Characterization of novel glycolipids from the giant cockroach (Blaberus colosseus).
A novel class of glycolipids, assigned the trivial name blaberosides, was isolated from whole head tissues of the giant cockroach (Blaberus colosseus). The class consists of two closely related families, blaberoside I and blaberoside II, each containing species differing by 26 atomic mass units. The structure of these gentiobiose-based glycoglycerolipids was elucidated by chromatographic behavior, nuclear magnetic resonance spectroscopy, mass spectrometry, and analysis of chemical degradation products and derivatives. Species in the blaberoside I family have been identified as 2-O-[6'-O-(6"-O-3-hydroxy-11-eicosenoyl-beta-D-glucopyranosyl)-bet a-D- glucopyranosyl]-3-(hexadecyloxy)-1-(3-hydroxy-11-eicosenoyl)-1,2-p ropanediol (blaberoside Ia) and 2-O-[6'-O-(6"-O-3-hydroxy-11-eicosenoyl-beta-D-glucopyranosyl)-bet a- D-glucopyranosyl]-3-(6-octadeceloxy)-1-(3-hydroxy-11-eicosenoyl )-1,2- propanediol (blaberoside Ib). Two smaller homologs of the blaberoside II family were discerned to be 2-O-[6'-O-(6"-O-3-hydroxy-11- eicosenoyl-beta-D-glucopyranosyl)-beta-D-glucopyranosyl]-3-(hex ade cyloxy)- 1,2-propanediol (blaberoside IIa), and 2-O-[6'-O-(6"-O-3-hydroxy-11-eicosenoyl-beta-D- glucopyranosyl)-beta-D-glucopyranosyl]-3-(4-octadeceloxy)-1,2-prop anediol (blaberoside IIb). These compounds are unique because they are animal origin glyceroglycolipids with a highly flexible gentiobiose backbone, and a beta-linkage of the carbohydrate to the glycerol ether at the 2 position rather than the usual 1 position.
Stoskopf
M K
MK
John F. Kennedy Institute, Johns Hopkins School of Medicine, Baltimore, Maryland 21205.
Kishimoto
Y
Y
Tanaka
T
T
Okamura
N
N
Kan
L S
LS
Cotter
R
R
Fenselau
C
C
D000818:Animals; D002247:Carbon Isotopes; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D003058:Cockroaches / Q000032:analysis*; D008401:Gas Chromatography-Mass Spectrometry; D006017:Glycolipids / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D008745:Methylation; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D002247:Carbon Isotopes; D006017:Glycolipids; D000432:Methanol