Meroterpenoid and Diphenyl Ether Derivatives from Penicillium sp. MA-37, a Fungus Isolated from Marine Mangrove Rhizospheric Soil

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2012-11, Vol.75 (11), p.1888-1895
• Main Authors: Zhang, Yi, Li, Xiao-Ming, Shang, Zhuo, Li, Chun-Shun, Ji, Nai-Yun, Wang, Bin-Gui
• Format: Article
• Language: English
• Subjects: Animals; Anti-Bacterial Agents - chemistry; Artemia - drug effects; Bruguiera gymnorrhiza; Crystallography, X-Ray; Drug Screening Assays, Antitumor; Fermentation; Marine; Marine Biology; Microbial Sensitivity Tests; Molecular Structure; Penaeidae; Penicillium; Penicillium - chemistry; Phenyl Ethers - chemistry; Phenyl Ethers - isolation & purification; Phenyl Ethers - pharmacology; Rhizophoraceae - microbiology; Soil Microbiology; Terpenes - chemistry; Terpenes - isolation & purification; Terpenes - pharmacology
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np300377b

Penicillium sp. MA-37, which was obtained from the rhizospheric soil of the mangrove plant Bruguiera gymnorrhiza, exhibited different chemical profiles in static and shaken fermentation modes. Three new meroterpenoid derivatives, 4,25-dehydrominiolutelide B (1), 4,25-dehydro-22-deoxyminiolutelide B (2), and isominiolutelide A (3), together with three known ones were characterized from its static fermentation, while three new diphenyl ether derivatives, namely, Δ1′,3′ -1′-dehydroxypenicillide (4), 7-O-acetylsecopenicillide C (5), and hydroxytenellic acid B (6), along with five related metabolites were isolated from the shaken culture. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the structure of compound 2 was confirmed by X-ray crystallographic analysis. The absolute configurations of 1–3 and 6 were determined by ECD and modified Mosher’s method, respectively. All isolated compounds were evaluated for brine shrimp lethality and antibacterial activity.