Chemical mechanism of inactivation of bee venom phospholipase A2 by the marine natural products manoalide, luffariellolide, and scalaradial

BCM Potts, DJ Faulkner, MS De Carvalho…

Index: Potts, Barbara C. M.; Faulkner, D. John; De Carvalho, Marianne S.; Jacobs, Robert S. Journal of the American Chemical Society, 1992 , vol. 114, # 13 p. 5093 - 5100

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Citation Number: 99

Abstract

Abstract: Inhibition of bee venom phospholipase A,(PLA2) by manoalide (1) and luffariellolide (2) involves the initial formation of a Schiff base (imine) between a lysine residue on PLA2 and an aldehyde group on each of the drugs. Model reactions employing a primary amine in place of the lysine residue were studied by'H NMR spectroscopy. Amines reacted at the y-hydroxybutenolide ring of 2 to produce y-(alky1amino) butenolides 6a, b, ...