- Grapefruit juice and its flavonoids inhibit 11β-hydroxysteroid dehydrogenase
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Introduction: The enzyme 11β-hydroxysteroid dehydrogenase (11β-OHSD) oxidizes cortisol to inactive cortisone. Its congenital absence or inhibition by licorice increases cortisol levels at the mineralocorticoid receptor, causing mineralocorticoid effects. We tested the hypothesis that flavonoids found in grapefruit juice inhibit this enzyme in vitro and that grapefruit juice itself inhibits it in vivo. Methods: Microsomes from guinea pig kidney cortex were incubated with cortisol and nicotinamide adenine diraucleotide (NAD) or nicotinamide adenine dinucleotide phosphate (NADP) and different flavonoids and the oxidation to cortisone measured with use of HPLC analysis. In addition, healthy human volunteers drank grapefruit juice, and the ratio of cortisone to cortisol in their urine was measured by HPLC and used as an index of endogenous enzyme activity. Results: Both forms of 11β-OHSD requiring either NAD or NADP were inhibited in a concentration-dependent manner by the flavonoids in grapefruit juice. Normal men who drank grapefruit juice had a fall in their urinary cortisone/cortisol ratio, suggesting in vivo inhibition of the enzyme. Conclusion: Dietary flavonoids can inhibit this enzyme and, at high doses, may cause an apparent mineralocorticoid effect.
- Lee, Yil Seob,Lorenzo, Beverly J.,Koufis, Theo,Reidenberg, Marcus M.
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- Selective reduction of 4,6- conjugate diene -3-one steroid compound method
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Belonging to the field of chemical pharmacy, the invention relates to a method for selective reduction of 4, 6-conjugated diene-3-one steroid, and solves the problem of low yield in hydrogen reduction. The method mainly includes the steps of: 1) adding the 4, 6-conjugated diene-3-one steroid, a liquid solvent, a catalyst, and a reducing agent hydrogen donor into a reaction kettle, performing nitrogen protection, and carrying out stirring heating till reflux; 2) carry out reflux reaction for 3-10h; 3) at the end of reaction, filtering out the catalyst; 4) distilling the solvent; 5) adding purified water after distillation; and 6) conducting cooling, pumping filtering, washing and drying to obtain a 4-ene-3-steroid crystal.
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Paragraph 0098-0105
(2019/11/21)
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- Nitrate esters of corticoid compounds and pharmaceutical applications thereof
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Compounds of the formula and use of the compounds as medicaments.
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- Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
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Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.
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- Photochemical Studies, 64. - Photostability of Glucocorticoids in the Solid State
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Most of the pharmacopoeia require that the glucocorticoids hydrocortisone (1), cortisone (2), hydrocortisone 21-acetate (3) and cortisone 21-acetate (4) must be protected from light during storage.The present study shows that irradiation of these compounds in the solid state leads to the loss of the side chain at C-17.Two-17-ketosteroids, 11β-hydroxy-4-androstene-3,17-dione (6) and 4-androstene-3,11,17-trione (7), were obtained as photoproducts (yields 3percent and 4percent, respectively).Key Words: Hydrocortisone / Cortisone / Steroids / Photochemistry
- Reisch, Johannes,Iranshahi, Lotfollah,Ekiz-Guecer, Nurten
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p. 1199 - 1200
(2007/10/02)
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- Evidence for a new biologic pathway of androstenedione synthesis from 11-deoxycortisol
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17-Hydroxyprogesterone is a well-known precursor of androstenedione in adrenal biosynthesis.This study using sheep adrenal incubations demonstrates that 11-deoxycortisol, the precursor of cortisol synthesis, also can be a precursor of androstenedione.Indeed, our data shown that androstenedione synthesis is negatively correlated to the synthesis of cortisol and cortisone.This fact allowed us to infer that this new pathway is closely related to the activity of the 11β-hydroxylase that is responsible for the synthesis of cortisol.Indeed, when the activity of this enzyme is impaired, 11-deoxycortisol follows the pathway that leads to androstenedione synthesis in the adrenals.This pathway could explain, at least in part, the marked increase of androstenedione observed in congenital adrenal hyperplasia due to 11β-hydroxylase deficiency.
- Auzeby, Andre,Bogdan, Andre,Touitou, Yvan
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- First Enantioselective Total Synthesis of (+)-Cortisone
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The intramolecular cycloaddition of an olefinic o-quinodimethane, having an optically active oxathiane system as a stereodirecting group, leads enantioselectively to A-nor B-aromatic steroids.This reaction is the key in an enantioselective total synthesis of (+)-cortisone (1).
- Nemoto, Hideo,Matsuhashi, Norikazu,Imaizumi, Mari,Nagai, Mitsuo,Fukumoto, Keiichiro
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p. 5625 - 5631
(2007/10/02)
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- Total Synthesis of ( +/-)-Cortisone. Double-Hydroxylation Reaction for Corticoid Synthesis
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Total syntheses of (+/-)-cortisone and (+/-)-adrenosterone have been achieved in 18 steps with the aid of metal-assisted new synthetic sequences in particular, ene reaction and homoenolate chemistry.A novel double-hydroxylation reaction of enol silyl ethers leading to a single step construction of the dihydroxyacetone side chain in corticoids has been developed and applied to the synthesis of cortisone, cortexolone, and 16α-methylcortexolone.
- Horiguchi, Yoshiaki,Nakamura, Eiichi,Kuwajima, Isao
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p. 6257 - 6265
(2007/10/02)
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- Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid
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This invention discloses an improved process for the production of corticoids from 17α-hydroxy steroids utilizing peroxymonosulfate.
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- Amine containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1
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- Amine containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1
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- Sulfonate containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1 and their salts.
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- Sulfonate containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1 and their salts.
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- Radiolytic degradation scheme for 60Co-irradiated corticosteroids
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The cobalt 60 radiolytic degradation products have been identified in the following corticosteroids: cortisone, cortisone acetate, hydrocortisone, hydrocortisone acetate, hydrocortisone sodium succinate, isoflupredone acetate, methylprednisolone, methylprednisolone acetate, prednisolone, prednisolone acetate, and prednisone. Two major types of degradation processes have been identified: loss of the corticoid side chain the D-ring to produce the C-17 ketone and conversion of the C-11 alcohol, if present, to the C-11 ketone. Minor degradation products derived from other changes affecting the side chain are also identified in several corticosteroids. These compounds are frequently associated in corticosteroids as process impurities or degradation compounds. No new radiolytic compounds unique to 60Co-irradiation have been found. The majority of corticosteroids have been shown to be stable to 60Co-irradiation. The rates of radiolytic degradation ranged from 0.2 to 1.4%/Mrad.
- Kane,Tsuji
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- Water-soluble steroid compounds
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Beta-cyclodextrin forms a water-soluble complex or inclusion compound with steroid compounds having a molecular structure smaller than the interior cavity in the doughnut-shaped molecular structure of beta-cyclodextrin. The resulting inclusion compounds can be used for a variety of applications including aqueous topical ophthalmic preparations and topical dermatological ointments.
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- Novel N-nitroso compounds, compositions containing such compounds, processes for their preparation and methods of treatment therewith, and novel intermediates
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This invention relates to novel N-halogenoalkyl-N-nitroso carbamates and N 4 halogenalkyl-N 4 -nitroso allophanates of steroid compounds, having an anti-tumor activity, and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds, and methods of treatment therewith.
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