Isolation and structure determination of sulfonoquinovosyl dipalmitoyl glyceride, a P-selectin receptor inhibitor from the alga Dictyochloris fragrans.
Bioassay-guided fractionation of the marine alga Dictyochloris fragrans led to the isolation and identification of sulfonoquinovosyl dipalmitoyl glyceride (1). The structure of 1 was determined by a combination of spectroscopic methods. On the basis of P-selectin inhibition assays (i.e., P-selectin-IgG ELISA, cell binding assay of receptor globulin, and platelet:HL60 adhesion, it was demonstrated that 1 selectively blocks the P-selectin-ligand interaction in vitro and could be considered a lead compound for synthetic modification in order to design more potent inhibitors of cell adhesion processes that play important roles in development of inflammatory-mediated disease states.
Golik
J
J
Bristol-Myers Squibb Pharmaceutical Research Institute, Wallingford, Connecticut 06492, USA.
Dickey
J K
JK
Todderud
G
G
Lee
D
D
Alford
J
J
Huang
S
S
Klohr
S
S
Eustice
D
D
Aruffo
A
A
Agler
M L
ML
D002448:Cell Adhesion / Q000187:drug effects; D004797:Enzyme-Linked Immunosorbent Assay; D056890:Eukaryota / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018922:HL-60 Cells; D006801:Humans; D007073:Immunoglobulin E / Q000737:chemistry; D019007:P-Selectin / Q000378:metabolism*; D011946:Receptors, Antigen / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment
D006017:Glycolipids; D019007:P-Selectin; D011946:Receptors, Antigen; C106018:sulfoquinovosyl dipalmitoyl glyceride; D007073:Immunoglobulin E