Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An Overview
Saponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponin...
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| Format: | Article |
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MDPI AG
2020-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/22/5433 |
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| author | Daria Grzywacz Beata Liberek Henryk Myszka |
| author_facet | Daria Grzywacz Beata Liberek Henryk Myszka |
| author_sort | Daria Grzywacz |
| collection | DOAJ |
| description | Saponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponins, and many of them exhibit various pharmacological properties. Herein, we present an overview of semisynthetic saponins syntheses–diosgenyl β-<span style="font-variant: small-caps;">d</span>-glycosaminosides (<span style="font-variant: small-caps;">d</span>-gluco and <span style="font-variant: small-caps;">d</span>-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different <i>N</i>-protecting groups and various reaction conditions used for their synthesis are presented. In addition, this paper demonstrates the possibilities of chemical modifications of diosgenyl β-<span style="font-variant: small-caps;">d</span>-glycosaminosides, associated with functionalisation of the amino group. These provide <i>N</i>-acyl, <i>N</i>-alkyl, <i>N,N</i>-dialkyl, <i>N</i>-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-<span style="font-variant: small-caps;">d</span>-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented. |
| first_indexed | 2024-03-10T14:42:53Z |
| format | Article |
| id | doaj.art-6c5fc437d8f640fdaeb86ae78e5a2c18 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T14:42:53Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-6c5fc437d8f640fdaeb86ae78e5a2c182023-11-20T21:39:31ZengMDPI AGMolecules1420-30492020-11-012522543310.3390/molecules25225433Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An OverviewDaria Grzywacz0Beata Liberek1Henryk Myszka2Laboratory of Glycochemistry, Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, PolandLaboratory of Glycochemistry, Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, PolandLaboratory of Glycochemistry, Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, PolandSaponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponins, and many of them exhibit various pharmacological properties. Herein, we present an overview of semisynthetic saponins syntheses–diosgenyl β-<span style="font-variant: small-caps;">d</span>-glycosaminosides (<span style="font-variant: small-caps;">d</span>-gluco and <span style="font-variant: small-caps;">d</span>-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different <i>N</i>-protecting groups and various reaction conditions used for their synthesis are presented. In addition, this paper demonstrates the possibilities of chemical modifications of diosgenyl β-<span style="font-variant: small-caps;">d</span>-glycosaminosides, associated with functionalisation of the amino group. These provide <i>N</i>-acyl, <i>N</i>-alkyl, <i>N,N</i>-dialkyl, <i>N</i>-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-<span style="font-variant: small-caps;">d</span>-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented.https://www.mdpi.com/1420-3049/25/22/5433steroid saponindiosgenin glycosidesdiosgenyl β-<span style="font-variant: small-caps">d</span>-glucosaminosidediosgenyl β-<span style="font-variant: small-caps">d</span>-galactosaminosideamine group modificationsantimicrobial activity |
| spellingShingle | Daria Grzywacz Beata Liberek Henryk Myszka Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An Overview Molecules steroid saponin diosgenin glycosides diosgenyl β-<span style="font-variant: small-caps">d</span>-glucosaminoside diosgenyl β-<span style="font-variant: small-caps">d</span>-galactosaminoside amine group modifications antimicrobial activity |
| title | Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An Overview |
| title_full | Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An Overview |
| title_fullStr | Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An Overview |
| title_full_unstemmed | Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An Overview |
| title_short | Synthesis, Modification and Biological Activity of Diosgenyl β-<span style="font-variant: small-caps">d</span>-Glycosaminosides: An Overview |
| title_sort | synthesis modification and biological activity of diosgenyl β span style font variant small caps d span glycosaminosides an overview |
| topic | steroid saponin diosgenin glycosides diosgenyl β-<span style="font-variant: small-caps">d</span>-glucosaminoside diosgenyl β-<span style="font-variant: small-caps">d</span>-galactosaminoside amine group modifications antimicrobial activity |
| url | https://www.mdpi.com/1420-3049/25/22/5433 |
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