- A facile access for the synthesis of 1-hetero(aryl)-1,2,3-triazoles linked to equol under mild conditions
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We herein report a convenient methodology for the synthesis of 1-hetero(aryl)-1,2,3-triazoles linked with equol by utilizing copper-catalyzed azide-alkyne cycloaddition reaction under exceptionally mild conditions. The salient features of this developed p
- Nibin Joy, Muthipeedika,Beliaev, Nikolai,Beryozkina, Tetyana V.,Bakulev, Vasiliy A.
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- Structural modification and antihypertensive activity study of formononetin derivatives
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A series of formononetin derivatives with substituted benzyloxy groups on the 4′ position of isoflavone were designed and synthesized. Their vasodilative activities were evaluated by wire myograph system on isolated rat mesenteric arterial ring. The preli
- Guo, Qiu-Hong,Li, Jing,Ma, Dong-Lai,Zhou, Li,Zuo, Sai-Jie
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- Scope and Applications of 2,3-Oxidative Aryl Rearrangements for the Synthesis of Isoflavone Natural Products
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The reaction of flavanones with hypervalent iodine reagents was investigated with a view to the synthesis of naturally occurring isoflavones. In contrast to several previous reports in the literature, we did not observe the formation of any benzofurans via a ring contraction pathway, but could isolate only isoflavones, resulting from an oxidative 2,3-aryl rearrangement, and flavones, resulting from an oxidation of the flavanones. Although the 2,3-oxidative rearrangement allows a synthetically useful approach toward some isoflavone natural products due to the convenient accessibility of the required starting materials, the overall synthetic utility and generality of the reaction appear to be more limited than previous literature reports suggest.
- Kwesiga, George,Schmidt, Bernd,Sperlich, Eric
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p. 10699 - 10712
(2021/08/20)
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- Design, synthesis and the structure-activity relationship of agonists targeting on the ALDH2 catalytic tunnel
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ALDH2, a key enzyme in the alcohol metabolism process, detoxifies several kinds of toxic small molecular aldehydes, which induce severe organ damages. The development of novel Alda-1 type ALDH2 activators was mostly relied on HTS but not rational design so far. To clarify the structure–activity relationship (SAR) of the skeleton of Alda-1 analogs by synthesis of the least number of analogs, we prepared 31 Alda-1 analogs and 3 isoflavone derivatives and evaluated for their ALDH2-activating activity. Among these, the ALDH2-activating activity of mono-halogen-substituted (Cl and Br) N-piperonylbenzamides 3b and 3 k, and non-aromatic amides 8a-8c, were 1.5–2.1 folds higher than that of Alda-1 at 20 μM. The relationship between binding affinity in computer aided molecular docking model and the ALDH2-activating activity assays were clarified as follows: for Alda-1 analogs, with the formation of halogen bonds, the enzyme-activating activity was found to follow a specific regression curve within the range between ?5 kcal/mol and ?4 kcal/mol. For isoflavone derivatives, the basic moiety on the B ring enhance the activating activity. These results provide a new direction of utilizing computer-aided modeling to design novel ALDH2 agonists in the future.
- Cheng, Ming-Che,Lo, Wei-Chi,Chang, Yu-Wen,Lee, Shoei-Sheng,Chang, Chia-Chuan
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- Daidzein analogs as treatment for cancer
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Provided are compositions for treatment of cancers, including breast cancer, comprising at least one novel daidzein analog, as well as methods of using the same for preventing or treating cancer or tumor growth.
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(2017/08/26)
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- Design and synthesis of 3-arylbenzopyran based non-steroidal vitamin-D3 mimics as osteogenic agents
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3-Arylbenzopyran based non-steroidal osteogenic agents have been explored as structural templates of estrogen and vitamin-D3. The target molecules 18a-c, 19a-c, 26a-c, 27a-c and intermediates 17a-c and 25a-c were studied for their osteogenic activity in an osteoblast differentiation assay in vitro using mouse calvarial osteoblast cells. Compounds 25c, 26b, 27b and 27c effectively increased ALP activity at 1 pM concentration compared to the untreated cells. The active compounds were devoid of inherent toxicity at 1 pM concentration in osteoblast cells. The most active compound, 27b, was studied for mineralization of osteoblast cells and expression of marker genes, viz. BMP-2, RUNX-2 & Osx, involved in osteogenesis. Molecular docking analysis performed for 27b showed its possible interactions with estrogen receptor-α and -β (ER-α and ER-β) as well as the vitamin-D receptor (VDR).
- Ahmad, Mohd. Imran,Raghuvanshi, Dushyant Singh,Singh, Sarita,John, Aijaz A.,Prakash, Ravi,Nainawat, Kripa Shankar,Singh, Divya,Tripathi, Shubhandra,Sharma, Ashok,Gupta, Atul
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p. 2381 - 2394
(2016/12/18)
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- Induction of targeted osteogenesis with 3-aryl-2H-benzopyrans and 3-aryl-3H-benzopyrans: Novel osteogenic agents
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Development of target oriented chemotherapeutics for treatment of chronic diseases have been considered as an important approach in drug development. Following this approach, in our efforts for exploration of new osteogenic leads, substituted 3-aryl-2H-be
- Gupta, Atul,Ahmad, Imran,Kureel, Jyoti,Hasanain, Mohammad,Pandey, Praveen,Singh, Sarita,John, Aijaz A.,Sarkar, Jayanta,Singh, Divya
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- Combinatorial synthesis of structurally diverse triazole-bridged flavonoid dimers and trimers
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Flavonoids are a large family of compounds associated with a broad range of biologically useful properties. In recent years, synthetic compounds that contain two flavonoid units linked together have attracted attention in drug discovery and development projects. Numerous flavonoid dimer systems, incorporating a range of monomers attached via different linkers, have been reported to exhibit interesting bioactivities. From a medicinal chemistry perspective, the 1,2,3-triazole ring system has been identified as a particularly attractive linker moiety in dimeric derivatives (owing to several favourable attributes including proven biological relevance and metabolic stability) and triazole-bridged flavonoid dimers possessing anticancer and antimalarial activities have recently been reported. However, there are relatively few examples of libraries of triazole-bridged flavonoid dimers and the diversity of flavonoid subunits present within these is typically limited. Thus, this compound type arguably remains underexplored within drug discovery. Herein, we report a modular strategy for the synthesis of novel and biologically interesting triazole-bridged flavonoid heterodimers and also very rare heterotrimers from readily available starting materials. Application of this strategy has enabled step-efficient and systematic access to a library of structurally diverse compounds of this sort, with a variety of monomer units belonging to six different structural subclasses of flavonoid successfully incorporated.
- Sum, Tze Han,Sum, Tze Jing,Galloway, Warren R. J. D.,Collins, Súil,Twigg, David G.,Hollfelder, Florian,Spring, David R.
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- Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
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Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is
- Miao, Jianzhuang,Cui, Huaqing,Jin, Jing,Lai, Fangfang,Wen, Hui,Zhang, Xiang,Ruda, Gian Filippo,Chen, Xiaoguang,Yin, Dali
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supporting information
p. 881 - 884
(2015/02/19)
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- Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones
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In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.
- Lu, Tzy-Ming,Ko, Horng-Huey,Ng, Lean-Teik,Hsieh, Yen-Pin
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p. 963 - 979
(2015/06/25)
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- Development of a general approach to the synthesis of a library of isoflavonoid derivatives
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Isoflavonoids are a class of organic compounds that act primarily as antioxidants. They are produced almost exclusively by various members of the bean family including soybeans, tofu, peanuts, chick peas, and alfalfa. The antioxidant characteristics that isoflavonoids exhibit help hinder the progression of certain cancers, primarily breast, prostate, and colon cancer. We have developed a three-five step synthesis for obtaining a suite of isoflavonoid derivatives. The synthesis involves an enamine formation, a ring closure and halogenation, a Suzuki coupling, and finally a global deprotection to obtain the respective isoflavonoid derivatives.
- Biegasiewicz, Kyle F.,Gordon, James S.,Rodriguez, Deana A.,Priefer, Ronny
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p. 5210 - 5212
(2014/12/11)
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- Synthesis and biological evaluation of pyranoisoflavone derivatives as anti-inflammatory agents
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In this paper, barbigerone (1a) and its twenty-seven related structural analogues were synthesized via complementary synthetic routes and their anti-inflammatory effects on the expression of TNF-α in LPS-stimulated splenocytes were evaluated. Among these compounds, 1a, 1d, 1f and 1g were found to remarkably inhibit TNF-α production. Furthermore, 1g showed the most potent and dose-dependent manner inhibitory effect on TNF-α release, with better IC50 value (3.58 μM) than barbigerone (8.46 μM). Oral administration of 1g at 20 mg/kg/day for two weeks obviously demonstrated protective effect in adjuvant-induced arthritis models as evaluated by clinical score of paws, and histological examination of joint tissues from rats. Mechanism studies on mRNA and protein level suggested that 1g inhibited the TNF-α production via depressing TNF-α converting enzyme (TACE) mRNA expression. In conclusion, these data show 1g with potential therapeutic effects as an anti-inflammatory agent.
- Wei, Zhe,Yang, Youzhe,Xie, Caifeng,Li, Chunyan,Wang, Guangcheng,Ma, Liang,Xiang, Mingli,Sun, Jian,Wei, Yuquan,Chen, Lijuan
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p. 172 - 183
(2014/07/21)
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- Design, synthesis, and osteogenic activity of daidzein analogs on human mesenchymal stem cells
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Osteoporosis is caused by an overstimulation of osteoclast activity and the destruction of the bone extracellular matrix. Without the normal architecture, osteoblast cells are unable to rebuild phenotypically normal bone. Hormone replacement therapy with estrogen has been effective in increasing osteoblast activity but also has resulted in the increased incidence of breast and uterine cancer. In this study we designed and synthesized a series of daidzein analogs to investigate their osteogenic induction potentials. Human bone marrow derived mesenchymal stem cells (MSCs) from three different donors were treated with daidzein analogs and demonstrated enhanced osteogenesis when compared to daidzein treatment. The enhanced osteogenic potential of these daidzein analogs resulted in increased osterix (Sp7), alkaline phosphatase (ALP), osteopontin (OPN), and insulin-like growth factor 1 (IGF-1), which are osteogenic transcription factors that regulate the maturation of osteogenic progenitor cells into mature osteoblast cells.
- Strong, Amy L.,Jiang, Quan,Zhang, Qiang,Zheng, Shilong,Boue, Stephen M.,Elliott, Steven,Burow, Matthew E.,Bunnell, Bruce A.,Wang, Guangdi
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p. 143 - 148
(2014/03/21)
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- ISOFLAVONE FATTY ACID ESTER DERIVATIVES, PREPARATION METHOD AND PHARMACEUTICAL USES THEREOF
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Isoflavone fatty acid ester derivatives of formula (I) or (II), the preparation method thereof and the pharmaceutical compositions containing such compounds are disclosed. The uses of such compounds in preparation of medicaments for preventing or treating hyperlipidemia, obesity or type II diabetes are also disclosed.
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Paragraph 0118
(2013/04/10)
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- Novel synthesis of 3-phenyl-chromen-4-ones using n-heterocyclic carbene as organocatalyst: An efficient domino catalysis type approach
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Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.
- Mishra, Priya,Singh, Sarita,Ankit, Preyas,Fatma, Shahin,Singh, Divya,Singh, Jagdamba
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p. 1070 - 1076
(2013/07/28)
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- Synthetic analogs of daidzein, having more potent osteoblast stimulating effect
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A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein.
- Yadav, Dinesh K.,Gautam, Abnish K.,Kureel, Jyoti,Srivastava, Kamini,Sahai, Mahendra,Singh, Divya,Chattopadhyay, Naibedya,Maurya, Rakesh
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p. 677 - 681
(2011/03/18)
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- An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin
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Synthesis of the soy isoflavone, daidzein, and its derivatives, isoformononetin and dimethyldaidzein, through utilization of a novel synthetic pathway is reported. This synthesis employs an enamine addition and O-methylation of 2,4-dihydroxyacetophenone, a subsequent ring closure and iodination, followed by a Suzuki coupling with PEG 10000. Demethylation of either isoformononetin or dimethyldaidzein afforded daidzein.
- Biegasiewicz, Kyle F.,Denis, Jeffrey D. St.,Carroll, Vincent M.,Priefer, Ronny
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experimental part
p. 4408 - 4410
(2010/09/20)
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- Synthesis and biological evaluation of isoflavone fatty acid esters with potential weight loss and hypolipidemic activities
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A series of isoflavone fatty acid esters were designed on the basis of endogenous oleoyl-estrone using estrogen moiety modification strategy. Ten new compounds were synthesized, and their body weight loss and hypolipidemic bioactivities were assayed. Some of these novel compounds could effectively inhibit the differentiation of 3T3-L1 preadipocytes in vitro. The most potent compound 1a significantly decreased the body weight and white adipose tissue weight in a high-fat diet-induced rat model. Also, compound 1a showed good hypolipidemic activity and low toxicity.
- Xiang, Hua,Zhao, Wei,Xiao, Hong,Qian, Lei,Yao, Yao,Li, Xiao-Bo,Liao, Qing-Jiang
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experimental part
p. 3036 - 3042
(2010/07/06)
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- Effects of 7-O substitutions on estrogenic and anti-estrogenic activities of daidzein analogues in MCF-7 breast cancer cells
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Daidzein (1) is a natural estrogenic isoflavone. We report here that 1 can be transformed into anti-estrogenic ligands by simple alkyl substitutions of the 7-hydroxyl hydrogen. To test the effect of such structural modifications on the hormonal activities of the resulting compounds, a series of daidzein analogues have been designed and synthesized. When MCF-7 cells were treated with the analogues, those resulting from hydrogen substitution by isopropyl (3d), isobutyl (3f), cyclopentyl (3g), and pyrano- (2) inhibited cell proliferation, estrogen-induced transcriptional activity, and estrogen receptor (ER) regulated progesterone receptor (PgR) gene expression. However, methyl (3a) and ethyl (3b) substitutions of the hydroxyl proton only led to moderate reduction of the estrogenic activities. These results demonstrated the structural requirements for the transformation of daidzein from an ER agonist to an antagonist. The most effective analogue, 2, was found to reduce in vivo estrogen stimulated MCF-7 cell tumorigenesis using a xenograft mouse model.
- Jiang, Quan,Payton-Stewart, Florastina,Elliott, Steven,Driver, Jennifer,Rhodes, Lyndsay V.,Zhang, Qiang,Zheng, Shilong,Bhatnagar, Deepak,Boue, Stephen M.,Collins-Burow, Bridgette M.,Sridhar, Jayalakshmi,Stevens, Cheryl,McLachlan, John A.,Wiese, Thomas E.,Burow, Matthew E.,Wang, Guangdi
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experimental part
p. 6153 - 6163
(2010/11/02)
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- Daidzein as an antioxidant of lipid: Effects of the microenvironment in relation to chemical structure
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Isoflavone daidzein (D, pKa1 = 7.47 ± 0.02 and pK a2 = 9.65 ± 0.07) was, through a study of the parent compound and its three methyl anisol derivatives 7-methyldaidzein (7-Me-D, pKa = 9.89 ± 0.05), 4'-methyldaidzein (4'-Me-D, pKa = 7.43 ± 0.03), and 7,4'-dimethyldaidzein (7,4'-diMe-D), found to retard lipid oxidation in liposomal membranes through two mechanisms: (i) radical scavenging for which the 4'-OH was more effective than the 7-OH group in agreement with the oxidation potentials: 0.69 V for 4'-OH and 0.92 V for 7-OH versus Ag/AgCl in acidic solution and 0.44 V for 4'-O- and 0.49 V for 7-O- in alkaline solution and (ii) change in membrane fluidity through incorporation of the isoflavones, in effect hampering radical mobility. The radical scavenging efficiency measured by the rate of the reaction with the ABTS?+ in aqueous solution followed the order D > 7-Me-D > 4'-Me-D > 7,4'-diMe-D, as also found for antioxidant efficiency in liposomes when oxidation was initiated with the water-soluble AAPH radical and monitored as the formation of conjugate dienes. For oxidation initiated by the lipid-soluble AMVN radical, the antioxidant efficiency was ranked as 4'-Me-D > D > 7,4'-diMe-D > 7-Me-D, and change in fluorescence anisotropy of fluorescent probes bound to the membrane surface or inside the lipid bilayer confirmed the effects of isoflavones on the membrane fluidity, especially for 7,4'-diMe-D.
- Liang, Jun,Tian, Yu-Xi,Fu, Li-Min,Wang, Tian-He,Li, Hai-Jun,Wang, Peng,Han, Rui-Min,Zhang, Jian-Ping,Skibsted, Leif H.
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experimental part
p. 10376 - 10383
(2010/03/25)
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- Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis
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S-adenosyl-l-methionine: 2-hydroxyisoflavanone 4′-O-methyltransferase (HI4′OMT) methylates 2,7, 4′-trihydroxyisoflavanone to produce formononetin, an essential intermediate in the synthesis of isoflavonoids with methoxy or methylenedioxy groups at carbon 4′ (isoflavone numbering). HI4′OMT is highly similar (83% amino acid identity) to (+)-6a-hydroxymaackiain 3-O-methyltransferase (HMM), which catalyzes the last step of (+)-pisatin biosynthesis in pea. Pea contains two linked copies of HMM with 96% amino acid identity. In this report, the catalytic activities of the licorice HI4′OMT protein and of extracts of Escherichia coli containing the pea HMM1 or HMM2 protein are compared on 2,7,4′-trihydroxyisoflavanone and enantiomers of 6a-hydroxymaackiain. All these enzymes produced radiolabelled 2,7-dihydroxy-4′-methoxyisoflavanone or (+)-pisatin from 2,7,4′-trihydroxyisoflavanone or (+)-6a-hydroxymaakiain when incubated with [methyl-14C]-S-adenosyl-l-methionine. No product was detected when (-)-6a-hydroxymaackiain was used as the substrate. HI4′OMT and HMM1 showed efficiencies (relative Vmax/Km) for the methylation of 2,7,4′-trihydroxyisoflavanone 20 and 4 times higher than for the methylation of (+)-6a-hydroxymaackiain, respectively. In contrast, HMM2 had a higher Vmax and lower Km on (+)-6a-hydroxymaackiain, and had a 67-fold higher efficiency for the methylation of (+)-6a-hydroxymaackiain than that for 2,7,4′-trihydroxyisoflavanone. Among the 15 sites at which HMM1 and HMM2 have different amino acid residues, 11 of the residues in HMM1 are the same as found in HI4′OMTs from three plant species. Modeling of the HMM proteins identified three or four putative active site residues responsible for their different substrate preferences. It is proposed that HMM1 is the pea HI4′OMT and that HMM2 evolved by the duplication of a gene encoding a general biosynthetic enzyme (HI4′OMT).
- Akashi, Tomoyoshi,VanEtten, Hans D.,Sawada, Yuji,Wasmann, Catherine C.,Uchiyama, Hiroshi,Ayabe, Shin-ichi
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p. 2525 - 2530
(2007/10/03)
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- Syntheses and crystal structures of two soybean isoflavone derivatives
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Two soybean isoflavone derivatives, 7-methoxy-4′-hydroxyisoflavone (1) and 4′, 7-diethoxyl-5-hydroxyisoflavone (2) were synthesized and their crystal structures were determined by single-crystal X-ray diffraction. Two derivatives crystallize in the monocl
- Zhang, Zun-Ting,Wang, Qiu-Ya
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p. 679 - 686
(2007/10/03)
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- COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH
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The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.
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Page/Page column 22
(2010/11/30)
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- Synthesis of daidzin analogues as potential agents for alcohol abuse
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Daidzin, the active principle of an herbal remedy for 'alcohol addiction', has been shown to reduce alcohol consumption in all laboratory animals tested to date. Correlation studies using structural analogues of daidzin suggests that it acts by raising the monoamine oxidase (MAO)/mitochondrial aldehyde dehydrogenase (ALDH-2) activity ratio (J. Med. Chem. 2000, 43, 4169). Structure-activity relationship (SAR) studies on the 7-O-substituted analogues of daidzin have revealed structural features important for ALDH-2 and MAO inhibition (J. Med. Chem. 2001, 44, 3320). We here evaluated effects of substitutions at 2, 5, 6, 8, 3′ and 4′ positions of daidzin on its potencies for ALDH-2 and MAO inhibition. Results show that analogues with 4′-substituents that are small, polar and with hydrogen bonding capacities are most potent ALDH-2 inhibitors, whereas those that are non-polar and with electron withdrawing capacities are potent MAO inhibitors. Analogues with a 5-OH group are less potent ALDH-2 inhibitors but are more potent MAO inhibitors. All the 2-, 6-, 8- and 3′-substituted analogues tested so far do not inhibit ALDH-2 and/or have decreased potencies for MAO inhibition. This, together with the results obtained from previous studies, suggests that a potent antidipsotropic analogue would be a 4′,7-disubstituted isoflavone. The 4′-substituent should be small, polar, and with hydrogen bonding capacities such as, -OH and -NH2; whereas the 7-substituent should be a straight-chain alkyl with a terminal polar function such as -(CH 2)n-OH with 2≤n ≤6, -(CH2) n-COOH with 5≤n ≤10, or -(CH2)n-NH 2 with n ≥4.
- Gao, Guang-Yao,Li, Dian-Jun,Keung, Wing Ming
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p. 4069 - 4081
(2007/10/03)
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- The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis
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The yellow intermediate 4f produced during the reaction of the deoxybenzoin 3f with N,N'-dimethyl(chloromethylene)ammonium chloride in the presence of BF3*Et2O prior to the formation of the corresponding isoflavone was isolated for the first time and characterized by NMR, MS and single-crystal X-ray diffraction techniques. These yellow intermediates showed anticancer, nematicidal and mosquitocidal activities.
- Balasubramanian, Sreenivasan,Ward, Donald L.,Nair, Muraleedharan G.
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p. 567 - 570
(2007/10/03)
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- An efficient 'one pot'synthesis of isoflavones
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Initial formation of deoxybenzoin 3 from phenyl acetic acid 1 and phenol 2 in the presence of BF3.Et2O followed by its treatment at room temperature with N, N'-dimethyl (chloromethylene) ammonium chloride, generated by reacting PCl5 with DMF provides a mild and efficient route for a 'one pot' synthesis of Isoflavones in high yields.
- Balasubramanian, Sreenivasan,Nair, Muraleedharan G.
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p. 469 - 484
(2007/10/03)
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- New scheme of the biosynthesis of formononetin involving 2,7,4′-trihydroxyisoflavanone but not daidzein as the methyl acceptor
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Glycyrrhiza echinata cell-free extract produced isoformononetin by the 7-O-transmethylation of daidzein from S-adenosyl-L-methionine (SAM). When the yeast microsome expressing 2-hydroxyisoflavanone synthase was mixed with the cell-free extract and incubated with liquiritigenin and SAM, formononetin emerged. Furthermore, the cell-free extract yielded formononetin on incubation with 2,7,4′-trihydroxyisoflavanone and SAM. We propose a novel pathway of formononetin biosynthesis involving 2,7,4′-trihydroxyisoflavanone as the methyl acceptor.
- Akashi, Tomoyoshi,Sawada, Yuji,Aoki, Toshio,Ayabe, Shin-Ichi
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p. 2276 - 2279
(2007/10/03)
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- ISOFLAVONE O-METHYLTRANSFERASE ACTIVITIES IN ELICITOR-TREATED CELL SUSPENSION CULTURES OF MEDICAGO SATIVA
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Treatment of alfalfa cell suspension cultures with elicitor preparations from baker's yeast or from cell walls of Colletotrichum lindemuthianum resulted in a ca 200-fold induction of isoflavone O-methyltransferase (IOMT) activity.The elicited cultures contained O-methyltransferase activity against isoflavone, isoflavan and pterocarpan substrates.These activities could be separated into two distinct fractions by ion-exchange chromatography.The major IOMT activity (IOMT II) was purified to homogeneity by a combination of anion exchange chromatography, hydrophobic interaction chromatography and chromatofocussing.It is a monomeric enzyme of subunit Mr 41000 which could be photoaffinity labelled with tritiated SAM.IOMT II converted the isoflavone daidzein to its 7-O-methyl ether isoformononetin, with Km values of 20 μM for daidzein and 150 μM for SAM and a pH optimum of 8.5.Both IOMT II and the less abundant IOMT species (IOMT I) exhibited greatest activity with 6,7,4'-trihydroxyisoflavone as methyl acceptor.IOMT I, but not IOMT II, also catalysed the A-ring methylation of the pterocarpan phytoalexin medicarpin.Isoflavone 4'-OMT activity, which is believed necessary for the formation of the B-ring methoxy substituent of medicarpin, was present at very low activity in extracts from the cultures and was only weakly induced by elicitor.Key Word Index - Medicago sativa; Leguminosae; isoflavone 7-O-methyltransferase; phytoalexin biosynthesis
- Edwards, Robert,Dixon, Richard A.
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p. 2597 - 2606
(2007/10/02)
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- INDUCIBLY-FORMED ISOFLAVONOIDS FROM LEAVES OF SOYBEAN
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Isoformononetin, glyceollins I, II and III, and 2-isopentenyl-3,6α,9-trihydroxypterocarpan (glyceocarpin) accumulated in soybean (Glycine max) leaves after treatment with aqueous sodium iodoacetate or a cell suspension of the bacterium, Pseudomonas pisi.These compounds were also accompanied by two previously unreported pterocarpans, glycerofuran and its 9-O-methyl derivative.Glyceocarpin is described for the first time as a plant product.Key Word Index- Glycine max; Leguminosae; soybean; Pseudomonas pisi; isoflavonoids; pterocarpans; isoflavone; phytoalexins; antibacterial activity.
- Ingham, John L.,Keen, Noel T.,Mulheirn, Lawrence J.,Lyne, Robert L.
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p. 795 - 798
(2007/10/02)
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