Cyclodextrin‐Mediated Enantiomeric Separation of Chiral Dihydrofuroflavones, a Class of Compounds with Promising Pharmacological Activity

References

• Hertog , M. G.L. , Hollman , P. C. and Katan , M. B. 1992 . Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands . J. Agric. Food. Chem. , 40 ( 12 ) : 2379 – 2383 .
   Web of Science ®Google Scholar
• Hertog , M. G.L. , Hollman , P. C. and van de Putte , P. 1993 . Content of potentially anticarcinogenic flavonoids of tea infusions, wines, and fruit juices . J. Agric. Food. Chem. , 41 ( 8 ) : 1242 – 1246 .
   Google Scholar
• Ngadjui , B. T. , Dongo , E. , Tamboue , H. , Fogue , K. and Abegaz , B. M. 1999 . Prenylated flavanones from the twigs of Dorstenia mannii . Phytochemistry , 50 ( 8 ) : 1401 – 1406 .
   Google Scholar
• Ngadjui , B. T. , Kouam , S. F. , Dongo , E. and Kapche , G. W.F. 2000 . Prenylated flavonoids from the aerial parts of Dorstenia mannii . Phytochemistry , 55 ( 8 ) : 915 – 919 .
   PubMedGoogle Scholar
• Li , W. K. , Xiao , P. G. and Zhang , R. Y. 1995 . Prenylated flavonoids from the aerial parts of Dorstenia mannii . Phytochemistry , 38 ( 3 ) : 807 – 808 .
   Google Scholar
• Maximo , P. , Lourenco , A. , Sonia Savluchinske , F. and Roserio , J. C. 2002 . Flavonoids from Ulex airensis and Ulex europaeus ssp europaeus . J. Nat. Prod. , 65 ( 2 ) : 175 – 178 .
   PubMedGoogle Scholar
• Lee , D. , Bhat , K. P.L. , Fong , H. H.S. , Farnsworth , N. R. , Pezzuto , J. M. and Kinghorn , A. D. 2001 . Aromatase inhibitors from Broussonetia papyrifera . J. Nat. Prod. , 64 ( 10 ) : 1286 – 1293 .
   PubMed Web of Science ®Google Scholar
• de‐Whalley , C. , Rankin , S. M. , Hoult , J. R.S. , Jessup , W. and Leake , D. S. 1990 . Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages . Biochem. Pharmacol. , 39 ( 11 ) : 1743 – 1750 .
   PubMedGoogle Scholar
• Johnson , M. K. and Loo , G. 2000 . Effects of epigallocatechin gallate and quercetin on oxidative damage to cellular DNA . Mutat. Res. , 459 ( 3 ) : 211 – 218 .
   PubMedGoogle Scholar
• Abalea , V. , Cillard , J. , Dubois , M. P. , Sergent , O. , Cillard , P. and Morel , I. 1999 . Repair of iron‐induced DNA oxidation by the flavonoid myricetin in primary rat hepatocyte cultures . Free Radic. Biol. Med. , 22 ( 11/12 ) : 1457 – 1466 .
   Google Scholar
• Frankel , E. N. , Kanner , J. , German , J. B. , Parks , E. and Kinsella , J. E. 1993 . Inhibition of oxidation of human low‐density lipoprotein by phenolic substances in red wine . Lancet , 341 ( 8843 ) : 454 – 457 .
   PubMed Web of Science ®Google Scholar
• Schleicher , R. L. , Lamartiniere , C. A. , Zheng , M. and Zhang , M. 1999 . The inhibitory effect of genistein on the growth and metastasis of a transplantable rat accessory sex gland carcinoma . Cancer Lett. , 136 ( 2 ) : 195 – 201 .
   PubMed Web of Science ®Google Scholar
• Pignatelli , P. , Pulcinelli , F. M. , Celestini , A. , Lenti , L. , Ghiselli , A. , Gazzaniga , P. P. and Violi , F. 2000 . The flavonoids quercetin and catechin synergistically inhibit platelet function by antagonizing the intracellular production of hydrogen peroxide . Am. J. Clin. Nutr. , 72 ( 5 ) : 1150 – 1155 .
   PubMed Web of Science ®Google Scholar
• McAnlis , G. T. , Mc Eneny , J. , Pearce , J. and Young , I. S. 1999 . Absorption and antioxidant effects of quercetin from onions, in man . Eur. J. Clin. Nutr. , 53 ( 2 ) : 92 – 96 .
   PubMedGoogle Scholar
• Boersma , B. J. , Barnes , S. , Kirk , M. , Wang , C. C. , Smith , M. , Kim , H. , Xu , J. , Patel , R. and Darley‐Usmar , V. M. 2001 . Soy isoflavonoids and cancer—metabolism at the target site . Mutat. Res. , 480–481 : 121 – 127 .
   PubMedGoogle Scholar
• O'Reilly , J. D. , Mallet , A. I. , McAnlis , G. T. , Young , I. S. , Halliwell , B. , Sanders , T. A.B. and Wiserman , H. 2001 . Consumption of flavonoids in onions and black tea: lack of effect on F2‐isoprostanes and autoantibodies to oxidized LDL in healthy humans . Am. J. Clin. Nutr. , 73 ( 6 ) : 1040 – 1044 .
   PubMed Web of Science ®Google Scholar
• Chopra , M. , Fitzsimons , P. E. , Strain , J. J. , Thurnham , D. I. and Howard , A. N. 2000 . Nonalcoholic red wine extract and quercetin inhibit LDL oxidation without affecting plasma antioxidant vitamin and carotenoid concentrations . Clin. Chem. , 46 : 1162 – 1170 .
   PubMed Web of Science ®Google Scholar
• Rozhkov , R. V. and Larock , R. C. 2004 . Synthesis of dihydrofuroflavonoids via palladium‐catalyzed annulation of 1,3‐dienes . Tetrahedron Lett. , 45 ( 5 ) : 911 – 914 .
   Google Scholar
• Syah , Y. M. , Achmad , S. A. , Ghisalberti , E. L. , Hakim , E. H. , Euis , H. , Makmur , L. and Mujahidin , D. 2001 . Artoindonesianins G‐I, three new isoprenylated flavones from Artocarpus lanceifolius . Fitoterapia , 72 ( 7 ) : 765 – 773 .
   PubMedGoogle Scholar
• Takashima , J. , Asano , S. and Ohsaki , A. 2000 . Structures and activities of constituents from Brazilian medicinal plant, Brosimum acutifolium . Tennen Yuki Kagobutsu Toronkai Koen Yoshishu , 42 : 487 – 492 . Chem. Abstr., 2135, 104986
   Google Scholar
• Machocho , A. K. , Lwande , W. , Jondiko , J. I. , Moreka , L. V.C. and Hassahali , A. 1995 . Three new flavonoids from the root of Tephrosia emoroides and their antifeedant activity against the larvae of the spotted stalk borer Chilo partellus Swinhoe . Int. J. Pharmacog. , 33 ( 3 ) : 222 – 227 .
   Google Scholar
• Simonyi , M. 1984 . On chiral drug action . Med. Res. Rev. , 4 ( 3 ) : 359 – 413 .
   PubMed Web of Science ®Google Scholar
• Ariens , E. J. 1986 . Stereochemistry: a source of problems in medicinal chemistry . Med. Res. Rev. , 6 ( 4 ) : 451 – 460 .
   PubMedGoogle Scholar
• FDA , U. 1992 . FDA's policy statement for the development of new stereoisomeric drugs . Chirality , 4 : 338 – 340 .
   PubMedGoogle Scholar
• Schumacher , D. D. , Mitchell , C. R. , Xiao , T. L. , Rozhkov , R. V. , Larock , R. C. and Armstrong , D. W. 2003 . Cyclodextrin‐based liquid chromatographic enantiomeric separation of chiral dihydrofurocoumarins, an emerging class of medicinal compounds . J. Chromatogr. A , 1011 : 37 – 47 .
   PubMed Web of Science ®Google Scholar
• Armstrong , D. W. and DeMond , W. 1984 . Cyclodextrin bonded phases for the liquid chromatographic separation of optical, geometrical, and structural isomers . J. Chromatogr. Sci. , 22 : 411 – 415 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Ward , T. J. , Armstrong , R. D. and Beesley , T. E. 1986 . Separation of drug stereoisomers by the formation of beta cyclodextrin inclusion complexes . Science , 232 ( 4754 ) : 1132 – 1135 .
   PubMed Web of Science ®Google Scholar
• Mitchell , C. R. , Desai , M. , McCulla , R. , Jenks , W. and Armstrong , D. W. 2002 . Use of native and derivatized cyclodextrin chiral stationary phases for the enantioseparation of aromatic and aliphatic sulfoxides by high performance liquid chromatography . Chromatographia , 56 : 127 – 135 .
   Web of Science ®Google Scholar
• Armstrong , D. W. and Zukowski , J. 1994 . Direct enantiomeric resolution of monoterpene hydrocarbons via reversed‐phase high‐performance liquid chromatography with an alpha‐cyclodextrin bonded stationary phase . J. Chromatogr. A , 666 : 445 – 448 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Ward , T. J. , Czech , A. , Czech , B. P. and Bartsch , R. A. 1985 . Synthesis, rapid resolution, and determination of absolute configuration of racemic 2,2′‐binaphthyldiyl crown ethers and analogues via beta cyclodextrin complexation . J. Org. Chem. , 50 : 5556 – 5559 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Chang , L. W. , Chang , S. C. , Wang , X. , Ibrahim , H. , Reid , G. R. and Beesley , T. E. 1997 . Comparison of the enantioselectivity of beta‐cyclodextrin vs. heptakis‐2,3‐dimethyl‐beta‐cyclodextrin LC stationary phases . J. Liq. Chromatogr. Relat. Technol. , 20 ( 20 ) : 3279 – 3295 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , DeMond , W. and Czech , B. P. 1985 . Separation of metallocene enantiomers by liquid chromatography: chiral recognition via cyclodextrin bonded phases . Anal. Chem. , 57 : 481 – 484 .
   Web of Science ®Google Scholar
• Armstrong , D. W. , Chen , S. , Chang , C. and Chang , S. 1992 . A new approach for the direct resolution of racemic beta adrenergic blocking agents by HPLC . J. Liq. Chromatogr. , 15 ( 3 ) : 545 – 556 .
   Web of Science ®Google Scholar
• Change , S. C. , Reid , G. L. III. , Chen , S. , Chang , C. C. and Armstrong , D. W. 1993 . Evaluation of a new polar‐organic high performance liquid chromatographic mobile phase for cyclodextrin bonded chiral stationary phases . TrAC, Trends Anal. Chem. , 12 ( 4 ) : 144 – 153 .
   Google Scholar
• Hinze , W. L. , Riehl , T. E. , Armstrong , D. W. , DeMond , W. , Alak , A. and Ward , T. J. 1985 . Liquid chromatographic separation of enantiomers using a chiral beta‐cyclodextrin bonded stationary phase and conventional aqueous–organic mobile phases . Anal. Chem. , 57 : 237 – 242 .
   Web of Science ®Google Scholar
• Stalcup , A. M. , Chang , S. C. , Armstrong , D. W. and Pitha , J. 1990 . (S)‐2‐hydroxypropyl‐beta‐cyclodextrin, a new chiral stationary phase for reversed‐phase liquid chromatography . J. Chromatogr. , 513 : 181 – 194 .
   PubMed Web of Science ®Google Scholar