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Hyphenated technique for the extraction and determination of isoflavones in algae: Ultrasound-assisted supercritical fluid extraction followed by fast chromatography with tandem mass spectrometry
Abstract
New hyphenated technique for the extraction and determination of isoflavones in sea and freshwater algae and cyanobacteria was developed. The method consists of sonication sample pretreatment, extraction by supercritical CO(2) modified by 3% (v/v) of MeOH/H(2)O mixture (9:1, v/v) at 35 MPa and 40°C for 60 min, fast chromatography analysis by the means of Agilent 1200 Series Rapid Resolution and MS/MS determination. Agilent 1200 Series RRLC was used with Zorbax SB-CN chromatographic column (100 mm × 2.1mm, particle size 3.5 μm), 3μl injection volume, mobile phase consisting of 0.2% (v/v) acetic acid in water (solvent A) and acetonitrile (solvent B) and used with linear gradient (30% B at 0 min, from 0 min to 3 min up to 50% B, from 3 to 6 min up to 80% B and from 6 to 10 min down to 30% B). The flow-rate was 0.4 mL/min, column oven temperature 35°C. MS detector Agilent Technologies 6460 Triple quadrupole LC/MS with Agilent Jet Stream was used in a negative ESI mode under following conditions: gas temperature 350°C, gas flow 13 L/min, nebulizer gas pressure 50 psi, sheath gas temperature 400°C, sheath gas flow 12L/min, capillary voltage was 4 kV. Samples were analysed in the multiple reaction monitoring (MRM) mode. Eight isoflavone compounds were found for the first time in seven real samples of sea algae and in three control samples of freshwater algae and cyanobacteria. Usual optimisation study of extraction parameters was performed. Pressure and temperature optima for algae matrix are different from those obtained sooner for other matrices for most of the analytes, but the results of modifier optimisation study are in good accordance with those obtained sooner for spiked samples and red clover matrix. It seems that matrix has very small or no effect on the modifier selection. Two different approaches of sonication pretreatment were tested: sonication bath and the thorn instrument. In longer extraction time experiments, thorn sonication was more efficient and recovery of following supercritical fluid extraction was higher.
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“However, some authors used SC-CO2 for the extraction of lipids [41], volatile compounds [43], isoflavones [44], plant growth hormones, and micro- and macroelements from various types of seaweeds [45].”
From Overview on the Application of Modern Methods for the Extraction of Bioactive Compounds from Marine Macroalgae (2018) · cites this paper as [44]
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“…of isofl avones from sea macroalgae ( Sargassum muticum, Sargassum vulgare, Hypnea spinella, Porphyra sp. , Undaria pinnatifi da, Chondrus crispus, and Halopytis incurvus ), freshwater algae ( Spongiochloris spongiosa ), and cyanobacteria (Scenedesmus and Nostoc 17; Klejdus et al. 2010 ) .”
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“SFE Efficient, economical [6] Fast extraction rate (allow to avoid degradation of labile compounds) and high yield [5, 6, 16, 26] Ecofriendly technology with minimal or no use of organic solvents [5, 6, 16, 26, 45] The very low critical temperature of CO2 allows its use for thermolabile [16, 45] and easily oxidized co…”
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“, Undaria pinnatifida, Chondrus crispus, Halopytis incurvus 10–40 35–75 10–60 Isoflavones [44]”
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“Concerning red algae, SFE has been employed to extract specially lipophilic sub-stances, such as glycolipids, phospholipids, and x -3 fatty acids (Herrero et al. 2006; Klejdus et al. 2010; Michalak and Chojnacka 2014; Terme et al. 2018).”
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“[54] identified eight isoflavones (daidzin, daidzein, genistein, formononetin, sissotrin, biochanin A and ononin) in seven red and brown seaweeds, with the highest concentrations present in Chondrus crispus (red seaweed 86–229 ng/g) followed by Halopytis incurvus (red seaweed 7–50 ng/g) and Sargassum muticum (brown se…”
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Liu, X., Ou, H., Xiang, Z., & Gregersen, H. N. (2020) · Journal of Applied Research on Medicinal and Aromatic Plants · doi:10.1016/j.jarmap.2020.100265 · Cited by 39
Wei, M., Yang, Y., Chiu, H., & Hong, S. (2013) · Journal of Chromatography B · doi:10.1016/j.jchromb.2013.09.015 · Cited by 37
Kapoor, S., Singh, M., Srivastava, A., Chavali, M. S., Chandrasekhar, K., & Verma, P. (2021) · Journal of Basic Microbiology · doi:10.1002/jobm.202100458 · Cited by 38
Yang, Y., Wei, M., Hong, S., Huang, T., & Lee, S. (2013) · Industrial Crops and Products · doi:10.1016/j.indcrop.2013.05.013 · Cited by 36
Yang, Y., & Wei, M. (2017) · Food Chemistry · doi:10.1016/j.foodchem.2017.12.086 · Cited by 34
Bustamante-Rangel, M., Delgado-Zamarreño, M. M., Pérez‐Martín, L., & Carabias-Martı́nez, R. (2012) · Microchemical Journal · doi:10.1016/j.microc.2012.10.023 · Cited by 34
“The application of techniques such as ultrasound-assisted extraction (UAE) [11], microwave-assisted extraction (MAE) [12], pressurized liquid extraction (PLE) [13] or supercritical fluid extraction (SFE) [14] for the extraction of isoflavones from food samples offers advantages such as a reduction in extraction time,…”
MethodKanumuri, R. S., Kadian, N., Taneja, I., & Wahajuddin, M. (2015) · Phytochemistry Reviews · doi:10.1007/s11101-015-9400-x · Cited by 33
“Klejdus et al. (2010) developed a hyphenated ultrasound assisted super critical fluid extraction method for the extraction and determination of isoflavones in sea and freshwater algae and cyanobacteria .”
BackgroundMethodInfluentialKadam, S. U., Álvarez, C., Tiwari, B. K., & O’Donnell, C. P. (2015) · Elsevier eBooks · doi:10.1016/b978-0-12-418697-2.00004-0 · Cited by 32
Azim, N. H., Subki, A., & Yusof, Z. N. B. (2018) · Malaysian Journal of Microbiology · doi:10.21161/mjm.100317 · Cited by 32
Sigamani, S., Nandhagopal, M., Ragavendran, C., Mathivanan, N., Natarajan, D., Hemalatha, N., & Dhandapani, R. (2019) · Journal of Applied Microbiology · doi:10.1111/jam.14336 · Cited by 30
“Klejdus et al. (2010) have reported the presence of phytochemicals like flavonoids, glycosides, phenolic compounds, terpenoids and saponins from the methanol extracts of two microalgal strains.”
BackgroundBlooming cyanobacteria alter water flea reproduction via exudates of estrogen analogues
Xu, R., Jiang, Y., MacIsaac, H. J., Chen, L., Li, J., Xu, J., Wang, T., Zi, Y., & Chang, X. (2019) · The Science of The Total Environment · doi:10.1016/j.scitotenv.2019.133909 · Cited by 30
“Therefore, their contributions to estrogenic effects should not be overlooked, especially considering the discovery of phytoestrogens in blooming cyanobacteria (Goiris et al., 2014; Klejdus et al., 2010; Procházková et al., 2017).”
BackgroundAstudillo-Pascual, M., Domínguez, I., Aguilera, P. A., & Frenich, A. G. (2021) · Plants · doi:10.3390/plants10050864 · Cited by 30
“To our knowledge it is also the first time t at these compounds have been reported in any marine seagrass, it being more common to find them in other samples such as leg mes and algae for biochanin A and glycitein, respectively [37,38].”
BackgroundPark, S., Sharma, A., & Lee, H. (2024) · Marine Drugs · doi:10.3390/md22010047 · Cited by 28
Castillo, A., Celeiro, M., Lores, M., Grgić, K., Banožić, M., Jerković, I., & Jokić, S. (2023) · Marine Drugs · doi:10.3390/md21020097 · Cited by 30
“Different isoflavones, such as daidzein or genistein, were identified in Sargassum muticum and Sargassum vulgare [15].”
An Overview of Nanoformulated Nutraceuticals and their Therapeutic Approaches
De, S., Agraharam, G., Keerthana, V., Girigoswami, A., & Girigoswami, K. (2020) · Current Nutrition & Food Science · doi:10.2174/1573401316999200901120458 · Cited by 27
Rahman, N. A., Katayama, T., Wahid, M. E. A., Kasan, N. A., Khatoon, H., Yamada, Y., & Takahashi, K. (2020) · Frontiers in Bioengineering and Biotechnology · doi:10.3389/fbioe.2020.581628 · Cited by 28
Determination of Phytoestrogen Content in Fresh-Cut Legume Forage
Hloučalová, P., Skládanka, J., Horký, P., Klejdus, B., Pelikán, J., & Knotová, D. (2016) · Animals · doi:10.3390/ani6070043 · Cited by 27
Seaweeds: a nutraceutical and health food
Hayes, M. (2015) · Elsevier eBooks · doi:10.1016/b978-0-12-418697-2.00014-3 · Cited by 26
Prochazkova, T., Sychrová, E., Večerková, J., Javůrková, B., Otoupalíková, A., Pernica, M., Šimek, Z., Smutná, M., Lepšová-Skácelová, O., & Hilscherová, K. (2018) · Water Research · doi:10.1016/j.watres.2018.02.040 · Cited by 22
Tsiaka, T., Sinanoglou, V. J., & Zoumpoulakis, P. G. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-811521-3.00008-9 · Cited by 22
Green analytical methodologies for the discovery of bioactive compounds from marine sources
Duarte, K., Justino, C. I. L., Pereira, R., Freitas, A. C., Gomes, A. M., Duarte, A. C., & Rocha-Santos, T. A. P. (2014) · Trends in Environmental Analytical Chemistry · doi:10.1016/j.teac.2014.11.001 · Cited by 21
Zayed, A., El-Seadawy, H. M., Attia, E. Z., Rushdi, M. I., & Abdelmohsen, U. R. (2024) · Frontiers in Natural Products · doi:10.3389/fntpr.2024.1425242 · Cited by 23
Microalgae as a Novel Source of Antioxidants for Nutritional Applications
Goiris, K., Muylaert, K., & Cooman, L. D. (2015) · Elsevier eBooks · doi:10.1016/b978-0-12-800776-1.00017-0 · Cited by 21
Advanced Extraction Processes to Obtain Bioactives from Marine Foods
Plaza, M., & Rodríguez‐Meizoso, I. (2013) · Wiley eBooks · doi:10.1002/9781118412893.ch16 · Cited by 21
Gager, L., Lalegerie, F., Connan, S., & Stiger‐Pouvreau, V. (2021) · Wiley eBooks · doi:10.1002/9781119542650.ch11 · Cited by 23
Khalil, A. H., Aidy, E. A., Said, M. A., Kebeish, R., & Al-Badwy, A. H. (2024) · Algal Research · doi:10.1016/j.algal.2024.103624 · Cited by 21
Fan, L., Jin, R., Liu, Y., An, M., & Chen, S. (2011) · Journal of Chromatography B · doi:10.1016/j.jchromb.2011.09.035 · Cited by 20
Shetty, V., & Sibi, G. (2014) · Journal of Food Resource Science · doi:10.3923/jfrs.2015.1.9 · Cited by 20
“A number of phenolic compounds are present in microalgae (Klejdus et al., 2010; Kovacik et al., 2010) and were reported to responsible for microalgal antioxidant properties.”
BackgroundDeniz, İ., García‐Vaquero, M., & İmamoğlu, E. (2017) · Elsevier eBooks · doi:10.1016/b978-0-08-101023-5.00018-2 · Cited by 21
Radwan, A. M., Ahmed, E., Donia, A. E. R. M., Mustafa, A. E., & Balah, M. A. A. (2023) · Scientific Reports · doi:10.1038/s41598-023-38711-8 · Cited by 20
Benedé, J. L., Chisvert, A., Lucena, R., & Cárdenas, S. (2021) · Talanta · doi:10.1016/j.talanta.2021.122582 · Cited by 18
Sushanth, V. R., & Rajashekhar, M. (2015) · Cited by 18
Mosaddik, A., Ravinayagam, V., Elaanthikkal, S., Fessi, H., Badri, W., & Elaı̈ssari, A. (2018) · Springer eBooks · doi:10.1007/978-3-030-00545-0_11 · Cited by 18
Visnevschi‐Necrasov, T., Barreira, J. C. M., Cunha, S. C., Pereira, G., Nunes, E., & Oliveira, M. B. P. P. (2014) · Phytochemical Analysis · doi:10.1002/pca.2534 · Cited by 18
“…Soxhlet extraction, ultrasound-assisted solvent extraction, Wiley & Sons, Ltd. microwave-assisted solvent extraction, accelerated solvent extraction and supercritical fluid extraction, have already been used for isolation of phytochemicals (Klejdus et al., 2004, 2010; Oniszczuk et al., 2013).”
MethodSupercritical CO2 extraction of total flavonoids from Iberis amara assisted by ultrasound
Liu, X., Ou, H., Zuo, J., & Gregersen, H. N. (2022) · The Journal of Supercritical Fluids · doi:10.1016/j.supflu.2022.105581 · Cited by 16
The Beneficial and Adverse Effects of Phytoestrogens
Blázovics, A., Csorba, B., & Ferencz, A. (2022) · OBM Integrative and Complementary Medicine · doi:10.21926/obm.icm.2203034 · Cited by 16
Metadata
- Authors
- Klejdus, B., Lojková, L., Plaza, M., Šnóblová, M., & Štěrbová, D.
- Affiliations
- Mendel University in Brno (CZ)
- Consejo Superior de Investigaciones Científicas (ES)
- Corresponding author
- Klejdus, B.
- Venue
- Journal of Chromatography A
- Publisher
- Elsevier BV
- Published
- 2010-12
- Volume
- 1217
- Issue
- 51
- Pages
- 7956-7965
- ISSN
- 0021-9673 (ISSN-L)
- OpenAlex
- W2008516333
- Cited by
- 182
- References
- 24
- Citations by year
- 2026: 8 · 2025: 11 · 2024: 10 · 2023: 19 · 2022: 12 · 2021: 19 · 2020: 12 · 2019: 16 · 2018: 11 · 2017: 5 · 2016: 4 · 2015: 13 · 2014: 13 · 2013: 15 · 2012: 9
- FWCI
- 13.71
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Chromatography A (publishedVersion)
- PubMed (publishedVersion)
- DIGITAL.CSIC (Spanish National Research Council (CSIC)) (submittedVersion)
- Funders
- Grantová Agentura České Republiky
- Topics
- Life Sciences › Agricultural and Biological Sciences › Aquatic Science › Seaweed-derived Bioactive Compounds
- Physical Sciences › Chemistry › Analytical Chemistry › Analytical chemistry methods development
- Physical Sciences › Chemistry › Analytical Chemistry › Chromatography in Natural Products
- Keywords
- isoflavones, algae, cyanobacteria, ultrasonic pretreatment, isoflavone extraction, seaweed, freshwater algae, isoflavone quantification, extraction time optimization
- MeSH terms
- Phaeophyceae, Rhodophyta, Chromatography, Liquid, Isoflavones, Ultrasonics, Chromatography, Supercritical Fluid, Tandem Mass Spectrometry
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