Structure-Antinociceptive Activity Studies of Incarvillateine, a Monoterpene Alkaloid from Incarvillea sinensis
| Autor: | Fumio Hashimoto, Akihiko Yonezawa, Toyokichi Yoshizawa, Junei Kinjo, Yu-Ming Chi, Shinobu Sakurada, Toshihiro Nohara, Yumiko Nakasugi, Wen-Mei Yan, Motoyuki Nakamura |
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| Rok vydání: | 2001 |
| Předmět: |
Coumaric Acids
Stereochemistry Monoterpene Pain Pharmaceutical Science Pharmacognosy Analytical Chemistry Cyclobutane Ferulic acid Mice Structure-Activity Relationship chemistry.chemical_compound Alkaloids Formaldehyde Drug Discovery Incarvillateine Animals Pharmacology Analgesics Plants Medicinal Molecular Structure Phenylpropanoid Terpenes Alkaloid Organic Chemistry Incarvillea sinensis Disease Models Animal Complementary and alternative medicine chemistry Monoterpenes Molecular Medicine Azabicyclo Compounds |
| Zdroj: | Planta Medica. 67:114-117 |
| ISSN: | 1439-0221 0032-0943 |
| DOI: | 10.1055/s-2001-11512 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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