Prenylated indole alkaloids from co-culture of marine-derived fungi Aspergillus sulphureus and Isaria felina

Abstract

Five new prenylated indole alkaloids, 17-hydroxynotoamide D (1), 17-O-ethylnotoamide M (2), 10-O-acetylsclerotiamide (3), 10-O-ethylsclerotiamide (4), and 10-O-ethylnotoamide R (5) were isolated from a co-culture of marine-derived fungi Aspergillus sulphureus KMM 4640 and Isaria felina KMM 4639. The structures of 1-5 were determined by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1-5 were determined by time-dependent density functional theory (TD-DFT) calculations of ECD spectra. Compound 2 is able to inhibit the colony formation of human prostate cancer cells 22Rv1 at non-cytotoxic concentration of 10 μM.

Recent Discovery of Heterocyclic Alkaloids from Marine-Derived Aspergillus Species

“…Z-4, which was derived from the marine isopod Ligia oceanica [35][36][37]. Compound 31 was characterized as a new prenylated indole alkaloid, which was isolated from a coculture of the marine-derived fungi A. sulphureus KMM 4640 and Isaria felina KMM 4639 [38].…”

“…Figure 2 lists the structures of diketopiperazine alkaloids that are produced by marine-derived Aspergillus species. Compounds 32-35 were isolated from a coculture of the marine sediment-derived fungi A. sulphureus KMM 4640 and Isaria felina KMM 4639 and identified as four new prenylated indole diketopiperazine alkaloids [38]. Compounds 36-43 were characterized as eight linearly fused prenylated indole diketopiperazines featuring an unusual pyrano[3,2-f]indole unit, which were isolated from the culture of a fungal strain, A. versicolor, residing in mud from the South China Sea [40].…”

The Structural Diversity of Marine Microbial Secondary Metabolites Based on Co-Culture Strategy: 2009–2019

“…Bacteria and bacteria (6), notoamide C (7), dehydronotoamide C (8), notoamide D (9), notoamide F (10), notoamide Q (11), 17-epi-notoamide Q (12), notoamide M (13) and sclerotiamide (14) (Figure 4) [17]. Among them, compounds 1-5 were only produced in the co-culturingprocess.…”

“…The co-fermentation of marine mangrove epiphytic fungi Aspergillus sp. FSY-01 and FSW-02 collected from a rotten fruit of mangrove Avicennia marina in Zhanjiang, Guangdong Province, China, yielded a new alkaloid, aspergicin (15), together with two known secondary metabolites, neoaspergillic acid (16) and aspergicine (17) (Figure 5) [20,21]. Notably, compounds 17 and 15 are chemically isomers, and consequently aspergicine (17) may be the precursor of aspergicin (15) through a proton 1, 2-shift [22].…”

Achievements in the Study of Marine Low‐Molecular Weight Biologically Active Metabolites from the Vietnamese Territorial Waters as a Result of Expeditions aboard the Research Vessel ‘Akademik Oparin’ (2004–2017)

“…Diorcinol B (81) reduced the heat shock protein Hsp70 level in Ehrlich carcinoma cells at a concentration of 10 μM and can be considered as a potential antitumor compound. [38] [39] The marine-derived fungus Penicillium citrinum was isolated from soft coral of the Zoantharia family. Four sesquiterpenoids, JBIR-27 (99), petasol (100), sporogen AO-1 (101), and dihydrosporogen AO-1 (102), were isolated from the ethyl acetate extract of this fungus.…”