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Quantitative-Profiling Method of Serum Steroid Hormones By Natural Products and Bioprospecting https://doi.org/10.1007/s13659-019-0204-3 ORIGINAL ARTICLE Quantitative‑Profling Method of Serum Steroid Hormones by Hydroxylamine‑Derivatization HPLC–MS Qi Liu1 · Quan Chi1 · Ru‑Ting Fan1 · Hui‑Dong Tian1 · Xian Wang1 Received: 14 March 2019 / Accepted: 3 April 2019 © The Author(s) 2019 Abstract A sensitive and rapid high performance liquid chromatography–mass spectrometry (HPLC–MS) method was developed and validated for simultaneous quantifcation of ten steroid hormones, including estrogens, androgens, progesterones, and corticosteroids four classes of steroids. The following ten steroid hormones were analyzed: progesterone, 21-deoxycortisol, estrone, 4-androstenedione, testosterone, dihydro-testosterone, androstenone, dehydroepiandrosterone, corticosterone and cortisone. Stable deuterated isotopes were used as internal standards for quantifcation. Sample preparation with and with- out derivatization were performed after liquid–liquid extraction, and the corresponding results were compared according to sensitivity and selectivity. Hydroxylamine derivatization was found to improve the ionization efciency of the analytes for electrospray ionization MS analysis. The gradient of mobile phase and experimental parameters for HPLC separation were optimized. The lower limits of quantifcation were in the range of 0.05–5 ng mL−1 with wide linear range for the ten steroid hormones. The intra-day precision < 11.1% and recovery of 84.5–120% with negligible matrix efect were achieved, where within the acceptance limits of the FDA guideline. Total HPLC–MS analysis time was 6 min. This method enables simul- taneous quantifcation of steroids in human serum. It will be helpful for the serum steroid profling in order to understand various endocrinology diseases. Graphical Abstract O N H O O H H H NH2OH + HH HH HH HO HO N O N 7 8 6 10 9 5 2 1 3 4 23456 Time (min) Keywords Steroids · Derivatization · High performance liquid chromatography–mass spectrometry (HPLC–MS) · Quantitative-profling Extended author information available on the last page of the article Vol.:(0123456789)1 3 Q. Liu et al. 1 Introduction by LC–MS with the lowest detection limit of 10 pg mL−1 [17–24]. Keski-Rahkonen et al. [19] used hydroxylamine Steroid hormones are a class of tetracyclic aliphatic hydro- hydrochloride solution as derivatization reagent after liq- carbons with cyclopentane polyhydrophenanthrene nuclei, uid–liquid extraction (LLE) and other some pretreatments, which play an important regulatory role in various physi- and the sensitivity of seven steroid hormones increased ological activities of human body and are indispensable significantly. The hydroxylamine solution is the only hormones for maintaining life [1]. Steroids usually bind derivative reagent that can simultaneously derive estro- to nuclear receptors at a very low concentration of nano- gens, androgens, corticosteroids and progesterones [25]. molar or pico-molar levels. Because steroid hormones pre- Although derivatization is shown to improve the ionization sent in very low concentration in organisms, the structures of analytes, it can also complicate the sample preparation of diferent steroid hormones are very similar and their process and uncontrollable reactions, such as geometric polarity is relatively small, it is of challenge to detect and isomerization [15]. Therefore, it is worth considering and quantify steroids with high precision and accuracy. evaluating that whether or not derivatization has an advan- Immunoassay is the mainstream method for steroid tage over non-derivatization method according to sensitiv- analysis in clinic in the past few decades, which has the ity, specifcity and efciency. advantages of high throughput and fast speed. However, Aberrant changes of serum steroid hormones are closely this method is vulnerable to interference by body fuid associated with many endocrinological diseases, it is cur- matrix or structural analogues, resulting in the lack of rently urgent need to develop a rapid and sensitive method specifcity and accuracy [2, 3]. Therefore, gas chromatog- for profling serum steroid hormones by which we can con- raphy mass spectrometry (GC–MS) was later used as the siderably improve the diagnosis and therapeutics against the most accurate method [4, 5]. However, the analysis time of diferent conditions. In the present work, we aims at devel- a GC–MS assay is often above 30 min, and its sensitivity is oping a rapid and sensitive method for simultaneous deter- not as good as that of immunoassay [6]. Although GC–MS mination of ten steroid hormones, and to compare the difer- has a long history in steroid analysis, liquid chromatogra- ence in sensitivities for the pretreatments with and without phy-mass spectrometry (LC–MS) has become the current the derivatization of hydroxylamine. The method has three trend [7, 8]. LC–MS, LC–MS/MS methodology have been advantages that are small sample consumption, short detec- proved to have higher selectivity, sensitivity, throughput tion time and more hormones detected at one injection. and simpler sample pretreatment process than radioim- munoassay, GC–MS and GC–MS/MS [8, 9]. The structural characteristics of steroid hormone lead to 2 Results and Discussion low ionization efciency, which reduces sensitivity. In MS, ionization efciency is closely related to hydroxyl, double 2.1 Chromatography bond and carbonyl groups contained in steroid hormone structure [10]. Some trace and non-ionizable hormones Because of the advantages of improving separation ability, cannot be detected by conventional methods, but with shortening analysis period and improving peak shape, gradi- the continuous improvement of ionization technology, ent elution was used in this experiment. The mobile phase chemical derivatization has become a mature strategy in consisted of phase A (0.1% formic acid in methanol) and improving the sensitivity and detection limit of steroid phase B (0.1% formic acid in water). Six gradients were opti- −1 hormones [11, 12]. It not only improves the ionization mized in gradient elution experiment. T1 (0.6 mL min ), −1 −1 efciency during electrospray ionization (ESI) process T2 (0.5 mL min ) and T3 (0.4 mL min ) were used to by adding ionizable groups to the analyte which makes optimize the fow rate, and T4 (50% A), T5 (60% A) and T6 more analytes charged into mass spectrometry, but also (70% A) were used to optimize the initial phase A ratio. The changes the structure of the analyte and chromatographic results showed that low fow rate could increase the sepa- separation behavior, and so more structural analogues or ration degree of each hormones, but the retention time of interferences can be separated. each hormones was relatively prolonged. Diferent phase A There are various derivatization methods for steroid ratio at the beginning of the gradients had a great impact on hormones. Estrogen can be treated with salmsulfonyl the separation degree. When the ratio of phase A was high, chloride or lipid derivatization [13, 14], whereas androgen the separation degree of the early stage peak was smaller, can be derived with pyridinic acid [15, 16]. With LC–MS and that of the later stage peak was larger. However, when analysis, the detection limit of the above methods can its ratio was low, the separation degree of the peak in the reach < 10 pg mL−1. Other derivatives, such as alkyla- early stage was larger, whereas the separation degree of the tion, silylation and 2-hydrazinopyridination were detected peak in the later stage was smaller and the total retention time was delayed. For the above reasons, the fow rate of 1 3 Quantitative-Profling Method of Serum Steroid Hormones by Hydroxylamine-Derivatization HPLC–MS 4 6 400 4-androstenedione derivative progesterone derivative 5 cortisone derivative 7 300 a.u.) 5 4 10 200 3 3 2 100 8 1 2 Abundance (10 1 6 Peak area ratio (Analyte/IS) 5 9 0 0 10 20 30 40 50 60 23456 Time (min) Time (min) Fig. 3 Fig. 1 Derivative efciencies of diferent reaction times for the rep- The extracted ion chromatogram (EIC) of ten steroids with- resentative steroids in human serum at reaction temperature of 40 °C out derivatization at the concentration of 500 ng mL−1. 1—cortisone; 2—21-deoxycortisol; 3—corticosterone; 4—4-androstenedione; 5— dehydroepiandrosterone; 6—estrone; 7—testosterone; 8—dihydrotes- tosterone; 9—androsterone; 10—progesterone 320 4-androstenedione derivative progesterone derivative cortisone derivative 240 7 2.5 8 160 2.0 6 a.u.) 5 10 1.5 80 9 Peak area ratio (Analyte/IS) 1.0 5 0 2 1 30 40 50 60 70 Abundance (10 0.5 3 4 Temperature (°C) 0.0 23456 Fig. 4 Derivative efciencies of diferent reaction temperatures for Time (min) the representative steroids in human serum at reaction time of 20 min Fig. 2 The extracted ion chromatogram (EIC) of ten steroid deriva- tives at the concentration of 50 ng mL−1. 1—21-deoxycortisol at 40 °C were conducted and compared. Progesterone, derivative; 2—cortisone derivative; 3—corticosterone derivative; 4-androstenedione and cortisone derivatives were chosen as 4—estrone derivative; 5—progesterone derivative; 6—dehydroepian- the representatives to select the most suitable reaction time. drosterone derivative; 7—4-androstenedione derivative; 8—testoster- The results in Fig. 3 shows that the reaction time of 20 min one derivative; 9—dihydrotestosterone derivative;10—androsterone derivative gives the maximum signal response in MS. Reaction tem- peratures were also optimized at 30 °C, 40 °C, 50 °C, 60 °C and 70 °C, respectively. As shown in Fig. 4, the reaction at 0.5 mL min−1 and the initial phase A ratio 60% were chosen 40 °C gives the highest derivatization efciency. as the optimized chromatographic condition. Under this con- dition, the steroid hormones were separated well, with little 2.3 Comparison of the Sample Analysis With interference from other substances (Figs. 1, 2). and Without Derivatization 2.2 Derivatization The analysis results of samples pretreated only by LLE were compared with those pretreated by LLE and derivatization.
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