Pericoannosin A, a Polyketide Synthase–Nonribosomal Peptide Synthetase Hybrid Metabolite with New Carbon Skeleton from the Endophytic Fungus Periconia sp

Four new polyketide synthase–nonribosomal peptide synthetase (PKS–NRPS) hybrid metabolites, pericoannosin A (1), with an unusual hexahydro-1H-isochromen-5-isobutylpyrrolidin-2-one skeleton, and three cytochalasans, periconiasins D–F (2–4), were isolated from the endophytic fungus Periconia sp. F-31....

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Bibliographic Details
Published in:Organic letters 2015-09, Vol.17 (17), p.4304-4307
Main Authors: Zhang, Dewu, Tao, Xiaoyu, Chen, Ridao, Liu, Jimei, Li, Li, Fang, Xiaomei, Yu, Liyan, Dai, Jungui
Format: Article
Language:English
Subjects:
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
Ascomycota - chemistry
Carbon
Crystallography, X-Ray
Cytochalasins - chemistry
Cytochalasins - isolation & purification
Inhibitory Concentration 50
Isocoumarins
Molecular Conformation
Molecular Structure
Polyketide Synthases - metabolism
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Summary:Four new polyketide synthase–nonribosomal peptide synthetase (PKS–NRPS) hybrid metabolites, pericoannosin A (1), with an unusual hexahydro-1H-isochromen-5-isobutylpyrrolidin-2-one skeleton, and three cytochalasans, periconiasins D–F (2–4), were isolated from the endophytic fungus Periconia sp. F-31. Their structures and absolute configurations were elucidated through extensive spectroscopic analyses, calculated ECD, and single-crystal X-ray diffraction (Cu Kα). A possible biogenetic pathway is proposed. Compounds 1 and 4 showed anti-HIV activity with IC50s of 69.6 and 29.2 μM, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02123