Simultaneous determination of eight PDE5-IS potentially adulterated in herbal dietary supplements with TLC and HPLC-PDA-MS methods

Journal of Liquid Chromatography and Related Technologies

Volumn 33, Issue 13, 2010, Pages 1287-1306

  Cai, Yu ^a   Cai, Tian Ge ^b   Shi, Yan ^c   Cheng, Xian Long ^c   Ma, Ling Yun ^c   Ma, Shuang Cheng ^c   Lin, Rui Chao ^c   Feng, Wei ^c  

^a JINAN UNIVERSITY   (China)

^b LIAONING UNIVERSITY   (China)

^c National Institute for the Control of Pharmaceutical Biological Products   (China)

Author keywords

DE5 Is; determination; herbal dietary supplements; HPLC PDA MS; PDE5 Is; TLC

Indexed keywords

DE5-IS; DETERMINATION; HERBAL DIETARY SUPPLEMENTS; HPLC- PDA; PDE5-IS; TLC;

NUTRITION; VITAMINS;

FOOD ADDITIVES;

AMINOTADALAFIL; BODLII; ENHANIX; HERB POWER; HERBACEOUS AGENT; HERBAL MAX; HERBAL STRON; HOLEXUM; HOMOSILDENAFIL; HONGDENAFIL; HUOLONG; HYDROXYHOMOSILDENAFIL; LQSH; PHOSPHODIESTERASE V INHIBITOR; POWER 9; PSEUDOVARDENAFIL; SANBIAN; SILDENAFIL; TADALAFIL; UNCLASSIFIED DRUG; VARDENAFIL;

ARTICLE; CORDYCEPS; CORNUS; CUSCUTA; DIET SUPPLEMENTATION; DRUG FORMULATION; DRUG IMPURITY; DRUG STRUCTURE; ECHINACEA PURPUREA; GANODERMA; GINSENG; HERBAL MEDICINE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; JUJUBE; MASS SPECTROMETRY; MORINDA; PIPER METHYSTICUM; PUERARIA; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; SABAL; SCHISANDRACEAE; SENSITIVITY AND SPECIFICITY; THIN LAYER CHROMATOGRAPHY;

EID: 77956052546     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826076.2010.488979     Document Type: Article

References (56)

1. Porst, H. IC351 (tadalafil, Cialis): Update on Clinical Experience. Int. J. Impot. Res. 2002, 14 (1), 57-64.
2. Kuan, J.; Brock, G. Selective Phosphodiesterase Type 5 Inhibition Using Tadalafilfor the Treatment of Erectile Dysfunction. Expert Opin. Investig. Drugs. 2002, 11 (11), 1605-1613.
3. Wespes, E.; Amar, E.; Hatzichristou, D.; Montorsi, F.; Pryor, J.; Vardi, Y. Guidelines on Erectile Dysfunction. Eur. Urol. 2002, 41 (1), 1-5.
4. Hicklin, L. A.; Ryan, C.; Wong, D. K.; Hinton, A. E. Nose-bleeds After Sildenafil (Viagra). J. R. Soc. Med. 2002, 95 (8), 402-403.
5. Weinmann, W.; Bohnert, M.; Wiedemann, A.; Renz, M.; Lehmann, N.; Pollak, S. Post-mortem Detection and Identification of Sildenafil (Viagra) and its Metabolites by LC=MS and LC=MS= MS. Int. J. Legal. Med. 2001, 114 (4-5), 252-258.
6. Xueyi, Z.; Zhonghu, Z.; Feng, L.; Yutian, W.; Yunpeng, Q. Modified Local Straight-Line Screening to Detect Synthetic Drugs in Adulterated Herbal Medicines. Appl. Spectrosc. 2009, 63 (4), 471-476.
7. Tseng, M. C.; Li, J. H. Determination of Sildenafil Citrate Adulterated in a Dietary Supplements. J. Food Drug Anal. 2002, 10 (2), 112-119.
8. Mikami, E.; Ohno, T.; Matsumoto, H. Simultaneous Identification= Determination System for Phentolamine and Sildenafil as Adulterants in Soft Drinks Advertising Roborant Nutrition. Forensic Sci. Int. 2002, 130 (2-3), 140-146.
9. Fleshner, N.; Harvey, M.; Adomat, H.; Wood, C.; Eberding, A.; Hersey, K.; Guns, E. Evidence for Contamination of Herbal Erectile Dysfunction Products with Phosphodiesterase Type 5 Inhibitors. J. Urol. 2005, 174 (2), 636-641.
10. Zhu, X.; Xiao, S.; Chen, B.; Zhang, F.; Yao, S.; Wan, Z.; Yang, D.; Han, H. Simultaneous Determination of Sildenafil, Vardenafil and Tadalafil as Forbidden Components in Natural Dietary Supplements for Male Sexual Potency by High-Performance Liquid Chromatography-Electrospray Ionization Mass Spectrometry. J. Chromatogr. A. 2005, 1066 (1-2), 89-95.
11. Liang, Q.; Qu, J.; Luo, G.;Wang, Y. Rapid and Reliable Determination of Illegal Adulterant in Herbal Medicines and Dietary Supplements by LC=MS=MS. J. Pharm. Biomed. Anal. 2006, 40 (2), 305-311.
12. Bogusz, M. J.; Hassan, H.; Al-Enazi, E.; Ibrahim, Z.; Al-Tufail, M. Application of LC-ESI-MS-MS for Detection of Synthetic Adulterants in Herbal Remedies. J. Pharm. Biomed. Anal. 2006, 41 (2), 554-564.
13. Abdel, H. M. Determination of Sildenafil, Tadalafil, and Vardenafil in Tablets and Adulterated Herbal Products by ESI-MS-MS. J. Liquid Chromatogr. 2006, 29, 591-603.
14. Gratz, S. R.; Flurer, C. L.; Wolnik, K. A. Analysis of Undeclared Synthetic Phosphodiesterase-5 Inhibitors in Dietary Supplements and Herbal Matrices by LC-ESI-MS and LC-UV. J. Pharm. Biomed. Anal. 2004, 36 (3), 525-533.
15. Shin, M. H.; Hong, M. K.; Kim, W. S.; Lee, Y. J.; Jeoung, Y. C. Identification of a New Analogue of Sildenafil Added Illegally to a Functional Food Marketed for Penile Erectile Dysfunction. Food Addit. Contam. 2003, 20 (9), 793-796.
16. Blok-Tip, L.; Zomer, B.; Bakker, F.; Hartog, K. D.; Hamzink, M.; Hove, J.; Vredenbregt, M.; De, Kaste, D. Structure Elucidation of Sildenafil Analogues in Herbal Products. Food Addit. Contam. 2004, 21 (8), 737-748.
17. Zou, P.; Oh, S. S.; Hou, P.; Low, M. Y.; Koh, H. L. 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. Chromatogr. A. 2006, 1104 (1-2), 113-122.
18. Oh, S. S.; Zou, P.; Low, M. Y.; Koh, H. L. Detection of Sildenafil Analogues in Herbal Products for Erectile Dysfunction. J. Toxicol. Environ. Health A. 2006, 69 (21), 1951-1958.
19. Shin, C.; Hong, M.; Kim, D.; Lim, Y. Structure Determination of a Sildenafil Analogue Contained in Commercial Herb Drinks. Magn. Reson. Chem. 2004, 42 (12), 1060-1062.
20. Lai, K. C.; Liu, Y. C.; Tseng, M. C.; Lin, J. H. Isolation and Identification of a Sildenafil Analogue Illegally Added in Dietary Supplements. J. Food Drug Anal. 2006, 14, 19-23.
21. Hou, P.; Zou, P.; Low, M. Y.; Chan, E.; Koh, H. L. Structural Identification of a New Acetildenafil Analogue from Pre-Mixed Bulk Powder Intended as a Dietary Supplement. Food Addit. Contam. 2006, 23 (9), 870-875.
22. Gratz, S. R.; Gamble, B. M.; Flurer, R. A. Accurate Mass Measurement Using Fourier Transform Ion Cyclotron Resonance Mass Spectrometry for Structure Elucidation of Designer Drug Analogs of Tadalafil, Vardenafil and Sildenafil in Herbal and Pharmaceutical Matrices. Rapid Commun. Mass Spectrom. 2006, 20 (15), 2317-2327.
23. Zou, P.; Hou, P.; Low, M. Y.; Koh, H. L. Structural Elucidation of a Tadalafil Analogue Found as an Adulterant of an Herbal Product. Food Addit. Contam. 2006, 23 (5), 446-451.
24. Zou, P.; Hou, P.; Oh, S. S.; Low, M. Y.; Koh, H. L. Electrospray Tandem Mass Spectrometric Investigations of Tadalafil and its Analogue. Rapid Commun. Mass Spectrom. 2006, 20 (22), 3488-3490.
25. Reepmeyer, J. C.; Woodruff, J. T. Use of Liquid Chromatography-Mass Spectrometry and a Hydrolytic Technique for the Detection and Structure Elucidation of a Novel Synthetic Vardenafil Designer Drug Added Illegally to a ''Natural'' Herbal Dietary Supplement. J. Chromatogr. A. 2006, 1125 (1), 67-75.
26. Gao, Q.; Zhang, Z.; Guo, H. Z.; Dai, H.; Che, B. Q.; Wang, Z. B. Study on PDE-5 Inhibitors and Its Unknown Derivatives in Traditional Chinese Medicine and Health Food Discovered. Chin. Pharm. J. 2008, 43, 142-146.
27. Zou, P.; Hou, P.; Oh, S. S.; Chong, Y. M.; Bloodworth, B. C.; Low, M. Y.; Koh, H. L. Isolation and Identification of Thiohomosildenafil and Thiosildenafil in Health Supplements. J. Pharm. Biomed. Anal. 2008, 47 (2), 279-284.
28. Reepmeyer, J. C.; d'Avignon, D. A. Structure Elucidation of Thioketone Analogues of Sildenafil Detected as Adulterants in Herbal Aphrodisiacs. J. Pharm. Biomed. Anal. 2009, 49 (1), 145-150.
29. Takashi, H.; Kazunaga, T.; Masaaki, S.; Toshiyasu, I.; Tomoko, N.; Masaaki, K.; Yuji, H.; Yukihiro, G.; Nobuo, K. Isolation and Structural Elucidation of Cyclopentynafil and N-Octylnortadalafil Found in a Dietary Supplement. Chem. Pharm. Bull. 2009, 57 (2), 185-189.
30. Nagaraju, V.; Sreenath, D.; Rao, J. T.; Rao, R. N. Separation and Determination of Synthetic Impurities of Sildenafil (Viagra) by Reversed-Phase High-Performance Liquid Chromatography. Anal. Sci. 2003, 19 (7), 1007-1011.
31. Joo, Y. C.; Hyeong, S. L.; Kyung, S. Y.; Hyun, J. S.; In, J. J.; Sang, G. S. Sensitive Liquid Chromatography Assay with Ultraviolet Detection for a New Phosphodiesterase V Inhibitor, DA-8159, in Human Plasma and Urine. J. Chromatogr. B, 2003, 795 (2), 179-186.
32. Cooper, J. D.; Muirhead, D. C.; Taylor, J. E.; Baker, P. R. Development of an Assay for the Simultaneous Determination of Sildenafil (Viagra) and its Metabolite (UK-103,320) Using Automated Sequential Trace Enrichment of Dialysates and High-Performance Liquid Chromatography. J. Chromatogr. B. 1997, 701, 87-95.
33. Lia, J.; Chang, T. W. Determination of Transdermal Sildenafil in Nude Mouse Skin by Reversed- Phase High-Performance Liquid Chromatography. J. Chromatogr. B. 2001, 765, 161-166.
34. Ming, T. S.; An, B.W.; Geng, C. Y.; Angel, H.; Hsiu, O. H. Development of a Liquid Chromatographic Method for Bioanalytical Applications with Sildenafil. J. Chromatogr. B. 2003, 791 (1-2), 255-262.
35. Dinesh, N. D.; Vishukumar, B. K.; Nagaraja, P.; Gowda, N. M.; Rangappa, K. S. Stability Indicating RP-LC Determination of Sildenafil Citrate (Viagra) in Pure Form and in Pharmaceutical Samples. J. Pharm. Biomed. Anal. 2002, 29, 743.
36. Angela, E.; Tom, A.; Weng, N. D. Simultaneous Assay of Sildenafil and Desmethylsildenafil in Human Plasma using Liquid Chromatography-Tandem Mass Spectrometry on Silica Column with Aqueous-Organic Mobile Phase. J. Chromatogr. B. 2002, 768 (2), 277-284.
37. Tracqui, A.; Ludes, B.HPLC-MS for the Determination of Sildenafil Citrate (Viagra) in Biological Fluids. Application to the Salivary Excretion of Sildenafil After Oral Intake. J. Anal. Toxicol. 2003, 27 (2), 88-94.
38. Fleshner, N.; Harvey, M.; Adomat, H.; Wood, C.; Eberding, A.; Hersey, K.; Guns, E. Evidence for Contamination of Herbal Erectile Dysfunction Products with Phosphodiesterase Type 5 Inhibitors. J. Urol. 2005, 174 (2), 636-641.
39. 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. Pharm. Biomed. Anal. 2007, 44 (4), 887-893.
40. Venhuis, B. J.; Blok, T. L.; de Kaste, D. Designer Drugs in Herbal Aphrodisiacs. Forensic Sci. Int. 2008, 177 (2-3), 25-27.
41. 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. Pharm. Biomed. Anal. 2007, 43 (5), 1615-1621.
42. Park, H. J.; Jeong, H. K.; Chang, M. I.; Im, M. H.; Jeong, J. Y.; Choi, D. M.; Park, K.; Hong, M. K.; Youm, J.; Han, S. B.; Kim, D. J.; Park, J. H.; Kwon, S. W. Structure Determination of New Analogues of Vardenafil and Sildenafil in Dietary Supplements. Food Addit. Contam. 2007, 24 (2), 122-129.
43. Lam, Y. H.; Poon, W. T.; Lai, C. K.; Chan, A. Y.; Mak, T. W. Identification of a Novel Vardenafil Analogue in Herbal Product. J. Pharm. Biomed. Anal. 2008, 46 (4), 804-807.
44. Venhuis, B. J.; Zomer, G.; de Kaste, D. Structure Elucidation of a Novel Synthetic Thiono Analogue of Sildenafil Detected in an Alleged Herbal Aphrodisiac. J. Pharm. Biomed. Anal. 2008, 46 (4), 814-817.
45. Miller, G. M.; Stripp, R. A. Study of Western Pharmaceuticals Contained within Samples of Chinese Herbal=Patent Medicines Collected from New York City's Chinatown. Leg. Med. (Tokyo). 2007, 9 (5), 258-264.
46. Vos, R. M.; Chahbouni, A.; Sinjewel, A.; Swart, E. L. Quantitative Analysis of Sildenafil and Desmethylsildenafil in Human Serum by Liquid Chromatography-Mass Spectrometry with Minimal Sample Pretreatment. J. Chromatogr. B. 2008, 876 (2), 283-287.
47. Bae, S. K.; Kang, M. J.; Yeo, C. W.; Kim, M. J.; Shon, J. H.; Liu, K. H.; Shin, J. G. Simultaneous Determination of Udenafil and Its Active Metabolite, DA-8164, IN Human Plasma and Urine Using Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry: Application to a Pharmacokinetic Study. Biomed. Chromatogr. 2008, 22 (9), 939-946.
48. Guermouche, M. H.; Bensalah, K. Solid Phase Extraction and Liquid Chromatographic Determination of Sildenafil and N-Demethylsildenafil in Rat Serum with Basic Mobile Phase. J. Pharm. Biomed. Anal. 2006, 40 (4), 952-957.
49. Pistos, C.; Papoutsis, I.; Dona, A.; Stefanidou, M.; Athanaselis, S.; Maravelias, C.; Spiliopoulou, C. Off-line HPLC Method Combined to LC-MS for the Determination of Sildenafil and its Active Metabolite in Post-Mortem Human Blood According to Confirmation Criteria. Forensic Sci. Int. 2008, 178 (2-3), 192-198.
50. Hei, Y. K.; Ji, H. S.; Kwang, H. L.; Jae, G. S.; Soo, K. B. Liquid Chromatography=Tandem Mass Spectrometry Method for the Simultaneous Determination of Vardenafil and Its Major Metabolite, N-Desethylvardenafil, in Human Plasma: Application to a Pharmacokinetic Study. J. Chromatogr. B. 2009, 877 (1-2), 95-100.
51. Li, R. K.; Bo, T.; Liu, H. W.; Li, K. A. Determination of Sildenafil in Medicines for Erectile Dysfunction by Capillary Electrophoresis. Se Pu. 2002, 4, 49-51.
52. Berzas, N. J.; Flores, J. R.; Peñalvo, G. C.; Rodríguez, F. N. Determination of Sildenafil Citrate and its Main Metabolite by Sample Stacking with Polarity Switching Using Micellar Electrokinetic Chromatography. J. Chromatogr. A. 2002, 953 (1-2), 279-286.
53. Gryniewicz, C. M.; Reepmeyer, J. C.; Kauffman, J. F.; Buhse, L. F. Detection of Undeclared Erectile Dysfunction Drugs and Analogues in Dietary Supplements by Ion Mobility Spectrometry. J. Pharm. Biomed. Anal. 2009, 49 (3), 601-606.
54. Dong, M.; Sangaeh, P.; Tae, H. Y.; Hye, K. J.; Jae, S. P.; Janghyun, P.; Deukjoon, K.; Sung, W. K. Determination of Analogs of Sildenafil and Vardenafil in Foods by Column Liquid Chromatography with a Photodiode Array Detector, Mass Spectrometry, and Nuclear Magnetic Resonance Spectrometry. J. AOAC Inter. 2008, 91 (3), 580-588.
55. Poon, W. T.; Lam, Y. H.; Lai, C. K.; Albert, Y. W.; Chan, A. Y.; Tony, W. M. Analogues of Erectile Dysfunction Drugs: An Under-Recognized Threat. Hong Kong Med. J. 2007, 13 (5), 359-363.
56. Cockburn, R.; Newton, P. N.; Agyarko, E. K.; Akunyili, D.; White, N. J. The global Threat of Counterfeit Drugs: Why Industry and Governments Must Communicate the Dangers. PLoS Med. 2005, 2 (4), 100.