Structurally diverse secondary metabolites from a deep-sea-derived fungus Penicillium chrysogenum SCSIO 41001 and their biological evaluation

Shengtian Chen; Junfeng Wang; Zhen Wang; Xiuping Lin; Bingxin Zhao; Kumaravel Kaliaperumal; Xiaojian Liao; Zhengchao Tu; Jianlin Li; Shihai Xu; Yonghong Liu

doi:10.1016/j.fitote.2017.01.005

Structurally diverse secondary metabolites from a deep-sea-derived fungus Penicillium chrysogenum SCSIO 41001 and their biological evaluation

Fitoterapia. 2017 Mar:117:71-78. doi: 10.1016/j.fitote.2017.01.005. Epub 2017 Jan 17.

Authors

Affiliations

¹ Department of Chemistry, Jinan University, Guangzhou 510632, China; CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
² CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
³ Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China.
⁴ Department of Chemistry, Jinan University, Guangzhou 510632, China.
⁵ School of Pharmacy, Nantong University, Nantong 226001, China.
⁶ Department of Chemistry, Jinan University, Guangzhou 510632, China. Electronic address: txush@jnu.edu.cn.
⁷ CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China; South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, China. Electronic address: yonghongliu@scsio.ac.cn.

PMID: 28108327
DOI: 10.1016/j.fitote.2017.01.005

Abstract

Five new compounds, including a cytotoxic dimeric isocoumarin, bipenicilisorin (1), a merosesquiterpenoid, yaminterritrem C (2), a citrinin dimer, penicitrinone F (3), a alkaloid, terremide D (4), and a δ-valerolacton, (E)-4-(propen-1-yl)-5,6-dihydro-2H-pyran-2-one (5), along with ten known compounds (6-15) were isolated from a deep-sea-derived fungus Penicillium chrysogenum SCSIO 41001. Their structures and absolute configurations were elucidated by NMR spectra, MS, CD, optical rotation, X-ray crystallography, and compared with literature data. Biological evaluation results revealed that 1 exhibited significant cytotoxic activities against K562, A549, and Huh-7 cell lines with IC₅₀ values of 6.78, 6.94, and 2.59μM, respectively. Compound 3 exhibited moderate inhibitory activity against EV71 with IC₅₀ value of 14.50μM. In addition, 13 and 14 showed specific COX-2 inhibitory activities with IC₅₀ values of 1.09 and 1.97μM, respectively.

Keywords: Alkaloid; COX-2; Citrinin dimer; Cytotoxic; Isocoumarin; Merosesquiterpenoid.

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Cell Line, Tumor
Citrinin / analogs & derivatives
Citrinin / chemistry*
Citrinin / isolation & purification
Crystallography, X-Ray
Cyclooxygenase Inhibitors / chemistry
Cyclooxygenase Inhibitors / isolation & purification
Humans
Inhibitory Concentration 50
Isocoumarins / chemistry
Isocoumarins / isolation & purification
Molecular Structure
Penicillium chrysogenum / chemistry*
Seawater / microbiology
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification

Substances

Alkaloids
Antineoplastic Agents
Cyclooxygenase Inhibitors
Isocoumarins
Sesquiterpenes
penicitrinone F
Citrinin