New acylated triterpenoid saponins from the roots of Acacia polyacantha Willd. (Fabaceae)
In our continuing search of saponins from the plants of Fabaceae family, phytochemical investigation of the roots of Acacia polyacantha, led to the isolation and structural characterization of six undescribed triterpenoid saponins, named polyacosides A-F (1–6). Their structures were established, usi...
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| Veröffentlicht in: | Carbohydrate research 2023-01, Vol.523, p.108725-108725, Article 108725 |
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| creator | Atangana, Jean Faustin Messi, Lin Marcellin Haddad, Mohamed Mbing, Joséphine Ngo Boyogueno Begoude, Aime-Didier Pegnyemb, Dieudonné Emmanuel Choudhary, Muhammad Iqbal Noté, Olivier Placide |
| description | In our continuing search of saponins from the plants of Fabaceae family, phytochemical investigation of the roots of Acacia polyacantha, led to the isolation and structural characterization of six undescribed triterpenoid saponins, named polyacosides A-F (1–6). Their structures were established, using extensive analysis by NMR techniques, mainly 1D NMR (1H, 13C, and DEPT) and 2D NMR (COSY, NOESY, HSQC, TOCSY and HMBC) experiments, HRESIMS and by comparison with the literature data, as 3-O-[β-d-xylopyranosyl-(1 → 4)- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)]-α-l-arabinopyranosyl]-21-O-[Cis-2-methoxycinnamoyl] machaerinic acid (1), 3-O-[β-d-xylopyranosyl-(1 → 4)- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)]-α-l-arabinopyranosyl]-21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid. (2), 3-O- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl]-21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (3), 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid (4), 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Cis-2-methoxycinnamoyl] machaerinic acid (5) and 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (6). Our findings highlight the presence of methoxycinnamoyl group linked to C-21 of the machaerinic acid aglycone moiety as first report of 21-methoxycinnamoyl-machaerinic acid derivative from the plants of Acacia genus (Fabaceae). This represents therefore a valuable contribution to the chemotaxonomy of the Acacia genus of Fabaceae family, which is known to be a rich source of triterpenoid saponins.
[Display omitted]
•Six new acylated triterpenoid saponins isolated from the roots of Acacia polyacantha wild.•Their structures were elucidated using chemical methods and spectroscopic analysis.•The presence of a methoxycinnamoyl group attached at C-21 of machaerinic acid unit, as aglycon is resported. |
| doi_str_mv | 10.1016/j.carres.2022.108725 |
| format | Article |
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[Display omitted]
•Six new acylated triterpenoid saponins isolated from the roots of Acacia polyacantha wild.•Their structures were elucidated using chemical methods and spectroscopic analysis.•The presence of a methoxycinnamoyl group attached at C-21 of machaerinic acid unit, as aglycon is resported.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>EISSN: 0008-6215</identifier><identifier>DOI: 10.1016/j.carres.2022.108725</identifier><identifier>PMID: 36455425</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Acacia - chemistry ; Acacia polyacantha ; Acylated triterpenoid saponins ; Fabaceae ; Life Sciences ; Molecular Structure ; NMR ; Plant Roots - chemistry ; Polyacosides ; Saponins - chemistry ; Triterpenes - chemistry</subject><ispartof>Carbohydrate research, 2023-01, Vol.523, p.108725-108725, Article 108725</ispartof><rights>2022 Elsevier Ltd</rights><rights>Copyright © 2022 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c396t-de2a0b69eb980bcb5af9f44e3773b02fd801d5188279a7ebdd5df46454e92cd03</citedby><cites>FETCH-LOGICAL-c396t-de2a0b69eb980bcb5af9f44e3773b02fd801d5188279a7ebdd5df46454e92cd03</cites><orcidid>0000-0002-9483-0579</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.carres.2022.108725$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36455425$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://ut3-toulouseinp.hal.science/hal-04726091$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Atangana, Jean Faustin</creatorcontrib><creatorcontrib>Messi, Lin Marcellin</creatorcontrib><creatorcontrib>Haddad, Mohamed</creatorcontrib><creatorcontrib>Mbing, Joséphine Ngo</creatorcontrib><creatorcontrib>Boyogueno Begoude, Aime-Didier</creatorcontrib><creatorcontrib>Pegnyemb, Dieudonné Emmanuel</creatorcontrib><creatorcontrib>Choudhary, Muhammad Iqbal</creatorcontrib><creatorcontrib>Noté, Olivier Placide</creatorcontrib><title>New acylated triterpenoid saponins from the roots of Acacia polyacantha Willd. (Fabaceae)</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>In our continuing search of saponins from the plants of Fabaceae family, phytochemical investigation of the roots of Acacia polyacantha, led to the isolation and structural characterization of six undescribed triterpenoid saponins, named polyacosides A-F (1–6). Their structures were established, using extensive analysis by NMR techniques, mainly 1D NMR (1H, 13C, and DEPT) and 2D NMR (COSY, NOESY, HSQC, TOCSY and HMBC) experiments, HRESIMS and by comparison with the literature data, as 3-O-[β-d-xylopyranosyl-(1 → 4)- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)]-α-l-arabinopyranosyl]-21-O-[Cis-2-methoxycinnamoyl] machaerinic acid (1), 3-O-[β-d-xylopyranosyl-(1 → 4)- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)]-α-l-arabinopyranosyl]-21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid. (2), 3-O- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl]-21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (3), 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid (4), 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Cis-2-methoxycinnamoyl] machaerinic acid (5) and 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (6). Our findings highlight the presence of methoxycinnamoyl group linked to C-21 of the machaerinic acid aglycone moiety as first report of 21-methoxycinnamoyl-machaerinic acid derivative from the plants of Acacia genus (Fabaceae). This represents therefore a valuable contribution to the chemotaxonomy of the Acacia genus of Fabaceae family, which is known to be a rich source of triterpenoid saponins.
[Display omitted]
•Six new acylated triterpenoid saponins isolated from the roots of Acacia polyacantha wild.•Their structures were elucidated using chemical methods and spectroscopic analysis.•The presence of a methoxycinnamoyl group attached at C-21 of machaerinic acid unit, as aglycon is resported.</description><subject>Acacia - chemistry</subject><subject>Acacia polyacantha</subject><subject>Acylated triterpenoid saponins</subject><subject>Fabaceae</subject><subject>Life Sciences</subject><subject>Molecular Structure</subject><subject>NMR</subject><subject>Plant Roots - chemistry</subject><subject>Polyacosides</subject><subject>Saponins - chemistry</subject><subject>Triterpenes - chemistry</subject><issn>0008-6215</issn><issn>1873-426X</issn><issn>0008-6215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU9v1DAQxS0EotvCN0DIx_aQxXb8J7kgrSpKkVZwAQEna2JPtF5l42B7i_bbk1XaHjmNZvSb90bzCHnH2Zozrj_s1w5SwrwWTIh51BihXpAVb0xdSaF_vSQrxlhTacHVBbnMeT-3TBv9mlzUWiolhVqR31_xLwV3GqCgpyWFgmnCMQZPM0xxDGOmfYoHWnZIU4wl09jTjQMXgE5xOIGDseyA_gzD4Nf0-g46cAh484a86mHI-PaxXpEfd5--395X22-fv9xutpWrW10qjwJYp1vs2oZ1rlPQt72UWBtTd0z0vmHcK940wrRgsPNe-V7O90tshfOsviI3i-4OBjulcIB0shGCvd9s7XnGpBGatfyBz-z1wk4p_jliLvYQssNhgBHjMVthpK5boVg9o3JBXYo5J-yftTmz5wDs3i4B2HMAdglgXnv_6HDsDuifl54-PgMfFwDnnzwETDa7gKNDHxK6Yn0M_3f4B5p7l-o</recordid><startdate>202301</startdate><enddate>202301</enddate><creator>Atangana, Jean Faustin</creator><creator>Messi, Lin Marcellin</creator><creator>Haddad, Mohamed</creator><creator>Mbing, Joséphine Ngo</creator><creator>Boyogueno Begoude, Aime-Didier</creator><creator>Pegnyemb, Dieudonné Emmanuel</creator><creator>Choudhary, Muhammad Iqbal</creator><creator>Noté, Olivier Placide</creator><general>Elsevier Ltd</general><general>Elsevier</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>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-9483-0579</orcidid></search><sort><creationdate>202301</creationdate><title>New acylated triterpenoid saponins from the roots of Acacia polyacantha Willd. (Fabaceae)</title><author>Atangana, Jean Faustin ; Messi, Lin Marcellin ; Haddad, Mohamed ; Mbing, Joséphine Ngo ; Boyogueno Begoude, Aime-Didier ; Pegnyemb, Dieudonné Emmanuel ; Choudhary, Muhammad Iqbal ; Noté, Olivier Placide</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-de2a0b69eb980bcb5af9f44e3773b02fd801d5188279a7ebdd5df46454e92cd03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acacia - chemistry</topic><topic>Acacia polyacantha</topic><topic>Acylated triterpenoid saponins</topic><topic>Fabaceae</topic><topic>Life Sciences</topic><topic>Molecular Structure</topic><topic>NMR</topic><topic>Plant Roots - chemistry</topic><topic>Polyacosides</topic><topic>Saponins - chemistry</topic><topic>Triterpenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Atangana, Jean Faustin</creatorcontrib><creatorcontrib>Messi, Lin Marcellin</creatorcontrib><creatorcontrib>Haddad, Mohamed</creatorcontrib><creatorcontrib>Mbing, Joséphine Ngo</creatorcontrib><creatorcontrib>Boyogueno Begoude, Aime-Didier</creatorcontrib><creatorcontrib>Pegnyemb, Dieudonné Emmanuel</creatorcontrib><creatorcontrib>Choudhary, Muhammad Iqbal</creatorcontrib><creatorcontrib>Noté, Olivier Placide</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Atangana, Jean Faustin</au><au>Messi, Lin Marcellin</au><au>Haddad, Mohamed</au><au>Mbing, Joséphine Ngo</au><au>Boyogueno Begoude, Aime-Didier</au><au>Pegnyemb, Dieudonné Emmanuel</au><au>Choudhary, Muhammad Iqbal</au><au>Noté, Olivier Placide</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New acylated triterpenoid saponins from the roots of Acacia polyacantha Willd. (Fabaceae)</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2023-01</date><risdate>2023</risdate><volume>523</volume><spage>108725</spage><epage>108725</epage><pages>108725-108725</pages><artnum>108725</artnum><issn>0008-6215</issn><eissn>1873-426X</eissn><eissn>0008-6215</eissn><abstract>In our continuing search of saponins from the plants of Fabaceae family, phytochemical investigation of the roots of Acacia polyacantha, led to the isolation and structural characterization of six undescribed triterpenoid saponins, named polyacosides A-F (1–6). Their structures were established, using extensive analysis by NMR techniques, mainly 1D NMR (1H, 13C, and DEPT) and 2D NMR (COSY, NOESY, HSQC, TOCSY and HMBC) experiments, HRESIMS and by comparison with the literature data, as 3-O-[β-d-xylopyranosyl-(1 → 4)- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)]-α-l-arabinopyranosyl]-21-O-[Cis-2-methoxycinnamoyl] machaerinic acid (1), 3-O-[β-d-xylopyranosyl-(1 → 4)- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)]-α-l-arabinopyranosyl]-21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid. (2), 3-O- [β-d-galactopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl]-21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (3), 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid (4), 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Cis-2-methoxycinnamoyl] machaerinic acid (5) and 3-O- [β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl] -21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (6). Our findings highlight the presence of methoxycinnamoyl group linked to C-21 of the machaerinic acid aglycone moiety as first report of 21-methoxycinnamoyl-machaerinic acid derivative from the plants of Acacia genus (Fabaceae). This represents therefore a valuable contribution to the chemotaxonomy of the Acacia genus of Fabaceae family, which is known to be a rich source of triterpenoid saponins.
[Display omitted]
•Six new acylated triterpenoid saponins isolated from the roots of Acacia polyacantha wild.•Their structures were elucidated using chemical methods and spectroscopic analysis.•The presence of a methoxycinnamoyl group attached at C-21 of machaerinic acid unit, as aglycon is resported.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>36455425</pmid><doi>10.1016/j.carres.2022.108725</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-9483-0579</orcidid></addata></record> |
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| subjects | Acacia - chemistry Acacia polyacantha Acylated triterpenoid saponins Fabaceae Life Sciences Molecular Structure NMR Plant Roots - chemistry Polyacosides Saponins - chemistry Triterpenes - chemistry |
| title | New acylated triterpenoid saponins from the roots of Acacia polyacantha Willd. (Fabaceae) |
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