Alkaloids and phenylpropanoids from Peganum nigellastrum

Ma, Zhongjun; Hano, Yoshio; Nomura, Taro; Chen, Ying‐Jie

doi:10.1016/s0031-9422(99)00440-9

Cited by 68 publications

(38 citation statements)

References 9 publications

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“…Various compounds have been reported in this plant, including alkaloids, phenylpropanoids, triterpenes, and so on [2][3][4][5][6]. We have studied the chemical constituents of the ethanol extract of the aerial part and obtained a novel flavone glycoside with a tetrasaccharide.…”

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confidence: 99%

A new flavone glycoside from the aerial part of Peganum nigellastrum

Yang

Feng

et al. 2010

Chem Nat Compd

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Keywords: Peganum nigellastrum, diosmetin 7-O-E-D-glucopyranosyl(1o2)-E-D-glucopyranosyl(1o2)-[D-Lrhamnopyranosyl(1o6)]-E-D-glucopyranoside, flavone glycoside. Peganum nigellastrum Bge. (Zygophyllaceae) is distributed over Asia and commonly found in the northwest region of China. The plant has been used as a Chinese traditional medicine for rheumatism, abscess, inflammation, and so on [1].Various compounds have been reported in this plant, including alkaloids, phenylpropanoids, triterpenes, and so on [2-6]. We have studied the chemical constituents of the ethanol extract of the aerial part and obtained a novel flavone glycoside with a tetrasaccharide. Its structure was determined as diosmetin 7The ethanol extract of the aerial part of P. nigellastrum was fractionated on silica gel with petroleum, ethyl acetate, and methanol. Isolation and purification were achieved using a combination of TLC, MCI, and Sephadex LH-20.Compound 1 was a pale yellow powder. The 13 C NMR showed the characteristic signals of flavonoid at G 181.9 (C=O), 164.1 (C-2), and 103.8 (C-3). The signals of H at G 6.50 (1H, d, J = 2.05 Hz, H-6) and 6.81 (1H, d, J = 2.05 Hz, H-8) were meta-coupled with each other, and the signals of C-6 (G 99.5) and C-8 (G 94.8) moved to higher field, confirming that the ring A was substituted by O at C-5 and C-7.

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confidence: 99%

A new flavone glycoside from the aerial part of Peganum nigellastrum

Yang

Feng

et al. 2010

Chem Nat Compd

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“…1), the major compound (1) showing the best antifungal activity. The spectral data ( 1 H-NMR, 13 C-NMR, IR, mass) of compound 1 revealed that this compound was canthin-6-one, previously isolated from Ailanthus altissima (Simaroubaceae) (Ohmoto et al, 1976), Brucea antidysenterica (Simaroubaceae) (Fukamiya et al, 1987), Eurycoma harmandiana (Simaroubaceae) (Kanchanapoom et al, 2001), Peganum nigellastrum (Zygophyllaceae) (Ma et al, 2000) and mentioned from Zanthoxylum elephantiasis (Rutaceae) (Mitscher et al, 1972) as an antifungal compound. The in vitro activity of canthin-6-one (1) and 5-methoxy-canthin-6-one (2) were assessed against 12 species of microorganisms (Table 1).…”

Section: Resultsmentioning

confidence: 94%

Antifungal compounds from Zanthoxylum chiloperone var. angustifolium

Thouvenel

Gantier

Duret

et al. 2003

Phytotherapy Research

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An alkaloidal extract of the stem barks of Zanthoxylum chiloperone var. angustifolium exhibited antifungal activity against Candida albicans, Aspergillus fumigatus and Trichophyton mentagrophytes var. interdigitale using a TLC bioautographic method. Bioassay-guided fractionation of this extract resulted in the isolation of two active compounds identi fi ed as canthin-6-one and 5-methoxycanthin-6-one. Canthin-6-one exhibited a broad spectrum of activities against Aspergillus fumigatus, A. niger, A. terreus, Candida albicans, C. tropicalis, C. glabrata, Cryptococcus neoformans, Geotrichum candidum, Saccharomyces cerevisiae, Trichosporon beigelii, Trichosporon cutaneum and Trichophyton mentagrophytes var. interdigitale with MICs values between 5.3 and 46 micro mol/L. 5-methoxy-canthin-6-one was active against only Trichophyton mentagrophytes var. interdigitale with a MIC value of 12.3 micro mol/L.

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“…Reactions with Br 2 in glacial AcOH, CHCl 3 , MeOH, and other solvents transformed them into tribromides (181) at the Py N atom that reacted with ketones (acetone, acetophenone) to give the corresponding hydrobromides (182). Treatment of their solutions with NaHCO 3 gave the bromides of deoxyvasicinone, deoxyvasicinethione, deoxypeganine, and their derivatives (183). Heating the tribromides in AcOH (75%) formed D,D-dibromo derivatives (184).…”

Section: Electrophilic Substitution In the Aromatic Ring Of Tricyclicmentioning

confidence: 99%

“…The alkaloids luotonin A and B (29 and 30) exhibit cytotoxic activity against the P-388 murine leukemia cell line (IC 50 = 1.8 Pg/mL) [8] and stabilizing activity for human DNA topoisomerase 1 [180][181][182][183].…”

Section: Electrophilic Substitution In the Aromatic Ring Of Tricyclicmentioning

confidence: 99%