Quinazoline-Containing Indole Alkaloids from the Marine-Derived Fungus Aspergillus sp. HNMF114

Abstract

Seven new quinazoline-containing indole alkaloids (1–7) named aspertoryadins A–G, along with nine known ones (8–16), were isolated from the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis. The structures of the new compounds were elucidated from spectroscopic data, X-ray diffraction analysis, ECD spectra analysis, and ECD calculations. Compound 1 bears an aminosulfonyl group in the structure, which is rarely encountered in natural products. Compounds 6, 7, and 13 exhibited quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with MIC values of 32, 32, and 16 μg/well, respectively.

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

“…HNMF114 supplemented with L -tryptophan was carried out, which led to the isolation of 3 new quinazoline-containing indole alkaloids, aspertoryadins H–J ( 1 – 3 ), along with 16 known ones, tryptoquivaline H ( 4 ) ( Buttachon et al, 2012 ), norquinadoline A ( 5 ) ( Peng et al, 2013 ), epi -fiscalin D ( 6 ) ( Qian et al, 2018 ), epi -fiscalin A ( 7 ) ( Buttachon et al, 2012 ), deoxynortryptoquivaline ( 8 ) ( Lin et al, 2013 ), scequinadolines D ( 9 ) ( Huang et al, 2017 ), lapatin A ( 10 ) ( Wu and Ma, 2013 ), fiscalin A ( 11 ) ( Buttachon et al, 2012 ), oxoglyantrypine ( 12 ) ( Peng et al, 2013 ), quinadoline B ( 13 ) ( Koyama et al, 2008 ), tryptoquivalines L ( 14 ) ( Buttachon et al, 2012 ), quinadoline A ( 15 ) ( Koyama et al, 2008 ), scequinadolines E ( 16 ) ( Huang et al, 2017 ), scequinadoline G ( 17 ) ( Huang et al, 2017 ), glyantrypine ( 18 ) ( Penn et al, 1992 ), and tryptoquivalines F ( 19 ) ( Buttachon et al, 2012 ) ( Figure 1 ). Interestingly, these compounds were all different from those of our previous report ( Kong et al, 2019 ). Herein, the isolation, structure elucidation, and bioactivities of these compounds are reported.…”

“…The fungal information of Aspergillus sp. HNMF114 has been described in our previous report (Kong et al, 2019).…”

“…to those of aspertoryadin A (Kong et al, 2019), indicating that they had a similar skeleton. The obvious structural difference between them is that a hydrogen on N-15 in 2 replaced the methyl sulfonyl group in aspertoryadin A.…”

“…HNMF114 was isolated and identified from a bivalve mollusk, Sanguinolaria chinensis, collected in Haikou Bay, China. Our previous research (Kong et al, 2019) on the secondary metabolites of this fungus reported a series of quinazoline-containing indole alkaloids. Biogenetically, these compounds are all derived from tryptophan and anthranilic acid, along with other amino acids.…”

Marine-derived fungi as a source of bioactive indole alkaloids with diversified structures

“…HNMF114 from the bivalve mollusk Sanguinolaria chinensis. Notably, compounds 320 and 321 exhibited quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with the MICs of 32.0, 32.0 μg/well, respectively (Kong et al 2019b). Another two analogs, tryptoquivalines R and S (322 and 323), were isolated from a marine-derived fungus Neosartorya sp.…”