(+)-Geodin from<i>Aspergillus terreus</i>

Rønnest, Mads H.; Nielsen, Morten Ørregaard; Leber, Blanka; Mortensen, Uffe Hasbro; Krämer, Alwin; Clausen, Mads Hartvig; Larsen, Thomas Ostenfeld; Harris, Pernille

doi:10.1107/s0108270111005816

Cited by 12 publications

(11 citation statements)

References 27 publications

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“…The hexadienone ring is rotated by 89.79 (5) with respect to the five-membered ring. This is similar to the values found in related 5/6 spiro-ring fused systems containing the cyclohexadienone moiety that have been reported previously (Lou, 2012;Martins et al, 2014;Rønnest et al, 2011). The phenyl ring is inclined to the five-membered ring by 35.88 (6) , while the planar methyl carboxylate substituent, C3/C16/O4/C17, is inclined to this ring by only 6.61 (13) .…”

Section: Structure Descriptionsupporting

confidence: 89%

Methyl 8-oxo-2-phenyl-1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate

2016

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Section: Structure Descriptionsupporting

confidence: 89%

Methyl 8-oxo-2-phenyl-1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate

2016

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“…36 Geodin (56) is however twice as cytotoxic as griseofulvin when tested against the MDA-MB-231 cell line, with an IC 50 of 9.9 μM opposed to 18 μM for 1.…”

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

“…Nine of the compounds were active against both fungi within the same order of magnitude compared to griseofulvin (17,20,21,23,26,32,36,49, and 54).…”

mentioning

confidence: 91%

Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

et al. 2012

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Griseofulvin and 53 analogues of this compound have been tested against the pathogenic dermatophytes Trichophyton rubrum and Trichophyton mentagrophytes as well as against the breast cancer cell line MDA-MB-231. The modifications to griseofulvin include the 4, 5, 6, 2′, 3′, and 4′ positions. The SAR of the griseofulvin analogues toward the two fungi followed the same trend with the majority being less active than griseofulvin and none had more than twice the potency of the parent compound. A comparison of the antifungal and the anticancer SAR revealed distinct differences, as the majority of analogues showed increased activity against the cancer cell line MDA-MB-231, highlighted by 2′-benzyloxy-2′-demethoxy-griseofulvin, which showed low activity against both fungi but was among the most potent compounds against MDA-MB-231 cancer cells. Tubulin has been proposed as the target of griseofulvin in both fungal and mammalian cells, but the differences revealed by this SAR study strongly suggest that the mode-of-action of the compound class toward fungi and mammalian cancer cells is different.

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“…Antiviral compounds such as acetylaranotin has also been reported from Aspergillus terreus ( Miller et al 1968 , Kamata et al 1983 ). Other secondary metabolites reported to be produced by A. terreus isolates are considered as mycotoxins, including citreoviridin ( Franck & Gehrken, 1980 ), patulin ( Kent & Heatley 1945 , Draughon & Ayres 1980 , Reddy & Reddy 1988 ), citrinin ( Sankawa et al 1983 ), emodin ( Fujii et al 1982 ), terretonin ( Springer et al 1979 , Li et al 2005 ), geodin ( Kiriyama et al 1977 , Rønnest et al 2011 ), territrems ( Ling et al 1979 ), gliotoxin ( Lewis et al 2005 , Kupfahl et al 2008 ), and cytochalasin E ( Fujishima et al 1979 ). Aspergillus terreus is also an important human pathogen, and often causes disseminated infection with increased lethality compared to other Aspergillus spp.…”

Section: Introductionmentioning

confidence: 99%

New species in Aspergillus section Terrei

Samson¹,

Peterson²,

Frisvad³

et al. 2011

Studies in Mycology

121

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Section Terrei of Aspergillus was studied using a polyphasic approach including sequence analysis of parts of the β-tubulin and calmodulin genes and the ITS region, macro- and micromorphological analyses and examination of extrolite profiles to describe three new species in this section. Based on phylogenetic analysis of calmodulin and β-tubulin sequences seven lineages were observed among isolates that have previously been treated as A. terreus and its subspecies by Raper & Fennell (1965) and others. Aspergillus alabamensis, A. terreus var. floccosus, A. terreus var. africanus, A. terreus var. aureus, A. hortai and A. terreus NRRL 4017 all represent distinct lineages from the A. terreus clade. Among them, A. terreus var. floccosus, A. terreus NRRL 4017 and A. terreus var. aureus could also be distinguished from A. terreus by using ITS sequence data. New names are proposed for A. terreus var. floccosus, A. terreus var. africanus, A. terreus var. aureus, while Aspergillus hortai is recognised at species level. Aspergillus terreus NRRL 4017 is described as the new species A. pseudoterreus. Also included in section Terrei are some species formerly placed in sections Flavipedes and Versicolores. A. clade including the type isolate of A. niveus (CBS 115.27) constitutes a lineage closely related to A. carneus. Fennellia nivea, the hypothesized teleomorph is not related to this clade. Aspergillus allahabadii, A. niveus var. indicus, and two species originally placed in section Versicolores, A. ambiguus and A. microcysticus, also form well-defined lineages on all trees. Species in Aspergillus section Terrei are producers of a diverse array of secondary metabolites. However, many of the species in the section produce different combinations of the following metabolites: acetylaranotin, asperphenamate, aspochalamins, aspulvinones, asteltoxin, asterric acid, asterriquinones, aszonalenins, atrovenetins, butyrolactones, citreoisocoumarins, citreoviridins, citrinins, decaturins, fulvic acid, geodins, gregatins, mevinolins, serantrypinone, terreic acid (only the precursor 3,6-dihydroxytoluquinone found), terreins, terrequinones, terretonins and territrems. The cholesterol-lowering agent mevinolin was found in A. terreus and A. neoafricanus only. The hepatotoxic extrolite citrinin was found in eight species: A. alabamensis, A. allahabadii, A. carneus, A. floccosus, A. hortai, A. neoindicus, A. niveus and A. pseudoterreus. The neurotoxic extrolite citreoviridin was found in five species: A. neoafricanus, A. aureoterreus, A. pseudoterreus, A. terreus and A. neoniveus. Territrems, tremorgenic extrolites, were found in some strains of A. alabamensis and A. terreus.

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(+)-Geodin fromAspergillus terreus

Cited by 12 publications

References 27 publications

Methyl 8-oxo-2-phenyl-1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate

Methyl 8-oxo-2-phenyl-1-oxaspiro[4.5]deca-2,6,9-triene-3-carboxylate

Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

New species in Aspergillus section Terrei

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