Penicisulfuranols A–F, Alkaloids from the Mangrove Endophytic Fungus Penicillium janthinellum HDN13-309

Six new epipolythiodioxopiperazine (ETP) alkaloids, penicisulfuranols A–F (1–6), were isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculation...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2017-01, Vol.80 (1), p.71-75
Main Authors: Zhu, Meilin, Zhang, Xiaomin, Feng, Huimin, Dai, Jiajia, Li, Jing, Che, Qian, Gu, Qianqun, Zhu, Tianjiao, Li, Dehai
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Citrinin - chemistry
Citrinin - isolation & purification
Crystallography, X-Ray
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Oxazines - chemistry
Penicillium - chemistry
Piperazines - chemistry
Piperazines - isolation & purification
Rhizophoraceae - chemistry
Rhizophoraceae - microbiology
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Summary:Six new epipolythiodioxopiperazine (ETP) alkaloids, penicisulfuranols A–F (1–6), were isolated from the mangrove endophytic fungus Penicillium janthinellum HDN13-309. All structures including absolute configurations were elucidated on the basis of comprehensive spectroscopic data and ECD calculations. They belong to the unusual family of ETPs containing sulfur atoms on both α- and β-positions of amino acid residues and a rare 1,2-oxazadecaline core moiety. In addition, compounds 1–6 also possess a rare spiro-furan ring and 1–3 showed cytotoxicity with IC50 values ranging from 0.1 to 3.9 μM.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00483