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The Journal of Lipid Research, Vol. 39, 2005-2020, October 1998
Copyright © 1998 by Lipid Research, Inc.

Sterols affecting meiosis: novel chemical syntheses and the biological activity and spectral properties of the synthetic sterols

Benfang Ruana, Shinya Watanabeb, John J. Eppigb, Christopher Kwoha, Natasha Dzidica, Jihai Panga, William K. Wilsona, and George J. Schroepfer, Jr.a
a Departments of Chemistry and of Biochemistry and Cell Biology, Rice University, 6100 Main Street, Houston, TX 77251-1892
b Jackson Laboratory, Bar Harbor, ME 04609-1500

Correspondence to: George J. Schroepfer, Jr..

4,4-Dimethyl-5{alpha}-cholesta-8,14,24-trien-3ß-ol (I) from human follicular fluid and 4,4-dimethyl-5{alpha}-cholesta-8,24-dien-3ß-ol (II) from bull testes have been reported to activate meiosis in mouse oocytes (Byskov et al., 1995. Nature. 374: 559–562). Described herein are new chemical syntheses of I, II, and the {Delta}8(14),24 analog XXII. A critical step in these syntheses was a remarkably high yield side chain oxidation of 3ß-acetoxy-4,4-dimethyl-5{alpha}-cholest-8(14)-en-15-one to the corresponding C24 24-hydroxy compound VI. Oxidation of VI to the aldehyde, followed by Wittig olefination gave 3ß-acetoxy-4,4-dimethyl-5{alpha}-cholesta-8(14),24-dien-15-one. Reduction with sodium borohydride to the 15ß-hydroxysteryl ester, dehydration with sulfuric acid in CHCl3, and saponification furnished I in high purity. Reduction of VI with sodium borohydride to the 15-hydroxysteroid followed by dehydration gave 3ß-acetoxy-4,4-dimethyl-5{alpha}-chola-8,14-dien-24-ol. Hydrogenation over Raney nickel gave the monounsaturated {Delta}8(14) and {Delta}8 compounds. Oxidation to the corresponding aldehydes followed by Wittig olefination and saponification gave II and XXII. Chromatographic, mass spectral, and 1H and 13C nuclear magnetic resonance spectral data have been presented for the synthetic sterols and their derivatives. I, II, XXII, and their {Delta}8,14 and {Delta}7,14 analogs, at 3 µg per ml, caused a resumption of meiosis in mouse oocytes in the presence of hypoxanthine (3.5 mM). Under the same conditions, {Delta}5 and {Delta}5,7 sterols were inactive.

—Ruan, B., S. Watanabe, J. J. Eppig, C. Kwoh, N. Dzidic, J. Pang, W. K. Wilson, and G. J. Schroepfer, Jr. Sterols affecting meiosis: novel chemical syntheses and the biological activity and spectral properties of the synthetic sterols. J. Lipid. Res. 1998. 39: 2005–2020.

Supplementary key words: mass spectrometry, nuclear magnetic resonance


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