紫花苜蓿中活性成分的功能及分析测定技术研究进展
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摘要
紫花苜蓿为豆科蝶形花亚科苜蓿属植物,矿物质、蛋白质、维生素含量丰富,这些特性使其成为家畜饲料的理想选择,具有产草量高、利用年限长、再生性强、适口性强等优点,素有"牧草之王"的称号。此外,紫花苜蓿中含有多种活性化合物成分,包括:矿物质、氨基酸、非蛋白质氨基酸、有机酸、多元醇、生物碱、胡萝卜素、香豆素、消化酶、类黄酮、酚类化合物、植物雌激素、植物甾醇、多胺、皂素以及其他挥发性有机化合物,如萜烯类、呋喃类、醇类和酮类等化合物。文章综述了近十年有关紫花苜蓿活性化合物成分功能及其分析检测方法,将紫花苜蓿中的活性成分分为三大类型:矿物质、初级代谢产物以及次级代谢产物,分别详细地综述了每种类型所包括的具体化合物活性成分、活性成分的生理功能及其相关的分析测定技术,介绍了紫花苜蓿中各种活性化合物成分的有效分析方法,旨在为今后紫花苜蓿活性物质研究提供科学有利的技术参考。
Alfalfa, a genus of the genus Eucalyptus, is rich in minerals, protein and vitamins. These characteristics make it an ideal choice for livestock feed, and because of its high grass yield, long life, and regeneration. It has the advantages of strong sex and strong palatability, and is known as the "king of the pasture". In addition, alfalfa contains a variety of active ingredients, including: minerals, amino acids, non-protein amino acids, organic acids, polyols, alkaloids, carotene,coumarin, digestive enzymes, flavonoids, phenolic compounds, plants Estrogen, phytosterols, polyamines, saponins and other volatile organic compounds such as terpenes, furans, alcohols and ketones. In this paper, the functions of the active constituents of alfalfa and their analytical methods were reviewed. The active constituents of alfalfa were divided into three types: minerals, primary metabolites and secondary metabolites. The types of specific compounds, the physiological functions of the active ingredients, and the related analytical techniques, and the effective analysis methods for various active compound components in alfalfa, aim to provide an advantageous technical reference for scientific research in future alfalfa active substances.
Alfalfa, a genus of the genus Eucalyptus, is rich in minerals, protein and vitamins. These characteristics make it an ideal choice for livestock feed, and because of its high grass yield, long life, and regeneration. It has the advantages of strong sex and strong palatability, and is known as the "king of the pasture". In addition, alfalfa contains a variety of active ingredients, including: minerals, amino acids, non-protein amino acids, organic acids, polyols, alkaloids, carotene,coumarin, digestive enzymes, flavonoids, phenolic compounds, plants Estrogen, phytosterols, polyamines, saponins and other volatile organic compounds such as terpenes, furans, alcohols and ketones. In this paper, the functions of the active constituents of alfalfa and their analytical methods were reviewed. The active constituents of alfalfa were divided into three types: minerals, primary metabolites and secondary metabolites. The types of specific compounds, the physiological functions of the active ingredients, and the related analytical techniques, and the effective analysis methods for various active compound components in alfalfa, aim to provide an advantageous technical reference for scientific research in future alfalfa active substances.
引文
[1]何春年,李展,高微微,等.苜蓿属植物的黄酮类化学成分研究概况[J].中国药学杂志,2006,41(8):565-568.
[2]EGAMBERDIEVA D,MAMADALIEVA N,KHODJIMATOV O,et al.Medicinal plants from Chatkal biosphere reserve used for folk medicine in Uzbekistan Med[J].Plant Biotechnol,2012,7:56-64.
[3]BORA K S,SHARMA A.Phytochemical and pharmacologic al potential of Medicago sativa:a review[J].Pharmaceutic al Biology,2011,49:211-220.
[4]RANA M G,KATBMNA R V,PADHYA A,et al.In Vitro antioxidant and free radical scavenging studies of alcoholic extract of Medicago sativa L[J].Plant Biotechnol,2010,55:15-22.
[5]GOLAWSKA S,UKASIK I,WOJCICKA A,et al.Relationship between saponin content in alfalfa and aphid development[J].Acta Biological Cracoviensia,2012,54:39-46.
[6]LIANG J,YANG Z,CAO X,et al.Preparative isolation of novel antioxidant flavonoids of alfalfa by stop-and-go countercurrent chromatography and following on-line liquid chromatography desalination[J].Journal of Chromatography A,2011,1218:6191-6199.
[7]WANG S P,DONG X F,MA H,et al.Purification,characterisation and protective effects of polysaccharides from alfalfa on hepatocytes[J].Carbohydrate Polymers,2014,112:608-614.
[8]HORBOWICZ M,OBENDOF R L,MCKERSIE B D,et al.Soluble saccharides and cyclitols in alfalfa(Medicago sativa L.)somatic embryos,leaflets,and mature seeds[J].Plant Science,1995,109:191-198.
[9]刘世亮,张炳云,介晓磊,等.铁、锌、钼配施对紫花苜蓿微量元素吸收的影响[J].中国草地学报,2008,30(2):54-61
[10]WORTHINGTON R B,BRESKIN M F.A pharmacists guide to controversial“nutrition products”[J].American Pharmaceutical Review,1983,23:30-42.
[11]ZHANG X,YU L,LI X H,et al.Total fractionation and characterization of the water-soluble polysaccharides isolated from Panax ginseng C A.Meyer[J].Carbohydrate Polymers,2009,77(3):544-552.
[12]MAEHARA Y,TSUJITANI S,SAREKI H,et al.Biological mechanism and clinical effect of proteinbound polysaccharide K(KRESTIN):review of development and future perspectives[J].Surgery Today,2012,42:8-28.
[13]LI J S,TANG Y S,MENG X H,et al.The proliferative effects of alfalfa polysaccharides on the mouse immune cells[J].Life Science Journal,2013,10(2):868-873.
[14]HOSSAM Al-SUOD,HEANA-ANDREEA RATIU,Magdalena L,et al.Determination of sugars and cyclitols isolated from various morphological parts of Medicago sativa L[J].Journal of separation science,2018,41(5):1118-1128.
[15]李冲,吴峰洋,刘亚娟,等.紫花苜蓿的营养特性及其在畜禽生产中的应用[J].中国饲料,2015(24):15-21.
[16]FOUGERE F,LERD,STREETER J G,et al.Effects of salt stress on amino acid,organic acid,and carbohydrate composition of roots,bacteroids,and cytosol of alfalfa(Medicago sativa L.)[J].Plant Physiol,1991,96:1228-1236.
[17]田春丽,介小磊,刘巘,等.硒锌与富啡酸配施对紫花苜蓿产量、营养成分及氨基酸组成的影响[J].草业学报,2014,23(2):66-75.
[18]MOLERO G,ARANIUELO I,TEIXIDOR P.et al.Measurement of 13 C and 15 N isotope labeling by gas chromatography combustion isotope ratio mass spectrometry to study amino acid fluxes in a plantmicrobe symbiotic association[J].Rapid Communications in Mass Spectrometry,2011,25:599-607.
[19]SNAPPSS,VANCECP.Asparagine biosynthesis in alfalfa(Medicago sativa L.)root nodules[J].Plant Physiol,1986,82:390-395.
[20]PHILLIPSDA,JOSEPHCM,MAXWELLCA.Trigonelline and stachydrine released from alfalfa seeds activate Nod D2 protein in Rhizobium meliloti[J].Plant Physiol,1992,99:1526-1531.
[21]NAIDU B P,PALEG L G,Jones G P.Nitrogenous compatible solutes in drought-stressed Medicago sativa[J].Phytochemistry,1992,31:1195-1197.
[22]KRAKOWSKA A,RAFIN SKA K,WALCZAK J,et al.Comparison of various extraction techniques of Medicago sativa:yield,antioxidant activity,and content of phytochemical constituents[J].Journal of AOACInternational,2017,100:1-13.
[23]FUSKOVA A,PROKSA B,FUSKA.In vitro effects if duclauxin and derivatives of coumarins acid and Protein synthesis in Ehrlich's ascites[J].Pharmazie,1977,32:291.
[24]卢成,曾昭海,张涛,等.紫花苜蓿生物活性成分研究进展[J].草业科学,2005,22(9):28-31.
[25]HABIBS A,RAHMANAA.Evaluation of some weed extracts against field dodder on alfalfa(Medicago sativa)[J].Journal of Chemical Ecology,1988,14:443-452.
[26]BIGGS D R,SHAW G J.WAIROL.A new coumarins from Medicago sativa[J].Phytochemistry,1980,19:2801-2802.
[27]EI-KHRISYEAM,ABDEL-HAFEZOM,KHATTABAA,et al.Chemical constituents of Medicago sativa[J].Bull Natl Res Cent,1994,19:117-221.
[28]ABDEL-HAFEZ OM.Constituents of Medicago sativa fruits[J].Fitoterapia,1993,64:381-382.
[29]赵娅敏,马好文,孟淑娟.紫花苜蓿中黄酮类化学成分及其生物活性研究进展[J].中草药,2013(44):3245-3252.
[30]SMOLINSKI A T,PESTKA J J.Deoxynivalenol:toxicology and potential effects on humans[J].Toxicol Environ Health B Critical Review,2005,8:39-69.
[31]SHENOUDA N S,ZHOU C,BROWNING J D,et al.Phytoestrogens in common herbs regulate prostate cancer cell growth in vitro[J].Nutrition Cancer,2004,49(2):200-208.
[32]CASAGRANDE F,DARBON JM.Effects of structurally related flavonoids on cell cycle progression of human melanoma cells:regulation of cyclin-dependent kinases CDK2 and CDK1[J].Biochemical Pharmacol,2001,61:1205-1215.
[33]王先科,史莹华,王成章,等.苜蓿皂甙对高脂血症大鼠胆固醇代谢及肝脏ACAT-2和HMG-GOAR基因表达的影响[J].草业学报,2012,21(3):287-293.
[34]DAVID O,BAHRAM H,ARJMANDI.Soy protein saponins and plasma cholesterol Reply[J].The Journal of Nutrition,2001,131:2971-2972.
[35]MALINOW M,MCLAUGHLIN P,NAITO H,et al.Effect of alfalfa meal on shrinkage(regression)of atherosclerotic plaques during cholesterol feeding in monkeys[J].Atherosclerosis,1978,30:27-43.
[36]WANG J,ZHOU Y X,LI Y.Effects of Alfalfa Saponins and Yeast Culture on Production Performance of Animal[J].Anim Husbandry and Feed Science,2010,31(8):19-20.
[37]BIALY Z,JURZYSTA M,OLESZEK W,et al.Saponins in alfalfa(Medicago sativa L.)root and their structural elucidation[J].Journal of Agricutural and Food Chemistry,1999,47:3185-3192.
[38]OLESZEK W,PRICE K R,COLQUHOUM I J,et al.Isolation and identification of alfalfa(Medicago sativa L.)root saponins:their activity in relation to a fungal bioassay[J].Journal of Agricutural and Food Chemistry,1990,38:1810-1817.
[39]STOCHMALA,SIMONET A M.,Macias F A.et al.Alfalfa(Medicago sativa L.)flavonoids.2.tricin and chrysoeriol glycosides from aerial parts[J].Journal of Agricutural and Food Chemistry,2001,49:5310-5314.
[40]NEWBY V K,SABLOM R M,Synge R L M,et al.Free and bound phenolic acids of lucerne(Medicago sativa cv Europe)[J].Phytochemistry,1980,19:651-657.
[41]LAROSE G,CHENEVERT R,MOUTOGLIS P,et al.Flavonoid levels in roots of M.sativa are modulated by developmental stage of the symbiosis and the root colonizing arbuscular mycorrhizal fungus[J].Journal of Plant Physiology,2002,159:1329-1339.
[42]DOEBLERT D C,DUKE S H,ANDERSON L.Amylases from alfalfa(Medicago sativa L.)roots[J].Plant Physiology,1982,69:1096-1102.
[43]TOTHEC,VISSI E,KOVACS I,SZOKE A,ARINO,et al.Protein phosphatase 2A holoenzyme and its subunits from Medicago sativa[J].Plant Moleculer Biological,2000,43:527-536.
[44]BARCELO F,MIRALES F,AREAN C O.Purification and characterization of ferritin from alfalfa seeds[J].Journal of Inorganic Biochemistry,2002,66:23-27.
[2]EGAMBERDIEVA D,MAMADALIEVA N,KHODJIMATOV O,et al.Medicinal plants from Chatkal biosphere reserve used for folk medicine in Uzbekistan Med[J].Plant Biotechnol,2012,7:56-64.
[3]BORA K S,SHARMA A.Phytochemical and pharmacologic al potential of Medicago sativa:a review[J].Pharmaceutic al Biology,2011,49:211-220.
[4]RANA M G,KATBMNA R V,PADHYA A,et al.In Vitro antioxidant and free radical scavenging studies of alcoholic extract of Medicago sativa L[J].Plant Biotechnol,2010,55:15-22.
[5]GOLAWSKA S,UKASIK I,WOJCICKA A,et al.Relationship between saponin content in alfalfa and aphid development[J].Acta Biological Cracoviensia,2012,54:39-46.
[6]LIANG J,YANG Z,CAO X,et al.Preparative isolation of novel antioxidant flavonoids of alfalfa by stop-and-go countercurrent chromatography and following on-line liquid chromatography desalination[J].Journal of Chromatography A,2011,1218:6191-6199.
[7]WANG S P,DONG X F,MA H,et al.Purification,characterisation and protective effects of polysaccharides from alfalfa on hepatocytes[J].Carbohydrate Polymers,2014,112:608-614.
[8]HORBOWICZ M,OBENDOF R L,MCKERSIE B D,et al.Soluble saccharides and cyclitols in alfalfa(Medicago sativa L.)somatic embryos,leaflets,and mature seeds[J].Plant Science,1995,109:191-198.
[9]刘世亮,张炳云,介晓磊,等.铁、锌、钼配施对紫花苜蓿微量元素吸收的影响[J].中国草地学报,2008,30(2):54-61
[10]WORTHINGTON R B,BRESKIN M F.A pharmacists guide to controversial“nutrition products”[J].American Pharmaceutical Review,1983,23:30-42.
[11]ZHANG X,YU L,LI X H,et al.Total fractionation and characterization of the water-soluble polysaccharides isolated from Panax ginseng C A.Meyer[J].Carbohydrate Polymers,2009,77(3):544-552.
[12]MAEHARA Y,TSUJITANI S,SAREKI H,et al.Biological mechanism and clinical effect of proteinbound polysaccharide K(KRESTIN):review of development and future perspectives[J].Surgery Today,2012,42:8-28.
[13]LI J S,TANG Y S,MENG X H,et al.The proliferative effects of alfalfa polysaccharides on the mouse immune cells[J].Life Science Journal,2013,10(2):868-873.
[14]HOSSAM Al-SUOD,HEANA-ANDREEA RATIU,Magdalena L,et al.Determination of sugars and cyclitols isolated from various morphological parts of Medicago sativa L[J].Journal of separation science,2018,41(5):1118-1128.
[15]李冲,吴峰洋,刘亚娟,等.紫花苜蓿的营养特性及其在畜禽生产中的应用[J].中国饲料,2015(24):15-21.
[16]FOUGERE F,LERD,STREETER J G,et al.Effects of salt stress on amino acid,organic acid,and carbohydrate composition of roots,bacteroids,and cytosol of alfalfa(Medicago sativa L.)[J].Plant Physiol,1991,96:1228-1236.
[17]田春丽,介小磊,刘巘,等.硒锌与富啡酸配施对紫花苜蓿产量、营养成分及氨基酸组成的影响[J].草业学报,2014,23(2):66-75.
[18]MOLERO G,ARANIUELO I,TEIXIDOR P.et al.Measurement of 13 C and 15 N isotope labeling by gas chromatography combustion isotope ratio mass spectrometry to study amino acid fluxes in a plantmicrobe symbiotic association[J].Rapid Communications in Mass Spectrometry,2011,25:599-607.
[19]SNAPPSS,VANCECP.Asparagine biosynthesis in alfalfa(Medicago sativa L.)root nodules[J].Plant Physiol,1986,82:390-395.
[20]PHILLIPSDA,JOSEPHCM,MAXWELLCA.Trigonelline and stachydrine released from alfalfa seeds activate Nod D2 protein in Rhizobium meliloti[J].Plant Physiol,1992,99:1526-1531.
[21]NAIDU B P,PALEG L G,Jones G P.Nitrogenous compatible solutes in drought-stressed Medicago sativa[J].Phytochemistry,1992,31:1195-1197.
[22]KRAKOWSKA A,RAFIN SKA K,WALCZAK J,et al.Comparison of various extraction techniques of Medicago sativa:yield,antioxidant activity,and content of phytochemical constituents[J].Journal of AOACInternational,2017,100:1-13.
[23]FUSKOVA A,PROKSA B,FUSKA.In vitro effects if duclauxin and derivatives of coumarins acid and Protein synthesis in Ehrlich's ascites[J].Pharmazie,1977,32:291.
[24]卢成,曾昭海,张涛,等.紫花苜蓿生物活性成分研究进展[J].草业科学,2005,22(9):28-31.
[25]HABIBS A,RAHMANAA.Evaluation of some weed extracts against field dodder on alfalfa(Medicago sativa)[J].Journal of Chemical Ecology,1988,14:443-452.
[26]BIGGS D R,SHAW G J.WAIROL.A new coumarins from Medicago sativa[J].Phytochemistry,1980,19:2801-2802.
[27]EI-KHRISYEAM,ABDEL-HAFEZOM,KHATTABAA,et al.Chemical constituents of Medicago sativa[J].Bull Natl Res Cent,1994,19:117-221.
[28]ABDEL-HAFEZ OM.Constituents of Medicago sativa fruits[J].Fitoterapia,1993,64:381-382.
[29]赵娅敏,马好文,孟淑娟.紫花苜蓿中黄酮类化学成分及其生物活性研究进展[J].中草药,2013(44):3245-3252.
[30]SMOLINSKI A T,PESTKA J J.Deoxynivalenol:toxicology and potential effects on humans[J].Toxicol Environ Health B Critical Review,2005,8:39-69.
[31]SHENOUDA N S,ZHOU C,BROWNING J D,et al.Phytoestrogens in common herbs regulate prostate cancer cell growth in vitro[J].Nutrition Cancer,2004,49(2):200-208.
[32]CASAGRANDE F,DARBON JM.Effects of structurally related flavonoids on cell cycle progression of human melanoma cells:regulation of cyclin-dependent kinases CDK2 and CDK1[J].Biochemical Pharmacol,2001,61:1205-1215.
[33]王先科,史莹华,王成章,等.苜蓿皂甙对高脂血症大鼠胆固醇代谢及肝脏ACAT-2和HMG-GOAR基因表达的影响[J].草业学报,2012,21(3):287-293.
[34]DAVID O,BAHRAM H,ARJMANDI.Soy protein saponins and plasma cholesterol Reply[J].The Journal of Nutrition,2001,131:2971-2972.
[35]MALINOW M,MCLAUGHLIN P,NAITO H,et al.Effect of alfalfa meal on shrinkage(regression)of atherosclerotic plaques during cholesterol feeding in monkeys[J].Atherosclerosis,1978,30:27-43.
[36]WANG J,ZHOU Y X,LI Y.Effects of Alfalfa Saponins and Yeast Culture on Production Performance of Animal[J].Anim Husbandry and Feed Science,2010,31(8):19-20.
[37]BIALY Z,JURZYSTA M,OLESZEK W,et al.Saponins in alfalfa(Medicago sativa L.)root and their structural elucidation[J].Journal of Agricutural and Food Chemistry,1999,47:3185-3192.
[38]OLESZEK W,PRICE K R,COLQUHOUM I J,et al.Isolation and identification of alfalfa(Medicago sativa L.)root saponins:their activity in relation to a fungal bioassay[J].Journal of Agricutural and Food Chemistry,1990,38:1810-1817.
[39]STOCHMALA,SIMONET A M.,Macias F A.et al.Alfalfa(Medicago sativa L.)flavonoids.2.tricin and chrysoeriol glycosides from aerial parts[J].Journal of Agricutural and Food Chemistry,2001,49:5310-5314.
[40]NEWBY V K,SABLOM R M,Synge R L M,et al.Free and bound phenolic acids of lucerne(Medicago sativa cv Europe)[J].Phytochemistry,1980,19:651-657.
[41]LAROSE G,CHENEVERT R,MOUTOGLIS P,et al.Flavonoid levels in roots of M.sativa are modulated by developmental stage of the symbiosis and the root colonizing arbuscular mycorrhizal fungus[J].Journal of Plant Physiology,2002,159:1329-1339.
[42]DOEBLERT D C,DUKE S H,ANDERSON L.Amylases from alfalfa(Medicago sativa L.)roots[J].Plant Physiology,1982,69:1096-1102.
[43]TOTHEC,VISSI E,KOVACS I,SZOKE A,ARINO,et al.Protein phosphatase 2A holoenzyme and its subunits from Medicago sativa[J].Plant Moleculer Biological,2000,43:527-536.
[44]BARCELO F,MIRALES F,AREAN C O.Purification and characterization of ferritin from alfalfa seeds[J].Journal of Inorganic Biochemistry,2002,66:23-27.