Flavone glycosides from Erythrina caffra (Fabaceae)

El-Masry, Sawsan; Hamoda, HM; Radwan, Mohamed M.; Ross, Samir A.; Zaatout, Hala H.

doi:10.1055/s-0030-1251826

Cited by 7 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This finding was further confirmed by the absence of H-6 and H-8 in the 1 H NMR spectrum. The spectral data (Table 1 ) obtained were similar to the reported ones [ 34 , 35 ], confirming the identification of compound 1 as 6,8-di- C -β- D -glucopyranoside (vicenin-2).…”

Section: Resultssupporting

confidence: 85%

Flavones from Erythrina falcata are modulators of fear memory

Oliveira

Zamberlam

Gaiardo

et al. 2014

BMC Complement Altern Med

View full text Add to dashboard Cite

BackgroundFlavonoids, which have been identified in a variety of plants, have been demonstrated to elicit beneficial effects on memory. Some studies have reported that flavonoids derived from Erythrina plants can provide such beneficial effects on memory. The aim of this study was to identify the flavonoids present in the stem bark crude extract of Erythrina falcata (CE) and to perform a bioactivity-guided study on conditioned fear memory.MethodsThe secondary metabolites of CE were identified by high performance liquid chromatography combined with a diode array detector, electrospray ionization tandem mass spectrometry (HPLC-DAD-ESI/MSn) and nuclear magnetic resonance (NMR). The buthanolic fraction (BuF) was obtained by partitioning. Subfractions from BuF (BuF1 – BuF6) and fraction flavonoidic (FfA and FfB) were obtained by flash chromatography. The BuF3 and BuF4 fractions were used for the isolation of flavonoids, which was performed using HPLC-PAD. The isolated substances were quantified by HPLC-DAD and their structures were confirmed by nuclear magnetic resonance (NMR). The activities of CE and the subfractions were monitored using a one-trial, step-down inhibitory avoidance (IA) task to identify the effects of these substances on the acquisition and extinction of conditioned fear in rats.ResultsSix subclasses of flavonoids were identified for the first time in CE. According to our behavioral data, CE, BuF, BuF3 and BuF4, the flavonoidic fractions, vitexin, isovitexin and 6-C-glycoside-diosmetin improved the acquisition of fear memory. Rats treated with BuF, BuF3 and BuF4 were particularly resistant to extinction. Nevertheless, rats treated with FfA and FfB, vitexin, isovitexin and 6-C-glycoside-diosmetin exhibited gradual reduction in conditioned fear response during the extinction retest session, which was measured at 48 to 480 h after conditioning.ConclusionsOur results demonstrate that vitexin, isovitexin and diosmetin-6-C-glucoside and flavonoidic fractions resulted in a significant retention of fear memory but did not prevent the extinction of fear memory. These results further substantiate that the treatment with pure flavonoids or flavanoid-rich fractions might represent potential therapeutic approaches for the treatment of neurocognitive disorders, improvement of memory acquisition and spontaneous recovery of fear.

show abstract

Section: Resultssupporting

confidence: 85%

Flavones from Erythrina falcata are modulators of fear memory

Oliveira

Zamberlam

Gaiardo

et al. 2014

BMC Complement Altern Med

View full text Add to dashboard Cite

show abstract

“…Based on the physicochemical and chromatographic properties, spectral analyses (UV, 1 H, and DEPT‒Q NMR), as well as comparison with the literature and some authentic samples, the compounds isolated (Figure 2) from the ethanolic extract of P. odorata bark afforded the new tetrahydrofurofurnan lignan 35 , along with the known 4 β -hydroxyasarinin-1- o - β -glucopyranoside 36 [18], 1,5 α -dihydroxypinoresinol 37 [22], premnadimer-A 38 [18], 3-[3′-methoxy-4′-(4′’-formyl-2′’,6′’-dimethoxy-phenoxy)-phenyl]-propenal 39 [23], sinapaldehyde 40 [24], 3,5-dimethoxybenzaldehyde 41 [24], apigenin 42 , luteolin 43 , diosmetin 44 , vitexin 45 [5], orientin 46 [25],vicenin-2 47 [16], schaftoside-2 48 [17], and apigenin-6,8-di- c - α - l -arabinopyranoside 49 (Figure 2) [25]. All characterized compounds ( 37 , 39 – 41 , 46 – 49 ) were isolated herein for the first time from the genus Premna , while compounds 36 , 38 were isolated for the first time from the Premna species.…”

Section: Resultsmentioning

confidence: 99%

Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco

et al. 2019

View full text Add to dashboard Cite

Metabolomic profiling of different Premna odorata Blanco (Lamiaceae) organs, bark, wood, young stems, flowers, and fruits dereplicated 20, 20, 10, 20, and 20 compounds, respectively, using LC–HRESIMS. The identified metabolites (1–34) belonged to different chemical classes, including iridoids, flavones, phenyl ethanoids, and lignans. A phytochemical investigation of P. odorata bark afforded one new tetrahydrofurofuran lignan, 4β-hydroxyasarinin 35, along with fourteen known compounds. The structure of the new compound was confirmed using extensive 1D and 2D NMR, and HRESIMS analyses. A cytotoxic investigation of compounds 35–38 against the HL-60, HT-29, and MCF-7 cancer cell lines, using the MTT assay showed that compound 35 had cytotoxic effects against HL-60 and MCF-7 with IC50 values of 2.7 and 4.2 µg/mL, respectively. A pharmacophore map of compounds 35 showed two hydrogen bond acceptor (HBA) aligning the phenoxy oxygen atoms of benzodioxole moieties, two aromatic ring features vectored on the two phenyl rings, one hydrogen bond donor (HBD) feature aligning the central hydroxyl group and thirteen exclusion spheres which limit the boundaries of sterically inaccessible regions of the target’s active site.

show abstract

“…is indigenous to South Africa and is a mediumsized to large deciduous subtropical tree. Previous studies on the stem bark of E. caffra yielded flavanones, isoflavones [3] and C-flavonoidal glycosides [4]. In this paper we report the isolation and structural elucidation of three new flavonoids, along with eight known compounds from the stem bark of E. caffra.…”

mentioning

confidence: 84%

Three New Isoflavonoids from Erythrina caffra

Desta

Majinda

2014

Natural Product Communications

View full text Add to dashboard Cite

Three new isoflavonoids, 5,7-dihydroxy-2',4'-dimethoxy-5'-(3-methylbut-2-enyl) isoflavanone (erycaffra A) (1), 5,7-dihydroxy-2',4'-dimethoxy-5'-(2-hydroxy-3-methylbut-3-enyl)isoflavanone (erycaffra B) (2), and 5,7-dihydroxy-6,8-di-(2-hydroxy-3-methylbut-3-enyl)isoflavone (erycaffra C) (3), were isolated from the stem bark of E. caffra Thunb., along with eight known compounds, namely, alpinumisoflavone (4), isoerysenegalensein E (5), β-amyrin (6), oleanolic acid (7), octacosyl-E-ferulate (8), triacontyl-4-hydroxycinnamate (9), n-tetracosyl p-coumarate (10) and octacosan-1-ol (11). The structures were determined on the basis of spectroscopic (1D, 2D-NMR) and MS data and by comparison with literature values.

show abstract

Flavone glycosides from Erythrina caffra (Fabaceae)

Cited by 7 publications

References 0 publications

Flavones from Erythrina falcata are modulators of fear memory

Flavones from Erythrina falcata are modulators of fear memory

Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco

Three New Isoflavonoids from Erythrina caffra

Contact Info

Product

Resources

About