Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic Significance
Four polyoxygenated stigmastanes (<b>1</b>–<b>4</b>) alongside known analogues (<b>7</b>–<b>8</b>) and flavonoids (<b>5</b>–<b>6</b>) were isolated from a dichloromethane/methanol (1:1, <i>v</i>/<i>v</i>)...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/5278 |
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| author | Nadine Tseme Wandji Gabin Thierry M. Bitchagno Isabelle Mawabo Kamga Joseph Tchamgoue Celine Nguefeu Nkenfou Bruno Ndjakou Lenta Norbert Sewald Simeon Fogue Kouam |
| author_facet | Nadine Tseme Wandji Gabin Thierry M. Bitchagno Isabelle Mawabo Kamga Joseph Tchamgoue Celine Nguefeu Nkenfou Bruno Ndjakou Lenta Norbert Sewald Simeon Fogue Kouam |
| author_sort | Nadine Tseme Wandji |
| collection | DOAJ |
| description | Four polyoxygenated stigmastanes (<b>1</b>–<b>4</b>) alongside known analogues (<b>7</b>–<b>8</b>) and flavonoids (<b>5</b>–<b>6</b>) were isolated from a dichloromethane/methanol (1:1, <i>v</i>/<i>v</i>) extract of the whole plant of <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. (Asteraceae). Their structures were determined by means of spectroscopic and spectrometric analysis. The relative stereochemistry of the new compounds was established and confirmed via biosynthesis evidence and cyclization of <b>1</b> under acidic conditions. A plausible biosynthetic pathway to the new compounds and the chemophenetic significance of the isolated constituents were also discussed. The crude extract, fractions, and compounds (<b>1</b>–<b>3</b>) were assessed for their antibacterial activity against five highly prevalent bacterial strains. The fractions and compounds showed low to moderate activity with minimal inhibitory concentrations (MICs) > 125 µg/mL. |
| first_indexed | 2024-03-11T01:33:33Z |
| format | Article |
| id | doaj.art-b911ee8772044b4e94e77c9382673d72 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:33:33Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b911ee8772044b4e94e77c9382673d722023-11-18T17:10:49ZengMDPI AGMolecules1420-30492023-07-012813527810.3390/molecules28135278Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic SignificanceNadine Tseme Wandji0Gabin Thierry M. Bitchagno1Isabelle Mawabo Kamga2Joseph Tchamgoue3Celine Nguefeu Nkenfou4Bruno Ndjakou Lenta5Norbert Sewald6Simeon Fogue Kouam7Department of Chemistry, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, CameroonOrganic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, GermanyDepartment of Biology, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, CameroonDepartment of Chemistry, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, CameroonDepartment of Biology, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, CameroonDepartment of Chemistry, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, CameroonOrganic and Bioorganic Chemistry, Faculty of Chemistry, Bielefeld University, D-33501 Bielefeld, GermanyDepartment of Chemistry, Higher Teacher Training College, University of Yaounde I, Yaounde P.O. Box 47, CameroonFour polyoxygenated stigmastanes (<b>1</b>–<b>4</b>) alongside known analogues (<b>7</b>–<b>8</b>) and flavonoids (<b>5</b>–<b>6</b>) were isolated from a dichloromethane/methanol (1:1, <i>v</i>/<i>v</i>) extract of the whole plant of <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. (Asteraceae). Their structures were determined by means of spectroscopic and spectrometric analysis. The relative stereochemistry of the new compounds was established and confirmed via biosynthesis evidence and cyclization of <b>1</b> under acidic conditions. A plausible biosynthetic pathway to the new compounds and the chemophenetic significance of the isolated constituents were also discussed. The crude extract, fractions, and compounds (<b>1</b>–<b>3</b>) were assessed for their antibacterial activity against five highly prevalent bacterial strains. The fractions and compounds showed low to moderate activity with minimal inhibitory concentrations (MICs) > 125 µg/mL.https://www.mdpi.com/1420-3049/28/13/5278<i>Vernonia kotschyana</i>Asteraceaestigmastanesstructure elucidationchemophenetic significanceantibacterial activity |
| spellingShingle | Nadine Tseme Wandji Gabin Thierry M. Bitchagno Isabelle Mawabo Kamga Joseph Tchamgoue Celine Nguefeu Nkenfou Bruno Ndjakou Lenta Norbert Sewald Simeon Fogue Kouam Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic Significance Molecules <i>Vernonia kotschyana</i> Asteraceae stigmastanes structure elucidation chemophenetic significance antibacterial activity |
| title | Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic Significance |
| title_full | Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic Significance |
| title_fullStr | Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic Significance |
| title_full_unstemmed | Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic Significance |
| title_short | Polyoxygenated Stigmastane-Type Steroids from <i>Vernonia kotschyana</i> Sch. Bip. ex Walp. and Their Chemophenetic Significance |
| title_sort | polyoxygenated stigmastane type steroids from i vernonia kotschyana i sch bip ex walp and their chemophenetic significance |
| topic | <i>Vernonia kotschyana</i> Asteraceae stigmastanes structure elucidation chemophenetic significance antibacterial activity |
| url | https://www.mdpi.com/1420-3049/28/13/5278 |
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