Characterisation of Some Phytochemicals Extracted from Black Elder (Sambucus nigra L.) Flowers Subjected to Ozone Treatment
Abstract
:1. Introduction
2. Results and Discussion
2.1. Antioxidant Activity of the Syrups
2.2. Content of Vitamin C in Syrups
2.3. Total Contents of Polyphenols in Syrups
2.4. Determination of Polyphenolic Compounds
2.5. Colour
2.6. Profile of Volatile Compounds
3. Materials and Methods
3.1. Plant Materials
3.2. The Ozone Treatment of the Plant Material
3.3. Production of Syrups from Flowers of Black Elder
3.4. Determination of Antioxidant Activity
3.5. Determination of Ascorbic Acid Content
3.6. Total Phenolic Content Assay
3.7. Polyphenolic Compounds Analysis
3.7.1. Sample Preparation
3.7.2. Determination of Polyphenols Profile
3.8. Head Space–Solid Phase Microextraction HS–SPME of Prepared Syrup
3.9. Chromatographic Analysis
3.10. Colour Change
3.11. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
- Petruţ, G.S.; Muste, S.; Mureșan, C.; Păucean, A.; Mureşan, A.E.; Nagy, M. Chemical Profiles and Antioxidant Activity of Black Elder (Sambucus nigra L.)—A Review. Bull. UASVM Food Sci. Technol. 2017, 74, 9–16. [Google Scholar] [CrossRef] [Green Version]
- Charlebois, D.; Byers, P.L.; Finn, C.E.; Thomas, A.L. Elderberry: Botany, horticulture, potential. Hortic. Rev. 2010, 37, 213–280. [Google Scholar]
- Mikulic-Petkovsek, M.; Ivancic, A.; Schmitzer, V.; Veberic, R.; Stampar, F. Comparison of major taste compounds and antioxidative properties of fruits and flowers of different Sambucus species and interspecific hybrids. Food Chem. 2016, 200, 134–140. [Google Scholar] [CrossRef] [PubMed]
- Olejnik, A.; Olkowicz, M.; Kowalska, K.; Rychlik, J.; Dembczyński, R.; Myszka, K.; Juzwa, W.; Białas, W.; Moyer, M.P. Gastrointestinal digested Sambucus nigra L. fruit extract protects in vitro cultured human colon cells against oxidative stress. Food Chem. 2016, 197, 648–657. [Google Scholar] [CrossRef]
- Vlachojannis, C.; Zimmermann, B.F.; Chrubasik-Hausmann, S. Quantification of anthocyanins in elderberry and chokeberry dietary supplements. Phytother. Res. 2015, 29, 561–565. [Google Scholar] [CrossRef]
- Ivanišová, E.; Kačániová, M.; Frančáková, H.; Petrová, J.; Hutková, J.; Brovarskyi, V.; Velychko, S.; Adamchuk, L.; Schubertová, Z.; Musilová, J. Bee bread—Perspective source of bioactive compounds for future. Potravin. Slovak J. Food Sci. 2015, 9, 592–598. [Google Scholar] [CrossRef] [Green Version]
- Tomášková, L.; Sochor, J.; Baroň, M. The study of antioxidants in grapevine seeds. Potravin. Slovak J. Food Sci. 2017, 11, 132–137. [Google Scholar] [CrossRef] [Green Version]
- Cavero, R.Y.; Akerreta, S.; Calvo, M.I. Medicinal plants used for dermatological affections in Navarra and their pharmacological validation. J. Ethnopharmacol. 2013, 149, 533–542. [Google Scholar] [CrossRef]
- Folmer, F.; Basavaraju, U.; Jaspars, M.; Hold, G.; El-Omar, E.; Dicato, M.; Diederich, M. Anticancer effects of bioactive berry compounds. Phytochem. Rev. 2014, 13, 295–322. [Google Scholar] [CrossRef]
- Kaack, K.; Christensen, L.; Hughes, M.; Eder, R. Relationship between sensory quality and volatile compounds of elderflower (Sambucus nigra L.) extracts. Eur. Food Res. Technol. 2006, 223, 57–70. [Google Scholar] [CrossRef]
- Willer, B. Untersuchungen zur Antiasthmatischen Wirkung von Sambucus nigra. Ph.D. Thesis, University of Regensburg, Regensburg, Germany, 1997. [Google Scholar]
- Senica, M.; Stampar, F.; Veberic, R.; Mikulic-Petkovsek, M. Processed elderberry (Sambucus nigra L.) products: A beneficial or harmful food alternative? LWT J. Food Sci. Technol. 2016, 72, 182–188. [Google Scholar] [CrossRef]
- Newall, C.A.; Anderson, L.A.; Phillipson, J.D. Herbal Medicines, a Guide for Healthcare Professionals; Pharmaceutical Press: London, UK, 1996. [Google Scholar]
- Blumenthal, M.; Goldberg, A.; Brinckmann, J. Herbal Medicine: Expanded Commission E Monographs; Integrative Medicine Communications: Newton, MA, USA, 2000; pp. 78–83. [Google Scholar]
- Fleming, T. PDR for Herbal Medicines, 2nd ed.; Medical Economics Company: Montvale, NJ, USA; North Olmsted, OH, USA, 2000. [Google Scholar]
- Senica, M.; Stampar, F.; Vebericm, R.; Mikulic-Petkovsek, M. The higher the better? Differences in phenolics and cyanogenic glycosides in Sambucus nigra leaves, flowers and berries from different altitudes. J. Sci. Food Agric. 2016, 97, 2623–2632. [Google Scholar] [CrossRef]
- Available online: https://www.ema.europa.eu/en/documents/herbal-report/draft-assessment-report-sambucus-nigra-l-fructus_en.pdf (accessed on 1 August 2021).
- Available online: https://www.ema.europa.eu/en/documents/herbal-report/superseded-assessment-report-development-community-monographs-inclusion-herbal-substances_en.pdf (accessed on 1 August 2021).
- Bratu, M.M.; Doroftei, E.; Negreanu-Pirjol, T.; Hostina, C.; Porta, S. Determination of Antioxidant Activity and Toxicity of Sambucus nigra Fruit Extract Using Alternative Methods. Food Technol. Biotechnol. 2012, 50, 177–182. [Google Scholar]
- Pabi, N.; Innerhofer, G.; Leitner, E.; Siegmund, B. The Flavor of Elderflower—Species Differentiation via Flavor Compounds. In Flavour Science; Academic Press: Cambridge, MA, USA, 2014; Volume 17, pp. 95–99. [Google Scholar] [CrossRef]
- Agalar, D.; Demirci, B.; Demirci, F.; Kirimer, N. The Volatile Compounds of the Elderflowers Extract and the Essential Oil. Rec. Nat. Prod. 2017, 11, 491–496. [Google Scholar] [CrossRef]
- Christensen, K.; Olsen, L.; Kotowska, D.; Bhattacharya, S.; Fretté, X.C.; Færgeman, N.; Kristiansen, K.; Oksbjerg, N.; Christensen, L. Elderflowers (Sambucus nigra L.) have a significant impact on cellular mechanisms related to lipid storage and insulin resistance. Planta Med. 2010, 76, P633. [Google Scholar] [CrossRef]
- Schmitzer, V.; Veberic, R.; Slatnar, A.; Stampar, F. Elderberry (Sambucus nigra L.) wine: A product rich in health promoting compounds. J. Agric. Food Chem. 2010, 58, 10143–10146. [Google Scholar] [CrossRef] [PubMed]
- Hubbermann, E.M.; Heins, A.; Stoeckmann, H.; Schwarz, K. Influence of acids, salt, sugars and hydrocolloids on the colour stability of anthocyanin rich black currant and elderberry concentrates. Eur. Food Res. Technol. 2006, 223, 83–90. [Google Scholar] [CrossRef]
- da Silva, R.F.R.; Barreira, J.C.M.; Heleno, S.A.; Barros, L.; Calhelha, R.C.; Ferreira, I.C. Anthocyanin Profile of Elderberry Juice: A Natural-Based Bioactive Colouring Ingredient with Potential Food Application. Molecules 2019, 24, 2359. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Piechowiak, T.; Antos, P.; Kosowski, P.; Skrobacz, K.; Józefczyk, R.; Balawejder, M. Impact of ozonation process on the microbiological and antioxidant status of raspberries (Rubus ideaeus L.) during storage at room temperature. Agric. Food Sci. 2019, 28, 35–44. [Google Scholar] [CrossRef]
- Matlok, N.; Piechowiak, T.; Gorzelany, J.; Zardzewiały, M.; Balawejder, M. Effect of Ozone Fumigation on Physiological Processes and Bioactive Compounds of Red-Veined Sorrel (Rumex sanguineus ssp. sanguineus). Agronomy 2020, 10, 1726. [Google Scholar] [CrossRef]
- Gorzelany, J.; Migut, D.; Matłok, N.; Balawejder, M.; Kačániová, M. Impact of Pre-Ozonation on Mechanical Properties of Selected Genotypes of Cucumber Fruits During the Souring Process. Ozone Sci. Eng. 2016, 39, 188–195. [Google Scholar] [CrossRef]
- Dubois, M.; Canadas, D.; Despres-Pernot, A.G. Oxygreen process applied on nongerminated and germinated wheat: Role of hydroxamic acids. J. Agric. Food Chem. 2008, 56, 1116–1121. [Google Scholar] [CrossRef] [PubMed]
- Zardzewiały, M.; Matlok, N.; Piechowiak, T.; Gorzelany, J.; Balawejder, M. Ozone Treatment as a Process of Quality Improvement Method of Rhubarb (Rheum rhaponticum L.) Petioles during Storage. Appl. Sci. 2020, 10, 8282. [Google Scholar] [CrossRef]
- Matłok, N.; Gorzelany, J.; Piechowiak, T.; Antos, P.; Zardzewiały, M.; Balawejder, M. Impact of Ozonation Process on the Content of Bioactive Compounds with Antioxidant Properties in Scots Pine L. Shoots as Well as Yield and Composition of Essential Oils. Acta Univ. Cibiniensis Ser. E Food Technol. 2020, 24, 146–155. [Google Scholar] [CrossRef]
- Buhrmester, R.A.; Ebinger, J.E.; Seigler, D.S. Sambunigrin and cyanogenic variability in populations of Sambucus canadensis L. (Caprifoliaceae). Biochem. Syst. Ecol. 2000, 28, 689–695. [Google Scholar] [CrossRef]
- Onyebuchi, C.; Kavaz, D. Effect of extraction temperature and solvent type on the bioactive potential of Ocimum gratissimum L. extracts. Sci. Rep. 2020, 10, 21760. [Google Scholar] [CrossRef]
- Piechowiak, T.; Balawejder, M. Impact of ozonation process on the level of selected oxidative stress markers in raspberries stored at room temperature. Food Chem. 2019, 298, 125093. [Google Scholar] [CrossRef]
- Matłok, N.; Piechowiak, T.; Zardzewiały, M.; Gorzelany, J.; Balawejder, M. Effects of Ozone Treatment on Microbial Status and the Contents of Selected Bioactive Compounds in Origanum majorana L. Plants. Plants 2020, 9, 1637. [Google Scholar] [CrossRef]
- Piechowiak, T.; Antos, P.; Józefczyk, R.; Kosowski, P.; Skrobacz, K.; Balawejder, M. Impact of Ozonation Process on the Microbiological Contamination and Antioxidant Capacity of Highbush Blueberry (Vaccinum corymbosum L.) Fruit during Cold Storage. Ozone Sci. Eng. 2018, 41, 376–385. [Google Scholar] [CrossRef]
- Zapałowska, A.; Matłok, N.; Zardzewiały, M.; Piechowiak, T.; Balawejder, M. Effect of Ozone Treatment on the Quality of Sea Buckthorn (Hippophae rhamnoides L.). Plants 2021, 10, 847. [Google Scholar] [CrossRef]
- Harbourne, N.; Jacquier, J.C.; O’Riordan, D. Optimision of the Extraction and Processing Conditions of Chamomile (Matricaria chamomilla L.) for Incorporation into a Beverage. Food Chem. 2009, 115, 15–19. [Google Scholar] [CrossRef]
- Chen, C.; Zhang, H.; Dong, C.; Ji, H.; Zhang, X.; Li, L.; Ban, Z.; Zhang, N.; Xue, W. Effect of ozone treatment on the phenylpropanoid biosynthesis of postharvest strawberries. RSC Adv. 2019, 44, 25429–25438. [Google Scholar] [CrossRef] [Green Version]
- Piechowiak, T.; Grzelak-Błaszczyk, K.; Bonikowski, R.; Balawejder, M. Optimization of antioxidant compounds from yellow onion skin and their use in functional bread production. LWT 2020, 117, 108614. [Google Scholar] [CrossRef]
- Thiyagarajan, K.; Vitali, F.; Tolaini, V.; Galeffi, P.; Cantale, C.; Vikram, P.; Singh, S.; De Rossi, P.; Nobili, C.; Procacci, S.; et al. Genomic Characterization of Phenylalanine Ammonia Lyase Gene in Buckwheat. PLoS ONE 2016, 11, e0151187. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Sachadyn-Król, M.; Agriopoulou, S. Ozonation as a Method of Abiotic Elicitation Improving the Health-Promoting Properties of Plant Products—A Review. Molecules 2020, 25, 2416. [Google Scholar] [CrossRef]
- Kramp, F.; Paulson, S.E. The gas phase reaction of ozone with 1,3-butadiene: Formation yields of some toxic products. Atmos. Environ. 2000, 34, 35–43. [Google Scholar] [CrossRef]
- Etschmann, M.M.W.; Bormann, S.; Schrader, J. Chapter 38—Microbial Conversion of (±)Linalool to Linalool Oxides by Corynespora cassiicola. In Flavour Science; Academic Press: Cambridge, MA, USA, 2014; pp. 201–204. [Google Scholar] [CrossRef]
- Porter, Y. Antioxidant properties of green broccoli and purple-sprouting broccoli under different cooking conditions. Biosci. Horiz. Int. J. Stud. Res. 2012, 5, hzs004. [Google Scholar] [CrossRef] [Green Version]
- Matłok, N.; Stępień, A.E.; Gorzelany, J.; Wojnarowska-Nowak, R.; Balawejder, M. Effects of Organic and Mineral Fertilization on Yield and Selected Quality Parameters for Dried Herbs of Two Varieties of Oregano (Origanum vulgare L.). Appl. Sci. 2020, 10, 5503. [Google Scholar] [CrossRef]
- Matłok, N.; Gorzelany, J.; Stepień, A.E.; Figiel, A.; Balawejder, M. Effect of fertilization in selected phytometric features and contents of bioactive compounds in dry matter of two varieties of Basil (Ocimum basilicum L.). Sustainability 2019, 11, 6590. [Google Scholar] [CrossRef] [Green Version]
Compound | Rt | λmax | (M − H) m/z | Content in Syrup (%) | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
min | nm | MS | MS/MS | 0 ppm | 10 ppm | 100 ppm | ||||||
0 min | 5 min | 15 min | 30 min | 5 min | 15 min | 30 min | ||||||
1 | Chlorogenic acid | 2.86 | 298 sh/328 | 353 | 191/179 | 0.70 ± 0.03 a | 1.08 ± 0.16 a | 3.45 ± 0.30 c | 3.60 ± 0.13 c | 1.40 ± 0.03 a | 2.16 ± 0.71 b | 2.77 ± 0.41 b |
2 | Unspecified hydroxybenzoic derivative | 3.09 | 264 | 393 | 163 | 0.68 ± 0.25 b | 0.74 ± 0.18 b | 1.07 ± 0.21 c | 1.67 ± 0.05 c | 1.06 ± 0.09 c | 1.30 ± 0.12 c | 0.14 ± 0.04 a |
3 | Naringenin 5,7-O-di-glucoside | 3.13 | 268/324 | 595 | 271 | 0.16 ± 0.01 a | 0.18 ± 0.02 a | 0.54 ± 0.53 b | 0.89 ± 0.06 c | 0.49 ± 0.03 b | 0.81 ± 0.01 c | 0.39 ± 0.04 b |
4 | Naringenin 7-O-rutinoside-5-O-pentoside | 3.24 | 271/317 | 711 | 403/271 | 0.27 ± 0.03 a | 0.25 ± 0.01 a | 0.73 ± 0.68 b | 0.69 ± 0.24 b | 0.99 ± 0.36 b | 1.01 ± 0.23 b | 0.70 ± 0.17 b |
5 | Kaempferol 3-O-di-glucoside | 3.30 | 262/317 | 609 | 285 | 0.17 ± 0.02 a | 0.25 ± 0.02 a | 0.45 ± 0.09 b | 0.57 ± 0.00 b | 0.43 ± 0.26 b | 0.51 ± 0.01 b | 0.13 ± 0.01 a |
6 | Quercetin 3-O-rutinoside-7-O-glucoside | 3.57 | 255/347 | 771 | 609/301 | 0.44 ± 0.16 b | 0.27 ± 0.08 a | 0.24 ± 0.15 a | 0.56 ± 0.00 b | 1.10 ± 0.57 d | 0.71 ± 0.06 c | 0.40 ± 0.11 b |
7 | Quercetin 3-O-di-glucoside | 3.77 | 255/352 | 625 | 301 | 4.87 ± 0.86 a | 4.56 ± 0.71 a | 4.08 ± 0.93 a | 4.98 ± 0.46 a | 6.22 ± 1.54 b | 6.91 ± 1.45 b | 4.96 ± 1.27 a |
8 | Quercetin 3-O-rutinoside-7-O-pentoside | 3.88 | 255/355 | 741 | 609/301 | 0.15 ± 0.02 b | 0.08 ± 0.01 a | 0.06 ± 0.01 a | 0.41 ± 0.11 c | 0.39 ± 0.20 c | 0.19 ± 0.05 b | 0.06 ± 0.01 a |
9 | Quercetin 3-O-rutinoside-7-O-rhamnoside | 3.99 | 255/345 | 755 | 609/301 | 1.15 ± 0.04 a | 1.22 ± 0.03 a | 1.33 ± 0.31 a | 1.07 ± 0.18 a | 1.20 ± 0.20 a | 1.08 ± 0.14 a | 1.15 ± 0.02 a |
10 | Quercetin 3-O-glucoside-pentoside | 4.05 | 255/345 | 595 | 301 | 2.64 ± 0.00 b | 2.40 ± 0.07 b | 2.49 ± 1.10 b | 2.18 ± 0.28 b | 2.03 ± 0.13 b | 1.45 ± 0.09 a | 1.58 ± 0.13 a |
11 | Kaempferol 3,7-O-di-glucoside | 4.22 | 264/339 | 609 | 447/285 | 0.68 ± 0.09 b | 0.67 ± 0.01 b | 0.67 ± 0.23 b | 0.86 ± 0.01 c | 0.79 ± 0.27 c | 0.59 ± 0.04 a | 0.41 ± 0.00 a |
12 | Quercetin 3-O-glucoside-7-O-glucuronide | 4.30 | 255/352 | 639 | 463/301 | 4.99 ± 0.78 b | 5.69 ± 0.98 b | 5.64 ± 2.00 b | 5.06 ± 0.41 b | 4.01 ± 0.54 a | 3.63 ± 1.01 a | 3.32 ± 0.72 a |
13 | Quercetin 3-O-rutinoside (Rutin) | 4.38 | 255/352 | 609 | 301 | 22.90 ± 0.53 a | 19.57 ± 1.3 a | 20.94 ± 0.37 a | 23.30 ± 0.43 a | 32.73 ± 1.20 b | 27.82 ± 2.01 b | 35.63 ± 1.42 b |
14 | Quercetin 3-O-glucoside | 4.61 | 255/355 | 463 | 301 | 8.21 ± 1.35 b | 6.93 ± 0.78 a | 6.72 ± 0.01 a | 7.17 ± 0.10 a | 9.41 ± 0.29 b | 11.31 ± 0.79 c | 9.04 ± 2.23 b |
15 | Quercetin 3-O-(6″-acetyl)-glucoside | 4.96 | 255/352 | 505 | 463/301 | 8.45 ± 0.20 d | 9.66 ± 1.46 d | 8.60 ± 0.06 d | 8.68 ± 0.31 d | 4.89 ± 0.23 b | 6.96 ± 0.36 c | 3.20 ± 0.52 a |
16 | 3,4-dicaffeoylquinic acid | 5.14 | 288 sh/328 | 515 | 353/191 | 18.54 ± 0.46 b | 19.75 ± 0.78 b | 21.29 ± 2.05 b | 16.12 ± 0.96 a | 17.48 ± 0.54 a | 15.55 ± 0.48 a | 18.98 ± 1.87 b |
17 | Quercetin 3-O-glucuronide | 5.32 | 255/348 | 477 | 301 | 13.45 ± 1.27 b | 15.22 ± 1.03 b | 10.11 ± 1.77 a | 12.36 ± 0.73 b | 8.10 ± 2.69 a | 9.90 ± 0.94 a | 9.55 ± 0.54 a |
18 | 1.5-di-caffeoyl-quinic acid | 5.48 | 288 sh/326 | 515 | 353/179 | 1.05 ± 0.18 b | 1.21 ± 0.27 b | 1.31 ± 0.11 b | 0.78 ± 0.02 a | 0.74 ± 0.35 a | 2.19 ± 0.01 c | 2.05 ± 0.06 c |
19 | Kaempferol 3-O-rhamnoside-7-O-pentoside | 5.66 | 264/345 | 563 | 431/285 | 3.82 ± 0.06 c | 5.30 ± 1.01 d | 5.38 ± 0.82 d | 4.11 ± 0.05 d | 2.15 ± 0.15 a | 2.53 ± 0.19 b | 1.86 ± 0.10 a |
20 | Unspecified caffeoyl-quinic derivative | 6.55 | 288 sh/322 | 538 | 341/191 | 1.16 ± 0.24 a | 1.42 ± 0.41 a | 1.54 ± 0.01 a | 1.88 ± 0.07 b | 1.23 ± 0.21 a | 1.41 ± 0.09 a | 1.56 ± 0.70 a |
21 | Quercetin | 6.62 | 255/355 | 301 | - | 3.47 ± 0.21 d | 2.09 ± 0.11 c | 1.96 ± 0.24 b | 1.91 ± 0.11 b | 1.79 ± 0.04 a | 1.47 ± 0.03 a | 1.56 ± 0.27 a |
22 | Naringenin | 7.53 | 271/317 | 271 | - | 0.85 ± 0.04 b | 1.31 ± 0.01 c | 1.18 ± 0.02 c | 0.87 ± 0.07 b | 1.11 ± 0.21 c | 0.36 ± 0.00 a | 0.35 ± 0.00 a |
23 | Quercetin 7-methyl ether | 7.98 | 255/355 | 315 | - | 1.22 ± 0.07 b | 0.16 ± 0.00 a | 0.20 ± 0.11 a | 0.29 ± 0.17 a | 0.25 ± 0.04 a | 0.17 ± 0.02 a | 0.21 ± 0.18 a |
Compound | Rt | λmax | (M − H) m/z | Content in Syrup (%) | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
min | nm | MS | MS/MS | 0 ppm | 10 ppm | 100 ppm | ||||||
0 min | 5 min | 15 min | 30 min | 5 min | 15 min | 30 min | ||||||
1 | Chlorogenic acid | 2.86 | 298 sh/328 | 353 | 191/179 | 5.43 ± 0.79 b | 4.35 ± 0.63 b | 3.77 ± 0.20 a | 3.70 ± 0.61 a | 5.58 ± 0.50 b | 3.14 ± 0.42 a | 2.97 ± 0.92 a |
2 | Unspecified hydroxybenzoic derivative | 3.09 | 264 | 393 | 163 | 0.99 ± 0.30 b | 0.69 ± 0.04 a | 0.73 ± 0.00 a | 0.80 ± 0.11 b | 0.87 ± 0.04 b | 0.65 ± 0.00 a | 0.80 ± 0.17 b |
3 | Naringenin 5,7-O-di-glucoside | 3.13 | 268/324 | 595 | 271 | 0.83 ± 0.15 b | 0.66 ± 0.10 a | 0.57 ± 0.06 a | 0.63 ± 0.07 a | 0.83 ± 0.30 b | 0.58 ± 0.05 a | 0.62 ± 0.31 a |
4 | Naringenin 7-O-rutinoside-5-O-pentoside | 3.24 | 271/317 | 711 | 403/271 | 0.38 ± 0.15 a | 0.61 ± 0.01 b | 0.78 ± 0.04 b | 0.70 ± 0.09 b | 1.31 ± 0.06 c | 0.80 ± 0.17 b | 0.76 ± 0.05 b |
5 | Kaempferol 3-O-di-glucoside | 3.30 | 262/317 | 609 | 285 | 0.14 ± 0.02 a | 0.26 ± 0.10 b | 0.42 ± 0.12 d | 0.39 ± 0.06 c | 0.41 ± 0.14 d | 0.20 ± 0.07 b | 0.33 ± 0.01 c |
6 | Quercetin 3-O-rutinoside-7-O-glucoside | 3.57 | 255/347 | 771 | 609/301 | 0.28 ± 0.04 a | 0.25 ± 0.05 a | 0.40 ± 0.04 b | 0.73 ± 0.45 c | 1.37 ± 0.57 d | 0.85 ± 0.14 c | 1.15 ± 0.05 d |
7 | Quercetin 3-O-di-glucoside | 3.77 | 255/352 | 625 | 301 | 3.21 ± 0.17 a | 3.98 ± 0.24 a | 4.45 ± 0.32 b | 4.95 ± 0.17 b | 4.74 ± 0.06 b | 4.78 ± 1.91 b | 4.52 ± 0.90 b |
8 | Quercetin 3-O-rutinoside-7-O-pentoside | 3.88 | 255/355 | 741 | 609/301 | 0.10 ± 0.01 a | 0.08 ± 0.00 a | 0.07 ± 0.03 a | 0.25 ± 0.20 b | 0.26 ± 0.24 b | 0.08 ± 0.03 a | 0.30 ± 0.12 b |
9 | Quercetin 3-O-rutinoside-7-O-rhamnoside | 3.99 | 255/345 | 755 | 609/301 | 2.02 ± 0.27 b | 1.60 ± 0.15 a | 1.72 ± 0.15 a | 1.89 ± 0.27 a | 2.13 ± 0.90 b | 1.49 ± 0.13 a | 1.86 ± 0.38 a |
10 | Quercetin 3-O-glucoside-pentoside | 4.05 | 255/345 | 595 | 301 | 2.11 ± 0.12 b | 1.85 ± 0.07 a | 1.60 ± 0.19 a | 2.05 ± 0.06 b | 1.74 ± 1.10 a | 1.10 ± 0.49 a | 2.12 ± 0.48 b |
11 | Kaempferol 3,7-O-di-glucoside | 4.22 | 264/339 | 609 | 447/285 | 0.94 ± 0.00 b | 0.65 ± 0.05 a | 0.78 ± 0.02 b | 0.75 ± 0.03 b | 0.53 ± 0.26 a | 0.47 ± 0.01 a | 0.88 ± 0.35 b |
12 | Quercetin 3-O-glucoside-7-O-glucuronide | 4.30 | 255/352 | 639 | 463/301 | 2.89 ± 0.14 a | 4.14 ± 0.13 b | 4.10 ± 0.25 b | 4.42 ± 0.09 b | 2.72 ± 0.35 a | 2.99 ± 0.22 a | 2.81 ± 0.11 a |
13 | Quercetin 3-O-rutinoside (Rutin) | 4.38 | 255/352 | 609 | 301 | 25.41 ± 1.58 a | 26.31 ± 0.06 a | 24.33 ± 0.13 a | 25.13 ± 0.77 a | 33.89 ± 8.25 b | 39.95 ± 4.28 b | 35.76 ± 3.03 b |
14 | Quercetin 3-O-glucoside | 4.61 | 255/355 | 463 | 301 | 11.79 ± 0.13 b | 9.20 ± 0.58 a | 10.83 ± 0.22 b | 8.85 ± 0.01 a | 10.17 ± 1.99 b | 8.82 ± 3.82 a | 8.76 ± 0.67 a |
15 | Quercetin 3-O-(6″-acetyl)-glucoside | 4.96 | 255/352 | 505 | 463/301 | 7.83 ± 0.57 c | 7.93 ± 0.28 c | 8.83 ± 0.33 c | 9.11 ± 0.03 c | 3.49 ± 1.00 a | 3.74 ± 0.29 a | 5.24 ± 2.33 b |
16 | 3,4-dicaffeoylquinic acid | 5.14 | 288 sh/328 | 515 | 353/191 | 15.58 ± 0.13 a | 18.19 ± 0.61 a | 16.34 ± 0.32 a | 16.51 ± 0.18 a | 16.36 ± 3.25 a | 18.39 ± 2.02 a | 17.15 ± 0.13 a |
17 | Quercetin 3-O-glucuronide | 5.32 | 255/348 | 477 | 301 | 12.90 ± 0.66 b | 11.41 ± 0.29 b | 12.35 ± 0.67 b | 10.94 ± 0.94 b | 8.09 ± 3.33 a | 7.00 ± 0.82 a | 7.46 ± 1.40 a |
18 | 1.5-di-caffeoyl-quinic acid | 5.48 | 288 sh/326 | 515 | 353/179 | 1.04 ± 0.04 a | 1.12 ± 0.03 a | 1.09 ± 0.09 a | 1.04 ± 0.24 a | 1.00 ± 0.01 a | 1.13 ± 0.09 a | 2.02 ± 0.52 b |
19 | Kaempferol 3-O-rhamnoside-7-O-pentoside | 5.66 | 264/345 | 563 | 431/285 | 2.95 ± 0.12 b | 3.79 ± 0.26 b | 3.82 ± 0.14 b | 3.69 ± 0.40 b | 1.68 ± 0.56 a | 1.50 ± 0.13 a | 1.71 ± 0.62 a |
20 | Unspecified caffeoyl-quinic derivative | 6.55 | 288 sh/322 | 538 | 341/191 | 1.07 ± 0.17 a | 1.11 ± 0.10 a | 1.43 ± 0.00 b | 1.61 ± 0.51 b | 0.89 ± 0.09 a | 0.70 ± 0.09 a | 1.01 ± 0.31 a |
21 | Quercetin | 6.62 | 255/355 | 301 | - | 1.24 ± 0.11 c | 0.88 ± 0.09 b | 0.61 ± 0.11 a | 0.82 ± 0.11 b | 0.72 ± 0.19 a | 0.68 ± 0.10 a | 0.84 ± 0.13 b |
22 | Naringenin | 7.53 | 271/317 | 271 | - | 0.60 ± 0.05 a | 0.85 ± 0.01 b | 0.48 ± 0.39 a | 0.92 ± 0.23 b | 1.05 ± 0.25 b | 0.81 ± 0.26 b | 0.84 ± 0.38 b |
23 | Quercetin 7-methyl ether | 7.98 | 255/355 | 315 | - | 0.28 ± 0.04 c | 0.07 ± 0.04 a | 0.53 ± 0.58 d | 0.13 ± 0.04 a | 0.16 ± 0.07 b | 0.15 ± 0.01 b | 0.11 ± 0.00 a |
Temperature of Sugar Syrup | Ozone Concentration (ppm) | Time of Ozonation (min) | L* ± SD | a* ± SD | b* ± SD |
---|---|---|---|---|---|
30 °C | 0 | 0 | 69.60 ± 1.01 b* | 0.22 ± 0.04 c** | 41.87 ± 3.06 b** |
10 | 5 | 69.34 ± 0.98 bB* | 0.00 ± 0.00 bA** | 38.87 ± 2.79 bA* | |
15 | 68.35 ± 1.26 bB* | 0.10 ± 0.06 bA** | 38.64 ± 1.67 bA* | ||
30 | 75.00 ± 1.19 cB* | −1.98 ± 0.16 aA* | 31.94 ± 3.27 aA* | ||
100 | 5 | 60.41 ± 0.87 aA* | 5.67 ± 0.36 dB** | 49.69 ± 2.09 cB* | |
15 | 58.45 ± 0.94 aA* | 5.66 ± 0.048 dB* | 49.90 ± 1.97 cB* | ||
30 | 61.05 ± 2.06 aA* | 2.41 ± 0.09 bB* | 43.07 ± 3.07 bB* | ||
60 °C | 0 | 0 | 77.48 ± 2.75 b** | −3.64 ± 0.47 a* | 36.61 ± 2.11 a* |
10 | 5 | 72.62 ± 1.05 bB** | −2.22 ± 0.07 bA* | 36.50 ± 2.97 Aa* | |
15 | 74.18 ± 1.97 bB** | −2.76 ± 0.09 bA* | 36.34 ± 1.64 aA* | ||
30 | 70.59 ± 0.36 bB* | −1.95 ± 0.04 cA* | 36.93 ± 2.07 aA* | ||
100 | 5 | 66.45 ± 1.09 aA** | 1.91 ± 0.10 bB* | 46.40 ± 2.46 bB* | |
15 | 60.54 ± 0.46 aA* | 4.98 ± 1.16 cB* | 51.18 ± 2.46 bB* | ||
30 | 61.92 ± 0.76 aA* | 3.29 ± 0.97 cB** | 48.37 ± 1.79 bB* |
No. | RT (min) | Peak Share in the Chromatogram (%) | Ordinary Substance Name | |||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
0 ppm 0 min | 5 min 10 ppm | 15 min 10 ppm | 30 min 10 ppm | 5 min 100 ppm | 15 min 100 ppm | 30 min 100 ppm | ||||||||||
30 °C | 60 °C | 30 °C | 60 °C | 30 °C | 60 °C | 30 °C | 60 °C | 30 °C | 60 °C | 30 °C | 60 °C | 30 °C | 60 °C | |||
1 | 9.80 | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | benzyl alcohol |
2 | 10.42 | 19.09 bB | 16.56 aA | 18.91 bA | 16.03 aA | 13.85 aA | 16.47 aB | 26.61 cB | 15.49 aA | 18.85 bA | 21.53 bB | 25.37 cA | 22.05 bA | 26.61 cB | 21.77 bA | (Z)-linalool oxide |
3 | 10.91 | 13.28 dB | 10.75 cA | 2.16 aA | 5.82 aB | 9.90 cA | 8.30 bA | 4.35 bA | 11.28 cB | 9.90 cA | 8.56 bA | 7.44 cA | 9.65 bA | 4.34 bA | 7.32 bB | linalool |
4 | 11.12 | 2.36 aA | trace | 2.27 aA | trace | 2.48 aA | 2.26 aA | trace | 2.41 aA | 2.48 aA | trace | trace | trace | trace | trace | trans-rose oxide |
5 | 11.95 | 1.55 aA | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | trace | furfural |
6 | 12.14 | 32.79 aA | 36.77 aA | 42.19 bA | 39.34 aA | 46.11 bA | 41.12 bA | 48.63 bB | 43.51 bA | 36.11 aA | 42.94 bB | 46.87 bA | 45.19 bA | 48.62 bA | 45.57 bA | linalool oxide |
7 | 12.86 | 1.10 aA | 3.37 bB | 1.86 aA | 4.35 bB | 1.26 aA | trace | trace | 2.37 aA | trace | 6.34 cA | 5.54 bA | 5.03 cA | trace | 4.91 cA | coumaran |
8 | 13.04 | 18.32 cA | 16.16 bA | 14.77 cA | 17.42 cB | 15.96 cA | 17.25 cA | 8.41 bA | 15.26 bB | 15.96 cA | 13.34 bA | 4.94 aA | 11.06 bB | 8.41 bA | 7.32 aA | isomenthyl acetate |
9 | 13.26 | 2.16 aA | 2.47 bA | 4.25 cA | trace | 2.00 aA | 2.21 bA | trace | 2.18 bA | 3.00 bB | 1.50 aA | trace | 4.91 cA | trace | 4.14 cA | (Z)-citral |
10 | 14.33 | 2.40 aA | trace | 3.48 bA | 4.06 bA | trace | trace | 4.08 cB | 1.66 aA | 3.48 bB | 1.36 aA | 2.75 aA | trace | 4.07 cB | 1.55 aA | p-vinyl guaiacol |
11 | 14.45 | 2.76 aA | 3.08 aA | 2.87 aA | 3.75 aB | 2.02 aA | 3.13 aB | 3.70 bA | 3.25 aA | 3.02 bA | trace | 3.75 bA | trace | 3.69 bA | trace | 4-methoxy-2,3,6-trimethyl-phenol |
12 | 15.05 | 3.33 bB | 1.87 aA | 2.73 bA | trace | 1.78 aA | 1.73 aA | 4.22 cB | 2.39 aA | 3.77 cA | trace | 3.33 bA | trace | 4.22 cA | 4.00 bA | 3,4-dimethoxy styrene |
TOTAL | 99.08 bB | 91.03 aA | 95.49 aB | 90.77 aA | 95.36 aA | 92.75 aA | 100.00 bA | 99.80 bA | 96.57 aA | 95.57 bA | 99.99 bA | 97.89 bA | 99.96 bA | 96.58 bA |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Matłok, N.; Kapusta, I.; Piechowiak, T.; Zardzewiały, M.; Gorzelany, J.; Balawejder, M. Characterisation of Some Phytochemicals Extracted from Black Elder (Sambucus nigra L.) Flowers Subjected to Ozone Treatment. Molecules 2021, 26, 5548. https://doi.org/10.3390/molecules26185548
Matłok N, Kapusta I, Piechowiak T, Zardzewiały M, Gorzelany J, Balawejder M. Characterisation of Some Phytochemicals Extracted from Black Elder (Sambucus nigra L.) Flowers Subjected to Ozone Treatment. Molecules. 2021; 26(18):5548. https://doi.org/10.3390/molecules26185548
Chicago/Turabian StyleMatłok, Natalia, Ireneusz Kapusta, Tomasz Piechowiak, Miłosz Zardzewiały, Józef Gorzelany, and Maciej Balawejder. 2021. "Characterisation of Some Phytochemicals Extracted from Black Elder (Sambucus nigra L.) Flowers Subjected to Ozone Treatment" Molecules 26, no. 18: 5548. https://doi.org/10.3390/molecules26185548