Chlorinated Azaphilone Pigments with Antimicrobial and Cytotoxic Activities Isolated from the Deep Sea Derived Fungus Chaetomium sp. NA-S01-R1

Weiyi Wang; Yanyan Liao; Ruixuan Chen; Yanping Hou; Wenqian Ke; Beibei Zhang; Maolin Gao; Zongze Shao; Jianming Chen; Fang Li

doi:10.3390/md16020061

Chlorinated Azaphilone Pigments with Antimicrobial and Cytotoxic Activities Isolated from the Deep Sea Derived Fungus Chaetomium sp. NA-S01-R1

Mar Drugs. 2018 Feb 13;16(2):61. doi: 10.3390/md16020061.

Authors

Weiyi Wang¹, Yanyan Liao², Ruixuan Chen³, Yanping Hou⁴, Wenqian Ke⁵, Beibei Zhang⁶, Maolin Gao⁷, Zongze Shao⁸, Jianming Chen⁹, Fang Li¹⁰

Affiliations

¹ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. wywang@tio.org.cn.
² Key Laboratory of Urban Environment and Health, Institute of Urban Environment, Chinese Academy of Sciences, Xiamen 361021, China. yyliao@iue.ac.cn.
³ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. 18606928642@163.com.
⁴ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. houyanping@tio.org.cn.
⁵ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. 15260587285@163.com.
⁶ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. zbb953372968@163.com.
⁷ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. g17785208284@163.com.
⁸ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. shaozongze@tio.org.cn.
⁹ Institute of Oceanography, Minjiang University, Fuzhou 350108, China. chenjianming@tio.org.cn.
¹⁰ State Key Laboratory Breeding Base of Marine Genetic Resources, Key Laboratory of Marine Genetic Resources, Fujian Key Laboratory of Marine Genetic Resources, Fujian Collaborative Innovation Centre for Exploitation and Utilization of Marine Biological Resources, Third Institute of Oceanography, State Oceanic Administration, Xiamen 361005, China. lifang@tio.org.cn.

Abstract

Four novel compounds, chaephilone C (1), chaetoviridides A-C (2-4), were obtained from the culture of a deep sea derived fungus Chaetomium sp. NA-S01-R1, together with four known compounds-chaetoviridin A (5), chaetoviridine E (6), chaetomugilin D (7) and cochliodone A (8). Their structures, including absolute configurations, were assigned based on NMR, MS and time-dependent density functional theory (TD-DFT) ECD calculations. A plausible biogenetic pathway for compounds 1-3 was proposed. Compounds 2 and 3 exhibited antibacterial activities against Vibrio rotiferianus and Vibrio vulnificus. Compounds 1, 3 and 4 displayed similar anti-methicillin resistant Staphylococcus aureus (anti-MRSA) activities in comparison to chloramphenicol. Compound 2 showed the most potent cytotoxic activities towards the Hep G2 cell and compounds 1 and 3 demonstrated relatively stronger cytotoxic activities than the other compounds against the HeLa cell.

Keywords: Chaetomium; antimicrobial; chaephilone; chaetoviridide; cytotoxic.

MeSH terms

Anti-Bacterial Agents / pharmacology*
Antibiotics, Antineoplastic / pharmacology*
Benzopyrans / pharmacology*
Cell Line, Tumor
Chaetomium / chemistry*
Chloramphenicol / pharmacology
Fermentation
HeLa Cells / drug effects
Humans
Magnetic Resonance Spectroscopy
Mass Spectrometry
Methicillin-Resistant Staphylococcus aureus / drug effects
Microbial Sensitivity Tests
Molecular Structure
Pigments, Biological / pharmacology*
Seawater / microbiology
Vibrio / drug effects

Substances

Anti-Bacterial Agents
Antibiotics, Antineoplastic
Benzopyrans
Pigments, Biological
azaphilone
Chloramphenicol