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[The structure of sulfated cauloside C]
1Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, Vladivostok, Russia. piboc@stl.ru
Bioorganicheskaia Khimiia
|July 20, 2000
Summary
The structure of a sulfated cauloside C analogue was identified. This biologically active triterpenoid glycoside was confirmed using carbon-13 nuclear magnetic resonance spectroscopy.
Area of Science:
- Natural Product Chemistry
- Glycoscience
- Spectroscopy
Context:
- Cauloside C is a known biologically active triterpenoid glycoside.
- Sulfated analogues of natural products often exhibit modified bioactivity.
- Structural elucidation is crucial for understanding compound function.
Purpose:
- To determine the precise chemical structure of a sulfated analogue of cauloside C.
- To confirm the sulfation pattern and glycosidic linkage of the novel compound.
- To differentiate the analogue from the parent cauloside C molecule.
Summary:
- The structure of the sulfated cauloside C analogue was elucidated as 3-O-[beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-hederagenin 23,4",4",6"-tetrasulfate pentasodium salt.
- This determination was achieved by comparing the 13C NMR spectrum of the analogue with that of cauloside C potassium salt.
- The study confirms the presence of four sulfate groups and a specific pentasodium salt form.
Impact:
- Provides a detailed structural characterization of a novel sulfated triterpenoid glycoside.
- Establishes a reference compound for future pharmacological and biochemical studies.
- Contributes to the understanding of structure-activity relationships in glycosylated triterpenoids.