Development of a multi-residue detection method for 27 typical pharmaceuticals and personal-care products in plants and analysis of their migration patterns in sprouts

doi:10.3724/SP.J.1123.2022.09017

Abstract

Abstract:

An analytical method based on ultra-performance liquid chromatography-tandem mass spectrometry was developed for the simultaneous determination of 27 pharmaceutical and personal-care product (PPCP) residues in plants. The enrichment and cleanup of PPCPs in plants were achieved using an HLB extraction column, and the separation was performed on a BEH C18 column (100 mm×2.1 mm, 1.7 μm) with 0.1% formic acid water-acetonitrile as the mobile phase via gradient elution. PPCPs were detected with electrospray ionization mass spectrometry in positive-ion multiple-reaction monitoring (MRM) mode. The limits of detection and quantification of the 27 PPCPs in plants were 0.01-0.30 μg/kg and 0.03-0.98 μg/kg, respectively. Good linearities were observed with coefficients of determination (r²) >0.99. The spiked recoveries were between 80.8% and 122.3% with relative standard deviations (RSDs) between 1.0% and 9.9%. The method was subsequently used to study sprouts grown in different concentrations of PPCPs. A total of 10 PPCPs were detected in sprouts grown in medium with a low concentration PPCPs, 13 PPCPs were detected in sprouts grown in medium with a moderate concentration of PPCPs, and 19 PPCPs were detected in sprouts grown in medium with a high concentration of PPCPs. These results showed that plants grown in water bodies contaminated with PPCPs or irrigated with water contaminated with PPCPs absorbed and accumulated these substances and that the amount and type of PPCPs absorbed by plants were closely related to the levels of PPCPs in the external environment. Analysis of the contents of PPCPs in different plant tissues revealed a general distribution of root>stem>leaf. Haemosibutramine showed a tissue distribution of leaf>stem>root, while glibenclamide showed a distribution of root>leaf>stem; these results revealed differences in the distribution of PPCPs in plants. Calculation of the transfer factor (TF) of the PPCPs in plants demonstrated significant differences in the transferability of different PPCPs, with TF=2.34 for haemosibutramine and TF=1.25 for chlorosibutramine. The results showed that among the drugs that migrated in plants, haemonosibutramine and chlorosibutramine had the strongest migration ability in sprouts, followed by nicardipine and chlorpheniramine maleate, and amantadine, N-monodesmethyl sibutramine, carbamazepine and flumequine had the weakest migration ability. Once absorbed, these compounds were transferred to the stems and/or leaves, where they accumulate and cause potential harm by contaminating other plant organs. Therefore, PPCPs such as homosibutramine and chlorosibutramine, which easily migrate in plants, should be given extra attention in future studies. The method is simple in pre-treatment, sensitive and accurate, and can be widely applied to the detection of PPCP residues in plant samples.

Key words: pharmaceuticals and personal care products (PPCPs), ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS), sprouts, transfer factors

CLC Number:

O658

ZENG Yongfu, CHEN Meifang, SHAO Yu, YAN Yonghuan, ZHANG Haichao, WANG Jing, AI Lianfeng, KANG Weijun. Development of a multi-residue detection method for 27 typical pharmaceuticals and personal-care products in plants and analysis of their migration patterns in sprouts[J]. Chinese Journal of Chromatography, 2023, 41(5): 386-396.

Figures/Tables 11

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Drug	CAS number	Drug type	Ionization mode	Parent ion (m/z)	Daughter ion (m/z)	Collision energy/eV	t_R/ min
Nisoldipine (尼索地平)	63675-72-9	antihypertensive drug	[M+H]⁺	389.2	239.2^*/195.2	21/42	6.17
Nimodipine (尼莫地平)	66085-59-4	antihypertensive drug	[M+H]⁺	419.2	343.2^*/301.1	14/26	3.12
Nitrendipine (尼群地平)	39562-70-4	antihypertensive drug	[M+H]⁺	361.2	315.1^*/329.2	14/15	5.85
Nicardipine hydrochloride	54527-84-3	antihypertensive drug	[M+H]⁺	480.3	315.2^*/359.2	25/25	4.51
(盐酸尼卡地平)
Minoxidil (米诺地尔)	38304-91-5	antihypertensive drug	[M+H]⁺	210.2	164.2^*/110.1	22/25	3.14
Indapamide (吲达帕胺)	26807-65-8	antihypertensive drug	[M+H]⁺	366.1	132.1^*/91.1	14/44	4.72
Lovastatin (洛伐他汀)	75330-75-5	lipid-lowering drug	[M+H]⁺	459.3	357.3^*/342.2	24/26	5.67
Mevastatin (美伐他汀)	73573-88-3	lipid-lowering drug	[M+H]⁺	391.3	185.2^*/159.1	12/28	6.48
Atorvastatin calcium (阿托伐他汀钙)	134523-03-8	lipid-lowering drug	[M+H]⁺	559.3	440.3^*/292.3	23/33	5.71
Sibutramine (西布曲明)	106650-56-0	weight-reducing aid	[M+H]⁺	280.2	125.1^*/139.1	25/15	4.75
Chlorosibutramine (氯代西布曲明)	84485-08-5	weight-reducing aid	[M+H]⁺	314.2	159.0^*/173.0	27/17	4.92
N-Monodesmethyl sibutramine	84467-94-7	weight-reducing aid	[M+H]⁺	266.2	125.1^*/139.1	24/14	4.65
(N-单去甲基西布曲明)
N,N-Bis-desmethyl sibutramine	84484-78-6	weight-reducing aid	[M+H]⁺	252.2	125.0^*/139.1	22/12	4.58
(N,N-双去甲基西布曲明)
Haemosibutramine (豪莫西布曲明)	935888-80-5	weight-reducing aid	[M+H]⁺	294.3	125.1^*/139.1	26/17	4.85
Glibenclamide (格列苯脲)	10238-21-8	hypolycemic agent	[M+H]⁺	494.2	369.1^*/169.1	15/36	5.78
Glimepiride (格列美脲)	93479-97-1	hypolycemic agent	[M+H]⁺	491.3	352.2^*/126.1	15/27	5.94
Repaglinide (瑞格列奈)	135062-02-1	hypolycemic agent	[M+H]⁺	453.3	230.2^*/162.2	28/21	4.95
Gliclazide (格列齐特)	21187-98-4	hypolycemic agent	[M+H]⁺	324.2	127.2^*/110.1	18/22	5.43
Diphenhydramine (苯海拉明)	58-73-1	antihistamine drug	[M+H]⁺	256.2	167.2^*/152.1	14/37	4.19
Chlorpheniramine maleate	113-92-8	antihistamine drug	[M+H]⁺	275.2	230.1^*/167.1	17/38	3.61
(马来酸氯苯那敏)
Flumequine (氟甲喹)	42835-25-6	antibacterial drug	[M+H]⁺	262.1	244.1^*/220.0	21/8	4.72
Sparfloxacin (司帕沙星)	110871-86-8	antibacterial drug	[M+H]⁺	393.2	292.1^*/149.0	26/55	3.45
Amantadine (金刚烷胺)	768-94-5	antiviral drug	[M+H]⁺	180.2	163.2^*/81.1	17/23	3.73
Carbamazepine (卡马西平)	298-46-4	antiepileptic drug	[M+H]⁺	237.2	194.2^*/179.2	19/34	4.56
Cortisone (可的松)	53-06-5	adrenocortical hormone	[M+H]⁺	361.2	163.1^*/121.1	23/29	4.24
Testosterone propionate (丙酸睾酮)	57-85-2	androgens	[M+H]⁺	345.2	97.1^*/109.1	24/31	7.24
Danazol (达那唑)	17230-88-5	antiestrogenic drug	[M+H]⁺	338.3	120.1^*/148.2	30/25	6.29

Drug	CAS number	Drug type	Ionization mode	Parent ion (m/z)	Daughter ion (m/z)	Collision energy/eV	t_R/ min
Nisoldipine (尼索地平)	63675-72-9	antihypertensive drug	[M+H]⁺	389.2	239.2^*/195.2	21/42	6.17
Nimodipine (尼莫地平)	66085-59-4	antihypertensive drug	[M+H]⁺	419.2	343.2^*/301.1	14/26	3.12
Nitrendipine (尼群地平)	39562-70-4	antihypertensive drug	[M+H]⁺	361.2	315.1^*/329.2	14/15	5.85
Nicardipine hydrochloride	54527-84-3	antihypertensive drug	[M+H]⁺	480.3	315.2^*/359.2	25/25	4.51
(盐酸尼卡地平)
Minoxidil (米诺地尔)	38304-91-5	antihypertensive drug	[M+H]⁺	210.2	164.2^*/110.1	22/25	3.14
Indapamide (吲达帕胺)	26807-65-8	antihypertensive drug	[M+H]⁺	366.1	132.1^*/91.1	14/44	4.72
Lovastatin (洛伐他汀)	75330-75-5	lipid-lowering drug	[M+H]⁺	459.3	357.3^*/342.2	24/26	5.67
Mevastatin (美伐他汀)	73573-88-3	lipid-lowering drug	[M+H]⁺	391.3	185.2^*/159.1	12/28	6.48
Atorvastatin calcium (阿托伐他汀钙)	134523-03-8	lipid-lowering drug	[M+H]⁺	559.3	440.3^*/292.3	23/33	5.71
Sibutramine (西布曲明)	106650-56-0	weight-reducing aid	[M+H]⁺	280.2	125.1^*/139.1	25/15	4.75
Chlorosibutramine (氯代西布曲明)	84485-08-5	weight-reducing aid	[M+H]⁺	314.2	159.0^*/173.0	27/17	4.92
N-Monodesmethyl sibutramine	84467-94-7	weight-reducing aid	[M+H]⁺	266.2	125.1^*/139.1	24/14	4.65
(N-单去甲基西布曲明)
N,N-Bis-desmethyl sibutramine	84484-78-6	weight-reducing aid	[M+H]⁺	252.2	125.0^*/139.1	22/12	4.58
(N,N-双去甲基西布曲明)
Haemosibutramine (豪莫西布曲明)	935888-80-5	weight-reducing aid	[M+H]⁺	294.3	125.1^*/139.1	26/17	4.85
Glibenclamide (格列苯脲)	10238-21-8	hypolycemic agent	[M+H]⁺	494.2	369.1^*/169.1	15/36	5.78
Glimepiride (格列美脲)	93479-97-1	hypolycemic agent	[M+H]⁺	491.3	352.2^*/126.1	15/27	5.94
Repaglinide (瑞格列奈)	135062-02-1	hypolycemic agent	[M+H]⁺	453.3	230.2^*/162.2	28/21	4.95
Gliclazide (格列齐特)	21187-98-4	hypolycemic agent	[M+H]⁺	324.2	127.2^*/110.1	18/22	5.43
Diphenhydramine (苯海拉明)	58-73-1	antihistamine drug	[M+H]⁺	256.2	167.2^*/152.1	14/37	4.19
Chlorpheniramine maleate	113-92-8	antihistamine drug	[M+H]⁺	275.2	230.1^*/167.1	17/38	3.61
(马来酸氯苯那敏)
Flumequine (氟甲喹)	42835-25-6	antibacterial drug	[M+H]⁺	262.1	244.1^*/220.0	21/8	4.72
Sparfloxacin (司帕沙星)	110871-86-8	antibacterial drug	[M+H]⁺	393.2	292.1^*/149.0	26/55	3.45
Amantadine (金刚烷胺)	768-94-5	antiviral drug	[M+H]⁺	180.2	163.2^*/81.1	17/23	3.73
Carbamazepine (卡马西平)	298-46-4	antiepileptic drug	[M+H]⁺	237.2	194.2^*/179.2	19/34	4.56
Cortisone (可的松)	53-06-5	adrenocortical hormone	[M+H]⁺	361.2	163.1^*/121.1	23/29	4.24
Testosterone propionate (丙酸睾酮)	57-85-2	androgens	[M+H]⁺	345.2	97.1^*/109.1	24/31	7.24
Danazol (达那唑)	17230-88-5	antiestrogenic drug	[M+H]⁺	338.3	120.1^*/148.2	30/25	6.29

Drug	Spiked levels/ (μg/L)	MEs/%	RSDs/%	Drug	Spiked levels/ (μg/L)	MEs/%	RSDs/%
Nisoldipine	5/50/150	116.1/109.3/96.4	6.1/7.8/5.5	N-Monodesmethyl	5/50/150	115.1/119.0/94.5	5.4/5.2/5.9
Nimodipine	5/50/150	97.3/85.7/81.2	6.9/5.3/4.8	sibutramine
Nitrendipine	5/50/150	116.1/101.2/96.1	4.6/7.7/4.4	N,N-Bis-desmethyl	5/50/150	106.2/98.1/95.7	5.3/2.8/7.2
Nicardipine	5/50/150	156.8/149.0/137.9	5.1/7.4/2.1	sibutramine
hydrochloride				Haemosibutramine	5/50/150	119.4/112.8/94.7	5.6/2.9/2.6
Minoxidil	5/50/150	91.3/85.4/87.1	4.2/2.7/3.4	Atorvastatin calcium	5/50/150	64.8/69.3/67.8	4.4/6.3/8.3
Indapamide	5/50/150	106.7/92.7/94.1	4.8/6.5/2.6	Glibenclamide	5/50/150	86.5/96.3/97.7	3.7/5.7/4.6
Lovastatin	5/50/150	119.2/118.2/114.9	6.1/5.8/3.3	Glimepiride	5/50/150	93.2/108.7/102.8	2.9/6.1/8.7
Mevastatin	5/50/150	90.2/88.9/84.7	3.8/3.7/2.5	Repaglinide	5/50/150	104.7/104.6/98.0	4.5/3.5/4.8
Amantadine	5/50/150	130.0/147.3/136.5	3.7/4.2/8.1	Gliclazide	5/50/150	103.9/97.3/94.2	4.5/3.4/2.7
Diphenhydramine	5/50/150	138.5/130.5/127.5	6.1/3.9/5.7	Cortisone	5/50/150	124.8/123.9/127.6	6.9/5.1/2.2
Chlorpheniramine	5/50/150	107.0/104.3/96.5	4.9/5.1/6.2	Danazol	5/50/150	95.1/98.4/82.1	6.6/4.3/2.8
maleate				Testosterone	5/50/150	102.3/96.6/90.8	7.4/5.4/8.8
Carbamazepine	5/50/150	95.1/97.2/82.5	2.7/6.2/3.3	propionate
Sibutramine	5/50/150	90.3/92.7/94.7	3.1/4.1/5.6	Flumequine	5/50/150	105.6/106.9/104.0	3.0/2.1/2.7
Chlorosibutramine	5/50/150	100.7/86.8/87.5	7.9/8.1/6.9	Sparfloxacin	5/50/150	68.2/66.7/63.5	8.2/7.1/4.4

Drug	Spiked levels/ (μg/L)	MEs/%	RSDs/%	Drug	Spiked levels/ (μg/L)	MEs/%	RSDs/%
Nisoldipine	5/50/150	116.1/109.3/96.4	6.1/7.8/5.5	N-Monodesmethyl	5/50/150	115.1/119.0/94.5	5.4/5.2/5.9
Nimodipine	5/50/150	97.3/85.7/81.2	6.9/5.3/4.8	sibutramine
Nitrendipine	5/50/150	116.1/101.2/96.1	4.6/7.7/4.4	N,N-Bis-desmethyl	5/50/150	106.2/98.1/95.7	5.3/2.8/7.2
Nicardipine	5/50/150	156.8/149.0/137.9	5.1/7.4/2.1	sibutramine
hydrochloride				Haemosibutramine	5/50/150	119.4/112.8/94.7	5.6/2.9/2.6
Minoxidil	5/50/150	91.3/85.4/87.1	4.2/2.7/3.4	Atorvastatin calcium	5/50/150	64.8/69.3/67.8	4.4/6.3/8.3
Indapamide	5/50/150	106.7/92.7/94.1	4.8/6.5/2.6	Glibenclamide	5/50/150	86.5/96.3/97.7	3.7/5.7/4.6
Lovastatin	5/50/150	119.2/118.2/114.9	6.1/5.8/3.3	Glimepiride	5/50/150	93.2/108.7/102.8	2.9/6.1/8.7
Mevastatin	5/50/150	90.2/88.9/84.7	3.8/3.7/2.5	Repaglinide	5/50/150	104.7/104.6/98.0	4.5/3.5/4.8
Amantadine	5/50/150	130.0/147.3/136.5	3.7/4.2/8.1	Gliclazide	5/50/150	103.9/97.3/94.2	4.5/3.4/2.7
Diphenhydramine	5/50/150	138.5/130.5/127.5	6.1/3.9/5.7	Cortisone	5/50/150	124.8/123.9/127.6	6.9/5.1/2.2
Chlorpheniramine	5/50/150	107.0/104.3/96.5	4.9/5.1/6.2	Danazol	5/50/150	95.1/98.4/82.1	6.6/4.3/2.8
maleate				Testosterone	5/50/150	102.3/96.6/90.8	7.4/5.4/8.8
Carbamazepine	5/50/150	95.1/97.2/82.5	2.7/6.2/3.3	propionate
Sibutramine	5/50/150	90.3/92.7/94.7	3.1/4.1/5.6	Flumequine	5/50/150	105.6/106.9/104.0	3.0/2.1/2.7
Chlorosibutramine	5/50/150	100.7/86.8/87.5	7.9/8.1/6.9	Sparfloxacin	5/50/150	68.2/66.7/63.5	8.2/7.1/4.4

Drug	Linear equation	Linear range/(μg/L)	r²	LOD/(μg/kg)	LOQ/(μg/kg)
Nisoldipine	y=1.1×10⁵x-1.5×10⁴	0.5-200	0.9997	0.18	0.55
Minoxidil	y=4.7×10⁵x+2.2×10⁵	0.1-150	0.9997	0.10	0.28
Nimodipine	y=3.7×10⁴x+4.8×10⁴	1.0-200	0.9999	0.24	0.72
Nicardipine hydrochloride	y=1.1×10⁵x+1.9×10⁵	0.1-200	0.9940	0.18	0.55
Indapamide	y=7.2×10⁴x-1.6×10⁴	0.5-200	0.9978	0.20	0.62
Lovastatin	y=1.4×10⁴x+3.3×10³	1.0-100	0.9970	0.28	0.84
Mevastatin	y=2.7×10⁴x-1.4×10⁴	0.5-100	0.9980	0.25	0.74
Amantadine	y=1.2×10⁵x+4.2×10⁵	0.1-200	0.9983	0.18	0.55
Diphenhydramine	y=2.1×10⁵x-1.2×10⁵	1.0-300	0.9960	0.15	0.46
Chlorpheniramine maleate	y=5.2×10⁵x+4.7×10⁵	0.1-200	0.9971	0.09	0.28
Carbamazepine	y=5.6×10⁶x+7.5×10⁵	0.1-100	0.9963	0.01	0.03
Sibutramine	y=2.9×10⁴x+1.7×10³	1.0-200	0.9980	0.25	0.74
Haemosibutramine	y=7.8×10⁵x+4.6×10⁵	0.5-150	0.9984	0.06	0.18
Chlorosibutramine	y=1.7×10⁵x-5.0×10⁵	1.0-100	0.9962	0.18	0.56
N-Monodesmethyl sibutramine	y=8.8×10³x+7.4×10³	0.5-100	0.9981	0.30	0.98
N,N-Bis-desmethyl sibutramine	y=4.2×10⁵x+1.1×10⁵	0.5-100	0.9997	0.10	0.30
Glibenclamide	y=6.8×10⁴x+3.6×10³	1.0-150	0.9963	0.20	0.62
Glimepiride	y=3.0×10⁴x+2.0×10³	1.0-150	0.9912	0.25	0.73
Gliclazide	y=2.9×10⁵x+4.5×10³	1.0-100	0.9999	0.15	0.46
Repaglinide	y=5.3×10⁵x+8.7×10³	0.1-100	0.9973	0.09	0.27
Danazol	y=6.8×10⁵x+1.4×10⁴	0.1-100	0.9964	0.08	0.25
Testosterone propionate	y=2.8×10⁴x-4.3×10³	0.5-100	0.9983	0.25	0.74
Cortisone	y=2.4×10⁵x+1.1×10⁴	0.5-100	0.9961	0.15	0.46
Flumequine	y=2.4×10⁴x-5.6×10²	1.0-100	0.9983	0.27	0.81
Sparfloxacin	y=7.9×10⁴x-4.0×10⁴	0.5-200	0.9982	0.20	0.62
Atorvastatin calcium	y=2.2×10⁵x-4.6×10⁵	1.0-200	0.9970	0.15	0.46
Nitrendipine	y=1.4×10⁴x+1.1×10⁴	1.0-200	0.9998	0.28	0.84