey extracts

Major polyphenolic compounds, alkaloids and terpenoids detected in Jujube honeys and Chestnut honey (Italy)

Słowa kluczowe
4-(1′-Hydroxy-1′-dimethyl) cyclohexa-1,3-diene-1 carboxylic acid-1-gentobioside, 4-hydroxyquinoline glucoside, 4-hydroxyquinoline, Jujube honey, kynurenic acid, methyl syringate, phenolic acid