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Amarisolide monohydrate, a 2-(beta-glucosyl)neoclerodane
R A Toscano1, E Maldonado, A Ortega
1Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Apartado Postal 70-213, México DF 04510, México. toscano@servidor.unam.mx
Summary
The absolute configuration of amarisolide, a neoclerodane glycoside, was determined. Its structure, 2beta-(O-beta-D-glucopyranosyl)neocleroda-3,13(16),14-trien-15,16-epoxy-18,19-olide, was confirmed through its glucose moiety.
Area of Science:
- Natural Product Chemistry
- Organic Chemistry
- Glycoscience
Background:
- Amarisolide is a neoclerodane glycoside with potential biological activity.
- Determining the absolute configuration of complex natural products is crucial for understanding their properties and interactions.
Purpose of the Study:
- To elucidate the absolute configuration and structure of amarisolide.
- To characterize the solid-state structure, including intermolecular interactions.
Main Methods:
- Structure elucidation using spectroscopic methods (e.g., NMR, MS).
- Determination of absolute configuration by association with the known configuration of the glucose moiety.
- X-ray crystallography to confirm the structure and analyze hydrogen bonding.
Main Results:
- The absolute configuration of amarisolide was established as 2beta-(O-beta-D-glucopyranosyl)neocleroda-3,13(16),14-trien-15,16-epoxy-18,19-olide.
- Amarisolide was crystallized as a monohydrate (C26H36O9*H2O).
- Extensive hydrogen bonding networks involving the glucose hydroxyl groups and water molecules were observed, forming layered structures.
Conclusions:
- The complete structure and absolute configuration of amarisolide have been unambiguously determined.
- The study provides insights into the supramolecular assembly of amarisolide monohydrate through hydrogen bonding.