Abstract
Scospirosins A (1) and B (2), two unprecedented spiro ent-clerodane dimers with 6/6/10/6 and 6/6/6/6/6 ring systems, respectively, were isolated from Isodon scoparius. Their structures were unambiguously established by spectroscopic, X-ray crystallographic, and chemical approaches. A bioinspired protecting-group-free strategy for their synthesis was achieved on a gram scale and featured the application of green methods, including neat reaction, sensitized photooxygenation, and electrochemical oxidation. 2 exhibited selective immunosuppressive activity against the proliferation of T lymphocytes (IC50 = 1.42 μM).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification
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Antineoplastic Agents, Phytogenic / pharmacology*
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Biomimetics
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Cell Proliferation / drug effects
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Crystallography, X-Ray
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Diterpenes, Clerodane / analysis
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Diterpenes, Clerodane / chemical synthesis*
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Diterpenes, Clerodane / pharmacology*
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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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Inhibitory Concentration 50
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Isodon / chemistry*
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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T-Lymphocytes / drug effects
Substances
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Antineoplastic Agents, Phytogenic
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Diterpenes, Clerodane
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Immunosuppressive Agents