- A new strategy for isoflavone C-glycoside synthesis: The total synthesis of puerarin
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Given that C-glucosylisoflavones often possess promising biological activities, the development of an efficient synthetic method for this type of molecules is useful for drug discovery. Accordingly, a highly efficient five-step strategy was developed for the total synthesis of puerarin, an isoflavone C-glycoside. An alkyl substituent 4-CH3OC6H4CH2CH2 with an electron-donating group on the aromatic ring was used to enhance the reactivity of phenol and the regioselectivity of O-C rearrangement of phenol glycoside. Thus, coupling of the ethylbenzene derivative of a phenol 1c with glycosyl trifluoroacetimidate 2 resulted in C-glycoside 3c in a 46.2% yield, which was easily de-tert-butylated with trifluoroacetic acid and oxidized with 2,3-dicyano-5,6-dichlorobenzoquinone to produce deoxybenzoin 5. The ring closure reaction of 5 followed by deprotection gave puerarin. This new synthetic strategy is also suitable for the total synthesis of other C-glucosylisoflavones.
- Zou, Yunpeng,Peng, Tao,Wang, Gang,Wen, Xiaoxue,Liu, Shuchen,Sun, Yunbo,Zhang, Shouguo,Gao, Yue,Wang, Lin
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- Isolation of two new C-glucofuranosyl isoflavones from Pueraria lobata (Wild.) Ohwi with HPLC-MS guiding analysis
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A profiling analysis of the total isoflavone extract of the root of Pueraria lobata (Wild.) Ohwi was performed using HPLC coupled with ESI-ion trap mass spectrometry. A total of seven isoflavones were identified according to their retention times, UV, MS data, and comparing with the literature data. Among them, two proposed new compounds were isolated and their structures were determined to be 8-C-α-glucofuranosyl-7,4'-dihydroxyisoflavone and 8-C-β-glucofuranosyl-7,4'-dihydroxyisoflavone, named as neopuerarin A (7) and neopuerarin B (6), on the basis of chemical and spectral analyses.
- Zhang, Hai-Jiang,Yang, Xiao-Ping,Wang, Kui-Wu
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- Isoflavone glucosides exist as their 6''-O-malonyl esters in Pueraria lobata and its cell suspension cultures
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Methanol extracts prepared by mild and careful procedure from cultured cells of P. lobata were analyzed by reverse phase high performance liquid chromatography (HPLC) to reveal that most of the isoflavone 7-O-glucosides daidzin(1) and genistin(2), and 8-C-glucoside puerarin(3), exiost as their 6''-O-malonyl esters. The presence of malonyl esters of 1, 2 and 3 was also detected in the fresh roots and stems of P. lobata.
- Park,Hakamatsuka,Noguchi,Sankawa,Ebizuka
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- Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds
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Chemical treatment of diabetes mellitus is widely studied and controlling of blood glucose level is the main course of therapy. In type 2 diabetes mellitus, insulin resistance is the major problem. An isoflavone C-glucoside, puerarin (1), is known to enhance glucose uptake into the insulin sensitive cell and is thought to be a candidate for treatment of diabetes mellitus. We synthesized 1 and several derivatives to apply for the structure-activity relationship study. The result against 3T3-L1 adipocyte indicated that the C-glucoside part of 1 is unconcerned in its activity when tested in vitro and the main structure responsible for its activity was the isoflavone moiety.
- Kato, Eisuke,Kawabata, Jun
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supporting information; experimental part
p. 4333 - 4336
(2010/09/18)
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- Synthesis of tritium-labeled puerarin - A potential antidipsotropic agent
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Puerarin 1 (8-β-D-Glucopyranosyl-4′-7-dihydroxyisoflavone, NPI-031G) is the major isoflavone C-glycoside isolated from Pueraria lobata, a traditional Chinese medicine widely used for the treatment of alcohol intoxication. In order to understand the mode of action of puerarin in the reward pathway of the central nervous system and to study its bioavailability and pharmacokinetics, we developed a synthetic route for the preparation of tritium-labeled puerarin. The key intermediate 4 was obtained by trimethylsilyl protection of all hydroxyl groups followed by selective deprotection. The corresponding aldehyde 5 was obtained through the subsequent oxidation of the primary alcohol. Standard NaB[3H]4 reduction and hydrolysis produced the tritium-labeled puerarin 6. Copyright
- Lee,Ji,Zhang
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p. 702 - 705
(2008/02/11)
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- Total synthesis of puerarin, an isoflavone C-glycoside
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We completed the first total synthesis of puerarin (1), an isoflavone C-glycoside. The key intermediate, β-D-glucopyranosyl-2,6-dimethoxybenzene (9), was obtained by coupling of a lithiated aromatic reagent (3) with pyranolactone (2) in 56% yield. Condensation of (16) with p-methoxybenzaldehyde gave the chalcone (17). The protected chalcone (18) was cyclized to (19) in the presence of Tl(NO3)3. Demethylation of (19) was accomplished by refluxing with TMSI in CH3CN to give puerarin (1).
- Lee, David Y. W.,Zhang, Wu-Yan,Karnati, Vishnu Vardhan R.
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p. 6857 - 6859
(2007/10/03)
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