GAO Yawen, WU Guopeng, HAN Bo, et al. Synthesis and Antioxidant Activity of Selenized Apigenin[J]. Science and Technology of Food Industry, 2025, 46(4): 109−116. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2024030269.
Citation: GAO Yawen, WU Guopeng, HAN Bo, et al. Synthesis and Antioxidant Activity of Selenized Apigenin[J]. Science and Technology of Food Industry, 2025, 46(4): 109−116. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2024030269.

Synthesis and Antioxidant Activity of Selenized Apigenin

More Information
  • Received Date: March 17, 2024
  • Available Online: December 07, 2024
  • Selenized apigenin (Se-AP) synthesized using sodium selenite employed as a highly reactive selenide reagent and the flavonoid apigenin (AP) as a substrate was investigated in this paper. Followed by a series of analytical techniques were used to characterize structure of Se-AP and extrapolate the possible coordination structures in Se-AP. Se content of Se-AP was measured from the fluorescent spectrophotometry to be about 1.91%±0.11%. Based on the results of structural characterization analysis, there could be concluded that new Se-O and C-O-Se bonds were formed without altering the main structure of the flavonoid backbone in selenized apigenin. The Se elements were evenly distributed in Se-AP, and one possible coordination structure of Se-AP was inferred. In addition, the antioxidant activity of AP and Se-AP was investigated by designing ABTS+, DPPH, and OH radical scavenging experiments. The in vitro antioxidant results suggested that Se-AP exhibited a clearance rate of 93.82%±0.63% for ABTS+ radicals at a concentration of 400 mg/L, 39.53%±0.67% for DPPH radicals and 96.54%±0.77% for OH radicals at a concentration of 800 mg/L and the ability of scavenging DPPH free radicals was slightly enhanced, while the scavenging ability of ABTS+ and OH radicals was significantly increased (IC50 was 53.52±1.85 mg/L and 11.33±0.64 mg/L), and the scavenging ability was comparable to that of VC at 800 mg/L at the same concentration for Se-AP. Therefore, the present data indicated that selenylation modification of AP could increase the antioxidant activity and enhance the biological activity, which could offer the possibility of the development and utilization of selenized flavonoid-related foods and drugs.
  • [1]
    HODGSON R, KENNEDY B K, MASLIAH E, et al. Aging:Therapeutics for a healthy future[J]. Neuroscience & Biobehavioral Reviews,2020,108:453−458.
    [2]
    MILANI P, AMBROSI G, GAMMOH O, et al. SOD1 and DJ-1 converge at Nrf2 pathway:a clue for antioxidant therapeutic potential in neurodegeneration[J]. Oxidative Medicine and Cellular Longevity,2013,2013:1−12.
    [3]
    YANG. H, HUA J L, WANG C. Anti-oxidation and anti-aging activity of polysaccharide from malus micromalus makino fruit wine[J]. International Journal of Biological Macromolecules,2019,121:1203−1212. doi: 10.1016/j.ijbiomac.2018.10.096
    [4]
    PRECI D P, ALMEIDA A, WEILER A L, et al. Oxidative damage and antioxidants in cervical cancer[J]. International Journal of Gynecologic Cancer,2021,31(2):265−271. doi: 10.1136/ijgc-2020-001587
    [5]
    WARRAICH U A, HUSSAIN F, KAYANI H U R. Aging-oxidative stress, antioxidants and computational modeling[J]. Heliyon,2020,6(5):04107.
    [6]
    王聪颖, 黄小强, 徐玥玥, 等. 枸杞子多糖的提取纯化、体外抗氧化及其抗衰老作用[J]. 食品工业科技, 2024,45(19):1−8. [WANG C Y, HUANG X Q, XU Y Y, et al. Extraction and purification of lycium barbarum polysaccharides, in vitro antioxidation and in vivo anti-aging effects[J]. Science and Technology of Food Industry, 2024,45(19):1−8.]

    WANG C Y, HUANG X Q, XU Y Y, et al. Extraction and purification of lycium barbarum polysaccharides, in vitro antioxidation and in vivo anti-aging effects[J]. Science and Technology of Food Industry, 2024, 45(19): 1−8.
    [7]
    LIMA D P D, JÚNIOR E D S P, MENEZES A V D, et al. Chemical composition, minerals concentration, total phenolic compounds, flavonoids content and antioxidant capacity in organic and conventional vegetables[J]. Food Research International, 2024, 175.
    [8]
    QI Q Q, CHU M J, YU X T, et al. Anthocyanins and proanthocyanidins:chemical structures, food sources, bioactivities, and product development[J]. Food Reviews International,2022,39(7):4581−4609.
    [9]
    MUSIAL C, JANKOWSKA A K, PONIKOWSKA M G, et al. Beneficial properties of green tea catechins[J]. International Journal of Molecular Sciences,2020,21(5):1744. doi: 10.3390/ijms21051744
    [10]
    ZHANG F, LI X, WEI Y. Selenium and selenoproteins in health[J]. Biomolecules,2023,13(5):799. doi: 10.3390/biom13050799
    [11]
    WANG L, LI X, WANG B. Synthesis, characterization and antioxidant activity of selenium modified polysaccharides from hohenbuehelia serotina[J]. International Journal of Biological Macromolecules,2018,120:1362−1368. doi: 10.1016/j.ijbiomac.2018.09.139
    [12]
    ANGULO-ELIZARI E, RAZA A, ENCÍO I, et al. Seleno-warfare against cancer:Decoding antitumor activity of novel acylselenoureas and se-acylisoselenoureas[J]. Pharmaceutics,2024,16(2):272. doi: 10.3390/pharmaceutics16020272
    [13]
    DEMIRCAN K, HYBSIER S, CHILLON T S, et al. Sex-specific associations of serum selenium and selenoprotein P with type 2 diabetes mellitus and hypertension in the berlin aging study II[J]. Redox Biology,2023,65:102823. doi: 10.1016/j.redox.2023.102823
    [14]
    马金凤. 以二氧化硒为硒源的苯胺/咪唑并吡啶/黄酮类硒化物的合成[D]. 镇江:江苏大学, 2021. [MA J F. Synthesis of selenide anilines/ imidazopyridine/ flavonoids with selenium dioxide as selenium source[D]. Zhenjiang:Jiangsu University, 2021.]

    MA J F. Synthesis of selenide anilines/ imidazopyridine/ flavonoids with selenium dioxide as selenium source[D]. Zhenjiang: Jiangsu University, 2021.
    [15]
    余香. 槲皮素硒配合物的合成及其抗氧化膜的制备与性能研究[D]. 南宁:广西大学, 2023. [YU X. Synthesis of quercetin selenium complexes and the preparation and properties of their antioxidant films[D]. Nanning:Guangxi University, 2023.]

    YU X. Synthesis of quercetin selenium complexes and the preparation and properties of their antioxidant films[D]. Nanning: Guangxi University, 2023.
    [16]
    黄九林, 彭博, 丁瑜瑜, 等. 大黄素-硒(Ⅳ)配合物的合成、表征及抗氧化活性研究[J]. 化学试剂,2021,43(7):992−995. [HUANG J L, PENG B, DING Y Y, et al. Synthesis, characterization and antioxidant activity of emodin-selenium(IV) complex[J]. Chemical Reagent,2021,43(7):992−995.]

    HUANG J L, PENG B, DING Y Y, et al. Synthesis, characterization and antioxidant activity of emodin-selenium(IV) complex[J]. Chemical Reagent, 2021, 43(7): 992−995.
    [17]
    张莉萍, 刘衍季, 余卫强, 等. 橙皮素微量元素配合物的合成及其生物活性研究[J]. 中国现代应用药学,2021,38(16):1958−1963. [ZHANG L P, LIU Y J, YU W Q, et al. Study on the synthesis and bioactivity of the complexes of hesperetin with trace elements[J]. Modern Applied Pharmacy in China,2021,38(16):1958−1963.]

    ZHANG L P, LIU Y J, YU W Q, et al. Study on the synthesis and bioactivity of the complexes of hesperetin with trace elements[J]. Modern Applied Pharmacy in China, 2021, 38(16): 1958−1963.
    [18]
    POUREINI F, NAJAFPOUR G D, NIKZAD M, et al. Loading of apigenin extracted from parsley leaves on colloidal core-shell nanocomposite for bioavailability enhancement[J]. Colloids and Surfaces A:Physicochemical and Engineering Aspects,2021,625:126867.
    [19]
    MADUNIĆ J, MADUNIĆ I V, GAJSKI G, et al. Apigenin:A dietary flavonoid with diverse anticancer properties[J]. Cancer Letters,2018,413:11−22. doi: 10.1016/j.canlet.2017.10.041
    [20]
    LOTFI M S, RASSOULI F B. Natural flavonoid apigenin, an effective agent against nervous system cancers[J]. Molecular Neurobiology, 2024.
    [21]
    CHEN P, CHEN F, GUO Z, et al. Recent advancement in bioeffect, metabolism, stability, and delivery systems of apigenin, a natural flavonoid compound:challenges and perspectives[J]. Frontiers in Nutrition, 2023, 10:1221227.
    [22]
    PRATAS A, MALHÃO B, PALMA R, et al. Effects of apigenin on gastric cancer cells[J]. Biomedicine & Pharmacotherapy,2024,172:116251.
    [23]
    赵鸣飞. 姜黄素—硒配合物的合成及对镉染毒大鼠肝损伤的干预作用[D]. 唐山:华北理工大学, 2015. [ZHAO M F. Synthesis of curcumin-selenium coordination compound and intervention on liver injury exposed to cadmium in rat[D]. Tangshan:North China University of Science and Technology, 2015.]

    ZHAO M F. Synthesis of curcumin-selenium coordination compound and intervention on liver injury exposed to cadmium in rat[D]. Tangshan: North China University of Science and Technology, 2015.
    [24]
    中华人民共和国国土资源部. DZ/T 0253.2-2014 生态地球化学评价动植物样品分析方法第二部分:硒量的测定原子荧光光谱法[S]. 北京:中国标准出版社, 2014. [Ministry of Land and Resources of the People's Republic of China. DZ/T 0253.2-2014 Analytic methods for biologic samples in eco-geochemistry assessment Part 2:Determination of selenium content fluorescent spectrophotometry[S]. Beijing:Standards Press of China, 2014.]

    Ministry of Land and Resources of the People's Republic of China. DZ/T 0253.2-2014 Analytic methods for biologic samples in eco-geochemistry assessment Part 2: Determination of selenium content fluorescent spectrophotometry[S]. Beijing: Standards Press of China, 2014.
    [25]
    温启华, 陆逸昊, 杨露芳, 等. 硒化天麻多糖的制备、结构表征及其抗氧化活性评价[J]. 食品工业科技,2024,45(3):18−30. [WEN Q H, LU Y H, YANG L F, et al. Preparation, structure characterization and antioxidant activity evaluation of selenized Gastrodia elata polysaccharides[J]. Science and Technology of Food Industry,2024,45(3):18−30.]

    WEN Q H, LU Y H, YANG L F, et al. Preparation, structure characterization and antioxidant activity evaluation of selenized Gastrodia elata polysaccharides[J]. Science and Technology of Food Industry, 2024, 45(3): 18−30.
    [26]
    黄瑜, 张锡宇, 赵海桃, 等. 沙棘叶提取物的体外抗氧化及乙酰胆碱酯酶抑制能力[J]. 精细化工,2024,41(2):391−400. [HUANG Y, ZHANG X Y, ZHAO H T, et al. In vitro antioxidant activities and acetylcholinesterase inhibition ability of hippophae rhamnoides L. leaves extract[J]. Fine Chemicals,2024,41(2):391−400.]

    HUANG Y, ZHANG X Y, ZHAO H T, et al. In vitro antioxidant activities and acetylcholinesterase inhibition ability of hippophae rhamnoides L. leaves extract[J]. Fine Chemicals, 2024, 41(2): 391−400.
    [27]
    秦毅臻, 何洋, 冯怡婷, 等. 超声辅助碱法提取无籽刺梨结合多酚工艺优化及其抗氧化活性分析[J]. 食品工业科技,2024,45(15):1−9. [QIN Y Z, HE Y, FENG Y T, et al. Study on ultrasound-assisted alkali extraction of bound polyphenol from rosa sterilis and analysis of antioxidant activity[J]. Science and Technology of Food Industry,2024,45(15):1−9.]

    QIN Y Z, HE Y, FENG Y T, et al. Study on ultrasound-assisted alkali extraction of bound polyphenol from rosa sterilis and analysis of antioxidant activity[J]. Science and Technology of Food Industry, 2024, 45(15): 1−9.
    [28]
    马玲龙. 黄酮类—铜(Ⅱ)配合物的合成、表征及抗氧化活性研究[D]. 广州:华南农业大学, 2020. [MA L L. Synthesis, characterization and antioxidant activity of flavonoidCopper (Ⅱ) Complex[D]. Guangzhou:South China Agricultural University, 2020.]

    MA L L. Synthesis, characterization and antioxidant activity of flavonoidCopper (Ⅱ) Complex[D]. Guangzhou: South China Agricultural University, 2020.
    [29]
    陶燕枝. 构树黄酮分离鉴定及木犀草素硒配合物的合成研究[D]. 南宁:广西大学, 2022. [TAO Y Z. Isolation and identification of flavonoid from broussonetia papyrifera and synthesis of luteolin selenium complex[D]. Nanning:Guangxi University, 2022.]

    TAO Y Z. Isolation and identification of flavonoid from broussonetia papyrifera and synthesis of luteolin selenium complex[D]. Nanning: Guangxi University, 2022.
    [30]
    LIU Y, YUAN C, CUI B, et al. Encapsulation of apigenin into β-cyclodextrin metal-organic frameworks with high embedment efficiency and stability[J]. Food Chemistry,2024,443:1338543.
    [31]
    YUAN B, YANG X Q, KOU M, et al. Jiang, Selenylation of polysaccharide from the sweet potato and evaluation of antioxidant, antitumor, and antidiabetic activities[J]. Journal of Agricultural and Food Chemistry,2017,65(3):605−617. doi: 10.1021/acs.jafc.6b04788
    [32]
    MA Y, CHEN Z, WANG Z, et al. Molecular interactions between apigenin and starch with different amylose/amylopectin ratios revealed by X-ray diffraction, FT-IR and solid-state NMR[J]. Carbohydrate Polymers,2023,310:120737. doi: 10.1016/j.carbpol.2023.120737
    [33]
    周文富. 茶多酚硒配合物合成与结构表征[J]. 精细化工,2007(3):248−251,260. [ZHOU W F. Syntheses and characterizations of tea polyphenols/Selenium complexes[J]. Fine Chemicals,2007(3):248−251,260.] doi: 10.3321/j.issn:1003-5214.2007.03.011

    ZHOU W F. Syntheses and characterizations of tea polyphenols/Selenium complexes[J]. Fine Chemicals, 2007(3): 248−251,260. doi: 10.3321/j.issn:1003-5214.2007.03.011
    [34]
    ALSHEHRI S M, SHAKEEL F, IBRAHIM M A, et al. Dissolution and bioavailability improvement of bioactive apigenin using solid dispersions prepared by different techniques[J]. Saudi Pharmaceutical Journal,2019,27(2):264−273. doi: 10.1016/j.jsps.2018.11.008
    [35]
    毛敏, 李香香, 辛国鹏, 等. 硒化二氢杨梅素的制备及对肿瘤细胞增殖/转移的抑制性[J]. 精细化工,2022,39(5):950−955. [MAO M, LI X X, XIN G P, et al. Preparation of selenizing DMY and its inhibition on proliferation/metastasis of tumor cells[J]. Fine Chemicals,2022,39(5):950−955.]

    MAO M, LI X X, XIN G P, et al. Preparation of selenizing DMY and its inhibition on proliferation/metastasis of tumor cells[J]. Fine Chemicals, 2022, 39(5): 950−955.
    [36]
    JIA X, LIU G, HUANG Y, et al. Ultrasonic-assisted extraction, structural characteristics, and antioxidant activities of polysaccharides from alpinia officinarum hance[J]. Foods,2024,13(2):333. doi: 10.3390/foods13020333
    [37]
    SONG D H, LE K J, AN J H. Antioxidant activity and volatile components of sprouted oat beer[J]. Lwt,2024,193:115757. doi: 10.1016/j.lwt.2024.115757
    [38]
    黄冬婷, 黄俊生, 汤静洁, 等. 超声辅助离子液体提取人参多糖工艺及其抗氧化活性[J]. 精细化工,2022,39(9):1851−1857,1871. [HUANG D T, HUANG J S, TANG J J, et al. Ultrasonic-assisted ionic liquid extraction of ginseng polysaccharide and its antioxidant activity[J]. Fine Chemicals,2022,39(9):1851−1857,1871.]

    HUANG D T, HUANG J S, TANG J J, et al. Ultrasonic-assisted ionic liquid extraction of ginseng polysaccharide and its antioxidant activity[J]. Fine Chemicals, 2022, 39(9): 1851−1857,1871.
    [39]
    李海霞, 文丽君, 陈丽珍, 等. 芹菜素席夫碱金属配合物的合成及抗氧化活性研究[J]. 现代食品科技,2016,32(7):164−169, 294. [LI H Y, WEN L J, CHEN L Z, et al. Synthesis of schiff base metal derivatives of apigenin and their antioxidant activity[J]. Modern Food Science and Technology,2016,32(7):164−169, 294.]

    LI H Y, WEN L J, CHEN L Z, et al. Synthesis of schiff base metal derivatives of apigenin and their antioxidant activity[J]. Modern Food Science and Technology, 2016, 32(7): 164−169, 294.
    [40]
    LIU J C, GE Z, JIANG X, et al. A comprehensive review of natural products with anti-hypoxic activity[J]. Chinese Journal of Natural Medicines,2023,21(7):499−515. doi: 10.1016/S1875-5364(23)60410-8
    [41]
    SHAO C T, ZHONG J W, LIU J W, et al. Preparation, characterization and bioactivities of selenized polysaccharides from lonicera caerulea L. fruits[J]. International Journal of Biological Macromolecules,2023,225:484−493. doi: 10.1016/j.ijbiomac.2022.11.105
  • Other Related Supplements

  • Cited by

    Periodical cited type(1)

    1. 余厚美,林立铭,王琴飞,姚庆群,杜培旭,张金泉,张振文. 不同酶解工艺对鲜木薯块根粗多糖得率的影响. 热带作物学报. 2025(02): 407-419 .

    Other cited types(0)

Catalog

    Article Metrics

    Article views (62) PDF downloads (6) Cited by(1)

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return