From the ethyl acetate extract of the medicinal plant Graptophyllum glandulosum Turrill, five known compounds: Lupeol (1), Oleanolic acid (2), Chrysoeriol (3), N-methyl-isonicotinamide (4) and β-sitosterol 3-O-β-D-g...From the ethyl acetate extract of the medicinal plant Graptophyllum glandulosum Turrill, five known compounds: Lupeol (1), Oleanolic acid (2), Chrysoeriol (3), N-methyl-isonicotinamide (4) and β-sitosterol 3-O-β-D-glucopyranoside (5) were isolated. In addition, oxidation reactions carried out on lupeol (1) yielded two semi-synthetic compounds, including a previously unreported: (20R)-formyloxy-29-nor-lupan-3-one (1b) and one other well-known Lupenone (1a). The structures of natural and semi-synthetic compounds were determined by analysis of 1D-(1H, 13C), 2D-(COSY, HSQC and HMBC) NMR data in conjunction with mass spectrometry (TOFESIMS and HR-TOFESIMS) and by comparison with the reported data. The evaluation of antimicrobial activities of substrate (1) as well as semi-synthetic derivatives (1a and 1b) using broth microdilution method showed that compound 1b was the most active (16 ≤ MIC ≤ 32 μg/mL) against Escherichia coli, Staphylococcus aureus and Candida albicans compared to the starting material 1 (16 ≤ MIC ≤ 64 μg/mL) and derivative 1a (32 ≤ MIC ≤ 64 μg/mL).展开更多
Starting from sissotrin (1), a natural isoflavonoid isolated from Trifolium baccarinii (Fabaceae), one new semisynthetic derivative, 6-nitrobiochanin A (1b) and two known derivatives, 8-nitrobiochanin A (1a) and 2&quo...Starting from sissotrin (1), a natural isoflavonoid isolated from Trifolium baccarinii (Fabaceae), one new semisynthetic derivative, 6-nitrobiochanin A (1b) and two known derivatives, 8-nitrobiochanin A (1a) and 2",3",4",6"-tetraacetylsissotrin (1c) have been obtained after performing nitration and acetylation reactions. Their structures were assigned after interpretation of their spectrometric (HR-ESI-MS) and spectroscopic (NMR 1D and 2D) data and by comparison with those reported in the literature. The substrate as well as the semisynthetic derivatives were evaluated for their antibacterial activities against six strains. The results reveal that they are inactive or weakly active on the strains tested with the exception of 8-nitrobiochanin A (1a) which showed moderate activity (MIC = 62.5 μg∙mL<sup>−1</sup>) on Staphylococcus aureus ATCC 43300.展开更多
The chemical study of <i>Rumex</i> <i>abyssinicus</i> Jacp (Polygonaceae) led to the iso<span>lation of a new ceramide named</span> (<i>R</i>)-2</span><span sty...The chemical study of <i>Rumex</i> <i>abyssinicus</i> Jacp (Polygonaceae) led to the iso<span>lation of a new ceramide named</span> (<i>R</i>)-2</span><span style="font-family:"">'</span><span style="font-family:"">-hydroxy-<i>N</i>-[(2<i>S</i>,3<i>S</i>,4<i>R</i>,16<i>E</i>)-1,3,4-trihy<span>droxyhexacos-16-en-2-yl]hexadecanamide (rumexamide) (<b>1</b>) together with</span> sixteen known compounds: bis-(2-ethylhexyl) phthalate (<b>2</b>), chrysophanol (<b>3</b>), physcion (<b>4</b>), citreorosein (<b>5</b>), emodin (<b>6</b>), chrysophanein (<b>7</b>), physcionin (<b>8</b>), <span>lupeol (<b>9</b>), 3<i>β</i>,28-dihydroxylup-20(29)-ene (<b>10</b>), 3<i>β</i>-dihydroxylup-</span>20(29)-en-28-oic acid (<b>11</b>), oleanolic acid (<b>12</b>), ergosta-6,22-diene-3,5,8-triol (<b>13</b>), stigmastane-3,6-dione (<b>14</b>), a mixture of <i>β</i>-sitosterol (<b>15</b>) and stigmasterol (<b>16</b>), and <span>stigmasterol 3-<i>O</i>-<i>β</i>-<i>D</i>-glucoside (<b>17</b>). Their structures were determined by </span>in<span>terpretation of their spectroscopic 1D NMR (<sup>1</sup>H and <sup>13</sup>C NMR), 2D NMR</span> (COSY <sup>1</sup>H-<sup>1</sup>H, HSQC and HMBC) data in conjunction with mass spectrometry<span> </span>(TOFESIMS and HR-TOFESIMS) and by comparison with those reported in the literature. Among all the known compounds, twelve <b>(2</b>, <b>5</b>, <b>8</b></span><b><span style="font-family:"">-</span></b><b><span style="font-family:"">17) </span></b><span style="font-family:"">were firstly isolated from <i>Rumex</i> <i>abyssinicus</i>, seven <b>(2, 10</b></span><b><span style="font-family:"">-</span></b><b><span style="font-family:"">14 and 17)</span></b><span style="font-family:""> from the genus <i>Rumex</i> and three (<b>13, 14, 17</b>) from family Polygonaceae. The <i>in</i> <i>vitro</i> antibacterial activities of extracts (MeOH, <i>n</i>-BuOH and EtOAc)</span><span style="font-family:"">,</span><span style="font-family:""> as well as compounds <b>9</b>, <b>11, 12</b>, <b>15</b></span><b><span style="font-family:""> </span></b><b><span style="font-family:"">+</span></b><b><span style="font-family:""> </span></b><b><span style="font-family:"">16</span></b><span style="font-family:""> and <b>17 </b>against pathogenic bacteria (<i>Staphylococcus</i> <i>aureus</i> ATCC 43300, <i>Shigella</i> <i>flexneri</i> NR 518, <i>Klebsiella</i> <i>pneumonia</i></span><i><span style="font-family:"">e</span></i><span style="font-family:""> ATCC 700603, <i>Escherichia</i> <i>coli</i> ATCC 25922)</span><span style="font-family:"">,</span><span style="font-family:""> were performed using </span><span style="font-family:"">the </span><span style="font-family:"">broth microdilution method and the results show that, extract</span><span style="font-family:"">s</span><span style="font-family:""> were not active (MIC </span><span style="font-family:"">></span><span style="font-family:""> </span><span style="font-family:"">1000 μg/mL) while compounds were weakly or not active (MIC ≥ 500 μg/mL) against all bacteria strains. Furthermore, the chemophenetic relationship</span><span style="font-family:"">s</span><span style="font-family:""> of the isolated compounds and their significance</span><span style="font-family:"">s</span><span style="font-family:""> were discussed.展开更多
Lannea kerstingii is known for its multiple therapeutic and biological activities. Despite of many traditional uses of this plant, scientific research on the content of its chemical compounds is still limited. This st...Lannea kerstingii is known for its multiple therapeutic and biological activities. Despite of many traditional uses of this plant, scientific research on the content of its chemical compounds is still limited. This study aims to isolate the chemical compounds contained in the n-butanol fraction of Lannea kerstingii leaves. The chemical investigation of the leaves of Lannea kerstingii led to isolation of three undescribed C-13 norisoprenoids, lankerstinol A-C (1-3), together with six (4-9) known flavonoid glycosides. The structures of these compounds were established by spectroscopic analyses.展开更多
A new flavonoid, acacetin-7-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranoside (1), together with four known flavonoids, apigenin-7-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranoside (2), acacetin (3), acace...A new flavonoid, acacetin-7-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranoside (1), together with four known flavonoids, apigenin-7-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranoside (2), acacetin (3), acacetin-7-O-β-D-glucuronide (4) and genkwanin-5-O-primveroside (5) were isolated from the leaves of Glyphaea brevis. Their structures were elucidated by spectroscopic techniques. The isolated compounds (1 - 5) were tested for their antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The tested compounds showed slight negative antioxidant activities against DPPH radicals.展开更多
Gouania longipetala Hemsl. (Rhamnaceae) is a medicinal plant from Côte d’Ivoire used to treat many diseases like malaria, gastrointestinal infections and gout. Scientific research of aerial part revealed the pre...Gouania longipetala Hemsl. (Rhamnaceae) is a medicinal plant from Côte d’Ivoire used to treat many diseases like malaria, gastrointestinal infections and gout. Scientific research of aerial part revealed the presence of triterpenoid compounds, saponins, phenolic compounds and flavonoids and also mentioned antibacterial, antioxydant and anti-inflammatory activities. Despite the various therapeutic uses of the plant, no scientific research mentions the chemical content of the root. So, this phytochemical investigation is made to identify secondary metabolites present in the hydromethanolic extract of its roots. And the research led to the isolation and characterization of three lupane-type triterpenoid compounds: a novel compound derived from gouanic acid, lupeol (1) and betulin (2), which had been previously reported in the literature. The newly discovered lupane-triterpenoid was identified as 1α-hydroxy-lup-20(29)-en-3-oxo-27,28-dioic acid (3). The structures of these compounds were determined based on analyses of spectroscopic data, including 1D-NMR, 2D-NMR and HR-ESI-MS techniques.展开更多
文摘From the ethyl acetate extract of the medicinal plant Graptophyllum glandulosum Turrill, five known compounds: Lupeol (1), Oleanolic acid (2), Chrysoeriol (3), N-methyl-isonicotinamide (4) and β-sitosterol 3-O-β-D-glucopyranoside (5) were isolated. In addition, oxidation reactions carried out on lupeol (1) yielded two semi-synthetic compounds, including a previously unreported: (20R)-formyloxy-29-nor-lupan-3-one (1b) and one other well-known Lupenone (1a). The structures of natural and semi-synthetic compounds were determined by analysis of 1D-(1H, 13C), 2D-(COSY, HSQC and HMBC) NMR data in conjunction with mass spectrometry (TOFESIMS and HR-TOFESIMS) and by comparison with the reported data. The evaluation of antimicrobial activities of substrate (1) as well as semi-synthetic derivatives (1a and 1b) using broth microdilution method showed that compound 1b was the most active (16 ≤ MIC ≤ 32 μg/mL) against Escherichia coli, Staphylococcus aureus and Candida albicans compared to the starting material 1 (16 ≤ MIC ≤ 64 μg/mL) and derivative 1a (32 ≤ MIC ≤ 64 μg/mL).
文摘Starting from sissotrin (1), a natural isoflavonoid isolated from Trifolium baccarinii (Fabaceae), one new semisynthetic derivative, 6-nitrobiochanin A (1b) and two known derivatives, 8-nitrobiochanin A (1a) and 2",3",4",6"-tetraacetylsissotrin (1c) have been obtained after performing nitration and acetylation reactions. Their structures were assigned after interpretation of their spectrometric (HR-ESI-MS) and spectroscopic (NMR 1D and 2D) data and by comparison with those reported in the literature. The substrate as well as the semisynthetic derivatives were evaluated for their antibacterial activities against six strains. The results reveal that they are inactive or weakly active on the strains tested with the exception of 8-nitrobiochanin A (1a) which showed moderate activity (MIC = 62.5 μg∙mL<sup>−1</sup>) on Staphylococcus aureus ATCC 43300.
文摘The chemical study of <i>Rumex</i> <i>abyssinicus</i> Jacp (Polygonaceae) led to the iso<span>lation of a new ceramide named</span> (<i>R</i>)-2</span><span style="font-family:"">'</span><span style="font-family:"">-hydroxy-<i>N</i>-[(2<i>S</i>,3<i>S</i>,4<i>R</i>,16<i>E</i>)-1,3,4-trihy<span>droxyhexacos-16-en-2-yl]hexadecanamide (rumexamide) (<b>1</b>) together with</span> sixteen known compounds: bis-(2-ethylhexyl) phthalate (<b>2</b>), chrysophanol (<b>3</b>), physcion (<b>4</b>), citreorosein (<b>5</b>), emodin (<b>6</b>), chrysophanein (<b>7</b>), physcionin (<b>8</b>), <span>lupeol (<b>9</b>), 3<i>β</i>,28-dihydroxylup-20(29)-ene (<b>10</b>), 3<i>β</i>-dihydroxylup-</span>20(29)-en-28-oic acid (<b>11</b>), oleanolic acid (<b>12</b>), ergosta-6,22-diene-3,5,8-triol (<b>13</b>), stigmastane-3,6-dione (<b>14</b>), a mixture of <i>β</i>-sitosterol (<b>15</b>) and stigmasterol (<b>16</b>), and <span>stigmasterol 3-<i>O</i>-<i>β</i>-<i>D</i>-glucoside (<b>17</b>). Their structures were determined by </span>in<span>terpretation of their spectroscopic 1D NMR (<sup>1</sup>H and <sup>13</sup>C NMR), 2D NMR</span> (COSY <sup>1</sup>H-<sup>1</sup>H, HSQC and HMBC) data in conjunction with mass spectrometry<span> </span>(TOFESIMS and HR-TOFESIMS) and by comparison with those reported in the literature. Among all the known compounds, twelve <b>(2</b>, <b>5</b>, <b>8</b></span><b><span style="font-family:"">-</span></b><b><span style="font-family:"">17) </span></b><span style="font-family:"">were firstly isolated from <i>Rumex</i> <i>abyssinicus</i>, seven <b>(2, 10</b></span><b><span style="font-family:"">-</span></b><b><span style="font-family:"">14 and 17)</span></b><span style="font-family:""> from the genus <i>Rumex</i> and three (<b>13, 14, 17</b>) from family Polygonaceae. The <i>in</i> <i>vitro</i> antibacterial activities of extracts (MeOH, <i>n</i>-BuOH and EtOAc)</span><span style="font-family:"">,</span><span style="font-family:""> as well as compounds <b>9</b>, <b>11, 12</b>, <b>15</b></span><b><span style="font-family:""> </span></b><b><span style="font-family:"">+</span></b><b><span style="font-family:""> </span></b><b><span style="font-family:"">16</span></b><span style="font-family:""> and <b>17 </b>against pathogenic bacteria (<i>Staphylococcus</i> <i>aureus</i> ATCC 43300, <i>Shigella</i> <i>flexneri</i> NR 518, <i>Klebsiella</i> <i>pneumonia</i></span><i><span style="font-family:"">e</span></i><span style="font-family:""> ATCC 700603, <i>Escherichia</i> <i>coli</i> ATCC 25922)</span><span style="font-family:"">,</span><span style="font-family:""> were performed using </span><span style="font-family:"">the </span><span style="font-family:"">broth microdilution method and the results show that, extract</span><span style="font-family:"">s</span><span style="font-family:""> were not active (MIC </span><span style="font-family:"">></span><span style="font-family:""> </span><span style="font-family:"">1000 μg/mL) while compounds were weakly or not active (MIC ≥ 500 μg/mL) against all bacteria strains. Furthermore, the chemophenetic relationship</span><span style="font-family:"">s</span><span style="font-family:""> of the isolated compounds and their significance</span><span style="font-family:"">s</span><span style="font-family:""> were discussed.
文摘Lannea kerstingii is known for its multiple therapeutic and biological activities. Despite of many traditional uses of this plant, scientific research on the content of its chemical compounds is still limited. This study aims to isolate the chemical compounds contained in the n-butanol fraction of Lannea kerstingii leaves. The chemical investigation of the leaves of Lannea kerstingii led to isolation of three undescribed C-13 norisoprenoids, lankerstinol A-C (1-3), together with six (4-9) known flavonoid glycosides. The structures of these compounds were established by spectroscopic analyses.
文摘A new flavonoid, acacetin-7-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranoside (1), together with four known flavonoids, apigenin-7-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranoside (2), acacetin (3), acacetin-7-O-β-D-glucuronide (4) and genkwanin-5-O-primveroside (5) were isolated from the leaves of Glyphaea brevis. Their structures were elucidated by spectroscopic techniques. The isolated compounds (1 - 5) were tested for their antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The tested compounds showed slight negative antioxidant activities against DPPH radicals.
文摘Gouania longipetala Hemsl. (Rhamnaceae) is a medicinal plant from Côte d’Ivoire used to treat many diseases like malaria, gastrointestinal infections and gout. Scientific research of aerial part revealed the presence of triterpenoid compounds, saponins, phenolic compounds and flavonoids and also mentioned antibacterial, antioxydant and anti-inflammatory activities. Despite the various therapeutic uses of the plant, no scientific research mentions the chemical content of the root. So, this phytochemical investigation is made to identify secondary metabolites present in the hydromethanolic extract of its roots. And the research led to the isolation and characterization of three lupane-type triterpenoid compounds: a novel compound derived from gouanic acid, lupeol (1) and betulin (2), which had been previously reported in the literature. The newly discovered lupane-triterpenoid was identified as 1α-hydroxy-lup-20(29)-en-3-oxo-27,28-dioic acid (3). The structures of these compounds were determined based on analyses of spectroscopic data, including 1D-NMR, 2D-NMR and HR-ESI-MS techniques.
