Isoflavone daidzein possesses no antioxidant activities in cell-free assays but induces the antioxidant enzyme catalase

Kampkötter, Andreas; Chovolou, Yvonni; Kulawik, Andreas; Röhrdanz, Elke; Weber, Nadine; Proksch, Peter; Wätjen, Wim

doi:10.1016/j.nutres.2008.06.002

Cited by 44 publications

(35 citation statements)

References 26 publications

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“…Naturally occurring isoflavones have been thought to have very low radical-scavenging activities, 18) although they exhibit various kinds of biological activities that may have some relations to the radical scavenging activities. A possible account for this contradiction has been proposed by the formation of more active derivatives or metabolites through the microbial transformation and/or enzymatic metabolism.…”

Section: Resultsmentioning

confidence: 99%

“…During the course of our research, the antioxidant activity of six kinds of isoflavones and nine metabolites, all of which are naturally available, were reported by two groups 7,18) ; however, the antioxidant activities of the synthetic isoflavones and their derivatives have never been reported. We now present the synthesis of forty-eight kinds of isoflavones 8, thirty-one isoflavanes 9, and fortyseven biphenyl-ketones (10, 10Ј), of which seventy-five compounds are new, and report some relationships of their struc- Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan.…”

Section: )mentioning

confidence: 91%

“…17) Inspired by Hirota's report 17) and the isolation of the A-or B-ring hydroxylated metabolites as well as the C-ring reduced metabolites (4, 5), we started the synthesis of a wide range of isoflavones 8, isoflavanes 9, and the non-cyclic biphenyl-ketones (10, 10Ј) having oxygen-substituents on the A-and/or B-rings to systematically evaluate their DPPH radical scavenging activity. During the course of our research, the antioxidant activity of six kinds of isoflavones and nine metabolites, all of which are naturally available, were reported by two groups 7,18) ; however, the antioxidant activities of the synthetic isoflavones and their derivatives have never been reported. We now present the synthesis of forty-eight kinds of isoflavones 8, thirty-one isoflavanes 9, and fortyseven biphenyl-ketones (10, 10Ј), of which seventy-five compounds are new, and report some relationships of their struc- ture and the DPPH radical scavenging activities (Fig.…”

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confidence: 91%

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Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities

Goto

Terao

Akai

2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Isoflavones are a class of phenolic compounds produced by a variety of higher plants and especially very abundant in soybeans. The major components of soybeans include daidzein 1, genistein 2, and glycitein 3, 1) which are known to have some important biological activities such as estrogenlike activities 1) and antibacterial activities.2) Epidemiologic studies have also shown that the dietary intake of isoflavones is associated with some properties beneficial to human health such as the prevention of coronary heart disease and the reduced risk of breast, prostate, and colon cancers.3,4) Some of these effects are thought to be related to the antioxidant activities of the isoflavonoids 5) similar to that of the flavonoids such as catechins, 6) although the major soybean isoflavones (1-3) have been reported to have low antioxidant activities. 7)The metabolites of natural isoflavones generated by intestinal bacteria and/or enzymes, such as cytochrome P450, 8,9) are the key to understanding the net factors for the physiological efficiency of natural products, because cells are predominantly exposed to metabolites rather than the parent compounds.10,11) For example, equol 4 and O-desmethylangolensin 5 were isolated among the metabolites of 1 (Fig. 1), from which 4 was found to show a more potent estrogen activity than 1.12,13) Several other metabolites of 1 and 2, that have one or two additional hydroxy groups predominantly at the C6-, C8-and C3Ј-positions, have been identified in human urine and plasma.9,14-16) However, their biological activities have been scarcely reported probably due to their very low yields, and therefore, little is known about their structure-activity relationship.In 2004, Hirota et al. isolated the more oxygenated isoflavones, 6-hydroxydaidzein 6 and 8-hydroxyglycitein 7, from fermented soybean miso, which exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities (ED 50 ϭ24-37 mM) as high as that of a-tocopherol (Fig. 1). 17)Inspired by Hirota's report 17) and the isolation of the A-or B-ring hydroxylated metabolites as well as the C-ring reduced metabolites (4, 5), we started the synthesis of a wide range of isoflavones 8, isoflavanes 9, and the non-cyclic biphenyl-ketones (10, 10Ј) having oxygen-substituents on the A-and/or B-rings to systematically evaluate their DPPH radical scavenging activity. During the course of our research, the antioxidant activity of six kinds of isoflavones and nine metabolites, all of which are naturally available, were reported by two groups 7,18) ; however, the antioxidant activities of the synthetic isoflavones and their derivatives have never been reported. We now present the synthesis of forty-eight kinds of isoflavones 8, thirty-one isoflavanes 9, and fortyseven biphenyl-ketones (10, 10Ј), of which seventy-five compounds are new, and report some relationships of their struc- Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan. Received November 13, 2008; accepted February 6, 2009 Forty-eight kinds of isoflavones (8), thirty-one isoflava...

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Section: Resultsmentioning

confidence: 99%

Section: )mentioning

confidence: 91%

mentioning

confidence: 91%

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Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities

Goto

Terao

Akai

2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Isoflavoneare subclass of flavonoids which are found in fruits, nuts, soybeans, and soybased products [1]. Isoflavones have demonstrated a variety of important biological activities, including antioxidant [2], antibacterial [3], osteoporosis [4], anticancer effects [1]- [5]. The biological activity of these compounds is associated with beneficial effects on human health has become an interesting topic in the study of isoflavones including synthetic methods.…”

Section: Introductionmentioning

confidence: 99%

Synthesis 3,4-Dimethoxybenzyl-2,4-Dihydroxyphenyl Ketone from Eugenol

Matsjeh¹,

Anwar²,

N³

et al. 2015

IJCEA

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Abstract-The main content of clove oil is eugenol, amounting to 80-90%. The aims this study to utilize eugenol from clove leave oil as raw material in the synthesis of 3,4-dimethoxybenzyl-2',4'-dihydroxyphenyl ketone with 3,4-dimethoxybenzylcyanide as intermediate compound. Converting eugenol into 3, 4-dimethoxybenzyl cyanide via several stages of reactions. Methylation of eugenol using dimethylsulphate and NaOH as catalyst was produced methyleugenol as much as 89.78% with a purity of 93.6%. Isomerization of methyleugenol using alkaline potassium tertiary butoxide (t-BuOK) in the medium dimethyl sulfoxide (DMSO) was resulted in 87.24 % yield methylisoeugenol with a purity of 88.89%. Methylisoeugenol was oxydated using potassium dichromate (K 2 Cr 2 O 7 ) in a phase transfer catalyst system (PTC) by Polysorbate 80 into a 3,4-dimethoxybenzaldehyde as much as 85.36 % with a purity 83.46 %. Reduction of 3.4-dimethoxybenzaldehyde using sodium borohidrat (NaBH 4 ) was producted 3.4-dimethoxybenzylalcohol as much as 98 % with a purity 100 % level. The 3.4-dimethoxybenzylalcohol was halogenated using SOCl 2 was producted 3.4-dimethoxybenzylchloride which reacted further with sodium cyanide to produce 3.4-dimethoxybenzylcyanide as much as 89.5 % with a purity 99.24%.The acylation reaction of acid 3,4-dimethoxyphenylacetic acid with resorcinol to 3,4-dimethoxybenzyl-2,4-dihydroxyphenyl ketone obtained is a white a solid product having a melting point of 171-172 O C. Rendamen generated from this experiment by 76%. IndexTerms-Eugenol, 3.4-dimethoxybenzylcyanide, 3,4-dimethoxybenzyl-2', 4'dihydroxyphenylketone.

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“…Isoflavones have demonstrated a variety of important biological activities, including antioxidant [2], antibacterial [3], osteoporosis [4] and anticancer activities [5]. The biological activities of these compounds that related to those beneficial effects in human health had become the interest topic in isoflavones research including synthetic method.…”

Section: Introductionmentioning

confidence: 99%