Eupenicillium

Another natural product, mizoribiae (39), a nucleoside antibiotic produced by the fungus Eupenicillium brefeldianum has cytotoxic and immunosuppressive activity. It has been evaluated for use ia renal transplantation and neoplasia (68). 

Bredinin, Neosidomycin, and SF-2140. Bredinin (62), isolated from the culture filtrates of Eupenicillium brefeldianum (1,4), inhibits the multiplication of L5178Y, HeLa S3, RK-13, mouse L-ceUs, and Chinese hamster cells. GMP can reverse the inhibition by (62), but (62) is not incorporated into the nucleic acids. The inhibition of nucleic acid synthesis and chromosomal damage in the S and G 2 phases that is caused by (62), is reversed by GMP. It blocks the conversion of IMP to XMP and XMP to GMP. In combination with GMP, (62) interferes with intracellular cAMP levels and thereby inhibits cell division. 

Isolation from cultures of Eupenicillium hrefeldianum NRRL 5734. a Amberlite IRA-411/pH 10. b Chromatography on DEAE-Sephadex A-25. 

Cl HO— y m Fungi -Eupenicillium HjN CO2H Kaitocephalin - antagonist of glutamate receptor 260... 

Watanabe M et al (2005) Cloning and characterization of saponin hydrolases from Aspergillus oryzae and Eupenicillium brefeldianum. Biosci Biotechnol Biochem 69(11) 2178 Osbourn A (1996) Preformed antimicrobial compounds and plant defence against fungal attack. Plant Cell 8 1821... 

Murraya paniculata Eupenicillium sp. alanditrypinone A and B, alantryphenone, alantrypinene, alantryleunone 246... 

Davis RA et al, Phomoxins B and C Polyketides from an endophytic fungus of the genus Eupenicillium, Phytochemistry 66 2771—2775, 2005. 

Bredinin, Neosidomycin, and SF-2140. Bredinin (CiyH NjO, ) isolated from the culture filtrates of Eupenicillium brefeldianum, inhibits the multiplication of L5I78Y, HeLa 83, RK-13, mouse L-cells, and Chmese hamster cells. 

Shin-ya K, Kim J-S, Furihata K, Hayakawa Y, Seto H (1997) Structure of Kaitocephalin, a Novel Glutamate Receptor Antagonist Produced by Eupenicillium shearii. Tetrahedron Lett 38 7079... 

Pitt, J. I. (1979), The genus Penicillium and its teleomorphic states Eupenicillium and Talaromyces, Academic Press, London, UK. 

It has also been proposed that the presence of endophytes can alter the usual suite of secondary metabolites of plants. For example, whilst Murraya spp. have been reported to produce indole and carbazole alkaloids, the Brazilian M. paniculata did not [25]. An endophytic Eupenicillium sp. was isolated from surface-sterilized leaf material of the Brazilian M. paniculata and subsequently cultured on white corn. The Eupenicillium sp. produced hydrophobic spiroquinazoline alkaloids that were separated using silica gel column chromatography and preparative gel-filtration... 

Fig. 13.7 The common fragment ion indicative of the spiroquinazoline alkaloids isolated from a Murraya paniculata endophyte, Eupenicillium spp.

Leal J.A., Guerrero C., Gomez-Miranda B., Prieto A. and Bemabe M. (1992) Chemical and structural similarities in wall polysaccharides of some Penicillium, Eupenicillium and Aspergillus species. FEMS Microbiol. Lett., 90, 165-168. 

Eupenicillium terrenum D-Fructose-dipeptide/a-amino acid 260... 

Xanthofulvin (1004) was first isolated by Masubuchi and co-workers from a Eupenicillium strain and found to be a chitin synthase II inhibitor (/C50 = 2.2 pM). Kimura and co-workers reported the isolation of SM-216289 or xanthofulvin (1004, Fig. 13.22) in addition to the known tautomer, vinaxanthone (991, (Fig. 13.21), from cultures of Penicillium sp. SPF-3059 (660). The authors demonstrated that xanthofulvin (1004) (Fig. 13.22) is also a semaphorin inhibitor (see vinaxanthmie, above) Sema3A was inhibited at a low concentration level (JCso = 0.16 pM). 

Numbering systems vary. Metab. of the ascostromata of Eupenicillium shearii. Oil. [ol — 12 (c, 0.30 in CHCI3). 

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