发酵法制水溶性姜黄素
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摘要
姜黄素是一种具有广泛生物活性以及医用价值的多酚类化合物,较差的水溶性和较低的生物利用度限制了其应用,糖苷化是提高其水溶性的有效手段。研究通过变色圈法筛选到1株产β-葡萄糖苷酶的益生菌,并对其进行菌落形态分析和16S r DNA测序,确定为玉米乳杆菌(Lactobacillus zeae strain OZK17)。该菌能够有效利用糖苷水解酶的逆反应对姜黄素分子进行糖基化修饰,形成姜黄素葡萄糖苷和姜黄素双葡萄糖苷,利用高效液相色谱(HPLC)和高效液相色谱-质谱联合(LC-MS)对糖苷化产物进行了确认。其中姜黄素葡萄糖苷转化率为40%,姜黄素双葡萄糖苷转化率为4%。
Curcumin is a polyphenolic compound with broad biological activities and medical values. However,poor water solubility and low bioavailability limit its application. Glycosylation is an effective way to improve its water solubility. A β-glucosidase-producing probiotic was screened by discoloration circle. The strain was identified as Lactobacillus zeae strain OZK17 by colony morphology and 16 S r DNA sequencing. This strain could effectively utilize the reverse reaction of glycoside hydrolase to glycosylate curcumin molecules to form curcumin glucosides and curcumin diglucosides,which were confirmed by HPLC and LC-MS. The conversion rates of curcumin glucosides and the curcumin diglucosides were 40% and 4%,respectively. This study provides a new reference for fuller and more effective applications of curcumin in foods and medicines.
Curcumin is a polyphenolic compound with broad biological activities and medical values. However,poor water solubility and low bioavailability limit its application. Glycosylation is an effective way to improve its water solubility. A β-glucosidase-producing probiotic was screened by discoloration circle. The strain was identified as Lactobacillus zeae strain OZK17 by colony morphology and 16 S r DNA sequencing. This strain could effectively utilize the reverse reaction of glycoside hydrolase to glycosylate curcumin molecules to form curcumin glucosides and curcumin diglucosides,which were confirmed by HPLC and LC-MS. The conversion rates of curcumin glucosides and the curcumin diglucosides were 40% and 4%,respectively. This study provides a new reference for fuller and more effective applications of curcumin in foods and medicines.
引文
[1]李锐,刘芳,李芸香,等.微生物转化法制备双脱甲氧基姜黄素糖苷化产物及其对Hep G2肿瘤细胞的抑制作用[J].食品与发酵工业,2016,42(6):20-25.
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[13]魏妍婷,马三梅.姜黄素衍生物及复合物抗肿瘤的研究[J].生命科学,2017,29(4):386-392.
[14]伍敏晖,王磊,何梅.高压微射流均质对姜黄素纳米乳液稳定性的影响[J].中国食品学报,2018,18(5):56-62.
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[16]陈建平,彭莞仪,秦小明,等.姜黄素超分子包合物的结构鉴定及其抗氧化活性[J].食品工业科技,2017(21):28-32.
[17] SAFAVY A,RAISCH P,MANTENA S,et al. Design and development of water-soluble curcumin conjugates as potential anticancer agents[J]. Journal of Medicinal Chemistry,2007,50(24):6 284-6 288.
[18] KAMINAGA Y,NAGATSU A,AKIYAMA T,et al. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus[J]. FEBS Letters,2003,555(2):311-316.
[19]孟岚,吴旭日,陈依军.糖苷合成酶及应用的研究进展[J].广西科学,2017,24(1):7-14.
[20] CHOUDHURY A K,RAJA S,MAHAPATRA S,et al.Synthesis and evaluation of the anti-oxidant capacity of curcumin glucuronides,the major curcumin metabolites[J]. Antioxidants,2015,4(4):750-767.
[21] ZHANG Xing,LI Min,LI Rui,et al. Microbial transformation of curcumin by Rhizopus chinensis[J]. Biocatalysis,2015,28(5-6):380-386.
[22] PRASAD E,HAMEEDA B,RAO A B,et al. Biotransformation of curcumin for improved biological activity and antiproliferative activity on acute HT-29 human cell lines[J]. Indian Journal of Biotechnology,2014,13(3):324-329.
[23]姚瑶,霍元鹏,周伟,等.高产β-葡萄糖苷酶菌株的筛选及产酶条件优化[J].江西农业学报,2018,30(3):97-101.
[24] PATIDAR P,PILLAI S A,SHETH U,et al. Glucose triggered enhanced solubilisation,release and cytotoxicity of poorly water soluble anti-cancer drugs from T1307 micelles[J]. Journal of Biotechnology,2017,254:43-50.
[25] HOLDER G M,PLUMMER J L,RYAN A J. The metabolism and excretion of curcumin(1,7-Bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione)in the rat[J]. Xenobiotica,1978,8(12):761-768.
[26] ZENG Jia,YANG Nan,LI Xiumin,et al. 4'-O-methylglycosylation of curcumin by Beauveria bassiana[J]. Natural Product Communications,2010,5(1):77-80.
[2]袁鹏,陈莹,肖发,等.姜黄素的生物活性及在食品中的应用[J].食品工业科技,2012,33(14):371-375.
[3]柯秀梅,杨荣平,梁旭明.姜黄素增溶方法的研究进展[J].天然产物研究与开发,2013,25(8):1 154-1 159.
[4] HASSANINASAB A,HASHIMOTO Y,TOMITA-YOKKTANI K,et al. Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism[J]. Proceedings of the National Academy of Sciences,2011,108(16):6 615-6 620.
[5] PIANPUMEPONG P,ANAL A K,DOUNGCHAWEE G,et al. Study on enhanced absorption of phenolic compounds of Lactobacillus-fermented turmeric(Curcuma longa Linn.)beverages in rats[J]. International Journal of Food Science&Technology,2012,47(11):2 380-2 387.
[6] WANG Sujuan,PENG Xixi,CUI Liangliang,et al. Synthesis of water-soluble curcumin derivatives and their inhibition on lysozyme amyloid fibrillation[J]. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2018,190:89-95.
[7] KIMS W,HA K C,CHOI E K,et al. The effectiveness of fermented turmeric powder in subjects with elevated alanine transaminase levels:a randomised controlled study[J].BMC Complementary and Alternative Medicine,2013,13(1):58-58.
[8] SLAVOMIRA D,SOUTO E B,SILVA A M. Hansen solubility parameters(HSP)for pre-screening formulation of solid lipid nanoparticles(SLN):in vitro testing of curcumin-loaded SLN in MCF-7 and BT-474 cell lines[J].Pharmaceutical Development and Technology,2018,23(1):96-105.
[9] PURPURA M,LOWERY R P,WILSON J M,et al. Analysis of different innovative formulations of curcumin for improved relative oral bioavailability in human subjects[J].European Journal of Nutrition,2017,57(3):1-10.
[10] ANAND P,KUNNUMAKKARAA A B,NEWMAN R A,et al. Bioavailability of curcumin:problems and promises[J]. Mol Pharm,2007,4(6):807-818.
[11] PURPURA M,LOWERY R P,WILSON J M,et al. Analysis of different innovative formulations of curcumin for improved relative oral bioavailability in human subjects[J]. European Journal of Nutrition,2017,57(3):1-10.
[12]刘彬,赵莹,于思礼,等.微生物代谢工程发酵姜黄素研究进展[J].食品与发酵工业,2016,42(7):254-260.
[13]魏妍婷,马三梅.姜黄素衍生物及复合物抗肿瘤的研究[J].生命科学,2017,29(4):386-392.
[14]伍敏晖,王磊,何梅.高压微射流均质对姜黄素纳米乳液稳定性的影响[J].中国食品学报,2018,18(5):56-62.
[15]黄淑芳,应华洲,胡永洲.含氮姜黄素衍生物的合成及抗肿瘤活性研究[J].中国药物化学杂志,2011,21(2):88-95.
[16]陈建平,彭莞仪,秦小明,等.姜黄素超分子包合物的结构鉴定及其抗氧化活性[J].食品工业科技,2017(21):28-32.
[17] SAFAVY A,RAISCH P,MANTENA S,et al. Design and development of water-soluble curcumin conjugates as potential anticancer agents[J]. Journal of Medicinal Chemistry,2007,50(24):6 284-6 288.
[18] KAMINAGA Y,NAGATSU A,AKIYAMA T,et al. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus[J]. FEBS Letters,2003,555(2):311-316.
[19]孟岚,吴旭日,陈依军.糖苷合成酶及应用的研究进展[J].广西科学,2017,24(1):7-14.
[20] CHOUDHURY A K,RAJA S,MAHAPATRA S,et al.Synthesis and evaluation of the anti-oxidant capacity of curcumin glucuronides,the major curcumin metabolites[J]. Antioxidants,2015,4(4):750-767.
[21] ZHANG Xing,LI Min,LI Rui,et al. Microbial transformation of curcumin by Rhizopus chinensis[J]. Biocatalysis,2015,28(5-6):380-386.
[22] PRASAD E,HAMEEDA B,RAO A B,et al. Biotransformation of curcumin for improved biological activity and antiproliferative activity on acute HT-29 human cell lines[J]. Indian Journal of Biotechnology,2014,13(3):324-329.
[23]姚瑶,霍元鹏,周伟,等.高产β-葡萄糖苷酶菌株的筛选及产酶条件优化[J].江西农业学报,2018,30(3):97-101.
[24] PATIDAR P,PILLAI S A,SHETH U,et al. Glucose triggered enhanced solubilisation,release and cytotoxicity of poorly water soluble anti-cancer drugs from T1307 micelles[J]. Journal of Biotechnology,2017,254:43-50.
[25] HOLDER G M,PLUMMER J L,RYAN A J. The metabolism and excretion of curcumin(1,7-Bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione)in the rat[J]. Xenobiotica,1978,8(12):761-768.
[26] ZENG Jia,YANG Nan,LI Xiumin,et al. 4'-O-methylglycosylation of curcumin by Beauveria bassiana[J]. Natural Product Communications,2010,5(1):77-80.