Studies on Coumarins of a Chinese Drug “Qian-Hu” V. Coumarin-glycosides from “Zi-Hua Qian-Hu”<sup>1</sup>

Asahara, Takashi; Sakakibara, Iwao; Okuyama, Toru; Shibata, Sayaka

doi:10.1055/s-2007-969780

Cited by 41 publications

(21 citation statements)

References 3 publications

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“…The smaller coupling constant of J H-2′,H-3′ has unequivocally been assigned to H-2′ and H-3′ trans-confi guration (Asahara et al, 1984;Vilegas et al, 1993). The above-mentioned data are consistent with the structure of 3′(R)-hydroxy-nodakenetin-3′-ol (Asahara et al, 1984;Vilegas et al, 1993).…”

Section: Identifi Cation Of Nani Metabolitessupporting

confidence: 61%

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A new metabolite of nodakenetin by rat liver microsomes and its quantification by RP‐HPLC method

Zhang

Yang

2009

Biomedical Chromatography

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The biotransformation of nodakenetin (NANI) by rat liver microsomes in vitro was investigated. Two major polar metabolites were produced by liver microsomes from phenobarbital-pretreated rats and detected by reversed-phase high-performance liquid chromatography (RP-HPLC) analysis. The chemical structures of two metabolites were firmly identified as 3'(R)-hydroxy-nodakenetin-3'-ol and 3'(S)-hydroxy-nodakenetin-3'-ol, respectively, on the basis of their (1)H-NMR, MS and optical rotation analysis. The latter was a new compound. A sensitive, selective and simple RP-HPLC method has been developed for the simultaneous determination of NANI and its two major metabolites in rat liver microsomes. Chromatographic conditions comprise a C(18) column, a mobile phase with MeOH-H(2)O (40 : 60, v/v), a total run time of 40 min, and ultraviolet absorbance detection at 330 nm. In the rat heat-inactivated liver microsomal supernatant, the lower limits of detection and quantification of metabolite I, metabolite II and NANI were 5.0, 2.0, 10.0 ng/mL and 20.0, 5.0, 50.0 ng/mL, respectively, and their calibration curves were linear over the concentration range 50-400, 20-120 and 150-24000 ng/mL, respectively. The results provided a firm basis for further evaluating the pharmacokinetics and clinical efficacy of NANI.

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Section: Identifi Cation Of Nani Metabolitessupporting

confidence: 61%

“…Metabolite (Asahara et al, 1984;Vilegas et al, 1993). On the basis of evidence above, the structure of metabolite II was unequivocally established as 3′(S)-hydroxy-nodakenetin-3′-ol (Fig.…”

Section: Identifi Cation Of Nani Metabolitesmentioning

confidence: 93%

A new metabolite of nodakenetin by rat liver microsomes and its quantification by RP‐HPLC method

Zhang

Yang

2009

Biomedical Chromatography

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“…The chemical shifts of all the individual H-atoms of the sugar moieties were ascertained by a combination of 1D-TOCSY and DQF-COSY spectroscopic analyses, and the 13 C-NMR chemical shifts ( Table 1) of the corresponding C-atoms were assigned unambiguously from the HSQC spectrum. Chemical shifts, multiplicities of the signals, and the absolute values of the coupling constants in the NMR spectra indicated the presence of one b-glucopyranose and one b-apiofuranose moiety [11]. Apiofuranosyl configuration was also confirmed by comparing 1 H, 1 H scalar coupling constants with those reported for methyl apiofuranosides and dlapiose, as well as NOE correlations.…”

mentioning

confidence: 56%

“…35 -50% towards the intact microsomal G-6-Pase. Compounds 3,5,11,14, and 16 were the only ones that moderately inhibit the G-6-Pase of disrupted microsomes.…”

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confidence: 94%

Phenolic Derivatives from Ruprechtia polystachya and Their Inhibitory Activities on the Glucose‐6‐phosphatase System

Abreu

Temraz

Malafronte

et al. 2011

Chemistry & Biodiversity

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Two new compounds, 5-methyl-2-(2-methylbutanoyl)phloroglucinol 1-O-(6-O-β-D-apiofuranosyl)-β-D-glucopyranoside (1) and trans-2,3-dihydrokaempferol 3-O-(4-O-sulfo)-α-L-arabinopyranoside (2), together with 14 known flavonoids, trans-dihydrokaempferol 3-O-α-L-arabinopyranoside (3), trans-taxifolin 3-O-α-L-arabinofuranoside (4), quercetin 3-O-α-L-rhamnopyranoside (5), quercetin 3'-O-α-L-arabinofuranoside (6), catechin 3-O-α-L-rhamnopyranoside (7), trans-taxifolin 3-O-α-L-arabinopyranoside (8), cis-dihydrokaempferol 3-O-α-L-arabinopyranoside (9), catechin (10), myricetin 3-O-α-L-rhamnopyranoside (11), quercetin 3-O-α-L-arabinopyranoside (12), quercetin 3-O-α-L-arabinofuranoside (13), quercetin 3-O-(3″-galloyl)-α-L-rhamnopyranoside (14), quercetin 3-O-(2″-galloyl)-α-L-rhamnopyranoside (15), and epicatechin 3-O-gallate (16), were isolated from the leaves of Ruprechtia polystachya Griseb. (Polygonaceae). Their structures were established on the basis of extensive 1D- and 2D-NMR experiments as well as MS analyses. All compounds, except 1, showed inhibition of the enzyme glucose-6-phosphatase in intact microsomes.

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“…), and the linear non-glycosidic pyranocoumarins Pd-C-I, Pd-C-II, Pd-C-III, Pd-C-IV, Pd-C-V and AD-I, as well as various saponins, from Zi-Hua Qianhu, the root of P. decursivum MAXIM. [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] In addition, we recently isolated two novel angular pyranocoumarin glycosides, peucedanosides A and B, along with apterin 23) and praerosides e and f, 24) from Peucedanum praeruptorum DUNN.…”

Section: Notesmentioning

confidence: 99%

Studies of Coumarins from the Chinese Drug Qianhu, XXVII: Structure of a New Simple Coumarin Glycoside from Bai-Hua Qianhu, Peucedanum praeruptorum

Ishii

Okada

Baba

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new simple coumarin glycoside, named praeroside VI (1), along with six known coumarins, were isolated from an aqueous extract of Bai-Hua Qianhu, the root of Peucedanum praeruptorum DUNN. (Umbelliferae). Spectroscopic analysis and chemical studies were carried out to investigate the structure of the new coumarin, which was concluded to be 1. Additionally, two simple glycosidic coumarins and four simple nonglycosidic coumarins were identified as apiosylskimmin (2), hymexelsin (3), umbelliferone (4), scopoletin (5), isofraxidin (6) and 8-carboxy-7-hydroxy coumarin (7), respectively. This is the first reported identification of compound 7 as a constituent of plant materials.

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Studies on Coumarins of a Chinese Drug “Qian-Hu” V. Coumarin-glycosides from “Zi-Hua Qian-Hu”¹

Cited by 41 publications

References 3 publications

A new metabolite of nodakenetin by rat liver microsomes and its quantification by RP‐HPLC method

A new metabolite of nodakenetin by rat liver microsomes and its quantification by RP‐HPLC method

Phenolic Derivatives from Ruprechtia polystachya and Their Inhibitory Activities on the Glucose‐6‐phosphatase System

Studies of Coumarins from the Chinese Drug Qianhu, XXVII: Structure of a New Simple Coumarin Glycoside from Bai-Hua Qianhu, Peucedanum praeruptorum

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Studies on Coumarins of a Chinese Drug “Qian-Hu” V. Coumarin-glycosides from “Zi-Hua Qian-Hu”1

Cited by 41 publications

References 3 publications

A new metabolite of nodakenetin by rat liver microsomes and its quantification by RP‐HPLC method

A new metabolite of nodakenetin by rat liver microsomes and its quantification by RP‐HPLC method

Phenolic Derivatives from Ruprechtia polystachya and Their Inhibitory Activities on the Glucose‐6‐phosphatase System

Studies of Coumarins from the Chinese Drug Qianhu, XXVII: Structure of a New Simple Coumarin Glycoside from Bai-Hua Qianhu, Peucedanum praeruptorum

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Studies on Coumarins of a Chinese Drug “Qian-Hu” V. Coumarin-glycosides from “Zi-Hua Qian-Hu”¹