Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus <i>Penicillium oxalicum</i>
Ya-Ping Liu,
Sheng-Tao Fang,
Zhen-Zhen Shi,
Bin-Gui Wang,
Xiao-Nian Li,
Nai-Yun Ji
Affiliations
Ya-Ping Liu
Yantai Institute of Coastal Zone Research, Center for Ocean Mega-Science, Chinese Academy of Sciences, Yantai 264003, China
Sheng-Tao Fang
Yantai Institute of Coastal Zone Research, Center for Ocean Mega-Science, Chinese Academy of Sciences, Yantai 264003, China
Zhen-Zhen Shi
Yantai Institute of Coastal Zone Research, Center for Ocean Mega-Science, Chinese Academy of Sciences, Yantai 264003, China
Bin-Gui Wang
Laboratory of Marine Biology and Biotechnology of the Qingdao National Laboratory for Marine Science and Technology, Key Laboratory of Experimental Marine Biology at the Institute of Oceanology, Center for Ocean Mega-Science, Chinese Academy of Sciences, Qingdao 266071, China
Xiao-Nian Li
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
Nai-Yun Ji
Yantai Institute of Coastal Zone Research, Center for Ocean Mega-Science, Chinese Academy of Sciences, Yantai 264003, China
Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.
