On the relationship between glycerophosphoglycolipids and lipoteichoic acids in gram-positive bacteria: II. Structures of glycerophosphoglycolipids

Abstract

1. 1. Eight glycerophosphoglycolipids were isolated from six Gram-positive bacteria. Besides sn-glycero-1-phospho-β-gentiobiosyldiacylglycerol (i) and sn-glycero-1-phospho-α-kojibiosyldiacylglycerol (ii), three novel structures have been established: 1,2- di- O-acyl-3- O-[6-( sn-glycero-1-phospho)- α- D-glucopyranosyl-(1 → 2)-(6- O-acyl- α- D-glucopyranosyl)]glycerol ( iii), 1,2- di- O-acyl-3- O-[6-( sn-glycero-1-phospho)- β- D-glucopyranosyl- → 6)- α- D-galactopyranosyl-(1 → 2)- α- D-glucopyranosyl]glycerol (iv),and 1,2- di- O-acyl-3- O-[6-( sn-glycero-1-phospho)- β- D-glucopyranosyl-(1 → 6)- α- D-galactopyranosyl-(1 → 2)-(6- O-acyl- α- D-glucopyranosyl)]iglycerol ( v). 2. 2. Compound i was isolated from Bacillus licheniformis, Bacillus subtilis and Staphylococcus aureus, compound ii from a group B Streptococcus, compounds ii and iii from Streptococcus lactis, compounds iv and v from Lactobacillus casei. Lactobacillus plantarum contained besides compounds iv and v a glycerophosphate derivative of 1,2- di- O-acyl-3- O-[ α- D-galactopyranosyl (1 → 2)- α- D- glucopyranosyl] glycerol. 3. 3. Identical structural features of the described glycerophosphoglycolipids and the corresponding lipoteichoic acids are discussed.