Die Konstitution des Ouabagenin‐monoacetonids. Glykoside und Aglykone, 141. Mitteilung

Tamm, Ch.

doi:10.1002/hlca.19550380118

Cited by 24 publications

(1 citation statement)

References 22 publications

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“…The many Il-hydroxy steroids of the plant kingdom are exemplified by ouabagenin (Tamm, 1953), acovenosigenin (Schlegel, Tamm & Reichstein, 1955) and the sapogenin, ruscogenin (Benn, Colton & Pappo, 1957), which is I/3-hydroxydiosgenin. It is not appropriate to review here the extensive range of 1-oxygenated products isolated after incubation of steroids with fungi or moulds, though it is necessary to carry in mind the possibility that substances found in urine may be products of the activity of gut flora.…”

Section: Discussionmentioning

confidence: 99%

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

Edwards

Trafford

1968

Biochemical Journal

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1. Four substances from the urine of a hypertensive newborn girl were partially characterized and shown to be 17oc-hydroxy-5, B-pregnane-1,3,20-trione, 3oc,17a-dihydroxy-5,B-pregnane-1,20-dione, 3a,17oc,20ac-trihydroxy-5p-pregnan-1-one and 5/3-pregnane-lB,3oc,17a,20c-tetrol. 2. The characterization rested mainly on RM analysis of the substances and their derivatives by glycol fission, providing evidence for position and degree of substitution and for steroidal character. Supporting evidence was provided by chemically specific location reactions. 3. Certain problems in the manipulation of these ,B-disubstituted steroids are discussed.The high 17-hydroxy corticosteroid excretion of patient S.C. when 1-3 weeks old and grossly hypertensive has been described elsewhere (Edwards, Harvey & Knight-Jones, 1968 MATERIALS AND METHODSFull details of the procedures used for the isolation of urinary steroids are described elsewhere (Edwards, 1968a) and in the present instance consisted of the following steps. Urine samples (6 days' collection, age between 8 and 20 days) from S.C. during her period of high 11-oxygenation index (ratio of metabolites of 17-hydroxylated precursors of cortisol to metabolites of cortisol; Edwards, Makin & Barratt, 1964) (Stevens, 1964). Each substance was homogeneous on the criterion that portions from the forward and rear portions ofa chromatographed zone on rechromatography gave zones side by side of identical RF values.The chemical transformations used were (i) borohydride reduction and (ii) periodate oxidation, both carried out as described by Edwards et al. (1964), and (iii) oxidation with Jones reagent carried out as described by Djerassi, Engle & Bowers (1956), but with trebled proportion of acetone. RM analysis procedure. RM values were calculated from RF values and referred to the root system of the family (light petroleum-methanol-water, 5:4:1, by vol.) as RMO values by correcting for the effects of benzene replacing light petroleum (Kabasakalian & Basch, 1960;Edwards, 1968a). Observed ARM values were compared with reference values (Table 1) and the latter used to indicate likely structural changes. For clarity the ARM value observed in changing from substance of structure A to structure B was signified ARM [A--B]. It was presumed that substances with RMO values differing by less than 0-07 (S.D. ofrepetition of a value on different occasions) were in fact one substance.Referencel-hydroxysteroid. loc-Hydroxy-5oc-androstane-3,17-dione samples from Dr Fukushima and Dr Foell were found to be identical with the exception of a small proportion of contaminant in the latter. This was assumed to be the lfl-isomer, since other isomerization was unlikely from the method of preparation. A similar contaminant was present in the lac-hydroxyandrost-4-ene-3,17-dione sample. The lc,3,B-dihydroxy-50c-androstan-17-one sample was uncontaminated.Other reference steroids were prepared by unambiguous chemical transformations and were purified by chromatography, but there was insufficient material available...

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Section: Discussionmentioning

confidence: 99%

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

Edwards

Trafford

1968

Biochemical Journal

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Über pflanzliche Herzgifte, XXIX. Mitteil.: Zur Konstitution des Ouabagenins¹⁾

Tschesche

Snatzke

1955

Chem. Ber.

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Ouabagenin bildet leicht ein 1.5.19‐Orthoformiat, in dem 2 freie Oxygruppen noch acetyliert und zum Keton oxydiert werden können. Die Reduktion des Diketons mit Natriumborhydrid liefert ein neues Diol, das nur ein Monoacetat ergibt. Es wird dargelegt, daβ Ouabagenin sehr wahrscheinlich eine 11‐Oxy‐Verbindung ist und daß alle seine Hydroxyle außer dem an C11 β‐Konfiguration haben müssen. Für die Bildung des β‐Ouabagenin‐diacetates aus Aceton‐ouabagenin über Diacetyl‐aceton‐ouabagenin wird angenommen, daβ eine Umlagerung auf der Stufe vom Aceton‐ouabagenin zu seinem Diacetyl‐Derivate erfolgt.

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Über die Oxydation mit CrO₃ in Dimethylformamid

Snatzke

1961

Chem. Ber.

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Die Konstitution des Ouabagenin‐monoacetonids. Glykoside und Aglykone, 141. Mitteilung

Abstract: Volumen XXXVIII, Fasciculus I (1955

Cited by 24 publications

References 22 publications

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

Über pflanzliche Herzgifte, XXIX. Mitteil.: Zur Konstitution des Ouabagenins¹⁾

Über die Oxydation mit CrO₃ in Dimethylformamid

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Die Konstitution des Ouabagenin‐monoacetonids. Glykoside und Aglykone, 141. Mitteilung

Abstract: Volumen XXXVIII, Fasciculus I (1955

Cited by 24 publications

References 22 publications

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

Über pflanzliche Herzgifte, XXIX. Mitteil.: Zur Konstitution des Ouabagenins1)

Über die Oxydation mit CrO3 in Dimethylformamid

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Über pflanzliche Herzgifte, XXIX. Mitteil.: Zur Konstitution des Ouabagenins¹⁾

Über die Oxydation mit CrO₃ in Dimethylformamid