Infrared Spectrometry Applied to Steroid Structure and Metabolism

Jones, Richard N.; Dobriner, Konrad

doi:10.1016/s0083-6729(08)60832-8

Cited by 45 publications

(3 citation statements)

References 49 publications

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“…The shift of the absorption maximum from 231 µ for XVII to 240 µ for XIX indicates loss of the tertiary hydroxyl group at carbon atom 5. It is in good agreement with the shifts of ultraviolet maxima of A^androsten-17/3-ol-3-one, X"L 230 m,u (19) to were absorption bands at 1667,1627, and 1608 cm-1 characteristic of the presence of a A1• 4-diene-3-ketone system (22,23). These bands exhibited only minor shifts from those expected (C=0 stretching band-1666 to 1660 cm-1, C=0…”

supporting

confidence: 83%

INVESTIGATIONS ON STEROIDS. XXII. STUDIES ON OUABAGENIN. I^*

Florey¹,

Ehrenstein²

1954

J. Org. Chem.

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Of the therapeutically important cardiac glycosides, ouabain is the only one for which the exact structure of the aglycone (ouabagenin) still has to be established. Ouabain was discovered and so named by Arnaud (1) who in 1888 isolated from the bark and roots of the ouabaio tree (Acokanthera ouabaio) a toxic glycoside which was used by the Somalis of East Africa as an arrow poison. Later ( 2 ) he found the same glycoside in another arrow poison, the in6e or onaye of the Pahouins which was prepared from the seeds of Strophanthus gratus (S. glaber). The name g-strophanthin, introduced by Thoms (3, pp. 114, 119) to distinguish it from the strophanthins of other species, is frequently used in the German literature for ouabain. Of all cardiac active principles, ouabain is the most easily obtainable since it can be isolated and crystallized from the seeds of Strophanthus gratus in 5 % yield (4).As early as 1898 Arnaud (5) identified rhamnose as the sugar moiety of ouabain.Efforts to prepare the true aglycone (ouabagenin) remained fruitless for a long period of time. Various modifications of acid and enzymatic hydrolysis had yielded only resins which were the result of dehydration and possibly simultaneous polymerization. It was a major accomplishment when in 1942 Mannich and Siewert (4) succeeded in preparing the true crystalline aglycone by hydrolysis of its acetonide which in turn had been obtained by treatment of the glycoside with small amounts of concentrated hydrochloric acid in acetone. The early investigators, therefore, studied the crystalline glycoside rather than the altered aglycone. Jacobs (6) established for ouabain the formula CaH44012.

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supporting

confidence: 83%

INVESTIGATIONS ON STEROIDS. XXII. STUDIES ON OUABAGENIN. I^*

Florey¹,

Ehrenstein²

1954

J. Org. Chem.

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“…He was working in collaboration with Konrad Dobriner of the Memorial Hospital in New York in an attempt to fi nd a clue as to the origin of cancer. Together they had compiled a catalog of the infrared spectra of a large number of ketosteroids and had made interesting correlations between the frequency of the carbonyl group and its position in the ketosteroid framework (2). I decided to see if intensities could add any useful infonnation and made a study of methods for measurilll g the intensities of bands with spectrometers of limited resolv ing power, such as were available at that time (3).…”

Section: Ramsaymentioning

confidence: 99%

Molecular Spectroscopy: Some Personal Reminiscences

Ramsay¹

1994

Annual Review of Physical Chemistry

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“…triplet 1675-1666cm-1, 1631-1626cm-1, 1610-1605cm-1 is characteristic of the grouping A14-3-keto (Jones & Dobriner, 1949;Jones & Herling, 1954;Peterson et al, 1953) it was suspected that a dehydrogenation of Reichstein's compound S in the 1,2 position had taken place. Both the [D1i5 of +770 and the contribution of-220°of the 1,2 double bond to the molecular optical rotation agreed with the values given in the literature.…”

mentioning

confidence: 98%