Isolation and characterisation of procyanidins from Rumex obtusifolius

Phytochemical Analysis

Volumn 18, Issue 3, 2007, Pages 193-203

  Spencer, Paul ^a   Sivakumaran, Subathira ^a   Fraser, Karl ^a   Foo, L Yeap ^b   Lane, Geoffrey A ^a   Edwards, Patrick J B ^c   Meagher, Lucy P ^a  

^a AGRESEARCH GRASSLANDS   (New Zealand)

^b CALLAGHAN INNOVATION   (New Zealand)

^c MASSEY UNIVERSITY   (New Zealand)

Author keywords

13C NMR; ESI MS; Gallate; MALDI TOF MS; Rumex obtusifolius; Thiolysis

Indexed keywords

ACETONE; CHROMATOGRAPHY; COLLOIDS; DESORPTION; DEXTRAN; DIMERS; DRUG PRODUCTS; FLAVONOIDS; ION EXCHANGE; IONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

13C NMR; ELECTROSPRAY IONIZATION/MS; GALLATE; MATRIX-ASSISTED LASER DESORPTION/ IONIZATION TIME-OF-FLIGHT/MS; MATRIX-ASSISTED LASER DESORPTION/IONIZATION TIME-OF FLIGHT; POLYMER FRACTIONS; PROCYANIDINS; RUMEX OBTUSIFOLIUS; THIOLYSIS; TIME-OF-FLIGHT MS;

ELECTROSPRAY IONIZATION;

3,3' O DIGALLATE; ACETONE; ACID; BENZOPYRAN DERIVATIVE; CATECHIN; EPICATECHIN; EPICATECHIN GALLATE; FLAVAN 3 OL; FLAVAN DERIVATIVE; GALLIC ACID DERIVATIVE; OLIGOMER; PLANT EXTRACT; POLYAMIDE; POLYGALLOYL DERIVATIVE; POLYMER; PROCYANIDIN DERIVATIVE; RUMEX OBTUSIFOLIUS EXTRACT; SEPHADEX; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CONTROLLED STUDY; DEGRADATION KINETICS; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION PROCEDURE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; PHYTOCHEMISTRY; PLANT LEAF; POLYMERIZATION; RUMEX; RUMEX OBTUSIFOLIUS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

RUMEX OBTUSIFOLIUS;

EID: 34248597143     PISSN: 09580344     EISSN: 10991565     Source Type: Journal    
DOI: 10.1002/pca.967     Document Type: Article

References (48)

1. Abe I, Seki T, Noguchi H, Kashiwada Y. 2000. Galloyl esters from rhubarb are potent inhibitors of squalene epoxidase, a key enzyme in cholesterol biosynthesis. Planta Medica 66: 753-756.
2. Aerts RJ, Barry TN, McNabb WC. 1999. Polyphenols and agriculture: Beneficial effects of proanthocyanidins in forages. Agric Ecosystems Environ 75: 1-12.
3. Balde AM, Bruyne, TD, Pieters L, Kolodziej, H, Bergehe DV, Claeys M, Vlietinck A. 1995. Oligomeric proanthocyanidins possessing a doubly linked structure from Pavetta owariensis. Phytochemistry 38: 719-723.
4. Baiza F, Abramowski Z, Towers GHN, Wiriyachitra P. 1989. Identification of proanthocyanidin polymers as the piscicidal constituents of Mammea siamensis, Polygonurn stagninum and Diospyros diepenhorstii. Phytochemistry 28: 1827-1830.
5. Behrens A, Maie N, Knicker H, Kögel-Knabner I. 2003. MALDI-TOF mass spectrometry and PSD fragmentation as a means for the analysis of condensed tannins in plant leaves and needles. Phytochemistry 62: 1159-1170.
6. 13C NMR assignments of some green tea polyphenols. Magn Reson Chem 34: 887-890.
7. Dear BS, Moore GA, Hughes SJ. 2003. Adaptation and potential contribution of temperate perennial legumes to the southern Australian wheatbelt: A review. Austr J Exp Agric 43: 1-18.
8. Demirezer LÖ, Kuruüzüm A. 1997a. A comparative chemotaxonomic study on eleven Rumex species growing in Turkey. FABAD J Pharm Sci 22: 153-158.
9. Demirezer LÖ, Kuruüzüm A. 1997b. Rapid and simple biological activity screening of some Rumex species; Evaluation of bioguided fractions of R. scutatus and pure compounds. Z Naturforsch 52: 665-669.
10. Demirezer LÖ, Kuruüzum-Uz A, Bergere I, Schiewe H-J, Zeeck A. 2001. The structures of antioxidant and cytotoxic agents from natural source: Anthraquinones and tannins from roots of Rumex patientia. Phytochemistry 58: 1213-1217.
11. 13C NMR spectroscopy and determination of antifungal activities. J Agric Food Chem 42: 1704-1708.
12. Fairburn JW, Muhtadi FJ. 1972. The biosynthesis and metabolism of anthraquinones in Rumex obtusifolius. Phytochemistry 11: 215-219.
13. Foo LY, Newman R, Waghorn G, McNabb WC, Ulyatt MJ. 1996. Proanthocyanidins from Lotus corniculatus. Phytochemistry 41: 617-624.
14. Foo LY, Lu Y, Howell AB, Vorsa N. 2000a. A-type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli. J Nat Prod 63: 1225-1228.
15. Foo LY, Lu Y, Howell AB, Vorsa N. 2000b. The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro. Phytochemistry 54: 173-181.
16. Fulcrand H, Guyot S, Le Roux E, Remy S, Souquet JM, Doco T, Cheynier V. 1999. Electrospray contribution to structural analysis of condensed tannin oligomers and polymers. Plant Polyphenols 2: Chemistry, Biology, Pharmacology, Ecology. Kluwer Academic/ Plenum: New York; 223-244.
17. Gu L, Kelm M, Hammerstone JF, Beecher G, Cunningham D, Vannozzi S, Prior RL. 2002. Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimised normal-phase HPLC-MS fluorescent detection method. J Agric Food Chem 50: 4852-4860.
18. Guyot S, Marnet N, Laraba D, Sanoner P, Drilleau JF. 1998. Reversed-Phase HPLC followed by thiolysis for quantitative estimation and characterisation of the four main classes of phenolic compounds in different tissue zones of a French cider apple variety (Malus domestica Var. Kermerrien). J Agric Food Chem 46: 1698-1705.
19. Guyot S, Marnet N, Drilleau JF. 2001. Thiolysis-HPLC characterisation of apple procyanidins covering a large range of polymerisation states. J Agric Food Chem 49: 14-20.
20. Hartisch C, Kolodziej H. 1996. Galloylhamameloses and proanthocyanidins from Hamamelis Virginincc Phytochemistry 42: 191-198.
21. Hasan A, Ahmed I, Jay M, Voirin B. 1995. Flavonoid glycosides and an anthraquinone from Rumex chalepensis. Phytochemistry 39: 1211-1213.
22. Hemingway RW, Karchesy JJ, McGraw GW, Wielesek RA. 1983. Heterogeneity of interfiavanoid bond location in loblolly pine bark procyanidins. Phytochemistry 22: 275-281.
23. Kasai T, Okuda M, Sakamura S. 1981. 6-O-malonyl-β-methyl-D-glucopyranoside from roots of Rumex obtusifolius. Phytochemistry 20: 1131-1132.
24. Kasai T, Okuda M, Sano H, Mochizuki H, Sato H, Sakamura S. 1982. Biological activity of the constituents in roots of Ezo-no-gishigishi (Rumex obtusifolius). Agric Biol Chem 46: 2809-2813.
25. Kennedy JA, Matthews MA, Waterhouse AL. 2000. Changes in grape seed polyphenols during fruit ripening. Phytochemistry 55: 77-85.
26. Krueger CG, Carter DN, Treichel PM, Folts J, Reed JD. 2000. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of polygalloyl polyfiavan-3-ols in grape seed extract. J Agric Food Chern 48: 1663-1667.
27. Krueger CG, Vestling MM, Reed JD. 2003. Matrix-assisted laser desorption/ ionisation time-of flight mass spectrometry of heteropolyflavan-3-ols and glucosylated heteropolyflavans in sorghum [Sorghum bicolor (L.) Moench]. J Agric Food Chem 51: 538-543.
28. Kuruüzüm A, Demirezer LO, Bergere I, Zeeck A. 2001. Two new chlorinated naphthalene glycosides from Rumex patientia. J Nat Prod 64: 688-690.
29. Labarbe B, Cheynier V, Brossaud F, Souquet JM, Moutounet M. 1999. Quantitative fractionation of grape proanthocyanidins according to their degree of polymerisation. J Agric Food Chem 47: 2719-2723.
30. Matthews S, Mila I, Scalbert A, Donnelly DMX. 1997. Extractable and non-extractable proanthocyanidins in barks. Phytochemistry 45: 405-410
31. McNabb WC, Peters JS, Foo LY, Waghorn GC, Jackson FS. 1998. Effect of condensed tannins prepared from several forages on the in vitro precipitation of ribulose-1,5-bisphosphate carboxylase (Rubisco) protein and its digestion by trypsin (EC 2.4.21.4) and chymotrypsin (EC 2.4.21.1). J Sci Food Agric 77: 201-212.
32. Mill BR, Barry TN, Attwood GT, McNabb WC. 2003. The effect of condensed tannins on the nutrition and health of ruminants fed fresh temperate forages: a review. Animal Feed Sci Technol 106: 3-19.
33. Molan AL, Waghorn GC, McNabb WC. 2002. The impact of condensed tannins on egg hatching and larval development of Trichostrongylus colubriformis in vitro. Vet Rec 150: 65-69.
34. 163C NMR studies of proanthocyanidin polymers (condensed tannins). Magn Reson Chem 25: 118-124.
35. Nonaka GI, Nishioka I, Nagasawa T, Oura H. 1981. Tannins and related compounds. I. Rhubarb (1). Chem Pharm Bull 29: 2862-2870.
36. Nonaka GI, Muta M, Nishioka I. 1983. Myricatin, a galloyl flavanonol sulfate and prodelphinidin gallates from Myrica rubra. Phytochemistry 22: 237-241.
37. Ohara S, Yanagi K. 1995. Polyphenols in Salix species I. Polyphenols from the bark of Salix rorida Lackschewitz. Mokuzai Gakkaishi 41: 406-413.
38. Perret C, Pezet R, Tabacchi R. 2003. Fractionation of grape tannins and analysis by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. Phytochem Anal 14: 202-208.
39. Prieur C, Rigaud J, Cheynier V, Moutounet M. 1994. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36: 781-784.
40. Reed JD, Krueger CG, Vestling MM. 2005. MALDI-TOF mass spectrometry of oligomeric food polyphenols. Phytochemistry 66: 2248-2263.
41. Ricardo da Silva JM, Rigaud V, Cheynier A, Cheminat A, Moutounet M. 1991. Procyanidin dimers and trimers from grape seeds. Phytochemistry 30: 1259-1264.
42. Rivero-Cruz I, Acevedo L, Guerrero JA, Martínez S, Bye R, Pereda MR, Franzblau S, Timmermann BN, Mata R. 2005. Antimycobacterial agents from selected Mexican medicinal plants. J Pharm Pharmac 57: 1117-1126.
43. Shoji T, Mutsuga M, Nakamura T, Kanda T, Akiyama H, Goda Y. 2003. Isolation and structural elucidation of some procyanidins from apple by low-temperature nuclear magnetic resonance. J Agric Food Chem 51: 3806-3813.
44. Sivakumaran S, Meagher LP, Foo LY, Lane GA, Fraser K, Rumball W. 2004. Floral procyanidins of the forage legume red clover (Trifolium pratense L.). J Agric Food Chem 52: 1581-1585.
45. Sun D, Wong H, Foo AY. 1987. Proanthocyanidin dimers and polymers from Quercus dentata Phytochemistry 26: 1825-1829.
46. Waghorn GC, Jones WT. 1989. Bloat in cattle: potential of dock (Rumex obtusifolius) as an antibloat agent for cattle. NZ J Agric Res 32: 227-235.
47. Wilkins RJ, Jones R. 2000. Alternative home-grown protein sources for ruminants in the United Kingdom. Animal Feed Sci Technol 85: 23-32.
48. Wilkinson S. 1958. α-Picoline from Rumex obtusifolius L. Nature 181: 636-637.