Pyrone derivatives from the marine-derived fungus Nigrospora sp. PSU-F18

Trisuwan, Kongkiat; Rukachaisirikul, Vatcharin; Sukpondma, Yaowapa; Preedanon, Sita; Phongpaichit, Souwalak; Sakayaroj, Jariya

doi:10.1016/j.phytochem.2009.01.008

Cited by 54 publications

(37 citation statements)

References 16 publications

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“…solani have been identified from distant fungal species (19)(20)(21). Considering the structural diversity of solanapyrone analogs, additional genes may be involved in their production in other solanapyrone-producing fungi.…”

Section: Discussionmentioning

confidence: 99%

“…Solanapyrones are polyketide-derived SMs that were originally found in the plant-pathogenic fungi Alternaria solani and Ascochyta rabiei (17,18), as well as in some other ascomycetous fungi occupying different ecological niches (19)(20)(21). The fact that solanapyrones are produced by distantly related species like Nigrospora (Sordariomycetes) but not by closely related species of Ascochyta or Alternaria (Dothideomycetes) suggests the acquisition of the entire gene cluster by horizontal gene transfer (HGT) events.…”

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A Novel Type Pathway-Specific Regulator and Dynamic Genome Environments of a Solanapyrone Biosynthesis Gene Cluster in the Fungus Ascochyta rabiei

et al. 2015

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c Secondary metabolite genes are often clustered together and situated in particular genomic regions, like the subtelomere, that can facilitate niche adaptation in fungi. Solanapyrones are toxic secondary metabolites produced by fungi occupying different ecological niches. Full-genome sequencing of the ascomycete Ascochyta rabiei revealed a solanapyrone biosynthesis gene cluster embedded in an AT-rich region proximal to a telomere end and surrounded by Tc1/Mariner-type transposable elements. The highly AT-rich environment of the solanapyrone cluster is likely the product of repeat-induced point mutations. Several secondary metabolism-related genes were found in the flanking regions of the solanapyrone cluster. Although the solanapyrone cluster appears to be resistant to repeat-induced point mutations, a P450 monooxygenase gene adjacent to the cluster has been degraded by such mutations. Among the six solanapyrone cluster genes (sol1 to sol6), sol4 encodes a novel type of Zn(II)2Cys6 zinc cluster transcription factor. Deletion of sol4 resulted in the complete loss of solanapyrone production but did not compromise growth, sporulation, or virulence. Gene expression studies with the sol4 deletion and sol4-overexpressing mutants delimited the boundaries of the solanapyrone gene cluster and revealed that sol4 is likely a specific regulator of solanapyrone biosynthesis and appears to be necessary and sufficient for induction of the solanapyrone cluster genes. Despite the dynamic surrounding genomic regions, the solanapyrone gene cluster has maintained its integrity, suggesting important roles of solanapyrones in fungal biology.T he subtelomere, the region upstream of the telomere on a linear chromosome, is characterized by richness in repetitive sequences and frequent chromosomal rearrangement and lacks synteny among closely related species and even within the same species in fungi (1-4). Subtelomeric regions are also enriched with duplicate, translocated, and horizontally transferred genes and thought to be evolutionarily labile and important for niche adaptation (2, 5, 6). These plastic chromosomal regions often include contingency genes, such as genes involved in membrane transport (2, 6), nutrient assimilation (2, 7), anaerobiosis (8), and virulence (1, 9, 10). Secondary metabolite (SM) gene clusters also exhibit a subtelomeric bias (11)(12)(13)(14).In fungi, SMs play diverse roles in host and niche specialization, serving as virulence factors, antibiotics, and metal ionchelating agents (15, 16). Solanapyrones are polyketide-derived SMs that were originally found in the plant-pathogenic fungi Alternaria solani and Ascochyta rabiei (17, 18), as well as in some other ascomycetous fungi occupying different ecological niches (19-21). The fact that solanapyrones are produced by distantly related species like Nigrospora (Sordariomycetes) but not by closely related species of Ascochyta or Alternaria (Dothideomycetes) suggests the acquisition of the entire gene cluster by horizontal gene transfer (HGT) events. Recently, th...

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

A Novel Type Pathway-Specific Regulator and Dynamic Genome Environments of a Solanapyrone Biosynthesis Gene Cluster in the Fungus Ascochyta rabiei

et al. 2015

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“…It has been isolated previously from several species of the fungal genera Nigrospora (Fukushima et al 1998;Trisuwan et al 2009;Wu et al2009), Xylaria (Jimenéz-Romero et al 2008, Aspergillus (Komai et al 2003), Verticillium (Khambay et al 2000), Drechslera (Krivobok et al 1994), Hirsutella (entomopathogenic) ( K r a s n o f f a n d G u p t a 1 9 9 4 ) , P a e c i l o m y c e s (entomopathogenic) (Wu et al 2012), and Phoma (Yamamoto et al 1970). Phomolactone has antifungal activity against Aspergillus fumigatus (Komai et al 2003), nematocidal activity (Khambay et al 2000), immunomodulating activity (Krivobok et al 1994), insecticide activity (Krasnoff and Gupta 1994), phytotoxic activity (Fukushima et al 1998), and weak activity against Plasmodium falciparum (Jimenéz-Romero et al 2008).…”

Section: Resultsmentioning

confidence: 99%

Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves

et al. 2015

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Zinnia elegans Jacq. plants are infected by a fungus that causes dark red spots with necrosis on leaves, particularly in late spring to the middle of summer in the Mid-South of the United States. This fungal disease causes the leaves to wilt and eventually kills the plant. The fungus was isolated, cultured in potato dextrose broth, and identified as Nigrospora sphaerica by molecular techniques. Two major lactone metabolites (phomalactone and catenioblin A) were isolated from liquid culture of N. sphaerica isolated from Z. elegans. When injected into leaves of Z. elegans, phomalactone caused lesions similar to those of the fungus. The lesion sizes were proportional to the concentration of the phomalactone. Phomalactone, but not catenioblin A, was phytotoxic to Z. elegans and other plant species by inhibition of seedling growth and by causing electrolyte leakage from photosynthetic tissues of both Z. elegans leaves and cucumber cotyledons. This latter effect may be related to the wilting caused by the fungus in mature Z. elegans plants. Phomalactone was moderately fungicidal to Coletotrichum fragariae and two Phomopsis species, indicating that the compound may keep certain other fungi from encroaching into plant tissue that N. sphaerica has infected. Production of large amounts of phomalactone by N. sphaerica contributes to the pathogenic behavior of this fungus, and may have other ecological functions in the interaction of N. sphaerica with other fungi. This is the first report of isolation of catenioblin A from a plant pathogenic fungus. The function of catenioblin A is unclear, as it was neither significantly phyto- nor fungitoxic.

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“…We have recently identified metabolites from two sea fan-derived fungi, Nigrospora sp. PSU-F5 (Trisuwan et al, 2008), which contained epxydon and pyrone analogues, and PSU-F18 (Trisuwan et al, 2009), which contained pyrone derivatives of the solanapyrone type. We report herein the isolation of two new cyclohexene metabolites (1 and 2) along with one known phenol, tyrosol (3) (Trisuwan et al, 2009), from the fungus Nigrospora sp.…”

Section: Introductionmentioning

confidence: 99%

Cyclohexene, diketopiperazine, lactone and phenol derivatives from the sea fan-derived fungi Nigrospora sp. PSU-F11 and PSU-F12

et al. 2010

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Nigrosporanenes A (1) and B (2), two new cylohexene derivatives, and tyrosol (3) were isolated from the sea fan-derived fungus Nigrospora sp. PSU-F11, whereas five known compounds: 4-hydroxybenzoic acid (4), aplysiopsene D (5), 3-isochromanone (6), (-)-drimenin (7) and diketopiperazine derivative (8), were obtained from the fungus Nigrospora sp. PSU-F12. Their structures were established by spectroscopic evidence. We also tested their cytotoxic (on African green monkey kidney fibroblast and breast cancer cells), antioxidant (in the DPPH assay), and antibacterial (against the standard Staphylococcus aureus ATCC 25923 and methicillinresistant S. aureus) activities.

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Pyrone derivatives from the marine-derived fungus Nigrospora sp. PSU-F18

Cited by 54 publications

References 16 publications

A Novel Type Pathway-Specific Regulator and Dynamic Genome Environments of a Solanapyrone Biosynthesis Gene Cluster in the Fungus Ascochyta rabiei

A Novel Type Pathway-Specific Regulator and Dynamic Genome Environments of a Solanapyrone Biosynthesis Gene Cluster in the Fungus Ascochyta rabiei

Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves

Cyclohexene, diketopiperazine, lactone and phenol derivatives from the sea fan-derived fungi Nigrospora sp. PSU-F11 and PSU-F12

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