Alkaloids from Aspergillus

Spilsbury, J. F., and S. Wilkinson The Isolation of Festuclavine and Two New Clavine Alkaloids from Aspergillus Fumigatus Fres. J. chem. Soc. [London] 1961, 2085. 

Originally there was some debate of the structure of flavipucine (syn. glutamicine) an alkaloid from Aspergillus flavipes, however the constitution (106) has been deduced by X-ray crystallography (P.S. White, J.A. Findlay and W.H.J. 

Williams and co-workers reported the non-enantioselective total syntheses of the heptacyclic indole alkaloids notoamide B (227) and stephacidin A (225) (Scheme 43) [168], and of their probable biogenetic precursor, notoamide C (213) (Scheme 41) [169]. The notoamides are fungal indole alkaloids from Aspergillus species collected fi-om the common mussel Mytilus edulis off Noto Island in the Sea of Japan [170, 171]. There is also a synthesis of the closely related notoamide J (217) (Scheme 42) [172]. 

Chart 5. Quinazoline alkaloids from Aspergillus spec. 

Scherlach K, Hertweck C (2006) Discovery of aspoquinolones A-D, prenylated quinoline-2-one alkaloids, from Aspergillus nidulans, motivated by genome mining. Org Biomol Chem 4 3517-3520... 

Spilsbury, J.F. and Wilkinson, S. (1961) The isolation of festuclavine and two new clavine alkaloids from Aspergillus fumigatus Fres./. Ghent. Soc., 398, 2085-2091. 

A Papua New Guinea sponge, Pseudoceratina sp., contains the unusual alkaloids ceratamines A (1142) and B (1143), and a biogenesis involving histidine and tyrosine is proposed (1173). The fermentation broth from Aspergillus fischeri var. thermomutatus has yielded CJ-12662 (1144) and UK-88051 (1145) (1174). The former metabolite was confirmed by X-ray spectroscopy and partial synthesis. A marine-derived Streptomyces sp. produces the novel pyrrolizidine 5-chlorobohem-amine C (1146), which was shown not to be an isolation artifact (1175). The Chinese medicinal plant Huperzia serrata has furnished 2-chlorohyperzine E (1147) (1176). 

Not surprisingly, a number of new applications of 3 mm NMR probe capabilities were reported in the area of natural product structure determination during 2001. The first of a number of 2001 papers published in the Journal of Natural Products reported the elucidation of the structure of circumdatin G (65), a new alkaloid from the fungus Aspergillus ochraceus.140... 

Ergot alkaloids, from Claviceps purpurea and species of Aspergillus, Rhizopus, and Penicillium. 

In the presence of suitable nucleophiles (such as benzoyl acetic acid) the primary imines can be spontaneously further modified in situ. A convenient approach to obtain phenacyl-derivatives, building blocks in the synthesis of certain alkaloids, was reported 38. In some cases, diamine oxidases exhibit activities complementary to monoamine oxidases. For example vanillylamine is far more efficiently converted into vanillin by a diamine oxidase from Aspergillus niger than by the monoamine oxidase from E. coIi[1 L... 

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,... 

The fungal alkaloids seem to be characteristic in utilizing amino acid itself as its component in contrast to the higher plant alkaloids which are biosynthesized mainly from the amine produced by decarboxylation of amino acid (7,2,5). In this chapter, discussion is limited to fungal alkaloidal metabolites isolated from Aspergillus species, which are classified by biogenetic category. 

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