• CA
  • JST
  • FSTA
  • SCOPUS
  • 北大核心期刊
  • 中國科技核心期刊CSTPCD
  • 中國精品科技期刊
  • RCCSE中國核心學術期刊
  • 中國農業核心期刊
  • 中國生物醫學文獻服務系統SinoMed收錄期刊
中國精品科技期刊2020

低共熔溶劑提取江南卷柏穗花杉雙黃酮的工藝優化

劉超 黎維維 雷杰 李剛 盧德敏 徐大軍 盛小娜 伍明江 王剛

劉超,黎維維,雷杰,等. 低共熔溶劑提取江南卷柏穗花杉雙黃酮的工藝優化[J]. 食品工業科技,2022,43(16):176?184. doi:  10.13386/j.issn1002-0306.2021100160
引用本文: 劉超,黎維維,雷杰,等. 低共熔溶劑提取江南卷柏穗花杉雙黃酮的工藝優化[J]. 食品工業科技,2022,43(16):176?184. doi:  10.13386/j.issn1002-0306.2021100160
LIU Chao, LI Weiwei, LEI Jie, et al. Deep Eutectic Solvents Extraction and Optimization of Amentoflavone from Selaginella moellendorffii[J]. Science and Technology of Food Industry, 2022, 43(16): 176?184. (in Chinese with English abstract). doi:  10.13386/j.issn1002-0306.2021100160
Citation: LIU Chao, LI Weiwei, LEI Jie, et al. Deep Eutectic Solvents Extraction and Optimization of Amentoflavone from Selaginella moellendorffii[J]. Science and Technology of Food Industry, 2022, 43(16): 176?184. (in Chinese with English abstract). doi:  10.13386/j.issn1002-0306.2021100160

低共熔溶劑提取江南卷柏穗花杉雙黃酮的工藝優化

doi: 10.13386/j.issn1002-0306.2021100160
基金項目: 國家自然科學基金(81302639);貴州省中醫藥管理局項目(D-449);遵義醫學院博士啟動基金(F-742);遵市科人才(2020)10號;遵市科和HZ字(2021)215號。
詳細信息
    作者簡介:

    劉超(1996?),男,碩士研究生,研究方向:天然藥物研究,E-mail:lc961027@163.com

    黎維維(1996?),女,碩士研究生,研究方向:天然藥物研究,E-mail:1298913050@qq.com

    通訊作者:

    伍明江(1981?),男,博士,教授,研究方向:中藥物質基礎及藥代動學研究,E-mail:zyyzwmj@163.com

    王剛(1978?),男,博士,教授,研究方向:天然藥物提取、分離及活性成分研究,E-mail:wg8855350@zmu.edu.cn

  • 中圖分類號: R932

Deep Eutectic Solvents Extraction and Optimization of Amentoflavone from Selaginella moellendorffii

  • 摘要: 采用低共熔溶劑超聲輔助技術提取江南卷柏中穗花杉雙黃酮(AME),并優化其工藝參數。通過一步法制備3種低共熔溶劑,并篩選出提取江南卷柏AME效果最佳低共熔溶劑,通過核磁共振、傅里葉紅外光譜和熱重分析表明低共熔溶劑被成功制備,并采用單因素和響應面法優化江南卷柏中AME的提取工藝。結果表明,最佳低共熔溶劑為氯化膽堿:香葉醇,最佳提取工藝條件為:摩爾比1:2,含水量20%,液固比10 mL/g,超聲時間31 min,超聲功率為240 W。在此條件下,AME的提取得率為(2.75±0.12) mg/g。與熱浸法、冷浸法、離子液體超聲提取法、乙醇超聲提取法進行對比表明,低共熔溶劑結合超聲提取不僅能夠節約提取時間,還能顯著增加AME提取得率。
  • 圖  1  低共熔溶劑的篩選

    Figure  1.  Screening of deep eutectic solvents

    圖  2  氯化膽堿:香葉醇摩爾比的篩選

    Figure  2.  Screening of choline chloride:geraniol molar ratio

    圖  3  氯化膽堿:香葉醇含水量的篩選

    Figure  3.  Screening of choline chloride:geraniol water content

    圖  4  氯化膽堿:香葉醇、香葉醇和氯化膽堿的核磁共振譜圖

    Figure  4.  NMR spectra of choline chloride: geraniol, geraniol and choline chloride

    注:A為Chcl-Ger的1H-NMR譜;B為Chcl-Ger的 13C-NMR譜;C為香葉醇的1H-NMR譜;D為香葉醇的13C-NMR譜;E為氯化膽堿的1H-NMR譜;F為氯化膽堿的13C-NMR譜。

    圖  5  氯化膽堿、香葉醇及氯化膽堿:香葉醇的紅外光譜圖

    Figure  5.  Choline chloride, geraniol and choline chloride:geraniol spectra of geraniol

    圖  6  氯化膽堿:香葉醇的熱重分析圖

    Figure  6.  Thermogravimetric analysis diagram of choline chloride:geraniol

    圖  7  單因素實驗

    Figure  7.  Single factor experiments

    圖  8  響應面分析因素間相互作用對AME提取得率的影響的3D曲線圖

    Figure  8.  3D graph of response surface analysis factor inter-action interaction on AME extraction rate

    圖  9  HPLC色譜圖

    Figure  9.  HPLC chromatogram

    注:A為江南卷柏提取物;B為AME標準品;C為Chcl-Ger低共熔溶劑。

    圖  10  不同方法對江南卷柏中AME提取得率的影響

    Figure  10.  Influence of different methods on the content of AME in Selaginella moellendorffii

    表  1  不同類型的DES溶劑

    Table  1.   Different types of DES solvents

    DES溶劑氫鍵受體(HBA)氫鍵供體(HBD)摩爾比
    DES(Chcl-Lin)氯化膽堿(Choline chloride)芳樟醇(Linalool)1:2
    DES(Chcl-Ger)氯化膽堿(Choline chloride)香葉醇(Geraniol)1:2
    DES(Chcl-Alp)氯化膽堿(Choline chloride)α-松油醇(Alpha-Terpineol)1:2
    下載: 導出CSV

    表  2  DES溶劑的篩選

    Table  2.   Screening of DES solvents

    序號DES溶劑HBA:HBD摩爾比(mol)含水量(%)
    1Chcl-Lin、Chcl-Ger、Chcl-Alp1:220
    2Chcl-Ger1:1、1:2、1:3、1:4、1:520
    3Chcl-Ger1:210、20、30、40、50
    下載: 導出CSV

    表  3  響應面試驗因素水平設計

    Table  3.   Response surface experimental factor level design

    水平
    因素
    A:超聲功率(W)B:液固比(mL/g)C:超聲時間(min)
    ?1200510
    02401030
    12801550
    下載: 導出CSV

    表  4  Box-Behnken試驗結果

    Table  4.   Box-Behnken experimental results

    實驗號A液固比(mL/g)B超聲時間(min)C超聲功率(W)Y1黃酮提取得率(mg/g)
    110302402.85
    25302801.46
    310502801.85
    415102401.43
    515302801.72
    65302001.38
    710302402.84
    810102001.45
    95502401.42
    1010302402.86
    1115502401.46
    1210302402.87
    1315302001.46
    1410502001.33
    1510102801.44
    165102401.27
    1710302402.93
    下載: 導出CSV

    表  5  Y1方差分析

    Table  5.   Y1 analysis of variance

    方法來源平方和自由度FP顯著性
    模型7.179464.09< 0.0001***
    A-液固比0.0341119.840.003*
    B-超聲時間0.0266115.470.0056*
    C-超聲功率0.0893151.990.0002**
    AB0.003912.280.1752
    AC0.008414.880.063
    BC0.0724142.150.0003**
    A22.3311357.5< 0.0001***
    B22.2511309.58< 0.0001***
    C21.631951.09< 0.0001***
    殘差0.0127
    失擬值0.007732.40.2086
    純誤差0.00434
    總和7.1816
    下載: 導出CSV
    人妻AV无码系列一区二区三区
  • [1] 謝洋, 徐康平, 鄒振興, 等. 卷柏科植物化學成分多樣性研究進展[J]. 中南藥學,2017,15(2):129?142. [XIE Y, XU K P, ZOU Z X, et al. Advances in chemodiversity from Selaginella[J]. Central South Pharmacy,2017,15(2):129?142. doi:  10.7539/j.issn.1672-2981.2017.02.001

    XIE Y, XU K P, ZOU Z X, et al. Advances in chemodiversity from Selaginella[J]. Central South Pharmacy, 2017, 15(2): 129-142. doi:  10.7539/j.issn.1672-2981.2017.02.001
    [2] 張學艷, 楊萍, 陳科力, 等. 江南卷柏的本草考證及化學成分與藥理作用研究進展[J]. 中國藥房,2018,29(14):1992?1998. [ZHANG X Y, YANG P, CHEN K L, et al. Progress in the research and chemical composition and pharmacological role of Selaginella moellendorffii[J]. China Pharmacy,2018,29(14):1992?1998. doi:  10.6039/j.issn.1001-0408.2018.14.27

    ZHANG X Y, YANG P, CHEN K L, et al. Progress in the research and chemical composition and pharmacological role of Selaginella moellendorffii[J]. China Pharmacy, 2018, 29 (14): 1992-1998. doi:  10.6039/j.issn.1001-0408.2018.14.27
    [3] 何薇, 曾祖平, 王永紅. 藥用卷柏的研究概況[J]. 中草藥,2000(12):954?956. [HE W, ZENG Z P, WANG Y H. Research overview of medicinal Selaginella moellendorffii[J]. Chinese Traditional and Herbal Drugs,2000(12):954?956. doi:  10.3321/j.issn:0253-2670.2000.12.039

    HE W, ZENG Z P, WANG Y H. Research overview of medicinal Selaginella moellendorffii[J]. Chinese Traditional and Herbal Drugs, 2000(12): 954-956. doi:  10.3321/j.issn:0253-2670.2000.12.039
    [4] YUAN C, TAN N H, CHEN J J, et al. Bioactive flavones and biflavones from Selaginella moellendorffii Hieron[J]. Fitoterapia,2010,81(4):253?258. doi:  10.1016/j.fitote.2009.09.007
    [5] QU X Y, LI Q J, ZHANG X J, et al. Amentoflavone protects the hematopoietic system of mice against γ-irradiation[J]. Archives of Pharmacal Research,2019:1?9.
    [6] 丁立新, 張楠楠, 張云杰, 等. 桂花中黃酮類物質提取與純化的研究[J]. 黑龍江醫藥科學,2008,31(5):23?24. [DING L X, ZHANG N N, ZHANG Y J, et al. Extraction and purification of flavonoids from Osmanthus fragrans Lour[J]. Heilongjiang Medicine and Pharmacy,2008,31(5):23?24. doi:  10.3969/j.issn.1008-0104.2008.05.015

    DING L X, ZHANG N N, ZHANG Y J, et al. Extraction and purification of flavonoids from Osmanthus fragrans Lour[J]. Heilongjiang Medicine and Pharmacy, 2008, 31 (5): 23-24. doi:  10.3969/j.issn.1008-0104.2008.05.015
    [7] 向蓉, 何立美, 陳文露, 等. 辣蓼總黃酮提取工藝篩選及優化[J]. 中國獸藥雜志,2019,53(2):40?47. [XIANG R, HE L M, CHEN W L, et al. Screening and optimization of extraction of flavonoids from Polygonum hydropiper[J]. Chinese Journal of Veterinary Drug,2019,53(2):40?47.

    XIANG R, HE L M, CHEN W L, et al. Screening and optimization of extraction of flavonoids from Polygonum hydropiper [J]. Chinese Journal of Veterinary Drug, 2019, 53 (2): 40-47.
    [8] 周海玉, 趙春艷, 孫佩, 等. 變異白色紅花總黃酮提取工藝研究[J]. 成都中醫藥大學學報,2015,38(3):27?31. [ZHOU H Y, ZHAO C Y, SUN P, et al. Study on extraction technology of total flavones from white safflower variety[J]. Journal of Chengdu University of Traditional Chinese Medicine,2015,38(3):27?31.

    ZHOU H Y, ZHAO C Y, SUN P, et al. Study on extraction technology of total flavones from white safflower variety[J]. Journal of Chengdu University of Traditional Chinese Medicine, 2015, 38 (3): 27-31.
    [9] 宗春燕, 蘇學軍, 梁雅娟. 超聲浸漬法提取木蝴蝶中總黃酮的工藝研究[J]. 化學工程師,2019,33(2):18?20. [ZONG C Y, SU X J, LIANG Y J. Study on the extraction of total flavonoids from Oroxylum indicum by ultrasonic immersing method[J]. Chemical Engineer,2019,33(2):18?20.

    ZONG C Y, SU X J, LIANG Y J. Study on the extraction of total flavonoids from Oroxylum indicum by ultrasonic immersing method[J]. Chemical Engineer, 2019, 33 (2): 18-20.
    [10] ABBOTT A P, CAPPER G, DAVIES D L, et al. Preparation of novel, moisture-stable, lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains[J]. Chemical Communications,2001(19):2010?2011. doi:  10.1039/b106357j
    [11] TIPALE M R, KHILLARE L D, DESHMUKH A R, et al. An efficient four component domino synthesis of pyrazolopyranopyrimidines using recyclable choline chloride: Urea deep eutectic solvent[J]. Journal of Heterocyclic Chemistry,2018,55(3):716?728. doi:  10.1002/jhet.3095
    [12] 張盈盈, 陸小華, 馮新, 等. 膽堿類低共熔溶劑的物性及應用[J]. 化學進展,2013,25(6):881?892. [ZHANG Y Y, LU X H, FENG X, et al. Properties and applications of choline-based deep eutectic solvents[J]. Progress in Chemistry,2013,25(6):881?892.

    ZHANG Y Y, LU X H, FENG X, et al. Properties and applications of choline-based deep eutectic solvents[J]. Progress in Chemistry, 2013, 25 (6): 881-892.
    [13] 王靜文. 離子液體及其類似物在二氧化碳捕集中的設計與篩選[D]. 上海: 華東理工大學, 2020: 13-15.

    WANG J W. Design and screening of ionic liquids and analogues as absorbents for carbon dioxide capture[D]. Shanghai: East China University of Science and Technology, 2020: 13-15.
    [14] 吳昊, 宗志敏, 石金龍. 超聲波協同酶法提取銀杏黃酮的工藝研究[J]. 中國資源綜合利用,2012,30(11):26?29. [WU H, ZONG Z M, SHI J L. Study on the extraction of total flavonoids from ginkgo biloba by ultrasonic wave and enzymatic[J]. Chinese Resources Comprehensive Utilization,2012,30(11):26?29. doi:  10.3969/j.issn.1008-9500.2012.11.013

    WU H, ZONG Z M, SHI J L. Study on the extraction of total flavonoids from Ginkgo Biloba by ultrasonic wave and enzymatic[J] . Chinese resources comprehensive utilization, 2012, 30 (11): 26-29. doi:  10.3969/j.issn.1008-9500.2012.11.013
    [15] 蔣海英. 基于低共熔溶劑的固體電解質制備及其應用研究[D]. 陜西: 西安理工大學, 2019.

    JIANG H Y. Preparation and application of solid polymer electrolyte based on deep eutectic solvent[D]. Shaanxi: Xi'an University of Technology, 2019.
    [16] 羅通. 基于低共熔溶劑(DES)體系的木質素納米顆粒制備及其應用研究[D]. 濟南: 齊魯工業大學, 2021.

    LUO T. Preparation and application of lignin nanoparticles based on deep eutectic solvent (DES) system [D]. Jinan: Qilu University of Technology, 2021.
    [17] 秦晶晶, 錢慧琴, 趙媛, 等. 菟絲子總黃酮不同提取方法比較[J]. 安徽農業科學,2017,45(34):114?116. [QIN J J, QIAN H C, ZHAO Y, et al. Comparison of different extraction methods of total flavonoids in Cuscuta chinesis[J]. Journal of Anhui Agricultural Sciences,2017,45(34):114?116. doi:  10.3969/j.issn.0517-6611.2017.34.036

    QIN J J, QIAN H C, ZHAO Y, et al. Comparison of Different Extraction Methods of Total Flavonoids in Cuscuta chinesis[J]. Journal of Anhui Agricultural Sciences, 2017, 45(34): 114-116. doi:  10.3969/j.issn.0517-6611.2017.34.036
    [18] 韓秋菊, 徐慕儒. 2種蜂膠總黃酮提取方法的比較[J]. 安徽農業科學,2011,39(15):9133?9134. [HAN Q J, XU M R. Comparison of two extraction methods of flavonoids from propolis[J]. Journal of Anhui Agricultural Sciences,2011,39(15):9133?9134. doi:  10.3969/j.issn.0517-6611.2011.15.115

    HAN Q J, XU M R. Comparison of two extraction methods of flavonoids from propolis[J]. Journal of Anhui Agricultural Sciences, 2011, 39(15): 9133-9134. doi:  10.3969/j.issn.0517-6611.2011.15.115
    [19] 李洪玉, 陶正升, 于瑞峰, 等. 銀杏葉黃酮成分聚酰胺薄層色譜鑒別方法研究[J]. 中國現代藥物應用,2018,12(8):214?217. [LI H Y, TAO Z L, YU R F, et al. Study on the identification method of thin layer chromatographic polyamide in ginkgo leaf flavonoid[J]. Chinese Journal of Modern Drug Application,2018,12(8):214?217.

    LI H Y, TAO Z L, YU R F, et al. Study on the identification method of thin layer chromatographic polyamide in ginkgo leaf flavonoid [J]. Chinese Journal of Modern Drug Application, 2018, 12(8): 214-217.
    [20] 李國峰, 陳海芳, 杜文迪, 等. 超聲輔助離子液體提取柚子皮總黃酮及其抗氧化研究[J]. 江西中醫藥大學學報,2021,33(1):84?88. [LI G F, CHEN H F, DU W D, et al. Ultrasonic assisted lonic liquid extraction of total flavonoids from pomelo peel and their antioxidant activities[J]. Journal of Jiangxi University of Chinese Medicine,2021,33(1):84?88.

    LI G F, CHEN H F, DU W D, et al. Ultrasonic assisted lonic liquid extraction of total flavonoids from pomelo peel and their antioxidant activities[J]. Journal of Jiangxi University of Chinese Medicine, 2021, 33 (1): 84-88.
    [21] 侯玉翠, 王震, 任樹行, 等. 低共熔溶劑在混合物分離中的應用[J]. 科學通報,2015,60(26):2490?2499. [HOU Y C, WANG Z, REN S H, et al. The applications of deep eutectic solvents in the separation of mixtures[J]. Chinese Science Bulletin,2015,60(26):2490?2499. doi:  10.1360/N972015-00385

    HOU Y C, WANG Z, REN S H, et al. The applications of deep eutectic solvents in the separation of mixtures[J]. Chinese Science Bulletin, 2015, 60(26): 2490-2499. doi:  10.1360/N972015-00385
    [22] 韋露, 樊友軍. 低共熔溶劑及其應用研究進展[J]. 化學通報,2011,74(4):333?339. [WEI L, FAN Y J. Progress of deep eutectic solvents and their applications[J]. Chinese Science Bulletin,2011,74(4):333?339.

    WEI L, FAN Y J. Progress of deep eutectic solvents and their applications[J]. Chinese Science Bulletin, 2011, 74(4): 333-339.
    [23] 王慧. 低共熔溶劑在黃芩有效成分提取及制備中的應用研究[D]. 太原: 山西大學, 2019.

    WANG H. Application of deep eutectic solvents in extraction and preparation of active ingredient of Scutellaria baicalensis Georgi[D]. Taiyuan: Shanxi University, 2019.
    [24] 都宏霞, 繆領珍, 胡梓恒, 等. 低共熔溶劑提取桂花黃酮的工藝優化[J]. 現代食品科技,2021,37(5):203?211. [DU H X, MIAO L Z, HU Z H, et al. Optimizing the extraction of flavonoids from Osmanthus fragrans using deep eutectic solvents[J]. Modern Food Science and Technology,2021,37(5):203?211.

    DU H X, MIAO L Z, HU Z H, et al. Optimizing the extraction of flavonoids from osmanthus fragrans using deep eutectic solvents[J]. Modern Food Science and Technology, 2021, 37 (5): 203-211.
    [25] 孫平, 董萍萍, 董丹華, 等. 超聲波輔助低共熔溶劑提取野菊花總黃酮的工藝研究[J]. 食品工業科技,2020,41(20):147?152. [SUN P, DONG P P, DONG D H, et al. UItrasound-assisted deep eutectic solvent extraction of total flavonoids from Chrysanthemum indicum[J]. Science and Technology of Food Industry,2020,41(20):147?152.

    SUN P, DONG P P, DONG D H, et al. UItrasound-assisted deep eutectic solvent extraction of total flavonoids from Chrysanthemum indicum[J]. Science and Technology of Food Industry, 2020, 41 (20): 147-152.
  • 加載中
圖(10) / 表(5)
計量
  • 文章訪問數:  18
  • HTML全文瀏覽量:  5
  • PDF下載量:  7
  • 被引次數: 0
出版歷程
  • 收稿日期:  2021-10-18
  • 網絡出版日期:  2022-08-11
  • 刊出日期:  2022-08-11

目錄

    /

    返回文章
    返回

    重要通知

    專欄綠色通道:食品營養素包埋與遞送