Diisoprenyl-cyclohexene-type meroterpenoids from a mangrove endophytic fungus Aspergillus sp. GXNU-Y65 and their anti-nonalcoholic steatohepatitis activity in AML12 cells

Feng Qin; Li Luo; Yu-Chen Liu; Xiang-Long Bo; Fu-Rong Wu; Fan-Fan Wang; Mei-Jing Tan; You-Quan Wei; Xiao-Bing Dou; Cai Yi Wang; Xi-Shan Huang; Heng-Shan Wang

doi:10.1016/j.phytochem.2023.113955

Diisoprenyl-cyclohexene-type meroterpenoids from a mangrove endophytic fungus Aspergillus sp. GXNU-Y65 and their anti-nonalcoholic steatohepatitis activity in AML12 cells

Phytochemistry. 2024 Feb:218:113955. doi: 10.1016/j.phytochem.2023.113955. Epub 2023 Dec 19.

Authors

Feng Qin¹, Li Luo², Yu-Chen Liu³, Xiang-Long Bo², Fu-Rong Wu², Fan-Fan Wang⁴, Mei-Jing Tan², You-Quan Wei², Xiao-Bing Dou³, Cai Yi Wang⁵, Xi-Shan Huang⁶, Heng-Shan Wang⁷

Affiliations

¹ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People's Republic of China; Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin 537000, People's Republic of China.
² State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People's Republic of China.
³ College of Life Science, Zhejiang Chinese Medical University, Hangzhou, Zhejiang, 310053, People's Republic of China.
⁴ Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin 537000, People's Republic of China.
⁵ College of Life Science, Zhejiang Chinese Medical University, Hangzhou, Zhejiang, 310053, People's Republic of China. Electronic address: [email protected].
⁶ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People's Republic of China. Electronic address: [email protected].
⁷ State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources/Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People's Republic of China. Electronic address: [email protected].

PMID: 38128773
DOI: 10.1016/j.phytochem.2023.113955

Abstract

Nine previously undescribed diisoprenyl-cyclohexene-type meroterpenoids, aspergienynes A-I, together with five known analogues, were obtained from the mangrove endophytic fungal strain Aspergillus sp. GXNU-Y65. The diisoprenyl-cyclohexene-type meroterpenoids were elucidated based on multispectroscopic analysis, and the previously undescribed compounds' absolute configurations were established via electronic circular dichroism calculations. Biological activity results indicated that aspergienyne C (compound 3) had strong anti-nonalcoholic steatohepatitis activity against AML12 cells treated with PA (Palmitic acid) + OA (Oleic acid). At the same concentration of 20 μM, 3 significantly reduced triglyceride (TG) content compared with fenofibrate (positive control) in PA + OA treated AML12 cells, and obviously increased phosphorylation of acetyl-CoA carboxylase.

Keywords: Anti-nonalcoholic steatohepatitis activity; Aspergienynes a-I; Aspergillus sp; Diisoprenyl-cyclohexene; Meroterpenoids.

MeSH terms

Aspergillus* / chemistry
Circular Dichroism
Fatty Liver*
Molecular Structure