Antioxidant bisabolane-type sesquiterpenoids from algal-derived fungus Aspergillus sydowii EN-434
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Antioxidant bisabolane-type sesquiterpenoids from algalderived fungus Aspergillus sydowii EN-434* HU Xueyi1, 2, LI Xiaoming1, 3, MENG Linghong1, 3, **, WANG Bingui1, 3, ** 1
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, and Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266071, China
2
College of Earth Science, University of Chinese Academy of Sciences, Beijing 100049, China
3
Center for Ocean Mega-Science, Chinese Academy of Sciences, Qingdao 266071, China
Received Jan. 23, 2020; accepted in principle Apr. 3, 2020; accepted for publication May 5, 2020 © Chinese Society for Oceanology and Limnology, Science Press and Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract A new aromatic bisabolene-type sesquiterpenoid (7S,8S)-8-hydroxysydowic acid (1), together with a pair of new bisabolene derivative (±)-(7R*,10R*)-10-hydroxysydowic acid (2), as well as two known analogues hydroxysydonic acid (3) and sydowic acid (4) were isolated and identified from the endophytic fungal strain Aspergillus sydowii EN-434 that was obtained from the marine red alga Symphyocladia latiuscula. Their structures were elucidated by nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), and quantum chemical electronic circular dichroism (ECD) calculations as well as comparison of the data with literature reports. Compound 1 exhibited potent DPPH free radical scavenging activity with IC50 value of 113.5 μmol/L. Keyword: Aspergillus sydowii; algal-derived fungus; bisabolene-type sesquiterpenoid; antioxidant activity
1 INTRODUCTION Marine-derived fungi are important part of marine microbiological environments and can be found in all habitats (Tasdemir, 2017). Following the discovery of penicillin, fungi hold great potential to discover novel bioactive agents for drug development (Schinke et al., 2017; Barzkar et al., 2019). Since the mid of 1990s, the popularity of the Ascomycota, especially species from the genus Aspergillus, displayed a very rapid growth (Blunt et al., 2015). Aspergillus sydowii has attracted much attention due to the discovery of various bioactive secondary metabolites, such as cyclopentanoids (Teuscher et al., 2006), trispyrogallol ethers (Liu et al., 2013), diphenyl ethers (Wang et al., 2018), sesquiterpenes (Trisuwan et al., 2011; Xu et al., 2017), xanthones (Trisuwan et al., 2011; Wang et al., 2018), diketopiperazine dimer (Cho et al., 2018), and alkaloids (Li et al., 2018). Some of them showed significant antibiotic (Li et al., 2018) and antioxidant (Trisuwan et al., 2011) activities as well as mild cytotoxicity (Liu et al., 2017). Our study started with the purpose of finding new bioactive metabolites from A. sydowii and four
compounds (Fig.1), including a new aromatic bisabolene-type sesquiterpenoid (7S,8S)-8hydroxysydowic acid (1), a pair of new bisabolene derivative (±)-(7R*,10R*)-10-hydroxysydowic acid (2), and two known b
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