Advances in Chemical Constituents and Quality Control of Turmeric
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摘要
Turmeric,derived from the rhizomes of Curcuma longa L.(Zingiberaceae),is one of the most popular herbal medicines.Its main bioactive constituents include curcuminoids,sesquiterpenes,and terpecurcumins.It exhibits antitumor, anti-inflammatory, antioxidant, antibacterial, and antiviral activities.With the rapid development of analytical technologies,remarkable progress has been made in studies of turmeric.This review article summarizes research advances in chemical analysis and quality control of turmeric from 2009 to 2018.
Turmeric,derived from the rhizomes of Curcuma longa L.(Zingiberaceae),is one of the most popular herbal medicines.Its main bioactive constituents include curcuminoids,sesquiterpenes,and terpecurcumins.It exhibits antitumor, anti-inflammatory, antioxidant, antibacterial, and antiviral activities.With the rapid development of analytical technologies,remarkable progress has been made in studies of turmeric.This review article summarizes research advances in chemical analysis and quality control of turmeric from 2009 to 2018.
Turmeric,derived from the rhizomes of Curcuma longa L.(Zingiberaceae),is one of the most popular herbal medicines.Its main bioactive constituents include curcuminoids,sesquiterpenes,and terpecurcumins.It exhibits antitumor, anti-inflammatory, antioxidant, antibacterial, and antiviral activities.With the rapid development of analytical technologies,remarkable progress has been made in studies of turmeric.This review article summarizes research advances in chemical analysis and quality control of turmeric from 2009 to 2018.
引文
1.Wan DG,Peng C,Zhao JN.Geo-authentic herbs records in Sichuan.Sichuan,China:Sichuan Science and Technology Press;2005.p.443-53.
2.Chinese Pharmacopoeia Commission.Pharmacopoeia of the People’s Republic of China.Vol.1.Beijing,China:Ministry of Health of the People’s Republic of China;2015.p.264-5.
3.Li R,Yan X,He XY,Wang XY.Advance in the research on chemical constitute,biological activity and in vivo metabolism of Curcuma longa L.J Xihua Univ 2013;32:98-104.
4.Zhao XL.Research progress in chemical constituents,biological activities and exploration utilization of Curcuma longa L.China Condiment 2012;5:9-13.
5.Li R,Xiang C,Zhang X,Guo DA,Ye M.Chemical analysis of the Chinese herbal medicine turmeric(Curcuma longa L.).Curr Pharm Anal 2010;6:256-68.
6.Xue YC,Zhou Y,Kang YQ,Ye ZY,Tu YY,Chen L,et al.Research progress of turmeric volatile oil.West China J Pharm Sci 2016;31:212-5.
7.Dao TT,Nguyen PH,Won HK,Kim EH,Park J,Won BY,et al.Curcuminoids from Curcuma longa and their inhibitory activities on influenza A neuraminidases.Food Chem 2012;134:21-8.
8.Small GW,Siddarth P,Li Z,Miller KJ,Ercoli L,Emerson ND,et al.Memory and brain amyloid and tau effects of a bioavailable form of curcumin in non-demented adults:A double-blind,placebo-controlled18-month trial.Am J Geriatr Psychiatry 2018;26:266-77.
9.Datta S,Misra SK,Saha ML,Lahiri N,Louie J,Pan D,et al.Orthogonal self-assembly of an organoplatinum(II)metallacycle and cucurbit[8]uril that delivers curcumin to cancer cells.Proc Natl Acad Sci U S A2018;115:8087-92.
10.Zhang WY,Wang HF,Chen G,Zhang O,Bai S,Pei YH.Two new bisabolane sesquiterpenoids from Curcuma longa.J Asian Nat Prod Res2014;16:271-4.
11.Xu J,Ji F,Kang J,Wang H,Li S,Jin DQ,et al.Absolute configurations and NO inhibitory activities of terpenoids from Curcuma longa.J Agric Food Chem 2015;63:5805-12.
12.Zhang JX,Xiao YC,Liu M,Ran J,Xu HR,Huang J.Study on the sesquiterpene constituents of Curcuma longa.West Chin J Pharm Sci2014;29:262-5.
13.Li J,Wang HF,Chen G,Huang SD,Zhang WY,Hua HM,et al.Structure determination of two new bisabolane-type sesquiterpenes from the rhizomes of Curcuma longa by NMR spectroscopy.Magn Reson Chem2015;53:536-8.
14.Lin X,Ji S,Li R,Dong Y,Qiao X,Hu H,et al.Terpecurcumins A-I from the rhizomes of Curcuma longa:Absolute configuration and cytotoxic activity.J Nat Prod 2012;75:2121-31.
15.Qiao X,Lin XH,Ji S,Zhang ZX,Bo T,Guo DA,et al.Global profiling and novel structure discovery using multiple neutral loss/precursor ion scanning combined with substructure recognition and statistical analysis(MNPSS):Characterization of terpene-conjugated curcuminoids in Curcuma longa as a case study.Anal Chem 2016;88:703-10.
16.Lin X,Ji S,Qiao X,Hu H,Chen N,Dong Y,et al.Density functional theory calculations in stereochemical determination of terpecurcumins J-W,cytotoxic terpene-conjugated curcuminoids from Curcuma longa L.J Org Chem 2013;78:11835-48.
17.Xiao YC,Xie J,Yu M,Liu M,Ran J,Xi Z,et al.Bisabocurcumin,a new skeleton curcuminoid from the rhizomes of Curcuma longa L.Chin Chem Lett 2011;22:1457-60.
18.Dong Y,Yin S,Song X,Huo Y,Fan L,Ye M,et al.Involvement of ROS-p38-H2AX axis in novel curcumin analogues-induced apoptosis in breast cancer cells.Mol Carcinog 2016;55:323-34.
19.Jin S,Song C,Jia S,Li S,Zhang Y,Chen C,et al.An integrated strategy for establishment of curcuminoid profile in turmeric using two LC-MS/MS platforms.J Pharm Biomed Anal 2017;132:93-102.
20.Hu Y,Kong W,Yang X,Xie L,Wen J,Yang M,et al.GC-MS combined with chemometric techniques for the quality control and original discrimination of curcumae longae rhizome:Analysis of essential oils.J Sep Sci 2014;37:404-11.
21.Naz S,Ilyas S,Parveen Z,Javed S.Chemical analysis of essential oils from turmeric(Curcuma longa)rhizome through GC-MS.Asian JChem 2010;22:3153-8.
22.Paramasivam M,Poi R,Banerjee RP,Bandyopadhyay A.High-performance thin layer chromatographic method for quantitative determination of curcuminoids in Curcuma longa germplasm.Food Chem 2009;113:640-4.
23.Zhang JS,Guan J,Yang FQ,Liu HG,Cheng XJ,Li SP,et al.Qualitative and quantitative analysis of four species of Curcuma rhizomes using twice development thin layer chromatography.J Pharm Biomed Anal2008;48:1024-8.
24.Li R,Xiang C,Ye M,Li HF,Zhang X,Guo DA,et al.Qualitative and quantitative analysis of curcuminoids in herbal medicines derived from Curcuma species.Food Chem 2011;126:1890-5.
25.Avula B,Wang YH,Khan IA.Quantitative determination of curcuminoids from the roots of Curcuma longa,Curcuma species and dietary supplements using an UPLC-UV-MS method.Planta Med 2009;3:1-6.
26.Chao IC,Wang CM,Li SP,Lin LG,Ye WC,Zhang QW,et al.Simultaneous quantification of three curcuminoids and three volatile components of Curcuma longa using pressurized liquid extraction and high-performance liquid chromatography.Molecules 2018;23.pii:E1568.
27.Long Y,Zhang W,Wang F,Chen Z.Simultaneous determination of three curcuminoids in Curcuma longa L.by high-performance liquid chromatography coupled with electrochemical detection.J Pharm Anal2014;4:325-30.
28.Osorio-Tobón JF,Carvalho PI,Barbero GF,Nogueira GC,Rostagno MA,Meireles MA,et al.Fast analysis of curcuminoids from turmeric(Curcuma longa L.)by high-performance liquid chromatography using a fused-core column.Food Chem 2016;200:167-74.
29.Shen Y,Han C,Chen X,Hou X,Long Z.Simultaneous determination of three curcuminoids in Curcuma Wenyujin Y.H.Chen et C.Ling.by liquid chromatography-tandem mass spectrometry combined with pressurized liquid extraction.J Pharm Biomed Anal 2013;81-82:146-50.
30.Ashraf K,Mujeeb M,Ahmad A,Ahmad N,Amir M.Determination of curcuminoids in Curcuma longa Linn.By UPLC/Q-TOF-MS:An application in turmeric cultivation.J Chromatogr Sci2015;53:1346-52.
31.Anubala S,Sekar R,Nagaiah K.Development and validation of an analytical method for the separation and determination of major bioactive curcuminoids in Curcuma longa rhizomes and herbal products using non-aqueous capillary electrophoresis.Talanta 2014;123:10-7.
32.Anubala S,Sekar R,Nagaiah K.Determination of curcuminoids and their degradation products in turmeric(Curcuma longa)rhizome herbal products by non-aqueous capillary electrophoresis with photodiode array detection.Food Anal Method 2016;9:2567-78.
33.Li F,Liu R,Yang F,Xiao W,Chen C,Xia ZN.Determination of three curcuminoids in Curcuma longa by microemulsion electrokinetic chromatography with protective effects on the analytes.Anal Methods2014;6:2566.
34.Chen SD,Chen JP,Chen F.Determination of inorganic elements in Curcuma longa by ICP-MS/ICP-AES.China Condiment 2010;8:102-4.
35.Chen JH,Tang YS,Liu DW,Wang NS.Residue determination of six kinds of heavy metal in rhizoma curcumae longae.Tradit Chin Drug Res Pharmacol 2009;20:457-60.
2.Chinese Pharmacopoeia Commission.Pharmacopoeia of the People’s Republic of China.Vol.1.Beijing,China:Ministry of Health of the People’s Republic of China;2015.p.264-5.
3.Li R,Yan X,He XY,Wang XY.Advance in the research on chemical constitute,biological activity and in vivo metabolism of Curcuma longa L.J Xihua Univ 2013;32:98-104.
4.Zhao XL.Research progress in chemical constituents,biological activities and exploration utilization of Curcuma longa L.China Condiment 2012;5:9-13.
5.Li R,Xiang C,Zhang X,Guo DA,Ye M.Chemical analysis of the Chinese herbal medicine turmeric(Curcuma longa L.).Curr Pharm Anal 2010;6:256-68.
6.Xue YC,Zhou Y,Kang YQ,Ye ZY,Tu YY,Chen L,et al.Research progress of turmeric volatile oil.West China J Pharm Sci 2016;31:212-5.
7.Dao TT,Nguyen PH,Won HK,Kim EH,Park J,Won BY,et al.Curcuminoids from Curcuma longa and their inhibitory activities on influenza A neuraminidases.Food Chem 2012;134:21-8.
8.Small GW,Siddarth P,Li Z,Miller KJ,Ercoli L,Emerson ND,et al.Memory and brain amyloid and tau effects of a bioavailable form of curcumin in non-demented adults:A double-blind,placebo-controlled18-month trial.Am J Geriatr Psychiatry 2018;26:266-77.
9.Datta S,Misra SK,Saha ML,Lahiri N,Louie J,Pan D,et al.Orthogonal self-assembly of an organoplatinum(II)metallacycle and cucurbit[8]uril that delivers curcumin to cancer cells.Proc Natl Acad Sci U S A2018;115:8087-92.
10.Zhang WY,Wang HF,Chen G,Zhang O,Bai S,Pei YH.Two new bisabolane sesquiterpenoids from Curcuma longa.J Asian Nat Prod Res2014;16:271-4.
11.Xu J,Ji F,Kang J,Wang H,Li S,Jin DQ,et al.Absolute configurations and NO inhibitory activities of terpenoids from Curcuma longa.J Agric Food Chem 2015;63:5805-12.
12.Zhang JX,Xiao YC,Liu M,Ran J,Xu HR,Huang J.Study on the sesquiterpene constituents of Curcuma longa.West Chin J Pharm Sci2014;29:262-5.
13.Li J,Wang HF,Chen G,Huang SD,Zhang WY,Hua HM,et al.Structure determination of two new bisabolane-type sesquiterpenes from the rhizomes of Curcuma longa by NMR spectroscopy.Magn Reson Chem2015;53:536-8.
14.Lin X,Ji S,Li R,Dong Y,Qiao X,Hu H,et al.Terpecurcumins A-I from the rhizomes of Curcuma longa:Absolute configuration and cytotoxic activity.J Nat Prod 2012;75:2121-31.
15.Qiao X,Lin XH,Ji S,Zhang ZX,Bo T,Guo DA,et al.Global profiling and novel structure discovery using multiple neutral loss/precursor ion scanning combined with substructure recognition and statistical analysis(MNPSS):Characterization of terpene-conjugated curcuminoids in Curcuma longa as a case study.Anal Chem 2016;88:703-10.
16.Lin X,Ji S,Qiao X,Hu H,Chen N,Dong Y,et al.Density functional theory calculations in stereochemical determination of terpecurcumins J-W,cytotoxic terpene-conjugated curcuminoids from Curcuma longa L.J Org Chem 2013;78:11835-48.
17.Xiao YC,Xie J,Yu M,Liu M,Ran J,Xi Z,et al.Bisabocurcumin,a new skeleton curcuminoid from the rhizomes of Curcuma longa L.Chin Chem Lett 2011;22:1457-60.
18.Dong Y,Yin S,Song X,Huo Y,Fan L,Ye M,et al.Involvement of ROS-p38-H2AX axis in novel curcumin analogues-induced apoptosis in breast cancer cells.Mol Carcinog 2016;55:323-34.
19.Jin S,Song C,Jia S,Li S,Zhang Y,Chen C,et al.An integrated strategy for establishment of curcuminoid profile in turmeric using two LC-MS/MS platforms.J Pharm Biomed Anal 2017;132:93-102.
20.Hu Y,Kong W,Yang X,Xie L,Wen J,Yang M,et al.GC-MS combined with chemometric techniques for the quality control and original discrimination of curcumae longae rhizome:Analysis of essential oils.J Sep Sci 2014;37:404-11.
21.Naz S,Ilyas S,Parveen Z,Javed S.Chemical analysis of essential oils from turmeric(Curcuma longa)rhizome through GC-MS.Asian JChem 2010;22:3153-8.
22.Paramasivam M,Poi R,Banerjee RP,Bandyopadhyay A.High-performance thin layer chromatographic method for quantitative determination of curcuminoids in Curcuma longa germplasm.Food Chem 2009;113:640-4.
23.Zhang JS,Guan J,Yang FQ,Liu HG,Cheng XJ,Li SP,et al.Qualitative and quantitative analysis of four species of Curcuma rhizomes using twice development thin layer chromatography.J Pharm Biomed Anal2008;48:1024-8.
24.Li R,Xiang C,Ye M,Li HF,Zhang X,Guo DA,et al.Qualitative and quantitative analysis of curcuminoids in herbal medicines derived from Curcuma species.Food Chem 2011;126:1890-5.
25.Avula B,Wang YH,Khan IA.Quantitative determination of curcuminoids from the roots of Curcuma longa,Curcuma species and dietary supplements using an UPLC-UV-MS method.Planta Med 2009;3:1-6.
26.Chao IC,Wang CM,Li SP,Lin LG,Ye WC,Zhang QW,et al.Simultaneous quantification of three curcuminoids and three volatile components of Curcuma longa using pressurized liquid extraction and high-performance liquid chromatography.Molecules 2018;23.pii:E1568.
27.Long Y,Zhang W,Wang F,Chen Z.Simultaneous determination of three curcuminoids in Curcuma longa L.by high-performance liquid chromatography coupled with electrochemical detection.J Pharm Anal2014;4:325-30.
28.Osorio-Tobón JF,Carvalho PI,Barbero GF,Nogueira GC,Rostagno MA,Meireles MA,et al.Fast analysis of curcuminoids from turmeric(Curcuma longa L.)by high-performance liquid chromatography using a fused-core column.Food Chem 2016;200:167-74.
29.Shen Y,Han C,Chen X,Hou X,Long Z.Simultaneous determination of three curcuminoids in Curcuma Wenyujin Y.H.Chen et C.Ling.by liquid chromatography-tandem mass spectrometry combined with pressurized liquid extraction.J Pharm Biomed Anal 2013;81-82:146-50.
30.Ashraf K,Mujeeb M,Ahmad A,Ahmad N,Amir M.Determination of curcuminoids in Curcuma longa Linn.By UPLC/Q-TOF-MS:An application in turmeric cultivation.J Chromatogr Sci2015;53:1346-52.
31.Anubala S,Sekar R,Nagaiah K.Development and validation of an analytical method for the separation and determination of major bioactive curcuminoids in Curcuma longa rhizomes and herbal products using non-aqueous capillary electrophoresis.Talanta 2014;123:10-7.
32.Anubala S,Sekar R,Nagaiah K.Determination of curcuminoids and their degradation products in turmeric(Curcuma longa)rhizome herbal products by non-aqueous capillary electrophoresis with photodiode array detection.Food Anal Method 2016;9:2567-78.
33.Li F,Liu R,Yang F,Xiao W,Chen C,Xia ZN.Determination of three curcuminoids in Curcuma longa by microemulsion electrokinetic chromatography with protective effects on the analytes.Anal Methods2014;6:2566.
34.Chen SD,Chen JP,Chen F.Determination of inorganic elements in Curcuma longa by ICP-MS/ICP-AES.China Condiment 2010;8:102-4.
35.Chen JH,Tang YS,Liu DW,Wang NS.Residue determination of six kinds of heavy metal in rhizoma curcumae longae.Tradit Chin Drug Res Pharmacol 2009;20:457-60.