紫茄子皮飞燕草色素苷的分析及其苷元的制备
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摘要
以紫色茄子皮为材料,期望分离纯化得到价格昂贵的高纯度飞燕草色素单体。利用光谱及质谱技术对紫色茄子皮的花青素苷进行了定性分析,鉴定出4种花青素苷,且均为连接不同糖配体的飞燕草色素苷。然后优化飞燕草色素的提取纯化条件,结果表明,提取剂为含1%盐酸的60%乙醇溶液、料液比为1:20时提取效果最佳。利用AB-8型大孔树脂初步纯化飞燕草色素苷,发现随着洗脱剂乙醇浓度的升高,得到的飞燕草色素苷溶液浓度先升高后降低,当乙醇浓度为30%时洗脱效果最好,此时洗脱液在530 nm下的紫外吸收值为0.49。运用高温酸水解的方法可获得飞燕草色素苷元,即飞燕草色素。对酸水解后获得的飞燕草色素苷元依次利用AB-8型大孔树脂和C18柱层析进行分离纯化,得到飞燕草色素单体,最后通过结晶沉淀的方法获得了纯度大于98%的飞燕草色素单体粉末。研究为分离纯化飞燕草色素提供了一种切实可行的方法。
In this work, the low price peel of purple eggplant was used as material to obtain expensive high purification delphinidin monomer. The anthocyanin in purple eggplant peel was qualitatively analyzed by spectrum and mass spectrometry, and 4 delphindins were identified. Then the optimized conditions for extraction delphinidin were investigated. Result showed that optimal extraction solvent was 60%ethanol with 1% hydrochloric acid; ratio of solid to liquid was 1:20. AB-8 macroporous resin which eluted with ethanol was used for initial purification of anthocyanin, the concentration of 30% ethanol elute was the optimal, and the UV absorption value of 530 nm at this concentration was 0.49. Subsequently, the delphinidin glycoside was acid hydrolyzed, and delphinidin aglycone was purified by AB-8 macroporous resin and C-18 resin. Finally, delphinidin powder with purity more than 98% was obtained. It provides a practical method for separating and purifying delphinidin pigments.
In this work, the low price peel of purple eggplant was used as material to obtain expensive high purification delphinidin monomer. The anthocyanin in purple eggplant peel was qualitatively analyzed by spectrum and mass spectrometry, and 4 delphindins were identified. Then the optimized conditions for extraction delphinidin were investigated. Result showed that optimal extraction solvent was 60%ethanol with 1% hydrochloric acid; ratio of solid to liquid was 1:20. AB-8 macroporous resin which eluted with ethanol was used for initial purification of anthocyanin, the concentration of 30% ethanol elute was the optimal, and the UV absorption value of 530 nm at this concentration was 0.49. Subsequently, the delphinidin glycoside was acid hydrolyzed, and delphinidin aglycone was purified by AB-8 macroporous resin and C-18 resin. Finally, delphinidin powder with purity more than 98% was obtained. It provides a practical method for separating and purifying delphinidin pigments.
引文
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[21]Lo Scalzo R,Genna A,Branca F et al.Anthocyanin composition of cauliflower(Brassica oleracea L.var.botrytis)and cabbage(B.oleracea L.var.capitata)and its stability in relation to thermal treatments[J].Food Chemistry,2008,107(1):136-144
[22]Xie D Y,Sharma S B,Paiva N L et al.Role of anthocyanidin reductase,encoded by Banyuls in plant flavonoid biosynthesis[J].Science,2003,299(5605):396-399
[23]Xie D Y,Sharma S B,Dixon R A.Anthocyanidin reductases from Medicago truncatula and Arabidopsis thaliana[J].Arch Biochem Biophys,2004,422(1):91-102
[24]Pang Y,Abeysinghe S,He J,et al.Functional characterization of proanthocyanidin pathway enzymes from tea(Camellia sinensis)and their application for metabolic engineering[J].Plant Physiol,2013,161:1103-1116
[25]吕玲玲,冯雪锋,李威,等.茄子花青素研究进展[J].分子植物育种,2018,16(15):5065-5071LYU Ling-ling,FENG Xue-feng,LI Wei,et al.Research progress of anthocyanin in eggplant[J].Molecular Plant Breeding,2018,16(15):5065-5071
[26]Todaro A,Cimino F,Rapisarda P,et al.Recovery of anthocyanins from eggplant peel[J].Food Chemistry,2009,114(2):434-439
[27]Tateyama C,Igarashi K.Anthocyanin and chlorogenic acid contents of some selected eggplant(Solanam melongena L.)cultivars,and the radical scavenging activities of their extracts[J].Journal of the Japanese Society for Food Science and Technology-Nippon Shokuhin Kagaku Kogaku Kaishi,2006,53(4):218-224
[28]Li J,Ren L,Gao Z,et al.Combined transcriptomic and proteomic analysis constructs anew model for light-induced anthocyanin biosynthesis in eggplant(Solanum Melongena L.)[J].Plant Cell and Environment,2017,40(12):3069-3087
[29]Li J,He Y J,Zhou L,et al.Transcriptome profiling of genes related to light-induced anthocyanin biosynthesis in eggplant(Solanum Melongena L.)before purple color becomes evident[J].Bmc Genomics,2018,19,201-212
[30]Jiang M M,Ren L,Lian H L,et al.Novel insight into the mechanism underlying light-controlled anthocyanin accumulation in eggplant(Solanum melongena L.)[J].Plant Science,2016,249:46-58
[31]宋会歌,刘美艳,董楠,等.食品中花色苷降解机制研究进展[J].食品科学,2011,32(13):355-359SONG Hui-ge,LIU Mei-yan,DONG Nan,et al.Research progress on degradation mechanisms of anthocyanins in foods[J].Food Science,2011,32(13):355-359
[2]Jimenez C D,Flores C S,He J et al.Characterisation and preliminary bioactivity determination of Berberis boliviana Lechler fruit anthocyanins[J].Food Chemistry,2011,128(3):717-724
[3]Pradhan PC,Saha S.Anthocyanin profiling of Berberis lycium Royle berry and its bioactivity evaluation for its nutraceutical potential[J].Journal of Food Science and Technology-Mysore,2016,53(2):1205-1213
[4]Teng H,Fang T,Lin QY et al.Red raspberry and its anthocyanins:Bioactivity beyond antioxidant capacity[J].Trends in Food Science&Technology,2017,66:153-165
[5]Wu XL,Prior RL.Identification and characterization of anthocyanins by high-performance liquid chromatographyelectrospray ionization-tandem mass spectrometry in common foods in the united states:Vegetables,nuts,and grains[J].Journal of Agricultural and Food Chemistry,2005,53(8):3101-3113
[6]杨秀娟,赵晓燕,马越,等.花青素研究进展[J].中国食品添加剂,2005,4:40-42,17YANG Xiu-juan,ZHAO Xiao-yan,MA yue,et al.The advancement of anthocyanins[J].China Food Additives,2005,4:40-42,17
[7]孙建霞,张燕,胡小松,等.花青素的提取,分离以及纯化方法研究进展[J].食品与发酵工业,2008,8:111-117SUN Jian-xia,ZHANG Yan,HU Xiao-song,et al.Review on the methods of extraction,isolation andpurification of anthocyanins[J].Food And Fermentation Industries,2008,8:111-117
[8]李娟娟.花青素研究进展[J].中山大学研究生学刊(自然科学,医学版),2007,2:1-5LI Juan-juan.The advancement of anthocyanins[J].Journal of the Graduates Sun Yat-Sen University(Natural Sciences,Medi cinem),2007,2:1-5
[9]Li J,Li XD,Zhang Y,et al.Identification and thermal stability of purple-fleshed sweet potato anthocyanins in aqueous solutions with various pH values and fruit juices[J].Food Chemistry,2013,136(3-4):1429-1434
[10]He Q,Zhang Z F,Zhang L G.Anthocyanin accumulation,antioxidant ability and stability,and a transcriptional analysis of anthocyanin biosynthesis in purple heading Chinese cabbage(Brassica rapa L.ssp pekinensis)[J].Journal of Agricultural and Food Chemistry,2016,64(1):132-145
[11]Miguel M G,Dandlen S,Neves M A.Role of anthocyanins in the antioxidant ability of pomegranate[J].Agro Food Industry Hi-Tech,2007,18(6):48-50
[12]Mc Dougall G J,Fyffe S,Dobson P et al.Anthocyanins from red cabbage-stability to simulated gastrointestinal digestion[J].Phytochemistry,2007,68(9):1285-1294
[13]Noda Y,Kneyuki T,Igarashi K et al.Antioxidant activity of nasunin,an anthocyanin in eggplant peels[J].Toxicology,2000,148(2-3):119-123
[14]Matsubara K,Kaneyuki T,Miyake T,et al.Antiangiogenic activity of nasunin,an antioxidant anthocyanin,in eggplant peels[J].Journal of Agricultural and Food Chemistry,2005,53(16):6272-6275
[15]Sankhari J M,Thounaojam M C,Jadeja R N,et al.Anthocyanin-rich red cabbage(Brassica oleracea L.)extract attenuates cardiac and hepatic oxidative stress in rats fed an atherogenic diet[J].Journal of the Science of Food and Agriculture,2012,92(8):1688-1693
[16]Kolodziejczyk J,Saluk-Juszczak J,Posmyk MM,et al.Red cabbage anthocyanins may protect blood plasma proteins and lipids[J].Central European Journal of Biology,2011,6(4):565-574
[17]Sadilova E,Stintzing F C,Carle R.Anthocyanins,colour and antioxidant properties of eggplant(Solanum melongena L.)and violet pepper(Capsicum annuum L.)peel extracts[J].Zeitschrift Fur Naturforschung C-a Journal of Biosciences,2006,61(7-8):527-535
[18]张昊琛,张文佳,孙汉巨.一种黑米花青素的提取纯化方法:中国专利CN102766125A[P]2012-11-07.http://dbpub.cnki.net ZHANG Hao-chen,ZHANG Wen-jia,SUN Han-ju.Extraction and Purification Method of One Black Rice Anthocyanin:Chinese Patent CN 102766125A[P]2012-11-07.http://dbpub.cnki.net
[19]Dranca F,Oroian M.Optimization of ultrasound-assisted extraction of total monomeric anthocyanin(TMA)and total phenolic content(TPC)from eggplant(Solanum melongena L.)peel[J].Ultrasonics Sonochemistry,2016,31:637-646
[20]朱振宝,吴园芳,易建华.紫甘蓝花色苷的分离纯化[J].食品科技,2012,6:239-243ZHU Zhen-bao,WU Yuan-fang,YI Jian-hua.Purification of purple cabbage anthocyains[J].Food Science and Technology,2012,6:239-243
[21]Lo Scalzo R,Genna A,Branca F et al.Anthocyanin composition of cauliflower(Brassica oleracea L.var.botrytis)and cabbage(B.oleracea L.var.capitata)and its stability in relation to thermal treatments[J].Food Chemistry,2008,107(1):136-144
[22]Xie D Y,Sharma S B,Paiva N L et al.Role of anthocyanidin reductase,encoded by Banyuls in plant flavonoid biosynthesis[J].Science,2003,299(5605):396-399
[23]Xie D Y,Sharma S B,Dixon R A.Anthocyanidin reductases from Medicago truncatula and Arabidopsis thaliana[J].Arch Biochem Biophys,2004,422(1):91-102
[24]Pang Y,Abeysinghe S,He J,et al.Functional characterization of proanthocyanidin pathway enzymes from tea(Camellia sinensis)and their application for metabolic engineering[J].Plant Physiol,2013,161:1103-1116
[25]吕玲玲,冯雪锋,李威,等.茄子花青素研究进展[J].分子植物育种,2018,16(15):5065-5071LYU Ling-ling,FENG Xue-feng,LI Wei,et al.Research progress of anthocyanin in eggplant[J].Molecular Plant Breeding,2018,16(15):5065-5071
[26]Todaro A,Cimino F,Rapisarda P,et al.Recovery of anthocyanins from eggplant peel[J].Food Chemistry,2009,114(2):434-439
[27]Tateyama C,Igarashi K.Anthocyanin and chlorogenic acid contents of some selected eggplant(Solanam melongena L.)cultivars,and the radical scavenging activities of their extracts[J].Journal of the Japanese Society for Food Science and Technology-Nippon Shokuhin Kagaku Kogaku Kaishi,2006,53(4):218-224
[28]Li J,Ren L,Gao Z,et al.Combined transcriptomic and proteomic analysis constructs anew model for light-induced anthocyanin biosynthesis in eggplant(Solanum Melongena L.)[J].Plant Cell and Environment,2017,40(12):3069-3087
[29]Li J,He Y J,Zhou L,et al.Transcriptome profiling of genes related to light-induced anthocyanin biosynthesis in eggplant(Solanum Melongena L.)before purple color becomes evident[J].Bmc Genomics,2018,19,201-212
[30]Jiang M M,Ren L,Lian H L,et al.Novel insight into the mechanism underlying light-controlled anthocyanin accumulation in eggplant(Solanum melongena L.)[J].Plant Science,2016,249:46-58
[31]宋会歌,刘美艳,董楠,等.食品中花色苷降解机制研究进展[J].食品科学,2011,32(13):355-359SONG Hui-ge,LIU Mei-yan,DONG Nan,et al.Research progress on degradation mechanisms of anthocyanins in foods[J].Food Science,2011,32(13):355-359