UPLC–ESI-Q-TOF-MSE identification of urinary metabolites of the emerging sport nutrition supplement methoxyisoflavone in human subjects

Lecompte, Yannick; Rosset, Martine; Richeval, Camille; Humbert, Luc; Arpino, Patrick

doi:10.1016/j.jpba.2014.03.031

Cited by 12 publications

(8 citation statements)

References 24 publications

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“…As a consequence, a complex mix of metabolites can be analyzed in a single run, no precursor ion is selected for individual fragmentation and fragment ions can be related to their precursors using a mass fragmentation software and high-resolution mass databanks. This technique was already applied with success in various metabolomic and proteomic studies [31][32][33][34][35] including the identification of major carotenoids and chlorophylls in Dunaliella salina [30] and Porphyridium purpureum [30]. For the UPLC-MS E analysis of Ht pigments, parent and fragment ions with high resolution m/z were compared to our MS E pigment database, completed with the commercially available standard dinophytes pigments.…”

Section: Uplc-ms E Analysis Of Ht Pigments Purified By Rp-hplcmentioning

confidence: 99%

Antimelanoma activity of Heterocapsa triquetra pigments

et al. 2017

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Section: Uplc-ms E Analysis Of Ht Pigments Purified By Rp-hplcmentioning

confidence: 99%

Antimelanoma activity of Heterocapsa triquetra pigments

et al. 2017

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“…7 Among them, isoflavones, often classified as "phytoestrogens" due to their weak estrogenic activity, may be of interest in sports doping for their estrogenic and/or antioxidant properties. 8,9 The isoflavones structure differs from the isomeric flavones only for the position of phenyl B ring ( Figure 1B). The consumption of food containing a large amount of flavonoids seems to be adjuvant for the course of cardiovascular diseases, cholesterolemia, premenstrual syndrome, menopause, and osteoporosis.…”

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, due to their low concentration in food and to their non‐optimal oral bioavailability, the actual effects of dietary flavonoids are moderately low . Among them, isoflavones, often classified as “phytoestrogens” due to their weak estrogenic activity, may be of interest in sports doping for their estrogenic and/or antioxidant properties . The isoflavones structure differs from the isomeric flavones only for the position of phenyl B ring (Figure B).…”

Section: Introductionmentioning

confidence: 99%

“…Based on the biopharmacological properties of their natural analogs, synthetic isoflavones have been designed, synthesized, and studied for their biological effects. Among them, special attention has been focused on methoxyisoflavone (5‐methyl‐7‐methoxy‐isoflavone) (Figure C) and ipriflavone (7‐isopropoxy‐isoflavone) (Figure D) …”

Section: Introductionmentioning

confidence: 99%

“…Among them, special attention has been focused on methoxyisoflavone (5-methyl-7-methoxy-isoflavone) ( Figure 1C) and ipriflavone (7-isopropoxy-isoflavone) ( Figure 1D). 8 In the 1970s, animal studies showed the anabolic properties of methoxyisoflavone in terms of increased protein synthesis and decreased cortisol blood level. 14 Human studies did not show significant modification of some key parameters usually considered in the assessment of anabolic properties (among them, body weight, body mass index, blood cortisol level, and isokinetic peak force) and for this reason the anabolic and ergogenic properties of methoxyisoflavone have not been further explored.…”

Section: Introductionmentioning

confidence: 99%

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Synthetic isoflavones and doping: A novel class of aromatase inhibitors?

Iannone

Botrè

Cardillo

et al. 2018

Drug Testing and Analysis

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Anectodical information suggests that flavonoids may be widely used among athletes for their multiple biochemical and pharmacological effects. We have evaluated in vitro the effects of two synthetic isoflavones, methoxyisoflavone and ipriflavone, on the catalytic activity of human aromatase (CYP19), the enzyme catalyzing the conversion of androgens (ie, testosterone or androstenedione) to estrogens (ie, estradiol and estrone). The potential inhibitory effect was evaluated by measuring the rate of aromatization of testosterone, monitored by gas chromatography-mass spectrometry (GC-MS), both in the presence and in the absence of methoxyisoflavone or ipriflavone, comparing their effects with those of synthetic aromatase inhibitors (formestane, anastrozole, and aminoglutethimide) presently included in the list of prohibited substances and methods, and of natural flavonoids (chrysin, quercetin, and daidzein), that are known inhibitors of CYP19. The preliminary results of our in vitro study show that methoxyisoflavone and ipriflavone act as competitive inhibitors of aromatase, the degree of inhibition measured in vitro being of the same order of magnitude of that of the aromatase inhibitors commonly used in anti-estrogenic therapies. Our preliminary in vitro results indicate that, in principle, a sufficiently large intake of isoflavones could alter the kinetics of the dynamic equilibria between androgens and estrogens, suggesting their monitoring in doping control routine analysis.

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An investigation on the metabolic pathways of synthetic isoflavones by gas chromatography coupled to high accuracy mass spectrometry

Iannone

Botrè

Parenti

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale:Isoflavones are a group of flavonoids that may be of interest in sport doping because they can be used by athletes in the recovery periods after the administration of anabolic steroids, with the aim of increasing the natural production of luteinizing hormone (LH) and, consequently, the biosynthesis of endogenous androgens. Methods:The in vivo metabolism of methoxyisoflavone (5-methyl-7methoxyisoflavone) and ipriflavone (7-isopropoxyisoflavone), respectively present in a dietary supplement and in a pharmaceutical preparation, was investigated. The study was carried out by the analysis of urinary samples collected from male Caucasian subjects before, during and after the oral administration of methoxyisoflavone or ipriflavone. After enzymatic hydrolysis and liquid-liquid extraction, all urinary samples were analyzed by gas chromatography/quadrupole time-of-flight (qTOF MS system/qTOF) electron ionization mass spectrometry (EI-MS).Results: Eight metabolites of methoxyisoflavone and six metabolites of ipriflavone were isolated. The corresponding accurate mass spectra are specific for isoflavone structures and revealed also a retro-Diels-Alder fragmentation. Conclusions:When excreted in large amounts, the urinary metabolites of methoxyisoflavone and ipriflavone can be traced to potential confounding factors in doping analysis. As methoxyisoflavone and ipriflavone have been shown to inhibit the enzyme aromatase, thus interfering with the normal metabolic pathways of testosterone, the detection of their intake, by screening for the presence of their main metabolites in urine, might be helpful in routine doping control analysis.

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UPLC–ESI-Q-TOF-MSE identification of urinary metabolites of the emerging sport nutrition supplement methoxyisoflavone in human subjects

Cited by 12 publications

References 24 publications

Antimelanoma activity of Heterocapsa triquetra pigments

Antimelanoma activity of Heterocapsa triquetra pigments

Synthetic isoflavones and doping: A novel class of aromatase inhibitors?

An investigation on the metabolic pathways of synthetic isoflavones by gas chromatography coupled to high accuracy mass spectrometry

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