Quinovic acid glycosides from Mitragyna stipulosa--first examples of natural inhibitors of snake venom phosphodiesterase I.
Phytochemical investigations on the non-alkaloidal extracts of Mitragyna stipulosa bark has led to the isolation of a series of triterpenoids mainly consisting of quinovic acid ([structure: see text]) and its glycoside derivatives [structure: see text] and [structure: see text]. The other constituents isolated include alpha-amyrin, 3beta-acetyl ursolic acid and a mixture of oleanolic and ursolic acid and beta-sitosterol glucopyranoside. Their structures were identified by spectral and chemical studies and compounds [structure: see text] and [structure: see text] were, respectively, identified as quinovic acid 3-O-[beta-D-glucopyranoside] (quinovin glycoside C) and quinovic acid 3-O-[beta-D-quinovopyranoside]-27-O-[beta-D-glucopyranosyl] ester. Compounds [structure: see text] and [structure: see text] showed significant inhibitory activity against snake venom phosphodiesterase I.
Fatima
Naheed
N
HEJ Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi-75270, Pakistan.
Tapondjou
Leon Azefack
LA
Lontsi
David
D
Sondengam
B L
BL
Atta-Ur-Rahman
Choudhary
M Iqbal
MI
D002163:Cameroon; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D032065:Mitragyna / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000737:chemistry / Q000302:isolation & purification / Q000031:analogs & derivatives; D010726:Phosphodiesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D024301:Plant Bark / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012910:Snake Venoms / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D005960:Glucosides; D010726:Phosphodiesterase Inhibitors; D010936:Plant Extracts; D012910:Snake Venoms; D014315:Triterpenes; C472607:quinovic acid 3-O-quinovopyranoside-27-O-glucopyranosyl ester; C472606:quinovin glycoside C; D009828:Oleanolic Acid; C472605:quinovic acid; C036380:beta-amyrin