Regiospecific 4′-O-β-glucosidation of isoflavones

Lewis, Philip T.; Wähälä, Kristiina

doi:10.1016/s0040-4039(98)02124-8

Cited by 14 publications

(7 citation statements)

References 15 publications

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“…12 However, the spectrum of 4b substantially differed from the spectrum of the synthetic 4'-O-glucoside. 18 In the latter case, the diagnostic signals of the remaining phenolic OH (9.60 ppm), 3',5'-H (6.83), 6-H (6.47), and 8-H (6.72) confirmed a 7-O-substitution rather than the 4'-O-glucosylation. Therefore, the ribosides reported in the present work are the first genistein 4'-O-glycosides obtained by chemical synthesis.…”

mentioning

confidence: 84%

“…17 On the other hand, direct glycosylation of 1 with tetra-Oacetyl-a-bromoglucose in the presence of potassium t-butoxide and catalytic amounts of 18-crown-6 ether reportedly gave genistein 4'-O-b-glucoside (sophoricoside) in a stereo-and regioselective manner (41% of yield). 18 Thus, the methods presented so far are limited to base catalyzed glycosylation.…”

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confidence: 99%

“…The structure of products was confirmed by the 1 H and 13 C NMR spectra (Tables 1 and 2), and their comparison with the spectrum of unsubstituted genistein (1), as well as with literature data for the genistein 7-O-glucoside 12,17 and 4'-O-glucoside. 12,18 For a complete assignment of proton and carbon signals, the following two dimensional techniques were used: heteronuclear multiple bond correlation (HM-BC), heteronuclear single quantum correlation (HSQC) and NOESY spectra. In the 1 H NMR spectra, the signal of 7-OH group and lack of 4'-OH clearly indicated the site of glycosylation.…”

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confidence: 99%

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A Regioselective Synthesis of Genistein 4′-O-Ribofuranosides

Boryski¹,

Grynkiewicz²

2001

Synthesis

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A direct glycosylation reaction of biologically significant isoflavone, genistein (1) with 1,2,3,5-tetra-O-acetyl-b-D-ribofuranose (2) in the presence of tin tetrachloride gave a satisfactory yield of a mixture of 4'-O-a-(3a) and 4'-O-b-D-ribofuranosides (3b), in the ratio 1:2 respectively. After deacetylation, anomers 4a and 4b were separated by chromatographic means. The results are compared with ribosylation of phenol and the regio-and stereoselectivity of genistein glycosylation are discussed.

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confidence: 84%

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confidence: 99%

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A Regioselective Synthesis of Genistein 4′-O-Ribofuranosides

Boryski¹,

Grynkiewicz²

2001

Synthesis

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“…S8, ESIw) which results in the formation of a phenolate moiety by the abstraction of a proton from the -OH group. 32 The employment of NaBH 4 in the formation of phenolate of isoflavones (1d-1h) may prevent the transformation of Co(II)Pc into Co(I)Pc species and thereby inhibit the reduction of 1d-1h. Further, the interaction of the electron rich phenolate moiety with electron deficient boron species could generate an unusual boron-oxygen complex 33 (Scheme 5, Path B) which would make the system inactive by preventing the interaction of NaBH 4 with Co(II)Pc.…”

Section: Methodsmentioning

confidence: 99%

Formation of hydridocobalt(iii) phthalocyanine by reaction of cobalt(ii) phthalocyanines with sodium borohydride and its reactions with antioxidant isoflavones

et al. 2011

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“…In the next publication, the first stereospecific synthesis of isoflavone 4’- O -β-glucosides from unprotected isoflavone aglycones was proposed [ 141 ]. The procedure, involving a solid/liquid crown ether catalyzed phase transfer method has been used for the synthesis of daidzin ( 29 ), genistin ( 30) (Scheme 8 ).…”

Section: Chemical Glycosylation Of Isoflavonesmentioning

confidence: 99%

Isoflavones, their Glycosides and Glycoconjugates. Synthesis and Biological Activity

Szeja

Grynkiewicz

Rusin

2016

COC

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Glycosylation of small biologically active molecules, either of natural or synthetic origin, has a profound impact on their solubility, stability, and bioactivity, making glycoconjugates attractive compounds as therapeutic agents or nutraceuticals. A large proportion of secondary metabolites, including flavonoids, occur in plants as glycosides, which adds to the molecular diversity that is much valued in medicinal chemistry studies. The subsequent growing market demand for glycosidic natural products has fueled the development of various chemical and biotechnological methods of glycosides preparation. The review gives an extensive overview of the processes of the synthesis of isoflavones and discusses recently developed major routes towards isoflavone-sugar formation processes. Special attention is given to the derivatives of genistein, the main isoflavone recognized as a useful lead in several therapeutic categories, with particular focus on anticancer drug design. The utility of chemical glycosylations as well as glycoconjugates preparation is discussed in some theoretical as well as practical aspects. Since novel approaches to chemical glycosylations and glycoconjugations are abundant and many of them proved suitable for derivatization of polyphenols a new body of evidence has emerged, indicating that sugar moiety can play a much more significant role, when attached to a pharmacophore, then being a mere “solubilizer”. In many cases, it has been demonstrated that semisynthetic glycoconjugates are much more potent cytostatic and cytotoxic agents than reference isoflavones. Moreover, the newly designed glycosides or glycoside mimics can act through different mechanisms than the parent active molecule.

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Regiospecific 4′-O-β-glucosidation of isoflavones

Cited by 14 publications

References 15 publications

A Regioselective Synthesis of Genistein 4′-O-Ribofuranosides

A Regioselective Synthesis of Genistein 4′-O-Ribofuranosides

Formation of hydridocobalt(iii) phthalocyanine by reaction of cobalt(ii) phthalocyanines with sodium borohydride and its reactions with antioxidant isoflavones

Isoflavones, their Glycosides and Glycoconjugates. Synthesis and Biological Activity

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