Resin Glycosides from the Roots of Operculina macrocarpa (Brazilian Jalap) with Purgative Activity
| Autor: | Rogelio Pereda-Miranda, Suzana G. Leitão, Jesús Lira-Ricárdez, Jhon Castañeda-Gómez, Mabel Fragoso-Serrano, Rosineide Costa Simas |
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| Rok vydání: | 2019 |
| Předmět: |
Pharmacology
chemistry.chemical_classification Molecular Structure Stereochemistry Chemistry Organic Chemistry Pharmaceutical Science Glycoside Glycosidic bond High-performance liquid chromatography Plant Roots Analytical Chemistry Operculina macrocarpa Operculinic acid Complementary and alternative medicine Acetylation Drug Discovery Molecular Medicine Glycosides Nuclear Magnetic Resonance Biomolecular Saponification Brazil Chromatography High Pressure Liquid Resins Plant |
| Zdroj: | Journal of natural products. 82(6) |
| ISSN: | 1520-6025 |
| Popis: | Analysis of the methanol-soluble resin glycosides from the roots of Operculina macrocarpa was assessed by generating NMR profiles of five glycosidic acids obtained through saponification, acetylation, and recycling HPLC purification. Operculinic acid H (1), two novel hexasaccharides, operculinic acids I (2) and J (3), the known purgic acid A (4), and a quinovopyranoside of (-)-(7 R)-hydroxydecanoic acid, operculinic acid K (5), were isolated. Three intact resin glycosides related to 1, the novel macrocarposidic acids A (6) and B (7), in addition to the previously known macrocarposidic acid C (8), were also purified with isovaleroyl, tigloyl, and exogonoyl [(3 S,9 R)-3,6:6,9-diepoxydecanoyl] groups as esterifying residues. A selective intramolecular lactonization was produced to generate a macrocyclic artifact (17) during acetylation of 1, resembling the distinctive structure of the Convolvulaceous resin glycosides. |
| Databáze: | OpenAIRE |
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