6,7-dimethoxyisoflavone-2 -O–D-glucopyranoside (9), 5,2 ,3 -trihydroxy-6,7pyranoside (9), five,two,3-trihydroxy-6,7-dimethoxyisoflavone (ten), with each other with seven dimethoxyisoflavone (10), with each other
6,7-dimethoxyisoflavone-2 -O–D-glucopyranoside (9), five,2 ,three -trihydroxy-6,7pyranoside (9), 5,2,3-trihydroxy-6,7-dimethoxyisoflavone (ten), collectively with seven dimethoxyisoflavone (ten), together with seven known compounds (Figure 1): four flaknown compoundsone isoflavone (8), one flavonol (11), and one particular sterol (12).oneaddition, vanone (four, five, six, 7), (Figure 1): four flavanone (four, 5, 6, 7), one isoflavone (8), In flavonol we aimed to sterol (12). Furthermore, we aimed to evaluate the effectiveness and potency (11), and one evaluate the effectiveness and potency of those all-natural compounds utilizing antimicrobial, cell proliferation and cytotoxicity cell proliferation and cytotoxicity assays. of these all-natural compounds utilizing antimicrobial, assays.Figure 1. The structures of compounds 12.2. Outcomes and Discussion two. Results and Discussion 2.1. Structure Elucidation two.1. Structure ElucidationThe ethanol extracts in the underground parts I. I. tenuifolia had been subjected for the ethanol extracts from the underground components of of tenuifolia were subjected to rereOligomycin A web peated column chromatography followed by crystallizationsleading for the isolation of peated column chromatography followed by crystallizations major towards the isolation of five unprecedented chromane derivatives. five unprecedented chromane derivatives. Compound 1 was isolated as white crystal. HR-ESI-MS showed an ion peak at m/z Compound 1 was isolated as white crystal. HR-ESI-MS showed an ion peak at m/z 453.1409 [M + H]+ corresponding a a molecular formula of C 24 H24 Its . Its 1 H spec453.1409 [M + H]+ corresponding to to molecular formula of C21H21O11. O111H NMR NMR spectrum acquired in DMSO-d6 (Table 1) showed resonances for meta-coupled aromatic trum acquired in DMSO-d6 (Table 1) showed resonances for meta-coupled aromatic proprotons H 6.14 6.14 (1H, J = 2.0and and H five.95 (1H, J = 2.0 Hz), two olefinic protons at tons at at H (1H, J = two.0 Hz) Hz) H five.95 (1H, J = two.0 Hz), two olefinic protons at H six.94 H H and methylene signals signals H 3.21.81 and number of oxygenated protons and6.945.75, H five.75, methylenebetweenbetween H three.21.81 and variety of oxygenated protons between H 5.50.08 corresponding togroups asgroups too as 2-Bromo-6-nitrophenol web oxymethines. involving H 5.50.08 corresponding to hydroxy hydroxy effectively as oxymethines. The presThe of a two,five,7-trisubstituted chromane-4-one was identified by evaluation of HMBC correencepresence of a 2,5,7-trisubstituted chromane-4-one was identified by analysis of HMBC correlations observed for the meta-coupled aromatic doublets H-6 and H-8 also as lations observed for the meta-coupled aromatic doublets 1 H-6 and H-8 too as methmethylene signals H-2 and H-3 (Figure 2a). Moreover, the H NMR spectrum exhibited a ylene signals H-2 and H-3 (Figure 2a). Moreover, the 1H NMR spectrum exhibited a signal signal of 1 chelated hydroxyl group (H 12.04), which can be characteristic downfield shift of one chelated hydroxyl group (H 12.04), which is characteristic downfield shift of a hyof a hydroxyl group at C-5 as well as a carbonyl group at C-4. Furthermore, the presence of a droxyl group at C-5 plus a carbonyl group at C-4. Additionally, the presence of a hydroxyl hydroxyl group at C-5 was supported by HMBC correlations from 5-OH ( 12.04) to C-5 group at C-5 was supported by HMBC correlations from 5-OH (H 12.04) toH (C 163.1), C-5 (C 163.1), C-6 (C 97.three) and C-10 (C 103.4). HSQC, HMBC, and COSY information clearly revealed the existence of a glucose residue. Additional analysis in the spin-spin c.
