Estrogenic and Anticarcinogenic Properties of Kurarinone, a Lavandulyl Flavanone from the Roots of Sophora f lavescens

Laboratory of Pharmacognosy and Phytochemistry, Faculty of Pharmaceutical Sciences, Ghent University, Harelbekestraat 72, B-9000 Ghent, Belgium.
Journal of Natural Products (Impact Factor: 3.8). 12/2004; 67(11):1829-32. DOI: 10.1021/np040069a
Source: PubMed


Kurarinone, a lavandulyl flavanone, was isolated from a polyphenolic extract of the roots of Sophora flavescens using fractionation guided by estrogenic activity, which was determined by recombinant yeast and Ishikawa Var-I bioassays. Kurarinone showed weak estrogenic activity both in the yeast screen and in the Ishikawa Var-I assay with EC(50) values of 4.6 and 1.66 microM, respectively. Furthermore, kurarinone was found to have potent cytotoxic activity (IC(50) value = 22.2 microM) against human MCF-7/6 breast cancer cells in the sulforhodamine-B assay.

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    • "Natural extracts of S. flavescens include a volatile flavonoid component (Kuroyanagi et al. 1999). Previous studies have shown that the major antimicrobial components of S. flavescens are kurarinone, kuraridin, and sophoraflavanone G (De Naeyer et al. 2004; Piao et al. 2006; Han et al. 2007), and antimicrobial activity is related to the quantities of these three major components (Chong et al. 2013). However, this chemical composition can be altered by environmental factors, particularly by temper- ature. "
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    ABSTRACT: Bioaerosols, such as bacterial and fungal cells and their spores, are components of indoor airborne particulate matter and have been associated with human health problems as well as various environmental issues. Natural antimicrobial products have been used in air filters for bioaerosol control. However, natural products may lose some function due to their sensitivity to environmental factors such as temperature and humidity. In this study, we investigated the effects of temperature on antimicrobial fiber filters coated with nanoparticles of a natural product, namely, Sophora flavescens extract. Inactivation efficiency decreased with increasing temperature and treatment time. A quantitative chemical analysis of the filters revealed that the quantities of antimicrobial compounds decreased noticeably, with a consequent decrease in antimicrobial activity. In addition, the S. flavescens nanoparticles on the filter fiber surface melted gradually as treatment time increased at temperatures >100°C. This change in nanoparticle morphology in turn affected the pressure and filtration efficiency of filters, both of which decreased with increasing temperature and treatment time. These results could provide a scientific basis for the improvement of indoor air-quality control using antimicrobial air filters coated with S. flavescens nanoparticles.Copyright 2014 American Association for Aerosol Research
    Aerosol Science and Technology 03/2014; 48(3). DOI:10.1080/02786826.2013.870660 · 2.41 Impact Factor
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    • "In particular, prenylated flavonoids in higher plants protect them by exhibiting strong antibacterial and antifungal activities (Sohn et al., 2004). Many prenylated flavonoids have been identified as active components in medicinal plants with biological activities, such as anticancer, anti-androgen, anti-leishmania, and anti-nitric oxide production (De Naeyer et al., 2004; Ahmed-Belkacem et al., 2005; Han et al., 2006). Due to the beneficial effects for human health, prenylated flavonoids are of particular interest as lead compounds for producing new drugs and functional foods. "
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    ABSTRACT: Prenylated flavonoids are natural compounds that often represent the active components in various medicinal plants and exhibit beneficial effects on human health. Prenylated flavonoids are hybrid products composed of a flavonoid core mainly attached to either 5-carbon (dimethylallyl) or 10-carbon (geranyl) prenyl groups derived from isoprenoid (terpenoid) metabolism, and the prenyl groups are crucial for their biological activity. Prenylation reactions in vivo are crucial coupling processes of two major metabolic pathways, the shikimate-acetate and isoprenoid pathways, in which these reactions are also known as a rate-limiting step. However, none of the genes responsible for the prenylation of flavonoids has been identified despite more than 30 years of research in this field. We have isolated a prenyltransferase gene from Sophora flavescens, SfN8DT-1, responsible for the prenylation of the flavonoid naringenin at the 8-position, which is specific for flavanones and dimethylallyl diphosphate as substrates. Phylogenetic analysis shows that SfN8DT-1 has the same evolutionary origin as prenyltransferases for vitamin E and plastoquinone. The gene expression of SfN8DT-1 is strictly limited to the root bark where prenylated flavonoids are solely accumulated in planta. The ectopic expression of SfN8DT-1 in Arabidopsis thaliana resulted in the formation of prenylated apigenin, quercetin, and kaempferol, as well as 8-prenylnaringenin. SfN8DT-1 represents the first flavonoid-specific prenyltransferase identified in plants and paves the way for the identification and characterization of further genes responsible for the production of this large and important class of secondary metabolites.
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    ABSTRACT: 7,9,2′,4′-Tetrahydroxy-8-isopentenyl-5-methoxychalcone (THIPMC), isolated from the roots of Sophora flavescens Ait., was found to be active against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE), either alone or in combination with ampicillin (AM) or gentamicin (GM), vis checkerboard assay. Minimum inhibitory concentrations ranged from 1 to 8 μg/mL for THIPMC, from 128 to 1024 μg/mL for AM, and from 128 to 512 μg/ mL for GM, respectively. The combinations of THIPMC plus AM or GM yielded a fractional inhibitory concentration index ranging from 0.188 to 0.375 μg/mL, thereby indicating a synergistic effect. These findings suggest that THIPMC alone or in combination with antibiotics against MRSA might be useful for controlling MRSA infections. However, VRE infection was only effectively treated by THIPMC alone.
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