木槿花生物活性物质及其抗氧化活性分析
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摘要
研究5种木槿花卉及其不同极性溶剂萃取物的生物活性物质含量和抗氧化活性,分析它们之间的相关性,并采用高效液相色谱-串联质谱鉴定其中的活性物质成分,以期为木槿深加工及其品种选育提供理论依据。5个品种木槿花的总酚和总黄酮含量从高到低依次为木槿原种、粉紫重瓣木槿花、薰衣草薄绸木槿花、紫玉和雅致木槿,各品种木槿花的抗氧化活性排序与其总酚和总黄酮含量排序基本一致,其中木槿原种的总酚和总黄酮含量最高,分别达到了17.33 mg/g和12.68 mg/g,且抗氧化活性最强,其总还原能力、1,1-二苯基-2-三硝基苯肼(1,1-diphenyl-2-picrylhydrazyl,DPPH)自由基清除能力、2,2’-联氨-双-3-乙基苯并噻唑啉-6-磺酸(2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid),ABTS)自由基清除能力分别为1.58 mmol/g和6.82、17.96 mg/g。木槿花的抗氧化活性与其总酚和总黄酮含量间有极显著的相关性(P<0.01),与花青素含量相关性不显著(P>0.05)。木槿原种不同极性溶剂萃取物均具有一定的抗氧化活性,其中正丁醇的总还原能力(6.16 mmol/g)最高,且对DPPH自由基(15.50 mg/g)和ABTS自由基(40.71 mg/g)清除效果最好。从木槿原种正丁醇萃取物中初步鉴定出8种抗氧化物质,分别为山柰酚-O-六碳糖-C-六碳糖苷、芹菜素、山柰酚-O-六碳糖-C-六碳糖苷同分异构体、芹菜素-C-二糖苷、芹菜素-葡萄糖芹糖苷、山柰酚-3-O-芸香糖苷、芹菜素-7-O-芸香糖苷、矢车菊素-3-丙二酰葡萄糖苷。
This study aimed to investigate and correlate the bioactive components and antioxidant activity of flowers from five varieties of Hibiscus syriacus and different polar solvent extracts from Hibiscus syriacus L. for the purpose of providing a theoretical basis for deep processing and breed of hibiscus flower. The bioactive components were identified by high performance liquid chromatography-tandem mass spectrometry(HPLC-MS/MS). The results showed that the contents of total polyphenols and total flavonoids in five varieties of Hibiscus syriacus were consistently in the decreasing order of Hibiscus syriacus L., Hibiscus syriacus f. paeoniflorus, Hibiscus syriacus cv. Lavandula Chiffon, Hibiscus syriacus cv. Shigyoku and Hibiscus syriacus f. elegantissimus. A similar order was observed in the antioxidant activity. The contents of polyphenols and total flavonoids in the flower of Hibiscus syriacus L. were the highest, which were 17.33 and12.68 mg/g, respectively, and it had the strongest antioxidant activity with ferric ion reducing antioxidant power(FRAP),1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging capacity, and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt(ABTS) radical scavenging capacity of 1.58 mmol/g, 6.82 and 17.96 mg/g, respectively. There was a significant correlation between the antioxidant activity and the contents of total polyphenols and total flavonoids(P < 0.01), but the correlation with anthocyanin content was not significant(P > 0.05). All solvent extracts from Hibiscus syriacus L. had antioxidant activity. The highest total reducing power(6.16 mmol/g) was observed in the n-butanol extract,accompanied by the strongest DPPH radical(15.50 mg/g) and ABTS radical scavenging capacity(40.71 mg/g). Eight compounds from the n-butanol extract were identified including kaempferol-O-hexose-C-glucoside, apigenin, kaempferol-Ohexose-C-hexose glycoside isomers, apigenin-C-diglycoside, apigenin-glycoside glucoside, behenylphenol-3-O-rutinoside,apigenin-7-O-rutinoside, and cyanidin-3-malonyl glucoside.
This study aimed to investigate and correlate the bioactive components and antioxidant activity of flowers from five varieties of Hibiscus syriacus and different polar solvent extracts from Hibiscus syriacus L. for the purpose of providing a theoretical basis for deep processing and breed of hibiscus flower. The bioactive components were identified by high performance liquid chromatography-tandem mass spectrometry(HPLC-MS/MS). The results showed that the contents of total polyphenols and total flavonoids in five varieties of Hibiscus syriacus were consistently in the decreasing order of Hibiscus syriacus L., Hibiscus syriacus f. paeoniflorus, Hibiscus syriacus cv. Lavandula Chiffon, Hibiscus syriacus cv. Shigyoku and Hibiscus syriacus f. elegantissimus. A similar order was observed in the antioxidant activity. The contents of polyphenols and total flavonoids in the flower of Hibiscus syriacus L. were the highest, which were 17.33 and12.68 mg/g, respectively, and it had the strongest antioxidant activity with ferric ion reducing antioxidant power(FRAP),1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging capacity, and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt(ABTS) radical scavenging capacity of 1.58 mmol/g, 6.82 and 17.96 mg/g, respectively. There was a significant correlation between the antioxidant activity and the contents of total polyphenols and total flavonoids(P < 0.01), but the correlation with anthocyanin content was not significant(P > 0.05). All solvent extracts from Hibiscus syriacus L. had antioxidant activity. The highest total reducing power(6.16 mmol/g) was observed in the n-butanol extract,accompanied by the strongest DPPH radical(15.50 mg/g) and ABTS radical scavenging capacity(40.71 mg/g). Eight compounds from the n-butanol extract were identified including kaempferol-O-hexose-C-glucoside, apigenin, kaempferol-Ohexose-C-hexose glycoside isomers, apigenin-C-diglycoside, apigenin-glycoside glucoside, behenylphenol-3-O-rutinoside,apigenin-7-O-rutinoside, and cyanidin-3-malonyl glucoside.
引文
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[18]张超,陈光,李彦慧.二乔玉兰开花过程中花色变化的生理生化机制[J].西北植物学报,2012,32(4):716-721.DOI:10.3969/j.issn.1000-4025.2012.04.013.
[19]徐颖,樊明涛,冉军舰,等.不同品种苹果籽总酚含量与抗氧化相关性研究[J].食品科学,2015,36(1):79-83.DOI:10.7506/spkx1002-6630-201501015.
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[22]SOCHA R,JUSZCZAK L,PIETRZYK S,et al.Antioxidant activity and phenolic composition of herbhoneys[J].Food Chemistry,2009,113(2):568-574.DOI:10.1016/j.foodchem.2008.08.029.
[23]石雪萍,吴亮亮,高鹏,等.20种食用辛香料抗氧化性及其与黄酮和多酚的相关性研究[J].食品科学,2011,32(5):83-86.
[24]邵佩兰,徐明,郭晓丹,等.红枣色素中活性成分含量与抗氧化活性的相关性[J].食品工业科技,2016,37(17):171-174.
[25]张东京,高贵珍,张兴桃.不同极性梨多酚抗氧化性能的研究[J].食品与机械,2016,32(10):164-167.
[26]郑梦娇.扶桑叶黄酮提取纯化及抗氧化活性研究[D].福州:福建农林大学,2013:40-49.
[27]舒俊生,黄桂东,毛健.滁菊95%乙醇提取液中黄酮类和酚酸类物质的鉴定及分离[J].中国食品学报,2013,13(4):207-213.
[28]孙嘏.撑篙竹(Bambusa pervariabilis McClure)竹叶化学成分及其生物活性的研究[D].北京:中国林业科学研究院,2010:153-154.
[29]陈慧,盛丹丹,王文君.黄金茶醇提取物成分及抗氧化活性的研究[J].现代食品科技,2017,33(1):26-32.
[30]潘瑶,郑时莲,邹兴平,等.葡萄、芒果、草莓乙醇提取物抗氧化活性组分分析及其抗氧化相互作用[J].食品科学,2017,38(4):133-140.DOI:10.7506/spkx1002-6630-201704022.
[2]张文彦,王晓红,李安平,等.木槿功能性营养成分与生物活性研究进展[J].食品与机械,2017,33(2):216-219.
[3]景立新,郑丛龙,林柏全,等.木槿花中营养成分研究[J].食品研究与开发,2009,30(6):146-148.DOI:10.3969/j.issn.1005-6521.2009.06.044.
[4]BANDYUKOVA V A,LIGAI L V.Chemical study of the composition of the polyphenolic compounds of Hibiscus syriacus[J].Chemistry of Natural Compounds,1990,26(4):470-471.DOI:10.1007/BF00599016.
[5]蒋新龙,蒋益花.木槿花花叶总黄酮的提取工艺和含量测定[J].食品科技,2007,32(1):88-91.DOI:10.3969/j.issn.1005-9989.2007.01.025.
[6]RAKESH P,SUJIT P,JANESHWER Y.Isolation and identification of compounds from the leaves extract of Hibiscus syriacus L.[J].Asian Journal of Pharmacy and Technology,2015,5(1):8-12.DOI:10.5958/2231-5713.2015.00002.1.
[7]CHENG Y L,LEE S C,HARN H J,et al.The extract of Hibiscus syriacus inducing apoptosis by activating p53 and AIF in human lung cancer cells[J].American Journal of Chinese Medicine,2008,36(1):171-184.DOI:10.1142/S0192415X08005680.
[8]HSU R J,HSU Y C,CHEN S P,et al.The triterpenoids of Hibiscus syriacus induce apoptosis and inhibit cell migration in breast cancer cells[J].BMC Complementary and Alternative Medicine,2015,15(1):65-73.DOI:10.1186/s12906-015-0592-9.
[9]张福娣,游纪萍,陈新香,等.扶桑花色素的抗氧化作用研究[J].中国食品学报,2010,10(6):72-76.DOI:10.16429/j.1009-7848.2010.06.033.
[10]李晓英,薛梅,樊汶樵.蓝莓花、茎、叶酚类物质含量及抗氧化活性比较[J].食品科学,2017,38(3):142-147.DOI:10.7506/spkx1002-6630-201703024.
[11]MARIALEONORALOTISD F,AVV R.Total phenolics and antioxidant capacity of heat-treated peanut skins[J].Journal of Food Composition and Analysis,2009,22(1):16-24.DOI:10.1016/j.jfca.2008.05.012.
[12]刘香萍,王国庆,李国良,等.响应面法优化提取紫花苜蓿叶总黄酮及其抗氧化活性研究[J].中国食品学报,2016,16(4):145-152.
[13]杨兆艳.pH示差法测定桑椹红色素中花青素含量的研究[J].食品科技,2007,32(4):201-203.DOI:10.3969/j.issn.1005-9989.2007.04.060.
[14]郑时莲,邓泽元,蒋海伟,等.茄子皮中花色苷提取方法的比较及其抗氧化活性研究[J].中国食品学报,2017,17(1):92-99.
[15]MOON J K,SHIBAMOTO T.Antioxidant assays for plant and food components[J].Journal of Agricultural and Food Chemistry,2009,57(5):1655-1666.DOI:10.1021/jf803537k.
[16]BENZIE I F F,STRAIN J J.The ferric reducing ability of plasma(FRAP)as a measure of“antioxidant power”:the FRAP assay[J].Analytical Biochemistry,1996,239(1):70-76.DOI:10.1006/abio.1996.0292.
[17]RE R,PELLEGRINI N,PROTEGGENTE A,et al.Antioxidant activity applying an improved ABTS radical cation decolorization assay[J].Free Radical Biology and Medicine,1999,26(9/10):1231-1237.DOI:10.1016/S0891-5849(98)00315-3.
[18]张超,陈光,李彦慧.二乔玉兰开花过程中花色变化的生理生化机制[J].西北植物学报,2012,32(4):716-721.DOI:10.3969/j.issn.1000-4025.2012.04.013.
[19]徐颖,樊明涛,冉军舰,等.不同品种苹果籽总酚含量与抗氧化相关性研究[J].食品科学,2015,36(1):79-83.DOI:10.7506/spkx1002-6630-201501015.
[20]白周亚,阚丽娇,李昌,等.不同豇豆中酚类含量与抗氧化活性[J].食品科学,2017,38(15):153-157.DOI:10.7506/spkx1002-6630-201715025.
[21]刘禹,段江莲,李为琴,等.高粱米不同溶剂提取物的抗氧化活性研究[J].中国粮油学报,2013,28(6):36-39.DOI:10.3969/j.issn.1003-0174.2013.06.008.
[22]SOCHA R,JUSZCZAK L,PIETRZYK S,et al.Antioxidant activity and phenolic composition of herbhoneys[J].Food Chemistry,2009,113(2):568-574.DOI:10.1016/j.foodchem.2008.08.029.
[23]石雪萍,吴亮亮,高鹏,等.20种食用辛香料抗氧化性及其与黄酮和多酚的相关性研究[J].食品科学,2011,32(5):83-86.
[24]邵佩兰,徐明,郭晓丹,等.红枣色素中活性成分含量与抗氧化活性的相关性[J].食品工业科技,2016,37(17):171-174.
[25]张东京,高贵珍,张兴桃.不同极性梨多酚抗氧化性能的研究[J].食品与机械,2016,32(10):164-167.
[26]郑梦娇.扶桑叶黄酮提取纯化及抗氧化活性研究[D].福州:福建农林大学,2013:40-49.
[27]舒俊生,黄桂东,毛健.滁菊95%乙醇提取液中黄酮类和酚酸类物质的鉴定及分离[J].中国食品学报,2013,13(4):207-213.
[28]孙嘏.撑篙竹(Bambusa pervariabilis McClure)竹叶化学成分及其生物活性的研究[D].北京:中国林业科学研究院,2010:153-154.
[29]陈慧,盛丹丹,王文君.黄金茶醇提取物成分及抗氧化活性的研究[J].现代食品科技,2017,33(1):26-32.
[30]潘瑶,郑时莲,邹兴平,等.葡萄、芒果、草莓乙醇提取物抗氧化活性组分分析及其抗氧化相互作用[J].食品科学,2017,38(4):133-140.DOI:10.7506/spkx1002-6630-201704022.
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