Chrysamides A–C, Three Dimeric Nitrophenyl trans-Epoxyamides Produced by the Deep-Sea-Derived Fungus Penicillium chrysogenum SCSIO41001

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• 作者：Shengtian Chen ; Junfeng Wang ; Xiuping Lin ; Bingxin Zhao ; Xiaoyi Wei ; Guangqiang Li ; Kumaravel Kaliaperumal ; Shengrong Liao ; Bin Yang ; Xuefeng Zhou ; Juan Liu ; Shihai Xu ; Yonghong Liu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：18
• 期：15
• 页码：3650-3653
• 全文大小：285K
• 年卷期：0
• ISSN：1523-7052

文摘

Three dimeric nitrophenyl trans-epoxyamides, chrysamides A–C (1–3), were obtained from the deep-sea-derived fungus Penicillium chrysogenum SCSIO41001. Their structures were characterized by spectroscopic analysis, electronic circular dichroism computations, and X-ray single-crystal diffraction analysis. Notably, compound 1 possesses a novel centrosymmetric dimer skeleton featuring an unprecedented 7-oxa-2,5-diazabicyclo[2.2.1]heptane ring system, which represents the first example of dimeric nitrophenyl trans-epoxyamide in nature. Compound 3 suppresses the production of proinflammatory cytokine interleukin-17. A possible biosynthetic pathway of 1–3 was proposed.