食品中新型那非衍生物丙氧苯基羟基伐地那非的筛查和定量测定-食品安全质量检测学报-CSCIED科技核心评价数据库-手机版

食品中新型那非衍生物丙氧苯基羟基伐地那非的筛查和定量测定

Screening and quantitative determination of novel nafil derivative propoxyphenyl hydroxyvardenafil in foods

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DOI	10.19812/j.cnki.jfsq11-5956/ts.20240927002
刊名	食品安全质量检测学报 Journal of Food Safety and Quality
年，卷(期)	2025, 16(12)
作者	王娟强, 孔维恒, 李慧晨, 董雨馨, 郭超, 赵文涛, 郭文萍*, 张颖颖, 姜锐,
作者单位	中国肉类食品综合研究中心; 肉类加工技术北京市重点实验室; 中国海关科学技术研究中心
摘要	目的对在食品中发现的一种新型伐地那非衍生物进行筛查, 并建立定量测定方法。方法采用超高效液相色谱-四极杆-静电场轨道阱高分辨质谱法在食品中发现一种与伐地那非结构类似的化合物。通过高分辨质谱碎片离子推测该伐地那非结构类似物的分子结构及裂解规律, 与定制合成的对照品比较, 确定物质名称。采用高效液相色谱-串联三重四极杆质谱法的多反应监测模式进行扫描, 外标法定量测定。结果在食品中筛查出新型那非衍生物丙氧苯基羟基伐地那非, 丙氧苯基羟基伐地那非在2~50 ng/mL质量浓度范围内线性关系良好, 检出限为0.03 mg/kg, 定量限为0.10 mg/kg, 在咖啡、压片糖果、果冻及植物饮料基质中3个加标水平下的平均回收率为87.6%~102.6%, 相对标准偏差(relative standard deviation, RSD)为0.5%~6.3%, 方法重现性和稳定性良好, RSD<5%。采用该方法对实际样品进行测定, 发现34个阳性样品, 含量范围为1.60×103~2.62×104 mg/kg。结论该方法具有快速、准确、灵敏度高等优点, 可用于食品中那非衍生物丙氧苯基羟基伐地那非的筛查和定量测定, 为打击非法添加伐地那非衍生物的监管提供技术支持。
Abstract	Objective To study and screen the novel vardenafil derivative in food, and establish a quantitative method. Methods A compound with similar structure to vardenafil was detected in food by ultra performance liquid chromatography-quadrupole-exactive orbitrap-high resolution mass spectrometry. The molecular structure and fragmentation law of the vardenafil structure analogue were inferred from the fragment ions of high-resolution mass spectrometry. The compound name was clarity compared with the custom-synthesized reference substance. Quantitative analysis was carried out in a multiple reaction monitoring by high performance liquid chromatography-tandem triple quadrupole mass spectrometry with the external standard method. Results The novel vardenafil derivative in food was identified as propoxyphenyl hydroxy-vardenafil. The results showed that good linearity was observed for propoxyphenyl hydroxyvardenafil within the concentration range of 2–50 ng/mL. The limit of detection was 0.03 mg/kg, and the limit of quantitation was 0.10 mg/kg. The average recoveries and relative standard deviations (RSD) of coffee, confectionery, jelly and plant-based drinks were 87.6%–102.6% and 0.5%–6.3% respectively. The reproducibility and stability of the method were good (RSD<5%). The method was applied to measure the real samples, and 34 batches of positive samples were found with the content range of 1.60×103–2.62×104 mg/kg. Conclusion This method is fast, accurate and high sensitivity, can be used for screening and quantitative determination of the derivative propoxyphenyl hydroxyvardenafil in food, and can provide technical support for the supervision of the illegal addition of vardenafil derivatives.
关键词	非法添加；丙氧苯基羟基伐地那非；高效液相色谱-串联三重四极杆质谱法；超高效液相色谱-四极杆-静电场轨道阱质谱法；伐地那非结构类似物
KeyWord	illegal addition; propoxyphenyl hydroxyvardenafil; high performance liquid chromatography- tandem triple quadrupole mass spectrometry; ultra performance liquid chromatography-quadrupole-exactive orbitrap-high resolution mass spectrometry; vardenafil struc
基金项目
页码	50-58

参考文献
相关文献

[1]LI CZ, WANG XZ, WU SM, et al. Separation and structural elucidation of a novel vardenafil analogue as an adulterant in a natural health care dietary supplement
[J]. Heliyon, 2023(9): e15418.
[2]王进欣, 储刚, 孙飘扬, 等. 伐地那非衍生物的合成和体内活性评价
[J]. 化学学报, 2007, 65(24): 2917–2922. WANG JX, CHU G, SUN PY, et al. Synthesis of vardenafil analogue and its activity evaluation in vivo
[J]. Acta Chimica Sinica, 2007, 65(24): 2917–2922.
[3]姜辉. 伐地那非的分子学研究
[J]. 中华男科学杂志, 2005, 11(5): 396–399. JIANG H. Molecular studies of vardenafil
[J]. National Journal of Andrology, 2005, 11(5): 396–399.
[4]KEE CL, GE XW, VéRONIQUE G, et al. A review of synthetic phosphodiesterase type 5 inhibitors (PDE-5i) found as adulterants in dietary supplements
[J]. Journal of Pharmaceutical and Biomedical Analysis, 2018, 147: 250–277.
[5]ELINA PG, STANISLAV G, HRISTINA L, et al. Survey on sildenafil, tadalafil, and vardenafil concentrations in food supplements for erectile dysfunction
[J]. International Journal of Analytical Chemistry, 2022, 3950190: 1–6.
[6]SHIN D, KWON J, KANG HS, et al. The presence of unauthorized ingredients in dietary supplements: An analysis of the risk warning data in Korea
[J]. Journal of Food Composition and Analysis, 2022, 108: 104462.
[7]ZURAWIN JL, STEWART CA, ANAISSIE JE, et al. Avanafil for the treatment of erectile dysfunction
[J]. Expert Review of Clinical Pharmacology, 2016, 9: 1163–1170.
[8]LIU JL, SUN J, WEI H, et al. Isolation and characterization of a novel tadalafil analogue adulterant, N-cyclohexyl nortadalafil, in a dietary supplement
[J]. Journal of Pharmaceutical and Biomedical Analysis, 2023, 227: 115144.
[9]夏金涛, 吴婉琴, 朱松松, 等. 固体饮料中一种新型卡巴地那非类似物的定性鉴别和定量分析
[J]. 分析测试学报, 2022, 41(5): 754–760. XIA JT, WU WQ, ZHU SS, et al. Qualitative and quantitative identification of a new carbadenafil analogue in solid beverages
[J]. Journal of Instrumental Analysis, 2022, 41(5): 754–760.
[10]李涛, 袁磊, 王建山, 等. 超高效液相色谱-三重四极杆/复合线性离子阱质谱法快速筛查和鉴定保健食品中非法添加的新型西地那非类衍生物
[J]. 食品安全质量检测学报, 2017, 8(10): 3991–3996. LI T, YUAN L, WANG JS, et al. Screening and identification of sildenafil analogues illegally added in healthy foods by ultra performance liquid chromatography-triple quadrupole linear/ion trap of mass spectrometry
[J]. Journal of Food Safety & Quality, 2017, 8(10): 3991–3996.
[11]宁霄, 金绍明, 李志远, 等. 功能性老年乳粉中300种非法添加药物及其类似物的液相色谱-高分辨质谱分析
[J]. 色谱, 2023, 41(11): 960–975. NING X, JIN SM, LI ZY, et al. Liquid chromatography?high resolution mass spectrometry analysis of 300 illegally added drugs and their analogues in functional milk powder for the elderly
[J]. Chinese Journal of Chromatography, 2023, 41(11): 960–975.
[12]DAYOUNG H, JAE SK, SANGGIL C, et al. Metabolic study of vardenafil analogues: Pseudovardenafil and hydroxyvardenafil
[J]. Journal of Chromatography, B, 2020, 1139: 121940.
[13]KASHGARI FK, RAVNA A, SAGER G, et al. Identification and experimental confirmation of novel cGMP efflux inhibitors by virtual ligand screening of vardenafil-analogues
[J]. ?Biomedicine and Pharmacotherapy, 2020, 126: 110109.
[14]VENHUIS BJ, KASTE DD. Towards a decade of detecting new analogues of sildenafil, tadalafil and vardenafil in food supplements: A history, analytical aspects and health risks
[J]. Journal of Pharmaceutical and Biomedical Analysis, 2012, 69: 196–208.
[15]TRAVIS MF, BIRGIT S, CARSTEN B, et al. Combining trapped ion mobility spectrometry with liquid chromatography and tandem mass spectrometry for analysis of isomeric PDE-5 inhibitor analogs
[J]. Journal of Pharmaceutical and Biomedical Analysis, 2023, 225: 115210.
[16]李少元, 接强, 栾玉静, 等. 保健食品中西地那非等PDE-5i检测方法研究进展
[J]. 刑事技术, 2023, 48(3): 221–227. LI SY, JIE Q, LUAN YJ, et al. Research progress of detection methods about PDE-5i including sildenafil in healthcare food
[J]. Forensic Science and Technology, 2023, 48(3): 221–227.
[17]KLAUDIA S, BULCSú D, ANNA é, et al. Possible retinotoxicity of long-term vardenafil treatment
[J]. Experimental Eye Research?, 2024, 243: 109890.
[18]TAKAAKI N, GENYA W, RYUHEI H, et al. Acute intracranial and spinal subdural hematoma associated with vardenafil
[J]. Journal of Stroke and Cerebrovascular Diseases, 2018, 27(9): e201–e202.
[19]国家市场监督管理总局. 市场监管总局办公厅关于打击食品中非法添加那非拉非类物质及其系列衍生物违法行为的意见(市监稽发〔2022〕74号)
[EB/OL]. (2022-08-11)
[2024-09-27]. https://www.samr.gov.cn/cms_files/ filemanager/1647978232/attach/20238/c6ca62afbd8d4942be5b0591a4830fba.pdf State Administration for Market Regulation. Opinions of the general office of the state administration for market regulation on cracking down on illegal addition of nafilafine-like substances and their series of derivatives in food (No. 74 of 2022 issued by the general office of the state administration for market regulation)
[EB/OL]. (2022-08-11)
[2024-09-27]. https://www.samr.gov.cn/cms_files/filemanager/1647978232/attach/20238/ c6ca62afbd8d4942be5b0591a4830fba.pdf
[20]国家市场监督管理总局. 市场监管总局办公厅关于打击食品中非法添加酚汀(酚丁)、酚酞及其酯类衍生物或类似物违法行为的通知(市监稽发〔2023〕95号)
[EB/OL]. (2023-10-13)
[2024-09-27]. https://www. samr.gov.cn/zw/zfxxgk/fdzdgknr/zfjcs/art/2023/art_5b69a28fde634bfab1dc178a63fce009.html State Administration for Market Regulation. Notice of the general office of the state administration for market regulation on cracking down on illegal addition of phenolphthalins (phenolphthalins), phenolphthalein and their ester derivatives or analogues in food (No. 95 of 2023 issued by the general office of the state administration for market regulation)
[EB/OL]. (2023-10-13)
[2024-09-27]. https://www. samr.gov.cn/zw/zfxxgk/fdzdgknr/ zfjcs/art/2023/art_5b69a28fde634bfab1dc178a63fce009.html
[21]田明, 王玉伟, 冯军, 等. 保健食品及相关食品典型案例分析
[J]. 中国食品学报, 2024, 24(1): 487?496. TIAN M, WANG YW, FENG J, et al. Typical case analysis of health food and related food
[J]. Journal of Chinese Institute of Food Science and Technology, 2024, 24(1): 487?496.
[22]陈美芳, 陈秀萍. 电商模式下保健食品市场监管问题及对策分析
[J]. 卫生软科学, 2024, 38(6): 33–37. CHEN MF, CHEN XP. Analysis of problems and countermeasures of market supervision in health food market under e-commerce model
[J]. Soft Science of Health, 2024, 38(6): 33–37.
[23]孙健, 于泓, 胡青, 等. 一种新型西地那非衍生物的Q-TOF-MS鉴定
[J]. 药学学报, 2014, 49(4): 513–516. SUN J, YU H, HU Q, et al. Identification of a new sildenafil analogue based on Q-TOF-MS
[J]. Acta Pharmaceutica Sinica, 2014, 49(4): 513–516.
[24]XIA JT, WU WQ, JIANG F, et al. A novel vardenafil analog in a healthcare product: Preparation, characterization, and quantification
[J]. Heliyon, 2023, (9): e19456.
[25]冯亭亭, 孙健, 张静娴, 等. 一种他达拉非衍生物的的发现与鉴定
[J]. 药学学报, 2020, 55(8): 1877–1881. FENG TT, SUN J, ZHANG JX, et al. Discovery and identification of a tadalafil analogue
[J]. Acta Pharmaceutica Sinica, 2020, 55(8): 1877–1881.
[26]张建丽, 王小兵. LC/MS和LC-MS/MS定性检测保健品中非法添加的伐地那非
[J]. 质谱学报, 2009, 30(4): 219–222. ZHANG JL, WANG XB. Detection of vardenafil in health products by LC/MS and LC-MS/MS
[J]. Journal of Chinese Mass Spectrometry Society, 2009, 30(4): 219–222.
[27]夏金涛, 吴婉琴, 江丰, 等. 压片糖果中一种新型伐地那非衍生物的发现和确证
[J]. 分析试验室, 2024, 43(7): 1004–1010. XIA JT, WU WQ, JIANG F, et al. Discovery and confirmation of a new type of vardenafil derivatives in pressed candy
[J]. Chinese Journal of Analysis Laboratory, 2024, 43(7): 1004–1010.
[28]朱泽兵, 郭娅, 张德伟, 等. 补肾壮阳类中成药中15种非法添加化学药物的检测方法研究
[J]. 质量安全与检验检测, 2024, 34(1): 42–49. ZHU ZB, GUO Y, ZHANG DW, et al. Study on the detection methods of 15 kinds of chemical drugs illegally added to kidney—tonifying and aphrodisiacal Chinese patent medicine
[J]. Quality Safety Inspection and Testing, 2024, 34(1): 42–49.
[29]SUN J, YU H, ZHANG JX, et al. Isolation and identification of a novel vardenafil analogue, propoxy-vardenafil, found as an adulterant in a health supplement
[J]. Heliyon, 2023(9): e17253.
[30]刘雅婷, 郭予昕, 刘振强, 等. 食品中一种新型伐地那非结构类似物的筛查与定量测定
[J]. 分析测试学报, 2023, 42(11): 1488–1494. LIU YT, GUO YX, LIU ZQ, et al. Screening and quantitative determination of a new vardenafil analogue in foods
[J]. Journal of Instrumental Analysis, 2023, 42(11): 1488–1494.
[31]饶雅琨, 王苑桃, 孙晓, 等. 食品中一种新型非法添加物O-丙基伐地那非的快速筛查和定量测定
[J]. 食品安全质量检测学报, 2024, 15(6): 228–235. RAO YK, WANG YT, SUN X, et al. Rapid screening and quantitative determination of a new illegally added compound O-propyl vardenafil in foods
[J]. Journal of Food Safety & Quality, 2024, 15(6): 228–235.
[32]郭超, 陈超, 李慧晨, 等. 基于高效液相色谱-质谱联用技术检测畜肉中的瓜尔胶
[J]. 食品科学, 2022, 43(24): 349–356. GUO C, CHEN C, LI HC, et al. Detection of guar gum in adulterated livestock meat by high performance liquid chromatography-mass spectrometry
[J]. Food Science, 2022, 43(24): 349–356.
[33]廖伟杰, 黄兆翔, 高佳敏. 优化液质法测定多种基质中五氯酚残留量
[J]. 广州化学, 2024, 49(3): 66–69. LIAO WJ, HUANG ZX, GAO JM, et al. Lc-ms for the determination of pentachlorophenol residues in a variety of matrices
[J]. Guangzhou Chemistry, 2024, 49(3): 66–69.
[34]王娟强, 刘梦瑶, 张明悦, 等. 超高效液相色谱-串联质谱法检测畜肉及内脏中苯甲酸和马尿酸残留
[J]. 食品科学, 2022, 43(14): 311–318. WANG JQ, LIU MY, ZHANG MY, et al. Determination of benzoic acid and hippuric acid residues in meat and offal by ultra performance liquid chromatography-tandem mass spectrometry
[J]. Food Science, 2022, 43(14): 311–318.
[35]WANG JQ, LIU XR, WEI Y. Magnetic solid-phase extraction based on magnetic zeolitic imazolate framework-8 coupled with high performance liquid chromatography for the determination of polymer additives in drinks and foods packed with plastic
[J]. Food Chemistry, 2018, 256: 358–366.

引用本文

王娟强, 孔维恒, 李慧晨, 董雨馨, 郭超, 赵文涛, 郭文萍*, 张颖颖, 姜锐. 食品中新型那非衍生物丙氧苯基羟基伐地那非的筛查和定量测定 [J]. 食品安全质量检测学报. 2025; 16; (12). 50 - 58.

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