Clerodane and labdane diterpenoids from Nuxia sphaerocephala
| Autor: | Philippe Rasoanaivo, Lengo Mambu, François Frappier, David Ramanitrahasimbola, Roger Joyeau, Loic Florent, Philippe Grellier |
|---|---|
| Přispěvatelé: | Laboratoire de chimie et biochimie des substances naturelles, Centre National de la Recherche Scientifique (CNRS)-Muséum national d'Histoire naturelle (MNHN), Molécules de Communication et Adaptation des Micro-Organismes (MCAM), Muséum national d'Histoire naturelle (MNHN)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2005 |
| Předmět: |
MESH: Diterpenes
Stereochemistry PGME amide method MESH: Molecular Structure Plasmodium falciparum Ethyl acetate MESH: Plant Extracts Plant Science Horticulture Labdanes MESH: Parasitic Sensitivity Tests Biochemistry Diterpenes Clerodane Labdane chemistry.chemical_compound Antimalarials Parasitic Sensitivity Tests Nuxia sphaerocephala Amide MESH: Diterpenes Clerodane Animals MESH: Animals [SDV.BBM]Life Sciences [q-bio]/Biochemistry Molecular Biology Molecular Biology MESH: Plasmodium falciparum biology Molecular Structure Plant Extracts Absolute configuration Clerodanes General Medicine Loganiaceae biology.organism_classification MESH: Antimalarials Terpenoid Nuxia chemistry Antiplasmodial activity Diterpene Diterpenes |
| Zdroj: | Phytochemistry Phytochemistry, Elsevier, 2006, 67 (5), pp.444-51. ⟨10.1016/j.phytochem.2005.11.024⟩ |
| ISSN: | 0031-9422 |
| DOI: | 10.1016/j.phytochem.2005.11.024⟩ |
| Popis: | International audience; Seven diterpenoids including four clerodane and three labdane derivatives, (13S)-ent-7beta-hydroxy-3-cleroden-15-oic acid (1), ent-7beta-hydroxy-2-oxo-3-cleroden-15-oic acid (2), ent-2,7-dioxo-3-clero-den-15-oic acid (3), ent-18-(E)-caffeoyloxy-7beta-hydroxy-3-cleroden-15-oic acid (4) (13S)-ent-18-(E)-coumaroyloxy-8(17)-labden-15-oic acid (5), ent-18-(E)-caffeoyloxy-8(17)-labden-15-oic acid (6), ent-15-(E)-caffeoyloxy-8(17)-labden-18-oic acid (7), have been isolated from an ethyl acetate extract of the leaves of Nuxia sphaerocephala, together with 17 known compounds. 3-Oxolup-20(29)-en-30-al (3-oxolupenal) (8) and 3beta-hydroxylup-20(29)-en-30-al (3beta-hydroxy-lupenal) (9) showed the best inhibitory activity against Plasmodium falciparum with the IC(50) values between 1.55 and 4.67 microg/ml in vitro, respectively. The structure and the relative stereochemistry of the compounds were established on the basis of their spectroscopic properties. The absolute configuration at C-13 of 1 and 5 was determined by the PGME amide procedure. |
| Databáze: | OpenAIRE |
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