- An efficient, scalable approach to hydrolyze flavonoid glucuronides via activation of glycoside bond
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Hydrolyzing flavonoid glucuronides into corresponding aglycones posed some significant challenges. To improve acid-catalyzed hydrolysis process of flavonoid glucuronide, structures of glucuronide, hydrolysis parameters and post-processing were optimized. The optimized condition was performed by hydrolysis flavonoid glycoside methyl ester in a mixed solvent consisting of 2?mol/L H2SO4/EtOH/H2O (1/8/1, v/v/v) at 95?°C for 7?h and resulted in up to 90% aglycone yields, minimal byproduct formations and milder hydrolysis conditions. Furthermore, the optimized method avoids tedious purification steps and is easily conducted on a relatively large-scale using economical and commercially available reagents.
- Jiang, Xue-Yang,Li, Xin-Chen,Liu, Wen-Yuan,Xu, Yun-Hui,Feng, Feng,Qu, Wei
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p. 1895 - 1903
(2017/03/11)
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- A Practical and Efficient Approach to the Preparation of Bioactive Natural Product Wogonin
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A scalable and practical route to wogonin, a bioactive natural product with multiple pharmacological activities which is currently under phase I/II clinical studies, is described. Wogonin was obtained via a four-step process starting from commercially ava
- Li, Tinghan,Weng, Tianwei,Wang, Jubo,Wei, Zhihui,Zhao, Lu,Li, Zhiyu
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p. 171 - 176
(2017/02/26)
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- Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation
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Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.
- Yamashita, Yasunobu,Biard, Alan,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi
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p. 1279 - 1284
(2017/06/27)
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- Synthesis, evaluation and quantitative structure–activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents
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A novel series of 49 wogonin derivatives were synthesized by introducing group at 7-, 8- or B ring of wogonin. The cytotoxic activities against HepG2, A549 and BCG-823 cancer cell lines were also investigated in vitro. Several of them showed obvious cytotoxic activities and compound 3h possessed the highest potency against HepG2, A549, and BCG-823 with IC50 values of 1.07 μM, 1.74 μM and 0.98 μM, respectively. A quantitative structure-activity relationship (QSAR) study of these synthetic derivatives as well as wogonin indicated that high solubility and low octanol/water partition coefficient are favorable, and excessive electrostatic properties and refractivity are unfavorable for the cytotoxic activities of these wogonin derivatives. These findings and results provide a base for further investigations.
- Bian, Jinlei,Li, Tinghan,Weng, Tianwei,Wang, Jubo,Chen, Yu,Li, Zhiyu
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p. 1012 - 1016
(2017/09/30)
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- Preparation method and intermediates of flavonoids
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The invention discloses a preparation method and intermediates of flavonoids. The preparation method comprises the following steps: in a solvent, in the presence of an acid, performing a ring-opening reaction and an elimination reaction on a compound 8 to obtain a compound 9. Raw materials used in the method are easy to acquire, and the method has high yields and simple post processes, and does not need column chromatography.
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Paragraph 0241; 0243-0245
(2017/11/16)
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- Preparation method of flavonoids
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The invention discloses a preparation method of flavonoids. The method comprises the following step: in a solvent, in the presence of iodine and a silver salt or in the presence of iodine and a copper salt, performing an iodination reaction on a compound 1 to obtain a compound 2. Raw materials used in the method are easy to acquire, and the method has high yields and simple post processes, and does not need column chromatography.
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Paragraph 0241-0245
(2017/11/16)
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- A new domino oxidation—rearrangement of 2,3-dihydrowogonin to negletein
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We report an expeditious, iodine-catalysed oxidation of 2,3-dihydrowogonin to negletein which comprises a Wessely–Moser rearrangement (WMR), associated not with an O-demethylation, as usual, but with an oxygen to oxygen methyl shift. In contrast, DDQ in 1
- Spoerlein-Guettler, Cornelia,Milius, Wolfgang,Obenauf, Johannes,Schobert, Rainer
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p. 1560 - 1562
(2018/03/29)
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- Methods of synthesizing flavonoids and chalcones
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Simple and efficient total syntheses of flavonoids including baicalein, oroxylin A and wogonin are described herein. Simultaneous syntheses of oroxylin A and wogonin are also described.
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- Novel synthesis of flavonoids of Scutellaria baicalensis Georgi.
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A concise and efficient total synthesis of the flavonoids baicalein, oroxylin A and wogonin was described. Intramolecular oxidative cyclization followed by demethylation of chalcone 1, readily prepared from trimethoxyphenol, afforded, depending upon the controlled conditions, baicalein or oroxylin A in excellent yields. Demethylation of 1 yielded 3, which, by oxidation with I(2)/dimethyl sulfoxide (DMSO), was readily converted to oroxylin A and wogonin after column chromatography.
- Huang, Wen-Hsin,Chien, Pei-Yu,Yang, Ching-Huey,Lee, An-Rong
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p. 339 - 340
(2007/10/03)
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- Insect antifeedant activity of flavones and chromones against Spodoptera litura
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The antifeedant polymethylated flavones 5-hydroxy-3,6,7,8,4′-heptamethoxyflavone, 5-hydroxy-3,6,7,8-tetramethoxyflavone, and 5,6-dihydroxy-3,7-dimethoxyflavone have been isolated from the cudweed, Gnaphalium affine D. Don (Compositae). These flavonoids and authentic analogues showed insect antifeedant activity against the common cutworm (Spodoptera litura F.). In a previous paper, it was suggested that there was no substituent on the B-ring of the flavonoid for the beneficial antifeedant activity against the common cutworm. These flavonoids having a phenyl group as the B-ring and the chromone as elimination of the B-ring from the flavonoids were used to test the hypothesis of the previously described B-ring effect. The known fact is that Sculletaria baicarensis (Rutaceae) produced the 2-phenyl flavone. Test compounds and their methylated derivatives were prepared from this material for the structure-activity relationship (SAR) study of insect antifeedant activity. In spite of the 2-phenyl flavonoids, some tested compounds did not show any insect antifeedant activity against the common cutworm, although these inactive flavonoids were deficient in the 6-substituent group on the A-ring of the flavonoid. This 6-position-substituted derivative almost showed strong insect antifeedant activity against common cutworm. Moreover, the tested flavonoids having a hydroxyl group as a substituent on any of the positions tended to increase the activity. These results suggested the importance of the 6-position substitution on the flavonoid; however, hydrophilic substituents decreased the activity. Baicalein (5,6,7-trihydroxyflavone) derivatives did not show any activity despite having the 6-substituent derivative. Although the activity of some chromones increased the activity of the flavone, the bulky B-ring was a disadvantage for the antifeedant activity. It was suggested that the charge on C(3) and C(5) of the flavonoid was important for the biological activity. Additionally, an adequate hydrogen bonding property, which is different from lipophilicity, was an advantage for the activity on the basis of a QSAR analysis.
- Morimoto, Masanori,Tanimoto, Kumiko,Nakano, Sachiko,Ozaki, Takayoshi,Nakano, Ayako,Komai, Koichiro
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p. 389 - 393
(2007/10/03)
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