Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reesei
Saponins are a large class of plant natural products that exhibit a great variety of biological and pharmacological properties. Starting from diosgenin and solasodine nine derivatives were synthesized. Via Koenigs-Knorr synthesis glucose was attached to diosgenin and solasodine, respectively. Furthe...
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Elsevier
2025-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624006908 |
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| author | Christina Rodler Johann Schinnerl Miriam Schalamun Wolfgang Hinterdobler Lothar Brecker |
| author_facet | Christina Rodler Johann Schinnerl Miriam Schalamun Wolfgang Hinterdobler Lothar Brecker |
| author_sort | Christina Rodler |
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| description | Saponins are a large class of plant natural products that exhibit a great variety of biological and pharmacological properties. Starting from diosgenin and solasodine nine derivatives were synthesized. Via Koenigs-Knorr synthesis glucose was attached to diosgenin and solasodine, respectively. Furthermore, glucose, cellobiose and glucuronic acid methyl ester were used as trichloroacetimidates in glycosylation reactions with diosgenin. Additionally, via reductive ring-opening reaction the F-ring of diosgenin as well as solasodine was modified, resulting in two compounds, 26-amino-(22R,25R/25S)-furost-5-en-3β-ol. The same reaction was applied to (22R,25R)-spirost-5-en-3β-yl α-d-3′,4′,6′-tri-O-acetyl-glucopyranoside and (22R,25R)-spirost-5-en-3β-yl β-d-2′,3′,6′-tri-O-acetyl-glucopyranosyl-(1 → 4)-β-d-8′,9′,10′,12′-tetra-O-acetyl-glucopyranoside, leading to new compounds. Biological activities of selected compounds as well as isoflavone glycosides were tested on Panagrellus redivivus L., Spodoptera littoralis Boisduval and Trichoderma reesei QM6a. We show that the bioactivity is highly variable, depending not only on the tested organisms, but also on the glycosylation pattern. Especially 26-amino-(22R,25R)-furost-5-en-3β-ol exhibited high nematocidal (75 % mortality rate), anti-herbivorous (feeding rate reduced to 0.4 % leaf area/min) as well as anti-fungal properties (47 % increased anti-fungal activity compared to solasodine) whilst the other tested compounds exhibited only moderate activities. |
| format | Article |
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| institution | Kabale University |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
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| series | Results in Chemistry |
| spelling | doaj-art-0b9c2bc7f17845d99d3503d4e7671fa22025-01-29T05:00:50ZengElsevierResults in Chemistry2211-71562025-01-0113101994Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reeseiChristina Rodler0Johann Schinnerl1Miriam Schalamun2Wolfgang Hinterdobler3Lothar Brecker4University of Vienna, Faculty of Chemistry, Department of Organic Chemistry, Währinger Strasse 38, 1090 Vienna, Austria; University of Vienna, Vienna Doctoral School in Chemistry (DoSChem), Währinger Strasse 42, 1090 Vienna, AustriaUniversity of Vienna, Faculty of Life Sciences, Department of Botany and Biodiversity Research, Rennweg 14, 1030 Vienna, AustriaMyPilz GmbH, Wienerbergstrasse 55/13-15, 1120 Vienna, AustriaMyPilz GmbH, Wienerbergstrasse 55/13-15, 1120 Vienna, AustriaUniversity of Vienna, Faculty of Chemistry, Department of Organic Chemistry, Währinger Strasse 38, 1090 Vienna, Austria; Corresponding author.Saponins are a large class of plant natural products that exhibit a great variety of biological and pharmacological properties. Starting from diosgenin and solasodine nine derivatives were synthesized. Via Koenigs-Knorr synthesis glucose was attached to diosgenin and solasodine, respectively. Furthermore, glucose, cellobiose and glucuronic acid methyl ester were used as trichloroacetimidates in glycosylation reactions with diosgenin. Additionally, via reductive ring-opening reaction the F-ring of diosgenin as well as solasodine was modified, resulting in two compounds, 26-amino-(22R,25R/25S)-furost-5-en-3β-ol. The same reaction was applied to (22R,25R)-spirost-5-en-3β-yl α-d-3′,4′,6′-tri-O-acetyl-glucopyranoside and (22R,25R)-spirost-5-en-3β-yl β-d-2′,3′,6′-tri-O-acetyl-glucopyranosyl-(1 → 4)-β-d-8′,9′,10′,12′-tetra-O-acetyl-glucopyranoside, leading to new compounds. Biological activities of selected compounds as well as isoflavone glycosides were tested on Panagrellus redivivus L., Spodoptera littoralis Boisduval and Trichoderma reesei QM6a. We show that the bioactivity is highly variable, depending not only on the tested organisms, but also on the glycosylation pattern. Especially 26-amino-(22R,25R)-furost-5-en-3β-ol exhibited high nematocidal (75 % mortality rate), anti-herbivorous (feeding rate reduced to 0.4 % leaf area/min) as well as anti-fungal properties (47 % increased anti-fungal activity compared to solasodine) whilst the other tested compounds exhibited only moderate activities.http://www.sciencedirect.com/science/article/pii/S2211715624006908SaponinsGlycosylationReductive ring-openingNematocidal activityAnti-feedant activityAntifungal activity |
| spellingShingle | Christina Rodler Johann Schinnerl Miriam Schalamun Wolfgang Hinterdobler Lothar Brecker Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reesei Results in Chemistry Saponins Glycosylation Reductive ring-opening Nematocidal activity Anti-feedant activity Antifungal activity |
| title | Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reesei |
| title_full | Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reesei |
| title_fullStr | Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reesei |
| title_full_unstemmed | Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reesei |
| title_short | Diosgenin and solasodine-based saponins and sapogenines—Effects of structural modifications on Panagrellus redivivus, Spodoptera littoralis and Trichoderma reesei |
| title_sort | diosgenin and solasodine based saponins and sapogenines effects of structural modifications on panagrellus redivivus spodoptera littoralis and trichoderma reesei |
| topic | Saponins Glycosylation Reductive ring-opening Nematocidal activity Anti-feedant activity Antifungal activity |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624006908 |
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