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Proceeding Paper

Characterisation and Quantification of Phenolic Compounds in Honeys from Sierra Nevada (Granada) †

by
Marta Palma-Morales
1,2,*,
Alessandro Balzani
3,
Jesús R. Huertas
2,4,5,
Laura Mercolini
3 and
Celia Rodríguez-Pérez
1,2,6
1
Department of Nutrition and Food Science, Faculty of Pharmacy, University of Granada, Cartuja Campus, 18011 Granada, Spain
2
Biomedical Research Centre, Institute of Nutrition and Food Technology (INYTA) ‘José Mataix’, University of Granada, Avda. del Conocimiento s/n, 18071 Granada, Spain
3
Research Group of Pharmaco-Toxicological Analysis (PTA Lab), Department of Pharmacy and Biotechnology (FaBiT), Alma Mater Studiorum–University of Bologna, Via Belmeloro 6, 40126 Bologna, Italy
4
Department of Physiology, Pharmacy Faculty, Campus de Cartuja s/n, University of Granada, 18071 Granada, Spain
5
Primary Care Promotion of Maternal, Child and Women’s Health for Prevention of Adult Chronic Diseases Network (RD21/0012/0008), Institute of Health Carlos III, 28029 Madrid, Spain
6
Instituto de Investigación Biosanitaria ibs.GRANADA, 18012 Granada, Spain
*
Author to whom correspondence should be addressed.
†
Presented at the 4th International Electronic Conference on Foods, 15–30 October 2023; Available online: https://foods2023.sciforum.net/.
Biol. Life Sci. Forum 2023, 26(1), 74; https://doi.org/10.3390/Foods2023-15513
Published: 31 October 2023
(This article belongs to the Proceedings of The 4th International Electronic Conference on Foods)
Browse Figure
Versions Notes

Abstract

:
Some of the properties that have been attributed to honey are antioxidant, anti-inflammatory, and antimicrobial effects, especially due to its content of bioactive compounds, mainly phenolic compounds (PCs), whose content varies greatly depending on the variety, origin, agronomic conditions, harvest season, and climate. The aim of the present study is to characterise 21 honeys from Sierra Nevada (Granada). High-performance liquid chromatography coupled to quadrupole-time of flight mass spectrometry (HPLC-ESI-QTOF-MS) was used. Mass accuracy and true isotopic patterns in both MS and MS/MS spectra enabled the tentative identification of 58 PCs, including flavonoids, phenolic acids and derivatives. The average content of PCs was 83.01 ± 16.36 µg/g, with flavonoids accounting for more than 85%. The most abundant compounds were naringenin (16.88 ± 3.15 µg/g), pinocembrin (12.33 ± 2.92 µg/g), chrysin (12.21 ± 2.09 µg/g), carnosol (9.52 ± 2.90 µg/g), galangin (5.41 ± 1.68 µg/g), and apigenin (5.24 ± 0.89 µg/g). Due to this interesting composition, more studies are necessary to determine if the extreme environmental conditions of Sierra Nevada cause abiotic stress in the plants located there, fostering this concentration of PCs.

1. Introduction

Honey, a natural product crafted by honeybees (Apis mellifera), is renowned for its nutritive and healthful qualities. Its composition exhibits considerable variability based on factors like botanical and geographical origin [1,2]. Honey primarily consists of sugars (constituting 80–85% of its composition), water (15–17%), and proteins (0.1–0.4%). Additionally, to a lesser extent, it contains enzymes, organic acids, vitamins, minerals, and phenolic compounds, all of which significantly contribute to its sensory and functional attributes [3]. Honey has been associated with various beneficial effects, including antioxidant, anti-inflammatory, and antimicrobial properties [4]. These health-promoting properties are particularly linked to its content of bioactive compounds, mainly phenolic compounds (PCs). PC content varies substantially depending on factors such as honey variety, origin, agronomic conditions, harvest season, and climate. Plants synthetise PCs under both normal and stressful conditions, with functions that encompass attracting pollinating insects and safeguarding against pathogens and ultraviolet (UV) radiation [4]. Recent studies have reported a wide range of total phenolic content (TPC) values in honey, spanning from 6.5 ± 4.2 to 841.7 ± 304.0 µg/g [5]. While many researchers have analysed the content of bioactive compounds in some Spanish honeys, there are no previous studies on the content of those compounds in honeys from Sierra Nevada (Granada), where plants are exposed to extreme environmental conditions such as UV radiation, extreme temperatures, and altitude (hypoxia), which could influence the content of PCs. Thus, the aim of the present study is to characterise and quantify PCs in 21 honeys from Sierra Nevada, which is a national park with a great variety of vegetation exposed to abiotic stresses that could increase the concentration and/or variety of PCs contained in the honeys produced there.

2. Methodology

2.1. Extraction of Phenolic Compounds

The extraction of PCs was performed using a previously described method [6,7] with some modifications. Sixty grams of each of the selected honeys was mixed with 150 mL of acidified water (pH 2.0). The mixture was stirred for 10 min at room temperature on a magnetic stirrer and then filtered through cotton wool to remove solid particles. The filtrate was mixed with 40 g Amberlite XAD-2 and stirred for 10 min at room temperature on a magnetic stirrer. The Amberlite particles were packed in a 33 cm long, 24 mm inner diameter gravimetric column (Sigma-Aldrich). Then, the column was washed with 100 mL of acidic water (pH 2.0) and then with 300 mL of milliQ water. In this way, PCs present in the honey were retained in the column while sugars and other polar compounds were eluted with the aqueous solvent. To collect the phenolic fraction, 300 mL of methanol was used. Then, the phenolic fraction was dried in a rotary evaporator at a temperature of 30 °C. The residue was dissolved in 5 mL of milliQ water and extracted in triplicate with diethyl ether (5 mL × 3). The ether extracts were combined and the ether was removed with a rotary evaporator. The residue was dissolved in 1 mL of methanol, filtered through a 45μm membrane filter, transferred to an HPLC vial, and frozen at −20 °C until analysis.

2.2. Analysis of Phenolic Compounds

The analytical technique used was high-performance liquid chromatography coupled to mass spectrometry (HPLC-MS-MS/MS). Specifically, an Acquity HPLC system (Waters Corporation, Milford, MA, USA) coupled to an electrospray ionisation (ESI) source operating in negative mode and a quadrupole time-of-flight (QTOF) mass spectrometer (Waters) was used. To separate the compounds of interest effectively, an ACQUITY UPLC BEH Shield RP18 column (1.7 μm, 2.1 × 100 mm; Waters Corporation, Milford, MA, USA) was used. Acidified H2O with 1% acetic acid and methanol as solvents A and B, respectively, were used for the mobile phases. A linear gradient was applied so that at the start, 95% of the mixture was solvent A and 5% was solvent B; at minute 30, 23.9% was solvent A and 76.1% solvent B; and at minute 33, 100% was solvent B. The initial conditions were maintained for 6 min before each analysis. Column temperature was maintained at 40 °C and the injection volume was 0.5 mL/min.

2.3. Characterisation of Phenolic Compounds

MassLynx 4.1 software (Waters Corporation, Milford, MA, USA) was used to process the chromatographic data. The characterisation strategy was based on the exact mass and fragment information provided by the compound-specific MS and MS/MS spectra determined by the QTOF mass analyser. For the acquisition of information on the chemical structure of the compounds, in addition to consulting previously published research, the following databases were used: SciFinder Scholar (http://scifinder.cas.org (accessed on 12 December 2023)), FoodDb (https://foodb.ca/ (accessed on 12 December 2023)), MassBank (http://massbank.jp (accessed on 12 December 2023)), Pubchem (https://pubchem.ncbi.nlm.nih.gov (accessed on 12 December 2023)), Metfrag (https://msbi.ipb-halle.de/MetFrag/ (accessed on 12 December 2023)), METLIN (http://metlin.scripps.edu (accessed on 12 December 2023)), National Institute of Standards and Technology (https://www.nist.gov/ (accessed on 12 December 2023)), and the National Institute of Health (NIH) database. Additionally, SIRIUS 4 (https://bio.informatik.uni-jena.de/sirius/ (accessed on 12 December 2023)) was used to obtain metabolite structure information. Six analytical standards (catechin, chlorogenic acid, ferulic acid, rutin, phloridizin, quercetin, phloretin, and vanillic acid) were employed to estimate the amount of phenolic compounds present in the honeys.

3. Results and Discussion

Fifty-eight phenolic compounds were characterized in the 21 honeys, including flavonoids, phenolic acids, and derivatives (Table 1).
The average TPC of the Sierra Nevada honeys analysed was 83.01 ± 16.36 µg/g, being above the average of other Spanish honeys such as Galician honeys, which contain an average of 38 µg/g [8]. Flavonoids accounted for more than 85% of the TPC. Figure 1 shows the content of phenolic acids, flavonoids, other phenolic compounds, and total phenolic compounds in each honey. The most abundant compounds were naringenin (16.88 ± 3.15 µg/g), pinocembrin (12.33 ± 2.92 µg/g), chrysin (12.21 ± 2.09 µg/g), carnosol (9.52 ± 2.90 µg/g), galangin (5.41 ± 1.68 µg/g), and apigenin (5.24 ± 0.89 µg/g). Naringenin is noted for its positive effects on the cardiovascular system through antioxidant, anti-inflammatory, antiatherogenic, and antiapoptotic actions [9]. Pinocembrin is a flavanone with antioxidant, antimicrobial, and anti-inflammatory properties, and has recently been studied for its potential to inhibit histidine decarboxylase as a new natural antiallergic drug candidate [10]. Chrysin has shown significantly greater antiproliferative activity on cancer cell growth than other compounds [11]. It also has antioxidant, antiobesity, anti-inflammatory, antidiabetic, and neuroprotective activity [12]. Carnosol is a phenolic diterpene with demonstrated antioxidant, anti-inflammatory, and anticancer activity [13,14]. Positive effects of carnosol have also been reported in ischaemic stroke by inhibiting apoptosis and attenuating oxidative damage and cellular inflammation [15]. The main positive effects of galangin are attributed to its anti-inflammatory, antioxidant, anticancer, and antineoplastic properties [16]. Apigenin has shown therapeutic functions through cell cycle arrest, apoptosis, and anti-inflammatory effects. In addition, apigenin contributes to counteracting oxidative stress by enhancing the expression of antioxidant enzymes such as glutathione synthase, catalase, and superoxide dismutase. After its absorption into the digestive tract, apigenin is able to reach the brain and could have antidepressant and antianxiety effects [17].
Table 1. Phenolic compounds characterised in the 21 honeys.
Table 1. Phenolic compounds characterised in the 21 honeys.
[M-H]−RTMolecular FormulaProposed CompoundFragmentsReference
135.04332.189C8H8O2Phenylacetic acid117[18]
135.04382.01C8H8O2Vinylcatechol134, 133, 105[19]
137.02224.014C7H6O3Hydroxybenzoic acid93[20]
153.02084.852C7H6O4Protocatechuic acid109, 137[21]
163.03863.225C9H8O3Cumaric acid (Isomer 1)145, 119[20]
163.03963.341C9H8O3Cumaric acid (Isomer 2)119, 117[20]
165.05472.458C9H10O34-hydroxicinnamic acid161, 133, 132, 122[22]
165.05583.448C9H10O3L-(-)-phenylactic acid147[23]
167.03372.065C8H8O4Homogentisic acid134, 137, 131, 117, 108[24]
177.01811.769C9H6O4Esculatin145, 125, 120, 144[25]
193.04952.095C10H10O4Coniferic/ferulic acid133[26]
195.06591.995C10H12O44-methoxyphenylactic acid133, 177, 149[27]
197.04422.16C9H10O5Siringic acid (Isomer 1)106[20]
197.04552.262C9H10O5Siringic acid (Isomer 2)121, 123[20]
211.05994.875C10H12O5Methylsyringate181[28]
221.08043.45C12H14O43-hydroxy-1-(2-methoxyphenyl)penta-1,4-dione (Isomer 1)133[29]
221.08113.605C12H14O43-hydroxy-1-(2-methoxyphenyl)penta-1,4-dione (Isomer 2)133[29]
223.06093.228C11H12O5Sinapic acid144, 116, 142, 160[21]
223.09686.851C12H16O4Vanillin 1,2-butylene glycol151, 136, 108[30]
253.049712.928C15H10O4Chrysin209, 143, 145, 119,195[31]
255.065912.128C15H12O4Pinocembrin171, 133, 213, 134, 169[32]
269.043910.498C15H10O5Apigenin117,149, 201, 145, 183, 107[33]
269.04419.803C15H10O5Baicalein129, 143, 151[25]
269.044513.681C15H10O5Galangin211, 239, 195,167, 151[34]
271.06007.979C15H12O5Pinobanksin253, 197,225, 209, 125[35]
271.06038.406C15H12O5Naringenin253,197, 161,125, 225[20]
283.059711.218C16H12O5Prunetin211, 238, 167, 165[36]
283.060413.878C16H12O5Biochanin A268, 211, 239, 269, 195[37]
283.060513.469C16H12O5Genkwanin 134, 175, 168, 148, 159[38]
283.096913.161C17H16O4Phenylethyl caffeate135, 133, 161, 134[34]
285.038110.787C15H10O6Kaempferol (Isomer 1)151, 184, 245, 255, 273[39]
285.03926.831C15H10O6Luteolin (Isomer 1)151, 257[40]
285.039413.682C15H10O6Kaempferol (Isomer 2)269, 268, 211, 239[39]
285.03968.691C15H10O6Luteolin (Isomer 2)255, 133, 283, 151[40]
285.04047.646C15H10O6Kaempferol (Isomer 3)255, 227, 211, 284[39]
285.04089.135C15H10O6Luteolin (Isomer 3)241, 133[40]
285.077212.291C16H14O55-O-Methylnaringenin188, 191, 255, 243, 158[20]
287.05555.52C15H12O6Eriodictyol161, 269, 251[41]
299.054511.479C16H12O6Kaempferide (Isomer 1)284, 227, 256, 165, 269[42]
299.054711.155C16H12O6Kaempferide (Isomer 2)284[42]
301.03224.236C15H10O7Quercetin175, 183, 201, 225, 245[42]
301.03394.077C15H10O7Quercetin255, 273, 213, 151[42]
301.03549.343C15H10O7Morin273, 151, 257, 178, 255[34]
301.06969.9400C16H14O6Hesperetin (Isomer 1)164[43]
301.07135.3190C16H14O6Hesperetin (Isomer 2)151, 177[43]
301.07175.4440C16H14O6Hesperetin (Isomer 3)177, 286[43]
301.20088.5460C15H10O7Tricetin 255, 151[44]
315.048710.875C16H12O73-Methylquercetin/Isorhamnetin (Isomer 1)241, 242, 270, 313, 300[39]
315.050010.157C16H12O73-Methylquercetin/Isorhamnetin (Isomer 2)300[39]
315.05069.136C16H12O73-Methylquercetin/Isorhamnetin (Isomer 3)241, 242, 270, 271, 300, 313[39]
329.06509.824C17H14O7Quercetin dimethyl ether (Isomer 1)314[45]
329.066411.956C17H14O7Quercetin dimethyl ether (Isomer 2)314[45]
329.174415.415C20H26O4Carnosol (Isomer 1)285[35]
329.174515.068C20H26O4Carnosol (Isomer 2)285[35]
329.175315.708C20H26O4Carnosol (Isomer 3)285[35]
329.175814.856C20H26O4Carnosol (Isomer 4)285[35]
431.09747.651C21H20O10Kaempferol-rharmnoside285, 255, 227[46]
461.10659.049C22H22O118-Methoxykaempferol 7-rhamnopyranoside287, 299, 315, 259, 139[46]
RT: retention time.

4. Conclusions

Due to the interesting composition of Sierra Nevada honeys, more studies are necessary to determine if the peculiar environmental conditions of Sierra Nevada, such as UV radiation, extreme temperature, or altitude (hypoxia), cause abiotic stress in the plants located there, fostering an elevated concentration of PCs and thus increasing the antioxidant, antimicrobial, anti-inflammatory, and anticarcinogenic activity of these honeys.

Author Contributions

Conceptualization, C.R.-P.; investigation, M.P.-M. and A.B.; data curation, M.P.-M. and C.R.-P.; writing—original draft preparation, M.P.-M.; writing—review and editing, M.P.-M., A.B., J.R.H., L.M. and C.R.-P.; supervision, C.R.-P.; funding acquisition, J.R.H. All authors have read and agreed to the published version of the manuscript.

Funding

Contract for young research personnel financed by the Programa Operativo de Empleo Juvenil (Youth Employment Program) Ref: 8017, and contract to the Junta de Andalucía-Consejería de Universidad, Investigación e Innovación Research Project: P21_00777 M.P.-M.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Data that support the findings of this study are available from the corresponding author, M.P.-M., upon reasonable request.

Acknowledgments

NUTRACMIEL research project (CDTI-FEDER 4162-00).

Conflicts of Interest

The authors declare no conflict of interest.

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Blsf 26 00074 g001
Figure 1. Content of phenolic compounds of Sierra Nevada honeys.
Figure 1. Content of phenolic compounds of Sierra Nevada honeys.
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MDPI and ACS Style

Palma-Morales, M.; Balzani, A.; Huertas, J.R.; Mercolini, L.; Rodríguez-Pérez, C. Characterisation and Quantification of Phenolic Compounds in Honeys from Sierra Nevada (Granada). Biol. Life Sci. Forum 2023, 26, 74. https://doi.org/10.3390/Foods2023-15513

AMA Style

Palma-Morales M, Balzani A, Huertas JR, Mercolini L, Rodríguez-Pérez C. Characterisation and Quantification of Phenolic Compounds in Honeys from Sierra Nevada (Granada). Biology and Life Sciences Forum. 2023; 26(1):74. https://doi.org/10.3390/Foods2023-15513

Chicago/Turabian Style

Palma-Morales, Marta, Alessandro Balzani, Jesús R. Huertas, Laura Mercolini, and Celia Rodríguez-Pérez. 2023. "Characterisation and Quantification of Phenolic Compounds in Honeys from Sierra Nevada (Granada)" Biology and Life Sciences Forum 26, no. 1: 74. https://doi.org/10.3390/Foods2023-15513

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