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

• Published in: Journal of natural products (Washington, D.C.) Vol. 80; no. 1; pp. 71 - 75
• Main Authors: Zhu, Meilin, Zhang, Xiaomin, Feng, Huimin, Dai, Jiajia, Li, Jing, Che, Qian, Gu, Qianqun, Zhu, Tianjiao, Li, Dehai
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 27.01.2017; Amer Chemical Soc
• Subjects: Alkaloids - chemistry; Alkaloids - isolation & purification; Chemistry, Medicinal; Citrinin - chemistry; Citrinin - isolation & purification; Crystallography, X-Ray; Life Sciences & Biomedicine; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oxazines - chemistry; Penicillium - chemistry; Pharmacology & Pharmacy; Piperazines - chemistry; Piperazines - isolation & purification; Plant Sciences; Rhizophoraceae - chemistry; Rhizophoraceae - microbiology; Science & Technology; GLIOVIRIN; EPIDITHIODIKETOPIPERAZINES
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.6b00483

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.