Brasilane sesquiterpenoids and dihydrobenzofuran derivatives from Aspergillus terreus [CFCC 81836]. (December 2018)

• Record Type: Journal Article
• Authors: Wu, Zhaodi; Li, Dongyan; Zeng, Fanrong; Tong, Qingyi; Zheng, Yinyu; Liu, Junjun; Zhou, Qun; Li, Xiao-Nian; Chen, Chunmei; Lai, Yongji; Zhu, Hucheng; Zhang, Yonghui
• Is Part Of: Phytochemistry. Volume 156(2018)
• Page Start: 159
• Page End: 166
• Publication Date: 2018-12
• Subjects: Aspergillus terreus [CFCC 81836] -- Trichocomaceae -- Brasilane sesquiterpenoids -- Dihydrobenzofuran derivatives -- Anti-inflammation -- Cytotoxicity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.10.006
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Brasilanones A–F and asperterreusines A–C, undescribed brasilane sesquiterpenoids and dihydrobenzofuran derivatives, were isolated from the marine-derived fungus Aspergillus terreus [CFCC 81836]. Their structures with absolute configurations were elucidated on the basis of spectroscopic data, X-ray crystallographic analyses, and electronic circular dichroism (ECD) calculations. Brasilanones A–F are unusual brasilane sesquiterpenoids with an α, β -unsaturated ketone unit, interestingly, brasilanones B–D are stereo isomers. All of the isolates were evaluated for their inhibitory activities against NO production and cytotoxic activities against five human cancer cell lines (HL-60, SW-480, A-549, MCF-7, and SMMC-7721). Brasilanones A and E showed moderate inhibitory effect with NO inhibition rates of 47.7% ( p < 0.001) and 37.3% ( p < 0.001) at the concentration of 40 μ M. Asperterreusines A showed cytotoxicity against HL-60 and SW-480 cell lines with IC50 values of 15.3 and 25.7 μ M, respectively. Graphical abstract: Brasilanones A–F and asperterreusines A–C, undescribed brasilane-type sesquiterpenoids and dihydrobenzofuran derivatives were isolated from Aspergillus terreus [CFCC 81836]. Brasilanones A and E showed moderate anti-inflammatory effect, and asperterreusines A showed moderate cytotoxicity. Image 1 Highlights: Brasilane sesquiterpenoids and dihydrobenzofurans were isolated from Aspergillus terreus. Brasilanones A–F bear α, β -unsaturated ketone units and brasilanones B–D are stereo isomers. Brasilanones A and E showed moderate inhibitory effect against NO production. Asperterreusine A showed moderate cytotoxic activity.