title: Penicillitone, a potent in vitro anti-inflammatory and cytotoxic rearranged sterol with an unusual tetracycle core produced by Penicillium purpurogenum.
abstract: A rearranged sterol with an unusual tetracycle core skeleton, penicillitone (1), and a new sterol, penicillisterol (2), were obtained from the culture of the fungus Penicillium purpurogenum SC0070. Their structures were characterized by spectroscopic analysis, DFT/TDDFT compuations, and X-ray diffraction. Compound 1 demonstrated potent inhibitory effects on tumor cell growth and key pro-inflammatory cytokine production in macrophages. A biogenetic pathway with oxidative cleavage and vinylogous aldol addition as key reactions is proposed for 1.
authors.affiliation: Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
authors.forename: Jinghua
authors.initials: J
authors.lastname: Xue
authors.forename: Ping
authors.initials: P
authors.lastname: Wu
authors.forename: Liangxiong
authors.initials: L
authors.lastname: Xu
authors.forename: Xiaoyi
authors.initials: X
authors.lastname: Wei
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016207:Cytokines / Q000187:drug effects / Q000378:metabolism; D004354:Drug Screening Assays, Antitumor; D056945:Hep G2 Cells; D006801:Humans; D008070:Lipopolysaccharides / Q000494:pharmacology; D061986:MCF-7 Cells; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D013261:Sterols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000187:drug effects; D000093242:Interleukin-6 Inhibitors
chemical_list: D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D016207:Cytokines; D008070:Lipopolysaccharides; D013261:Sterols; D014409:Tumor Necrosis Factor-alpha; D000093242:Interleukin-6 Inhibitors; C000588751:penicillitone