Marinopyrones A–D, α-pyrones from marine-derived actinomycetes of the family Nocardiopsaceae
作者： Jihye Lee , Chulkyeong Han , Tae Gu Lee , Jungwook Chin , Hyukjae Choi
DOI: 10.1016/J.TETLET.2016.03.084
关键词: Stereochemistry 、 Absolute configuration 、 Mouse Macrophage 、 Family Nocardiopsaceae 、 Nocardiopsaceae 、 Chemistry 、 Nocardiopsis sp. 、 Halophile 、 Amide 、 Two-dimensional nuclear magnetic resonance spectroscopy
摘要: Abstract Two actinomycetes, a member of the rare halophilic genus Streptomonospora and Nocardiopsis sp. (Nocardiopsaceae), strains CNQ-082 CNQ-675, respectively, were isolated from marine sediments collected off shore near La Jolla, California. HPLC-UV guided fractionations extracts these yielded marinopyrones A–D ( 1 – 4 ), structures which elucidated by interpretation 1D 2D NMR HRMS spectroscopic data. Oxidative ozonation, followed conversion acid product to an α-naphthyl amide, provided absolute configuration at chiral center on side-chain. Marinopyrones examined for inhibitory activity nitric oxide production in LPS-activated mouse macrophage cells (RAW 264.7); marinopyrone D ) was with IC 50 value 13 μM. To our knowledge, A–C are only second reported natural products .
elsevier.com
sci-hub.se 参考文章(21)
Martina Cappelletti, Alessandro Presentato, Giorgio Milazzo, Raymond J. Turner, Stefano Fedi, Dario Frascari, Davide Zannoni, Growth of Rhodococcus sp. strain BCP1 on gaseous n-alkanes: new metabolic insights and transcriptional analysis of two soluble di-iron monooxygenase genes. Frontiers in Microbiology. ,vol. 6, pp. 1- 15 ,(2015) , 10.3389/FMICB.2015.00393
Abdessamad Debbab, Amal H. Aly, RuAngelie Edrada-Ebel, Victor Wray, Werner E. G. Müller, Frank Totzke, Ute Zirrgiebel, Christoph Schächtele, Michael H. G. Kubbutat, Wen Han Lin, Mahjouba Mosaddak, Abdelhak Hakiki, Peter Proksch, Rainer Ebel, Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium. Journal of Natural Products. ,vol. 72, pp. 626- 631 ,(2009) , 10.1021/NP8004997
M.Soledade C. Pedras, Claudia C. Erosa-López, J.Wilson Quail, Janet L. Taylor, Phomalairdenone: a new host-selective phytotoxin from a virulent type of the blackleg fungus Phoma lingam. Bioorganic & Medicinal Chemistry Letters. ,vol. 9, pp. 3291- 3294 ,(1999) , 10.1016/S0960-894X(99)00602-2
A Prieto-Davó, W Fenical, PR Jensen, Comparative actinomycete diversity in marine sediments Aquatic Microbial Ecology. ,vol. 52, pp. 1- 11 ,(2008) , 10.3354/AME01211
Maria Letizia Ciavatta, Emiliano Manzo, Genoveffa Nuzzo, Guido Villani, Guido Cimino, Juan Lucas Cervera, Manuel Antonio E. Malaquias, Margherita Gavagnin, Aplysiopsenes: an additional example of marine polyketides with a mixed acetate/propionate pathway Tetrahedron Letters. ,vol. 50, pp. 527- 529 ,(2009) , 10.1016/J.TETLET.2008.11.058
János Bérdy, Bioactive microbial metabolites. The Journal of Antibiotics. ,vol. 58, pp. 1- 26 ,(2005) , 10.1038/JA.2005.1
Dao-Feng Zhang, Hua-Qi Pan, Jie He, Xiao-Mei Zhang, Yong-Guang Zhang, Hans-Peter Klenk, Jiang-Chun Hu, Wen-Jun Li, Description of Streptomonospora sediminis sp. nov. and Streptomonospora nanhaiensis sp. nov., and reclassification of Nocardiopsis arabia Hozzein & Goodfellow 2008 as Streptomonospora arabica comb. nov. and emended description of the genus Streptomonospora International Journal of Systematic and Evolutionary Microbiology. ,vol. 63, pp. 4447- 4455 ,(2013) , 10.1099/IJS.0.052704-0
Mikhail Metelev, Jonathan I. Tietz, Joel O. Melby, Patricia M. Blair, Lingyang Zhu, Itamar Livnat, Konstantin Severinov, Douglas A. Mitchell, Structure, bioactivity, and resistance mechanism of streptomonomicin, an unusual lasso peptide from an understudied halophilic actinomycete Chemistry & Biology. ,vol. 22, pp. 241- 250 ,(2015) , 10.1016/J.CHEMBIOL.2014.11.017
Dong-Chan Oh, Erin A. Gontang, Christopher A. Kauffman, Paul R. Jensen, William Fenical, Salinipyrones and pacificanones, mixed-precursor polyketides from the marine actinomycete Salinispora pacifica. Journal of Natural Products. ,vol. 71, pp. 570- 575 ,(2008) , 10.1021/NP0705155
Adele Cutignano, Angelo Fontana, Licia Renzulli, Guido Cimino, Placidenes C-F, novel alpha-pyrone propionates from the Mediterranean sacoglossan Placida dendritica. Journal of Natural Products. ,vol. 66, pp. 1399- 1401 ,(2003) , 10.1021/NP0300176