486-66-8Relevant articles and documents
Purification of 2-hydroxyisoflavanone dehydratase from the cell cultures of Pueraria lobata
Hakamatsuka, Takashi,Mori, Kazumi,Ishida, Shinichi,Ebizuka, Yutaka,Sankawa, Ushio
, p. 497 - 505 (1998)
2-Hydroxyisoflavanone dehydratase, which catalyzes the final step of the formation of the isoflavonoid skeleton, was purified and characterized from yeast extract-elicited cell suspension cultures of Pueraria lobata. 2- Hydroxyisoflavanone, the substrate of the dehydratase, is the product of 2- hydroxyisoflavanone synthase, as cytochrome P-450 which catalyzes the hydroxylation step associated with aryl migration of flavanone. The dehydratase was purified to apparent homogeneity for the first time by a seven-step purification procedure. It is a single polypeptide with a molecular weight of 38 kDa, and has an isoelectric point at pH 5.1 and a pH optimum at 6.8. It required no co-factor, and the apparent Michaelis constant for 2,7,4'-trihydroxyisoflavanone was 7.0 mM.
P-450-DEPENDENT OXIDATIVE REARRANGEMENT IN ISOFLAVONE BIOSYNTHESIS: RECONSTITUTION OF P-450 AND NADPH:P-450 REDUCTASE
Hakamatsuka, Takashi,Hashim, Muhammed Faisal,Ebizuka, Yutaka,Sankawa, Ushio
, p. 5969 - 5978 (1991)
The reaction mechanism of oxidative rearrangement in the conversion of liquiritigenin, a flavanone, into 2,7,4'-trihydroxyisoflavanone was studied in elicitor-challenged Pueraria lobata cell cultures.The involvement of cytochrome P-450 in the reaction, hydroxylation associated with 1,2-aryl migration, was proved previously by the inhibition experiments with carbon monoxide and P-450 inhibitors.In order to obtain rigorous evidence proving that the enzyme is a P-450, a reconstitution experiment was performed with solubilized cytochrome P-450 and NADPH:cytochrome P-450 reductase fractions.During these studies we noticed that various biosynthetic reactions can be interpreted as P-450-mediated reactions associated with migration or bond cleavage.Ring contraction of 7-hydroxy-kaurenoic acid in gibberellin biosynthesis, the formation of a furan ring in furanocoumarin biosynthesis and several rearrangement reactions in steroid metabolism are discussed as examples of P-450 reactions associated with migration or bond cleavage.
Highly efficient enzymatic preparation of daidzein in deep eutectic solvents
Cheng, Qi-Bin,Zhang, Li-Wei
, (2017)
Daidzein, which is scarce in nature, has gained significant attention due to its superior biological activity and bioavailability compared with daidzin. So far, it has been widely used in the medicine and health care products industries. The enzymatic approach for the preparation of daidzein has prevailed, benefitted by its high efficiency and eco-friendly nature. Our present research aimed at providing a preparation method of daidzein by enzymatic hydrolysis of daidzin in a new "green" reaction medium-deep eutectic solvents (DESs). Herein, the DESs were screened via evaluating enzyme activity, enzyme stability and the substrate solubility, and the DES (ChCl/EG 2:1, 30 vol %) was believed to be the most appropriate co-solvent to improve the bioconversion efficiency. Based on the yield of daidzein, response surface methodology (RSM) was employed to model and optimize the reaction parameters. Under these optimum process conditions, the maximum yield of 97.53% was achieved and the purity of daidzein crude product reached more than 70%, which is more efficient than conversions in DESs-free buffer. Importantly, it has been shown that DESs medium could be reused for six batches of the process with a final conversion of above 50%. The results indicated that this procedure could be considered a mild, environmentally friendly, highly efficient approach to the economical production of daidzein, with a simple operation process and without any harmful reagents being involved.
Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water
Chang, Ya-Ting,Liu, Ling-Jun,Peng, Wen-Sheng,Lin, Lin-Ting,Chan, Yi-Tsu,Tsai, Fu-Yu
, p. 469 - 475 (2021/02/03)
Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.
Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation
Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na
, (2021/07/01)
In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.
Structure–activity relationship of phytoestrogen analogs as ERα/β agonists with neuroprotective activities
Cho, Hye Won,Gim, Hyo Jin,Li, Hua,Subedi, Lalita,Kim, Sun Yeou,Ryu, Jae-Ha,Jeon, Raok
, p. 99 - 105 (2021/01/06)
A set of isoflavononid and flavonoid analogs was prepared and evaluated for estrogen receptor α (ERα) and ERβ transactivation and anti-neuroinflammatory activities. Structure–activity relationship (SAR) study of naturally occurring phytoestrogens, their metabolites, and related isoflavone analogs revealed the importance of the C-ring of isoflavonoids for ER activity and selectivity. Docking study suggested putative binding modes of daidzein 2 and dehydroequol 8 in the active site of ERα and ERβ, and provided an understanding of the promising activity and selectivity of dehydroequol 8. Among the tested compounds, equol 7 and dehydroequol 8 were the most potent ERα/β agonists with ERβ selectivity and neuroprotective activity. This study provides knowledge on the SAR of isoflavonoids for further development of potent and selective ER agonists with neuroprotective potential.
Water-in-oil skin-whitening skin care lotion and preparation method thereof
-
Paragraph 0040; 0044-0045, (2020/08/09)
The invention discloses a water-in-oil skin-whitening skin care lotion. The water-in-oil skin-whitening skin care lotion comprises the following components in parts by weight of 26-29 parts of camellia oil, 18-23 parts of grape seed oil, 22-25 parts of squalane, 2-3 parts of an oxidation resisting skin whitening agent, 4-6 parts of emulsifying wax, 8-16 parts of distilled water, 11-14 parts of a hydrating agent, and 1-2 parts of a surfactant. The prepared oxidation-resisting skin whitening agent contains sulphadiazine, has certain properties of resisting bacteria and inhibiting bacteria, can effectively realize efficacy of sterilizing and diminishing inflammation of skin care products, can effectively restrain breeding of bacteria, can realize antiseptic effects, can further reduce addition of preservatives in the lotion, can effectively reduce burden to skin, and can further effectively solve the problems that in the preparation process of conventional skin care products, the preservative is directly added to the skin care products to achieve the antibacterial effect, but the added preservative can easily increase the burden to skin, and the preservative has definite stimulability, so that more crowds have intolerance to the prepared skin care lotion.
Transient and Recyclable Halogenation Coupling (TRHC) for Isoflavonoid Synthesis with Site-Selective Arylation
Wan, Jie-Ping,Tu, Zhi,Wang, Yuyun
supporting information, p. 6907 - 6910 (2019/05/10)
A transient and recyclable C?H iodination has been designed for the synthesis of isoflavonoids through the domino reactions of o-hydroxyphenyl enaminones and aryl boronic acids in the presence of catalytic KI and Pd catalyst. Instead of the conventional cross-coupling strategy employing pre-halogenated substrates, this method transforms raw C?H bond by means of a transient C?H halogenation to smoothly relay the subsequent C-arylation. Consequently, such a method avoids the pre-functionalization for C?halogen bond installation as well as the generation of stoichiometric halogen-containing waste following the cross-coupled product, disclosing an intriguing new coupling protocol to forge the C?C bond in the virgin area between classical C?X (X=halogen) bond cross coupling and the C?H activation.
Synthesis of daidzein glycosides, α-tocopherol glycosides, hesperetin glycosides by bioconversion and their potential for anti-allergic functional-foods and cosmetics
Fujitaka, Yuya,Hamada, Hiroki,Uesugi, Daisuke,Kuboki, Atsuhito,Shimoda, Kei,Iwaki, Takafumi,Kiriake, Yuya,Saikawa, Tomohiro
, (2019/08/21)
Daidzein is a common isoflavone, having multiple biological effects such as anti-inflammation, anti-allergy, and anti-aging. α-Tocopherol is the tocopherol isoform with the highest vitamin E activity including anti-allergic activity and anti-cancer activity. Hesperetin is a flavone, which shows potent anti-inflammatory effects. These compounds have shortcomings, i.e., water-insolubility and poor absorption after oral administration. The glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio- and pharmacological properties. They were transformed by cultured Nicotiana tabacum cells to 7-β-glucoside and 7-β-gentiobioside of daidzein, and 30- and 7-β-glucosides, 30,7-β-diglucoside, and 7-β-gentiobioside of hesperetin. Daidzein and α-tocopherol were glycosylated by galactosylation with β-glucosidase to give 40- and 7-β-galactosides of daidzein, which were new compounds, and α-tocopherol 6-β-galactoside. These nine glycosides showed higher anti-allergic activity, i.e., inhibitory activity toward histamine release from rat peritoneal mast cells, than their respective aglycones. In addition, these glycosides showed higher tyrosinase inhibitory activity than the corresponding aglycones. Glycosylation of daidzein, α-tocopherol, and hesperetin greatly improved their biological activities.
Three new isoflavonoid glycosides from the mangrove-derived actinomycete micromonospora aurantiaca 110B
Wang, Rui-Jun,Zhang, Shao-Yong,Ye, Yang-Hui,Yu, Zhen,Qi, Huan,Zhang, Hui,Xue, Zheng-Lian,Wang, Ji-Dong,Wu, Min
, (2019/05/24)
The mangrove ecosystem is a rich resource for the discovery of actinomycetes with potential applications in pharmaceutical science. Besides the genus Streptomyces, Micromonospora is also a source of new bioactive agents. We screened Micromonospora from the rhizosphere soil of mangrove plants in Fujian province, China, and 51 strains were obtained. Among them, the extracts of 12 isolates inhibited the growth of human lung carcinoma A549 cells. Strain 110B exhibited better cytotoxic activity, and its bioactive constituents were investigated. Consequently, three new isoflavonoid glycosides, daidzein-40-(2-deoxy-a-l-fucopyranoside) (1), daidzein-7-(2-deoxy-a-l-fucopyranoside) (2), and daidzein-40,7-di-(2-deoxy-a-l-fucopyranoside) (3) were isolated from the fermentation broth of strain 110B. The structures of the new compounds were determined by spectroscopic methods, including 1D and 2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESIMS). The result of medium-changing experiments implicated that these new compounds were microbial biotransformation products of strain M. aurantiaca 110B. The three compounds displayed moderate cytotoxic activity to the human lung carcinoma cell line A549, hepatocellular liver carcinoma cell line HepG2, and the human colon tumor cell line HCT116, whereas none of them showed antifungal or antibacterial activities.
