Three isoflav-3-enes and a 2-arylbenzofuran from the root bark of Erythrina burttii

Yenesew, Abiy; Midiwo, Jacob O.; Guchu, Salome M; Heydenreich, Matthias; Peter, Martin G.

doi:10.1016/s0031-9422(01)00459-9

Cited by 38 publications

(16 citation statements)

References 14 publications

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“…These compounds also co-occur in E. abyssinca [5], supporting the biogenetic relationship between arylbenzofurans and isoflav-3-enes. The arylbenzofuran burttinol D co-occurs with the isoflav-3-ene burttinol A in the roots of E. burttii [12], and similar biogenetic relationship has been suggested for these compounds [11].…”

Section: Resultsmentioning

confidence: 73%

8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica

Yenesew¹,

Twinomuhwezi²,

Kiremire³

et al. 2009

Bull. Chem. Soc. Eth.

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ABSTRACT.ABSTRACT. ABSTRACT. ABSTRACT. A new pterocarpan (named 8-methoxyneorautenol) was isolated from the acetone extract of the root bark of Erythrina abyssinica. In addition, the known isoflavonoid derivatives eryvarin L, erycristagallin and shinpterocarpin were identified for the first time from the roots of this plant. The structures were determined on the basis of spectroscopic evidence. The new compound showed selective antimicrobial activity against Trichophyton mentagrophytes. The acetone extract of the root bark of E. abyssinica showed radical scavenging activity towards 2,2-diphenyl-1-picrylhydrazyl radical (DPPH). The pterocarpenes, 3-hydroxy-9-methoxy-10-(3,3-dimethylallyl)pterocarpene and erycristagallin, were the most active constituents of the roots of this plant and showing dose-dependent activities similar to that of the standard quercetin.

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Section: Resultsmentioning

confidence: 73%

8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica

Yenesew¹,

Twinomuhwezi²,

Kiremire³

et al. 2009

Bull. Chem. Soc. Eth.

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“…2′,4,4′‐Trihydroxy‐3′‐(3″‐methyl‐2″‐butenyl)chalcone ( 1 ), more commonly known as isobavachalcone, is a prenylated chalcone and can be isolated from many plants, including Psoralea corylifolia ,10 Dorstenia zenkeri ,11 Angelica keiskei ,12 Kadsura ananosma ,13 Erythrina burttii 14 and Broussonetia papyrifera 15. It has been shown to have inhibitory effects on skin tumours16 and the Epstein–Barr virus,17 and has significant antimicrobial activity against the hospital pathogens Staphylococcus aureus and S. epidermidisat 18.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Isobavachalcone and Some Organometallic Derivatives

et al. 2012

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Isobavachalcone [2′,4,4′‐trihydroxy‐3′‐(3″‐methyl‐2″‐butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of $190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium‐catalysed Stille coupling of 3‐iodo‐2,4‐bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen–Schmidt condensation with 4‐(methoxymethoxy)benzaldehyde to form the triply MOM‐protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X‐ray crystal structures of 2,4‐dihydroxy‐3‐iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen‐bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4‐(methoxymethoxy)benzaldehyde used in the Claisen–Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5‐formylcyclopentadienyl)(η4‐tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.

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“…6,8,18 These data, together with the HMBC correlations of H-2 with C-8a, C-3, C-4, and C-1′, and correlations between H-2 and H-6′ in a NOESY experiment unequivocally suggested a pterocarpene skeleton. 3,[19][20][21] Furthermore, the presence of two hydroxyls, one methoxy, and two 3,3-dimethylallyl substituents was evident from the MS data and NMR spectra (see Experimental Section). Three aromatic proton singlets at δ 7.10, 7.08, and 6.31 appeared in the 1 H NMR spectrum, together with the biogenetically expected oxygenation at C-5, C-7, and C-4′, 1,7,19,21,22 indicating that the 3,3-dimethylallyl groups could be placed at C-6, C-8, or C-5′.…”

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confidence: 99%

Antibacterial Compounds from Glycyrrhiza uralensis

et al. 2006

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From the roots of Glycyrrhiza uralensis, two new pterocarpenes, glycyrrhizol A (1) and glycyrrhizol B (2), along with four known isoflavonoids, 5-O-methylglycryol (3), isoglycyrol (4), 6,8-diisoprenyl-5,7,4′-trihydroxyisoflavone (5), and gancaonin G (6), were isolated using a bioassay-guided fractionation method. The structures of the new compounds (1 and 2) were elucidated by spectroscopic data interpretation. The known compounds (3-6) were identified by comparison of their spectroscopic data with reported values in the literature. Glycyrrhizol A (1) and 6,8-diisoprenyl-5,7,4′-trihydroxyisoflavone (5) exhibited potent antibacterial activity against Streptococcus mutans with minimum inhibitory concentrations of 1 and 2 µg/mL, respectively, while glycyrrhizol B (2) and gancaonin G (6) showed more moderate activity.

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Three isoflav-3-enes and a 2-arylbenzofuran from the root bark of Erythrina burttii

Cited by 38 publications

References 14 publications

8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica

8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica

Synthesis of Isobavachalcone and Some Organometallic Derivatives

Antibacterial Compounds from Glycyrrhiza uralensis

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