No. LCMSMS-065E

This application news presents a method for the determination of 17 hormone residues in milk using Shimadzu Ultra-High-Performance Liquid Chromatograph (UHPLC) LC-30A and Triple Quadrupole Mass Spectrometer LCMS-8040. After sample pretreatment, the compounds in the milk matrix were separated using UPLC LC-30A and analyzed via Triple Quadrupole Mass Spectrometer LCMS-8040. All 17 hormones displayed good linearity within their respective concentration range, with correlation coefficient in the range of 0.9974 and 0.9999. The RSD% of retention time and peak area of 17 hormones at the low-, mid- and high- concentrations were in the range of 0.0102-0.161% and 0.563-6.55% respectively, indicating good instrument precision. Method validation was conducted and the matrix spike recovery of milk ranged between 61.00-110.9%. The limit of quantitation was 0.14-0.975 g/kg, and it meets the requirement for detection of hormones in milk. Keywords: Hormones; Milk; Solid phase extraction; Ultra performance liquid chromatograph; Triple quadrupole mass spectrometry ■ Introduction Since 2008’s melamine-tainted milk scandal, the adulteration of milk powder has become a major food safety concern. In recent years, another case of dairy product safety is suspected to cause "infant sexual precocity" (also known as precocious puberty) and has become another major issue challenging the dairy industry in China. These frequent food safety crises on milk powder quality severely decrease consumer confidence in domestic milk quality as well as impede the development of milk manufacturing industry. Considering the interest and motivation of manufacturers, it is apparent that hormones are not added during milk powder manufacturing and processing. However, farmers may use antibiotics and hormones illegally on cows to increase the milk yield for milk production. With the exception of endogenous progestogens, estrogens and androgens, all other chemically synthesized hormones in milk belong to prohibited drugs. In 2002, the Ministry of Agriculture of China issued an announcement (no. 235) prohibiting the use of chemically synthesized hormones such as diethylstilbestrol, medroxyprogesterone acetate, methyltestosterone, trenbolone and zeranol and stipulated that these compounds shall not be detected in any animal-derived food. At the same time, both EU directive 96/22/EC and US FDA have also banned the use of hormone drugs in animal-derived food.

With reference to China’s national standard GB/T 21981-2008 "Hormone Multi-Residue Detection Method for Animal-derived Food - LC-MS Method", a method utilizing solid phase extraction, ultra-performance liquid chromatography and triple quadrupole mass spectrometry was developed for the rapid and high-sensitive detection of 17 hormones in milk. ■ Experimental 1.1. Instruments Shimadzu Ultra-High-Performance Liquid Chromatograph (UHPLC) Nexera X2 and Triple Quadrupole Mass Spectrometer LCMS-8040 system was used. The specific configuration included LC-30AD×2 infusion pumps, DGU-20A5 Online Degasser, SIL-30AC Autosampler, CTO-30AC Column Oven, CBM-20A System Controller, Triple Quadrupole Mass Spectrometer LCMS-8040, and LabSolutions Ver. 5.53 Chromatography Workstation.

Liquid Chromatography Mass Spectrometry Determination of 17 Hormone Residues in Milk by Ultra-High-Performance Liquid Chromatography and Triple Quadrupole Mass Spectrometry

No. LCMSMS-65E

No. LCMSMS-065E

1.2. Analytical Conditions Liquid chromatography (LC) parameters

• Analyzer: Nexera X2 System • Chromatographic column: Shimadzu Shim-pack XR-

ODS II 2.0 mm ID x 75 mmL, 2.2µm • Mobile phase: A-0.1% formic acid solution, B-

methanol, A/B=50%/50% (V/V) • Flow rate: 0.4 mL/min • Elution mode: gradient elution, refer to Table 1 • Injection volume: 5 μL • Column temperature: 40°C

Mass spectrometry (MS) conditions

• Analyzer: LCMS-8040 • Ion source: ESI, positive ion scan • Ion source interface voltage: 4.5 kV • Nebulizing gas: Nitrogen 3.0 L/min • Drying gas: Nitrogen 15 L/min • Collision gas: Argon • DL temperature: 250°C • Heating module temperature: 400°C • Scan mode: Multiple Reaction Monitoring (MRM) • Dwell time: 30 msec • Pause time: 3 msec • MRM parameters: Refer to Table 2

Table 1: Gradient Program Time(min) Module Command Value

8 Pumps PumpB Cone. 64

11 Pumps PumpB Cone. 64 12.5 Pumps PumpB Cone. 100

14.5 Pumps PumpB Cone. 100

15 Pumps PumpB Cone. 50

20 Controller Stop

Table 2: MRM Parameters

Compound name Precursor ion Product ion Q1 Pre Bias

(V) CE (V)

Q3 Pre Bias (V)

Androstenedione 287.05 287.05

97.00* 109.15

-15.0 -15.0

-25.0 -25.0

-20.0 -23.0

Boldenone 287.10 287.10

121.05* 135.05

-26.0 -26.0

-25.0 -15.0

-26.0 -15.0

Danazol 338.25 338.25

148.15* 120.00

-26.0 -26.0

-30.0 -35.0

-16.0 -24.0

Fluoxymesterone 337.15 337.15

241.15* 131.00

-13.0 -13.0

-25.0 -35.0

-18.0 -28.0

Testosterone 289.25 289.25

97.00* 109.05

-25.0 -25.0

-25.0 -25.0

-20.0 -22.0

Methyltestosterone 303.25 303.25

109.15* 97.15

-25.0 -25.0

-30.0 -25.0

-21.0 -19.0

Methandienone 301.25 301.25

121.15* 149.15

-26.0 -26.0

-25.0 -15.0

-13.0 -16.0

Nandrolone 275.10 275.10

109.10* 257.20

-13.0 -13.0

-30.0 -15.0

-22.0 -20.0

Norandrostenedione 273.10 273.10

109.15* 197.10

-10.0 -10.0

-25.0 -20.0

-23.0 -15.0

Trenbolone 271.20 271.20

253.15* 199.05

-27.0 -23.0

-20.0 -25.0

-19.0 -15.0

Megestrol acetate 385.10 385.10

267.15* 325.20

-23.0 -23.0

-20.0 -15.0

-20.0 -25.0

Medroxyprogesterone 345.30 345.30

123.00* 97.20

-13.0 -13.0

-25.0 -25.0

-13.0 -19.0

Medroxyprogesterone acetate 387.30 387.30

123.00* 327.25

-15.0 -15.0

-30.0 -10.0

-13.0 -25.0

Norgestrel 313.25 313.25

109.15* 245.20

-12.0 -12.0

-35.0 -25.0

-24.0 -18.0

Chlormadinone acetate 405.05 405.05

345.20* 309.15

-24.0 -24.0

-15.0 -20.0

-18.0 -23.0

Norethindrone 299.05 299.05

109.05* 91.15

-19.0 -19.0

-35.0 -25.0

-22.0 -11.0

Progesterone 315.15 315.15

97.15* 109.00

-12.0 -12.0

-25.0 -30.0

-20.0 -21.0

* Quantifier ion

No. LCMSMS-065E

1.3. Sample Preparation 1.3.1. Preparation of standard solutions A mixed standard solution of 17 hormones, each containing 1000 µg/L, was prepared by diluting the individual hormone standard (100 mg/L) with ultrapure water. The mixed standard solution was

subsequently diluted with water to prepare standard working solutions at different concentration points as shown in Table 3. The standard calibration curves were established using these concentrations.

Table 3: Concentrations (μg/L) of 17 Hormones used for Calibration Compound name Conc. 1 Conc.2 Conc.3 Conc.4 Conc.5 Conc.6 Conc. 7 Norandrostenedione 1 2 4 10 20 50 100 Trenbolone 1 2 4 10 20 50 100 Boldenone 1 2 4 10 20 50 100 Nandrolone 1 2 4 10 20 50 100 Androstenedione 1 2 4 10 20 50 100 Methandienone 1 2 4 10 20 50 100 Testosterone 1 2 4 10 20 50 100 Methyltestosterone 1 2 4 10 20 50 100 Medroxyprogesterone 1 2 4 10 20 50 100 Megestrol acetate 1 2 4 10 20 50 100 Medroxyprogesterone acetate 1 2 4 10 20 50 100 Progesterone 1 2 4 10 20 50 100 Norethindrone 5 10 20 50 100 250 500 Norgestrel 5 10 20 50 100 250 500 Chlormadinone acetate 5 10 20 50 100 250 500 Fluoxymesterone 10 20 40 100 200 500 1000 Danazol 10 20 40 100 200 500 1000 1.3.2. Pretreatment of sample Milk samples were pretreated with reference to GB/T 21981-2008 "Hormone Multi-Residue Detection Method for Animal-derived Food - LC-MS Method". ■Results and discussion 2.1. Q1 Scan and Product Ion Scan Mass Spectra of the Hormone Standards

1. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -22V) (right) of androstenedione.

No. LCMSMS-065E

2. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -21V) (right) of boldenone.

3. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -40V) (right) of danazol.

4. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -32V) (right) of fluoxymesterone.

No. LCMSMS-065E

5. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -25V) (right) of testosterone.

6. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -26V) (right) of methyltestosterone.

7. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -18V) (right) of methandienone.

No. LCMSMS-065E

8. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -24V) (right) of nandrolone.

9. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -25V) (right) of norandrostenedione.

10. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -30V) (right) of trenbolone.

No. LCMSMS-065E

11. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -19V) (right) of megestrol acetate.

12. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -29V) (right) of medroxyprogesterone.

13. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -20V) (right) of medroxyprogesterone acetate.

No. LCMSMS-065E

14. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -26V) (right) of norgestrel.

15. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -18V) (right) of chlormadinone acetate.

16. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -32V) (right) of norethindrone.

No. LCMSMS-065E

17. The Q1 scan mass spectrum (left) and Product Ion Scan mass spectrum (CE value was -25V) (right) of progesterone.

Figure 1: Q1 Scan and Product Ion Scan Mass Spectra of the Hormone Standards 2.2. MRM Chromatogram of the Mixed Hormones Standard Refer to Figure 2 for the MRM chromatogram of the mixed hormones standard.

Figure 2: MRM Chromatograms of the Hormone Standards

Peak attribution: 1. Norandrostenedione (10 μg/L); 2. Trenbolone (10 μg/L); 3. Boldenone (10 μg/L); 4. Fluoxymesterone (100 μg/L); 5. Nandrolone (10 μg/L); 6. Androstenedione (10 μg/L); 7. Norethindrone (50 μg/L); 8. Methandienone (10 μg/L); 9. Testosterone (10 μg/L); 10. Norgestrel (50 μg/L); 11. Methyltestosterone (10 μg/L); 12. Medroxyprogesterone (10 μg/L); 13. Megestrol acetate (10 μg/L); 14. Chlormadinone acetate (50 μg/L); 15. Medroxyprogesterone acetate (10 μg/L); 16. Progesterone (10 μg/L); 17. Danazol (100 μg/L). 2.3. Calibration and Linearity Calibration was performed using a seven-point curve and external standard method. Figure 3 shows the calibration curves of all 17 hormones. Excellent linearity was obtained over the respective

concentration range (Table 3) with the correlation coefficient ranging between 0.9974 and 0.9999 (Table 4).

No. LCMSMS-065E

1. Norandrostenedione

2. Trenbolone

3. Boldenone

4. Fluoxymesterone

5. Nandrolone

6. Androstenedione

7. Norethindrone

8. Methandienone

9. Testosterone

10. Norgestrel

11. Methyltestosterone 12. Medroxyprogesterone

No. LCMSMS-065E

Figure 3: Calibration curves of all 17 hormones Table 4: Calibration Curve Results of 17 Hormones

No. Compound Name Calibration curve equation Linear range (μg/L) Correlation coefficient (R)

1 Norandrostenedione Y = (6291.94)X + (5045.17) 1.0-100 0.9998 2 Trenbolone Y = (8093.28)X + (11702.5) 1.0- 100 0.9999 3 Boldenone Y = (33290.1)X + (39696.4) 1.0- 100 0.9997 4 Fluoxymesterone Y = (1304.96)X + (21697.4) 10-1000 0.9991 5 Nandrolone Y = (10371.7)X + (11750.5) 1.0- 100 0.9997 6 Androstenedione Y= (9140.16)X + (4939.96) 1.0- 100 0.9999 7 Norethindrone Y = (3771.80)X + (44103.2) 5.0- 500 0.9993 8 Methandienone Y = (28151.5)X + (39506.0) 1.0- 100 0.9999 9 Testosterone Y = (17610.0)X + (13733.6) 1.0- 100 0.9999 10 Norgestrel Y = (3882.87)X + (56327.6) 5.0- 500 0.9992 11 Methyltestosterone Y = (14053.9)X + (28168.1) 1.0-100 0.9996 12 Medroxyprogesterone Y = (13545.6)X + (-8027.14) 1.0- 100 0.9985 13 Megestrol acetate Y = (17153.8)X+ (-18765.8) 1.0-100 0.9984 14 Chlormadinone acetate Y = (2524.61)X + (10654.8) 5.0- 500 0.9998 15 Medroxyprogesterone

acetate Y = (8715.12)X + (-11254 .1) 1.0- 100 0.9974

16 Progesterone Y= (22587.5)X + (-25767.7) 1.0- 100 0.9991 17 Danazol Y = (2422.08)X + (85881.9) 10- 1000 0.9977

2.4. Precision Experiment Mixed hormone standard solutions at low-, mid- and high- concentrations were prepared and analyzed (n=6). The RSD% obtained showed good instrument precision (Table 5).

13. Megestrol acetate

14. Chlormadinone acetate 15. Medroxyprogesterone acetate

16. Progesterone

17. Danazol

No. LCMSMS-065E

Table 5: Repeatability Results of Retention Time and Peak Area (n=6) Sample name RSD%

(low-conc, μg/L) RSD% (mid-conc, μg/L)

RSD% (high-conc, μg/L)

Norandrostenedione 0.1 1 5.82 0.115 2.32 0.0458 0.887 Trenbolone 0.125 4 83 0.0787 3.17 0.0400 1.12 Boldenone 0.0958 4.48 0.0767 2.60 0.0384 1.57 Fluoxymesterone 0.106 4.14 0.0700 2.40 0.0392 1.85 Nandrolone 0.131 6.55 0.0977 2.45 0.0444 0.715 Androstenedione 0.149 5.24 0.0333 1.71 0.0325 1.51 Norethindrone 0.123 0.909 0.0737 1.24 0.0364 0.745 Methandienone 0.0942 2.83 0.0635 1.88 0.0405 0.713 Testosterone 0.141 1.58 0.0578 3.53 0.0532 0.563 Norgestrel 0 .112 1.86 0.0414 2.14 0.0461 0.659 Methyltestosterone 0.160 2.27 0.0269 2.46 0.0472 1.54 Medroxyprogesterone 0.116 0.946 0.0147 3.65 0.0264 2.68 Megestrol acetate 0.120 5.25 0.0172 5.61 0.0271 2.78 Chlormadinone acetate 0 .0622 4.03 0.0196 5.27 0.0116 1.56 Medroxyprogesterone acetate

0 .0862 6.54 0.0102 4.08 0.0169 2.51

Progesterone 1.0658 4.99 0.0177 4.05 0.0138 2.04 Danazol 0.0566 5.09 0.0124 5.36 0.0168 2.74

1. Low concentration: The concentration of fluoxymesterone and danazol was 20 μg/L and the concentration of norethindrone,

norgestrel and chlormadinone acetate was 10 μg/L, while the concentration of all the remaining hormones was 2 μg/L; 2. Mid-concentration: The concentration of fluoxymesterone and danazol was 100 μg/L and the concentration of norethindrone,

norgestrel and chlormadinone acetate was 50 μg/L, while the concentration of all remaining hormones was 10 μg/L; 3. High concentration: The concentration of fluoxymesterone and danazol was 500 μg/L and the concentration of norethindrone,

norgestrel and chlormadinone acetate was 250 μg/L, while the concentration of all remaining hormones was 50 μg/L. 2.5. Limit of Detection and Limit of Quantitation In order to examine the sensitivity of the instrument, 7 standard hormone samples were prepared at various concentrations (Table 6). Seven parallel sample injections were conducted, and the resulting chromatograms are shown in Figure 4. The limit of detection and limit of quantitation were calculated

based on the standard deviations (S) determined from 7 injections. Method Detection Limit (MDL) is calculated to be 3.14 x S, while the limit of quantitation (LOQ) is defined as 4 times of MDL. The results are determined and shown in Table 6.

Table 6: Method Detection Limit and Limit of Quantitation of 17 Hormones

No. Compound Name Concentration (μg/L)

Standard deviation (S)

Detection limit (μg/L)

Limit of quantitation

(μg/L) 1 Norandrostenedione 1 0.076 0.24 0.96 2 Trenbolone 1 0.062 0.19 0.76 3 Boldenone 1 0.060 0.19 0.76 4 Fluoxymesterone 10 0.069 0.22 0.87 5 Nandrolone 1 0.054 0.17 0.68 6 Androstenedione 1 0.089 0.28 1.12 7 Norethindrone 5 0.082 0.26 1.04 8 Methandienone 1 0.020 0.06 0.24 9 Testosterone 1 0.043 0.14 0.54 10 Norgestrel 5 0.11 0.34 1.36 11 Methyltestosterone 1 0.035 0.11 0.44 12 Medroxyprogesterone 1 0.060 0.19 0.76 13 Megestrol acetate 1 0.10 0.31 1.24 14 Chlormadinone acetate 5 0.071 0.22 0.88 15 Medroxyprogesterone acetate 1 0.079 0.25 1.00 16 Progesterone 1 0.059 0.19 0.76 17 Danazol 10 0.16 0.50 2.00

No. LCMSMS-065E

Figure 4: MRM Chromatograms of Hormone Standard Samples (Refer to Table 6 for the concentrations) Peak attribution: 1. Norandrostenedione; 2. Trenbolone; 3. Boldenone; 4. Fluoxymesterone; 5. Nandrolone; 6. Androstenedione; 7.

Norethindrone; 8. Methandienone; 9. Testosterone; 10. Norgestrel; 11. Methyltestosterone; 12. Medroxyprogesterone; 13. Megestrol acetate; 14. Chlormadinone acetate; 15. Medroxyprogesterone acetate; 16. Progesterone; 17. Danazol.

2.6. Matrix Spike and Recovery Experiment Figure 5 shows the MRM chromatogram of the milk sample prepared according to the method stated in 1.3. Based on the experimental results, progesterone was detected. 17 hormone standards were spiked to the milk sample matrix, and the MRM chromatogram after spiking are shown in Figure 6.

The results of detection and matrix spike recovery of these 17 hormones in milk are shown in Table 7. The limit of quantitation of this method was calculated to be 0.14~0.97 μg/kg, where LOQ = 10 x S/N (Table 8).

Figure 5: MRM Chromatogram of the Milk Matrix

No. LCMSMS-065E

Figure 6: MRM Chromatogram of Spiked Milk Matrix (Refer to Table 7 for the concentrations and Figure 4 for peak attribution)

Table 7: Detection and Spiked Recovery Results of Hormones in Milk

No. Compound Name Concentration of hormones in non-spiked milk samples (μg/kg)

Spiking concentration (μg/kg)

Concentration of hormones in spiked milk samples (μg/kg)

Recovery (%)

1 Norandrostenedione N.D. 3.2 2.77 86.6 2 Trenbolone N.D. 3.2 2.39 74.7 3 Boldenone N.D. 3.2 2.59 80.9 4 Fluoxymesterone N.D. 32 27.1 84.7 5 Nandrolone N.D. 3.2 3.10 96.9 6 Androstenedione N.D. 3.2 3.00 93.8 7 Norethindrone N.D. 16 10.5 65.6 8 Methandienone N.D. 3.2 2.06 64.4 9 Testosterone N.D. 3.2 2.87 89.7 10 Norgestrel N.D. 16 10.9 68.1 11 Methyltestosterone N.D. 3.2 2.25 70.3 12 Medroxyprogesterone N.D. 3.2 3.55 110.9 13 Megestrol acetate N.D. 3.2 3.50 109.4 14 Chlormadinone acetate N.D. 16 14.5 90.6 15 Medroxyprogesterone acetate N.D. 3.2 3.30 103.1 16 Progesterone 1.5 3.2 4.74 101.2 17 Danazol N.D. 32 19.5 61.0

Note: N.D. represents not detected.

No. LCMSMS-065E

Table 8: Method Detection Limit and Limit of Quantitation

No. Compound Name Spiking concentration (μg/kg)

Signal to noise ratio (S/N)

Method detection limit (μg/kg)

Limit of quantitation (μg/kg)

1 Norandrostenedione 1.6 48 0.10 0.33 2 Trenbolone 1.6 54 0.09 0.30 3 Boldenone 1.6 41 0.12 0.40 4 Fluoxymesterone 16 168 0.29 0.97 5 Nandrolone 1.6 55 0.09 0.30 6 Androstenedione 1.6 60 0.08 0.27 7 Norethindrone 8 140 0.17 0.57 8 Methandienone 1.6 89 0.05 0.17 9 Testosterone 1.6 116 0.04 0.14 10 Norgestrel 8 139 0.17 0.57 11 Methyltestosterone 1.6 96 0.05 0.17 12 Medroxyprogesterone 1.6 40 0.12 0.40 13 Megestrol acetate 1.6 54 0.09 0.30 14 Chlormadinone acetate 8 202 0.12 0.40 15 Medroxyprogesterone acetate 1.6 56 0.09 0.30 16 Progesterone 1.6 47 0.10 0.34 17 Danazol 16 171 0.28 0.93

■ Conclusion A method for the rapid determination of 17 hormone residues in milk was developed using Shimadzu Nexera X2 UHPLC and Triple Quadrupole Mass Spectrometer LCMS-8040. The linear range of the calibration curves of these hormones was excellent with the correlation coefficients varying between 0.9974 and 0.9999. The precision was determined by analyzing consecutive 6 times (n = 6) for each of the low-, medium- and high-concentration mixed standard solutions. The RSD of retention time and peak area obtained was 0.0102 - 0.161% and 0.563 - 6.55% respectively, indicating good instrument precision.

The recovery of the spiked milk sample matrix ranged between 61.00% and 110.9%. The limit of quantitation of the method was determined to be 0.14~0.97 5g/kg; and the limit of detection is lower than the national standard stipulated in GB/T 21981-2008 "Hormone Multi-Residue Detection Method for Animal-derived Food - LC-MS Method". The described instrument and method demonstrates high sensitivity and meets the requirements for detection of hormones in milk.

© Shimadzu Scientific Instruments, 2018

First Edition: July 2018

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