1H and 13C NMR assignments for two new angular furanocoumarin glycosides from Peucedanum praeruptorum

Chang, Haitao; Okada, Yoshihito; Okuyama, Toru; Tu, Peng‐Fei

doi:10.1002/mrc.2005

Cited by 24 publications

(12 citation statements)

References 13 publications

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“…29 The Cprenyl group is also found cyclised onto an ortho-phenol to form extensive ranges of furanoflavones and pyranoflavones. 30 One may speculate that the isomeric furanoflavone 1 and pyranoflavone 2 (also atalantoflavone 16 ) arise through 5-exo and 6-endo cyclisations of a common oxidised derivative of 4, such as 8-(3,3-dimethyloxiranylmethyl)-4′,5,7-trihydroxyflavone. Retamasin A and retamasin B, previously reported in R. raetam, 16 are furanoflavones which may also derive from 4.…”

Section: Resultsmentioning

confidence: 99%

New flavonoids from the Saudi Arabian plant Retama raetam which stimulates secretion of insulin and inhibits α-glucosidase

et al. 2019

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Retama raetam is a bush which is a member of the family Fabaceae. It is used traditionally in North Africa and Saudi Arabia for the treatment of diabetes. Several flavonoids and alkaloids were already known from this plant. Chromatographic fractionation and purification led to the isolation of three new derivatives of prenylated flavones, retamasin C-E and four new derivatives of prenylated isoflavones, retamasin F-I, in addition to two isoflavones which had not previously been reported in this plant. Particularly interesting structures included isoflavones containing 3,5-dihydro-2H-2,5-methanobenzo[e] [1,4]dioxepine and 3a,8b-dihydro-7-hydroxyfuro[3,2-b]benzo[2,1-d]furan units, both of which are new amongst natural product flavonoids. Five new examples (two flavones and three isoflavones) strongly enhanced the glucose-triggered release of insulin by murine pancreatic islets and one isoflavone was a potent inhibitor of α-glucosidase. This study may rationalise the traditional medicinal use of R. raetam and provides new leads for drug design in the treatment of diabetes.

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Section: Resultsmentioning

confidence: 99%

New flavonoids from the Saudi Arabian plant Retama raetam which stimulates secretion of insulin and inhibits α-glucosidase

et al. 2019

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“…Phytochemical and pharmacological studies showed that angular-type pyranocoumarins are the major constituents of this plant [3][4][5][6][7][8][9], and these compounds have various beneficial effects such as anti-inflammatory [10][11][12], antiasthma [13], chemopreventive [14], smooth muscle relaxant [15], neuroprotective [16], and anti-osteoclastogenic properties [17].…”

Section: Introductionmentioning

confidence: 99%

“…The structures of the isolates were determined spectroscopically using one-dimensional (1D)-and two-dimensional (2D)-nuclear magnetic resonance (NMR) analysis. All the compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were evaluated for multidrug resistance (MDR) reversal and anti-inflammatory activity against multidrug resistant MES-SA/Dx5 cancer and lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Here, we 1 Hz, H-4′′′), 1.81 (3H, m, H-5′′′)] were observed from the 1 H-NMR spectrum.…”

Section: Introductionmentioning

confidence: 99%

Pyranocoumarins from Root Extracts of Peucedanum praeruptorum Dunn with Multidrug Resistance Reversal and Anti-Inflammatory Activities

Lee

Kim

et al. 2015

Molecules

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Abstract:In the search for novel herbal-based anticancer agents, we isolated a new angular-type pyranocoumarin, (+)-cis-(3 1 S,4 1 S)-3 1 -angeloyl-4 1 -tigloylkhellactone (1) along with 12 pyranocoumarins (2-13), two furanocoumarins (14, 15), and a polyacetylene (16) were isolated from the roots of Peucedanum praeruptorum using chromatographic separation methods. The structures of the compounds were determined using spectroscopic analysis with nuclear magnetic resonance (NMR) and high-resolution-electrospray ionization-mass spectrometry (HR-ESI-MS). The multidrug-resistance (MDR) reversal and anti-inflammatory effects of all the isolated compounds were evaluated in human sarcoma MES-SA/Dx5 and lipopolysaccharide (LPS)-induced RAW 264.7 cells. Among the 16 tested compounds, two (2 and 16) downregulated nitric oxide (NO) production and five (1, 7, 8, 11, and 13) inhibited the efflux of drugs by MDR protein, indicating the reversal of MDR. Therefore, these compounds may be potential candidates for the development of effective agents against MDR forms of cancer.

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“…So far, more than 50 coumarins have been isolated from Peucedani Radix, including (±)‐praeruptorin A, (±)‐praeruptorin B, (+)‐praeruptorin A, (+)‐praeruptorin B, (+)‐praeruptorin E, etc 7–10. Most of these coumarins belong to angular‐type pyranocoumarin, which has a khellactone skeleton with different substituents at the C‐3′ and C‐4′ positions.…”

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confidence: 99%

pH‐Controlled Reversible Formation of a Supramolecular Hyperbranched Polymer Showing Fluorescence Switching

Wang

Guo

et al. 2013

Chemistry A European J

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A π-conjugated AB2 monomer 1 with a dibenzo[24]crown-8 (DB24C8) ring and two secondary amine centres has been synthesised. Treatment of a solution of 1 in dichloromethane with trifluoroacetic acid (TFA) leads to protonation of the amine groups, and then the DB24C8 rings are threaded by the dialkylammonium ion centres of other monomer molecules, leading to the formation of a supramolecular hyperbranched polymer, TFA-1. Rather strong π-π stacking interactions between the conjugated cores are evident in this polymer. The supramolecular hyperbranched polymer (SHP) can be completely depolymerised by adding a slight excess of N-tert-butyl-N',N',N'',N'',N''',N'''-hexamethylphosphorimidic triamide, tetrabutylammonium fluoride, or tetrabutylammonium acetate. The acid-base-controlled process induces a reversible change in the fluorescence intensities of the solutions due to the controllable presence of the π-π stacking interactions between the conjugated cores. This dynamic behaviour is significant with respect to "smart" supramolecular polymer materials.

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¹H and ¹³C NMR assignments for two new angular furanocoumarin glycosides from Peucedanum praeruptorum

Cited by 24 publications

References 13 publications

New flavonoids from the Saudi Arabian plant Retama raetam which stimulates secretion of insulin and inhibits α-glucosidase

New flavonoids from the Saudi Arabian plant Retama raetam which stimulates secretion of insulin and inhibits α-glucosidase

Pyranocoumarins from Root Extracts of Peucedanum praeruptorum Dunn with Multidrug Resistance Reversal and Anti-Inflammatory Activities

pH‐Controlled Reversible Formation of a Supramolecular Hyperbranched Polymer Showing Fluorescence Switching

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