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Synthesis, Modification and Biological Activity of Diosgenyl β-d-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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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2020-11, Vol.25 (22), p.5433 |
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| container_issue | 22 |
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| creator | Grzywacz, Daria Liberek, Beata Myszka, Henryk |
| 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-d-glycosaminosides (d-gluco and d-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different
-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-d-glycosaminosides, associated with functionalisation of the amino group. These provide
-acyl,
-alkyl,
-dialkyl,
-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented. |
| doi_str_mv | 10.3390/molecules25225433 |
| format | article |
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-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-d-glycosaminosides, associated with functionalisation of the amino group. These provide
-acyl,
-alkyl,
-dialkyl,
-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules25225433</identifier><identifier>PMID: 33233558</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>amine group modifications ; Amines - chemistry ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; antimicrobial activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological activity ; Biological effects ; Cancer ; Carbohydrates ; Carbon ; Chemical Phenomena ; Chemistry Techniques, Synthetic ; Chromatography ; diosgenin glycosides ; diosgenyl β- d -galactosaminoside ; diosgenyl β- d -glucosaminoside ; Folk medicine ; Fungicides ; Glucose ; Glycosides ; Hemolysis ; Humans ; Hydrophobicity ; Molecular Structure ; Protecting groups ; Review ; Saponins ; Saponins - chemical synthesis ; Saponins - chemistry ; Saponins - pharmacology ; Solvent extraction processes ; steroid saponin ; Steroids ; Structure-Activity Relationship</subject><ispartof>Molecules (Basel, Switzerland), 2020-11, Vol.25 (22), p.5433</ispartof><rights>2020. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2020 by the authors. 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c493t-22a8ceaa9ee8b62d19ab1d39e3401e3e3a4b86bfcf67558e40da049ff54323d33</citedby><cites>FETCH-LOGICAL-c493t-22a8ceaa9ee8b62d19ab1d39e3401e3e3a4b86bfcf67558e40da049ff54323d33</cites><orcidid>0000-0001-7661-308X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2464270514/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2464270514?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33233558$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Grzywacz, Daria</creatorcontrib><creatorcontrib>Liberek, Beata</creatorcontrib><creatorcontrib>Myszka, Henryk</creatorcontrib><title>Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><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-d-glycosaminosides (d-gluco and d-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different
-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-d-glycosaminosides, associated with functionalisation of the amino group. These provide
-acyl,
-alkyl,
-dialkyl,
-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented.</description><subject>amine group modifications</subject><subject>Amines - chemistry</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antimicrobial activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological activity</subject><subject>Biological effects</subject><subject>Cancer</subject><subject>Carbohydrates</subject><subject>Carbon</subject><subject>Chemical Phenomena</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Chromatography</subject><subject>diosgenin glycosides</subject><subject>diosgenyl β- d -galactosaminoside</subject><subject>diosgenyl β- d -glucosaminoside</subject><subject>Folk medicine</subject><subject>Fungicides</subject><subject>Glucose</subject><subject>Glycosides</subject><subject>Hemolysis</subject><subject>Humans</subject><subject>Hydrophobicity</subject><subject>Molecular Structure</subject><subject>Protecting groups</subject><subject>Review</subject><subject>Saponins</subject><subject>Saponins - chemical synthesis</subject><subject>Saponins - chemistry</subject><subject>Saponins - pharmacology</subject><subject>Solvent extraction processes</subject><subject>steroid saponin</subject><subject>Steroids</subject><subject>Structure-Activity Relationship</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplks9uFDEMxkcIREvhAbigkbhwYCCJM3_CAWkpUCoV9QCco0zibLPKJCWZXTSvxYPwTIRuqVo4JbI__-TPdlU9peQVgCCvp-hRbz1m1jLWcoB71SHljDRAuLh_639QPcp5QwijnLYPqwMABtC2w2ElvyxhvsDs8sv6czTOOq1mF0OtgqnfuejjukR8vdKz27l5qaOt37uY1xgWX__62ZjmxC86ZjW5ELMzmN_Uq1Cf7zDtHP54XD2wymd8cv0eVd8-fvh6_Kk5Oz85PV6dNZoLmBvG1KBRKYE4jB0zVKiRGhAInFAEBMXHoRuttl1f-kZOjCq-rC2uGRiAo-p0zzVRbeRlcpNKi4zKyatATGup0uy0R9np1moOvRlsx4k1CgtaYT9gq5imQ2G93bMut-OERmOYk_J3oHczwV3IddzJvhOiG0QBvLgGpPh9i3mWk8savVcB4zZLxjtOBcDAivT5P9JN3KZQRnWlYj1pKS8qulfpFHNOaG-aoUT-OQX53ymUmme3XdxU_N09_AZgXbQ4</recordid><startdate>20201120</startdate><enddate>20201120</enddate><creator>Grzywacz, Daria</creator><creator>Liberek, Beata</creator><creator>Myszka, Henryk</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-7661-308X</orcidid></search><sort><creationdate>20201120</creationdate><title>Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview</title><author>Grzywacz, Daria ; Liberek, Beata ; Myszka, Henryk</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c493t-22a8ceaa9ee8b62d19ab1d39e3401e3e3a4b86bfcf67558e40da049ff54323d33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>amine group modifications</topic><topic>Amines - chemistry</topic><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antimicrobial activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological activity</topic><topic>Biological effects</topic><topic>Cancer</topic><topic>Carbohydrates</topic><topic>Carbon</topic><topic>Chemical Phenomena</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Chromatography</topic><topic>diosgenin glycosides</topic><topic>diosgenyl β- d -galactosaminoside</topic><topic>diosgenyl β- d -glucosaminoside</topic><topic>Folk medicine</topic><topic>Fungicides</topic><topic>Glucose</topic><topic>Glycosides</topic><topic>Hemolysis</topic><topic>Humans</topic><topic>Hydrophobicity</topic><topic>Molecular Structure</topic><topic>Protecting groups</topic><topic>Review</topic><topic>Saponins</topic><topic>Saponins - chemical synthesis</topic><topic>Saponins - chemistry</topic><topic>Saponins - pharmacology</topic><topic>Solvent extraction processes</topic><topic>steroid saponin</topic><topic>Steroids</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Grzywacz, Daria</creatorcontrib><creatorcontrib>Liberek, Beata</creatorcontrib><creatorcontrib>Myszka, Henryk</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Grzywacz, Daria</au><au>Liberek, Beata</au><au>Myszka, Henryk</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2020-11-20</date><risdate>2020</risdate><volume>25</volume><issue>22</issue><spage>5433</spage><pages>5433-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>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-d-glycosaminosides (d-gluco and d-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different
-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-d-glycosaminosides, associated with functionalisation of the amino group. These provide
-acyl,
-alkyl,
-dialkyl,
-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>33233558</pmid><doi>10.3390/molecules25225433</doi><orcidid>https://orcid.org/0000-0001-7661-308X</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Molecules (Basel, Switzerland), 2020-11, Vol.25 (22), p.5433 |
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| source | Publicly Available Content Database; PubMed Central |
| subjects | amine group modifications Amines - chemistry Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology antimicrobial activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological activity Biological effects Cancer Carbohydrates Carbon Chemical Phenomena Chemistry Techniques, Synthetic Chromatography diosgenin glycosides diosgenyl β- d -galactosaminoside diosgenyl β- d -glucosaminoside Folk medicine Fungicides Glucose Glycosides Hemolysis Humans Hydrophobicity Molecular Structure Protecting groups Review Saponins Saponins - chemical synthesis Saponins - chemistry Saponins - pharmacology Solvent extraction processes steroid saponin Steroids Structure-Activity Relationship |
| title | Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview |
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