Two pairs of enantiomeric α-pyrone dimers from the endophytic fungus Phoma sp. YN02-P-3

Sang, Xia-Nan; Chen, Shaofei; Chen, Gang; An, Xiao; Li, Sheng-Ge; Lu, Xiaojie; Zhao, Dan; Bai, Jiao; Wang, Haifeng; Pei, Yue‐Hu

doi:10.1039/c6ra26319d

Cited by 11 publications

(7 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Phomone A and B are enantiometric α-pyrone dimers isolated from the endophytic fungus Phoma sp. YN02-p-3 [81,82]. Blumeoside C, which is an iridoid glucoside isolated from Fagraea blumei [80] has the same molecular formula.…”

Section: Resultsmentioning

confidence: 99%

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

et al. 2019

View full text Add to dashboard Cite

Endophytes are microorganisms living inside plant hosts and are known to be beneficial for the host plant vitality. In this study, we isolated three endophytic fungus species from the roots of Scots pine seedlings growing on Finnish drained peatland setting. The isolated fungi belonged to dark septate endophytes (DSE). The metabolic profiles of the hot water extracts of the fungi were investigated using Ultrahigh Performance Liquid Chromatography with Diode Array Detection and Electron Spray Ionization source Mass Spectrometry with Orbitrap analyzer (UPLC–DAD–ESI–MS–Orbitrap). Out of 318 metabolites, we were able to identify 220, of which a majority was amino acids and peptides. Additionally, opine amino acids, amino acid quinones, Amadori compounds, cholines, nucleobases, nucleosides, nucleotides, siderophores, sugars, sugar alcohols and disaccharides were found, as well as other previously reported metabolites from plants or endophytes. Some differences of the metabolic profiles, regarding the amount and identity of the found metabolites, were observed even though the fungi were isolated from the same host. Many of the discovered metabolites have been described possessing biological activities and properties, which may make a favorable contribution to the host plant nutrient availability or abiotic and biotic stress tolerance.

show abstract

Section: Resultsmentioning

confidence: 99%

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

et al. 2019

View full text Add to dashboard Cite

show abstract

“…config. assignment for 500a/500b was confirmed by single-crystal X-ray diffraction analysis [241]. Compounds 501 and 502 were elucidated as C-ring open flavonoids from Pochonia chlamydosporia var.…”

Section: Nonalkaloidsmentioning

confidence: 76%

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

Capon

et al. 2022

Molecules

View full text Add to dashboard Cite

The knowledge that natural products (NPs) are potent and selective modulators of important biomacromolecules (e.g., DNA and proteins) has inspired some of the world’s most successful pharmaceuticals and agrochemicals. Notwithstanding these successes and despite a growing number of reports on naturally occurring pairs of enantiomers, this area of NP science still remains largely unexplored, consistent with the adage “If you don’t seek, you don’t find”. Statistically, a rapidly growing number of enantiomeric NPs have been reported in the last several years. The current review provides a comprehensive overview of recent records on natural enantiomers, with the aim of advancing awareness and providing a better understanding of the chemical diversity and biogenetic context, as well as the biological properties and therapeutic (drug discovery) potential, of enantiomeric NPs.

show abstract

“…A pair of enantiomers, (±)–phomone A ( 153 ) and (±)–phomone B ( 154 ), were isolated from the culture of Phoma sp., and both represent the first examples of 6-α,β-unsaturated ester-2-pyrone dimers; compound 153 also possessed a novel 6/4/5/6 tetracyclic ring system. Both compounds did not show cytotoxicity against three human cancer cells, but the acetylated product of 153 showed moderate cytotoxicity against the HL-60 cell line [ 91 ].…”

Section: Resultsmentioning

confidence: 99%

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Ortega

Torres-Mendoza

et al. 2021

JoF

View full text Add to dashboard Cite

Among microorganisms, endophytic fungi are the least studied, but they have attracted attention due to their high biological diversity and ability to produce novel and bioactive secondary metabolites to protect their host plant against biotic and abiotic stress. These compounds belong to different structural classes, such as alkaloids, peptides, terpenoids, polyketides, and steroids, which could present significant biological activities that are useful for pharmacological or medical applications. Recent reviews on endophytic fungi have mainly focused on the production of novel bioactive compounds. Here, we focus on compounds produced by endophytic fungi, reported with uncommon bioactive structures, establishing the neighbor net and diversity of endophytic fungi. The review includes compounds published from January 2015 to December 2020 that were catalogued as unprecedented, rare, uncommon, or possessing novel structural skeletons from more than 39 different genera, with Aspergillus and Penicillium being the most mentioned. They were reported as displaying cytotoxic, antitumor, antimicrobial, antiviral, or anti-inflammatory activity. The solid culture, using rice as a carbon source, was the most common medium utilized in the fermentation process when this type of compound was isolated.

show abstract

Two pairs of enantiomeric α-pyrone dimers from the endophytic fungus Phoma sp. YN02-P-3

Abstract: (±) Phomones A (1) and B (2), two pairs of novel enantiomeric α-pyrone dimers from the endophytic fungus Phoma sp. YN02-P-3 are reported.

Cited by 11 publications

References 16 publications

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

Metabolic Profiling of Water-Soluble Compounds from the Extracts of Dark Septate Endophytic Fungi (DSE) Isolated from Scots Pine (Pinus sylvestris L.) Seedlings Using UPLC–Orbitrap–MS

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Contact Info

Product

Resources

About