6-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized Metabolites
Identifying novel phytochemical secondary metabolites following classical pharmacognostic investigations is tedious and often involves repetitive chromatographic efforts. During the past decade, Ultra-High Performance Liquid Chromatography-Quadrupole Time of Flight-Tandem Mass Spectrometry (UHPLC-QT...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-07-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/14/11487 |
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| author | Bharathi Avula Ji-Yeong Bae Jongmin Ahn Kumar Katragunta Yan-Hong Wang Mei Wang Yongsoo Kwon Ikhlas A. Khan Amar G. Chittiboyina |
| author_facet | Bharathi Avula Ji-Yeong Bae Jongmin Ahn Kumar Katragunta Yan-Hong Wang Mei Wang Yongsoo Kwon Ikhlas A. Khan Amar G. Chittiboyina |
| author_sort | Bharathi Avula |
| collection | DOAJ |
| description | Identifying novel phytochemical secondary metabolites following classical pharmacognostic investigations is tedious and often involves repetitive chromatographic efforts. During the past decade, Ultra-High Performance Liquid Chromatography-Quadrupole Time of Flight-Tandem Mass Spectrometry (UHPLC-QToF-MS/MS), in combination with molecular networking, has been successfully demonstrated for the rapid dereplication of novel natural products in complex mixtures. As a logical application of such innovative tools in botanical research, more than 40 unique 3-oxy-, 3, 6-dioxy-, and 3, 6, 27-trioxy-steroidal saponins were identified in aerial parts and rhizomes of botanically verified <i>Smilax sieboldii</i>. Tandem mass diagnostic fragmentation patterns of aglycones, diosgenin, sarsasapogenin/tigogenin, or laxogenin were critical to establishing the unique nodes belonging to six groups of nineteen unknown steroidal saponins identified in <i>S. sieboldii</i>. Mass fragmentation analysis resulted in the identification of 6-hydroxy sapogenins, believed to be key precursors in the biogenesis of characteristic smilaxins and sieboldins, along with other saponins identified within <i>S. sieboldii</i>. These analytes’ relative biodistribution and characteristic molecular networking profiles were established by analyzing the leaf, stem, and root/rhizome of <i>S. sieboldii</i>. Deducing such profiles is anticipated to aid the overall product integrity of botanical dietary supplements while avoiding tedious pharmacognostic investigations and helping identify exogenous components within the finished products. |
| first_indexed | 2024-03-11T01:00:25Z |
| format | Article |
| id | doaj.art-2bd4c172010649dc90d1a3fec671ba4a |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-11T01:00:25Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-2bd4c172010649dc90d1a3fec671ba4a2023-11-18T19:40:14ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-07-0124141148710.3390/ijms2414114876-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized MetabolitesBharathi Avula0Ji-Yeong Bae1Jongmin Ahn2Kumar Katragunta3Yan-Hong Wang4Mei Wang5Yongsoo Kwon6Ikhlas A. Khan7Amar G. Chittiboyina8National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USANational Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS 38677, USAIdentifying novel phytochemical secondary metabolites following classical pharmacognostic investigations is tedious and often involves repetitive chromatographic efforts. During the past decade, Ultra-High Performance Liquid Chromatography-Quadrupole Time of Flight-Tandem Mass Spectrometry (UHPLC-QToF-MS/MS), in combination with molecular networking, has been successfully demonstrated for the rapid dereplication of novel natural products in complex mixtures. As a logical application of such innovative tools in botanical research, more than 40 unique 3-oxy-, 3, 6-dioxy-, and 3, 6, 27-trioxy-steroidal saponins were identified in aerial parts and rhizomes of botanically verified <i>Smilax sieboldii</i>. Tandem mass diagnostic fragmentation patterns of aglycones, diosgenin, sarsasapogenin/tigogenin, or laxogenin were critical to establishing the unique nodes belonging to six groups of nineteen unknown steroidal saponins identified in <i>S. sieboldii</i>. Mass fragmentation analysis resulted in the identification of 6-hydroxy sapogenins, believed to be key precursors in the biogenesis of characteristic smilaxins and sieboldins, along with other saponins identified within <i>S. sieboldii</i>. These analytes’ relative biodistribution and characteristic molecular networking profiles were established by analyzing the leaf, stem, and root/rhizome of <i>S. sieboldii</i>. Deducing such profiles is anticipated to aid the overall product integrity of botanical dietary supplements while avoiding tedious pharmacognostic investigations and helping identify exogenous components within the finished products.https://www.mdpi.com/1422-0067/24/14/11487phytochemicalssteroidal saponinshyphenated methodsliquid chromatographymolecular networking |
| spellingShingle | Bharathi Avula Ji-Yeong Bae Jongmin Ahn Kumar Katragunta Yan-Hong Wang Mei Wang Yongsoo Kwon Ikhlas A. Khan Amar G. Chittiboyina 6-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized Metabolites International Journal of Molecular Sciences phytochemicals steroidal saponins hyphenated methods liquid chromatography molecular networking |
| title | 6-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized Metabolites |
| title_full | 6-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized Metabolites |
| title_fullStr | 6-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized Metabolites |
| title_full_unstemmed | 6-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized Metabolites |
| title_short | 6-Oxofurostane and (iso)Spirostane Types of Saponins in <i>Smilax sieboldii</i>: UHPLC-QToF-MS/MS and GNPS-Molecular Networking Approach for the Rapid Dereplication and Biodistribution of Specialized Metabolites |
| title_sort | 6 oxofurostane and iso spirostane types of saponins in i smilax sieboldii i uhplc qtof ms ms and gnps molecular networking approach for the rapid dereplication and biodistribution of specialized metabolites |
| topic | phytochemicals steroidal saponins hyphenated methods liquid chromatography molecular networking |
| url | https://www.mdpi.com/1422-0067/24/14/11487 |
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