Aspergillus ustus

One of the indole diketopiperazines 24, metabolite Aspergillus Ustus from mold spores forming in corn grains, has a pentacyclic structure with an azocino[5,4- 7]indole fragment (73X107). 

We have recently isolated two new ophiobolins, G and H, from a novel source, Aspergillus ustus (ATCC No. 38849) (16) (Figures 5 and 6). Structurally, these two compounds are interesting in that the ring fusion between rings A and B is trans, as opposed to cis in the ophiobolins previously described from other fungal sources. In this respect these new metabolites more closely resemble the ophiobolins extracted from insects. Structural features common to both the insect and fungal ophiobolins are the double bonds at C7-C8 and C18-C19. Ophiobolins G and H are unique in the possession of a C16-C17 cis double bond. 

Perhaps the method can be shown better by a description of the isolation of a new antibiotic in our laboratory 4). Antibiotic activity had been demonstrated in ether extracts from the mold Aspergillus ustus. 

VI. Isolation of Antibiotic Principles from Aspergillus ustus. J. biol. Chem. 162, 363 (1946). 

Fig. 13. 0-Isotopically shifted resonances in the 100.6 MHz p.n.d. NMR spectrum of austin (89) enriched by feeding [ C, O]-3,5-dimethylorsellinate to Aspergillus ustus...

I. (-)-AUSTALIDE B, AN ORTHO ESTER MEROTERPENOID MYCOTOXIN PRODUCED BY ASPERGILLUS USTUS... 

Austalides A-F (185-190) have gained prominence as a result of their discovery as toxigenic agents produced in dried fish by Aspergillus ustus [99-102]. The unique molecular architecture of the metabolites, which is common to all six... 

Monascus ruber Monascus ruber Penicillium rubrum Talaromyces udagawae Penicillium rubrum Penicillium wortmannii Penicillium vermiculatum Penicillium funiculosum Penicillium vermiculatum Talaromyces tardifaciens Penicillium wortmannii Aspergillus ustus... 

Aspergillus ustus produces several novel pentacyclic metabolites, the austocystins, two of which, i.e. A (72) and C (73), contain chlorine [120],... 

Okaramine A (1) is a novel heptacyclic compound containing a hexahydropyrroloindole moiety and a dihydroazocinoindole moiety. The azocinoindole moiety has been reported to constitute only two compounds a metabolite (48) of Aspergillus ustus [31] and cycloechinulin (49) produced by A. ochraceus [32] (Fig. (8)). One of the structural characteristics of the okaramine family is the presence of a reverse-prenylated hexahydro[2,3-Z>]pyrroloindole moiety. Some related... 

Aspergillus ustus Aspergillus variecolor Penicillium diversum Emericella denlata... 

Non-terpenoid Alkaloids.— The structure (14) adduced for austamide, a metabolite from Aspergillus ustus, is based principally on a thorough n.m.r. analysis [see data on (14)]. Like the brevianamides it is made up of proline,... 

Austocystins. The A. A to I are antimicrobially active and mutagenic metabolites of Aspergillus ustus. They are structurally related to sterigmatin from Aspergillus versicolor. Biogenetically they are derived... 

Ophiobolins. Phytotoxic sesterterpenoids derived from the unusual tricyclic skeleton of ophiobolane (C25H46, Mr 346.62). The O. A-M are produced by plant-pathogenic fungi such as Ophiobolus, Helmin-thosporium, Cephalosporium, and Drechslera species as well as by Aspergillus ustus (O. H and O. K), O. M is a potent nematocidal agent. 

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