title: Chrysamides A-C, Three Dimeric Nitrophenyl trans-Epoxyamides Produced by the Deep-Sea-Derived Fungus Penicillium chrysogenum SCSIO41001.
abstract: 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.
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.|Department of Chemistry, Jinan University , Guangzhou 510632, China.
authors.forename: Shengtian
authors.initials: S
authors.lastname: Chen
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Junfeng
authors.initials: J
authors.lastname: Wang
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Xiuping
authors.initials: X
authors.lastname: Lin
authors.affiliation: Department of Chemistry, Jinan University , Guangzhou 510632, China.
authors.forename: Bingxin
authors.initials: B
authors.lastname: Zhao
authors.affiliation: Key Laboratory of Plant Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences , Guangzhou 510650, China.
authors.forename: Xiaoyi
authors.initials: X
authors.lastname: Wei
authors.affiliation: Department of Chemistry, Jinan University , Guangzhou 510632, China.
authors.forename: Guangqiang
authors.initials: G
authors.lastname: Li
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Kumaravel
authors.initials: K
authors.lastname: Kaliaperumal
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Shengrong
authors.initials: S
authors.lastname: Liao
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Bin
authors.initials: B
authors.lastname: Yang
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Zhou
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Juan
authors.initials: J
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Jinan University , Guangzhou 510632, China.
authors.forename: Shihai
authors.initials: S
authors.lastname: Xu
authors.affiliation: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
authors.forename: Yonghong
authors.initials: Y
authors.lastname: Liu
mesh_terms: D000577:Amides / Q000737:chemistry / Q000378:metabolism*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000378:metabolism*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D010408:Penicillium chrysogenum / Q000737:chemistry* / Q000378:metabolism; D010879:Piperazines / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D001643:Bridged Bicyclo Compounds; D010879:Piperazines; C000627554:chrysamide A; C000627555:chrysamide B; C000627553:chrysamide C