New isoflavone glycosides from <Emphasis Type="Italic">Iris spuria</Emphasis> L. (Calizona) cultivated in Egypt

Two new isoflavone glycosides, tectorigenin 7-O-β-d-glucopyranoside-4′-O-[β-d-glucopyranosyl-(1″″ → 6′′′)-β-d-glucopyranoside] (1) and iristectorigenin B 4′-O-[β-d-glucopyranosyl-(1′′′ → 6″)-β-d-glucopyranoside] (2), together with 11 known compounds, including six isoflavones, tectorigenin 7-O-β-d-glucopyranoside-4′-O-β-d-glucopyranoside (3), tectorigenin 4′-O-[β-d-glucopyranosyl-(1′′′ → 6″)-β-d-glucopyranoside] (4), tectorigenin 7-O-β-d-glucopyranoside (5), genistein 7-O-β-d-glucopyranoside (6), tectorigenin 4′-O-β-d-glucopyranoside (7), and tectorigenin (8); two phenolic acid glycosides, vanillic acid 4-O-β-d-glucopyranoside (9) and glucosyringic acid (10); a phenylpropanoid glycoside, E-coniferin (11); an auronol derivative, maesopsin 6-O-β-d-glucopyranoside (12); and a pyrrole derivative, 4-(2-formyl-5-hydroxymethylpyrrol-1-yl) butyric acid (13), were isolated from fresh Iris spuria (Calizona) rhizomes. The structures of these compounds were established on the basis of spectroscopic and chemical evidence. Inhibitory effects on the activation of Epstein–Barr virus early antigen were examined for compounds 1–8 and 12.     

Cholinesterase inhibitory effects of the extracts and compounds of Maclura pomifera (Rafin.) Schneider

We have investigated anticholinesterase potential of the methanol extracts from the leaf, wood, flower, twig, and stem bark of the female and male individuals and rhizodermis and fruit from the female tree of Maclura pomifera (Rafin.) Schneider (Moraceae) along with its major isoflavonoids; osajin and pomiferin as well as their semi-synthetic derivatives; iso-osajin and iso-pomiferin. Anticholinesterase activity was determined by Ellman method using ELISA microplate reader. Osajin and pomiferin had a noticeable inhibition of AChE with IC₅₀ values of 2.239 and 0.096 mM, respectively, while their iso-derivatives were found to display less inhibition towards AChE. The extracts and compounds did not inhibit BChE. The extracts were analyzed for osajin and pomiferin contents by LC–DAD–MS and only the fruits and female flowers contained osajin (fruit: 8.87%, female flowers: 0.19%, w/w) and pomiferin (fruit: 13.6%, female flowers: 0.36%, w/w).     

Ureteral mullerian carcinosarcoma (mixed mullerian tumor) associated with endometriosis occurring in a patient with a concentrated soy isoflavones supplementation

Malignant transformation and particularly malignant mixed mullerian tumor arising in extragenital endometriosis is extremely rare and occurs in the majority of cases after estrogen replacement therapy. We present a case of a 75-year-old woman who developed a ureteral malignant mullerian carcinosarcoma in a context of florid endometriosis. The patient had a history of total hysterectomy with bilateral salpingo-oophorectomy 30 years earlier for extensive endometriosis. Since 5 years, the patient has been on phytoestrogen supplementation consisting of 72 mg/day of superconcentrated soy isoflavones. This is the first case of ureteral mullerian carcinosarcoma arising in endometriosis foci after extensive phytoestrogen supplementation. Our data suggest that phytoestrogens at least in concentrated form may play a role not only in maintenance of endometriosis but also in its malignant transformation. Given the extraordinary popularity and availability of these dietary supplements, several studies are indispensable regarding their safety particularly in women with extensive endometriosis.     

Exposure of juvenile female mice to isoflavone causes lowered expression of estrogen-related receptor gamma gene in vagina

In our previous study, the vaginal opening (VO) day of C57BL/6 mice was accelerated several days by chronic exposure to a 0.05% isoflavone (IF) fortified diet. The purpose of this study was to investigate whether the acceleration of VO by IF (1) has a critical window, (2) is modified by IF exposure combined with 17β-estradiol (E2), and (3) has any relation with gene expressions of estrogen-related receptors (ERRs). As a result, we determined that the critical window for the acceleration of VO was between 15 and 21 days postnatal. The combined effect of E2 and IF was thought to be additional in the acceleration of VO. The gene expression of ERRγ was significantly decreased in vagina by IF. The reduction of ERRγ may have two possible sequelae: disarrangement of vaginal development and high risk of vaginal cancer. In conclusion, IF exposure has a critical window for acceleration of VO and may have adverse effect on mouse vagina.     

大豆异黄酮对去卵巢大鼠主动脉晚期糖化终末产物(AGEs)及脂质过氧化的影响

目的：探讨大豆异黄酮对去卵巢(OVX)大鼠晚期糖化终末产物(AGEs)和血清脂质过氧化物的影响。方法：将6月龄雌性SD大鼠随机分为假手术组(Sham)、去卵巢组(OVX)和去卵巢 大豆异黄酮组(OVX ISO)。去除双侧卵巢2周后治疗13周。禁食24h，取血，处死动物，取主动脉，分别测定主动脉AGEs含量、血脂和血清过氧化物含量。结果：与假手术组相比，去卵巢组主动脉AGEs，血清甘油三酯(TG)、氧化低密度脂蛋白(OX-LDL)和丙二醛(MDA)含量均明显升高，高密度脂蛋白—胆固醇(HDL-C)、载脂蛋白AI(apo-AI)和超氧化物歧化酶(SOD)活性均显著降低。大豆异黄酮明显调节这些改变。结论：大豆异黄酮通过降低去卵巢大鼠主动脉AGEs含量，血清OX-LDL和MDA水平，提高SOD活性，调节血脂，预防和减少动脉粥样硬化的发生。     

Inhibition of IL-1β and IL-6 in osteoblast-like cell by isoflavones extracted fromSophorae fructus

Osteoporosis is recognized as one of the major hormonal deficiency diseases, especially in menopausal women and the elderly. When estrogen is reduced in the body, local factors such as IL-1beta and IL-6, which are known to be related with bone resorption, are increased and promote osteoclastogenesis, which is responsible for bone resorption. In the present study, we investigated whether glucosidic isoflavones (Isocal, PIII) extracted from Sophorae fructus affect the proliferation of osteoblasts and prevent osteoclastogenesis in vitro by attenuating upstream cytokines such as IL-1beta and IL-6 in a human osteoblastic cell line (MG-63) and in a primary osteoblastic culture from SD rat femurs. Interestingly, IL-1beta and IL-6 mRNA were significantly suppressed in osteoblast-like cells treated with 17beta-estradiol (E2) and PIII when compared to positive control (SDB), and this suppression was more effective at 10(-8)% than at the highest concentration of 10(-4)%. In addition, these were confirmed in protein levels using ELISA assay. In the cell line, the cells showed that E2 was the most effective in osteoblastic proliferation over the whole range of concentration (10(-4)%-10(-12)%), even though PIII also showed the second greatest effectiveness at 10(-8)%. Nitric oxide (NO) was significantly (p<0.05) upregulated in PIII and E2 over the concentration range 10(-6)% to 10(-8)% when compared to SDB, without showing any dose dependency. In bone marrow primary culture, we found by TRAP assay that PIII effectively suppressed osteoclastogenesis next to E2 in comparison with SDB and culture media (control). In conclusion, these results suggest that local bone-resorbing cytokines can be regulated by PIII at lower concentrations and that, therefore, PIII may preferentially induce anti-osteoporosis response by attenuating osteoclastic differentiation and by upregulating NO.     

Phytoestrogens and cognitive function: a review

Neuroprotective effects of phytoestrogen compounds (found in soy) have been demonstrated in animal research and cell culture studies. In particular, phytoestrogens have been shown to reduce Alzheimer's Disease (AD) related pathology, potentially alleviating risk of AD progression. In addition to their antioxidant properties, soy products also have the ability to affect cognition via interaction with estrogen receptors. However, observational studies and randomised controlled trials in humans have resulted in inconclusive findings within this domain. There are several possible reasons for these discrepant data. Studies which report no effect of phytoestrogens on cognition have mainly been carried out in European cohorts, with an average low dietary consumption. In contrast, investigation of Asian populations, with a higher general intake of tofu (a non-fermented soy product) have shown negative associations with cognitive function in those over the age of 65. Consideration of type of soy product is important, as in the latter sample, protective effects of tempe (fermented soy) were also observed. Limited data provide evidence that effects of phytoestrogens on cognition may be modified by dosage, duration of consumption and cognitive test used. Additionally, characteristics of the study population including age, gender, ethnicity and menopausal status appear to be mediating variables. Phytoestrogen treatment interventions have also shown time-limited positive effects on cognition. These findings are consistent with estrogen treatment studies, where initial positive short-term cognitive effects may occur, which reverse with long-term continuous use in elderly women. Well controlled, large scale studies are needed to assess the effects of phytoestrogens on the aging brain and provide further understanding of this association.     

Phytochemical and biological activities of Bituminaria bituminosa L. (Fabaceae)

ObjectiveTo investigate the phytochemical composition, the antioxidant and antibacterial activities of Bituminaria bituminosa L. (Fabaceae) (B. bituminosa).MethodsThe aerial parts of B. bituminosa yielded two compounds. The structures of these compounds were determinated using UV, ¹H-NMR and ¹³C-NMR experiments and comparison of their spectroscopic properties with literature data. The antibacterial activity of the extracts (CH₂Cl₂, ethyl acetate and n-BuOH) was determinated using disk diffusion method against standard and clinical strains. Antioxidant potential of n-BuOH extract was evaluated through two methods: DPPH and cupric ion reducing antioxidant capacity assay.ResultsThe n-BuOH extract from B. bituminosa yielded the isolation of isoflavone and flavone. The extracts CH₂Cl₂, ethyl acetate and n-BuOH demonstrated significant antibacterial activities. CH₂Cl₂ extract showed the maximum antibacterial activity with high concentration of 2 mg/mL against Staphylococcus aureus ATCC 29213, Klebsiella pneumonia and Escherichia coli ATCC 25922 (20.45 mm, 16.41 mm and 15.74 mm inhibition zone, respectively). The value IC₅₀ was 0.26 μg/mL for n-BuOH extract using DPPH method. Whereas the E% value was 0.10 L/mg every centimeter for cupric ion reducing antioxidant capacity assay.ConclusionsThe phytochemical study of B. bituminosa revealed the presence of isoflavone (daidzin) and flavone (isoorientin) and identified for the first time in this specie. The antibacterial activity of the plant B. bituminosa is certainly related to its chemical content. The n-BuOH extract showed a significant antioxidant activity.     

Isoflavone maternal-supplementation during periconception period: Influence on the reproductive organs of the first generation (F1) murine weanling-stage offspring

ObjectiveTo determine the influence of maternal Isoflavone-supplementation during peri-conception period on the reproductive organs of the first generation (F1) murine weanling-stage offspring.MethodsSexually-mature female mice were randomly distributed into the Control group (C) that was fed with food pellets only, treatment groups that were designated as High Dose (HD), Medium Dose (MD) and Low dose (LD) that were fed with food pellets + Isoflavone Genistein dosages of 150.0, 100.0, and 50.0 mg/kg body weight, respectively. Supplement was given two weeks prior to mating and throughout a 21-day gestation period. The pups that were delivered on the 21st day were allowed to mature up to the 28th-day postnatal age then sacrificed by cervical dislocation. The testis and epididymis of males and ovaries and oviducts of females were obtained for histological analyses.ResultsHistological analysis of the testes showed clogged luminal spaces and indistinct population of spermatogenic cells in the HD group while the development of the ovaries from all test groups appeared intact. The luminal and tubular diameter of epididymis were unaffected in the isoflavone-supplemented groups. The epididymis of HD group exhibited poorly developed cauda segment and atrophy of the caput segment but not for MD and LD groups. The oviducts of the HD and MD groups exhibited collapsed muscularis layer and indistinguishable mucosa layer with HD being the more severe. The LD and Control groups showed well-developed mucosa layer.ConclusionResults showed that maternal isoflavone-supplementation when administered at a high dose of 150 mg/kg body weight during peri-conception period can induce adverse effects on the reproductive organs of first generation (F1) murine weanling-stage offspring.     

异黄酮化合物的生物效能及在血吸虫病控制中的作用

本文综述了异黄酮化合物的生物效能及其杀血吸虫和钉螺的作用，并就其用于控制血吸虫病传播的前景进行了展望。