Synthesis of haginin E, equol, daidzein, and formononetin from resorcinol via an isoflavene intermediate

Li, Sie‐Rong; Chen, Po‐Yuan; Chen, Liang-Yeu; Lo, Yi-Fang; Tsai, Ian‐Lih; Wang, Eng-Chi

doi:10.1016/j.tetlet.2009.02.159

Cited by 22 publications

(12 citation statements)

References 57 publications

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“…The formononetin concentration in red clover ranges from 3.4 to 6.8 mg/g dry mass (Mcmurray et al, 1986). Given the low yield from extraction and limited amount present in raw plant materials, chemical synthesis of formononetin has also been the subject of research due to its clinically important biological activities (Chang et al, 1994; Li et al, 2009). In 1994, the synthesis of formononetin was greatly improved in terms of time and yield by the use of a conventional microwave synthesis method.…”

Section: Overview Of Formononetinmentioning

confidence: 99%

Formononetin: A Review of Its Anticancer Potentials and Mechanisms

et al. 2019

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Cancer, a complex yet common disease, is caused by uncontrolled cell division and abnormal cell growth due to a variety of gene mutations. Seeking effective treatments for cancer is a major research focus, as the incidence of cancer is on the rise and drug resistance to existing anti-cancer drugs is major concern. Natural products have the potential to yield unique molecules and combinations of substances that may be effective against cancer with relatively low toxicity/better side effect profile compared to standard anticancer therapy. Drug discovery work with natural products has demonstrated that natural compounds display a wide range of biological activities correlating to anticancer effects. In this review, we discuss formononetin (C 16 H 12 O 4 ), which originates mainly from red clovers and the Chinese herb Astragalus membranaceus . The compound comes from a class of 7-hydroisoflavones with a substitution of methoxy group at position 4. Formononetin elicits antitumorigenic properties in vitro and in vivo by modulating numerous signaling pathways to induce cell apoptosis (by intrinsic pathway involving Bax, Bcl-2, and caspase-3 proteins) and cell cycle arrest (by regulating mediators like cyclin A, cyclin B1, and cyclin D1), suppress cell proliferation [by signal transducer and activator of transcription (STAT) activation, phosphatidylinositol 3-kinase/protein kinase-B (PI3K/AKT), and mitogen-activated protein kinase (MAPK) signaling pathway], and inhibit cell invasion [by regulating growth factors vascular endothelial growth factor (VEGF) and Fibroblast growth factor 2 (FGF2), and matrix metalloproteinase (MMP)-2 and MMP-9 proteins]. Co-treatment with other chemotherapy drugs such as bortezomib, LY2940002, U0126, sunitinib, epirubicin, doxorubicin, temozolomide, and metformin enhances the anticancer potential of both formononetin and the respective drugs through synergistic effect. Compiling the evidence thus far highlights the potential of formononetin to be a promising candidate for chemoprevention and chemotherapy.

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Section: Overview Of Formononetinmentioning

confidence: 99%

Formononetin: A Review of Its Anticancer Potentials and Mechanisms

et al. 2019

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“…According to the down field shifts of C-4 0 (d H 158.8) and C-7 (d 162.7), two oxy carbons were deduced at C-4 0 and C-7. Therefore, the aglycone of compound 1 was determined as daidzein (Li et al 2009;Yang et al 2013).…”

Section: Resultsmentioning

confidence: 99%

Two new isoflavone 7-O-α-4″-anhydro-4″,5″-didehydroglucuronides from Streptomyces sp. LZ35ΔgdmAI

Deng

Chen

2015

Natural Product Research

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Two isoflavone 7-O-α-4″-anhydro-4″,5″-didehydroglucuronides, namely daidzein 7-O-α-4″-anhydro-4″,5″-didehydroglucuronide (1) and genistein 7-O-α-4″-anhydro-4″,5″-didehydroglucuronide (2), were isolated and identified from the mutant strain of Streptomyces sp. LZ35ΔgdmAI. Their structures were elucidated by the analysis of their high resolution mass spectrometry (HR-MS) and 1D, 2D Nuclear magnetic Resonance (NMR) spectroscopic data. They are new natural products and maybe the transformed products of the soybean meal by Streptomyces sp. LZ35ΔgdmAI.

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“…It is noteworthy that the above two approaches to total syntheses require the involvement of 1 equiv chiral auxiliary or chiral starting material. Additionally, Li et al () suggested a novel synthesis strategy involving a sequence of a Wittig reaction, O‐alkylation, and another Wittig reaction so as to generate isoflavone intermediate. Despite this strategy being capable of higher efficiency and providing an access to these bioactive compounds, the final product equol is a racemic compound.…”

Section: Approaches For Equol Productionmentioning

confidence: 99%

Advances in exploring equol production and application

2019

J Food Process Preserv

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The soybean isoflavone daidzein has been extensively studied. Equol represents the main active metabolite of daidzein in vivo. Due to its broadly biological activities, the preparation and characterization of equol have attracted a great deal of interest. In this review, the focus of attention is placed on the approaches to equol production, including the total synthesis of equol, equol from natural bacteria fermentation and synthetic biology for equol production. It is expected that the industrial production of equol with high yield could be realized in an economic way in the future. In addition, pharmacological activities and clinical applications of equol are also discussed to gain a systematically understanding as to the prospect of development for equol. Practical applications Equol is the main active metabolite of daidzein in vivo and considered to be the most active metabolite of the soybean isoflavones. It has broadly biological activities, including antitumor, antioxidative properties, cardiovascular protection, and relieve menopausal symptoms. However, only 25%–30% of young people can excrete equol in vivo when supplied with soy foods. So, it is necessary to develop efficient methods for equol preparation. Meanwhile, more systematic researches for the pharmacological activity of equol are also required. As mentioned above, this manuscript entitled “Advances in exploring Equol production and application,” hoping that this review should draw widespread attention.

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Synthesis of haginin E, equol, daidzein, and formononetin from resorcinol via an isoflavene intermediate

Cited by 22 publications

References 57 publications

Formononetin: A Review of Its Anticancer Potentials and Mechanisms

Formononetin: A Review of Its Anticancer Potentials and Mechanisms

Two new isoflavone 7-O-α-4″-anhydro-4″,5″-didehydroglucuronides from Streptomyces sp. LZ35ΔgdmAI

Advances in exploring equol production and application

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