Indole Alkaloids of a Thai Medicinal Herb,Mitragyna speciosa,that has Opioid Agonistic Effect in Guinea-Pig Ileum

Planta Medica
2005.0

Abstract

Recently, we found that mitragynine, a major constituent of Mitragyna speciosa, has an opioid agonistic activity, but its weak potency could not explain the opium-like effect of this plant. In the present study, bioassay-guided fractionation of the crude extract of the leaves of M. speciosa was carried out to search for potent opioid agonists other than mitragynine. Opioid agonistic activities were evaluated using twitch contraction induced by electrical stimulation in guinea-pig ileum. The crude extract of M. speciosa inhibited the twitch contraction in a concentration-dependent manner. The inhibition was reversed by naloxone. The opioid effect was detected only in the crude base fraction, which was followed by the isolation of five indole alkaloids. Among these alkaloids, 7-hydroxymitragynine showed the most potent opioid effect on the electrically-stimulated contraction (pD (2) = 8.38 +/- 0.12). The potency, calculated using pD (2) values, was 30- and 17-fold higher than that of mitragynine and morphine, respectively. Antagonism of naloxone on concentration-response curves for 7-hydroxymitragynine confirmed its opioid effect. These results suggest that the opioid effect of M. speciosa is mostly based on the activity of 7-hydroxymitragynine.

Knowledge Graph

Similar Paper

Indole Alkaloids of a Thai Medicinal Herb,<i>Mitragyna speciosa,</i>that has Opioid Agonistic Effect in Guinea-Pig Ileum
Planta Medica 2005.0
Antinociceptive effect of 7-hydroxymitragynine in mice: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa
Life Sciences 2004.0
Studies on the Synthesis and Opioid Agonistic Activities of Mitragynine-Related Indole Alkaloids:  Discovery of Opioid Agonists Structurally Different from Other Opioid Ligands
Journal of Medicinal Chemistry 2002.0
A new indole alkaloid, 7-hydroxyspeciociliatine, from the fruits of Malaysian Mitragyna speciosa and its opioid agonistic activity
Journal of Natural Medicines 2006.0
A new indole alkaloid, 7-hydroxyspeciociliatine, from the fruits of Malaysian Mitragyna speciosa and its opioid agonistic activity
Journal of Natural Medicines 2006.0
Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa
Chemical and Pharmaceutical Bulletin 2004.0
Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceous Plant, Mitragyna speciosa
Chemical and Pharmaceutical Bulletin 2004.0
Chemical Studies on the Analgesic Indole Alkaloids from the Traditional Medicine (Mitragyna speciosa) Used for Opium Substitute
YAKUGAKU ZASSHI 2000.0
Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors
Journal of Natural Products 2021.0
Opioid receptor agonistic characteristics of mitragynine pseudoindoxyl in comparison with mitragynine derived from Thai medicinal plant Mitragyna speciosa
General Pharmacology: The Vascular System 1999.0