New Structures, Spectrometric Quantification, and Inhibitory Properties of Cardenolides from Asclepias curassavica Seeds
Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus Asclepias, cardenolides in milkweed plants have an established role in plant–herbivore and predator–prey interactions, based on their ability to inhibit the membrane-bound Na+/K+-ATPase enzyme. Milkweed seeds...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Jg. 28; H. 1; S. 105 |
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| Abstract | Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus Asclepias, cardenolides in milkweed plants have an established role in plant–herbivore and predator–prey interactions, based on their ability to inhibit the membrane-bound Na+/K+-ATPase enzyme. Milkweed seeds are eaten by specialist lygaeid bugs, which are the most cardenolide-tolerant insects known. These insects likely impose natural selection for the repeated derivatisation of cardenolides. A first step in investigating this hypothesis is to conduct a phytochemical profiling of the cardenolides in the seeds. Here, we report the concentrations of 10 purified cardenolides from the seeds of Asclepias curassavica. We report the structures of new compounds: 3-O-β-allopyranosyl coroglaucigenin (1), 3-[4′-O-β-glucopyranosyl-β-allopyranosyl] coroglaucigenin (2), 3′-O-β-glucopyranosyl-15-β-hydroxycalotropin (3), and 3-O-β-glucopyranosyl-12-β-hydroxyl coroglaucigenin (4), as well as six previously reported cardenolides (5–10). We test the in vitro inhibition of these compounds on the sensitive porcine Na+/K+-ATPase. The least inhibitory compound was also the most abundant in the seeds—4′-O-β-glucopyranosyl frugoside (5). Gofruside (9) was the most inhibitory. We found no direct correlation between the number of glycosides/sugar moieties in a cardenolide and its inhibitory effect. Our results enhance the literature on cardenolide diversity and concentration among tissues eaten by insects and provide an opportunity to uncover potential evolutionary relationships between tissue-specific defense expression and insect adaptations in plant–herbivore interactions. |
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| AbstractList | Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus Asclepias, cardenolides in milkweed plants have an established role in plant–herbivore and predator–prey interactions, based on their ability to inhibit the membrane-bound Na+/K+-ATPase enzyme. Milkweed seeds are eaten by specialist lygaeid bugs, which are the most cardenolide-tolerant insects known. These insects likely impose natural selection for the repeated derivatisation of cardenolides. A first step in investigating this hypothesis is to conduct a phytochemical profiling of the cardenolides in the seeds. Here, we report the concentrations of 10 purified cardenolides from the seeds of Asclepias curassavica. We report the structures of new compounds: 3-O-β-allopyranosyl coroglaucigenin (1), 3-[4′-O-β-glucopyranosyl-β-allopyranosyl] coroglaucigenin (2), 3′-O-β-glucopyranosyl-15-β-hydroxycalotropin (3), and 3-O-β-glucopyranosyl-12-β-hydroxyl coroglaucigenin (4), as well as six previously reported cardenolides (5–10). We test the in vitro inhibition of these compounds on the sensitive porcine Na+/K+-ATPase. The least inhibitory compound was also the most abundant in the seeds—4′-O-β-glucopyranosyl frugoside (5). Gofruside (9) was the most inhibitory. We found no direct correlation between the number of glycosides/sugar moieties in a cardenolide and its inhibitory effect. Our results enhance the literature on cardenolide diversity and concentration among tissues eaten by insects and provide an opportunity to uncover potential evolutionary relationships between tissue-specific defense expression and insect adaptations in plant–herbivore interactions. Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus , cardenolides in milkweed plants have an established role in plant-herbivore and predator-prey interactions, based on their ability to inhibit the membrane-bound Na /K -ATPase enzyme. Milkweed seeds are eaten by specialist lygaeid bugs, which are the most cardenolide-tolerant insects known. These insects likely impose natural selection for the repeated derivatisation of cardenolides. A first step in investigating this hypothesis is to conduct a phytochemical profiling of the cardenolides in the seeds. Here, we report the concentrations of 10 purified cardenolides from the seeds of . We report the structures of new compounds: 3- - -allopyranosyl coroglaucigenin ( ), 3-[4'- - -glucopyranosyl- -allopyranosyl] coroglaucigenin ( ), 3'- - -glucopyranosyl-15- -hydroxycalotropin ( ), and 3- - -glucopyranosyl-12- -hydroxyl coroglaucigenin ( ), as well as six previously reported cardenolides ( - ). We test the in vitro inhibition of these compounds on the sensitive porcine Na /K -ATPase. The least inhibitory compound was also the most abundant in the seeds-4'- - -glucopyranosyl frugoside ( ). Gofruside ( ) was the most inhibitory. We found no direct correlation between the number of glycosides/sugar moieties in a cardenolide and its inhibitory effect. Our results enhance the literature on cardenolide diversity and concentration among tissues eaten by insects and provide an opportunity to uncover potential evolutionary relationships between tissue-specific defense expression and insect adaptations in plant-herbivore interactions. Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus Asclepias, cardenolides in milkweed plants have an established role in plant-herbivore and predator-prey interactions, based on their ability to inhibit the membrane-bound Na+/K+-ATPase enzyme. Milkweed seeds are eaten by specialist lygaeid bugs, which are the most cardenolide-tolerant insects known. These insects likely impose natural selection for the repeated derivatisation of cardenolides. A first step in investigating this hypothesis is to conduct a phytochemical profiling of the cardenolides in the seeds. Here, we report the concentrations of 10 purified cardenolides from the seeds of Asclepias curassavica. We report the structures of new compounds: 3-O-β-allopyranosyl coroglaucigenin (1), 3-[4'-O-β-glucopyranosyl-β-allopyranosyl] coroglaucigenin (2), 3'-O-β-glucopyranosyl-15-β-hydroxycalotropin (3), and 3-O-β-glucopyranosyl-12-β-hydroxyl coroglaucigenin (4), as well as six previously reported cardenolides (5-10). We test the in vitro inhibition of these compounds on the sensitive porcine Na+/K+-ATPase. The least inhibitory compound was also the most abundant in the seeds-4'-O-β-glucopyranosyl frugoside (5). Gofruside (9) was the most inhibitory. We found no direct correlation between the number of glycosides/sugar moieties in a cardenolide and its inhibitory effect. Our results enhance the literature on cardenolide diversity and concentration among tissues eaten by insects and provide an opportunity to uncover potential evolutionary relationships between tissue-specific defense expression and insect adaptations in plant-herbivore interactions.Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus Asclepias, cardenolides in milkweed plants have an established role in plant-herbivore and predator-prey interactions, based on their ability to inhibit the membrane-bound Na+/K+-ATPase enzyme. Milkweed seeds are eaten by specialist lygaeid bugs, which are the most cardenolide-tolerant insects known. These insects likely impose natural selection for the repeated derivatisation of cardenolides. A first step in investigating this hypothesis is to conduct a phytochemical profiling of the cardenolides in the seeds. Here, we report the concentrations of 10 purified cardenolides from the seeds of Asclepias curassavica. We report the structures of new compounds: 3-O-β-allopyranosyl coroglaucigenin (1), 3-[4'-O-β-glucopyranosyl-β-allopyranosyl] coroglaucigenin (2), 3'-O-β-glucopyranosyl-15-β-hydroxycalotropin (3), and 3-O-β-glucopyranosyl-12-β-hydroxyl coroglaucigenin (4), as well as six previously reported cardenolides (5-10). We test the in vitro inhibition of these compounds on the sensitive porcine Na+/K+-ATPase. The least inhibitory compound was also the most abundant in the seeds-4'-O-β-glucopyranosyl frugoside (5). Gofruside (9) was the most inhibitory. We found no direct correlation between the number of glycosides/sugar moieties in a cardenolide and its inhibitory effect. Our results enhance the literature on cardenolide diversity and concentration among tissues eaten by insects and provide an opportunity to uncover potential evolutionary relationships between tissue-specific defense expression and insect adaptations in plant-herbivore interactions. |
| Author | Rubiano-Buitrago, Paola Rowland, Hannah M. Pradhan, Shrikant Paetz, Christian |
| AuthorAffiliation | 1 Research Group Predators and Toxic Prey, Max Planck Institute for Chemical Ecology, Hans Knöll Straße 8, 07745 Jena, Germany 2 Research Group Biosynthesis/NMR, Max Planck Institute for Chemical Ecology, Hans Knöll Straße 8, 07745 Jena, Germany |
| AuthorAffiliation_xml | – name: 2 Research Group Biosynthesis/NMR, Max Planck Institute for Chemical Ecology, Hans Knöll Straße 8, 07745 Jena, Germany – name: 1 Research Group Predators and Toxic Prey, Max Planck Institute for Chemical Ecology, Hans Knöll Straße 8, 07745 Jena, Germany |
| Author_xml | – sequence: 1 givenname: Paola orcidid: 0000-0002-4750-8528 surname: Rubiano-Buitrago fullname: Rubiano-Buitrago, Paola – sequence: 2 givenname: Shrikant orcidid: 0000-0002-5074-3633 surname: Pradhan fullname: Pradhan, Shrikant – sequence: 3 givenname: Christian orcidid: 0000-0002-5776-7574 surname: Paetz fullname: Paetz, Christian – sequence: 4 givenname: Hannah M. orcidid: 0000-0002-1040-555X surname: Rowland fullname: Rowland, Hannah M. |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36615300$$D View this record in MEDLINE/PubMed |
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| Keywords | Apocynaceae toxicity Na+/K+ ATPase activity secondary metabolites phytochemistry |
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| Snippet | Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus Asclepias, cardenolides in milkweed plants have an established role... Cardiac glycosides are a large class of secondary metabolites found in plants. In the genus , cardenolides in milkweed plants have an established role in... |
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| SubjectTerms | Animals Apocynaceae Asclepias - chemistry Cardenolides - chemistry Cardenolides - pharmacology Cardiac Glycosides - pharmacology Glucose Herbivores Leaves Metabolites Na+/K+ ATPase activity Natural products phytochemistry Plants - metabolism secondary metabolites Seeds Seeds - metabolism Sodium-Potassium-Exchanging ATPase - metabolism Spectrum analysis Swine toxicity |
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