glycitein and formononetin

Phytoestrogens are naturally occurring nonsteroidal phenolic plant compounds that, due to their molecular structure and size, resemble vertebrate steroids estrogens. This review is focused on plant flavonoids isoflavones, which are ranked among the most estrogenic compounds. The main dietary sources of isoflavones for humans are soybean and soybean products, which contain mainly daidzein and genistein. When they are consumed, they exert estrogenic and/or antiestrogenic effects. Isoflavones are considered chemoprotective and can be used as an alternative therapy for a wide range of hormonal disorders, including several cancer types, namely breast cancer and prostate cancer, cardiovascular diseases, osteoporosis, or menopausal symptoms. On the other hand, isoflavones may also be considered endocrine disruptors with possible negative influences on the state of health in a certain part of the population or on the environment. This review deals with isoflavone classification, structure, and occurrence, with their metabolism, biological, and health effects in humans and animals, and with their utilization and potential risks.

Topics: Animals; Equol; Genistein; Humans; Isoflavones; Phytoestrogens

Alfalfa and red clover are the most widespread and most important perennial legumes, primarily used as a high-quality feed for livestock. Both alfalfa and red clover, as well as some other plant species from Fabaceae family, are a rich natural source of phytoestrogens, nonsteroidal compounds with an estrogenic activity whose beneficial effects in the prevention and treatment of many diseases are demonstrated in numerous scientific studies.. Nowadays, various herbal preparations are present on the world market and their use is constantly increasing, as well as the growing demands of consumers for environmentally sound and health-safe production of plant species used as sources of active substances. Because of their widespread distribution, the possibility of organic breeding, and also significant increases in surface area under genetically modified crops in most EU countries, alfalfa and red clover have become more interesting alternative sources of phytoestrogens. The most common phytoestrogens in these forage legumes are genistein, daidzein, glycitein, formononetin, biochanin, coumestrol, kaempferol and apigenin. The content of these substances is significantly influenced by a number of factors including genotype, environment, production technology, plant maturity stage, and individual plant parts.. Available evidence suggests that forage legumes represent high promising sources of health-promoting phytoestrogens. Due to numerous favorable features, they can find commercial application in different industries such as pharmaceutical, nutraceutical, cosmetic, and agriculture.

Topics: Animals; Biological Products; Biopharmaceutics; Fabaceae; Genistein; Humans; Isoflavones; Phytoestrogens; Plant Leaves; Plant Preparations; Trifolium; Vegetables

S-Equol is a metabolite of daidzein, a type of soy isoflavone, and three reductases are involved in the conversion of daidzein by specific intestinal bacteria. S-Equol is thought to prevent hormone-dependent diseases. We previously identified the equol producing gene cluster (eqlABC) of Eggerthella sp. YY7918. Daidzein reductase (DZNR), encoded by eqlA, catalyzes the reduction of daidzein to dihydrodaidzein (the first step of equol synthesis), which was confirmed using a recombinant enzyme produced in Escherichia coli. Here, we purified recombinant DZNR to homogeneity and analyzed its enzymological properties. DZNR contained FMN, FAD, and one 4Fe-4S cluster per 70-kDa subunit as enzymatic cofactors. DZNR reduced the CC bond between the C-2 and C-3 positions of daidzein, genistein, glycitein, and formononetin in the presence of NADPH. R-Dihydrodaidzein and R-dihydrogenistein were highly stereo-selectively produced from daidzein and genistein. The K

Topics: Actinobacteria; Coenzymes; Equol; Escherichia coli; Flavin Mononucleotide; Flavin-Adenine Dinucleotide; Genistein; Humans; Iron; Isoflavones; NADP; Oxidoreductases; Oxidoreductases Acting on CH-CH Group Donors; Protein Multimerization; Protein Structure, Quaternary; Protein Subunits; Stereoisomerism; Sulfur

Complete separation of aglycones and glucosides of selected isoflavones (genistin, genistein, daidzin, daidzein, glycitin, glycitein, ononin, sissotrin, formononetin, and biochanin A) was possible in 1.5 min using an ultrahigh-pressure liquid chromatography (U-HPLC) on a different particular chemically modified stationary phases with a particle size under 2 microm. In addition, selected separation conditions for simultaneous determination of isoflavones together with a group of phenolic acids (gallic, protocatechuic, p-hydroxybenzoic, vanillic, caffeic, syringic, p-coumaric, ferulic, and sinapic acid) allowed separation of all 19 compounds in 1.9 min. Separations were conducted on a non-polar reversed phase (C(18)) and also on more polar phases with cyanopropyl or phenyl groups using a gradient elution with a mobile phase consisting of 0.3% aqueous acetic acid and methanol. Chromatographic peaks were characterised using parameters such as resolution, symmetry, selectivity, etc. Individual substances were identified and quantified using UV-vis diode array detector at wavelength 270 nm. Limits of detection (3S/N) were in the range 200-400 pg ml(-1). Proposed U-HPLC technique was used for separation of isoflavones and phenolic acids in samples of plant materials (Trifolium pratense, Glycine max, Pisum sativum and Ononis spinosa) after acid hydrolysis of the samples and modified Soxhlet extraction.

Topics: Caffeic Acids; Chromatography, High Pressure Liquid; Coumaric Acids; Gallic Acid; Genistein; Glycine max; Hydroxybenzoates; Isoflavones; Molecular Structure; Pisum sativum; Plant Extracts; Propionates; Trifolium; Vanillic Acid

Several isoflavones [formononetin (1), castanin (5), odoratin (6), glycitein (7), pseudobaptogenin (8), fujikinetin (9), and cuneatin (10)] were isolated from Dalbergia frutescens, and their antiprotozoal activities were determined against Giardia intestinalis. Among these compounds, formononetin (1) was the most potent antigiardial agent, with an IC(50) value of 30 ng/mL (approximately 0.1 microM), as compared to the value for metronidazole, the current drug of choice, of 100 ng/mL (approximately 0.6 microM). Three isoflavones closely related to formononetin [daidzein (2), biochanin A (3) and genistein (4)] were also evaluated, but they were at least 100 times less active than 1. Formononetin (1) may thus be an interesting lead for development of new antigiardial agents or as a probe for a new mechanistic target.

Topics: Animals; Antiprotozoal Agents; Disease Models, Animal; Drugs, Chinese Herbal; Fabaceae; Female; Giardia lamblia; Isoflavones; Magnetic Resonance Spectroscopy; Mice; Plants, Medicinal

Eubacterium limosum (ATCC 8486), a strict anaerobe from the human intestinal tract that is capable of O-demethylation of several compounds, was tested for the ability to metabolize three methoxylated isoflavonoids, biochanin A, formononetin, and glycitein. High-performance liquid chromatography elution profiles of metabolites produced from biochanin A, formononetin, and glycitein showed peaks that had identical retention times to authentic genistein, daidzein, and 6,7,4'-trihydroxyisoflavone, respectively. The metabolites were identified, using an on line liquid chromatography-electrospray mass spectrometer. E. limosum produced 61.4 microM of genistein and 13.2 microM of daidzein from 100 microM of biochanin A and formononetin, after 26 days incubation. O-demethylase activity is cell-associated and was not detected in the extracellular fraction of bacterial culture. This is the first study in which conversion of biochanin A, and formononetin to more potent phytoestrogens by a bacterium has been shown.

Topics: Anaerobiosis; Chromatography, High Pressure Liquid; Eubacterium; Gas Chromatography-Mass Spectrometry; Genistein; Humans; Isoflavones; Oxidoreductases, O-Demethylating