Flavanones from the stem bark of Erythrina abyssinica

Cui, Long; Thương, Phương Thiện; Lee, Hyun Sun; Ndinteh, Derek Tantoh; Mbafor, Joseph Tanyi; Fomum, Zacharias Tanee; Oh, Won Keun

doi:10.1016/j.bmc.2008.10.012

Cited by 37 publications

(26 citation statements)

References 15 publications

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“…Compound 3 was identified as 2(S)-5,7-dihydroxy-5′-prenyl-[2″,2″-(3″-hydroxy)-dimethylpyrano]-(5″,6″:3′,4′)flavanone. This compound was already reported Cui et al in the stem bark of Erythrina abyssinica 18 , all analytical data found by us are identical to those reported there. The NMR data of 4 also indicated a 5,7-dihydroxy-flavanone with a single 3,3-dimethylallyl side chain.…”

Section: Resultssupporting

confidence: 91%

Prenylated flavanone derivatives isolated from Erythrina addisoniae are potent inducers of apoptotic cell death

et al. 2015

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Extracts of Erythrina addisoniae are frequently used in the traditional medicine of Western Africa, but only insufficient information about active compounds is available. From the stem bark of Erythrina addisoniae, three new (1, 2, 4) and three known (3, 5, 6) flavanones were isolated: addisoniaflavanones I and II, containing either a 2´´,3´´-epoxyprenyl moiety (1) or a 2´´,3´´-dihydroxyprenyl moiety (2) were shown to be highly toxic (MTT-assay: EC 50 -values of 5.25 +/-13.5 and 8.5 +/-15.2 µM, respectively) against H4IIE hepatoma cells. The cytotoxic potential of the other isolated flavanones was weaker (range of EC 50 -values between 15 and >100 µM). Toxic effects of addisoniaflavanone I and II were detectable after 3 h (MTT assay). Both compounds induced an apoptotic cell death (caspase 3/7 activation, nuclear fragmentation) in the hepatoma cells and, at high concentrations, also necrosis (membrane disruption: ethidium bromide staining), Formation of DNA strand breaks was not detectable after incubation with these compounds (comet assay). In conclusion, the new prenylated flavanones addisoniaflavanones I and II may be of interest for pharmacological purposes (e.g. potential use as cytostatic drugs) due to their high cytotoxic and pro-apoptotic potential.

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Section: Resultssupporting

confidence: 91%

Prenylated flavanone derivatives isolated from Erythrina addisoniae are potent inducers of apoptotic cell death

et al. 2015

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“…It is used in traditional medicine for treatment of malaria, elephantiasis, trachoma and syphilis [2]. Previous phytochemical studies on E. abyssinica have shown that the plant elaborates alkaloids [1], flavanones, pterocarpans, chalcones and isoflavonoids [1,3]; some of which have been shown to have antimicrobial [2,4], antiplasmodial [5,6] and inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) [3] activities. In this paper, we report on the isolation and structure elucidation of a new pterocarpan, along with known isoflavonoid derivatives.…”

Section: Introductionmentioning

confidence: 99%

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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“…The first synthesis of other flavonoids, such as 35, 39, 40, and 45, has also been reported [40,[57][58][59] (Figure 2). Abyssinoflavanones V-VII 46-48, together with sigmoidins A-C 49-51, F 52, abyssinins I 53, II 44, 5-deoxyabyssinin II 54, 3'-prenylnarringenin 55, abyssinone-VI 56, licoagrochalcone A 57 [49] , flavonoids 58-73 [50] , flavanones 74-79 with a dihydrofuran moiety, erylatissin C 80, abyssinin III 81 [51] , and flavanones 82-93 [52] were isolated from the stem bark of E abyssinica. 50 >72 µmol/L).…”

Section: Flavonoidsmentioning

confidence: 99%

“…Abyssinoflavanones V-VII 46-48, together with sigmoidins A-C 49-51, F 52, abyssinins I 53, II 44, 5-deoxyabyssinin II 54, 3'-prenylnarringenin 55, abyssinone-VI 56, licoagrochalcone A 57 [49] , flavonoids 58-73 [50] , flavanones 74-79 with a dihydrofuran moiety, erylatissin C 80, abyssinin III 81 [51] , and flavanones 82-93 [52] were isolated from the stem bark of E abyssinica. 50 >72 µmol/L). All of these results indicated that the significant inhibitory activity of these flavonoids could be attributed to the isoprenyl or methoxyl groups in the ring B, while the presence of a polar functionality (eg, hydroxyl group) caused the activity to decrease.…”

Section: Flavonoidsmentioning

confidence: 99%

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

2012

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This article provides an overview of approximately 300 secondary metabolites with inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), which were isolated from various natural sources or derived from synthetic process in the last decades. The structure-activity relationship and the selectivity of some compounds against other protein phosphatases were also discussed. Potential pharmaceutical applications of several PTP1B inhibitors were presented.

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Flavanones from the stem bark of Erythrina abyssinica

Cited by 37 publications

References 15 publications

Prenylated flavanone derivatives isolated from Erythrina addisoniae are potent inducers of apoptotic cell death

Prenylated flavanone derivatives isolated from Erythrina addisoniae are potent inducers of apoptotic cell death

8-Methoxyneorautenol and radical scavenging flavonoids from Erythrina abyssinica

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

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