Xylarichalasin A, a Halogenated Hexacyclic Cytochalasan from the Fungus <i>Xylaria</i> cf. <i>curta</i>

Wang, Wen‐Xuan; Lei, Xinxiang; Yang, Yi-Yan; Li, Zhenghui; Ai, Hong-Lian; Li, Jing; Feng, Tao; Liu, Ji‐Kai

doi:10.1021/acs.orglett.9b02552

Cited by 46 publications

(18 citation statements)

References 26 publications

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“…Among those, the curtachalasins (e.g. 9-10) as well as xylarichalasin A (11) have to be highlighted due to their unprecedented core structures: the former harbor a tetracyclic backbone [26,27], while in the latter, a highly complex hexacyclic structure was found [28]. Curtachalasins A (9) and B were found devoid of promising bioactivities in initial screenings for cytotoxicity and antimicrobial activities [27], indicating that they do not act on the actin system like other members of the class.…”

Section: Cytochalasans From Xylariaceae (Fig 3)mentioning

confidence: 99%

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Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Becker

Stadler

2020

J Antibiot

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The families Xylariaceae and Hypoxylaceae (Xylariales, Ascomycota) represent one of the most prolific lineages of secondary metabolite producers. Like many other fungal taxa, they exhibit their highest diversity in the tropics. The stromata as well as the mycelial cultures of these fungi (the latter of which are frequently being isolated as endophytes of seed plants) have given rise to the discovery of many unprecedented secondary metabolites. Some of those served as lead compounds for development of pharmaceuticals and agrochemicals. Recently, the endophytic Xylariales have also come in the focus of biological control, since some of their species show strong antagonistic effects against fungal and other pathogens. New compounds, including volatiles as well as nonvolatiles, are steadily being discovered from these ascomycetes, and polythetic taxonomy now allows for elucidation of the life cycle of the endophytes for the first time. Moreover, recently high-quality genome sequences of some strains have become available, which facilitates phylogenomic studies as well as the elucidation of the biosynthetic gene clusters (BGC) as a starting point for synthetic biotechnology approaches. In this review, we summarize recent findings, focusing on the publications of the past 3 years.

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Section: Cytochalasans From Xylariaceae (Fig 3)mentioning

confidence: 99%

“…also afforded a novel cyclic pentapeptide as well as an unprecedented cytochalasin [35]. The cyclic pentapeptide pentaminolarin (28) showed weak inhibition against HT29 and HCT116 cell lines (IC 50 32 and 38 µM).…”

Section: Non-ribosomal Peptides From Xylariaceae (Fig 5)mentioning

confidence: 99%

Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Becker

Stadler

2020

J Antibiot

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“…[14] Relying on the intramolecular non-covalent interactions,this bottom-up approach evades the challenging synthesis for polymers.Inthis respect, oligopeptides have been considered as promising candidates because of their structural diversity and strong tendencytoform self-assemblies in solution. In our previous study,w ep roposed two types of oligopeptides as aligning media that are compatible with D 2 O [15] and CD 3 OD, [16] respectively.N otably,u sing AAKLVFF as alignment medium, the relative configuration of as eries of challenging novel natural products including spiroepicoccin A, [17] sarcomililate A, [18] xylarichalasin A, [19] herpotrichones Aa nd B, [20] polyoxygenated sesquiterpenoid, [21] and curtachalasins [22] have been elucidated based on the RDC and residual chemical-shift anisotropy (RCSA) analysis.D espite these encouraging results,s ome challenges still exist. First, until now,t here has been no DMSO-bearing medium based on molecular self-assembly.S econd, the formation of selfassembly in organic solvents usually takes several hours or even days to complete.Third, residual background signals and broad linewidths frequently hinder an accurate measurement of the dipolar couplings.F inally,d espite the feasible solidphase peptide-synthesis (SPPS) technique,t he time-consuming peptide-purification step quite often prohibits the largescale production of peptide-based media.…”

Section: Introductionmentioning

confidence: 99%

Measurement of Residual Dipolar Couplings of Organic Molecules in Multiple Solvent Systems Using a Liquid‐Crystalline‐Based Medium

et al. 2020

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Residual dipolar coupling (RDC), a robust anisotropic NMR parameter for structural elucidation of organic molecules, is only accessible in an anisotropic environment. Herein, we introduce a novel alignment medium based on the molecular self‐assembly of oligopeptide amphiphile (OPA). This medium is compatible with different intermediate and polar solvent systems, such as CD3OD, [D6]DMSO, and D2O. The preparation of the OPA‐based medium is simple and rapid, while only very weak background signals were observed from OPAs. Furthermore, we show that the purity of OPA has only a minor influence on the quality of the RDC data. These advantages allow RDC measurements of organic molecules with different polarities and solubilities with high efficiency and accuracy.

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“…Compound 17, isolated from Xylaria cf. curta , showed cytotoxicity against SMMC-7721 and MCF-7 cell lines better than that of the drug cisplatin [ 24 ]. The novel chamiside A ( 18 ) presented a novel 6/6/5 fused tricyclic core skeleton bearing a benzene ring and a rare seven-member lactone; it was isolated from Chaetomium nigricolor and exhibited antibacterial activity against S. aureus [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Ortega

Torres-Mendoza

et al. 2021

JoF

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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.

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Xylarichalasin A, a Halogenated Hexacyclic Cytochalasan from the Fungus Xylaria cf. curta

Cited by 46 publications

References 26 publications

Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Recent progress in biodiversity research on the Xylariales and their secondary metabolism

Measurement of Residual Dipolar Couplings of Organic Molecules in Multiple Solvent Systems Using a Liquid‐Crystalline‐Based Medium

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

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