Flavonoids and a neolignan glucoside from Guarea macrophylla (Meliaceae)

Abstract

Recebido em 7/8/11; aceito em 11/1/12; publicado na web em 15/5/12 This work describes the phytochemical study of the methanol extract obtained from leaves of Guarea macrophylla, leading to the isolation and identification of three flavonoid glycosides (quercetin 3-O-b-D-glucopyranoside, quercetin 3-O-b-D-galactopyranoside, kaempferol 7-O-b-D-glucopyranoside) and a neolignan glucoside, dehydrodiconiferyl alcohol-4-b-D-glucoside. All compounds were identified by a combination of spectroscopic methods ( 1 H, 1D, 2D NMR, 13 C and UV), ESI-MS and comparison with the literature data. This is the first report of flavonoids in the genus Guarea and of a neolignan glucoside in the Meliaceae family.

Identification of the active components inhibiting the expression of matrix metallopeptidase-9 by TNFα in ethyl acetate extract of Euphorbia humifusa Willd

“…The 1 3 C-NMR data obtained from the current study were collected in dimethylsulfoxide-d6, and those published previously were in dimethylsulfoxide-d6 position 1 3 C-NMR data obtained from the current study collected in dimethylsulfoxide-d6/ ppm C-NMR data of F3 with the data published previously [9]. The 1 3 C-NMR data obtained from the current study were collected in dimethylsulfoxide-d6, and those published previously were in methanol-d4 position 1 3 C-NMR data obtained from the current study collected in dimethylsulfoxide-d6/ ppm A comparison of the 13 C-NMR data of F1 with the data published previously [11] was listed in Table 3. Previously, we have demonstrated that the EA/EuH fraction exhibited anti-metastatic activity by suppressing MMP-9 mRNA expression in MDA-MB-231 breast cancer cells [1].…”

Chemical constituents of Ficus consociata Blume (Moraceae)

“…The anomeric proton H-1 at δH 5.46 showed a long-range correlation with signal at δC 133.3 (C-3) of the quercetin aglycon, indicating that the β-Dglucopyranosyl moiety connected to C-3 of the aglycon. The above data and comparison with those in the literature [4,5,6] allowed to identify 3 as quercetin 3-O-β-D-glucopyranoside (or isoquercetin).…”

New jacaranone glucoside from Jacaranda oxyphylla leaves

“…Subfraction e8′ (1.472 g) was submitted to CC using CHCl 3 -MeOH (3:1), ten subfractions were obtained (e1″-e10″) and subfraction e3″ yielded compound 3 (330.1 mg, 1.6%). Quercetin-3-O-β-d-galactoside (2): yellow powder; IR (ATR, cm −1 ): 3270,2963,1656,1606,1504,1342,1171,1078,1021; NMR spectral data are in accordance with Pereira et al (2012).…”

“…A recent study identified three new jacaranone derivatives from aerial parts of Senecio chrysanoides that presented cytotoxic activity (Wu et al 2015). The known compounds ( Figure 1) were identified as quercetin-3-O-β-d-galactoside (2), verbascoside (3) and polystyrene (4) by comparison with their NMR data with literature reports (Pham et al 1991;Schlauer et al 2004;Pereira et al 2012). Compound 2 is also known as hyperoside and it has been isolated from Jacaranda decurrens leaves (Blatt et al 1998), while compound 3 (1.6% of etOH extract) was previously identified from the hydroalcoholic extract of J. mimosifolia leaves (Moharram & Marzouk 2007).…”