Inhibition of trypsin and chymotrypsin by anti-inflammatory triterpenoids from Compositae flowers.
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.
Rajic
A
A
Department of Biochemistry, La Trobe University, Bundoora, Victoria 3086, Australia.
Akihisa
T
T
Ukiya
M
M
Yasukawa
K
K
Sandeman
R M
RM
Chandler
D S
DS
Polya
G M
GM
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000494:pharmacology*; D019659:Asteraceae / Q000737:chemistry*; D002918:Chymotrypsin / Q000187:drug effects*; D010936:Plant Extracts / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology*; D014357:Trypsin / Q000187:drug effects*; D014361:Trypsin Inhibitors / Q000737:chemistry / Q000494:pharmacology*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D010936:Plant Extracts; D014315:Triterpenes; D014361:Trypsin Inhibitors; D002918:Chymotrypsin; D014357:Trypsin