title: Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum.
abstract: Six new pyridone alkaloids, named penipyridones A-F (1-6), were isolated from the fermentation broth of an Antarctic moss-derived fungus, Penicillium funiculosum GWT2-24. Their structures were elucidated from extensive NMR and MS data. Although they possess the same major chromophore and some of them presented almost mirror ECD spectra, their absolute configurations were found to be uniformly S, as evidenced by X-ray single-crystal diffraction analysis, stereocontrolled total synthesis, and chemical conversions. TDDFT-ECD calculations of compounds 3 and 6 revealed that subtle conformational changes are responsible for the significantly different ECD curves. None of the compounds were cytotoxic (IC50 > 50 μM), while compounds 1, 2, 5, and 7 elicited lipid-lowering activity in HepG2 hepatocytes.
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
authors.forename: Haibo
authors.initials: H
authors.lastname: Zhou
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
authors.forename: Liyuan
authors.initials: L
authors.lastname: Li
authors.affiliation: Pharmacology and Toxicology Research Center, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College , Beijing 100193, People's Republic of China.
authors.forename: Chongming
authors.initials: C
authors.lastname: Wu
authors.affiliation: Department of Organic Chemistry, University of Debrecen , POB 20, 4010 Debrecen, Hungary.
authors.forename: Tibor
authors.initials: T
authors.lastname: Kurtán
authors.affiliation: Department of Organic Chemistry, University of Debrecen , POB 20, 4010 Debrecen, Hungary.
authors.forename: Attila
authors.initials: A
authors.lastname: Mándi
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
authors.forename: Yankai
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
authors.forename: Qianqun
authors.initials: Q
authors.lastname: Gu
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
authors.forename: Tianjiao
authors.initials: T
authors.lastname: Zhu
authors.affiliation: Pharmacology and Toxicology Research Center, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College , Beijing 100193, People's Republic of China.
authors.forename: Peng
authors.initials: P
authors.lastname: Guo
authors.affiliation: Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
authors.forename: Dehai
authors.initials: D
authors.lastname: Li
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000864:Antarctic Regions; D018360:Crystallography, X-Ray; D056945:Hep G2 Cells; D006801:Humans; D000960:Hypolipidemic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D011728:Pyridones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000470:Alkaloids; D000960:Hypolipidemic Agents; D011728:Pyridones; C000618476:penipyridone A