Discovery, preparation and identification of a new type of oxyphenisatine di（acetate） analogue in dietary supplement

Authors

XIA Jintao, Hubei Provincial Institute for Food Supervision and Test, Wuhan, Hubei 430075, China;Hubei Provincial Engineering and Technology Research Center for Food Quality and Safety Test, Wuhan, Hubei 430075, China;Key Laboratory of Detection Technology of Focus Chemical Hazards in Animal-derived Food for State Market Regulation, Wuhan, Hubei 430075, ChinaFollow
WU Wanqin, Hubei Provincial Institute for Food Supervision and Test, Wuhan, Hubei 430075, China;Hubei Provincial Engineering and Technology Research Center for Food Quality and Safety Test, Wuhan, Hubei 430075, China;Key Laboratory of Detection Technology of Focus Chemical Hazards in Animal-derived Food for State Market Regulation, Wuhan, Hubei 430075, China
ZHU Songsong, Hubei Provincial Institute for Food Supervision and Test, Wuhan, Hubei 430075, China;Hubei Provincial Engineering and Technology Research Center for Food Quality and Safety Test, Wuhan, Hubei 430075, China;Key Laboratory of Detection Technology of Focus Chemical Hazards in Animal-derived Food for State Market Regulation, Wuhan, Hubei 430075, China
JIANG Feng, Hubei Provincial Institute for Food Supervision and Test, Wuhan, Hubei 430075, China;Hubei Provincial Engineering and Technology Research Center for Food Quality and Safety Test, Wuhan, Hubei 430075, China;Key Laboratory of Detection Technology of Focus Chemical Hazards in Animal-derived Food for State Market Regulation, Wuhan, Hubei 430075, China

Abstract

Objective: To find, prepare and identify a new oxyphenisatine di（acetate） analogue. Methods: A suspected derivative of oxyphenisatine di（acetate） was found by high-performance liquid chromatography-quadrupole-time-of-flight-mass spectrometry during the routine screening of weight loss healthcare product. The compound was isolated and purified by column chromatography, and the possible structures were inferred from the information of isotope mass spectra, secondary ion mass spectra, one-dimensional and two-dimensional NMR spectra. Finally, all possible structures were prepared by de novo synthesis strategy, and their fine structures were confirmed by spectral comparison. Results： The compound was identified as 5-Cl oxyphenisatine di（acetate）, a new type of oxyphenisatine di（acetate）, which has not been approved as food additives. Conclusion: The toxicological and pharmacological effects of this compound are not clear and should be of concern to regulators. The mass spectrometric fragmentation rule and the de novo synthesis of doubtful structures of these compounds will be beneficial to confirm the fine structure of new compounds.

Publication Date

3-27-2024

First Page

21

Last Page

27

DOI

10.13652/j.spjx.1003.5788.2023.80625

Recommended Citation

Jintao, XIA; Wanqin, WU; Songsong, ZHU; and Feng, JIANG (2024) "Discovery, preparation and identification of a new type of oxyphenisatine di（acetate） analogue in dietary supplement," Food and Machinery: Vol. 40: Iss. 2, Article 3.
DOI: 10.13652/j.spjx.1003.5788.2023.80625
Available at: https://www.ifoodmm.cn/journal/vol40/iss2/3

References

[1] 沈益妹, 章奇, 俞梅华, 等. 肥胖和中心性肥胖高血压控制不良患者合并血脂异常、糖尿病和高尿酸血症的分析[J]. 中国卫生检验杂志, 2023, 33（3）: 327-331. SHEN Y M, ZHANG Q, YU M H, et al. Analysis of dyslipidemia, diabetes and hyperuricemia in obesity and central obesity patients with poorly controlled hypertension[J]. Chinese Journal of Health Laboratory Technology, 2023, 33（3）: 327-331.
[2] 李建辉, 张朝晖, 王琳, 等. 减肥保健食品中非法添加物检测方法研究进展[J]. 食品安全质量检测学报, 2017, 8（5）: 1 585-1 595. LI J H, ZHANG Z H, WANG L, et al. Research progress of analysis of illegal additives in weight-reducing dietary supplements[J]. Journal of Food Safety and Quality, 2017, 8（5）: 1 585-1 595.
[3] 谭会洁, 郭常川, 邢晟, 等. Orbitrap高分辨质谱用于保健食品中15种非法添加减肥类药物的筛查鉴定[J]. 色谱, 2019, 37（9）: 969-976. TAN H J, GUO C C, XING S, et al. Application of orbitrap high resolution mass spectrometry for the screening and identification of 15 adulterated weight loss compounds in dietary supplements[J]. Chinese Journal of Chromatography, 2019, 37（9）: 969-976.
[4] 徐晓楠, 叶刚, 张楠, 等. 液相色谱—串联质谱法测定减肥降脂通便类保健食品中38种非法添加药物[J]. 食品安全质量检测学报, 2020, 11（17）: 6 075-6 085. XU X N, YE G, ZHANG N, et al. Determination of 38 kinds of illegally added drugs in health food for reducing weight, reducing blood fat and relaxing the bowels by liquid chromatography-tandem mass spectrometry[J]. Journal of Food Safety and Quality, 2020, 11（17）: 6 075-6 085.
[5] 孙晶, 柳雨影, 曹玲, 等. 电喷雾—离子迁移谱快速检测减肥类保健食品中非法添加的22种化学药物[J]. 食品工业科技, 2020, 41（14）: 228-233. SUN J, LIU Y Y, CAO L, et al. Rapid detection of 22 illegally added chemicals in weight-loss health foods by electrospray ionization-ion mobility spectrometry[J]. Science and Technology of Food Industry, 2020, 41（14）: 228-233.
[6] JAIROUN A A, AL-HEMYARI S S, SHAHWAN M, et al. Adulteration of weight loss supplements by the illegal addition of synthetic pharmaceuticals[J]. Molecules, 2021, 26（22）: 690-701.
[7] 刘静, 吴琼, 王超. 液相色谱—离子阱质谱法同时测定减肥类保健食品中非法添加的12种化学药物[J]. 食品安全质量检测学报, 2021, 12（18）: 7 286-7 292. LIU J, WU Q, WANG C. Simultaneous determination of 12 kinds of chemical drugs illegally mixed into slimming health foods by liquid chromatography-ion trap mass spectrometry[J]. Journal of Food Safety and Quality, 2021, 12（18）: 7 286-7 292.
[8] 孙健, 诸艳蓉, 胡青, 等. 超高效液相色谱—四极杆飞行时间质谱法定性筛查52种减肥类非法食品添加物[J]. 上海预防医学, 2022, 34（6）: 519-525. SUN J, ZHU Y R, HU Q, et al. Qualitative screening of 52 illegally adulterated weight-losing compounds in foods by ultra high performance liquid chromatography-quadrupole time-of-flight mass spectrometry[J]. Shanghai Journal of Preventive Medicine, 2022, 34（6）: 519-525.
[9] 韩智, 龚蕾, 王会霞, 等. 轨道离子阱快速筛查及定量分析保健食品中73种非法添加成分[J]. 食品与机械, 2019, 35（7）: 74-79. HAN Z, GONG L, WANG H X, et al. Rapid screening and quantitative analysis of 73 kinds of chemicals illegally added in the healthy foods by Orbitrap mass spectrometry[J]. Food & Machinery, 2019, 35（7）: 74-79.
[10] 胡紫艳, 金鑫, 张玲. UPLC-MS/MS 法同时测定减肥食品中55种非法添加物[J]. 中国食品卫生杂志, 2023, 35（1）: 38-48. HU Z Y, JIN X, ZHANG L. Simultaneous determination of 55 kinds of chemicals illegally added into diet foods by UPLC-MS/MS[J]. Chinese Journal of Food Hygiene, 2023, 35（1）: 38-48.
[11] 林轲亮, 莫晨宇, 杨海. 食品安全领域免罚清单制度的反思与重构[J]. 食品与机械, 2023, 39（1）: 67-72, 178. LIN K L, MO C Y, YANG H. The reflection and reconstruction of the penalty exemption list system in the field of food safety[J]. Food & Machinery, 2023, 39（1）: 67-72, 178.
[12] MANS D J, GUCINSKI A C, DUNN J D, et al. Rapid screening and structural elucidation of a novel sibutramine analogue in a weight loss supplement: 11-Desisobutyl-11-benzylsibutramine[J]. Journal of Pharmaceutical and Biomedical Analysis, 2013, 83（1）: 122-128.
[13] WANG M, HAIDER S, CHITTIBOYINA A G, et al. 1,5-Dimethylhexylamine（octodrine） in sports and weight loss supplements: Natural constituent or synthetic chemical[J]. Journal of Pharmaceutical and Biomedical Analysis, 2018, 152: 298-305.
[14] LEE J H, YANG Y J, MIN A Y, et al. Screening and elucidation of fragmentations of 23 diuretics in dietary supplements using UHPLC-Q-Orbitrap[J]. Science & Justice: Journal of the Forensic Science Society, 2021, 61（5）: 451-458.
[15] 张帆, 王美玲, 李蓉娟, 等. 保健食品中非法添加药物的广谱筛查和确证[J]. 食品与机械, 2017, 33（11）: 52-56. ZHANG F, WANG M L, LI R J, et al. Rapid screening and confirmation of weight-loss illegally added drugs in health foods[J]. Food & Machinery, 2017, 33（11）: 52-56.
[16] 朱吕, 陆春燕, 厉晨皓, 等. 超高效液相色谱—串联质谱法同时测定食品中４种减肥类非法添加药物[J]. 分析仪器, 2020（5）: 36-41. ZHU L, LU C Y, LI C H, et al. Simultaneous determination of 4 compounds illegally added in foods and losing weight health foods by HPLC-MS/MS[J]. Analytical Instrumentation, 2020（5）: 36-41.
[17] 黄芊, 叶梦薇, 冯丽凤, 等. 全自动QuEChERS-超高效液相色谱串联质谱法测定功能型休闲食品中58种非法添加药物[J]. 食品科技, 2022, 47（12）: 299-306. HUANG Q, YE M W, FENG L F, et al. Determination of 58 illegally added chemical drugs in functional leisure food by automatic QuEChERS-UPLC-MS/MS[J]. Food Science and Technology, 2022, 47（12）: 299-306.
[18] JABIR K, APARNA T, NAVEEN Y, et al. Lambert salt-initiated development of friedel-crafts reaction on isatin to access distinct derivatives of oxindoles[J]. The Journal of Organic Chemistry, 2021, 86: 17 833-17 847.