Inhibition of Trypsin and Chymotrypsin by Anti-Inflammatory Triterpenoids from Compositae Flowers

Abstract

Taraxastane, oleanane, ursane, lupane, taraxane, cycloartane, dammarane and tirucallane triterpenoids isolated from flowers of Compositae plants have been previously reported to exhibit anti-inflammatory effects and are variously competitive and non-competitive inhibitors of the serine proteases trypsin and chymotrypsin. The general features of those triterpenoids found to be protease inhibitors are having a hydroxy group and an appropriate side chain in the region of the molecule distal to the 3-hydroxy group. However, fatty acid esterification of the triterpenoid 3-hydroxy group can have a marked effect on inhibitor effectiveness. This suggests a possible means of rapid alteration of the plant defensive complement in vivo and of the bioactivity of these anti-inflammatory compounds.

Abbreviations

BAPNA:N _α-benzoyl-DL-arginine-p-nitroanilide

BYPNA:N-benzoyl-L-tyrosine-p-nitroanilide

PKA:cyclic AMP-dependent protein kinase

TLCK:N-α-p-tosyl-L-lysinylchloromethyl ketone (1-chloro-3-tosylamido-7-amino-L-2-heptanone)

TPCK:N-tosyl-L-phenylalanylchloromethyl ketone (L-(1-tosyl-amido-2-phenyl)ethylchloromethyl ketone).

Key words

Compositae - triterpenoids - protease inhibitors - trypsin - chymotrypsin

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