Application of 1H-NMR spectroscopy to validation of berberine alkaloid reagents and to chemical evaluation of Coptidis Rhizoma

Hasada, Keiko; Yoshida, Toshihide; Yamazaki, Takeshi; Sugimoto, Naotoshi; Nishimura, Takuya; Nagatsu, Akito; Mizukami, Hajime

doi:10.1007/s11418-010-0490-x

Cited by 30 publications

(16 citation statements)

References 13 publications

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“…Furthermore, qHNMR spectroscopy is rapid and non-invasive, and in most cases it does not require laborious sample pre-cleaning steps. 11) In the present investigation, we demonstrated that qHNMR spectroscopy can be effectively applied for the quantitative determination of carthamin in commercial preparations of Carthamus Red without an authentic carthamin sample.…”

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confidence: 59%

“…NMR spectroscopy acquisition and processing were performed as previously described. 11) In brief, eight scans were performed for each sample with a 90° pulse and a 30-s pulse delay because high precision qHNMR spectra can be achieved when the pulse angle is 90° and the pulse delay time is greater than the quintuple spin-lattice relaxation time (>5*T 1 ). The chemical shifts are given as δ values (ppm) relative to the internal standard HMD.…”

Section: Methodsmentioning

confidence: 99%

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Quantitative Determination of Carthamin in Carthamus Red by <sup>1</sup>H-NMR Spectroscopy

Yoshida

Terasaka

Kato

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Carthamus Red is a food colorant prepared from the petals of Carthamus tinctorius (Asteraceae) whose major pigment is carthamin. Since an authentic carthamin standard is difficult to obtain commercially for the preparation of calibration curves in HPLC assays, we applied 1 H-NMR spectroscopy to the quantitative determination of carthamin in commercial preparations of Carthamus Red. Carthamus Red was repeatedly extracted in methanol and the extract was dissolved in pyridine-d 5 containing hexamethyldisilane (HMD) prior to 1 H-NMR spectroscopic analysis. The carthamin contents were calculated from the ratios of singlet signal intensities at approximately σ: 9.3 derived from H-16 of carthamin to those of the HMD signal at σ: 0. The integral ratios exhibited good repeatability among NMR spectroscopic analyses. Both the intra-day and inter-day assay variations had coefficients of variation of <5%. Based on the coefficient of absorption, the carthamin contents of commercial preparations determined by 1 H-NMR spectroscopy correlated well with those determined by colorimetry, although the latter were always approximately 1.3-fold higher than the former, irrespective of the Carthamus Red preparations. In conclusion, the quantitative 1 H-NMR spectroscopy used in the present study is simple and rapid, requiring no carthamin standard for calibration. After HMD concentration has been corrected using certified reference materials, the carthamin contents determined by 1 H-NMR spectroscopy are System of Units (SI)-traceable.

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confidence: 59%

Section: Methodsmentioning

confidence: 99%

Quantitative Determination of Carthamin in Carthamus Red by <sup>1</sup>H-NMR Spectroscopy

Yoshida

Terasaka

Kato

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The combined ethyl acetate extract was concentrated under reduced pressure to yield the aglycone. The purity of each aglycone thus obtained was estimated by quantitative 1 H NMR analysis (Hasada et al, 2011). Geniposide, genipin, and loganin were obtained from Wako Pure Chemicals and secologanin from Sigma-Aldrich.…”

Section: Plant Materialsmentioning

confidence: 99%

A 7-Deoxyloganetic Acid Glucosyltransferase Contributes a Key Step in Secologanin Biosynthesis in Madagascar Periwinkle

et al. 2013

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Iridoids form a broad and versatile class of biologically active molecules found in thousands of plant species. In addition to the many hundreds of iridoids occurring in plants, some iridoids, such as secologanin, serve as key building blocks in the biosynthesis of thousands of monoterpene indole alkaloids (MIAs) and many quinoline alkaloids. This study describes the molecular cloning and functional characterization of three iridoid glucosyltransfeases (UDP-SUGAR GLYCOSYLTRANSFERASE6 [UGT6], UGT7, and UGT8) from Madagascar periwinkle (Catharanthus roseus) with remarkably different catalytic efficiencies. Biochemical analyses reveal that UGT8 possessed a high catalytic efficiency toward its exclusive iridoid substrate, 7-deoxyloganetic acid, making it better suited for the biosynthesis of iridoids in periwinkle than the other two iridoid glucosyltransfeases. The role of UGT8 in the fourth to last step in secologanin biosynthesis was confirmed by virus-induced gene silencing in periwinkle plants, which reduced expression of this gene and resulted in a large decline in secologanin and MIA accumulation within silenced plants. Localization studies of UGT8 using a carborundum abrasion method for RNA extraction show that its expression occurs preferentially within periwinkle leaves rather than in epidermal cells, and in situ hybridization studies confirm that UGT8 is preferentially expressed in internal phloem associated parenchyma cells of periwinkle species.

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“…In a previous paper, we reported the quantitative determination of the components of crude drugs by proton-specific quantitative NMR ( 1 HqNMR) [12][13][14][15][16]. The 1 H-qNMR method has various advantages over other quantitative methods, including HPLC.…”

Section: Introductionmentioning

confidence: 99%

Application of a quantitative 1H-NMR method for the determination of paeonol in Moutan cortex, Hachimijiogan and Keishibukuryogan

et al. 2016

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Quantitative (1)H-NMR ((1)H-qNMR) was applied to the determination of paeonol concentration in Moutan cortex, Hachimijiogan, and Keishibukuryogan. Paeonol is a major component of Moutan cortex, and its purity was calculated from the ratio of the intensity of the paeonol H-3' signal at δ 6.41 ppm in methanol-d 4 or 6.40 ppm in methanol-d 4 + TFA-d to that of a hexamethyldisilane (HMD) signal at 0 ppm. The concentration of HMD was corrected with SI traceability by using potassium hydrogen phthalate of certified reference material grade. As a result, the paeonol content in two lots of Moutan cortex as determined by (1)H-qNMR was found to be 1.59 % and 1.62 %, respectively, while the paeonol content in Hachimijiogan and Keishibukuryogan was 0.15 % and 0.22 %, respectively. The present study demonstrated that the (1)H-NMR method is useful for the quantitative analysis of crude drugs and Kampo formulas.

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Application of 1H-NMR spectroscopy to validation of berberine alkaloid reagents and to chemical evaluation of Coptidis Rhizoma

Cited by 30 publications

References 13 publications

Quantitative Determination of Carthamin in Carthamus Red by <sup>1</sup>H-NMR Spectroscopy

Quantitative Determination of Carthamin in Carthamus Red by <sup>1</sup>H-NMR Spectroscopy

A 7-Deoxyloganetic Acid Glucosyltransferase Contributes a Key Step in Secologanin Biosynthesis in Madagascar Periwinkle

Application of a quantitative 1H-NMR method for the determination of paeonol in Moutan cortex, Hachimijiogan and Keishibukuryogan

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