Notizen: 5-Deoxybostrycoidin, a New Metabolite Produced by the Fungus Nectria haematococca (Berk. and Br.) Wr.

Parisot, Denise; Devys, Michel; Barbier, Michel

doi:10.1515/znb-1989-1125

Cited by 28 publications

(26 citation statements)

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“…The elucidation of ( 5 ) was aided by the observed similarity between 1 H and 13 C shifts of ( 1 ) and ( 5 ) ( Table S5 ) and those reported for bostrycoidin 19 . Especially, the chemical shift values in the nitrogen containing ring were directly comparable.…”

Section: Resultsmentioning

confidence: 93%

Black perithecial pigmentation in Fusarium species is due to the accumulation of 5-deoxybostrycoidin-based melanin

Frandsen

Rasmussen

Knudsen

et al. 2016

Sci Rep

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Biosynthesis of the black perithecial pigment in the filamentous fungus Fusarium graminearum is dependent on the polyketide synthase PGL1 (oPKS3). A seven-membered PGL1 gene cluster was identified by over-expression of the cluster specific transcription factor pglR. Targeted gene replacement showed that PGL1, pglJ, pglM and pglV were essential for the production of the perithecial pigment. Over-expression of PGL1 resulted in the production of 6-O-demethyl-5-deoxybostrycoidin (1), 5-deoxybostrycoidin (2), and three novel compounds 5-deoxybostrycoidin anthrone (3), 6-O-demethyl-5-deoxybostrycoidin anthrone (4) and purpurfusarin (5). The novel dimeric bostrycoidin purpurfusarin (5) was found to inhibit the growth of Candida albicans with an IC50 of 8.0 +/− 1.9 μM. The results show that Fusarium species with black perithecia have a previously undescribed form of 5-deoxybostrycoidin based melanin in their fruiting bodies.

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Section: Resultsmentioning

confidence: 93%

Black perithecial pigmentation in Fusarium species is due to the accumulation of 5-deoxybostrycoidin-based melanin

Frandsen

Rasmussen

Knudsen

et al. 2016

Sci Rep

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show abstract

“…The black perithecial pigment, sometimes described as dark blue, violet, or purple [ 28 , 92 ], is almost restricted to the fruiting body [ 93 ], though the producing gene is even present in Fusarium species with an unknown teleomorph [ 23 ]. The pigment’s nature is still under study and only recently has been related to fusorubins [ 94 ] and described as ″5-deoxybostrycoidin-based melanin″ [ 28 ], with C 15 H 11 NO 4 as the molecular formula [ 95 ] ( Figure 6 ).…”

Section: Major F Graminearum Pigmentsmentioning

confidence: 99%

“…Several Fusarium species, including F. graminearum , F. verticillioides , and F. fujikuroi [ 28 , 94 ], produce the blackish perithecial pigments, and appear to be related to an ancestral highly conserved gene cluster [ 96 ]. The fungus Nectria haematococca also showed the ability to produce 5-deoxybostrycoidin [ 95 ]. In F. graminearum , the six-gene PGL cluster, particularly the gene PGL1 or PKS3 , seems to be associated with the production of the polyketide synthase responsible for biosynthesis of the black perithecial pigment [ 37 , 97 ].…”

Section: Major F Graminearum Pigmentsmentioning

confidence: 99%

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

Cambaza

2018

Foods

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Several studies have explored in depth the biochemistry and genetics of the pigments present in Fusarium graminearum, but there is a need to discuss their relationship with the mold’s observable surface color pattern variation throughout its lifecycle. Furthermore, they require basic cataloguing, including a description of their major features known so far. Colors are a viable alternative to size measurement in growth studies. When grown on yeast extract agar (YEA) at 25 °C, F. graminearum initially exhibits a whitish mycelium, developing into a yellow-orange mold by the sixth day and then turning into wine-red. The colors are likely due to accumulation of the golden yellow polyketide aurofusarin and the red rubrofusarin, but the carotenoid neurosporaxanthin also possibly plays a major role in the yellow or orange coloration. Torulene might contribute to red tones, but it perhaps ends up being converted into neurosporaxanthin. Culmorin is also present, but it does not contribute to the color, though it was initially isolated in pigment studies. Additionally, there is the 5-deoxybostrycoidin-based melanin, but it mostly occurs in the teleomorph’s perithecium. There is still a need to chemically quantify the pigments throughout the lifecycle, and analyze their relationships and how much each impacts F. graminearum’s surface color.

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“…The black perithecial pigment, sometimes described as dark blue, violet, or purple [28,92], is almost restricted to the fruiting body [93], though the producing gene is even present in Fusarium species with an unknown teleomorph [23]. The pigment's nature is still under study and only recently has been related to fusorubins [94] and described as "5-deoxybostrycoidin-based melanin" [28], with C 15 H 11 NO 4 as the molecular formula [95] (Figure 6). Several Fusarium species, including F. graminearum, F. verticillioides, and F. fujikuroi [28,94], produce the blackish perithecial pigments, and appear to be related to an ancestral highly conserved gene cluster [96].…”

Section: Black Perithecial Pigmentmentioning

confidence: 99%

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

Cambaza

2018

Preprint

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Several studies explore in depth the biochemistry and genetics of the pigments present in Fusarium graminearum but there is a need to discuss about their relationship with the mold’s observable surface color pattern variation throughout its lifecycle. Furthermore, they require basic cataloguing and description of their major features known so far. Colors are a viable alternative to size measurement in growth studies. When grown on yeast extract agar (YEA) at 25 °C, F. graminearum initially exhibits a whitish mycelium, developing into a yellow-orange mold by the sixth day and then turning into wine-red. The colors are likely due to accumulation of the golden yellow polyketide aurofusarin and the red rubrofusarin, but the carotenoid neurosporaxanthin possibly play also a major role in the yellow or orange coloration. Torulene might contribute for red tones but it perhaps ends up being converted into neurosporaxanthin. Culmorin is also present but it does not contribute for the color, though it was initially isolated in pigment studies, and there is the 5-deoxybostrycoidin-based melanin, but it occurs mostly in the teleomorph’s perithecium. There is still a need to chemically quantify the pigments throughout the lifecycle, analyze their relationships and how much each impacts F. graminearum surface color.

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Notizen: 5-Deoxybostrycoidin, a New Metabolite Produced by the Fungus Nectria haematococca (Berk. and Br.) Wr.

Abstract: The structure 2 is established for 5-deoxybostrycoidin, a new metabolite isolated from cultures of the fungus Nectria haematococca (Berk. and Br.) Wr., on the basis of physico-chemical data (MS, 1H and 13C NMR, acetylation) and by reference to the known bostrycoidin 1.

Cited by 28 publications

References 0 publications

Black perithecial pigmentation in Fusarium species is due to the accumulation of 5-deoxybostrycoidin-based melanin

Black perithecial pigmentation in Fusarium species is due to the accumulation of 5-deoxybostrycoidin-based melanin

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

Comprehensive Description of Fusarium graminearum Pigments and Related Compounds

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