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Penicillitone, a Potent in Vitro Anti-inflammatory and Cytotoxic Rearranged Sterol with an Unusual Tetracycle Core Produced by Penicillium purpurogenum

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posted on 07.03.2014, 00:00 by Jinghua Xue, Ping Wu, Liangxiong Xu, Xiaoyi Wei
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.