Preparation and Taste of Certain Glycosides of Flavanones and of Dihydrochalcones

Esaki, Sachiko; Nishiyama, Kiyotoshi; Sugiyama, Naoko; Nakajima, Ryuta; Takao, Yoshihiro; Kamiya, Shintaro

doi:10.1271/bbb.58.1479

Cited by 19 publications

(8 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The selective glycosylation of the most acidic C7-OH group can be performed by protected glycosylbromide activated by silver carbonate (Oyama and Kondo, 2004). With some modifications, this method is still in use not only for glycosylation of phenolic compounds (Esaki et al, 1994) but also for glucuronidation (Moon et al, 2001). A simple route to flavanone 7-O-b-D-glucoside is the partial hydrolysis of naringin and hesperidin using formic acid in cyclohexanol.…”

Section: Glycosidesmentioning

confidence: 99%

A comprehensive review on flavanones, the major citrus polyphenols

Khan

Zill-e-Huma

Dangles

2014

Journal of Food Composition and Analysis

371

242

View full text Add to dashboard Cite

The consumption of Citrus fruits and juices has been widely investigated for its possible role in the prevention of cardiovascular disease and cancer. These beneficial effects are mainly attributed to flavanones, the typical polyphenols of Citrus species. Major flavanones in plant species include hesperetin, naringenin, eriodictyol, isosakuranetin and their respective glycosides. Hesperetin and its derivatives are characteristic flavanones of sweet orange, tangelo, lemon and lime, while naringenin and its derivatives are those of grapefruit and sour orange. Advances in analytical techniques like ultra high performance liquid chromatography (UPLC) coupled with mass spectrometry has facilitated (a) the estimation of flavanone contents in other plant species and in humans after ingestion and (b) the determination of flavanone metabolites more rapidly and with greater efficiency. The present review will summarize the current knowledge about flavanones from their occurrence in plants to the bioactivity of their metabolites in humans.

show abstract

Section: Glycosidesmentioning

confidence: 99%

A comprehensive review on flavanones, the major citrus polyphenols

Khan

Zill-e-Huma

Dangles

2014

Journal of Food Composition and Analysis

371

242

View full text Add to dashboard Cite

show abstract

“…4 Therefore, it is not surprising that many synthetic methods have been developed for these types of compounds. [5][6][7][8][9][10][11] Evelynin B and taccabulin D (Fig. 1) are two novel retrodihydrochalcone-typed compounds, isolated from fresh roots and rhizomes of Tacca chantrieri and T. integrifolia by Moberry and co-workers in 2013.…”

mentioning

confidence: 99%

Total Synthesis of Evelynin B and Taccabulin D

Huang

Gan

Guo

2015

Journal of Chemical Research

View full text Add to dashboard Cite

Biosynthetic retro-dihydrochalcone derivatives represent a significant class of compounds with broad and remarkable potential biological properties, such as anti-ulcer, 1 antihistamine, 2 and anti-microbial, 3 and anti-malarial activities. 4 Therefore, it is not surprising that many synthetic methods have been developed for these types of compounds. [5][6][7][8][9][10][11] Evelynin B and taccabulin D (Fig. 1) are two novel retrodihydrochalcone-typed compounds, isolated from fresh roots and rhizomes of Tacca chantrieri and T. integrifolia by Moberry and co-workers in 2013. 12 Compounds 1 and 2 have antiproliferative activities against three cancer cell lines: HeLa, A549 and PC-3. 12 The IC 50 values of evelynin B (1) against HeLa, A549, and PC-3 cells are 8.8, 8.3 and 5.0 μM, respectively, while those of taccabulin D (2) are 28.9, 40.3 and more than 50 μM.We have initiated the total synthesis of the two new compounds in order to investigate the potential bioactivity of the derivatives. We now report the concise efficient total syntheses of evelynin B (1) and taccabulin D (2) from the accessible starting material trimethoxybenzene which would provide enough compounds for further biological studies. Results and discussionOur initial retrosynthetic analysis of 1 is outlined in Scheme 1. We envisaged that a Claisen-Schmidt reaction could be used to construct the main skeleton of evelynin B and taccabulin D. Aldehyde 6, in turn, could be obtained from a cheap starting material 1,2,3-trimethoxybenzene.The synthesis of evelynin B is illustrated in Scheme 2. 1,2,3-Trimethoxybenzene was oxidised with 30% HNO 3 to form 1,4-benzoquinone 3 in 80% yield. 13 Reduction of 3 with Na 2 S 2 O 4 in EtOAc for 40 min smoothly gave diphenol 4 in 84% yield. 14 Dialkylation of diphenol 4 with BnBr in refluxing acetone affords ether 5 in 86% yield. 15 Aldehyde 6 was available through Vilsmeier reaction from ether 5 in 81% yield. 14 Then, aldehyde 6 was reacted with 3,4-methylenedioxyacetophenone 7 through

show abstract

“…Partial hydrolysis of NDG by b-glucosidase treatment suggested that compound 2 was the monoglucoside of naringenin, and it was finally confirmed as naringenin 4Ј-O-b-D-glucopyranoside by the comparison of 1 H NMR and FABMS spectral data of the partial hydrolysate with the authentic data (Esaki et al 1994). In the bglucosidase treatment, the formation of naringenin 7-Ob-D-glucopyranoside (Saito et al 1994) was also detected.…”

Section: Resultsmentioning

confidence: 96%

“…It was noteworthy that compound 1 was easily racemized when kept in DMSO, and in repeated 1 H NMR analyses, the doublet signal assigned to the anomeric proton of the glucose bound to 7-OH (d H 4.98 and 4.97, Jϭ7.5 Hz) was changed to the broad triplet (d H 4.98, 4.96 and 4.93, Jϭ7.5 Hz) presumably owing to the racemization at C-2. The trace signal at d H 4.93 was also observed in the first 1 H NMR analysis, suggesting that compound 1 isolated in the present study contained a small amount of (2S)-derivative, although its optical purity was not determined.Partial hydrolysis of NDG by b-glucosidase treatment suggested that compound 2 was the monoglucoside of naringenin, and it was finally confirmed as naringenin 4Ј-O-b-D-glucopyranoside by the comparison of 1 H NMR and FABMS spectral data of the partial hydrolysate with the authentic data (Esaki et al 1994). In the bglucosidase treatment, the formation of naringenin 7-Ob-D-glucopyranoside (Saito et al 1994) was also detected.…”

mentioning

confidence: 96%

Metabolism of administered (2RS)-naringenin in flavonoid-producing cultured cells of Sophora flavescens

Yamamoto

Kuribayashi

Seshima

et al. 2004

Plant Biotechnology

View full text Add to dashboard Cite

Cultured cells of Sophora flavescens produce (2S)-naringenin-derived prenylated flavanone sophoraflavanone G and liquiritigenin-derived trifolirhizin 6Ј-O-malonate. The regulation of flavonoid biosynthesis was examined by analyzing the metabolites produced in the cultured cells fed (2RS)-naringenin. The amount of sophoraflavanone G in cells fed 0.1 or 0.3 mM (2RS)-naringenin was two-fold that in control cells, although the conversion ratio was only 5 to 10% of the administered (2S)-naringenin. On the other hand, (2R)-naringenin, which does not occur naturally, was efficiently converted into its 4Ј,7-di-O-b-D-glucoside. (2S)-Naringenin prenylation activity was higher at the logarithmic growth stage. The cells fed (2RS)-naringenin at a lower concentration (below 0.1 mM), accumulated sophoraflavanone G as the main prenylated flavanone. In contrast, cells fed 0.3 mM (2RS)-naringenin accumulated 8-prenylnaringenin and leachianone G, intermediates of sophoraflavanone G in large amounts. Accumulation of trifolirhizin 6Ј-O-malonate was suppressed by the addition of naringenin.Key words: Naringenin; (2R)-naringenin 4Ј,7-di-O-b-D-glucoside; Sophora flavescens; sophoraflavanone G. Original PaperCopyright © 2004 The Japanese Society for Plant Cell and Molecular Biology precursor of SFG but not TM, to the culture medium, and examined its effect on the production of these secondary metabolites. Materials and methods General(2RS)-Naringenin was purchased from Nacalai Tesque (Kyoto, Japan). HPLC-photodiode array analysis was carried out using a Waters Alliance PDA system (Tokyo, Japan). 1 H and 13 C NMR spectra were recorded in DMSO-d 6 with spectrometers (Varian Unity plus 500 and Varian Gemini 300) operating at 500 MHz and 300 MHz for 1 H, and 125 MHz for 13 C, respectively. Mass spectra were recorded on a JEOL JMS DX-303 spectrometer. UV and CD spectra were measured with a UV-1600 visible spectrophotometer and a J-725N spectrometer, respectively. Plant materials and culture methodsThe origin and subculturing of callus cultures (Yamamoto et al. 1991a) and the establishment of cell suspension cultures (Yamamoto et al. 1996) of S. flavescens were described previously. Cell suspension cultures (0.5 g) were subcultured in 100 ml-flasks containing 20 ml of Murashige and Skoog (1962) medium with 1 mM 2,4-D and 1 mM kinetin at 14 days interval on a rotary shaker at a speed of 100 rpm in the dark at 25°C. For the experiment, filter-sterilized 300 mM (2RS)-naringenin solution in 20 ml of DMSO was aseptically added to the flask (final concentration 0.3 mM), and cultured for another one day. Twenty ml of DMSO was added to the control cells. Isolation and identification of the metabolitesThe naringenin-fed cells collected from 60 flasks (120 g) were extracted three times with MeOH by ultrasonication in ice-water bath for 30 min. The MeOH extract after concentration was resuspended in H 2 O, partitioned with CHCl 3 and n-BuOH, successively. The residual H 2 O layer was passed through Diaion HP-20 column (Mitsubishi Chem, Tokyo, J...

show abstract

Preparation and Taste of Certain Glycosides of Flavanones and of Dihydrochalcones

Cited by 19 publications

References 9 publications

A comprehensive review on flavanones, the major citrus polyphenols

A comprehensive review on flavanones, the major citrus polyphenols

Total Synthesis of Evelynin B and Taccabulin D

Metabolism of administered (2RS)-naringenin in flavonoid-producing cultured cells of Sophora flavescens

Contact Info

Product

Resources

About