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Chemical Compound Review:

CPD-272 (8S,9R,10R,11R,13S,14S)-17- ethanoyl-11...

Synonyms: HMDB00920, AC1L98OM, C03747, 80-75-1, 11a-Hydroxyprogesterone, ...

Lisurek, M. et al., Lenasi, H. et al., Lövgren, T. et al., Johnson, W.S. et al.

Lenasi, Breskvar,

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High impact information on C03747

Asymmetric total synthesis of 11alpha-hydroxyprogesterone via a briomimetic polyene cyclization [1].
Rhizopus nigricans (R. nigricans) transforms fungitoxic progesterone into the less toxic 11alpha-hydroxyprogesterone which is then able to exit the mycelia into the surrounding water [2].
Furthermore, the hydroxylation activity was quantified for all monohydroxylation products (15beta-hydroxyprogesterone, 6beta-hydroxyprogesterone, 11alpha-hydroxyprogesterone, and 9alpha-hydroxyprogesterone) [3].
For this purpose a combination of comparative HPLC and electrospray ionisation collision induced dissociation mass spectrometry (ESI CID MS) was established and applied for rapid identification of the steroids, which were identified as 11alpha-hydroxyprogesterone and 9alpha-hydroxyprogesterone [3].
The micellar solubilities of ethinyl estradiol and both corticosterone and hydrocortisone were independnet of the presence of each other while the solubility of 11alpha-hydroxyprogesterone was enhanced by ethinyl estradiol [4].

References

Asymmetric total synthesis of 11alpha-hydroxyprogesterone via a briomimetic polyene cyclization. Johnson, W.S., Brinkmeyer, R.S., Kapoor, V.M., Yarnell, T.M. J. Am. Chem. Soc. (1977) [Pubmed]
Specific interactions of steroids, arylhydrocarbons and flavonoids with progesterone receptors from the cytosol of the fungus Rhizopus nigricans. Lenasi, H., Breskvar, K. J. Steroid Biochem. Mol. Biol. (2004) [Pubmed]
Identification of monohydroxy progesterones produced by CYP106A2 using comparative HPLC and electrospray ionisation collision-induced dissociation mass spectrometry. Lisurek, M., Kang, M.J., Hartmann, R.W., Bernhardt, R. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
Simultaneous solubilization of steroid hormones I: estrogens and C21 steroids. Lövgren, T., Heikius, B., Lundberg, B., Sjöblom, L. Journal of pharmaceutical sciences. (1978) [Pubmed]

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