hydrolysis of Scutellarin and Related Glycosides to Scutellarein and the Corresponding Aglycones

Zhang, Wei; Yi, Dong; Gao, Kai; Liu, Manshuo; Yang, Jian; Liao, Xiali; Yang, Bo

doi:10.3184/174751914x14017253941699

Cited by 15 publications

(13 citation statements)

References 22 publications

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“…We have reported the synthesis of luteolin from 1,3,5-trimethoxybenzene using two routes in 47% and 32% yield, respectively. 26 As a continuation of our investigations on the synthesis of the bioactive natural flavonoids and their biological activities, 26,[27][28][29][30][31][32][33][34][35][36] we have carried out further studies and we now report the preparation of luteolin 1 using easily available starting materials, and by an improved procedure with satisfactory yields. JOURNAL OF CHEMICAL RESEARCH 2015 551 temperature apparatus, 1 H NMR spectral data were recorded on a Bruker Avance 400 NMR spectrometer or a Bruker DRX 500 NMR spectrometer, chemical shifts were reported in ppm against internal tetramethylsilane.…”

Section: Methodsmentioning

confidence: 99%

Modified Syntheses of the Dietary Flavonoid Luteolin

Wang

Liu

et al. 2015

Journal of Chemical Research

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Two novel syntheses of the flavone luteolin are described. In the first, 3,5-dimethoxyphenol was converted to 2-hydroxy-4,6-dimethoxyacetophenone and then by condensation with 3,4-dimethoxybenzaldehyde to 2′-hydroxy-3,4,4′,6′-tetramethoxychalcone. In the second, the chalcone step was prepared in which 3,5-dimethoxyphenol was acylated with 3,4-dimethoxycinnamoyl chloride. The chalcone was then cyclised with iodine and demethylated with pyridine hydrochloride to form luteolin in 47% and 40% overall yield, respectively. Several disadvantages of previous syntheses like long reaction time, harsh reaction conditions and low overall yield have been overcome.

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Section: Methodsmentioning

confidence: 99%

Modified Syntheses of the Dietary Flavonoid Luteolin

Wang

Liu

et al. 2015

Journal of Chemical Research

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“…The hydrolysis reaction with concentrated sulfuric acid(VI) and water was used to obtain wogonin (4) and baicalein (3) according to Zhang et al [28]. The authors hydrolyzed a series of glycosylated flavones including baicalin (1) as substrates to obtain their aglycones; however, wogonoside (2) was not used in that study.…”

Section: Hydrolysis Of Dried Powdered Baikal Skullcap Rootmentioning

confidence: 99%

“…The hydrolysis reaction was carried out according to the method proposed by Zhang et al [28], with modifications. Thus, 1 g of dried, powdered baikal skullcap was placed in a 100 mL round bottom flask and dissolved supported by sonication with 10 mL of sulfuric acid(VI) at room temperature.…”

Section: Chemistry Hydrolysis Of Dry Powdered Baikal Skullcapmentioning

confidence: 99%

Simple and Rapid Method for Wogonin Preparation and Its Biotransformation

Tronina

Mrozowska

Bartmańska

et al. 2021

IJMS

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Wogonin is one of the most active flavonoids from Scutellaria baicalensis Georgi (baikal skullcap), widely used in traditional Chinese medicine. It exhibits a broad spectrum of health-promoting and therapeutic activities. Together with baicalein, it is considered to be the one of main active ingredients of Chinese medicines for the management of COVID-19. However, therapeutic use of wogonin may be limited due to low market availability connected with its low content in baikal skullcap and lack of efficient preparative methods for obtaining this compound. Although the amount of wogonin in skullcap root often does not exceed 0.5%, this material is rich in wogonin glucuronide, which may be used as a substrate for wogonin production. In the present study, a rapid, simple, cheap and effective method of wogonin and baicalein preparation, which provides gram quantities of both flavonoids, is proposed. The obtained wogonin was used as a substrate for biotransformation. Thirty-six microorganisms were tested in screening studies. The most efficient were used in enlarged scale transformations to determine metabolism of this xenobiotic. The major phase I metabolism product was 4′-hydroxywogonin—a rare flavonoid which exhibits anticancer activity—whereas phase II metabolism products were glucosides of wogonin. The present studies complement and extend the knowledge on the effect of substitution of A- and B-ring on the regioselective glycosylation of flavonoids catalyzed by microorganisms.

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“…We have reported the synthesis of naringenin in five steps from 1,3,5-trimethoxybenzene or phloroglucinol with a moderate overall yield. 17 As a continuation of our investigations on the synthesis of the bioactive natural flavonoids and their biological activity, 17,[18][19][20][21][22][23][24][25] we have carried out further studies and we now report the preparation of 1 using commercially available starting materials, and by an improved procedure with satisfactory yields.…”

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confidence: 99%

Practical Synthesis of Naringenin

Wang

Yang

Zhang

et al. 2015

Journal of Chemical Research

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Two routes for the synthesis of the flavanone naringenin are described. In the first, 3,5-dimethoxyphenol is converted to 2-hydroxy-4,6-dimethoxyacetophenone and then by condensation with anisaldehyde to 2′-hydroxy-4,4′,6′-trimethoxychalcone. The chalcone is then cyclised with aqueous hydrochloric acid and demethylated with pyridine hydrochloride to form naringenin in 45% overall yield. The condensation of 2-hydroxy-4,6-dimethoxyacetophenone with anisaldehyde could also directly produce 4′,5,7-trimethoxyflavanone, which was then converted into naringenin in 60% overall yield. In the second route, a single step for the preparation of the chalcone is used in which 1,3,5-trimethoxybenzene is acylated with p-methoxycinnamic acid. Although the synthesis of naringenin is achieved in a lower overall yield of 29%, the process is simpler.

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hydrolysis of Scutellarin and Related Glycosides to Scutellarein and the Corresponding Aglycones

Cited by 15 publications

References 22 publications

Modified Syntheses of the Dietary Flavonoid Luteolin

Modified Syntheses of the Dietary Flavonoid Luteolin

Simple and Rapid Method for Wogonin Preparation and Its Biotransformation

Practical Synthesis of Naringenin

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