An isoflavan-quinone and a flavonol from Millettia laurentii1Part 10 in the series “The Millettia of Cameroon”.1

Kamnaing, Pierre; Free, Samuel N. Y. Fanso; Nkengfack, Augustin E.; Folefoc, Gabriel N.; Fomum, Zacharias Tanee

doi:10.1016/s0031-9422(99)00043-6

Cited by 36 publications

(11 citation statements)

References 10 publications

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“…The isoflavan-quinones represent a rare group of plant secondary metabolites, and only a few structures have been reported thus far. Examples include claussequinone, astragaluquinone, pendulone, amorphaquinone, colutequinone, laurentiquinone, mucroquinone, and the abruquinones. − It is not clear as to whether isoflavan-quinones are genuine natural products or oxidation products of related isoflavans. Grosvenor and Gray showed that colutequinone was present in the original extract, together with colutehydroquinone, which is readily converted into the quinone.…”

Section: Resultsmentioning

confidence: 99%

Isoflavonoids and Coumarins from Glycyrrhiza uralensis: Antibacterial Activity against Oral Pathogens and Conversion of Isoflavans into Isoflavan-Quinones during Purification

Gafner¹,

Bergeron²,

Villinski³

et al. 2011

J. Nat. Prod.

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Phytochemical investigation of a supercritical fluid extract of Glycyrrhiza uralensis has led to the isolation of 20 known isoflavonoids and coumarins, and glycycarpan (7), a new pterocarpan. The presence of two isoflavan-quinones, licoriquinone A (8) and licoriquinone B (9), in a fraction subjected to gel filtration on Sephadex LH-20 is due to suspected metal-catalyzed oxidative degradation of licoricidin (1) and licorisoflavan A (2). The major compounds in the extract, as well as 8, were evaluated for their ability to inhibit the growth of several major oral pathogens. Compounds 1 and 2 showed the most potent antibacterial activities, causing a marked growth inhibition of the cariogenic species Streptococcus mutans and Streptococcus sobrinus at 10 μg/mL and the periodontopathogenic species Porphyromonas gingivalis (at 5 μg/mL) and Prevotella intermedia (at 5 μg/mL for 1 and 2.5 μg/mL for 2). Only 1 moderately inhibited growth of Fusobacterium nucleatum at the highest concentration tested (10 μg/mL).

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Section: Resultsmentioning

confidence: 99%

Isoflavonoids and Coumarins from Glycyrrhiza uralensis: Antibacterial Activity against Oral Pathogens and Conversion of Isoflavans into Isoflavan-Quinones during Purification

Gafner¹,

Bergeron²,

Villinski³

et al. 2011

J. Nat. Prod.

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“…Bioactivity-guided fractionation of the ethanolic extract of P. arborescens yielded four isoflavones, the new 5,7,3′,4′-tetrahydroxy-2′-(3,3-dimethylallyl)isoflavone (1a), fremontin (3a), 8 glycyrrhisoflavone (4a), 9 and calycosin (5), [10][11][12][13] a new 2-arylbenzofuran, 2-(2′-hydroxy-4′,5′-methylenedioxyphenyl)-6-methoxybenzofuran-3-carbaldehyde (2), the pterocarpans maackiain (6) [14][15][16][17] and 4-hy-droxymaackiain (7), 17,18 the triterpene oleanolic acid (8), 10,19 and the chalcone isoliquiritigenin (9). 20,21 The structures of the known compounds were determined by 1D and 2D NMR techniques and confirmed by comparing the physical and spectroscopic/spectrometric data with those from the literature (NMR and MS).…”

Section: Resultsmentioning

confidence: 99%

Isoflavonoids and Other Compounds from Psorothamnus arborescens with Antiprotozoal Activities

Salem

Werbovetz

2005

J. Nat. Prod.

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Bioactivity-guided fractionation of the root extract of Psorothamnus arborescens yielded the new isoflavone 5,7,3',4'-tetrahydroxy-2'-(3,3-dimethylallyl)isoflavone (1a) and the new 2-arylbenzofuran 2-(2'-hydroxy-4',5'-methylenedioxyphenyl)-6-methoxybenzofuran-3-carbaldehyde (2), together with seven known compounds, including three isoflavones, fremontin (3a), glycyrrhisoflavone (4a), and calycosin (5), two pterocarpans, maackiain (6) and 4-hydroxymaackiain (7), one triterpene, oleanolic acid (8), and one chalcone, isoliquiritigenin (9). In addition, the structure of the isoflavone fremontin was revised using spectroscopic and chemical methods and was assigned the new structure 3a. The isoflavone 1a and the chalcone 9 displayed leishmanicidal activity with IC50 values of 13.0 and 20.7 microM, respectively, against Leishmania donovani axenic amastigotes. Calycosin (5) exhibited selective toxicity against Trypanosoma brucei brucei (IC50 12.7 microM) compared to L. donovani amastigotes and Vero cells (IC50 100 and 159 microM, respectively). These results prompted us to test a small group of structurally related isoflavones for their antitrypanosomal activities. Genistein and 7,3',4'-trihydroxyisoflavone displayed promising activity (IC50 values 4.2 and 7.1 microM, respectively) and selectivity (IC50 versus Vero cells: 32.9 and 135 microM, respectively). These studies suggest that the isoflavone skeleton deserves further investigation as a template for novel antileishmanial and trypanocidal compounds.

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“…In the absence of new data on the biosynthesis of 2-arylbenzofurans in legumes, inferences about their biogenetic origins can only be drawn from their co-occurrence with other derived isoflavonoids, with particular reference to patterns of A-and B-ring substitution, and chemical hypotheses. A good example is afforded by the new derivative cicerfuran (395), 384 which occurs in the roots of Cicer bijugum, Cicer judaicum and Cicer pinnatifidum together with the identically substituted isoflav-3-ene, judaicin (7-hydroxy-2 -methoxy-4 ,5methylenedioxyisoflav-3-ene), and 2-methoxyjudaicin (351). 353 These findings suggest that the corresponding 2-hydroxyisoflav-3-ene is a likely precursor, a hypothesis supported in part by Kinoshita's mechanism describing the chemical conversion of 2-hydroxyisoflav-3-enes to 2-arylbenzofurans.…”

Section: -Arylbenzofuransmentioning

confidence: 99%

Isoflavonoids of the Leguminosae

Veitch

2007

Nat. Prod. Rep.

204

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Isoflavonoids are found predominantly in subfamily Papilionoideae of the Leguminosae. This review describes more than 420 new examples of Leguminosae isoflavonoids, giving details of their source, identification, biological activity, synthesis, and ecological or chemosystematic significance. Other topics addressed include the application of hyphenated analytical techniques to the characterisation of legume-derived isoflavonoids, and advances made in biosynthetic studies. A checklist of new compounds by species is given, and 404 references are cited.

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An isoflavan-quinone and a flavonol from Millettia laurentii1Part 10 in the series “The Millettia of Cameroon”.1

Cited by 36 publications

References 10 publications

Isoflavonoids and Coumarins from Glycyrrhiza uralensis: Antibacterial Activity against Oral Pathogens and Conversion of Isoflavans into Isoflavan-Quinones during Purification

Isoflavonoids and Coumarins from Glycyrrhiza uralensis: Antibacterial Activity against Oral Pathogens and Conversion of Isoflavans into Isoflavan-Quinones during Purification

Isoflavonoids and Other Compounds from Psorothamnus arborescens with Antiprotozoal Activities

Isoflavonoids of the Leguminosae

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