Formation of 5 alpha steroids by biotransformation involving the 5 alpha-reductase activity of Penicillium decumbens.

Abstract:

:The biotransformation of a series of delta 4-3-ketosteroids by the fungus Penicillium decumbens ATCC 10436 has been investigated. Conversion to the 5 alpha-dihydrosteroid was observed for several substrates of the androstene and pregnene series: the reaction is tolerant of non-polar substituents (Cl and CH3) at C-4 of the substrate, but does not occur in the presence of a 4-hydroxyl group, or with additional unsaturation at the delta 1 or delta 6 positions. A-nor-, B-nor-, 3-deoxy-, and 3,5-cycloandrostanes are not reduced, but 6-methylenetestosterone is converted to a 6-methylene-5 alpha-dihydro derivative. Several biotransformations are reported which involve oxidoreductase activity at C-3 and/or C-17, either concomitant or independent of delta 4 reduction: the substrate specificity of the oxidoreductase processes has been examined and defined by the use of 3 alpha-hydroxy, 3 beta-hydroxy, 3-keto, 17 beta-hydroxy and 17-keto substituted steroids. In this way, the existence in P. decumbens of 3 beta-hydroxy-3-keto and 17 beta-hydroxy-17-keto oxidoreductases has been demonstrated.

journal_name

Steroids

journal_title

Steroids

authors

Holland HL,Dore S,Xu W,Brown FM

doi

10.1016/0039-128x(94)90020-5

subject

Has Abstract

pub_date

1994-11-01 00:00:00

pages

642-7

issue

11

eissn

0039-128X

issn

1878-5867

pii

0039-128X(94)90020-5

journal_volume

59

pub_type

杂志文章

相关文献

STEROIDS文献大全
  • 1H and 13C NMR characteristics of synthetic derivatives of steroid sapogenins. Part III. 16Beta,23:23,26-diepoxy side chains.

    abstract::The full assignments of the (1)H and (13)C NMR signals of steroids bearing the 16beta,23:23,26-diepoxy side chain are provided. Differentiation of the diasterotopic H-26 pair was achieved with the aid of NOESY experiments. The main substituent and steric effects associated with this moiety and their influence on the c...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2008.01.027

    authors: Vázquez-Ramírez I,Macías-Alonso M,Arcos-Ramos RO,Ruíz-Pérez KM,Solano-Ramírez DO,Iglesias Arteaga MA

    更新日期:2008-07-01 00:00:00

  • Radioimmunoassay of progesterone, 17-hydroxyprogesterone, estradiol-17beta and prostaglandin F in human corpus luteum.

    abstract::Radioimmunoassay procedures have been adapted for the assay of progesterone, 17-hydroxyprogesterone, estradiol-17beta, and prostaglandin F in human corpus luteum. The method utilises a single homogenisation and extraction of the tissue followed by fractionation of the steroids on alumina, and separation of the prostag...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(75)90076-8

    authors: Shutt DA,Shearman RP,Lyneham RC,Clarke AH,McMahon GR,Goh P

    更新日期:1975-09-01 00:00:00

  • Enzyme immunoassay for cortisol in serum using cortisol 21-amine.

    abstract::Cortisol 21-amine (21-amino-11beta,17-dihydroxy-4-pregnene-3,20-dione) was prepared and an enzyme immunoassay for cortisol in serum was established using cortisol 21-amine conjugated with alkaline phosphatase. The minimal amount of cortisol detected was 1ng/tube and the measurable range was from 1 to 80 microgram/d1, ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(78)90106-x

    authors: Kobayashi Y,Ogihara T,Amitani K,Watanabe F,Kiguchi T,Ninomiya I,Kumahara Y

    更新日期:1978-07-01 00:00:00

  • Differential binding of dexamethasone to ammonium sulfate precipitates of human adipose tissue cytosols.

    abstract::Saturation analysis of the binding of [3H]dexamethasone [( 3H]DEX) to ammonium sulfate precipitates (ASPs) confirmed the presence of a limited-capacity, high-affinity binder in human adipose tissue cytosols. Various non-radioactive steroids competed with [3H]DEX for binding to the ASPs in the following sequence: dexam...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(87)90091-2

    authors: Miller LK,Kral JG,Strain GW,Zumoff B

    更新日期:1987-06-01 00:00:00

  • Contribution of exogenous progesterone to human adrenal cortisol synthesis in vitro: a comparison of early gestation fetal and adult tissues.

    abstract::The ability of human adult adrenal to utilize progesterone (P4) for cortisol (F) synthesis in vitro has been compared with that of fetal adrenal tissue. Explant cultures were studied for 6 days using Ham's F10 medium supplemented with 10% fetal bovine serum (FBS), with or without added P4 as substrate. Short-term (4h)...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(86)90097-8

    authors: Branchaud CL,Lipowski L,Dhanani B,Goodyer CG,Lefebvre Y

    更新日期:1986-04-01 00:00:00

  • The 11 beta-hydroxysteroid dehydrogenase type II enzyme: biochemical consequences of the congenital R337C mutation.

    abstract::The 11 beta-hydroxysteroid dehydrogenase type II enzyme (11 beta HSD2) converts cortisol to cortisone, allowing the non-selective mineralocorticoid receptor to bind aldosterone. When the activity of this enzyme is compromised, as occurs in licorice intoxication or in the congenital syndrome of apparent mineralocortico...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(96)00013-x

    authors: Ferrari P,Obeyesekere VR,Li K,Andrews RK,Krozowski ZS

    更新日期:1996-04-01 00:00:00

  • Quantitative measurement of estrogen-induced ERK 1 and 2 activation via multiple membrane-initiated signaling pathways.

    abstract::Estradiol (E2) and other steroids have recently been shown to initiate various intracellular signaling cascades from the plasma membrane, including those stimulating mitogen-activated protein kinases (MAPKs), and particularly extracellular-regulated kinases (ERKs). In this study we demonstrated the ability of E2 to ac...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2003.12.003

    authors: Bulayeva NN,Gametchu B,Watson CS

    更新日期:2004-03-01 00:00:00

  • Synthesis of dehydro-oogoniol, a female-activating hormone of Achlya: the progesterone route.

    abstract::The structure of dehydro-oogoniol (3 beta,11 alpha,15 beta,29-tetrahydroxystigmasta-5,24(28)(E)-dien-7-one), a female-activating hormone of the water mold Achlya, has been confirmed by synthesis. The starting material was progesterone, which was converted to the 11 alpha, 15 beta-dihydroxy derivative by microbiologica...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(89)90019-6

    authors: McMorris TC,Le PH,Preus MW,Schow SR,Weihe GR

    更新日期:1989-03-01 00:00:00

  • On reactions of steroidal 23-oxo and 23,24-epoxysapogenins with Lewis acids.

    abstract::The reaction of 23-oxotigogenin acetate with TMSOTf in THF afforded the corresponding bisnorcholanic lactone in 60% yield. The analogous reactions carried out in dichloromethane or benzene gave the rearranged products--the isomeric spirostanic ketone (10-15%) and bisfuran (40-42%). Similar products were also obtained ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2009.02.010

    authors: Jastrzebska I,Siergiejczyk L,Tomkiel AM,Urbańczyk-Lipkowska Z,Wójcik D,Morzycki JW

    更新日期:2009-08-01 00:00:00

  • Liquid chromatography tandem mass spectrometry in study of the pharmacokinetics of six steroidal saponins in rats.

    abstract::A rapid, simple and sensitive high-performance liquid chromatography tandem mass spectrometry method was developed and validated for simultaneous determination of six main steroidal saponins in Paris polyphylla in rat plasma. Ginsenoside Rg3 was selected as the internal standard (IS). Plasma samples were pretreated wi...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2013.08.009

    authors: Wang B,Ji S,Zhang H,Zhao L,Lv L,Li Y,Zhou G,Zhang G

    更新日期:2013-12-11 00:00:00

  • Progesterone-regulated determinants of stromal cell survival and death in uterine decidua are linked to protein kinase C activity.

    abstract::This study examined the role of protein kinase C enzymatic activity as a physiologic determinant of stromal cell death in decidua basalis (DB) during pregnancy. The expression of epidermal growth factor receptor (EGF-R) and Bcl2 was used as an indicator of stromal cell proliferation/survival, whereas Bax and the occur...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(99)00044-6

    authors: Ogle TF,Dai D,George P

    更新日期:1999-09-01 00:00:00

  • Radiolabeled steroidal estrogens in cancer research.

    abstract::It has now been more than 30 years since the laboratory verification of the localization of estrogen in certain animal tissues. Much has been learned since that time regarding the details of this process, including the presence of specific receptors for these hormones in target tissues, the mechanism of ligand binding...

    journal_title:Steroids

    pub_type: 杂志文章,评审

    doi:10.1016/0039-128x(93)90069-y

    authors: Cummins CH

    更新日期:1993-06-01 00:00:00

  • Antigen-specific T cell functions are suppressed over the estrogen-dendritic cell-indoleamine 2,3-dioxygenase axis.

    abstract::Estrogen results in the suppression of experimental allergic encephalomyelitis (EAE), a frequently used experimental animal model of multiple sclerosis (MS). The mechanism by which estrogen acts in diseases with an autoimmune background is less clear. Here, we used splenic dendritic cells (DC) from the Lewis rats EAE ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2004.05.019

    authors: Xiao BG,Liu X,Link H

    更新日期:2004-09-01 00:00:00

  • Mass spectrometry and stability of t-butyldimethylsilylethers of some estrogens and androstanes.

    abstract::In addition to using radioimmunoassays for the determination of estrogens and other steroids, the possibility of using mass fragmentography for analysis was investigated. t-Butyldimethylsilyl chloride was selected as a reagent for derivatisation because it forms rather stable silylethers. In all the mass-spectra obrai...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(79)90013-8

    authors: Ballhorn L,Mueller WF,Korte F

    更新日期:1979-04-01 00:00:00

  • New pregnane glycosides from Stelmatocrypton khasianum.

    abstract::Four new pregnane glycosides, stelmatocryptonoside A, B, C, and D (1-4), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral data, the structures of 1-4 were established as 3beta, 16alpha-dihydroxy-pregn-5-en-20-one-16-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(01)00187-8

    authors: Zhang Q,Zhao Y,Wang B,Feng R,Liu X,Cheng T

    更新日期:2002-04-01 00:00:00

  • Steroid delta 4-5 beta-reductase in human mammary tumors.

    abstract::Steroid delta 4-5 alpha- and delta 4-5 beta-reductase activity was determined in 16 human mammary tumors and 8 DMBA-induced rat mammary tumors using a spectrophotometric assay. Steroid delta 4-5 alpha-reductase was present in all tumors investigated while delta 4-5 beta-reductase was detected in only 6 estrogen recept...

    journal_title:Steroids

    pub_type: 历史文章,杂志文章

    doi:10.1016/s0039-128x(79)80010-0

    authors: Abul-Hajj YJ

    更新日期:1979-01-01 00:00:00

  • Failure to detect delta 5-3 beta-hydroxysteroid oxidoreductase activity in the preimplantation rabbit embryo.

    abstract::Preimplantation rabbit embryos were incubated with pregnenolone and dehydroisoandrosterone under conditions which gave formazan precipitation by the histochemical technique. The metabolic fate of the labeled steroids was assessed simultaneously. There was no concomitant transformation of pregnenolone to progesterone a...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(81)80012-8

    authors: Bleau G

    更新日期:1981-02-01 00:00:00

  • 1alpha,3beta,5beta-trihydroxy-24-methylenecholestan-6-one: a novel steroid from a soft coral Sinularia gibberosa.

    abstract::A novel steroid, 1alpha,3beta,5beta-trihydroxy-24-methylenecholestan-6-one (gibberoketosterol) (1), along with four known steroids, was isolated from the lipophilic extracts of a Taiwanese soft coral Sinularia gibberosa. The structure of the new metabolite was determined on the basis of extensive spectral analyses and...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(03)00036-9

    authors: Ahmed AF,Dai CF,Kuo YH,Sheu JH

    更新日期:2003-04-01 00:00:00

  • Withanolides from the stems and leaves of Physalis pubescens and their cytotoxic activity.

    abstract::A phytochemical study of Physalis pubescens L. afforded twelve compounds, including six new withanolides (1, 4, and 6i-9), four new withanolide glucosides (2, 3, 5, and 6), and two known withanolides (10 and 11). Their structures were established via extensive spectroscopic analysis. The absolute configuration of 3 wa...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2016.09.002

    authors: Xia G,Li Y,Sun J,Wang L,Tang X,Lin B,Kang N,Huang J,Chen L,Qiu F

    更新日期:2016-11-01 00:00:00

  • Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.

    abstract::Two-hydroxyestrone (2OHE-1) and 16alpha-hydroxyestrone (16OHE-1) are two estrogen metabolites that may play important roles in the development or promotion of breast cancer. Our study assessed the reliability of a newly developed kit procedure for measuring 2OHE-1. Although under certain conditions the assay would not...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/s0039-128x(00)00139-2

    authors: Spierto FW,Gardner F,Smith SJ

    更新日期:2001-01-01 00:00:00

  • Estradiol mediates relaxation of porcine lower esophageal sphincter.

    abstract::Most pregnant women have symptoms of gastroesophageal reflux disease (GERD) during pregnancy. Postmenopausal hormone replacement therapy is associated with GERD. The effects of estradiol on lower esophageal sphincter (LES) motility and GERD are not clearly known. The purpose of this study is to investigate the effects...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2018.05.001

    authors: Tsai CC,Tey SL,Chang LC,Su YT,Lin KJ,Huang SC

    更新日期:2018-08-01 00:00:00

  • The ecdysteroids from the tobacco hornworm during pupal-adult development five days after peak titer of molting hormone activity.

    abstract::Six naturally occurring C27 ecdysteroids were isolated and identified from the tobacco hornworm during pupal-adult development five days after peak titer of molting hormone activity. In order of decreasing quantities the hormones were: 20,26-dihydroxyecdysone, 3-epi-20-hydroxyecdysone, 20hydroxyecdysone, 3-epi-20,26-d...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(79)90084-9

    authors: Kaplanis JN,Thompson MJ,Dutky SR,Robbins WE

    更新日期:1979-09-01 00:00:00

  • Overnight (1 mg) dexamethasone suppression testing reliably distinguishes non-cushingoid obesity from Cushing's syndrome.

    abstract::To determine the sensitivity of the overnight 1-mg dexamethasone suppression test in diagnosing Cushing's syndrome, we evaluated the cortisol responses of 55 subjects (25 non-obese individuals with body mass index less than 25 kg/m2, 20 obese individuals with body mass index greater than 30 kg/m2, and 10 patients with...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(91)90011-j

    authors: Fok AC,Tan KT,Jacob E,Sum CF

    更新日期:1991-11-01 00:00:00

  • The physiology functions of estrogen receptor α (ERα) in reproduction cycle of ovoviviparous black rockfish, Sebastes schlegeli Hilgendorf.

    abstract::This paper revealed the expression pattern of ERα in the ovoviviparous teleost, Sebastes schlegeli. In this paper, we isolated the cDNA encoding for estrogen receptor alpha of black rockfish (S. schlegeli) from its ovary, named as black rockfish ERα (brfERα). The cDNA sequence of brfERα consists of 2972bp with an open...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2011.09.014

    authors: Shi D,Wen HS,He F,Li JF,Yang YP,Chen CF,Zhang JR,Chen XY,Jin GX,Shi B,Qi BX,Li N

    更新日期:2011-12-20 00:00:00

  • Steroidal saponins from Raphia vinifera and their cytotoxic activity.

    abstract::Phytochemical analysis of the fruits of Raphia vinifera led to the isolation of four new steroidal saponins (1-4), along with six known secondary metabolites (6-10). The structures of the isolated compounds were determined based on the analyses of NMR and mass spectrometric data, and chemical degradation reactions. Am...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2020.108724

    authors: Chi GF,Sop RVT,Mbaveng AT,Omollo Ombito J,Fotso GW,Nguenang GS,Kuete V,Efferth T,Ngadjui BT

    更新日期:2020-11-01 00:00:00

  • A novel synthetic approach to (20R)- and (20S)-21-hydroxy steroids. Synthesis of a marine sterol 21-hydroxycholesterol.

    abstract::A short and efficient synthesis of steroid synthons, di(tert-butyldimethylsilyl) ethers of 3,21-dihydroxy-24-nor-chol-5-en-23-al (8 and 10) and of ethyl 3,21-dihydroxy-25-homo-chola-5,23-dien-25-oate (9 and 11), having natural (20R) and unnatural (20S) configuration from 3β-(tert-butyldimethylsilyloxy)-14α,20ξ-card-5-...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2011.01.010

    authors: Koenig H,Skiera I,Błaszczyk K,Paryzek Z

    更新日期:2011-04-01 00:00:00

  • Invalidation of a commercially available human 5α-dihydrotestosterone immunoassay.

    abstract::Enzyme immunoassays (EIA) are commonly utilized for the evaluation of androgens in biological fluids; however, careful consideration must be given to cross-reactivity with other endogenous sex-steroid hormones. Our purpose was to determine the validity of a commonly-utilized commercially-available dihydrotestosterone ...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2013.08.013

    authors: Yarrow JF,Beck DT,Conover CF,Beggs LA,Goldberger BA,Borst SE

    更新日期:2013-12-11 00:00:00

  • Metabolism of diethylstilbestrol in the C3H mouse: chromatographic systems for the quantitative analysis of DES metabolic products.

    abstract::Initial excretion studies with orally administered [monoethyl-1-3H] DES demonstrated the feces to be the principal mode of elimination of DES in the C3H mouse. Metabolic studies with tritiated DES and/or [UL-14C] DES were performed with orally dosed C3H high (MTV+) and low (MTV-) titer MMTV female mice. Extraction and...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(78)90029-6

    authors: Helton ED,Gough BJ,King JW Jr,Thenot JP,Horning EC

    更新日期:1978-04-01 00:00:00

  • Cortisol metabolism and excretion in the isolated perfused rat kidney.

    abstract::The isolated perfused rat kidney allows a simultaneous kinetic study of both the renal metabolism and the urinary excretion of cortisol and its metabolites in the rat. In this system, cortisol was completely metabolized within 120 minutes. The main renal metabolites of cortisol (cortisone, 20 reduced cortisol and 20 r...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/0039-128x(77)90052-6

    authors: Reach G,Nakane H,Nakane Y,Auzan C,Corvol P

    更新日期:1977-11-01 00:00:00

  • Increased SULT1E1 activity in HepG2 hepatocytes decreases growth hormone stimulation of STAT5b phosphorylation.

    abstract::Mouse models of cystic fibrosis (CF) display increased sulfotransferase 1E1 (SULT1E1) activity in hepatocytes of cystic fibrosis transmembrane receptor (CFTR)-deficient animals. SULT1E1 is responsible for the sulfation and inactivation of beta-estradiol (E2) at physiological concentrations. IGF-1 message levels in CFT...

    journal_title:Steroids

    pub_type: 杂志文章

    doi:10.1016/j.steroids.2008.09.002

    authors: Li L,He D,Wilborn TW,Falany JL,Falany CN

    更新日期:2009-01-01 00:00:00