title: Bisthiodiketopiperazines and Acorane Sesquiterpenes Produced by the Marine-Derived Fungus Penicillium adametzioides AS-53 on Different Culture Media.
abstract: Chemical investigation of the marine-sponge-derived fungus Penicillium adametzioides AS-53 resulted in the identification of two new bisthiodiketopiperazine derivatives, adametizines A (1) and B (2), from cultivation in a liquid potato-dextrose broth (PDB) culture medium, whereas two new acorane sesquiterpenes, adametacorenols A (3) and B (4), were isolated from a rice solid culture medium. The structures of these compounds were elucidated on the basis of spectroscopic analysis. The absolute configuration of compound 1 was determined by X-ray crystallographic analysis, and that of 3 was determined by modified Mosher's method. Compound 1 exhibited lethality against brine shrimp (Artemia salina) with an LD50 value of 4.8 μM and inhibitory activities against Staphyloccocus aureus, Aeromonas hydrophilia, Vibrio spp. V. harveyi and V. parahaemolyticus, and Gaeumannomyces graminis with minimum inhibitory concentration values of 8, 8, 32, 8, and 16 μg/mL, respectively. Chlorination at C-7 significantly increased the brine shrimp lethality and antimicrobial activity of the bisthiodiketopiperazines.
authors.affiliation: †Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.|‡University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, People's Republic of China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Liu
authors.affiliation: †Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
authors.forename: Xiao-Ming
authors.initials: XM
authors.lastname: Li
authors.affiliation: †Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.|‡University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, People's Republic of China.
authors.forename: Ling-Hong
authors.initials: LH
authors.lastname: Meng
authors.affiliation: §Department of Biochemistry and Molecular Biology, Second Military Medical University, Xiangyin Road 800, Shanghai 200433, People's Republic of China.
authors.forename: Wen-Li
authors.initials: WL
authors.lastname: Jiang
authors.affiliation: †Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
authors.forename: Gang-Ming
authors.initials: GM
authors.lastname: Xu
authors.affiliation: §Department of Biochemistry and Molecular Biology, Second Military Medical University, Xiangyin Road 800, Shanghai 200433, People's Republic of China.
authors.forename: Cai-Guo
authors.initials: CG
authors.lastname: Huang
authors.affiliation: †Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
authors.forename: Bin-Gui
authors.initials: BG
authors.lastname: Wang
mesh_terms: D000333:Aeromonas / Q000187:drug effects; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001156:Artemia / Q000187:drug effects; D018360:Crystallography, X-Ray; D003470:Culture Media; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D011161:Porifera / Q000382:microbiology; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D014733:Vibrio / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D003470:Culture Media; D054659:Diketopiperazines; D012717:Sesquiterpenes; C000601094:adametacorenol A; C000601095:adametacorenol B; C000601092:adametizine A; C000601093:adametizine B