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Structure-antinociceptive activity studies of incarvillateine, a monoterpene alkaloid from Incarvillea sinensis.

Abstract
Incarvillateine (1), a new monoterpene alkaloid carrying a characteristic cyclobutane ring, has been found to show significant antinociceptive activity in a formalin-induced pain model in mice. To investigate the correlation between its structure and antinociceptive activity, and especially to study whether a cyclobutane ring is necessary or not for expression of activity, we evaluated the antinociceptive activity of two constructive units of incarvillateine, such as a monoterpene unit (incarvilline, 3) and a phenylpropanoid unit (ferulic acid, 2) in the formalin test, and compared activity of the units with that of incarvillateine. Furthermore, in order to obtain more information about the structure-activity relationships, monoterpene alkaloid derivatives, such as incarvine C (5, a precursor of incarvillateine), incarvine A (4, an ester compound comprised of two monoterpene alkaloids and a monoterpene) and 3,3'-demethoxy-4,4'-dehydroxyincarvillateine (6, a synthetic new compound), were examined. The antinociceptive effect of 3,3'-demethoxy-4,4'-dehydroxyincarvillateine was equal to that of incarvillateine. Meanwhile, the other compounds exhibited no or weak activity. These results suggested that the cyclobutane moiety of incarvillateine plays an important role in expression of antinociceptive action.
AuthorsM Nakamura, Y M Chi, W M Yan, A Yonezawa, Y Nakasugi, T Yoshizawa, F Hashimoto, J Kinjo, T Nohara, S Sakurada
JournalPlanta medica (Planta Med) Vol. 67 Issue 2 Pg. 114-7 (Mar 2001) ISSN: 0032-0943 [Print] Germany
PMID11301854 (Publication Type: Comparative Study, Journal Article)
Chemical References
  • 3,3'-demethoxy-4,4'-dehydroxyincarvillateine
  • Alkaloids
  • Analgesics
  • Azabicyclo Compounds
  • Coumaric Acids
  • Monoterpenes
  • Terpenes
  • incarvillateine
  • incarvine C
  • Formaldehyde
Topics
  • Alkaloids (isolation & purification, pharmacology)
  • Analgesics (isolation & purification, pharmacology)
  • Animals
  • Azabicyclo Compounds (isolation & purification, pharmacology)
  • Coumaric Acids (isolation & purification, pharmacology)
  • Disease Models, Animal
  • Formaldehyde (toxicity)
  • Mice
  • Molecular Structure
  • Monoterpenes
  • Pain (chemically induced)
  • Plants, Medicinal (chemistry)
  • Structure-Activity Relationship
  • Terpenes (isolation & purification, pharmacology)

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