Aspergillines A–E, Highly Oxygenated Hexacyclic Indole–Tetrahydrofuran–Tetramic Acid Derivatives from Aspergillus versicolor

Aspergillines A–E (1–5) are highly oxygenated cyclopiazonic acid (CPA)-derived alkaloids bearing a rigid and sterically congested hexacyclic indole–tetrahydrofuran–tetramate scaffold, isolated from the endophytic fungus Aspergillus vesicolor. Apergillines A–C represent a new subclass of CPA-derived...

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Bibliographic Details
Published in:Organic letters 2014-10, Vol.16 (19), p.5016-5019
Main Authors: Zhou, Min, Miao, Ming-Ming, Du, Gang, Li, Xiao-Nian, Shang, Shan-Zhai, Zhao, Wei, Liu, Zhi-Hua, Yang, Guang-Yu, Che, Chun-Tao, Hu, Qiu-Fen, Gao, Xue-Mei
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Aspergillus - chemistry
Circular Dichroism
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Heterocyclic Compounds, 4 or More Rings - chemistry
Heterocyclic Compounds, 4 or More Rings - isolation & purification
Heterocyclic Compounds, 4 or More Rings - pharmacology
Indoles - chemistry
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pyrrolidinones - chemistry
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Summary:Aspergillines A–E (1–5) are highly oxygenated cyclopiazonic acid (CPA)-derived alkaloids bearing a rigid and sterically congested hexacyclic indole–tetrahydrofuran–tetramate scaffold, isolated from the endophytic fungus Aspergillus vesicolor. Apergillines A–C represent a new subclass of CPA-derived alkaloids, and aspergillines B and E possess a butanoic acid methyl ester moiety. The structures, including absolute configuration, were elucidated by interpretation of the NMR, X-ray crystallographic, and circular dichroism data. All compounds displayed anti-TMV and cytotoxic activities.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502307u