New Anthraquinone Derivatives from <i>Geosmithia lavendula</i>

Malak, Lourin G.; Bishay, D. W.; Abdel-Baky, A.; Moharram, A. M.; Cutler, Stephen J.; Ross, Samir A.

doi:10.1177/1934578x1300800215

Cited by 7 publications

(10 citation statements)

References 11 publications

(29 reference statements)

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“…The molecular formula of Compound I was determined to be C 15 H 10 O 7, based on HR-ESI-MS (m/z 315.0503 [M+H] + ) (Figs 8C and S16 ). Analysis of the 1 H ( S17 Fig ) and 13 C NMR spectroscopic data ( S18 Fig , S6 Table ) for compound I showed that its structure was consistent with that of 1-acetyl-2,4,6,8-tetrahydroxy-9,10-anthraquinone [ 25 ], indicating that compound I was an anthraquinone derivative. As we were unable to identify a PKS2-derived SM in A .…”

Section: Resultsmentioning

confidence: 99%

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Duplication of a Pks gene cluster and subsequent functional diversification facilitate environmental adaptation in Metarhizium species

Zeng

Zhang

et al. 2018

PLoS Genet

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The ecological importance of the duplication and diversification of gene clusters that synthesize secondary metabolites in fungi remains poorly understood. Here, we demonstrated that the duplication and subsequent diversification of a gene cluster produced two polyketide synthase gene clusters in the cosmopolitan fungal genus Metarhizium. Diversification occurred in the promoter regions and the exon-intron structures of the two Pks paralogs (Pks1 and Pks2). These two Pks genes have distinct expression patterns, with Pks1 highly expressed during conidiation and Pks2 highly expressed during infection. Different upstream signaling pathways were found to regulate the two Pks genes. Pks1 is positively regulated by Hog1-MAPK, Slt2-MAPK and Mr-OPY2, while Pks2 is positively regulated by Fus3-MAPK and negatively regulated by Mr-OPY2. Pks1 and Pks2 have been subjected to positive selection and synthesize different secondary metabolites. PKS1 is involved in synthesis of an anthraquinone derivative, and contributes to conidial pigmentation, which plays an important role in fungal tolerance to UV radiation and extreme temperatures. Disruption of the Pks2 gene delayed formation of infectious structures and increased the time taken to kill insects, indicating that Pks2 contributes to pathogenesis. Thus, the duplication of a Pks gene cluster and its subsequent functional diversification has increased the adaptive flexibility of Metarhizium species.

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Section: Resultsmentioning

confidence: 99%

“…Anthraquinone derivatives have been found in the fungus G . lavendula [ 25 ]. Here we found that M .…”

Section: Discussionmentioning

confidence: 99%

Duplication of a Pks gene cluster and subsequent functional diversification facilitate environmental adaptation in Metarhizium species

Zeng

Zhang

et al. 2018

PLoS Genet

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“…The former is a compound with potential antibacterial, antibiofilm, and anti-inflammatory activities found in a sea anemone ( Stichodactyla haddoni ) [ 73 ] and sea hares ( Aplysia sp.) [ 74 ], while the latter is an antioxidant [ 75 ] that has been isolated from the fungi Geosmithia lavendulan [ 76 ]. None of the remaining aMFs listed in Table 2 have previously been reported to occur in sponges or marine samples, nor do they have any known biological function.…”

Section: Resultsmentioning

confidence: 99%

Comparative metabolomic analysis reveals shared and unique chemical interactions in sponge holobionts

et al. 2022

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Background Sponges are ancient sessile metazoans, which form with their associated microbial symbionts a complex functional unit called a holobiont. Sponges are a rich source of chemical diversity; however, there is limited knowledge of which holobiont members produce certain metabolites and how they may contribute to chemical interactions. To address this issue, we applied non-targeted liquid chromatography tandem mass spectrometry (LC-MS/MS) and gas chromatography mass spectrometry (GC-MS) to either whole sponge tissue or fractionated microbial cells from six different, co-occurring sponge species. Results Several metabolites were commonly found or enriched in whole sponge tissue, supporting the notion that sponge cells produce them. These include 2-methylbutyryl-carnitine, hexanoyl-carnitine and various carbohydrates, which may be potential food sources for microorganisms, as well as the antagonistic compounds hymenialdisine and eicosatrienoic acid methyl ester. Metabolites that were mostly observed or enriched in microbial cells include the antioxidant didodecyl 3,3′-thiodipropionate, the antagonistic compounds docosatetraenoic acid, and immune-suppressor phenylethylamide. This suggests that these compounds are mainly produced by the microbial members in the sponge holobiont, and are potentially either involved in inter-microbial competitions or in defenses against intruding organisms. Conclusions This study shows how different chemical functionality is compartmentalized between sponge hosts and their microbial symbionts and provides new insights into how chemical interactions underpin the function of sponge holobionts.

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“…langdonii and G . levendula produce bioactive compounds with antimicrobial and antileishmanial activities (Stodulkova et al ., 2010; Malaka et al ., 2013). Several species of Geosmithia can also inhibit phoretic mites (Machingambi et al ., 2014).…”

Section: Introductionmentioning

confidence: 99%

“…from Ulmus minor afflicted with Dutch elm disease in Switzerland, although their role was not described (Hänzi et al, 2016). Furthermore, G. langdonii and G. levendula produce bioactive compounds with antimicrobial and antileishmanial activities (Stodulkova et al, 2010;Malaka et al, 2013). Several species of Geosmithia can also inhibit phoretic mites (Machingambi et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Symbiosis and pathogenicity of Geosmithia and Talaromyces spp. associated with the cypress bark beetles Phloeosinus spp. and their parasitoids

Meshram

Sharma

Maymon

et al. 2022

Environmental Microbiology

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Fungi associated with cypress bark beetles are practically unknown in the Eastern Mediterranean. Our study focused on the fungi associated with the body parts and galleries of two indigenous cypress bark beetles, Phloeosinus armatus and P. bicolor, sampled from Cupressus sempervirens trees in different regions in Israel. Arbitrarily primed PCR, performed on genomic DNA of 302 isolates, clustered the fungal population into five distinct groups. Multilocus phylogeny, splitnetwork analyses and morphological characterization identified the isolates as Geosmithia omnicola, Geosmithia langdonii, Geosmithia sp. 708b, Geosmithia cupressina sp. nov. CBS147103 and Talaromyces cupressi sp. nov. CBS147104. Of these fungal isolates, G. cupressina and T. cupressi are newly described, and their morphological features and phylogenetic designations are presented. Inoculation of intact cypress saplings in an outdoor net-house revealed that only the representative isolate T. cupressi sp. nov. CBS147104 causes 100% disease incidence, whereas Geosmithia spp. isolates are not pathogenic. A number of these fungi were isolated from parasitoids that emerged from branch and stem sections colonized by P. armatus. This study suggests a long and stable association between Phloeosinus and Geosmithia species, and a possible role for additional associated fungal species as pathogens or endophytes of C. sempervirens trees in Israel.

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New Anthraquinone Derivatives from Geosmithia lavendula

Cited by 7 publications

References 11 publications

Duplication of a Pks gene cluster and subsequent functional diversification facilitate environmental adaptation in Metarhizium species

Duplication of a Pks gene cluster and subsequent functional diversification facilitate environmental adaptation in Metarhizium species

Comparative metabolomic analysis reveals shared and unique chemical interactions in sponge holobionts

Symbiosis and pathogenicity of Geosmithia and Talaromyces spp. associated with the cypress bark beetles Phloeosinus spp. and their parasitoids

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