Microbiological hydroxylation of steroids. Part I. Proton magnetic resonance spectra of ketones, alcohols, and acetates in the androstane, pregnane, and œstrane series

Bridgeman, J. E.; Cherry, P. C.; Clegg, A. S.; Evans, John; Jones, E. R. H.; Kasal, Alexander; Kumar, Virendra; Meakins, G. D.; Morisawa, Yusuke; Richards, E. E.; Woodgate, Paul D.

doi:10.1039/j39700000250

Cited by 95 publications

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“…Reduction of the ketone to a OH group was also confirmed by the 1 H-NMR spectrum (Table 1) with the appearance of an additional downfield multiplet at d 3.82 (w 1/2 20.0 Hz). The a-orientation of the Hatom at C(3) was inferred from the large coupling constant, which was further in agreement with the published data for 5a-steroids [12].…”

supporting

confidence: 61%

Microbial Transformation of Mesterolone

Choudhary

Sultan

Jalil

et al. 2005

Chemistry & Biodiversity

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The microbial transformation of mesterolone (= (1alpha,5alpha,17beta)-17-hydroxy-1-methylandrostan-3-one; 1), by a number of fungi yielded (1alpha,5alpha)-1-methylandrostane-3,17-dione (2), (1alpha,3beta,5alpha,17beta)-1-methylandrostane-3,17-diol (3), (5alpha)-1-methylandrost-1-ene-3,17-dione (4), (1alpha,5alpha,15alpha)-15-hydroxy-1-methylandrostane-3,17-dione (5), (1alpha,5alpha,6alpha,17beta)-6,17-dihydroxy-1-methylandrostan-3-one (6), (1alpha,5alpha,7alpha,17beta)-7,17-dihydroxy-1-methylandrostan-3-one (7), (1alpha,5alpha,11alpha,17beta)-11,17-dihydroxy-1-methylandrostan-3-one (8), (1alpha,5alpha,15alpha, 17beta)15,17-dihydroxy-1-methylandrostan-3-one (9), and (5alpha,15alpha,17beta)-15,17-dihydroxy-1-methylandrost-1-en-3-one (10). Metabolites 5-10 were found to be new compounds. All metabolites, except 2, 3, 6, and 7, exhibited potent anti-inflammatory activity. The structures of these metabolites were characterized on the basis of spectroscopic studies, and the structure of 5 was also determined by single-crystal X-ray-diffraction analysis.

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supporting

confidence: 61%

Microbial Transformation of Mesterolone

Choudhary

Sultan

Jalil

et al. 2005

Chemistry & Biodiversity

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“…The appearance of the deshielded proton at the OH-bearing C-atom as a ddat 3.76 ppm for coupling ( J = 10.6 and 4.8 Hz) with a CH2 group can be attributed to either H,-C(I) or H,-C(12) [13]. The latter situation has to be accepted, since it is the only one which leaves room for the required C(I)H, and C(II)H, groups with both steroids.…”

Section: Results Andmentioning

confidence: 97%

Agnatasterone A and B, Unusual Pregnane Steroids Isolated from the North‐East Atlantic Sponge Axinella agnata

Guella¹,

Pietra²

1988

Helvetica Chimica Acta

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Two novel pregnatrienolones isolated in very small amounts from the North-East-Atlantic demosponge Axinella ugnuta (Tetractinomorpha, Axinellida) are unique in having C(2)=C(3) (or C(3)=C(4)), C(7)=C(8), and C(16)=C(17) bonds and a 12P-OH group which, being strongly H-bonded to a 20-keto group, resists acylation. 'Hand ' k -N M R spectroscopy of the steroids and of products of their selective epoxidation or reduction allow us to propose the structures (+)-12P-hydroxy-5cc-pregna-2,7,16-trien-ZO-one ( = agnatasterone A, (+)-1), and (+)-12g-hydroxy-5cc-pregna-3,7,16-trien-20-one ( = agnatasterone B, (+)-5), for the two steroids with minimal recourse to model compounds. 1.Introduction. -In the area of natural products marine sponges of the order Axinellida have aroused much interest for a wide variety of N-containing, unusual metabolites which include isonitrile [ 11 and mixed-biogenesis terpenoids [2], as well as guanidine-derived compounds [3]. In contrast, as regards novel steroids, of which the phylum Porifera is otherwise the most various producer [4], interest in the Axinellida has been so far concentrated on some A-ring contracted C,, sterols only [5].We expand here the interest towards the Axinellida steroids, and in general the sponge steroids, by reporting on two new pregnanes from a member of the Axinellida, the North-East-Atlantic sponge Axinella agnutu. This has also an interest per se in the area of steroids as these novel pregnanes have unique structural features.In fact, though pregnane steroids exert important hormonal functions in terrestrial organisms [6], only a few of them, not possessing any peculiar structural characteristic, have been so far isolated from marine organisms. Included are free pregnanes from the distant demosponge Haliclonu rubens (Ceractinomorpha, Haposclerida) [7], the alcyonacean corals Gersernia rubijormis [gal and Cupnellu sp. nov. and Cupnellu erecta [gb], and the gorgonian Telesto riisei [8c], other than aglycones of starfish saponins [9].The structural elucidation of steroids is not easily accomplished by NMR techniques due to many closely lying signals, particularly in the 'H-NMR spectrum even at high magnetic field. Two approaches are currently followed. One is to place much emphasis on "C-NMR data in comparison with reference steroids of known structure [lo]. The other approach mainly relies on 'H-NMR data [ll], thus requiring much time on a latest generation, high-field NMR spectrometer in order to carry out two-dimensional experiments at high resolution. This [l 11, under favourable circumstances, allows to assign all "C and ' H resonances, though large amounts of steroids are needed. Therefore, the second approach [ 1 I] has been used with known steroids as models.

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“…The stereochemistry of H-3 was determined to be α-oriented due to its downfield shifted broad multiplet at δ H 3.96 (W 1/2 = 20.0 Hz) 10,11 . The stereochemistry of the side chain of 2 was established by the comparison with the known compounds (7-10) [4][5][6] and literature data of similar compounds.…”

Section: Resultsmentioning

confidence: 99%

Six novel steroids from culture of basidiomycete Polyporus ellisii

Wang

Zhang

Liu

et al. 2012

Nat. Prod. Bioprospect.

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Investigation of the culture of basidiomycete Polyporus ellisii led to the isolation of a novel compound 3β,9α,15α-trihydroxy-(22E,24R)-10(5→4)-abeo-ergosta-6,8(14),22-trien-5-one (1) with a new 5/7/6/5 ring system of ergosterol skeleton. In addition, five new steroids, 5β,6β-epoxy-3β,7α,9α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (2), 5β,6β-epoxy-3β,7α-dihydroxy-(22E,24R)-ergosta-8(14),22-dien-15-one (3), 5α,6α-epoxy-3β,9α,15α-trihydroxy-(22E,24R)-ergosta-8(14),22-dien-7-one (4), 15α-acetoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (5), 15β-methoxy-(22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), along with four known ergosterols (7-10), were obtained. All structures were elucidated based on 1D and 2D NMR spectral data. New compounds were evaluated for cytotoxicity against five human cancer cell lines, only compound 4 was found to exhibit a favorable cytotoxicity profile toward all tested tumor cell lines.

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Microbiological hydroxylation of steroids. Part I. Proton magnetic resonance spectra of ketones, alcohols, and acetates in the androstane, pregnane, and œstrane series

Cited by 95 publications

References 0 publications

Microbial Transformation of Mesterolone

Microbial Transformation of Mesterolone

Agnatasterone A and B, Unusual Pregnane Steroids Isolated from the North‐East Atlantic Sponge Axinella agnata

Six novel steroids from culture of basidiomycete Polyporus ellisii

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