**4. Conclusions**

To summarize, two new indole alkaloid dimers di-6-hydroxydeoxybrevianamide E (**1**), dinotoamide J (**2**) and one new pteridine alkaloid asperpteridinate A (**3**), together with eleven known compounds (**4**–**14**) were isolated from the marine-derived fungus *Aspergillus austroafricanus* Y32-2. Their structures including the absolute configurations were elucidated by various spectroscopic methods and ECD calculations. Among them, both di-6-hydroxydeoxybrevianamide E (**1**) and dinotoamide J (**2**) are homologous dimers that represent the novel examples of prenylated indole alkaloids. Asperpteridinate A is the first new alkaloid composed of pteridine and 1, 3-benzodioxole structures. All compounds were evaluated for pro-angiogenic, anti-inflammatory activities in the zebrafish models and cytotoxicity against HepG2 cells. Compounds **2**, **4**, **5**, **7**, and **10** exhibited pro-angiogenic activity, and compounds **7**, **8**, **10**, and **11** displayed anti-inflammatory activity in a dosedependent manner, and compound **6** showed significant cytotoxicity against HepG2 cells with an IC50 value of 30 μg/mL. The results suggested that these compounds could be promising candidates for further pharmacologic and biosynthetic research.

**Supplementary Materials:** The following are available online at https://www.mdpi.com/1660-339 7/19/2/98/s1, HRESIMS, 1D and 2D NMR spectra of all new compounds **1**–**3**, biological activities of all isolated compounds and dose–response curves of compound **6**, the atom coordinates and energies of new compounds **1**–**3**.

**Author Contributions:** P.L. performed isolation, structure determination and bioassays of the compounds and wrote the manuscript. M.Z. performed the fermentation of the fungus, extraction of the culture broths and isolation of the compounds. H.L. and R.W. performed the bioassays. H.H. carried out taxonomic identification of the fungus. X.L. and K.L. designed the study and revised the manuscript. H.C. collected the samples from the Indian Ocean and revised the manuscript. All authors have read and agreed to the published version of the manuscript.

**Funding:** This work was supported by the National Key R&D Program of China (2018YFC1707300), the Project funded by China Postdoctoral Science Foundation (2019M662418), the International Science and Technology Cooperation Program of Shandong Academy of Sciences (No. 2019GHZD10), the Foundation of State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology, Shandong Academy of Sciences (No. ZZ20190402), the National Natural Science Foundation of China (81602982), the Taishan Scholar Project from Shandong Province (ts20190950), and the China Ocean Mineral Resources Research and Development Association (DY135-R2-1-06 and DY135-B2-11).

**Institutional Review Board Statement:** The experiments were performed in accordance with standard ethical guidelines. The procedures were approved by the Ethics Committee of the Biology Institute of Shandong Academy of Science (SYXK LU 2020 0015).

**Conflicts of Interest:** The authors declare no conflict of interest.
