诺丽发酵果汁化学成分及抗氧化活性研究
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摘要
采用多种色谱技术从诺丽(Morinda citrifolia)发酵果汁中分离得到10个化合物,并应用波谱学方法进行结构鉴定,分别鉴定为6,7-二羟基香豆素(1)、7-羟基香豆素(2)、东莨菪亭(3)、6-羟基-7-甲氧基香豆素(4)、7-羟基-4-甲基香豆素(5)、1,2,3,4-四氢-β-咔啉-3-羧酸(6)、(1S,3S)-1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸(7)、(1R,3S)-1-甲基-1,2,3,4-四氢-β-咔啉-3-羧酸(8)、对羟基苯甲酸(9)、龙胆酸(10)。利用DPPH和ABTS+·自由基清除能力法进行抗氧化活性测定,其中化合物1、3、4、10抗氧化活性较强,化合物1和10清除DPPH和ABTS+·自由基能力的IC50值分别为160.87、8.32和6.17、9.71μmol/L。化合物2、5~8均系首次从该植物中分离,本研究得到诺丽发酵果汁中香豆素、有机酸和生物碱三类成分,并且化合物1、3、4、10抗氧化活性良好。
Ten compounds were isolated from Noni( Morinda citrifolia) fermented juice by chromatography methods and identified as esculetin(1),7-hydroxycoumarin( 2) 、scopoletin( 3),6-hydroxy-7-methoxylcoumarin( 4),7-hydroxy-4-methylcoumarin(5),1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(6),(1 S,3 S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(7),(1 R,3 S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(8),p-hydroxybenzoic acid(9) and gentisic acid(10) by spectroscopic methods. The antioxidative activities were evaluated by DPPH and ABTS+ ·radical scavenging assay. Compounds 1,3,4,10 showed potential antioxidant antivity,in particular,1 and10 scavenged strongly DPPH and ABTS+ ·free radical with IC50160. 87,8. 32 and 6. 17,9. 71 μmol/L,respectively.Compounds 2 and 5-8 were isolated from Noni for the first time.
Ten compounds were isolated from Noni( Morinda citrifolia) fermented juice by chromatography methods and identified as esculetin(1),7-hydroxycoumarin( 2) 、scopoletin( 3),6-hydroxy-7-methoxylcoumarin( 4),7-hydroxy-4-methylcoumarin(5),1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(6),(1 S,3 S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(7),(1 R,3 S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid(8),p-hydroxybenzoic acid(9) and gentisic acid(10) by spectroscopic methods. The antioxidative activities were evaluated by DPPH and ABTS+ ·radical scavenging assay. Compounds 1,3,4,10 showed potential antioxidant antivity,in particular,1 and10 scavenged strongly DPPH and ABTS+ ·free radical with IC50160. 87,8. 32 and 6. 17,9. 71 μmol/L,respectively.Compounds 2 and 5-8 were isolated from Noni for the first time.
引文
1 Nelson SC.Morinda citrifolia(noni).Fruit-phytochemistry,pharmacology,safety institute of pharmaceutical biology[J].Planta Medica,2007,2006,952:161-168.
2 Chan-Blanco Y,Vaillant F,Perez A M,et al.The noni fruit(Morinda citrifolia L.):A review of agricultural research,nutritional and therapeutic properties[J].J Food Compos&Anal,2006,19:645-654.
3 Liu SM(刘树民),Wang Y(王宇),Zhang HC(张洪财),et al.Chemical constituents from fruits of Morinda citrifolia[J].Chin Tradit Herb Drugs(中草药),2012,43:2150-2153.
4 Baoning Su,ADP,Hyunah Jung,et al.Chemical constituents of the fruits of Morinda citrifolia(Noni)and their antioxidant activity[J].J Nat Prod,2005,68:592-595.
5 Yan YQ(晏永球),Tong YP(童应鹏),Lu Y(陆雨),et al.Research progress on chemical constituents of Morinda citrifolia and their pharmacological activities[J].Chin Tradit Herb Drugs(中草药),2017,48:1888-1905.
6 Liang HQ(梁寒峭),Cheng C(程池),Zhang L(张露),et al.Research of antioxidants in Noni fermentation juice[J].Nat Prod Res Dev(天然产物研究与开发),2016,28:1479-1483.
7 Liu LM(刘丽梅),Chen L(陈琳),Wang RH(王瑞海),et al.Chemical constituents of Fraxinus rhynchophylla Hance.[J].Chin Tradit Herb Drugs(中草药),2001,32:1073-1074.
8 W Peng,T Han,Y Wang,et al.chemical constituents of the aerial part of atractylodes macrocephala[J].Chem Nat Compd,2011,46:959-960.
9 Siddiqui BS,Sattar FA,Ahmad F,et al.Isolation and structural elucidation of chemical constituents from the fruits of Morinda citrifolia Linn[J].Arch Pharm Res,2007,30:919-923.
10 Xie T(谢韬),Liang JY(梁敬钰),Liu J(刘净),et al.Study on chemical constituents in bud of Artemisia scoparia[J].J Chin Pharm Univ(中国药科大学学报),2004,35:401-403.
11 Cussans NJ,Huckeby TN.Carbon-13NMR spectroscopy of heterocyclic Compounds-IV[J].Tetrahedron,1975,31:2719-2722.
12 Okuda T,Yoshida T,Shiota N,et al.L-3-carboxy-1,2,3,4-tetrahydro-β-carboline,a new amino acid from seeds of Aleurites fordii[J].Phytochemistry,1975,14:2304-2308.
13 Kawate T,Nakagawa M,Yamazaki H,et al.Alkylation of 3,4 -dihydro-β-carboline[J].Chem Pharm Bull,1993,41:287-289.
14 Xu SH,Zeng LM.Study on the chemical constituents of marine sponge Polymastia sobustia[J].Chin J Org Chem,2001,21(1):45-48.
15 Jun HE,Xian J,Song YY,et al.Chemical constituents of the root of Ampelopsis japonica(Thunb.)Makino[J].J Shenyang Pharm Univ(沈阳药科大学学报),2008,25:636-638.
16 Zhang HY,Wang LF.Theoretical elucidation of structure-activity relationship for coumarins to scavenge peroxyl radical[J].J Mol Struct(Theo&em),2004,673:199-202.
17 Li JX(李金霞),Cao YH(曹艳花),Bai FR(白飞荣),et al.Isolation and identification of endophytes from the wild Noni fruit of Xisha[J].Food Ferment Ind(食品与发酵工业),2014,40(3):68-75.
18 Liu Y,Li Y,Su Y,et al.Diversity and distribution of endophytic bacterial community in the Noni(Morinda citrifolia L.)plant[J].Afr J Microbiol Res,2015,9:1649-1657.
19 Liu Y,Cao YH,Su Y,et al.Diversity and spatial distribution of endophytes community composition in Noni(Morinda citrifolia L.)[C].National Infrastructure of Microbial Resource Seminar(全国微生物资源学术暨国家微生物资源平台运行服务研讨会),2015.
20 Zhang BG(张保国),Bai ZH(白志辉),Li ZM(李祖明),et al.Alkaline pectinase production by Bacillus clausii S-4 with solid state fermentaion[J].Food Ferment Ind(食品与发酵工业),2005,31(3):8-11.
21 Yan YP(严亚萍).Diversity of yeast and evaluation of active strains of Erhai lake and yangzonghai lake in Yunnan province[D].Yunnan:Yunnan University,2013.
2 Chan-Blanco Y,Vaillant F,Perez A M,et al.The noni fruit(Morinda citrifolia L.):A review of agricultural research,nutritional and therapeutic properties[J].J Food Compos&Anal,2006,19:645-654.
3 Liu SM(刘树民),Wang Y(王宇),Zhang HC(张洪财),et al.Chemical constituents from fruits of Morinda citrifolia[J].Chin Tradit Herb Drugs(中草药),2012,43:2150-2153.
4 Baoning Su,ADP,Hyunah Jung,et al.Chemical constituents of the fruits of Morinda citrifolia(Noni)and their antioxidant activity[J].J Nat Prod,2005,68:592-595.
5 Yan YQ(晏永球),Tong YP(童应鹏),Lu Y(陆雨),et al.Research progress on chemical constituents of Morinda citrifolia and their pharmacological activities[J].Chin Tradit Herb Drugs(中草药),2017,48:1888-1905.
6 Liang HQ(梁寒峭),Cheng C(程池),Zhang L(张露),et al.Research of antioxidants in Noni fermentation juice[J].Nat Prod Res Dev(天然产物研究与开发),2016,28:1479-1483.
7 Liu LM(刘丽梅),Chen L(陈琳),Wang RH(王瑞海),et al.Chemical constituents of Fraxinus rhynchophylla Hance.[J].Chin Tradit Herb Drugs(中草药),2001,32:1073-1074.
8 W Peng,T Han,Y Wang,et al.chemical constituents of the aerial part of atractylodes macrocephala[J].Chem Nat Compd,2011,46:959-960.
9 Siddiqui BS,Sattar FA,Ahmad F,et al.Isolation and structural elucidation of chemical constituents from the fruits of Morinda citrifolia Linn[J].Arch Pharm Res,2007,30:919-923.
10 Xie T(谢韬),Liang JY(梁敬钰),Liu J(刘净),et al.Study on chemical constituents in bud of Artemisia scoparia[J].J Chin Pharm Univ(中国药科大学学报),2004,35:401-403.
11 Cussans NJ,Huckeby TN.Carbon-13NMR spectroscopy of heterocyclic Compounds-IV[J].Tetrahedron,1975,31:2719-2722.
12 Okuda T,Yoshida T,Shiota N,et al.L-3-carboxy-1,2,3,4-tetrahydro-β-carboline,a new amino acid from seeds of Aleurites fordii[J].Phytochemistry,1975,14:2304-2308.
13 Kawate T,Nakagawa M,Yamazaki H,et al.Alkylation of 3,4 -dihydro-β-carboline[J].Chem Pharm Bull,1993,41:287-289.
14 Xu SH,Zeng LM.Study on the chemical constituents of marine sponge Polymastia sobustia[J].Chin J Org Chem,2001,21(1):45-48.
15 Jun HE,Xian J,Song YY,et al.Chemical constituents of the root of Ampelopsis japonica(Thunb.)Makino[J].J Shenyang Pharm Univ(沈阳药科大学学报),2008,25:636-638.
16 Zhang HY,Wang LF.Theoretical elucidation of structure-activity relationship for coumarins to scavenge peroxyl radical[J].J Mol Struct(Theo&em),2004,673:199-202.
17 Li JX(李金霞),Cao YH(曹艳花),Bai FR(白飞荣),et al.Isolation and identification of endophytes from the wild Noni fruit of Xisha[J].Food Ferment Ind(食品与发酵工业),2014,40(3):68-75.
18 Liu Y,Li Y,Su Y,et al.Diversity and distribution of endophytic bacterial community in the Noni(Morinda citrifolia L.)plant[J].Afr J Microbiol Res,2015,9:1649-1657.
19 Liu Y,Cao YH,Su Y,et al.Diversity and spatial distribution of endophytes community composition in Noni(Morinda citrifolia L.)[C].National Infrastructure of Microbial Resource Seminar(全国微生物资源学术暨国家微生物资源平台运行服务研讨会),2015.
20 Zhang BG(张保国),Bai ZH(白志辉),Li ZM(李祖明),et al.Alkaline pectinase production by Bacillus clausii S-4 with solid state fermentaion[J].Food Ferment Ind(食品与发酵工业),2005,31(3):8-11.
21 Yan YP(严亚萍).Diversity of yeast and evaluation of active strains of Erhai lake and yangzonghai lake in Yunnan province[D].Yunnan:Yunnan University,2013.