L-canaline: a potent antimetabolite and anti-cancer agent from leguminous plants.
L-Canaline, the L-2-amino-4-(aminooxy)butyric acid structural analog of L-ornithine' is a powerful antimetabolite stored in many leguminous plants. This nonprotein amino acid reacts vigorously with the pyridoxal phosphate moiety of vitamin B6-containing enzymes to form a covalently-bound oxime that inactivates, often irreversibly, the enzyme. Canaline is not only capable of inhibiting ornithine-dependent enzymic activity, but it also can function as a lysine antagonist. Recently, this natural product was found to possess significant antineoplastic in vitro activity against human pancreatic cancer cells.
Rosenthal
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Laboratory of Biochemical Ecology, University of Kentucky, Lexington 40506, USA. garose@ukcc.uky.edu
D000613:Aminobutyrates / Q000378:metabolism / Q000494:pharmacology*; D000818:Animals; D000963:Antimetabolites / Q000378:metabolism / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000378:metabolism / Q000494:pharmacology*; D004032:Diet; D004354:Drug Screening Assays, Antitumor; D004791:Enzyme Inhibitors / Q000378:metabolism / Q000494:pharmacology*; D007887:Fabaceae / Q000737:chemistry; D006801:Humans; D010091:Oximes / Q000378:metabolism; D010946:Plants, Medicinal; D011732:Pyridoxal Phosphate / Q000378:metabolism; D014407:Tumor Cells, Cultured
D000613:Aminobutyrates; D000963:Antimetabolites; D000972:Antineoplastic Agents, Phytogenic; D004791:Enzyme Inhibitors; D010091:Oximes; C001926:canaline; D011732:Pyridoxal Phosphate