PURPOSE: It has been postulated that soybean isoflavones act as inhibitory factors in several cancers. Recently, various in vitro and in vivo experimental studies have demonstrated that these isoflavones inhibit prostate cancer. Therefore, we investigated whether soybean isoflavones influenced the development of prostate cancer by comparing the levels of circulating isoflavones between prostate cancer patients and controls. MATERIALS AND METHODS: The serum levels of genistein, daidzein and equol were determined using reverse-phase, high-performance liquid chromatography-multiple reaction ion monitoring mass spectrometry(HPLC-MS) and compared in 122 experimental subjects(61 prostate cancer patients and 61 cancer-free controls) from 6 hospitals. RESULTS: The serum concentrations of genistein, daidzein and equol in the patients were 130.7+/-181.4ng/ml, 53.6+/-69.3ng/ml and 11.37+/-43.4ng/ml, with control values of 95.6+/-95.2ng/ml, 55.2+/-121.8ng/ml and 23.2+/-34.5ng/ml, respectively. There was no statistical difference between the 2 groups. Daidzein non-metabolizers who were unable to degrade daidzein into equol were compared between the patients and the controls, and were found to be significantly more common in the patient group (p=0.001, OR=3.44, 95% CI=1.6243-7.2855). However, the equol/daidzein ratio was significantly lower in the patients than in the controls(p=0.0072). No association between age, stage, Gleason score or isoflavone concentrations was found. CONCLUSIONS: These results suggest that the capability to produce equol (i.e., the mechanism for the metabolism of daidzein into equol) is closely involved in the lower incidence of prostate cancer, and that a diet based on soybean isoflavones would be useful in preventing prostate cancer.
Diet ; Equol ; Genistein ; Humans ; Incidence ; Isoflavones ; Metabolism ; Neoplasm Grading ; Prostate* ; Prostatic Neoplasms* ; Soybeans*

PURPOSE: Recent studies have suggested that isoflavones have an inverse correlation with the risk of prostate cancer. In addition, the serum isoflavones levels are thought to be decided not only by the level of intake of isoflavones, but also by the metabolic processes or the genetic abilities required for ingestion of isoflavones. So, we conducted this study to determine the effects of dietary habits on the serum isoflavones levels. MATERIALS AND METHODS: One hundred age- and community-matched healthy men between the ages of 10 and 59 years were interviewed using a food frequency questionnaire that was developed and validated for Korean populations. The individuals' dietary habits during the previous one-year period and the foods they ingested during the previous one-week period before blood sampling were assessed. The serum concentrations of isoflavones were analyzed by the reversed-phase high performance liquid chromatography-multiple reaction ion monitoring-mass spectrometry method (HPLC-MS), (SRL Co. Tokyo, Japan). RESULTS: The genistein and daidzein levels were significantly correlated with age (p=0.026 and p=0.016, respectively), but the equol level was not (p=0.091). The foods associated with the genistein level were unmilled rice, beans, garlic and etc. The foods significantly related to the daidzein level were unmilled rice, garlic and etc. Of the foods ingested during the previous one-week period, fermented soybean soup, garlic, strawberries and mung-bean pancakes were associated with the equol level. CONCLUSIONS: The genistein and daidzein levels were associated with usual dietary habits, but the equol level was related to the short-period food consumption. Changes in dietary habit might induce significant changes in the genistein and daidzein levels.
Eating ; Equol ; Fabaceae ; Food Habits* ; Fragaria ; Garlic ; Genistein ; Humans ; Isoflavones* ; Male ; Metabolism ; Prostatic Neoplasms ; Surveys and Questionnaires ; Soybeans ; Spectrum Analysis

PURPOSE: Isoflavones are rich in soybean and are known to affect bone formation. This study examined the effects and modes of action of isoflavones on the differentiation of C2C12 myoblasts in the presence of the bone morphogenetic protein (BMP)-4. MATERIALS AND METHODS: The isoflavones, daidzein, genistein or equol, and/or BMP-4 were added alone or in combination to C2C12 myoblasts. After 72 hours culture, the cells were stained for the early osteoblastic differentiation marker, alkaline phosphatase (ALP). The ALP activity was determined by comparing the color of the stained images as well as by spectrophotometry. The expression profiles of the extracellular matrix (ECM) genes responsible for the extensive remodeling at the cell surface were analyzed using agene expression microarray after treating thesamples with daidzein. RESULTS: ALP staining of BMP-4 or the isoflavones-treated cells showed that BMP-4 increased the activity of ALP in a dose dependent manner, whereas the isoflavones alone did not induced any remarkable increase. However, the ALP activity increased when the cells were treated with BMP-4 and any of the three isoflavones. The macrogen mouse MAC array data showed that the ECM genes, Mmp13 and Mmp3, were up-regulated by daidzein, whereas Col4a2, Col5a1 and Mmp9 were down-regulated. CONCLUSION: Isoflavones induce osteoblastic differentiation when combined with BMP-4, which is possibly achieved by modulating the expressional levels of various ECM genes.
Alkaline Phosphatase ; Animals ; Bone Morphogenetic Proteins ; Equol ; Extracellular Matrix ; Genistein ; Isoflavones* ; Mice ; Myoblasts* ; Osteoblasts ; Osteogenesis ; Soybeans ; Spectrophotometry

Pueraria thomsonii has long been used in traditional Chinese medicine. Isoflavonoids are the principle pharmacologically active components, which are primarily observed as glycosyl-conjugates and accumulate in P. thomsonii roots. However, the molecular mechanisms underlying the glycosylation processes in (iso)flavonoid biosynthesis have not been thoroughly elucidated. In the current study, an O-glucosyltransferase (PtUGT8) was identified in the medicinal plant P. thomsonii from RNA-seq database. Biochemical assays of the recombinant PtUGT8 showed that it was able to glycosylate chalcone (isoliquiritigenin) at the 4-OH position and glycosylate isoflavones (daidzein, formononetin, and genistein) at the 7-OH or 4'-OH position, exhibiting no enzyme activity to flavonones (liquiritigenin and narigenin) in vitro. The identification of PtUGT8 may provide a useful enzyme catalyst for efficient biotransformation of isoflavones and other natural products for food or pharmacological applications.
Cloning, Molecular ; Genistein ; Glucosyltransferases/metabolism* ; Isoflavones/pharmacology* ; Pueraria/chemistry*

OBJECTIVETo study the chemical constituents of the whole plant Caragana spinifera.

METHODThe chemical constituents were isolated and repeatedly purified on silica gel column. The structures were elucidated by the NMR spectra and physico-chemical properties.

RESULTSix compounds were isolated and identified as (6aR, 11aR) 4,9-dimethoxy-3-hydroxypterocarpan, (6aR,11aR)-4, 9-dihydroxy-3- methoxypterocarpan (melilotocarpane B), 5, 4'-dihydroxy-7-methoxyisoflavone, 7-hydroxy4'-methoxyisoflavone, 6, 7-dihydroxy4'-methoxyisoflavone, beta-sitosterol respectively.

CONCLUSIONAll compounds were isolated from the plant for the first time.

Caragana ; chemistry ; Crystallography, X-Ray ; Drugs, Chinese Herbal ; chemistry ; Isoflavones ; analysis ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; Pterocarpans ; analysis ; chemistry ; isolation & purification

It has been suggested that isoflavones protect the cardiovascular system, in part by attenuating blood pressure. The purpose of the present research was to compare the isoflavone intake and blood lipids between hypertensive and normotensive and to examine dietary management for prevention of hypertension. Anthropometrical measurements, blood pressures, nutrients and isoflavone intakes using the 24-hour recall method, and serum lipids of 81 hypertensives and 77 normotensives were estimated. The average age, height, weight, and BMI were 58.2 years, 158.5 cm, 64.3 kg, and 25.6 kg/m2 for the hypertensive and 58.0 years, 159.4 cm, 63.0 kg, and 24.8 kg/m2 for the normotensive, respectively. Systolic and diastolic blood pressures of the hypertensive were significantly higher than those of the normotensive (p<0.001, p<0.001). The daily food intake of the hypertensive was significantly lower than that of the normotensive (p<0.01). The daily energy intakes of hypertensive and normotesive were 1479.8 kcal and 1590.9 kcal and there was no significant difference between the two groups. Carbohydrate intake of the hypertensive was significantly higher than that of the normotensive (p<0.05). However, daily intakes of plant protein, fiber, ash, calcium, sodium, potassium, and vitamin B1 of the hypertensive were significantly lower than those of the normotensive (p<0.05, p<0.01, p<0.01, p<0.01, p<0.05, p<0.05, p<0.05). The daily intakes of daidzein, genistein, isoflavone of the hypertensive were significantly lower than those of the normotensive (p<0.05, p<0.05, p<0.05). However, isoflavone intakes per 1000 kcal showed no significant difference between the two groups. Serum lipids of the hypertensive and normotensive were 189.6 mg/dL and 187.2 mg/dL for total cholesterol, 157.3 mg/dL and 161.9 mg/dL for triglyceride, 42.9 mg/dL and 43.5 mg/dL for HDL-cholesterol, 115.2 mg/dL and 111.4 mg/dL for LDL-cholesterol, and 3.5 and 3.4 for atherogenic index. In the total subjects, there was a significantly negative correlation between systolic blood pressure and genistein intake (p<0.05). Based on these results, we concluded that the daily intakes of food, energy, and isoflavones of hypertensives were lower than normotensives. Therefore, it should be emphasized that proper dietary management considering these dietary factors for prevention of hypertension.
Blood Pressure ; Calcium ; Cardiovascular System ; Cholesterol ; Eating ; Genistein ; Hypertension ; Isoflavones ; Plants ; Potassium ; Sodium ; Thiamine ; Triglycerides

Recent studies have suggested that natural agents such as isoflavones, resveratrol, and anthocyanin have beneficial effects on metabolic syndrome-related disorders. The objective of this study was to evaluate dietary isoflavone intake, urinary isoflavone level, and their relationship with the risk of metabolic syndrome (MetS) among Korean postmenopausal women. The subjects included 46 MetS and 60 controls. The MetS risk score was determined by adding the number of risk factors such as waist circumference, blood pressure (BP) and levels of triglyceride (TG), HDL-cholesterol, and glucose. Dietary isoflavone intake was not significantly different between the MetS and control groups; however, the urinary daidzein level was significantly higher in the MetS subjects compared to that of the controls. Subjects with high TG had higher urinary daidzein and isoflavone (daidzein + genistein) levels than those without such abnormalities. But, the MetS risk score showed no significant correlation with urinary daidzein, genistein, and isoflavone excretions.
Anthocyanins ; Blood Pressure ; Female ; Genistein ; Glucose ; Humans ; Isoflavones ; Risk Factors ; Triglycerides ; Waist Circumference

This study was conducted to investigate the attitude to various soy foods and to estimate dietary isoflavone intake among Korean adolescents. The survey was carried out by self-administered questionnaire with 800 middle and high school students residing in urban and rural areas and 714 questionnaires were collected: resulting in 89% response rate. The dietary isoflavone intake was estimated by food frequency questionnaire developed for rapid assessment of isoflavone intake. Soybean paste, soybean curd, soy milk, bean sprouts and dambuk were recognized as nutritious and healthy food in order. Dambuk got the lowest score in taste and flavor. Bean sprouts, soybean curd and soybean paste were recognized as familiar food in order. Stuffed rice in fried soybean curd got the highest score and Miso soup got the lowest in preference. More than 50% of the subjects consumed soybean paste stew/soup and soybean curd over twice per week and 12.3% of the subjects consumed soybean over once a day. The estimated daily intake of isoflavones ranged from 0 to 227 mg, and the mean daily isoflavone intake of the subjects was 28.1 mg (16.3 mg genistein and 12.0 mg daidzein) whereas the median value of isoflavone intake was 19.7 mg. There was statistically significant relationship among Kyung Gi Do, Chung cheung Do and Seoul residents in their intake of isoflavone. The highest monthly income group consumed isoflavone more than the other groups. These results suggest that Korean adolescent perceived the soybean dishes as high quality foods but they didn't take much because of difficulty to cook or less chance to eat. Nutrition education program is needed to enhance consuming soy foods for prevention of chronic diseases related to dietary isoflavone intake. More detailed information on easy cook method of soy food is also needed.
Adolescent* ; Chronic Disease ; Education ; Genistein ; Humans ; Isoflavones ; Seoul ; Soy Foods* ; Soy Milk ; Soybeans

OBJECTIVETo study the chemical constituents from the vine stems of isoflavones of Millettia nitita var. hirsutissima.

METHODChromatographic methods were used to isolate compounds, and spectroscopic methods were used to elucidate the structures.

RESULTFour isoflavones were isolated and identified: 3'-O-methylorobol (1), genistein (2), biochanin A (3), afromosin (4).

CONCLUSIONAll Compounds were obtained from the plant for the first time.

Genistein ; chemistry ; isolation & purification ; Isoflavones ; chemistry ; isolation & purification ; Millettia ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry

OBJECTIVETo investigate the isoflavones from the vines of Pueraria lobata.

METHODThe compounds were isolated by column chromatography over silica gel and RP-C18, and purified by Sephadex LH-20 column chromatography and preparative TLC. The structures were elucidated on the basis of physico-chemical properties and spectral data.

RESULTTwelve compounds were isolated and identified as: 3'-methoxydaidzein (1), formononetin (2), genistein (3), daidzein (4), daidzin (5), genistin (6), ononin (7), 5-hydroxyl ononin (8), calycosin (9), 6"-O-acetyl genistein (10), 6"-O-acetyl daidzin (11), puerarin (12).

CONCLUSIONFor the first time, compounds 9-11 were isolated from the genus Pueraria plant, and compounds 1, 3, 6-8 were obtained from the vines of this plant.

Genistein ; chemistry ; Glucosides ; chemistry ; Isoflavones ; chemistry ; Magnetic Resonance Spectroscopy ; Plant Stems ; chemistry ; Pueraria ; chemistry