title: Penicitroamide, an Antimicrobial Metabolite with High Carbonylization from the Endophytic Fungus Penicillium sp. (NO. 24).
abstract: Penicitroamide (1), a new metabolite with a new framework, was isolated from the ethyl acetate extract of the PDB (Potato Dextrose Broth) medium ofPenicilliumsp. (NO. 24). The endophytic fungusPenicilliumsp. (NO. 24) was obtained from the healthy leaves ofTapiscia sinensisOliv. The structure of penicitroamide (1) features a bicyclo[3.2.1]octane core unit with a high degree of carbonylization (four carbonyl groups and one enol group). The chemical structure of penicitroamide (1) was elucidated by analysis of 1D-, 2D-NMR and MS data. In bioassays, penicitroamide (1) displayed antibacterial potency against two plant pathogens,Erwinia carotovorasubsp. Carotovora (Jones) Bersey, et al. andSclerotium rolfsiiSacc. with MIC50at 45 and 50 μg/mL. Compound1also showed 60% lethality against brine shrimp at 10 μg/mL. Penicitroamide (1) exhibited no significant activity against A549, Caski, HepG2 and MCF-7 cells with IC50> 50 μg/mL. Finally, the possible biosynthetic pathway of penicitroamide (1) was discussed.
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. fzw080907@gmail.com.
authors: Zi-Wei
authors: ZW
authors: Feng
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. MengmengLv828@yeah.net.
authors: Meng-Meng
authors: MM
authors: Lv
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. lixueshuang1205@163.com.
authors: Xue-Shuang
authors: XS
authors: Li
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. zhangliang@hec.cn.
authors: Liang
authors: L
authors: Zhang
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. liuchengxiong666@126.com.
authors: Cheng-Xiong
authors: CX
authors: Liu
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. zhiyongguoctgu@hotmail.com.
authors: Zhi-Yong
authors: ZY
authors: Guo
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. d.zhangshuang@gmail.com.
authors: Zhang-Shuang
authors: ZS
authors: Deng
authors: Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China. kzou@ctgu.edu.cn.
authors: Kun
authors: K
authors: Zou
authors: Institut für Pharmazeutische Biologie und Biotechnologie, Heirich-Heine University Dusseldorf, Universitätsstr. 1, Gebäude 26.23, Dusseldorf 40225, Germany. Peter.Proksch@uni-duesseldorf.de.
authors: Peter
authors: P
authors: Proksch
mesh_terms: D000363:Agaricales / Q000187:drug effects; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000633:toxicity; D001156:Artemia / Q000187:drug effects; D002244:Carbon / Q000737:chemistry; D004885:Erwinia / Q000187:drug effects; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology* / Q000633:toxicity; D006801:Humans; D061986:MCF-7 Cells; D019684:Magnoliopsida / Q000382:microbiology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D018515:Plant Leaves / Q000382:microbiology; D018675:Toxicity Tests
chemical_list: D000890:Anti-Infective Agents; D006575:Heterocyclic Compounds, 3-Ring; D002244:Carbon
keywords: Penicillium sp.; antibacterial activity; brine shrimp lethality; endophytic fungus; penicitroamide