目的 鉴定保健食品中非法添加的他达拉非类似物 。方法 样品采用C18色谱柱分离,以0.1%甲酸溶液和乙腈梯度脱,利用高分辨四级杆串联飞行时间质谱(Q-TOF-MS),核磁共振(NMR)确证结构。结果 运用HPLC-DAD, Q-TOF-MS及NMR鉴定出该化合物的结构,化学名为(6S,12aR)-6-(1,3-苯并二氧戊环-5)- 2-羟乙基-2,3,6,7,12,12a-六氢吡嗪并 [1',2':1,6] 吡啶并[3,4- b ] 吲哚 -1,4-二酮。结论 利用Q-TOF-MS确证在保健食品中检出该他达拉非衍生物的结构,本实验可以为快速鉴定保健食品或非药品冒充药品中非法添加此类衍生物提供借鉴。
Abstract
OBJECTIVE To identify a new tadalafil analogue illegally adulterated in health foods. METHODS The samples were separated by C18 chromatographic column using gradiet elution with 0.1% formic acid solution and acetonitrile, and the detection was performed using quadrupole time-of-flight mass spectrometry(Q-TOF/MS) and nuclearmagnetic resonance(NMR). RESULTS The chemical structure of the new compound was elucidated by HPLC, LC-Q-TOF/MS, and NMR as(6S,12aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-(2-hydroxyethyl)-pyrazino[1'2':1,6] pyrido[3,4-b] indole-1,4-dione. CONCLUSION By using Q-TOF-MS, the structure of the tadalafil analogue illegally adulterated in health foods is disclosed for the first time. The method can be used for rapid detection of unknown novel analogues illegally added in health foods or non-pharmaceutical products.
关键词
他达拉非衍生物 /
非法添加 /
高分辨四级杆串联飞行时间质谱
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Key words
tadalafil analogue /
adulteration /
Q-TOF-MS
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中图分类号：
R917
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参考文献
[1] State Food and Drug Administration medical inspection and additional testing methods and project approval documents 200930(国家食品药品监督管理向药品检验补充检验方法和检验项目批准件2009030)[S].2009.
[2] QIU Y J, ZOU Y H. Determination of illegal added unknown sildenafil substances in health care products by UPLC-Q-TOF-MS [J]. Chin J Mod Appl Pharm(中国现代应用药学), 2015, 32(8):1000-1004.
[3] YU H, HU Q, ZHANG S, et al. Qualitative and quantitative analysis of 31 PDE-5 inhibitors in herbal products and dietary supplements by UPLC/Q-TOF-MS [J]. Chin Pharm J (中国药学杂志), 2013, 48(13):1312-1318.
[4] LEE J H, KIM N S, HAN K M, et al. Monitoring by LC-MS/MS of 48 compounds of sildenafil,tadalafil,vardenafil and their analogues in illicit healthfood products in the Korean market advertised asenhancing male sexual performance [J]. Food Addit Contam, 2013,30(10):1849-1857.
[5] XIAO S, SHI X X, NI F, et al. An efficient and general method for the stereodivergent syntheses of tadalafil-like tetracyclic compounds[J]. Eur J Org Chem, 2010,2010(9):1711-1716.
[6] LEE E S, KIM J W, LEE J H, et al. Identification of a new tadalafil analogue found in adietary supplement[J].Food Addit Contam, 2013, 30(4):621-626.
[7] HUANG Z H, CAI D D, CHEN Z Y I, et al. Discovery of nortadalafil in health foods[J]. Chin Pharm J(中国药学杂志), 2015,50(4):371-374.
[8] KLONER R A. Cardiovascular effects of the 3 phosphodiesterase-5 inhibitors approved for the treatment of erectile dysfunction [J]. Circulation, 2004, 110(19):3149-3155.
[9] VENHUIS B J, DE KASTE D. Towards a decade of detecting new analogues of sildenafil, tadalfil and vardenafil in food supplements:a history,analytical aspects and health risks[J].J Pham Biomed Anal, 2012,69(8):196-208.
[10] HUANG Z H, CAI D D, CHEN Z Y. Analysis and identification of illegally added sildenafil analogue in health food [J]. Chin J Pharm Anal (药物分析杂志), 2015,35(4):694-698.
[11] SUN J, YU H, HU Q, et al. Identification of a new sildenafil analogue based on Q-TOF-MS [J]. Acta Pharm Sin(药学学报),2014, 49(4):513-516.
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