MetaboLights
A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'.
Identification
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
4',7-dihydroxyisoflavone
4',7-dihydroxyisoflavone
7,4'-dihydroxyisoflavone
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone
7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Daidzein
daidzeol
isoaurostatin
Species
cordyceps sinensis
NCBI:txid72228 21848266
homo sapiens
arabidopsis thaliana
mus musculus
streptomyces clavuligerus
ovis aries
reference compound
glycine max
felis catus
gallus gallus
bacillus subtilis
streptococcus pneumoniae
Europe PubMed Central results
Inhibition of alpha-glucosidase and amylase by luteolin, a flavonoid.
Author: Kim JS, Kwon CS, Son KH.
Abstract: Twenty-one naturally occurring flavonoids were tested for inhibitory activities against alpha-glucosidase (EC 3.2.1.20) and alpha-amylase (EC 3.2.1.1). Luteolin, amentoflavone, luteolin 7-O-glucoside, and daidzein were the strongest inhibitors among the compounds tested. Luteolin inhibited alpha-glucosidase by 36% at the concentration of 0.5 mg/ml and was stronger than acarbose, the most widely prescribed drug, in inhibitory potency, suggesting that it has the possibility to effectively suppress postprandial hyperglycemia in patients with non-insulin dependent diabetes mellitus. Luteolin also inhibited alpha-amylase effectively although it was less potent than acarbose. The clinical value of luteolin needs to be further evaluated.
DOI: 10.1271/bbb.64.2458
Inhibition of alpha-glucosidase and alpha-amylase by flavonoids.
Author: Tadera K, Minami Y, Takamatsu K, Matsuoka T.
Abstract: The inhibitory activity of six groups of flavonoids against yeast and rat small intestinal alpha-glucosidases and porcine pancreatic alpha-amylase was compared, and chemical structures of flavonoids responsible for the inhibitory activity were evaluated. Yeast alpha-glucosidase was potently inhibited by the anthocyanidin, isoflavone and flavonol groups with the IC50 values less than 15 microM. The following structures enhanced the inhibitory activity: the unsaturated C ring, 3-OH, 4-CO, the linkage of the B ring at the 3 position, and the hydroxyl substitution on the B ring. Rat small intestinal alpha-glucosidase was weakly inhibited by many flavonoids, and slightly by the anthocyanidin and isoflavone groups. 3-OH and the hydroxyl substitution on the B ring increased the inhibitory activity. In porcine pancreatic alpha-amylase, luteolin, myricetin and quercetin were potent inhibitors with the IC50 values less than 500 microM. The 2,3-double bond, 5-OH, the linkage of the B ring at the 3 position, and the hydroxyl substitution on the B ring enhanced the inhibitory activity, while 3-OH reduced it.
DOI: 10.3177/jnsv.52.149
Genistein and daidzein: different molecular effects on prostate cancer.
Author: Adjakly M, Ngollo M, Boiteux JP, Bignon YJ, Guy L, Bernard-Gallon D.
Abstract: Diet is believed to play an important role in cancer. It has been revealed by epidemiological studies that Asian populations, who consume phytoestrogens in large amounts, have a lower incidence of prostate cancer in comparison with the Western world, where consumption of soy is lower. Genistein and daidzein, the soy phytoestrogens most widely studied, are believed to be potent anticancer agents and have been shown to possess anticancer properties. It has been shown that these compounds inhibit the growth of cancer cells through the modulation of genes controlling cell-cycle progression. Genistein inhibits the activation of the kappa light polypeptide gene enhancer in B-cells (NF-κB), signaling pathway, which is implicated in the balance between cell survival and programmed cell death (apoptosis). Antioxidant and antiangiogenesis properties of genistein have been also described. Soy isoflavones are also implicated in reversion of epigenetic events observed in prostate cancer. Significant advances have been made for understanding how soy isoflavones are implicated in protection against prostate cancer. However, more studies are needed to better-understand and elucidate all pathways mobilized by genistein and daidzein, in order to fully exploit their anticancer properties.
Antiproliferative activity of daidzein and genistein may be related to ERα/c-erbB-2 expression in human breast cancer cells.
Author: Choi EJ, Kim GH.
Abstract: In this study, we investigated the antiproliferative activity of the isoflavones daidzein and genistein in three breast cancer cell lines with different patterns of estrogen receptor (ER) and c‑erbB‑2 protein expression (ERα‑positive MCF‑7 cells, c‑erbB‑2‑positive SK‑BR‑3 cells and ERα/c‑erbB‑2‑positive ZR‑75‑1). After treatment at various concentrations (1‑200 µM for 72 h), the effect of daidzein and genistein on the proliferation of different cell types varied; these effects were found to be associated with ERα and c‑erbB‑2 expression. Daidzein and genistein exhibited biphasic effects (stimulatory or inhibitory) on proliferation and ERα expression in MCF‑7 cells. Although 1 µM daidzein significantly stimulated cell growth, ERα expression was unaffected. However, genistein showed marked increases in proliferation and ERα expression after exposure to <10 µM genistein. Notably, the inhibition of cell proliferation by 200 µM genistein was greater compared to that by daidzein at the same concentration. Daidzein and genistein significantly inhibited proliferation of SK‑BR‑3 and ZR‑75‑1 cells in a dose‑dependent manner. In addition, ERα and c‑erbB‑2 expression was reduced by daidzein and genistein in both SK‑BR‑3 and ZR‑75‑1 cells in a dose‑dependent manner. However, the effect of genistein was greater compared to that of daidzein. In conclusion, the isoflavones daidzein and genistein showed anti‑breast cancer activity, which was associated with expression of the ERα and c‑erbB‑2 receptors.
Soy protein, genistein, and daidzein improve serum paraoxonase activity and lipid profiles in rheumatoid arthritis in rats.
Author: Mohammadshahi M, Haidari F, Saei AA, Rashidi B, Mahboob S, Rashidi MR.
Abstract: In this study, we investigated the effects of genistein, daidzein, and soy protein on paraoxonase and arylesterase activity, malondialdehyde (MDA) levels, and lipid profiles of arthritic rats in vivo and the results were compared with that of dexamethasone. Seventy-two female Sprague-Dawley rats were divided into six groups: healthy control, animals with collagen-induced arthritis (CIA), CIA-soy protein (7 g/kg)-treated rats, CIA-genistein (20 mg/kg)-treated animals, CIA-daidzein (20 mg/kg)-treated rats, and CIA-dexamethasone (1 mg/kg)-treated rats. Rheumatoid arthritis was induced using collagen type II and the treatments were carried out by daily gavages feedings for 50 days. The paraoxonase activity in serum was measured spectrophotometrically using paraoxon and phenylacetate as substrates. Serum MDA and lipids levels were determined using enzymatic colorimetric methods. Arthritis-induced decreases in paraoxonase and arylesterase activity was restored after treatment with soy protein and isoflavones (P<.05). MDA concentrations were lower after treatment with all tested compounds. However, only soy protein could partially improve the lipid profile.
Daidzein affects steroidogenesis and oestrogen receptor expression in medium ovarian follicles of pigs.
Author: Nynca A, Słonina D, Jablońska O, Kamińska B, Ciereszko RE.
Abstract: Daidzein, a phytoestrogen present in soybean products used in swine feed, has been demonstrated to affect both reproductive and endocrine functions. The aims of this study were to examine the in vitro effects of daidzein on (1) progesterone (P4) and oestradiol (E2) secretion by porcine luteinised granulosa cells harvested from medium follicles, and (2) the mRNA and protein expression of oestrogen receptors α and β (ERα and ERβ) in these cells. The influence of E2 on P4 secretion and ERα and ERβ expression in the granulosa cells of pigs was also investigated. It was found that daidzein inhibited progesterone secretion by luteinised granulosa cells isolated from medium follicles. In contrast, E2 did not affect progesterone production by these cells. Moreover, daidzein did not alter the granulosal secretion of E2. Both daidzein and E2 decreased mRNA expression of ERα in the cells examined. The expression of ERβ mRNA was not affected by daidzein but was inhibited by E2. ERα protein was not detected while ERβ protein was found in the nuclei of the cells. Daidzein and E2 upregulated the expression of ERβ protein in the cells. In summary, the phytoestrogen daidzein directly affected the porcine ovary by inhibiting progesterone production and increasing ERβ protein expression. Daidzein-induced changes in follicular steroidogenesis and granulosal sensitivity to oestrogens may disturb reproductive processes in pigs.
Comparative analysis of mechanical properties of orthodontic aligners produced by different contemporary 3D printers.
Author: Zinelis S, Panayi N, Polychronis G, Papageorgiou SN, Eliades T.
Abstract: <h4>Objective</h4>The aim of this study was to compare the mechanical properties of orthodontic aligners among different commercially available 3D printing devices.<h4>Materials and methods</h4>Five 3D printers (Ka:rv LP 550, Swinwon; "KAR"), (L120, Dazz 3D; "L12"), (MiiCraft 125, Miicraft Jena; "MIC"), (Slash 2, Uniz; "SLS") and (Pro 95, SprintRay; "PRO") were used to prepare orthodontic aligners with dental resin (Tera Harz TC-85DAW, Graphy). The central incisors of each aligner were cut, prepared and evaluated in terms of Martens-Hardness (HM), indentation-modulus (E<sub>IT</sub> ) and elastic-index (η<sub>IT</sub> ) as per ISO14577-1:2002. Force-indentation curves were recorded and differences among printers were checked with generalized linear regressions (alpha=5%).<h4>Results</h4>Statistically significant differences were seen for all mechanical properties (P < .05), which were in descending order: HM (N/mm<sup>2</sup> ) as median (Interquartile Range [IQR]): SLS 108.5 (106.0-112.0), L12 103.0 (102.0-107.0), KAR 101.5 (97.5-103.0), MIC 100.0 (97.5-101.5) and PRO 94.0 (93.0-96.0); E<sub>IT</sub> (MPa) as mean (Standard Deviation [SD]): SLS 2696.3 (124.7), L12 2627.8 (73.5), MIC 2566.2 (125.1), KAR 2565.0 (130.2) and PRO 2491.2 (53.3); and η<sub>IT</sub> (%) as median (IQR): SLS 32.8 (32.3-33.1), L12 31.6 (30.8-32.3), KAR 31.3 (30.9-31.9), MIC 30.5 (29.9-31.2) and PRO 29.5 (29.1-30.0). Additionally, significant differences existed between liquid crystal display (LCD) and digital light processing (DLP) printers for HM (P < .001), E<sub>IT</sub> (P = .002) and η<sub>IT</sub> (P < .001), with aligners from the former having higher values than aligners from the latter printer.<h4>Conclusion</h4>Under the limitations of this study, it may be concluded that the mechanical properties of 3D-printed orthodontic aligners are dependent on the 3D printer used, and thus, differences in their clinical efficacy are anticipated.
DOI: 10.1111/ocr.12537