Abstract
Ivorenolide A (1), a novel 18-membered macrolide featuring conjugated acetylenic bonds and five chiral centers, was isolated from Khaya ivorensis. The structure of 1 was fully determined by spectroscopic analysis, single-crystal X-ray diffraction, and bioinspired total synthesis. Both compound 1 and its synthetic enantiomer 2 showed potent and selective immunosuppressive activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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B-Lymphocytes / drug effects
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B-Lymphocytes / immunology
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Crystallography, X-Ray
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Immunosuppressive Agents / chemistry*
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Immunosuppressive Agents / isolation & purification
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Immunosuppressive Agents / pharmacology
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Macrolides / chemistry*
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Macrolides / isolation & purification
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Macrolides / pharmacology
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Meliaceae / chemistry*
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Mice
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Models, Molecular
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Stereoisomerism
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T-Lymphocytes / drug effects
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T-Lymphocytes / immunology
Substances
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Immunosuppressive Agents
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Macrolides
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ivorenolide A