Chromone glycosides comprise an important group of secondary metabolites. They are widely distrib... more Chromone glycosides comprise an important group of secondary metabolites. They are widely distributed in plants and, to a lesser extent, in fungi and bacteria. Significant biological activities, including antiviral, anti-inflammatory, antitumor, antimicrobial, etc., have been discovered for chromone glycosides, suggesting their potential as drug leads. This review compiles 192 naturally occurring chromone glycosides along with their sources, classification, biological activities, and spectroscopic features. Detailed biosynthetic pathways and chemotaxonomic studies are also described. Extensive spectroscopic features for this class of compounds have been thoroughly discussed, and detailed 13C-NMR data of compounds 1–192, have been added, except for those that have no reported 13C-NMR data.
Abstract: Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuan... more Abstract: Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuana tipu growing in Egypt. The isolated compounds were identified as 1-Nonadecanol (1), β-sitosterol (2), Alpinumisoflavone (3), β-sitosterol glucoside (4), Protocatechualdehyde (5) and Protocatechuic acid (6), based on different spectroscopic data (UV, IR, NMR and MS). This is the first report for the isolation of compounds 1 & 3-6 from Tipuana tipu. Compound 1 is isolated for the first time from family Fabaceae. Compounds 2 and 3 showed a promising anticancer activity, while compound 5 displayed a remarkable in vivo anti-inflammatory activity compared to indomethacin. [Amen YM, Marzouk AM, Zaghloul MG, Afifi MS. Bioactive compounds from Tipuana tipu growing in Egypt. J Am Sci 2013;9(10)
The extract from Entada phaseoloides was employed as active ingredients of natural origin into co... more The extract from Entada phaseoloides was employed as active ingredients of natural origin into cosmetic products, while the components analysis was barely reported. Using LC-DAD-MS/qTOF analysis, eleven compounds (1–11) were proposed or identified from acetone extract of E. phaseoloides leaves (AE). Among them, six phenolic compounds, protocatechuic acid (2), 4-hydroxybenzoic acid (3), luteolin-7-O-β-d-glucoside (5), cirsimaritin (6), dihydrokaempferol (9), and apigenin (10), were isolated by various chromatographic techniques. Protocatechuic acid (2), epicatechin (4), and kaempferol (11) at a concentration 100 μM increased the HaCaT cells viability of the UVB-irradiated cell without any cytotoxicity effect and reduced the expression of COX-2 and iNOS inflammation gene. Moreover, compounds 2 and 4 could have potent effects on cell migration during wound closure. These results suggest that compounds 2, 4, and 11 from AE have anti-photoaging properties and could be employed in pharmac...
The extract from Entada phaseoloides was employed as active ingredients of natural origin into co... more The extract from Entada phaseoloides was employed as active ingredients of natural origin into cosmetic products, while the components analysis was barely reported. Using LC-DAD-MS/qTOF analysis, eleven compounds (1–11) were proposed or identified from acetone extract of E. phaseoloides leaves (AE). Among them, six phenolic compounds, protocatechuic acid (2), 4-hydroxybenzoic acid (3), luteolin-7-O-β-d-glucoside (5), cirsimaritin (6), dihydrokaempferol (9), and apigenin (10), were isolated by various chromatographic techniques. Protocatechuic acid (2), epicatechin (4), and kaempferol (11) at a concentration 100 μM increased the HaCaT cells viability of the UVB-irradiated cell without any cytotoxicity effect and reduced the expression of COX-2 and iNOS inflammation gene. Moreover, compounds 2 and 4 could have potent effects on cell migration during wound closure. These results suggest that compounds 2, 4, and 11 from AE have anti-photoaging properties and could be employed in pharmac...
Two new compounds, 11S-methoxy-11,12-dihydro phytuberin (2) and 9S-methoxy-benzocyclononan-7-one ... more Two new compounds, 11S-methoxy-11,12-dihydro phytuberin (2) and 9S-methoxy-benzocyclononan-7-one (6), together with twenty-six known ones were isolated from Lycium schweinfurthii (Solanaceae). Their planar structure was established by extensive spectroscopic analyses. The absolute configuration of compound 6 was determined by time dependent density functional theory calculations (TDDFT). The cytotoxic potential of the isolates was assessed in cultured skin cancer (G-361) and colon cancer (HCT-116 and CaCo-2) cell lines. Certain flavonoids showed the highest cytotoxic activity, with IC50 values ranging from 7.1 to 63.3 µM; meanwhile 5-flurouracil showed IC50 values ranging from 62.4 to >100 µM. All compounds showed minimal toxicity towards normal cells from skin (NHDF-4) and colon (CCD-841), indicating their potential selectivity and safety as cytotoxic candidates.
Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuana tipu gro... more Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuana tipu growing in Egypt. The isolated compounds were identified as 1-Nonadecanol (1), β-sitosterol (2), Alpinumisoflavone (3), β- sitosterol glucoside (4), Protocatechualdehyde (5) and Protocatechuic acid (6), based on different spectroscopic data (UV, IR, NMR and MS). This is the first report for the isolation of compounds 1 & 3-6 from Tipuana tipu. Compound 1 is isolated for the first time from family Fabaceae. Compounds 2 and 3 showed a promising anticancer activity, while compound 5 displayed a remarkable in vivo anti-inflammatory activity compared to indomethacin. (Amen YM, Marzouk AM, Zaghloul MG, Afifi MS. Bioactive compounds from Tipuana tipu growing in Egypt. J Am Sci 2013;9(10):334-339). (ISSN: 1545-1003). http://www.jofamericanscience.org. 44
In recent years, entomophagy has attracted increased attention, as it was recommended as a potent... more In recent years, entomophagy has attracted increased attention, as it was recommended as a potential source of food by the Food and Agriculture Organization of the United Nations. In Japan, Oxya yezoensisis one of the most widely eaten insect species, but studies of its functionality as a food are limited. In this study, we reported the optimal characterization of the total phenolic compounds in methanolic extract (OME) and different fractions of OME. Additionally, the antioxidant and antiallergic activities of the OME fractions were evaluated. The results showed that the ethyl acetate-soluble fraction of OME has potential antioxidant activity, whereas the n-hexane-soluble fraction showed the strongest inhibition of β-hexosaminidase, which is one of the key factors in allergic reactions. It was concluded that phenolic compounds might contribute to the antioxidant activity while unsaturated fatty acids contribute to the antiallergy activity.
Abstract Our effort to find new material for anti cancer from natural resources leads us to focus... more Abstract Our effort to find new material for anti cancer from natural resources leads us to focus on stingless bee products such as honey, bee pollen, and propolis. The products were from seven stingless bees named Homotrigona fimbriata, Heterotrigona itama, Heterotrigona bakeri, Tetragonula sarawakensis, Tetragonula testaceitarsis, Tetragonula fuscobalteata, Tetragonula laeviceps. The stingless bee products were evaluated for their cytotoxicity effect on MCF-7, HeLa and Caco-2 cancer cell lines. This is the first time to be reported that the honey, ethanol extracts of bee pollen and propolis of H. fimbriata displayed more potent cytotoxicity than other stingless bee products. By chromatography and biological activity-guided fractionation, ethanol extract of propolis from H. fimbriata was fractionated and isolated its active compound named mangiferonic acid. Mangiferonic acid showed a cytotoxicity effect with IC50 values 96.76 µM in MCF-7, >110.04 µM in HeLa, and > 110.04 µM in Caco-2, respectively. These results exhibited the potential of ethanol extracts from propolis of H. fimbriata to be further developed for drug and experiments to verify the function are essential.
Propolis from 4 stingless bees (Homotrigona apicalis, Wallacetrigona incisa, Tetragonula fuscobal... more Propolis from 4 stingless bees (Homotrigona apicalis, Wallacetrigona incisa, Tetragonula fuscobalteata, and Tetragonula fuscibasis) was investigated in the search for medicinal and cosmetic materials from tropical rainforest resources. Methanol extracts of the propolis were screened using antioxidant and antimelanogenesis assays (tyrosinase enzyme activity and melanin inhibitor in B16 melanoma). The extract of H. apicalis showed the strongest antioxidant activity, both in the 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) assays, with half-maximal inhibitory concentration values of 0.72 ± 0.01 (mg/mL) and 0.26 ± 0.00 (mg/mL), respectively. The H. apicalis extract also displayed the strongest inhibition of tyrosinase (53% at 100 µg/mL). In the B16 melanoma cell assay, the W. incisa extract showed the strongest inhibition of melanin (21%) and was less cytotoxic. The W. incisa extract was fractioned to isolate the compounds with biological activities. Two prenylated flavonoids were obtained, named broussoflavonol F and glyasperin A. Both showed potent antioxidant activities, as well as inhibiting melanin in B16 melanoma, but not tyrosinase activity. These results indicated the potential of methanol extract of W. incisa to be developed for cosmetic material, but further experiments are needed to verify the function.
Natural products and traditional medicine products with known safety profiles are a promising sou... more Natural products and traditional medicine products with known safety profiles are a promising source for the discovery of new drug leads.
Chromone glycosides comprise an important group of secondary metabolites. They are widely distrib... more Chromone glycosides comprise an important group of secondary metabolites. They are widely distributed in plants and, to a lesser extent, in fungi and bacteria. Significant biological activities, including antiviral, anti-inflammatory, antitumor, antimicrobial, etc., have been discovered for chromone glycosides, suggesting their potential as drug leads. This review compiles 192 naturally occurring chromone glycosides along with their sources, classification, biological activities, and spectroscopic features. Detailed biosynthetic pathways and chemotaxonomic studies are also described. Extensive spectroscopic features for this class of compounds have been thoroughly discussed, and detailed 13C-NMR data of compounds 1–192, have been added, except for those that have no reported 13C-NMR data.
Abstract: Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuan... more Abstract: Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuana tipu growing in Egypt. The isolated compounds were identified as 1-Nonadecanol (1), β-sitosterol (2), Alpinumisoflavone (3), β-sitosterol glucoside (4), Protocatechualdehyde (5) and Protocatechuic acid (6), based on different spectroscopic data (UV, IR, NMR and MS). This is the first report for the isolation of compounds 1 & 3-6 from Tipuana tipu. Compound 1 is isolated for the first time from family Fabaceae. Compounds 2 and 3 showed a promising anticancer activity, while compound 5 displayed a remarkable in vivo anti-inflammatory activity compared to indomethacin. [Amen YM, Marzouk AM, Zaghloul MG, Afifi MS. Bioactive compounds from Tipuana tipu growing in Egypt. J Am Sci 2013;9(10)
The extract from Entada phaseoloides was employed as active ingredients of natural origin into co... more The extract from Entada phaseoloides was employed as active ingredients of natural origin into cosmetic products, while the components analysis was barely reported. Using LC-DAD-MS/qTOF analysis, eleven compounds (1–11) were proposed or identified from acetone extract of E. phaseoloides leaves (AE). Among them, six phenolic compounds, protocatechuic acid (2), 4-hydroxybenzoic acid (3), luteolin-7-O-β-d-glucoside (5), cirsimaritin (6), dihydrokaempferol (9), and apigenin (10), were isolated by various chromatographic techniques. Protocatechuic acid (2), epicatechin (4), and kaempferol (11) at a concentration 100 μM increased the HaCaT cells viability of the UVB-irradiated cell without any cytotoxicity effect and reduced the expression of COX-2 and iNOS inflammation gene. Moreover, compounds 2 and 4 could have potent effects on cell migration during wound closure. These results suggest that compounds 2, 4, and 11 from AE have anti-photoaging properties and could be employed in pharmac...
The extract from Entada phaseoloides was employed as active ingredients of natural origin into co... more The extract from Entada phaseoloides was employed as active ingredients of natural origin into cosmetic products, while the components analysis was barely reported. Using LC-DAD-MS/qTOF analysis, eleven compounds (1–11) were proposed or identified from acetone extract of E. phaseoloides leaves (AE). Among them, six phenolic compounds, protocatechuic acid (2), 4-hydroxybenzoic acid (3), luteolin-7-O-β-d-glucoside (5), cirsimaritin (6), dihydrokaempferol (9), and apigenin (10), were isolated by various chromatographic techniques. Protocatechuic acid (2), epicatechin (4), and kaempferol (11) at a concentration 100 μM increased the HaCaT cells viability of the UVB-irradiated cell without any cytotoxicity effect and reduced the expression of COX-2 and iNOS inflammation gene. Moreover, compounds 2 and 4 could have potent effects on cell migration during wound closure. These results suggest that compounds 2, 4, and 11 from AE have anti-photoaging properties and could be employed in pharmac...
Two new compounds, 11S-methoxy-11,12-dihydro phytuberin (2) and 9S-methoxy-benzocyclononan-7-one ... more Two new compounds, 11S-methoxy-11,12-dihydro phytuberin (2) and 9S-methoxy-benzocyclononan-7-one (6), together with twenty-six known ones were isolated from Lycium schweinfurthii (Solanaceae). Their planar structure was established by extensive spectroscopic analyses. The absolute configuration of compound 6 was determined by time dependent density functional theory calculations (TDDFT). The cytotoxic potential of the isolates was assessed in cultured skin cancer (G-361) and colon cancer (HCT-116 and CaCo-2) cell lines. Certain flavonoids showed the highest cytotoxic activity, with IC50 values ranging from 7.1 to 63.3 µM; meanwhile 5-flurouracil showed IC50 values ranging from 62.4 to >100 µM. All compounds showed minimal toxicity towards normal cells from skin (NHDF-4) and colon (CCD-841), indicating their potential selectivity and safety as cytotoxic candidates.
Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuana tipu gro... more Six compounds were isolated from methanolic extracts of the leaf and the bark of Tipuana tipu growing in Egypt. The isolated compounds were identified as 1-Nonadecanol (1), β-sitosterol (2), Alpinumisoflavone (3), β- sitosterol glucoside (4), Protocatechualdehyde (5) and Protocatechuic acid (6), based on different spectroscopic data (UV, IR, NMR and MS). This is the first report for the isolation of compounds 1 & 3-6 from Tipuana tipu. Compound 1 is isolated for the first time from family Fabaceae. Compounds 2 and 3 showed a promising anticancer activity, while compound 5 displayed a remarkable in vivo anti-inflammatory activity compared to indomethacin. (Amen YM, Marzouk AM, Zaghloul MG, Afifi MS. Bioactive compounds from Tipuana tipu growing in Egypt. J Am Sci 2013;9(10):334-339). (ISSN: 1545-1003). http://www.jofamericanscience.org. 44
In recent years, entomophagy has attracted increased attention, as it was recommended as a potent... more In recent years, entomophagy has attracted increased attention, as it was recommended as a potential source of food by the Food and Agriculture Organization of the United Nations. In Japan, Oxya yezoensisis one of the most widely eaten insect species, but studies of its functionality as a food are limited. In this study, we reported the optimal characterization of the total phenolic compounds in methanolic extract (OME) and different fractions of OME. Additionally, the antioxidant and antiallergic activities of the OME fractions were evaluated. The results showed that the ethyl acetate-soluble fraction of OME has potential antioxidant activity, whereas the n-hexane-soluble fraction showed the strongest inhibition of β-hexosaminidase, which is one of the key factors in allergic reactions. It was concluded that phenolic compounds might contribute to the antioxidant activity while unsaturated fatty acids contribute to the antiallergy activity.
Abstract Our effort to find new material for anti cancer from natural resources leads us to focus... more Abstract Our effort to find new material for anti cancer from natural resources leads us to focus on stingless bee products such as honey, bee pollen, and propolis. The products were from seven stingless bees named Homotrigona fimbriata, Heterotrigona itama, Heterotrigona bakeri, Tetragonula sarawakensis, Tetragonula testaceitarsis, Tetragonula fuscobalteata, Tetragonula laeviceps. The stingless bee products were evaluated for their cytotoxicity effect on MCF-7, HeLa and Caco-2 cancer cell lines. This is the first time to be reported that the honey, ethanol extracts of bee pollen and propolis of H. fimbriata displayed more potent cytotoxicity than other stingless bee products. By chromatography and biological activity-guided fractionation, ethanol extract of propolis from H. fimbriata was fractionated and isolated its active compound named mangiferonic acid. Mangiferonic acid showed a cytotoxicity effect with IC50 values 96.76 µM in MCF-7, >110.04 µM in HeLa, and > 110.04 µM in Caco-2, respectively. These results exhibited the potential of ethanol extracts from propolis of H. fimbriata to be further developed for drug and experiments to verify the function are essential.
Propolis from 4 stingless bees (Homotrigona apicalis, Wallacetrigona incisa, Tetragonula fuscobal... more Propolis from 4 stingless bees (Homotrigona apicalis, Wallacetrigona incisa, Tetragonula fuscobalteata, and Tetragonula fuscibasis) was investigated in the search for medicinal and cosmetic materials from tropical rainforest resources. Methanol extracts of the propolis were screened using antioxidant and antimelanogenesis assays (tyrosinase enzyme activity and melanin inhibitor in B16 melanoma). The extract of H. apicalis showed the strongest antioxidant activity, both in the 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) assays, with half-maximal inhibitory concentration values of 0.72 ± 0.01 (mg/mL) and 0.26 ± 0.00 (mg/mL), respectively. The H. apicalis extract also displayed the strongest inhibition of tyrosinase (53% at 100 µg/mL). In the B16 melanoma cell assay, the W. incisa extract showed the strongest inhibition of melanin (21%) and was less cytotoxic. The W. incisa extract was fractioned to isolate the compounds with biological activities. Two prenylated flavonoids were obtained, named broussoflavonol F and glyasperin A. Both showed potent antioxidant activities, as well as inhibiting melanin in B16 melanoma, but not tyrosinase activity. These results indicated the potential of methanol extract of W. incisa to be developed for cosmetic material, but further experiments are needed to verify the function.
Natural products and traditional medicine products with known safety profiles are a promising sou... more Natural products and traditional medicine products with known safety profiles are a promising source for the discovery of new drug leads.
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