中药保健品中非法添加磷酸二酯酶-5抑制剂检测方法的研究进展
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摘要
本文综述了中药保健品中非法添加磷酸二酯酶-5(PDE-5)抑制剂的检测方法。目前,快速检测一般采用红外光谱法、近红外光谱法、薄层色谱与拉曼光谱联用法等;确证检测采用高效液相色谱法,液相色谱-质谱联用法等;在结构鉴别和确证上采用核磁共振法、气相色谱-质谱联用法等补充检测;还有一些X射线衍射、酶联免疫吸附等高效检测方法,为药品监督管理部门进行该类中药保健品掺杂的检测提供相关的技术方法,保障人民食品药品合理、安全的使用。
The detection methods for the illegal addition of PDE-5 inhibitors in botanical dietary supplements were reviewed in this article. So far,FTIR,NIR,and TLC-SERS methods were commonly adopted to rapid detection,and confirmed detection by HPLC,LC-MS methods; NMR and GC-MS methods were used as supplementary tests for structural identification and confirmation. In addition,other high-efficiency detection methods such as XRD and ELISA also provided relevant technical methods for the drug supervision and administration department to carry out the detection of the doping of botanical dietary supplements and ensure that the reasonable and safe use of food and drug.
The detection methods for the illegal addition of PDE-5 inhibitors in botanical dietary supplements were reviewed in this article. So far,FTIR,NIR,and TLC-SERS methods were commonly adopted to rapid detection,and confirmed detection by HPLC,LC-MS methods; NMR and GC-MS methods were used as supplementary tests for structural identification and confirmation. In addition,other high-efficiency detection methods such as XRD and ELISA also provided relevant technical methods for the drug supervision and administration department to carry out the detection of the doping of botanical dietary supplements and ensure that the reasonable and safe use of food and drug.
引文
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[3] VENHUIS B J,ZWAAGSTRA M E,VDB J D J,et al. Illicit erectile dysfunction products in the Netherlands :A decade of trends and a 2007-2010 product update[M].Netherlands: National Institate for Public Health and the Environment,2011.
[4] LOW M Y,ZENG Y,LI L,et al. Safety and quality assessment of 175 illegal sexual enhancement products seized in red-light districts in Singapore[J]. Drug Saf,2009,32(12):1141-1146.
[5] VENHUIS B J,DE KASTE D. Towards a decade of detecting new analogues of sildenafil,tadalafil and vardenafil in food supplements:a history,analytical aspects and health risks[J]. J Pharm Biomed Anal,2012,69:196-208.
[6] SHIN M H,HONG M K,KIM W S,et al. Identification of a new analogue of sildenafil added illegally to a functional food marketed for penile erectile dysfunction[J]. Food Addit Contam,2003,20(9):793-796.
[7] BLOK-TIP L,ZOMER B,BAKKER F,et al. Structure elucidation of sildenafil analogues in herbal products[J]. Food Addit Contam,2004,21(8):737-748.
[8] PARK H J,JEONG H K,CHANG M I,et al. Structure determination of new analogues of vardenafil and sildenafil in dietary supplements[J]. Food Addit Contam,2007,24(2):122-129.
[9] PARAMASHIVAPPA R,PHANI KUMAR P,SUBBA RAO PV,et al. Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition[J]. J Agric Food Chem,2002,50(26):7709-7713.
[10] CHAMPAGNE A B,EMMEL K V. Rapid screening test for adulteration in raw materials of dietary supplements[J]. Vibrational Spectroscopy,2011,55(2):216-223.
[11] VREDENBREGT M J,BLOK-TIP L,HOOGERBRUGGE R,et al. Screening suspected counterfeit Viagra and imitations of Viagra with near-infrared spectroscopy[J]. J Pharm Biomed Anal,2006,40(4):840-849.
[12] SAID M M,GIBBONS S,MOFFAT A C,et al. Rapid detection of sildenafil analogue in Eurycoma longifolia products using a new two-tier procedure of the near infrared (NIR) spectra database[J]. Food Chem,2014,158:296-301.
[13] GILARD V,BALAYSSAC S,TINAUGUS A,et al. Detection,identification and quantification by 1H NMR of adulterants in 150 herbal dietary supplements marketed for improving sexual performance[J]. J Pharm Biomed Anal,2015,102:476-493.
[14] 周建良,周哲,陈碧莲,等. UHPLC/LTQ Orbitrap MS法解析一种未知西地那非衍生物[J].质谱学报,2016,37(5):422-430.
[15] WOLLEIN U,EISENREICH W,SCHRAMEK N. Identification of novel sildenafil-analogues in an adulterated herbal food supplement[J]. J Pharm Biomed Anal,2011,56(4):705-712.
[16] CAI Y,CAI T G,SHI Y,et al. Simultaneous determination of eight PDE5-IS potentially adulterated in herbal dietary supplements with TLC and HPLC–PDA–MS methods[J]. J Liq Chromatogr Relat Technol,2010,33(13):1287-1306.
[17] ABOURASHED E,ABDEL-KADER M,HABIB A A. HPTLC determination of sildenafil in pharmaceutical products and aphrodisiac herbal preparations[J]. J Plan Chromatogr Modern TLC,2005,18(105):372-376.
[18] 张振华,陶妙娟. 四种中成药及保健品非法添加化学药物的快递筛选方法初探[J].安徽医药,2008,12(1):28-29.
[19] REDDY T,REDDY A,DEVI P. Quantitative determination of sildenafil citrate in herbal medicinal formulations by high-performance thin-layer chromatography[J]. J Plan Chromatogr Modern TLC,2006,19(112):427-431.
[20] LV D,CAO Y,LOU Z,et al. Rapid on-site detection of ephedrine and its analogues used as adulterants in slimming dietary supplements by TLC-SERS[J]. Anal Bioanal Chem,2015,407(5):1313-1325.
[21] 李皓,朱青霞,柴逸峰,等. TLC-SERS法快速检测止咳平喘类中成药中4种添加化学成分[J].药物分析杂志,2014,34(4):693-697.
[22] ZHU Q,CAO Y,CAO Y,et al. Rapid on-site TLC-SERS detection of four antidiabetes drugs used as adulterants in botanical dietary supplements[J]. Anal Bioanal Chem,2014,406(7):1877-1884.
[23] 李启红.中药及保健品中非法添加3种PDE5抑制剂的TLC-SERS检测方法研究[J].中国当代医药,2017,24(21):85-88.
[24] LIU S Y,WOO S O,KOH H L. HPLC and GC-MS screening of Chinese proprietary medicine for undeclared therapeutic substances[J]. J Pharm Biomed Anal,2001,24(5-6):983-992.
[25] FEJ?S I,NEUMAJER G,BéNI S,et al. Qualitative and quantitative analysis of PDE-5 inhibitors in counterfeit medicines and dietary supplements by HPLC-UV using sildenafil as a sole reference[J]. J Pharm Biomed Anal,2014,98:327-333.
[26] DONG Y M,AN Q,LU N W,et al. Development micellar HPLC method for simultaneous determination of ephedrine,pseudoephedrine,and methylephedrine in Ephedra Herb and traditional Chinese medicinal preparations[J]. Acta Chromatographica,2015,27(2):355-372.
[27] SACRé P Y,DECONINCK E,CHIAP P,et al. Development and validation of a ultra-high-performance liquid chromatography-UV method for the detection and quantification of erectile dysfunction drugs and some of their analogues found in counterfeit medicines[J]. J Chromatogr A,2011,1218(37):6439-6447.
[28] SINGH S,PRASAD B,SAVALIYA A,et al. Strategies for characterizing sildenafil,vardenafil,tadalafil and their analogues in herbal dietary supplements,and detecting counterfeit products containing these drugs[J]. Trends Analyt Chem,2009,28(1):13-28.
[29] ZOU P,OH S S,HOU P,et al. Simultaneous determination of synthetic phosphodiesterase-5 inhibitors found in a dietary supplement and pre-mixed bulk powders for dietary supplements using high-performance liquid chromatography with diode array detection and liquid chromatography-electrospray ionization tandem mass spectrometry[J]. J Chromatogr A,2006,1104(1):113-122.
[30] 于泓,胡青,张甦,等. 补肾壮阳类中药及保健食品中31种5型磷酸二酯酶抑制剂的高分辨四级杆飞行时间质谱定性定量检测方法[J],中国药学杂志2013,48(15):1312-1318.
[31] MOKHTAR S U,CHIN S T,KEE C L,et al. Rapid determination of sildenafil and its analogues in dietary supplements using gas chromatography-triple quadrupole mass spectrometry[J]. J Pharm Biomed Anal,2016,121:188-196.
[32] REEPMEYER J C,WOODRUFF J T. Use of liquid chromatography-mass spectrometry and a chemical cleavage reaction for the structure elucidation of a new sildenafil analogue detected as an adulterant in an herbal dietary supplement[J]. J Pharm Biomed Anal,2007,44(4):887-893.
[33] REEPMEYER J C,WOODRUFF J T,D'AVIGNON D A. Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement[J]. J Pharm Biomed Anal,2007,43(5):1615-1621.
[34] REEPMEYER J C,D'AVIGNON D A. Structure elucidation of thioketone analogues of sildenafil detected as adulterants in herbal aphrodisiacs[J]. J Pharm Biomed Anal,2009,49(1):145-150.
[35] MOJZYCH M,KARCZMARZYK Z,WYSOCKI W,et al. New approaches to the synthesis of sildenafil analogues and their enzyme inhibitory activity[J]. Bioorg Med Chem,2015,23(7):1421-1429.
[36] MOJZYCH M,KARCZMARZYK Z,WYSOCKI W,et al. New approaches to the synthesis of sildenafil analogues and their enzyme inhibitory activity[J]. Bioorg Med Chem,2015,23(7):1421-1429.
[37] ORTIZ R S,MARIOTTI K C,SCHWAB N V,et al. Fingerprinting of sildenafil citrate and tadalafil tablets in pharmaceutical formulations via X-ray fluorescence (XRF) spectrometry[J]. J Pharm Biomed Anal,2012,58:7-11.
[38] PERR J M,FURTON K G,ALMIRALL J R. Solid phase microextraction ion mobility spectrometer interface for explosive and taggant detection[J]. J Sep Sci,2005,28(2):177-183.
[39] MANS D J,CALLAHAN R J,DUNN J D,et al. Rapid-screening detection of acetildenafils,sildenafils and avanafil by ion mobility spectrometry[J]. J Pharm Biomed Anal,2013,75:153-157.
[40] GUO J B,XU Y,HUANG Z B,et al. Development of an immunoassay for rapid screening of vardenafil and its potential analogues in herbal products based on a group specific monoclonal antibody[J]. Anal Chim Acta,2010,658(2):197-203.
[41] SONG Y,WANG Y Y,ZHANG Y,et al. Development of enzyme-linked immunosorbent assay for rapid determination of sildenafil in adulterated functional foods[J]. Food Agric Immunol,2012,23(4):338-351.
[2] SUGITA M,MIYAKAWA M. Economic analysis of use of counterfeit drugs:health impairment risk of counterfeit phosphodiesterase type 5 inhibitor taken as an example[J]. Environ Health Prev Med,2010,15(4):244-251.
[3] VENHUIS B J,ZWAAGSTRA M E,VDB J D J,et al. Illicit erectile dysfunction products in the Netherlands :A decade of trends and a 2007-2010 product update[M].Netherlands: National Institate for Public Health and the Environment,2011.
[4] LOW M Y,ZENG Y,LI L,et al. Safety and quality assessment of 175 illegal sexual enhancement products seized in red-light districts in Singapore[J]. Drug Saf,2009,32(12):1141-1146.
[5] VENHUIS B J,DE KASTE D. Towards a decade of detecting new analogues of sildenafil,tadalafil and vardenafil in food supplements:a history,analytical aspects and health risks[J]. J Pharm Biomed Anal,2012,69:196-208.
[6] SHIN M H,HONG M K,KIM W S,et al. Identification of a new analogue of sildenafil added illegally to a functional food marketed for penile erectile dysfunction[J]. Food Addit Contam,2003,20(9):793-796.
[7] BLOK-TIP L,ZOMER B,BAKKER F,et al. Structure elucidation of sildenafil analogues in herbal products[J]. Food Addit Contam,2004,21(8):737-748.
[8] PARK H J,JEONG H K,CHANG M I,et al. Structure determination of new analogues of vardenafil and sildenafil in dietary supplements[J]. Food Addit Contam,2007,24(2):122-129.
[9] PARAMASHIVAPPA R,PHANI KUMAR P,SUBBA RAO PV,et al. Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition[J]. J Agric Food Chem,2002,50(26):7709-7713.
[10] CHAMPAGNE A B,EMMEL K V. Rapid screening test for adulteration in raw materials of dietary supplements[J]. Vibrational Spectroscopy,2011,55(2):216-223.
[11] VREDENBREGT M J,BLOK-TIP L,HOOGERBRUGGE R,et al. Screening suspected counterfeit Viagra and imitations of Viagra with near-infrared spectroscopy[J]. J Pharm Biomed Anal,2006,40(4):840-849.
[12] SAID M M,GIBBONS S,MOFFAT A C,et al. Rapid detection of sildenafil analogue in Eurycoma longifolia products using a new two-tier procedure of the near infrared (NIR) spectra database[J]. Food Chem,2014,158:296-301.
[13] GILARD V,BALAYSSAC S,TINAUGUS A,et al. Detection,identification and quantification by 1H NMR of adulterants in 150 herbal dietary supplements marketed for improving sexual performance[J]. J Pharm Biomed Anal,2015,102:476-493.
[14] 周建良,周哲,陈碧莲,等. UHPLC/LTQ Orbitrap MS法解析一种未知西地那非衍生物[J].质谱学报,2016,37(5):422-430.
[15] WOLLEIN U,EISENREICH W,SCHRAMEK N. Identification of novel sildenafil-analogues in an adulterated herbal food supplement[J]. J Pharm Biomed Anal,2011,56(4):705-712.
[16] CAI Y,CAI T G,SHI Y,et al. Simultaneous determination of eight PDE5-IS potentially adulterated in herbal dietary supplements with TLC and HPLC–PDA–MS methods[J]. J Liq Chromatogr Relat Technol,2010,33(13):1287-1306.
[17] ABOURASHED E,ABDEL-KADER M,HABIB A A. HPTLC determination of sildenafil in pharmaceutical products and aphrodisiac herbal preparations[J]. J Plan Chromatogr Modern TLC,2005,18(105):372-376.
[18] 张振华,陶妙娟. 四种中成药及保健品非法添加化学药物的快递筛选方法初探[J].安徽医药,2008,12(1):28-29.
[19] REDDY T,REDDY A,DEVI P. Quantitative determination of sildenafil citrate in herbal medicinal formulations by high-performance thin-layer chromatography[J]. J Plan Chromatogr Modern TLC,2006,19(112):427-431.
[20] LV D,CAO Y,LOU Z,et al. Rapid on-site detection of ephedrine and its analogues used as adulterants in slimming dietary supplements by TLC-SERS[J]. Anal Bioanal Chem,2015,407(5):1313-1325.
[21] 李皓,朱青霞,柴逸峰,等. TLC-SERS法快速检测止咳平喘类中成药中4种添加化学成分[J].药物分析杂志,2014,34(4):693-697.
[22] ZHU Q,CAO Y,CAO Y,et al. Rapid on-site TLC-SERS detection of four antidiabetes drugs used as adulterants in botanical dietary supplements[J]. Anal Bioanal Chem,2014,406(7):1877-1884.
[23] 李启红.中药及保健品中非法添加3种PDE5抑制剂的TLC-SERS检测方法研究[J].中国当代医药,2017,24(21):85-88.
[24] LIU S Y,WOO S O,KOH H L. HPLC and GC-MS screening of Chinese proprietary medicine for undeclared therapeutic substances[J]. J Pharm Biomed Anal,2001,24(5-6):983-992.
[25] FEJ?S I,NEUMAJER G,BéNI S,et al. Qualitative and quantitative analysis of PDE-5 inhibitors in counterfeit medicines and dietary supplements by HPLC-UV using sildenafil as a sole reference[J]. J Pharm Biomed Anal,2014,98:327-333.
[26] DONG Y M,AN Q,LU N W,et al. Development micellar HPLC method for simultaneous determination of ephedrine,pseudoephedrine,and methylephedrine in Ephedra Herb and traditional Chinese medicinal preparations[J]. Acta Chromatographica,2015,27(2):355-372.
[27] SACRé P Y,DECONINCK E,CHIAP P,et al. Development and validation of a ultra-high-performance liquid chromatography-UV method for the detection and quantification of erectile dysfunction drugs and some of their analogues found in counterfeit medicines[J]. J Chromatogr A,2011,1218(37):6439-6447.
[28] SINGH S,PRASAD B,SAVALIYA A,et al. Strategies for characterizing sildenafil,vardenafil,tadalafil and their analogues in herbal dietary supplements,and detecting counterfeit products containing these drugs[J]. Trends Analyt Chem,2009,28(1):13-28.
[29] ZOU P,OH S S,HOU P,et al. Simultaneous determination of synthetic phosphodiesterase-5 inhibitors found in a dietary supplement and pre-mixed bulk powders for dietary supplements using high-performance liquid chromatography with diode array detection and liquid chromatography-electrospray ionization tandem mass spectrometry[J]. J Chromatogr A,2006,1104(1):113-122.
[30] 于泓,胡青,张甦,等. 补肾壮阳类中药及保健食品中31种5型磷酸二酯酶抑制剂的高分辨四级杆飞行时间质谱定性定量检测方法[J],中国药学杂志2013,48(15):1312-1318.
[31] MOKHTAR S U,CHIN S T,KEE C L,et al. Rapid determination of sildenafil and its analogues in dietary supplements using gas chromatography-triple quadrupole mass spectrometry[J]. J Pharm Biomed Anal,2016,121:188-196.
[32] REEPMEYER J C,WOODRUFF J T. Use of liquid chromatography-mass spectrometry and a chemical cleavage reaction for the structure elucidation of a new sildenafil analogue detected as an adulterant in an herbal dietary supplement[J]. J Pharm Biomed Anal,2007,44(4):887-893.
[33] REEPMEYER J C,WOODRUFF J T,D'AVIGNON D A. Structure elucidation of a novel analogue of sildenafil detected as an adulterant in an herbal dietary supplement[J]. J Pharm Biomed Anal,2007,43(5):1615-1621.
[34] REEPMEYER J C,D'AVIGNON D A. Structure elucidation of thioketone analogues of sildenafil detected as adulterants in herbal aphrodisiacs[J]. J Pharm Biomed Anal,2009,49(1):145-150.
[35] MOJZYCH M,KARCZMARZYK Z,WYSOCKI W,et al. New approaches to the synthesis of sildenafil analogues and their enzyme inhibitory activity[J]. Bioorg Med Chem,2015,23(7):1421-1429.
[36] MOJZYCH M,KARCZMARZYK Z,WYSOCKI W,et al. New approaches to the synthesis of sildenafil analogues and their enzyme inhibitory activity[J]. Bioorg Med Chem,2015,23(7):1421-1429.
[37] ORTIZ R S,MARIOTTI K C,SCHWAB N V,et al. Fingerprinting of sildenafil citrate and tadalafil tablets in pharmaceutical formulations via X-ray fluorescence (XRF) spectrometry[J]. J Pharm Biomed Anal,2012,58:7-11.
[38] PERR J M,FURTON K G,ALMIRALL J R. Solid phase microextraction ion mobility spectrometer interface for explosive and taggant detection[J]. J Sep Sci,2005,28(2):177-183.
[39] MANS D J,CALLAHAN R J,DUNN J D,et al. Rapid-screening detection of acetildenafils,sildenafils and avanafil by ion mobility spectrometry[J]. J Pharm Biomed Anal,2013,75:153-157.
[40] GUO J B,XU Y,HUANG Z B,et al. Development of an immunoassay for rapid screening of vardenafil and its potential analogues in herbal products based on a group specific monoclonal antibody[J]. Anal Chim Acta,2010,658(2):197-203.
[41] SONG Y,WANG Y Y,ZHANG Y,et al. Development of enzyme-linked immunosorbent assay for rapid determination of sildenafil in adulterated functional foods[J]. Food Agric Immunol,2012,23(4):338-351.