Dihydroisocoumarines et acide mycophenolique du milieu de culture du champignon phytopathogene septoria nodorum

Devys, Michel; Bousquet, Jean-Francois; Kollmann, Albert; Barbier, Michel

doi:10.1016/s0031-9422(00)82234-7

Cited by 56 publications

(34 citation statements)

References 6 publications

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“…17 This secondary metabolite was previously isolated from several fungi species, including L. theobromae. 10 The molecular formula of compound 3, C 23 H 32 O 4 , was suggested by 1 H and 13 C NMR.…”

Section: Resultsmentioning

confidence: 99%

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

Nunes¹,

Oliveira²,

Arriaga³

et al. 2008

J. Braz. Chem. Soc.

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O fungo fitopatogênico Lasiodiplodia theobromae, isolado de goiaba, foi cultivado em arroz por 32 dias à temperatura ambiente. Extração com CH 2 Cl 2 :MeOH (3:7), seguido de fracionamento cromatográfico do extrato forneceu o esteróide ergosterol. Da cultura fúngica em meio de Czapeck por 40 dias à temperatura ambiente, foram isolados a isocumarina cis-4-hidroximeleína e um sesquiterpeno do tipo eremofilano. O sesquiterpeno eremofilano está sendo descrito pela primeira vez na literatura. Este é o primeiro relato do isolamento de um sesquiterpeno eremofilano para o gênero Lasiodiplodia.The phytopatogenic fungus Lasiodiplodia theobromae, isolated from guava, was cultivated in rice for 32 days at room temperature. Extraction with CH 2 Cl 2 :MeOH (3:7), followed by chromatography fractionation of the extract provided ergosterol. From the fungus culture in Czapeck medium for 40 days at room temperature, were isolated isocoumarin cis-4-hydroxymeleine and an eremophilane-type sesquiterpene. The latter compound is being reported for the first time in the literature. Also, this is the first time that an eremophilane sesquiterpene is described for Lasiodiplodia genus.

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Section: Resultsmentioning

confidence: 99%

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

Nunes¹,

Oliveira²,

Arriaga³

et al. 2008

J. Braz. Chem. Soc.

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“…For production of compounds, P. nodorum SN15 was grown in modified Fries liquid medium as described previously (8,16). Briefly, about 10 8 spores were inoculated in six 2-liter flasks containing 500 ml liquid medium and in-cubated at 22°C for 48 h with shaking, followed by stationary incubation in the dark at 22°C for another 2 weeks.…”

Section: Methodsmentioning

confidence: 99%

“…So far, none of the products of these secondary metabolite gene clusters have been identified, and only a few secondary metabolites have been identified in this species (7). These metabolites include (R)-mellein and derivatives (8,9), septorines (10,11), mycophenolic acid (8), alternariol (12), and (ϩ)-4=-methoxy-(2S)-methylbutyrophenone (13).…”

mentioning

confidence: 99%

An In Planta -Expressed Polyketide Synthase Produces ( R )-Mellein in the Wheat Pathogen Parastagonospora nodorum

Chooi

Krill

Barrow

et al. 2015

Appl Environ Microbiol

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dParastagonospora nodorum is a pathogen of wheat that affects yields globally. Previous transcriptional analysis identified a partially reducing polyketide synthase (PR-PKS) gene, SNOG_00477 (SN477), in P. nodorum that is highly upregulated during infection of wheat leaves. Disruption of the corresponding SN477 gene resulted in the loss of production of two compounds, which we identified as (R)-mellein and (R)-O-methylmellein. Using a Saccharomyces cerevisiae yeast heterologous expression system, we successfully demonstrated that SN477 is the only enzyme required for the production of (R)-mellein. This is the first identification of a fungal PKS that is responsible for the synthesis of (R)-mellein. The P. nodorum ⌬SN477 mutant did not show any significant difference from the wild-type strain in its virulence against wheat. However, (R)-mellein at 200 g/ml inhibited the germination of wheat (Triticum aestivum) and barrel medic (Medicago truncatula) seeds. Comparative sequence analysis identified the presence of mellein synthase (MLNS) homologues in several Dothideomycetes and two sodariomycete genera. Phylogenetic analysis suggests that the MLNSs in fungi and bacteria evolved convergently from fungal and bacterial 6-methylsalicylic acid synthases.

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“…On the 1 H NMR spectrum seven protons were observed (Table 1). Compound 2 was identified as (3R,4R)-cis-4-hydroxymellein according to data reported by Cole et al (1971) and Devys et al (1980).…”

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confidence: 94%

“…On the 1 H NMR spectrum only two AB protons were observed in the aromatic portion, appearing as a doublet at δ 6.64 and 7.10 with the same coupling constant of 8 Hz. Compound 3 was identified as (3R)-7-hydroxymellein (Devys et al 1980).…”

mentioning

confidence: 99%

Identification of phytotoxins from Botryosphaeria obtusa, a pathogen of black dead arm disease of grapevine

et al. 2009

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A bioassay-guided fractionation of a culture filtrate of Botryosphaeria obtusa led to the isolation of four dihydroisocoumarins, named mellein 1, 4-hydroxymellein 2, 7-hydroxymellein 3 and the new 4,7-dihydroxymellein 4. LC-UV-DAD-MS analysis of vine wood infected by B. obtusa revealed the presence of mellein (1). Botryosphaeria obtusa was also able to oxidise wood δ-resveratrol into the dimer delta-viniferin. The structures of isolated phytotoxins were established on the basis of IR, MS, 1D and 2D NMR.

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Dihydroisocoumarines et acide mycophenolique du milieu de culture du champignon phytopathogene septoria nodorum

Cited by 56 publications

References 6 publications

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

An In Planta -Expressed Polyketide Synthase Produces ( R )-Mellein in the Wheat Pathogen Parastagonospora nodorum

Identification of phytotoxins from Botryosphaeria obtusa, a pathogen of black dead arm disease of grapevine

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