C-methylated and C-prenylated isoflavonoids from root extract of Desmodium uncinatum

Guchu, Salome M; Yenesew, Abiy; Tsanuo, Muniru K.; Gikonyo, Nicholas K.; Pickett, John A.; Hooper, Antony M.; Hassanali, Ahmed

doi:10.1016/j.phytochem.2006.11.035

Cited by 24 publications

(30 citation statements)

References 13 publications

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“…Suicidal germination of striga seed by desmodium root exudates is demonstrated by a reduced striga seed bank in the field where desmodium is intercropped (Khan et al, 2008). Our examination of the metabolome of desmodium roots and root exudates has shown the biosynthesis of biologically active isoflavanones, uncinanone A, uncinanone B (a germination stimulant of S. hermonthica) and uncinanone C (a S. hermonthica radicle growth inhibitor) (Tsanuo et al, 2003) as well as biologically inactive isoflavones and pterocarpans (Guchu et al, 2007). In this work the chemical cause of radicle inhibition was further investigated by bioassayguided fractionation of the more polar fractions of desmodium root chemistry which were known in their crude state to possess more radicle inhibitory activity than less polar fractions.…”

Section: Introductionmentioning

confidence: 93%

Isoschaftoside, a C-glycosylflavonoid from Desmodium uncinatum root exudate, is an allelochemical against the development of Striga

et al. 2010

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Section: Introductionmentioning

confidence: 93%

Isoschaftoside, a C-glycosylflavonoid from Desmodium uncinatum root exudate, is an allelochemical against the development of Striga

et al. 2010

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“…Desmodium triflorum has been reported to express antioxidant (Lai et al, 2010), analgesic and antiinflammatory activities (Lai et al, 2009), and 2"-Oglucosylvitexin, vitexin, isovitexin, apigenin, and (+)-pinitol have been isolated from this plant (Adinarayana and Syamasundar, 1982). Another plant from this genus, Desmodium uncinatum, has been shown to possess genistein, uncinanone A, uncinanone B, uncinanone C (Tsanuo et al, 2003), uncinanone D and uncinanone E (Guchu et al, 2007) with phytochemical studies. However, no studies to date have been able to demonstrate antioxidant effect of any Desmodium species other than D. gangeticum and D. triflorum.…”

Section: Introductionmentioning

confidence: 99%

Antioxidant activities of phenolic components from various plants of Desmodium species

Tsai¹,

Huang²,

Chiu³

et al. 2011

Afr. J. Pharm. Pharmacol.

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The aim of this study was to examine the antioxidant activities and phenolic components of the crude extracts of 10 Desmodium species from Taiwan. In this study, DPPH free radical scavenging activity, ABTS radical monocation scavenging activity, ferric-reducing antioxidant power (FRAP) and reducing power of the 10 Desmodium species were evaluated for their antioxidant activities. The results showed that, of all the samples, Desmodium sequax was the most active in ABTS, DPPH, FRAP and reducing power assays. The total polyphenol, total flavonoid and total flavonol contents of the crude extract were calculated. The correlation coefficient (R 2 ) values of TEAC with phenolic compounds indicated strong positive correlations, except for total flavonoid content. Furthermore, HPLC chromatographic fingerprints were established, and chlorogenic acid and vitexin in D. sequax were quantified. Chlorogenic acid was confirmed to express strong antioxidant activities in ABTS, DPPH, FRAP and reducing power assays. The present study indicated the antioxidant activities of the 10 Desmodium species were related to their phenolic components. D. sequax is a potent antioxidant medicinal plant, and chlorogenic acid may be an important factor in the antioxidant activity of this plant.

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“…It was assigned a molecular formula of C 25 H 28 O 4 (m/z 392.1652) from HREIMS. A set of three AMX patterns of double doublets in the 1 H NMR spectrum at δ 4.45 (J = 10.5, 7.5 Hz), 4.62 (J = 11.3, 5.2 Hz), and 3.91 (J = 5.2, 10.5 Hz) for the aliphatic proton signals and carbon signals at δ 70.83 (C-2), 51.12 (C-3), and 196.89 (C-4) were consistent with compound 4 being an isoflavanone derivative [10,11]. The 1 H and 13 C NMR spectra indicated the presence of one 3-methylbut-2-enyl, one hydroxyl, and dimethyl pyranosyl substituents on the isoflavanone skeleton.…”

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confidence: 53%

New prenylated isoflavanones from the roots of Glycyrrhiza glabra

2009

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547.972Two new prenylated isoflavanones have been isolated from the roots of Glycyrrhiza glabra L. along with the known compounds cetoleic acid, β-sitosterol, stigmasterol, lanast-5,24-dien-3β-D-glucuronopyranoside, and glucuronic acid. The structures of the prenylated isoflavanones have been established as 8-isoprenyl-7,4′-dihydroxylicoisoflavanone (glabraisoflavanone A) and 7,3′-dihydroxy-8-isoprenyl-4′-cyclogeranioloxyisoflavanone (glabraisoflavanone B) on the basis of spectral data analyses and chemical reactions.Glycyrrhiza glabra L. (Fabaceae), commonly known in trade as liquorice, is a perennial herb distributed in subtropical and warm temperate regions of the world [1]. The roots are reported to have anti-inflammatory, demulcent, expectorant, and tonic properties and are prescribed to treat sore throat, bronchial catarrh, cough, gastric and duodenal ulcers, dyspepsia, allergic reactions, arthritis, rheumatism, tuberculosis, and liver toxicity [1, 2]. The important phytoconstituents isolated from the roots included glycyrrhizin, liquiritic acid, glabranins A and B, glycyrrhetol, glabrolide, formononetin, liquiritin, isoliquertin, and other phenolic compounds [3][4][5][6][7][8][9]. This present paper describes the isolation and characterization of the known compounds cetoleic acid (1), β-sitosterol (2), stigmasterol (3), lanast-5,24-dien-3β-D-glucuronopyranoside (6), glucuronic acid (7) and of two new prenylated isoflavanones (4, 5) from the roots of G. glabra of northern India.Compound 4, designated as glabraisoflavanone A, was obtained as a pale yellow crystalline product from chloroform eluates. Its UV λ max at 211, 294 nm and the presence of the O-CH 2 -CH-CO sequence in its 1 H and 13 C NMR spectra (Table 1) accounted for its isoflavanone structure. The presence of a bathochromic shift after addition of sodium acetate in the UV spectrum indicated a free hydroxyl group at C-7. It was assigned a molecular formula of C 25 H 28 O 4 (m/z 392.1652) from HREIMS. A set of three AMX patterns of double doublets in the 1 H NMR spectrum at δ 4.45 (J = 10.5, 7.5 Hz), 4.62 (J = 11.3, 5.2 Hz), and 3.91 (J = 5.2, 10.5 Hz) for the aliphatic proton signals and carbon signals at δ 70.83 (C-2), 51.12 (C-3), and 196.89 (C-4) were consistent with compound 4 being an isoflavanone derivative [10,11]. The 1 H and 13 C NMR spectra indicated the presence of one 3-methylbut-2-enyl, one hydroxyl, and dimethyl pyranosyl substituents on the isoflavanone skeleton.

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C-methylated and C-prenylated isoflavonoids from root extract of Desmodium uncinatum

Cited by 24 publications

References 13 publications

Isoschaftoside, a C-glycosylflavonoid from Desmodium uncinatum root exudate, is an allelochemical against the development of Striga

Isoschaftoside, a C-glycosylflavonoid from Desmodium uncinatum root exudate, is an allelochemical against the development of Striga

Antioxidant activities of phenolic components from various plants of Desmodium species

New prenylated isoflavanones from the roots of Glycyrrhiza glabra

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