Abstract
Nine new conjugates of sesquiterpenoids and acylphloroglucinols, named eucarobustols A-I (1-9), as well as 11 known analogues were isolated from the leaves of Eucalyptus robusta. The sesquiterpenoid motifs furnishing the new conjugates included four structural types of aristolane (1 and 2), guaiane (3), eudesmane (4), and aromadendrane (5-9) moieties. Compounds 1 and 2 were found to represent the first examples of conjugates of aristolane and acylphloroglucinol units. In turn, compound 3 features a new coupling model of guaiane and acylphloroglucinol via the C-4-C-7' bond. Compounds 1, 7, and 9 showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 1.3, 1.8, and 1.6 μM, respectively.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Drugs, Chinese Herbal / chemistry
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Drugs, Chinese Herbal / isolation & purification*
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Drugs, Chinese Herbal / pharmacology
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Eucalyptus / chemistry*
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Inhibitory Concentration 50
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Plant Leaves / chemistry
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Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
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Sesquiterpenes
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Sesquiterpenes, Eudesmane / chemistry
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Sesquiterpenes, Eudesmane / isolation & purification*
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Sesquiterpenes, Eudesmane / pharmacology
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Sesquiterpenes, Guaiane / chemistry
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Sesquiterpenes, Guaiane / isolation & purification*
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Sesquiterpenes, Guaiane / pharmacology
Substances
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Drugs, Chinese Herbal
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Sesquiterpenes
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Sesquiterpenes, Eudesmane
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Sesquiterpenes, Guaiane
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aromadendrane
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guaiane
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eudesmane
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Protein Tyrosine Phosphatase, Non-Receptor Type 1