Two New Cerebrosides and Anthraquinone Derivatives from the Marine Fungus Aspergillus niger

Abstract

Two new cerebrosides, asperiamide B (1) and C (2), and two known aflatoxins, averufin and nidurufin, have been isolated from a Quanzhou marine fungus Aspergillus niger (MF‐16), and the structures were elucidated by spectroscopic data and chemical means. Among the compounds 5 and 6 showed moderate activities in inhibiting multiplication of the Tobacco Mosaic Virus (TMV).

Safety of the fungal workhorses of industrial biotechnology: update on the mycotoxin and secondary metabolite potential of Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei

“…A strain identified as A. niger was reported to produce asperiamide B and C (Wu et al 2008 ), but it also produces the aflatoxin precursors averufin and nidurufin, so this strain was probably an A. flavus .…”

Glycosylated Natural Products From Marine Microbes

“…Two cerebroside analogs, flavicerebrosides A and B (157-158, Figure 12), were obtained from the cultivated mycelium of the marine-derived fungus Aspergillus flavipes, isolated from the sea anemone Anthopleura xanthogrammica and exhibited cytotoxic activity against the KB cell line with IC 50 values of 20.1 and 14.3 µg/ml, respectively (Jiang et al, 2004). The Quanzhou marine fungus Aspergillus niger (MF-16) produced another two cerebrosides, asperiamides B and C (159-160, Figure 12; Wu et al, 2008). With the constant effort to isolate microbes from hypersaline environments, the marine-derived halotolerant fungal strain (THW-18), Alternaria raphani, was isolated and afforded three cerebrosides, alternarosides A-C (161-163, Figure 12).…”

Aspergillus niger: A Hundred Years of Contribution to the Natural Products Chemistry

“…Sphingolipids containing unprecedent 9-methyl-C20-sphingosine moiety were found in A. niger (160-163, Figure 14). 92,93 Asperamides A (160) and B (161), a sphingolipid and its corresponding glycosphingolipid, Tensyuic acid E (127) Tensyuic acid F (128) Figure 9. Chemical structures of terpenes (129-138) produced by A. niger strains.…”

“…92 Asperiamides B (162) and C (163) were produced by A. niger isolated from seawater collected in Fujian Province in China (MF 16). 93 However, in a recent review, 74 the authors pointed out that the same strain was able to produce the aflatoxin precursors averufin and nidurufin and suggested that this strain was probably A. flavus instead of A. niger.…”

“…The miscellaneous group comprises those less representative or unique compounds (164-213, Figure 15, Table 12). [41][42][43]57,69,70,81,84,[93][94][95][96][97][98][99][100][101][102][103][104][105][106][107][108][109][110][111][112] Antafumicins A (166) and B (167), isolated from a collection A. niger strain, inhibited the germination of the fungi Colletotrichum lagenarium, Pyricularia oryzae, Fusarium oxysporum and Botrytis cinerea, as well as the bacteria B. subtilis, E. coli and Aeromonas liquefaciens. 95 Aspernigrin B (172) was obtained from a marine strain isolated from the sponge Axinella damicornis and displayed a pronounced neuroprotective effect against glutamic acid.…”