title: Chermesins A-D: Meroterpenoids with a Drimane-Type Spirosesquiterpene Skeleton from the Marine Algal-Derived Endophytic Fungus Penicillium chermesinum EN-480.
abstract: Chermesins A-D (1-4), four new spiromeroterpenoids containing a drimane-type sesquiterpene skeleton, were isolated and identified from the culture extract of Penicillium chermesinum EN-480, an endophytic fungus obtained from the inner tissue of the marine red alga Pterocladiella tenuis. The structures of these new spiromeroterpenoids were elucidated based on detailed spectroscopic analyses, and their absolute configurations were confirmed by single-crystal X-ray diffraction experiments and by ECD data. This is the first report of the crystal structures of spiromeroterpenoids that contain a drimane-type sesquiterpene skeleton with a rare cyclohexa-2,5-dienone unit, which resulted in the unambiguous assignment of their relative and absolute configurations. Compounds 1 and 2 exhibited antibacterial activity against the opportunistic pathogen Micrococcus luteus, with an MIC value of 8 μg/mL.
authors.affiliation: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, 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: Hui
authors.initials: H
authors.lastname: Liu
authors.affiliation: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, 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: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, 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: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, 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: Peng
authors.initials: P
authors.lastname: Zhang
authors.affiliation: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, 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: Jia-Ning
authors.initials: JN
authors.lastname: Wang
authors.affiliation: Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, 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: D018360:Crystallography, X-Ray; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013141:Spiro Compounds; C000610475:chermesin A; C000610476:chermesin B; C437376:drimane