title: Flavonoid glucuronides with anti-leukaemic activity from Polygonum amphibium L.
abstract: BACKGROUND
  The chemical and pharmaceutical studies carried out on species from Polygonum L. genus showed biological activity both of the extracts and the components isolated from them. These results were the impulse to examine Polygonum amphibium L.
  
  
  OBJECTIVE
  The aim of this study was the isolation of active components from methanol extract and the determination of their cytotoxic effect on human leukaemic cell lines.
  
  
  METHODS
  Three flavonoid components from butanol soluble fractions of methanol extract by CC and PC preparative chromatography were isolated. Their structures were established on the basis of 1H, 13C and correlation (DEPT, H-H, COSY, HMQC, HMBC) NMR, UV and FAB-MS spectroscopic techniques. The evaluation of the anti-leukaemic activities of 1 and 2 against Jurkat and HL60 cell lines was carried out in vitro using annexin V fluorescence assay.
  
  
  RESULTS
  Two new flavonoid glucuronides, quercetin-3-O-beta-glucuronide (1) and quercetin-3-O-alpha-rhamnosyl-(1 --> 2)-beta-glucuronide (2), and kaempferol-3-O-alpha-rhamnosyl-(1 --> 2)-beta-glucuronide (3), were isolated from Polygonum amphibium L. It was demonstrated that the glucuronides of quercetin are able to induce apoptosis in the tested human leukaemic cells. These compounds penetrate through cytoplasm to the cellular nucleus of the cultured cells, and give intensive apoptotic responses in the stimulated leukaemic cells. The number of apoptotic cells increased with the concentration (1 nm to 10 microm) of 1 or 2 and periods of exposure (1-3 days).
  
  
  CONCLUSIONS
  Compounds 1 and 2 may be considered good candidates for leukaemia chemotherapeutic agents.
authors.affiliation: Department of Pharmaceutical Botany, Medical University, 1 Chodzki Str., 20-093 Lublin, Poland. h.smolarz@am.lublin.pl
authors.forename: H D
authors.initials: HD
authors.lastname: Smolarz
authors.forename: J
authors.initials: J
authors.lastname: Budzianowski
authors.forename: A
authors.initials: A
authors.lastname: Bogucka-Kocka
authors.forename: J
authors.initials: J
authors.lastname: Kocki
authors.forename: E
authors.initials: E
authors.lastname: Mendyk
mesh_terms: D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D005419:Flavonoids / Q000302:isolation & purification* / Q000494:pharmacology*; D020719:Glucuronides / Q000302:isolation & purification* / Q000494:pharmacology*; D018922:HL-60 Cells; D006801:Humans; D019169:Jurkat Cells; D044949:Kaempferols / Q000302:isolation & purification / Q000494:pharmacology; D007938:Leukemia / Q000188:drug therapy*; D000432:Methanol / Q000737:chemistry; D008517:Phytotherapy; D028502:Polygonum / Q000737:chemistry*; D011794:Quercetin / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D005419:Flavonoids; D020719:Glucuronides; D044949:Kaempferols; C443401:quercetin 3-O-glucuronide; D011794:Quercetin; D000432:Methanol