Chemical analysis of norrisolide-induced Golgi vesiculation.
The chemical origin of the norrisolide-induced irreversible Golgi vesiculation was studied using a variety of norrisolide probes. This natural product was found to bind to a receptor on the Golgi membranes using the perhydroindane core fragment as the recognition element. The acetylated gamma-lactol-gamma-lactone side chain of norrisolide is essential for the irreversible Golgi vesiculation and can be replaced by other electrophilic motifs without loss of biological function. In particular, compound 10 reproduces the cellular phenotype of the natural product.
Guizzunti
Gianni
G
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, 92093-0358, USA.
Brady
Thomas P
TP
Malhotra
Vivek
V
Theodorakis
Emmanuel A
EA
D000818:Animals; D000906:Antibodies / Q000378:metabolism; D000918:Antibody Specificity; D004224:Diterpenes / Q000494:pharmacology*; D005456:Fluorescent Dyes / Q000737:chemistry; D006056:Golgi Apparatus / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism; D007668:Kidney / Q000166:cytology; D008856:Microscopy, Fluorescence; D051381:Rats
D000906:Antibodies; D004224:Diterpenes; D005456:Fluorescent Dyes; C485194:norrisolide