Cytotoxic Pentacyclic and Tetracyclic Aromatic Sesquiterpenes from <i>Phomopsis archeri</i>

Hemtasin, Chulida; Kanokmedhakul, Somdej; Kanokmedhakul, Kwanjai; Hahnvajanawong, Chariya; Soytong, Kasem; Prabpai, Samran; Kongsaeree, Palangpon

doi:10.1021/np100632g

Cited by 72 publications

(41 citation statements)

References 22 publications

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“…Furthermore, fungal endophytes such as the Ascomycete Diaporthe ( Phomopsis ) sp. produce a diversity of interesting and bioactive sesquiterpene scaffolds, such as cadinanes (Silva et al, 2006), drimanes (Zang le et al, 2012) and meroterpenoids (Hemtasin et al, 2011; Ma et al, 2015; Tajima et al, 2004) and as we have shown here, trans -humulane scaffolds. Diaporthe ( Phomopsis ) sp.…”

Section: Discussionmentioning

confidence: 64%

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: Discussionmentioning

confidence: 64%

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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“…This is because many of known species have wide host range and there are few characters that can differentiate them (Uecker 1988). Some species are thought to be host-specific; while Hemtasin et al 2011Fungal Diversity (2011 others are able to infect a wide range of hosts and therefore caution is needed when concluding diversity in various hosts (Mostert et al 2001a;Crous 2005;Schilder et al 2005;Santos and Phillips 2009;Diogo et al 2010). Phomopsis strains isolated from a single host may represent more than one taxon (Rehner and Uecker 1994).…”

Section: Significance Of Hyperdiversitymentioning

confidence: 99%

The genus Phomopsis: biology, applications, species concepts and names of common phytopathogens

et al. 2011

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The genus Phomopsis (teleomorph Diaporthe) comprises phytopathologically important microfungi with diverse host associations and a worldwide distribution. Species concepts in Phomopsis have been based historically on morphology, cultural characteristics and host affiliation. This paper serves to provide an overview of the current status of the taxonomy in Phomopsis with special reference to biology, applications of various species, species concepts, future research perspectives and names of common pathogens, the latter being given taxonomic reappraisal. Accurate species identification is critical to understanding disease epidemiology and in developing effective control measures for plant diseases. Difficulties in accurate species identification using morphology have led to the application of alternative approaches to differentiate species, including virulence and pathogenicity, biochemistry, metabolites, physiology, antagonism, molecular phylogenetics and mating experiments. Redefinition of Phomopsis/Diaporthe species has been ongoing, and some species have been redefined based on a combination of molecular, morphological, cultural, phytopathological and mating type data. Rapid progress in molecular identification has in particular revolutionized taxonomic studies, providing persuasive genetic evidence to define the species boundaries. A backbone ITS based phylogenetic tree is here in generated using the sequences derived from 46 type, epitype cultures, and vouchers and is presented as a rough and quick identification guide for species of Phomopsis. The need for epitypification of taxonomic entities and the need to use multiple loci in phylogenies that better reflect species limits are suggested. The account of names of phytopathogens currently in use are listed alphabetically and annotated with a taxonomic entry, teleomorph, associated hosts and disease symptoms, including brief summaries of taxonomic and phylogenetic research. Available type culture information and details of gene sequences derived from type cultures are also summarized and tabulated.

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“…Phomoarcherins B exhibited in vitro cytotoxic activity against KKU-100, KKU-M139, KKU-M156, KKU-M213, KKU-M214, and KB cell lines with IC 50 values of 8.0, 0.1, 2.0, 20, 5.0, and 9.4 μg/ml, respectively. Phomoarcherins C exhibited in vitro cytotoxic activity against KKU-100, KKU-M139, KKU-M156, KKU-M213, and KKU-M214 cell lines with IC 50 values 8.9, 8.9, 18.0, 15.4, and 18.8 μg/ml, respectively (Hemtasin et al 2011).…”

Section: Compounds From Endophytic Fungi Of Terrestrial Plantsmentioning

confidence: 99%

Fungal Endophytes: An Amazing and Hidden Source of Cytotoxic Compounds

Deshmukh

Verekar

2014

Microbial Diversity and Biotechnology in Food Security

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This review covers substantially the cytotoxic compounds isolated from endophytic fungi from terrestrial and mangrove plants during [2009][2010][2011][2012]. Endophytes living asymptomatically within plant tissues have been found in almost all plants studied to date. Many of the compounds reported here were originally isolated from plants, then from endophytic fungi, whereas some are exclusively isolated from endophytic fungi. The anticancer activities in this review are from the published cytotoxicity against specific cancer cell lines. Development of these natural compounds is based on their cytotoxic activity profiles, chemical structures, and potential structure-activity relationship deduced from the biochemical and cytotoxic studies.

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Cytotoxic Pentacyclic and Tetracyclic Aromatic Sesquiterpenes from Phomopsis archeri

Cited by 72 publications

References 22 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

The genus Phomopsis: biology, applications, species concepts and names of common phytopathogens

Fungal Endophytes: An Amazing and Hidden Source of Cytotoxic Compounds

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