(+)-Menthol and Its Hydroxy Derivatives, Novel Fungal Monoterpenols from the Fusicoccin-producing Fungi,<i>Phomopsis amygdali</i>F6a and Niigata 2

Sassa, Takeshi; Kenmoku, Hiromichi; Sato, Mitsuyoshi; Murayama, Tetsuya; Kato, Nobuo

doi:10.1271/bbb.67.475

Cited by 17 publications

(12 citation statements)

References 8 publications

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“…Diaporthe ( Phomopsis ) sp. is also known to produce monoterpenoids (Sassa et al, 2003; Singh et al, 2011) as we have also shown here; as well as diterpenoids (Toyomasu et al, 2008) and triterpenoids (Zhang et al, 2013). This fungal species therefore represents a rich source of terpene synthases that could potentially be characterized.…”

Section: Discussionsupporting

confidence: 81%

Genome of Diaporthe sp. provides insights into the potential inter-phylum transfer of a fungal sesquiterpenoid biosynthetic pathway

et al. 2016

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Fungi have highly active secondary metabolic pathways which enable them to produce a wealth of sesquiterpenoids that are bioactive. One example is Δ6-protoilludene, the precursor to the cytotoxic illudins, which are pharmaceutically relevant as anticancer therapeutics. To date, this valuable sesquiterpene has only been identified in members of the fungal division Basidiomycota. To explore the untapped potential of fungi belonging to the division Ascomycota in producing Δ6-protoilludene, we isolated the a fungal endophyte Diaporthe sp. BR109 and show that it produces a diversity of terpenoids including Δ6-protoilludene. Using a genome sequencing and mining approach 17 putative novel sesquiterpene synthases were identified in Diaporthe sp. BR109. A phylogenetic approach was used to predict which gene encodes Δ6-protoilludene synthase, which was then confirmed experimentally. These analyses reveal that the sesquiterpene synthase and its putative sesquiterpene scaffold modifying cytochrome P450(s) may have been acquired by inter-phylum horizontal gene transfer from Basidiomycota to Ascomycota. Bioinformatic analyses indicate that inter-phylum transfer of these minimal sequiterpenoid secondary metabolic pathways may have occurred in other fungi. This work provides insights into the evolution of fungal sesquiterpenoid secondary metabolic pathways in the production of pharmaceutically relevant bioactive natural products.

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Section: Discussionsupporting

confidence: 81%

Genome of Diaporthe sp. provides insights into the potential inter-phylum transfer of a fungal sesquiterpenoid biosynthetic pathway

et al. 2016

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“…Among the terpenes, fungi usually produce sesquiterpenes; however, recently a prized monoterpenoid, 1,8-cineole was found having been produced by several Hypoxylon/Nodulisporium species (Tomsheck et al 2010;Riyaz-Ul-Hassan et al 2013;Shaw et al 2015). There is also a previous report of isolation of menthol from a fungus, Phomopsis amygdale (Sassa et al 2003). Phomopsis species are considered the anamorphs of Diaporthe species, a teleomorphic genus in the family Valsaceae (Girlanda et al 2002).…”

Section: Discussionmentioning

confidence: 99%

An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds

Qadri

Deshidi

Shah

et al. 2015

World J Microbiol Biotechnol

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An endophytic fungus, PR4 was found in nature associated with the rhizome of Picrorhiza kurroa, a high altitude medicinal plant of Kashmir Himalayas. The fungus was found to inhibit the growth of several phyto-pathogens by virtue of its volatile organic compounds (VOCs). Molecular phylogeny, based on its ITS1-5.8S-ITS2 ribosomal gene sequence, revealed the identity of the fungus as Phomopsis/Diaporthe sp. This endophyte was found to produce a unique array of VOCs, particularly, menthol, phenylethyl alcohol, (+)-isomenthol, β-phellandrene, β-bisabolene, limonene, 3-pentanone and 1-pentanol. The purification of compounds from the culture broth of PR4 led to the isolation of 3-hydroxypropionic acid (3-HPA) as a major metabolite. This is the first report of a fungal culture producing a combination of biologically and industrially important metabolites—menthol, phenylethyl alcohol, and 3-HPA. The investigation into the monoterpene biosynthetic pathway of PR4 led to the partial characterization of isopiperitenone reductase (ipr) gene, which seems to be significantly distinct from the plant homologue. The biosynthesis of plant-like-metabolites, such as menthol, is of significant academic and industrial significance. This study indicates that PR4 is a potential candidate for upscaling of menthol, phenylethyl alcohol, and 3-HPA, as well as for understanding the menthol/monoterpene biosynthetic pathway in fungi.

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“…The phytochemical study on the EtOAc extract of the fungi Phomopsis phyllanthicola A658 and Cytospora rhizophorae A761 resulted in the isolation of the twelve known compounds (Figure 1), including four octaketides—cytosporone B ( 1 ) [10], cytosporone M ( 2 ) [24], dothiorelone A ( 3 ), and dothiorelone B ( 4 ) [25]; three aromatic compounds—4-hydroxybenzaldehyde ( 5 ) [26], 2-p-acetoxyphenylethanol ( 6 ) [27], and 3-phenylpropane-1,2-diol ( 7 ) [28]; two monoterpenes,—(–)-(1 R ,2 R ,3 S ,4 R )-p-menthane-1,2,3-triol ( 8 ) [29] and (3 R ,4a R ,5 S ,6 R )-6-hydroxyl-5-methylramulosin ( 9 ) [30]; and three polyketides—nectriapyrone A ( 10 ) [31], phomopyronol ( 11 ) [28], and nectriapyrone D ( 12 ) [32].…”

Section: Resultsmentioning

confidence: 99%

Cytosporone B as a Biological Preservative: Purification, Fungicidal Activity and Mechanism of Action against Geotrichum citri-aurantii

et al. 2019

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To prevent citrus decay caused by Geotrichum citri-aurantii, 12 natural products were isolated from two endophytic fungi, in which cytosporone B was shown to have excellent bioactivity for control of G. citri-aurantii with median effect concentration (EC50) of 26.11 μg/mL and minimum inhibitory concentration (MIC) of 105 μg/mL, and also significantly reduced the decay of sugar orange during the in vivo trials. In addition, cytosporone B could alter the morphology of G. citri-aurantii by causing distortion of the mycelia and loss of membrane integrity. Differentially expressed genes (DEGs) between cytosporone B-treated and -untreated samples were revealed by Illumina sequencing, including 3540 unigenes. Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) analyses showed that most DEGs were related to metabolic production and cell membrane. These findings suggest cytosporone B is a promising biological preservative to control citrus decay and reveal the action mechanism of cytosporone B in relation to the destruction of the fungal cell membrane at both morphological and molecular levels.

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(+)-Menthol and Its Hydroxy Derivatives, Novel Fungal Monoterpenols from the Fusicoccin-producing Fungi,Phomopsis amygdaliF6a and Niigata 2

Cited by 17 publications

References 8 publications

Genome of Diaporthe sp. provides insights into the potential inter-phylum transfer of a fungal sesquiterpenoid biosynthetic pathway

Genome of Diaporthe sp. provides insights into the potential inter-phylum transfer of a fungal sesquiterpenoid biosynthetic pathway

An endophyte of Picrorhiza kurroa Royle ex. Benth, producing menthol, phenylethyl alcohol and 3-hydroxypropionic acid, and other volatile organic compounds

Cytosporone B as a Biological Preservative: Purification, Fungicidal Activity and Mechanism of Action against Geotrichum citri-aurantii

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