Three New Quinazoline-Containing Indole Alkaloids From the Marine-Derived Fungus Aspergillus sp. HNMF114

Sha-Sha Liu; Li Yang; Fan-Dong Kong; Jia-Hui Zhao; Li Yao; Zhi-Guang Yuchi; Qing-Yun Ma; Qing-Yi Xie; Li-Man Zhou; Meng-Fei Guo; Hao-Fu Dai; You-Xing Zhao; Du-Qiang Luo

doi:10.3389/fmicb.2021.680879

Three New Quinazoline-Containing Indole Alkaloids From the Marine-Derived Fungus Aspergillus sp. HNMF114

Front Microbiol. 2021 Jun 2:12:680879. doi: 10.3389/fmicb.2021.680879. eCollection 2021.

Authors

Sha-Sha Liu¹, Li Yang², Fan-Dong Kong³, Jia-Hui Zhao⁴, Li Yao⁴, Zhi-Guang Yuchi⁴, Qing-Yun Ma², Qing-Yi Xie², Li-Man Zhou³, Meng-Fei Guo³, Hao-Fu Dai⁵, You-Xing Zhao², Du-Qiang Luo¹

Affiliations

¹ College of Life Science, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding, China.
² Haikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, CATAS, Haikou, China.
³ Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning, China.
⁴ Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, Collaborative Innovation Center of Chemical Science and Engineering, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, China.
⁵ Hainan Institute for Tropical Agricultural Resources, CATAS, Haikou, China.

Abstract

By feeding tryptophan to the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis, 3 new quinazoline-containing indole alkaloids, named aspertoryadins H-J (1-3), along with 16 known ones (4-19), were obtained. The structures of the new compounds were elucidated by the analysis of spectroscopic data combined with quantum chemical calculations of nuclear magnetic resonance (NMR) chemical shifts and electron capture detector (ECD) spectra. Structurally, compound 3 represents the first example of this type of compound, bearing an amide group at C-3. Compounds 10 and 16 showed potent α-glucosidase inhibitory activity with IC₅₀ values of 7.18 and 5.29 μM, and compounds 13 and 14 showed a clear activation effect on the ryanodine receptor from Spodoptera frugiperda (sfRyR), which reduced the [Ca²⁺] _ER by 37.1 and 36.2%, respectively.

Keywords: Aspergillus sp.; indole alkaloids; marine-derived fungus; ryanodine receptor; α-glucosidase inhibitory activity.