Activity of lupane triterpenoids from Maytenus species as inhibitors of nitric oxide and prostaglandin E2.
In the present study, we report that three new lupane triterpenes (1-3), in addition to 16 known ones (4-19), were isolated from the root bark of Maytenus cuzcoina and the leaves of Maytenus chiapensis. Their structures were elucidated by spectral analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC, and HMBC). The natural compounds and derivatives 6a, 6b, 9a, and 9b have been tested for potential anti-inflammatory activity, and several compounds including 3-epicalenduladiol (2), 11alpha-hydroxy-glochidone (3), rigidenol (6), acetoxy-rigidenol (6a), 11alpha-acetoxy-30-chloro-3-oxo-lup-20(29)-ene (6b), betulin (9), 28-acetoxy-betulin (9a), epibetulin (12), epibetulinic acid (13), and betulonic acid (16) exhibited potent inhibitory effects on NO and prostaglandin E(2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin. The structure-activity relationship is discussed in detail.
Reyes
Carolina P
CP
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna and Instituto Canario de Investigación del Cáncer, Tenerife, Canary Islands, Spain.
Núñez
Marvin J
MJ
Jiménez
Ignacio A
IA
Busserolles
Jérôme
J
Alcaraz
María J
MJ
Bazzocchi
Isabel L
IL
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D001424:Bacterial Infections / Q000139:chemically induced; D015232:Dinoprostone / Q000037:antagonists & inhibitors* / Q000378:metabolism; D004731:Endotoxins; D008264:Macrophages / Q000382:microbiology; D029755:Maytenus / Q000737:chemistry*; D051379:Mice; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000378:metabolism; D018515:Plant Leaves / Q000737:chemistry; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D053978:Pentacyclic Triterpenes
D000972:Antineoplastic Agents, Phytogenic; D015232:Dinoprostone; D004731:Endotoxins; D009569:Nitric Oxide; D014315:Triterpenes; C480546:lupane; D053978:Pentacyclic Triterpenes