Genistein complexes with amines: structure and properties

Mazurek, Aleksander P.; Kozerski, Lech; Sadlej, Joanna; Kawę, Robert; Bednarek, Elżbieta; Sitkowski, Jerzy; Dobrowolski, Jan Cz.; Maurin, Jan K.; Biniecki, Krzysztof; Witowska, Janina; Fiedor, Piotr; Pachecka, J

doi:10.1039/a708956b

Cited by 30 publications

(28 citation statements)

References 19 publications

(21 reference statements)

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“…42 Moreover, genistein also reacts with amine by transferring the proton of H a O a hydroxyl group to amine in the crystal packing. 43 All these are in line with our study that H a O a forms the strongest hydrogen bond with the hydrogen bond acceptor. Since genistein has several docking sites for the proton of MeOH and it also could act as a hydrogen bond donor, the systems containing multiple MeOH molecules (MeOH : genistein ¼ 2 : 1, 3 : 1, and 6 : 1) were further studied.…”

Section: Conformational Analysissupporting

confidence: 88%

Molecular interaction between MeOH and genistein during soy extraction

et al. 2019

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Section: Conformational Analysissupporting

confidence: 88%

Molecular interaction between MeOH and genistein during soy extraction

et al. 2019

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“…The calculated distance for the H-bond involving the (C 5 OH) moiety in GEN is 166 pm (Fig. 1), close to the experimental value reported for the genistein-morpholine complex (GMC, 165 pm) in the condensed phase (Table 2) [45]. Moreover, in GEN the C 5 O and C 4 O 12 distances are predicted to be 133.6 and 125.2 pm, respectively, very close to the crystallographic values of 135.9 and 126.3 pm obtained for GMC (Table 2) Table 2), once again reflecting the good quality of the structures presently obtained by DFT theoretical methods.…”

Section: Conformational Analysissupporting

confidence: 85%

“…The theoretical DFT geometries obtained for the isolated molecules under study were compared to the X-ray crystallographic data found in the literature for similar systems [45,46], a very good agreement having been found both for bond distances and angles. The calculated distance for the H-bond involving the (C 5 OH) moiety in GEN is 166 pm (Fig.…”

Section: Conformational Analysismentioning

confidence: 68%

A conformational study of hydroxylated isoflavones by vibrational spectroscopy coupled with DFT calculations

Machado¹,

Carvalho²,

Otero³

et al. 2013

Vibrational Spectroscopy

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This article appeared in a journal published by Elsevier. The attached copy is furnished to the author for internal non-commercial research and education use, including for instruction at the authors institution and sharing with colleagues. Other uses, including reproduction and distribution, or selling or licensing copies, or posting to personal, institutional or third party websites are prohibited. In most cases authors are permitted to post their version of the article (e.g. in Word or Tex form) to their personal website or institutional repository. Authors requiring further information regarding Elsevier's archiving and manuscript policies are

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“…The somewhat lower values for II, by virtue of the possibility of a longer side chain may show a less flapping tendency(higher potential barrier to free rotation) than I. These dihedral angles are nevertheless, in the range observed in the previously determined isoflavone structures from 32° to 75° (LAKSHMI, KUMAR, SENTHILSELVAN & SUBRAMANIAN, 1996;SHOJA , 1992 a,b;BRETON, PRECIGOUX, COURSEILLE & HOSPITAL, 1975;KANEDA, IITAKA & SHIBATA, 1973;ACHARYA, PURANIK, TAVALE & ROW, 1986;BÖCSKEL, SIMON, VARGA & HERMECZ, 1996;MAZUREK et al, 1998). Despite the biochemical activity of flavones and isoflavones few are listed in the Cambridge data file.…”

Section: Resultsmentioning

confidence: 94%

The Crystal Structures of O,O-Dimethylalpinumisoflavone and 5-O-Methyl-4'-O-(3-methyl-but-2-en-1-yl)alpinumisoflavone

Kingsford-Adaboh

Osei-Fosu

Asomaning

et al. 2001

Cryst. Res. Technol.

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The petrol extract of the rootbark of Milletia Thonningii obtained by column chromatography afforded sixteen different crystalline samples to be isolated. The crystal structures of two of these compounds, O,O‐Dimethylalpinumisoflavone (I) and 5‐O‐Methyl‐4'‐O‐(3‐methyl‐but‐2‐en‐1‐yl)alpinumisoflavone (II) are being reported here. (II) has two independent molecules in the asymmetric unit and differs from (I) in a longer side chain attached to C(15) of the phenyl ring. The structural features of the three molecules in the title compounds are reported and compared. The derivatives, being subject of this article are the first reported crystal structures where the isoflavone fragment is fused to a further six membered ring that results in a tricyclic ring system. The benzopyrone fragments are planar. The dihedral angles between the benzopyrone fragment and the phenyl ring being 55.38(6)° for (I) and 44.75(15)° /44.64(15)° for the respective independent molecules of (II) are within the range of values observed for similar structures.

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Genistein complexes with amines: structure and properties

Cited by 30 publications

References 19 publications

Molecular interaction between MeOH and genistein during soy extraction

Molecular interaction between MeOH and genistein during soy extraction

A conformational study of hydroxylated isoflavones by vibrational spectroscopy coupled with DFT calculations

The Crystal Structures of O,O-Dimethylalpinumisoflavone and 5-O-Methyl-4'-O-(3-methyl-but-2-en-1-yl)alpinumisoflavone

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