Isolation and Characterization of a Novel Sulfoglycolipid, ‘ Seminolipid,’ from Boar Testis and Spermatozoa*

Abstract

1. Lipids were extracted from boar testis and spermatozoa. After partition by the procedure of Folch et al. (J. Biol. Chem., 226, 497 (1957)) at least three glycolipids were found in the lower organic phase. 2. The main glycolipid was purified on silicic acid columns with chloroform-acetone and studied with infrared spectrometry disclosing the presence of sulfate ester and absence of amide linkages in the molecule. The absorption at 875 cm−1 suggested the presence of β-anomeric configuration of hexopyranoside. 3. It contained equimolar amounts of fatty acid, galactose, and sulfate. Presence of alkyl ether of glycerol was also demonstrated by GLC** as TMS-derivative. 4. NMR spectra indicated that the O-acyl group is attached to the carbon-2 of glycerol. 5. With these results and those of methylation study the structure of the main glycolipid was proposed as 1-O-alkyl-2-O-acyl-3-[β-3'-sulfogalactosyl]-glycerol. Almost all the constituent fatty acids were palmitic, and approx. 80% of glyceryl ethers was chimyl alcohol. 6. The concentrations of the sulfoglycolipid in testis and spermatozoa were approx. 0.3 and 1.0 μmole/g tissue or wet cells, respectively.