The scarlet letter: Reichstein's Substance S. A comparison of the angiostatic properties of 5 alpha-tetrahydro S and 5 beta-tetrahydro S.
5 beta-Tetrahydro-Reichstein's Substance S (3 alpha, 5 beta-THS) from different sources yielded variable bioassay activity in the chick chorio-allantoic membrane assay system. Physical characterization showed impure products. Synthesis of this compound by two different routes yielded active and inactive 3 alpha, 5 beta-THS. Of the other two epimers, 3 beta, 5 beta-THS (epi-THS) and 3 alpha, 5 alpha-THS (allo-THS), only the latter was active. These results suggest that the impurities present in 3 alpha, 5 beta-THS synthesized by reduction of the alpha, beta-unsaturated ketone of Substance S might be either or both the epi-/allo-epimers (3 beta, 5 beta-THS and 3 alpha, 5 alpha-THS, respectively), with only the latter contributing the positive angiostatic activity to the mixture. Of the two synthetically derived compounds, only the latter was shown to maintain the activity, whereas 3 alpha, 5 beta-THS was not antiangiogenic.
Hadd
H E
HE
Holling's Cancer Center, Charleston, South Carolina, USA.
Prztjazny
A
A
Kokosa
J M
JM
D000482:Allantois / Q000098:blood supply / Q000187:drug effects; D000818:Animals; D002642:Chick Embryo; D002823:Chorion / Q000098:blood supply / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D003350:Cortodoxone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C009412:tetrahydro-11-deoxycortisol; D003350:Cortodoxone