Three new rare cyclopiane diterpenes(1-3),together with thirteen known compounds(4-16),were isolated and identified from a sea sediment-derived fungus Penicillium sp.TJ403-2.The planar and relative structures of compo...Three new rare cyclopiane diterpenes(1-3),together with thirteen known compounds(4-16),were isolated and identified from a sea sediment-derived fungus Penicillium sp.TJ403-2.The planar and relative structures of compounds 1-3 were elucidated by HRESIMS,one-and two-dimensional NMR analyses,and their absolute configurations were further established by X-ray crystallography experiment.Compounds 1-3 were evaluated for the anti-inflammatory activity against LPS-induced NO production,and compound 1 showed notable inhibitory potency with an IC50 value of2.19±0.25μmol/L,which was three fold lower than the positive control indomethacin(IC50=8.76±0.92μmol/L).Further Western blot and immunofluorescence experiments demonstrated its mechanism of action to be that 1 inhibited the NF-κB-activated pathway,highlighting it as a promising starting point for the development of new anti-inflammatory agents.展开更多
Three novel,highly oxygenated polyketides,multioketides A-C(1-3),and three previously described multioxidized aromatic polyketides(4-6),were isolated from an endophytic Penicillium sp.YUD17006 associated with Gastrodi...Three novel,highly oxygenated polyketides,multioketides A-C(1-3),and three previously described multioxidized aromatic polyketides(4-6),were isolated from an endophytic Penicillium sp.YUD17006 associated with Gastrodia elata.Their chem-ical structures were elucidated using extensive spectroscopic data,electronic circular dichroism calculations,and single X-ray diffrac-tion analysis.All metabolites were characterized by a typical α,β-unsaturated ketone fragment and exhibited a high degree of oxidation.Multioketides A and B were identified as a pair of epimers featuring a rare dihydroisobenzofuranone core.Multioketide C possessed a novel 5/6/6/6 heterotetracyclic chemical architecture with unusual 1,4-dioxin functionalities.Plausible biosynthetic pathways for 1-6 were proposed.Additionally,compound 3 demonstrated weak inhibitory activities against both acetylcholinesterase and protein tyr-osine phosphatase 1B.展开更多
基金financially supported by the Program for Changjiang Scholars of Ministry of Education of the People’s Republic of China (No.T2016088)the National Natural Science Foundation for Distinguished Young Scholars (No.81725021)+1 种基金the Innovative Research Groups of the National Natural Science Foundation of China (No.81721005)the National Natural Science Foundation of China (Nos.81573316 and 21702067)
文摘Three new rare cyclopiane diterpenes(1-3),together with thirteen known compounds(4-16),were isolated and identified from a sea sediment-derived fungus Penicillium sp.TJ403-2.The planar and relative structures of compounds 1-3 were elucidated by HRESIMS,one-and two-dimensional NMR analyses,and their absolute configurations were further established by X-ray crystallography experiment.Compounds 1-3 were evaluated for the anti-inflammatory activity against LPS-induced NO production,and compound 1 showed notable inhibitory potency with an IC50 value of2.19±0.25μmol/L,which was three fold lower than the positive control indomethacin(IC50=8.76±0.92μmol/L).Further Western blot and immunofluorescence experiments demonstrated its mechanism of action to be that 1 inhibited the NF-κB-activated pathway,highlighting it as a promising starting point for the development of new anti-inflammatory agents.
基金supported by the Natural Science Foundation of China(No.22267001)the Program for Innovative Research Team of Yunnan Province(No.202105AE160006)+5 种基金the Science and Technology Project of Yunnan Province(Nos.202201AT070225,202301AU070217)Yunnan University“Double First-Class”Construction Joint Project(No.202201BF070001-014)Basic Research Plan of Yunnan Provincial Science and Technology Department-Kunming Medical University(No.202301AY070001-186)Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform(No.2022YKZY001)Key Laboratory of Chemistry in Ethnic Medicinal Resources,State Ethnic Affairs Commission&Ministry of Education,Yunnan Minzu University(No.MZY2205)he Program Innovative Research Team in Science and Technology in Kunming Medical University(No.CXTD202202)。
文摘Three novel,highly oxygenated polyketides,multioketides A-C(1-3),and three previously described multioxidized aromatic polyketides(4-6),were isolated from an endophytic Penicillium sp.YUD17006 associated with Gastrodia elata.Their chem-ical structures were elucidated using extensive spectroscopic data,electronic circular dichroism calculations,and single X-ray diffrac-tion analysis.All metabolites were characterized by a typical α,β-unsaturated ketone fragment and exhibited a high degree of oxidation.Multioketides A and B were identified as a pair of epimers featuring a rare dihydroisobenzofuranone core.Multioketide C possessed a novel 5/6/6/6 heterotetracyclic chemical architecture with unusual 1,4-dioxin functionalities.Plausible biosynthetic pathways for 1-6 were proposed.Additionally,compound 3 demonstrated weak inhibitory activities against both acetylcholinesterase and protein tyr-osine phosphatase 1B.
