Tannins of rosaceous plants. VIII. Hydrolyzable tannin monomers having a valoneoyl group from flower petals of Rosa rugosa Thunb.

Hatano, Tsutomu; Ogawa, Naoya; Yasuhara, Taeko; Okuda, Takuo

doi:10.1248/cpb.38.3308

Cited by 39 publications

(32 citation statements)

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“…The crude product was dissolved in 1 M hydrochloric acid and purified by CC (500 mg of Sephadex LH-20, H 2 O to MeOH) to afford 2 (9.2 mg, 97% yield) as a pale yellow syrup. 1 H NMR, 13 C NMR, HRMS and optical rotation data for 2 were in agreement with those previously reported 57 .…”

Section: Synthesis Of Compound 44supporting

confidence: 91%

“…After the general drying procedure, the resulting residue was purified by CC (500 mg of SiO 2 , n-hexane/EtOAc ¼ 5/1 to 1/2) to afford 48 (3.6 mg, 53% yield) as a pale yellow syrup. 1 H NMR and optical rotation data for 48 were identical to those previously reported 57 .…”

Section: Synthesis Of Compound 44supporting

confidence: 78%

“…7). Therefore, we identified the product after full methylation of synthesized 2; the 1 H NMR spectrum of fully methylated 48 was identical to that previously reported 57 (Supplementary Table 6). …”

Section: Strategysupporting

confidence: 75%

“…1), an ellagitannin bearing a valoneoyl group. This ellagitannin was isolated from Rosa rugosa THUNB and characterized by Okuda et al 57 The synthesis commenced with the preparation of 1,2,3-tri-Ogalloylated b-D-glucose 36 (Fig. 6).…”

Section: Strategymentioning

confidence: 99%

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A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

et al. 2014

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Ellagitannins are a family of polyphenols containing more than 1,000 natural products. Nearly 40% of these compounds contain a highly oxygenated diaryl ether that is one of the most critical elements to their structural diversity. Here, we report a unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins. The strategy involves oxa-Michael addition of phenols to an orthoquinone building block, with subsequent elimination and reductive aromatization. The design of the building block-a halogenated orthoquinone monoketal of gallal-reduces the usual instability of orthoquinone and controls addition/elimination. Reductive aromatization is achieved with perfect chemoselectivity in the presence of other reducible functional groups. This strategy enables the synthesis of different diaryl ethers. The first total synthesis of a natural ellagitannin bearing a diaryl ethers is performed to demonstrate that the strategy increases the number of synthetically available ellagitannins.

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Section: Synthesis Of Compound 44supporting

confidence: 91%

Section: Synthesis Of Compound 44supporting

confidence: 78%

Section: Strategysupporting

confidence: 75%

Section: Strategymentioning

confidence: 99%

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A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

et al. 2014

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“…The known compounds were identified by comparing their physical and spectroscopic data with previously reported data. [-anomer:  6.67 (H-3), 6.23 (H-3'), 7.14 (H-6"); -anomer:  6.71 (H-3), 6.24 (H-3'), 7.14 (H-6")] was suggested by comparison of the 1 H and 13 C NMR signals with those of rugosin A (1,2,3-tri-O-galloyl-4,6-(S)-valoneoyl-β-D-glucose) (Hatano et al, 1990) (Gupta et al, 1982;Hatano et al, 1990). This was confirmed by HMBC correlations of H-4 (-anomer: 4.81, -anomer: 4.87) and H-6 signals (-anomer: 5.06, 3.62; -anomer: 5.09, 3.69) with valoneoyl-7 ( 168.4) and valoneoyl-7' ( 168.3) ester carbonyls (Fig.…”

Section: Resultsmentioning

confidence: 99%

Two new phenolic glucosides and an ellagitannin from the leaves of Castanopsis sclerophylla

Huang

Tanaka

Matsuo

et al. 2012

Phytochemistry Letters

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Combined chromatographic strategy based on macroporous resin, high‐speed counter‐current chromatography and preparative HPLC for systematic separation of seven antioxidants from the fruit of Terminalia billerica

Yang

Shen

et al. 2019

J of Separation Science

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In the present study, combined chromatographic strategy based on macroporous resin, high-speed counter-current chromatography and preparative high-performance liquid chromatography for systematic separation of antioxidants from crude samples guided by high-performance liquid chromatography with 1,1-diphenyl-2-picrylhydrazyl has been successfully established. Based on this strategy, seven antioxidants including isorugosin A, β -1,2,3,6-tetragalloyl-D-glucose, chebulinic acid, 1,2,3,4,6-penta-Ogalloylβ -D-glucose, chebulagic acid, ethyl gallate, and gallic acid were obtained from the fruit of Terminalia billerica. First, high-performance liquid chromatography with 1,1-diphenyl-2-picrylhydrazyl experiment showed the presence of seven main antioxidants in the crude extract of the fruit of Terminalia billerica. Then, a macroporous resin column chromatography method was developed for the enrichment of these seven antioxidants. Finally, an efficient method based on high-speed counter-current chromatography and preparative high-performance liquid chromatography was developed for the separation of these antioxidants. In the selection of solvent systems, it was found that acetic acid could be a good regulator for modifying the partition coefficient values of tannins. The present study provides a reference for systematic separation of antioxidants from crude samples. Considering the general existence of antioxidants in crude samples, this combined chromatographic strategy might lead to broader application prospects. K E Y W O R D Santioxidants, macroporous resin, systematic separation, Terminalia bellirica, traditional Chinese medicine

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Tannins of rosaceous plants. VIII. Hydrolyzable tannin monomers having a valoneoyl group from flower petals of Rosa rugosa Thunb.

Cited by 39 publications

References 0 publications

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins

Two new phenolic glucosides and an ellagitannin from the leaves of Castanopsis sclerophylla

Combined chromatographic strategy based on macroporous resin, high‐speed counter‐current chromatography and preparative HPLC for systematic separation of seven antioxidants from the fruit of Terminalia billerica

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