6''-O-Malonylgenistin - CAS 51011-05-3
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
6''-O-Malonylgenistin
Catalog Number:
51011-05-3
Synonyms:
5-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl 6-O-(carboxyacetyl)-β-D-glucopyranoside;
CAS Number:
51011-05-3
Description:
6''-O-Malonylgenistin (Malonylgenistin) is an isoflavone derivative.
Molecular Weight:
518.42
Molecular Formula:
C24H22O13
Quantity:
Milligrams-Grams
Quality Standard:
Enterprise Standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
c1cc(ccc1c2coc3c(ccc(c3c2=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC(=O)O)O)O)O)O
InChI:
1S/C24H22O13/c25-11-3-1-10(2-4-11)12-8-35-23-14(6-5-13(26)18(23)19(12)30)36-24-22(33)21(32)20(31)15(37-24)9-34-17(29)7-16(27)28/h1-6,8,15,20-22,24-26,31-33H,7,9H2,(H,27,28)/t15-,20-,21+,22-,24-/m1/s1
InChIKey:
PELWZARZGNQRCH-ZRYVYJFNSA-N
Targets:
Others
Chemical Structure
CAS 51011-05-3 6''-O-Malonylgenistin

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Reference Reading


1.Isoflavone content and its potential contribution to the antihypertensive activity in soybean Angiotensin I converting enzyme inhibitory peptides.
Wu J1, Muir AD. J Agric Food Chem. 2008 Nov 12;56(21):9899-904. doi: 10.1021/jf801181a. Epub 2008 Oct 15.
A soybean angiotensin I converting enzyme (ACE) inhibitory peptide fraction was reported to have antihypertensive activity in a rat study. The purpose of the present study was to examine if the presence of isoflavones in the soybean ACE inhibitory peptide fraction may contribute to the blood-pressure-lowering property. The isoflavone concentration in soybean samples was analyzed on a C 18 reverse-phase column using a two-step gradient solvent system. Producing soybean hydrolysate led to a nearly 40% loss of isoflavones compared with the original soybean flour, but the isoflavone composition did not change and the dominant isoflavone chemicals remained as 6''-O-malonylgenistin and 6''-O-malonyldaidzin. Ion exchange chromatography affected significantly both the content and the composition of the isoflavones. The dominant isoflavones in the ion-exchanged fraction were aglycones and nonacylated isoflavones, accounting for 95.8% of the total amount of 987.
2.Multi-response optimisation of the extraction solvent system for phenolics and antioxidant activities from fermented soy flour using a simplex-centroid design.
Handa CL1, de Lima FS2, Guelfi MF3, Georgetti SR4, Ida EI5. Food Chem. 2016 Apr 15;197(Pt A):175-84. doi: 10.1016/j.foodchem.2015.10.124. Epub 2015 Nov 11.
A simplex-centroid design comprising three solvents (water, ethanol and methanol) was used to optimise the extraction mixture for phenolics and antioxidant activities from defatted soy flour fermented with Monascus purpureus or Aspergillus oryzae. Total phenolics were more efficiently extracted using only water for both samples. The highest antioxidant activities by the DPPH and ABTS methods were obtained using extraction mixtures containing at least 75 wt% water. Specific water:ethanol:methanol ratios promoted the joint optimisation of the total phenolic and isoflavone contents as well as antioxidant activities: 0.5:0.375:0.125 (wt/wt/wt) and 0.5:0.3:0.2 (wt/wt/wt) from defatted soy flour fermented with M. purpureus or A. oryzae, respectively. However, a water:ethanol ratio of 0.5:0.5 (wt/wt) was deemed optimal because it is comprised of green solvents and yielded results that were greater than 90% of the multi-response maximum values. Both the solvents and the sample matrix strongly influenced the extractability of total phenolics and isoflavones.
3.Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim.
Fedoreyev SA1, Bulgakov VP, Grishchenko OV, Veselova MV, Krivoschekova OE, Kulesh NI, Denisenko VA, Tchernoded GK, Zhuravlev YN. J Agric Food Chem. 2008 Aug 27;56(16):7023-31. doi: 10.1021/jf801227q. Epub 2008 Aug 1.
Isoflavonoids, an interesting and restricted group of secondary metabolites of legumes, exhibit estrogenic, antiangiogenic, and anticancer activities and are now popular as dietary supplements. Plant cell cultures that possess an increased ability to synthesize these metabolites were examined. During the investigation, cell cultures of the Far Eastern relict tree Maackia amurensis (Leguminosae) were established. A selection of seed-derived cell aggregates yielded the callus line designated A-18. This culture produces 20 isoflavonoids, namely, the isoflavones genistein, daidzein, formononetin, calycosin, derrone, and pseudobaptigenin and their glycosylated conjugates genistin, 6''-O-malonylgenistin, ononin, 6''-O-malonylononin, daidzin, 3'-methoxydaidzin, 4'-O-beta-D-glucopyranosyldaidzin, 4'-O-beta-D-glucopyranosylgenistin, and 7-O-beta-D-glucopyranosylcalycosin; the pterocarpans maackiain and medicarpin and their glycosylated conjugates 6'-O-malonyl-3-O-beta-D-glucopyranosylmaackiain and 6'-O-malonyl-3-O-beta-D-glucopyranosylmedicarpin; and the new pterocarpan glucoside 6'-O-malonyl-3-O-beta-D-glucopyranosyl-6,6a-dehydromaackiain.
4.The effect of thermal treatment of whole soybean flour on the conversion of isoflavones and inactivation of trypsin inhibitors.
Andrade JC1, Mandarino JM2, Kurozawa LE1, Ida EI3. Food Chem. 2016 Mar 1;194:1095-101. doi: 10.1016/j.foodchem.2015.08.115. Epub 2015 Sep 3.
The aim of this paper was to evaluate the effect of the thermal treatment of whole soybean flour (WSF) on the conversion of isoflavones and the inactivation of trypsin inhibitors. Soybeans were ground and whole soybean flour was obtained and subjected to heat treatment in an oven for 10, 15 and 20min at 100, 150 and 200°C according to a 3(2) experimental design. The response functions were taken to be the contents of different isoflavone forms and the residual activity of trypsin inhibitors. The thermal treatment in the oven altered the content and profile of the different isoflavones forms. At 200°C for 20min, there was a higher conversion of malonylglycosides to acetylglycosides, β-glycosides and aglycones and a significant reduction in the activity of trypsin inhibitors. Mathematical models were established to estimate the process parameters in obtaining the WSF with isoflavone conversions and reductions in trypsin inhibitor activity.