Planta Med 2001; 67(7): 599-604
DOI: 10.1055/s-2001-17350
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

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

Antonio Rajic1,4 , Toshihiro Akihisa2 , Motohiko Ukiya2 , Ken Yasukawa3 , R. Mark Sandeman4 , David S. Chandler5 , Gideon M. Polya1,*
  • 1 Department of Biochemistry, La Trobe University, Victoria, 3086 Australia
  • 2 College of Science and Technology, Nihon University, Tokyo, Japan
  • 3 College of Pharmacy, Nihon University, Chiba, Japan
  • 4 Department of Agricultural Sciences, La Trobe University, Victoria, Australia
  • 5 Nufarm Ltd., Victoria, Australia
Further Information

Publication History

September 15; 2000

December 15, 2000

Publication Date:
24 September 2001 (online)

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).

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Dr. G. M. Polya

Department of Biochemistry

La Trobe University

Bundoora, Victoria 3086

Australia

Email: g.polya@latrobe.edu.au

Fax: +61-3-9479 2467