Isolation and identification of hydroxythiohomosildenafil in herbal dietary supplements sold as sexual performance enhancement products

Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment

Volumn 26, Issue 2, 2009, Pages 145-151

  Li, L ^a   Low, M Y ^b   Aliwarga, F ^a   Teo, J ^b   Ge, X W ^b   Zeng, Y ^b   Bloodworth, B C ^b   Koh, H L ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b HEALTH SCIENCES AUTHORITY   (Singapore)

Author keywords

Adulteration; Erectile dysfunction; Hydroxythiohomosildenafil; PDE 5 inhibitors

Indexed keywords

HERBACEOUS AGENT; HYDROXYTHIOHOMOSILDENAFIL; LFW; MAXIDUS; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DIET SUPPLEMENTATION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG SAFETY; DRUG STRUCTURE; ERECTILE DYSFUNCTION; INFRARED RADIATION; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SEXUAL FUNCTION; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET RADIATION;

EID: 59849105540     PISSN: 19440049     EISSN: 19440057     Source Type: Journal    
DOI: 10.1080/02652030802368757     Document Type: Article

References (25)

1. Ang, HH, Ngai, TH, and Tan, TH. 2003. Effects of Eurycoma longifolia Jack on sexual qualities in middle aged male rats. Phytomedicine, 10:590–593.
2. BioGulf Store®. 2008a. Maxidus, Malaysia:BioGulf Store. Available:http://www.biogulfstore.com/v2/product_info.php?cPath=21&products_id=53. Accessed:10 March 2008
3. BioGulf Store®. 2008b. Libidus for women, Malaysia:BioGulf Store. Available:http://www.biogulfstore.com/v2/product_info.php?cPath=22&products_id=33. Accessed:10 March 2008
4. Blok-Tip, L, Zomer, B, Bakker, F, Hartog, KD, Hamzink, M, Ten Hove, J, Vredenbregt, M, and De Kaste, D. 2004. Structure elucidation of sildenafil analogues in herbal products. Food Addit Contam, 21:737–748.
5. Chan, KL, Lee, SP, Sam, TW, and Han, BH. 1989. A quassinoid glycoside from the roots of Eurycoma longifolia. Phytochemistry, 28:2857–2859.
6. Chen, X, Ji, H, Wang, Y, and Li, S. 2008. Simultaneous determination of seven flavonoids in Epimedium using pressurized liquid extraction and capillary electrochromatography. J Sep Sci, 31:881–887.
7. Fernandes, NPC, Lagishetty, CV, Panda, VS, and Naik, SR. 2007. An experimental evaluation of the antidiabetic and antilipidemic properties of a standardized Momordica charantia fruit extract. BMC Complement Altern Med, 7:29
8. Gratz, SR, Gamble, BM, and Flurer, RA. 2006. 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, 20:2317–2327.
9. Health Sciences Authority of Singapore. 2008a. HSA alerts on wider spread of harmful illegal health products, Singapore:Health Sciences Authority of Singapore. Available:http://www.hsa.gov.sg/publish/etc/medialib/hsa_library/corporate/pr20072009.Par.50960.File.tmp/PressRelease-HSAAlertsOnWiderSpreadOfHarmfulIllegalHealthProducts-11Apr2008.pdf. Accessed:20 March 2008
10. Health Sciences Authority of Singapore. 2008b. HSA updates on serious adverse reaction cases associated with harmful illegal health products, Singapore:Health Sciences Auth-ority of Singapore. Available:http://www.hsa.gov.sg/publish/hsaportal/en/news_events/press_releases/2008.-hsaArticleBody-45903-DownloadFile.tmp/HSAPressRelease-HSAUpdatesOnSeriousAdverseReactionCasesAssociatedWithHarmfulIllegalHealthProducts-25Apr2008.pdf. Accessed:20 March 2008
11. Health Sciences Authority of Singapore. 2008c. HSA updates on fatalities & serious adverse reactions associated with the use of illegal health products, Singapore:Health Sciences Authority of Singapore. Available:http://www.hsa.gov.sg/publish/etc/medialib/hsa_library/corporate/pr20072009.Par.62900.File.tmp/MediaRelease-HSAUpdatesOnFatalities&ADRAssociatedWithTheUseOfHarmfulIllegalHealthPdts-16May2008.pdf. Accessed:20 March 2008
12. Hou, P, Zou, P, Low, MY, Chan, E, and Koh, HL. 2006. Structural identification of a new acetildenafil analogue from pre-mixed bulk powder intended as a dietary supplement. Food Addit Contam, 23:870–875.
13. Jamia, AJ, Houghton, PJ, Milligan, SR, and Ibrahim, J. 2003. The oestrogenic and cytotoxic effects of the extracts of Labisia pumila var. alata and Labisia pumila var. pumila in vitro. Sains Kesihatan, 1:53–60.
14. Kardono, LBS, Angerhofer, CK, Tsauri, S, Padmawinata, K, Pezzuto, JM, and Kinghorn, D. 1991. Cytotoxic and antimalarial constituents of the roots of Eurycoma longifolia. J Nat Prod, 54:1360–1367.
15. Kim, JH, Kim, Y, Choi, K, Kim, DH, Nam, G, and Seo, JH. 2002. Preparation of novel pyrazolopyrimidinethiones as phosphodiesterase V inhibitors for treating erectile dysfunction. PCT Int. Appl.,:34 Patent number:WO02102802
16. Park, HJ, Jeong, HK, Chang, MI, Im, MH, Jeong, JY, Choi, DM, Park, K, Hong, MK, Youm, J, Han, SB. 2007. Structure determination of new analogues of vardenafil and sildenafil in dietary supplements. Food Addit Contam, 24:122–129.
17. Reepmeyer, JC, and Woodruff, JT. 2006. 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, 1125:67–75.
18. Shahrim, Z, Baharuddin, PJNM, Yahya, NA, Muhammad, H, Bakar, RA, and Ismail, Z. 2006. The in vivo rodent micronucleus assay of Kacip Fatimah (Labisia pumila) extract. Trop Biomed, 23:214–219.
19. Shin, C, Hong, M, Kim, D, and Lim, Y. 2004. Structure determination of a sildenafil analogue contained in commercial herb drinks. Magn Reson Chem, 42:1060–1062.
20. Shin, MH, Hong, MK, Kim, WS, Lee, YJ, and Jeoung, YC. 2003. Identification of a new analogue of sildenafil added illegally to a functional food marketed for penile erectile dysfunction. Food Addit Contam, 20:793–796.
21. Tada, H, Yasuda, F, Otani, K, Doteuchi, M, Ishihara, Y, and Shiro, M. 1991. New antiulcer quassinoids from Eurycoma longifolia. Eur J Med Chem, 26:345–349.
22. Venhuis, BJ, Zomer, G, and de Kaste, D. 2008. Structure elucidation of a novel synthetic thiono analogue of sildenafil detected in an alleged herbal aphrodisiac. J Pharm Biomed Anal, 46:814–7.
23. Wespes, E, Amar, E, Hatzichristou, D, Montorsi, F, Pryor, J, and Vardi, Y. 2002. Guidelines on erectile dysfunction. Eur Urol, 41:1–5.
24. Zou, P, Hou, P, Oh, SS, Chong, YM, Bloodworth, BC, Low, MY, and Koh, HL. 2008. Isolation and identification of thiohomosildenafil and thiosildenafil in health supplements. J Pharm Biomed Anal, 47:279–284.
25. Zou, P, Hou, P, Low, MY, and Koh, HL. 2006. Structural elucidation of a tadalafil analogue found as an adulterant of a herbal product. Food Addit Contam, 23:446–451.