New chlorinated xanthone and anthraquinone produced by a mangrove-derived fungus Penicillium citrinum HL-5126

He, Ke-Yao; Zhang, Cheng; Duan, Yi-Ru; Huang, Guo-Lei; Yang, Chenxi; Lu, Xing-Rui; Zheng, Cai‐Juan; Chen, Guang‐Ying

doi:10.1038/ja.2017.52

Cited by 45 publications

(20 citation statements)

References 21 publications

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“…However, we cannot exclude a possibility that this metabolite might be also produced by other members of the Pleosporales of which we identified a broad diversity using DNA sequencing . Nine metabolites (3‐nitropropionic acid, asperglaucide, chlorocitreorosein, citreorosein, emodin, linamarin, lotaustralin, physcion and tryptophol) could be derived from plants and fungi . Usnic acid and physcion are produced by lichen, a composite organism consisting of a symbiosis between a fungus and an algae or cyanobacterium.…”

Section: Discussionmentioning

confidence: 99%

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

et al. 2018

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Recent developments in molecular and chemical methods have enabled the analysis of fungal DNA and secondary metabolites, often produced during fungal growth, in environmental samples. We compared 3 fungal analytical methods by analysing floor dust samples collected from an office building for fungi using viable culture, internal transcribed spacer (ITS) sequencing and secondary metabolites using liquid chromatography-tandem mass spectrometry. Of the 32 metabolites identified, 29 had a potential link to fungi with levels ranging from 0.04 (minimum for alternariol monomethylether) to 5700 ng/g (maximum for neoechinulin A). The number of fungal metabolites quantified per sample ranged from 8 to 16 (average = 13/sample). We identified 216 fungal operational taxonomic units (OTUs) with the number per sample ranging from 6 to 29 (average = 18/sample). We identified 37 fungal species using culture, and the number per sample ranged from 2 to 13 (average = 8/sample). Agreement in identification between ITS sequencing and culturing was weak (kappa = -0.12 to 0.27). The number of cultured fungal species poorly correlated with OTUs, which did not correlate with the number of metabolites. These suggest that using multiple measurement methods may provide an improved understanding of fungal exposures in indoor environments and that secondary metabolites may be considered as an additional source of exposure.

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Section: Discussionmentioning

confidence: 99%

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

et al. 2018

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“…For example, penicillixanthone isolated from a marine-derived fungus Aspergillus terreus from the gorgonian coral Echinogorgia aurantiaca exhibited potent antifouling activity against larvae of the barnacle Balanus amphitrite [ 8 ]. Two other chlorinated metabolites, 4-chloro-1-hydroxy-3-methoxy-6-methyl-8-methoxycarbonyl-xanthen-9-one and chloroisosulochrin dehydrate were isolated from the extract of the endophytic fungus Penicillium citrinum HL-5126 from the mangrove Bruguiera sexangula ; however, these revealed low antibacterial activity with MIC values of 50 μM [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Lichen Xanthones as Models for New Antifungal Agents

et al. 2018

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Due to the emergence of multidrug-resistant pathogenic microorganisms, the search for new antimicrobial compounds plays an important role in current medicinal chemistry research. Inspired by lichen antimicrobial xanthones, a series of novel chlorinated xanthones was prepared using five chlorination methods (Methods A–E) to obtain different patterns of substitution in the xanthone scaffold. All the synthesized compounds were evaluated for their antimicrobial activity. Among them, 3-chloro-4,6-dimethoxy-1-methyl-9H-xanthen-9-one 15 showed promising antibacterial activity against E. faecalis (ATCC 29212 and 29213) and S. aureus ATCC 29213. 2,7-Dichloro-3,4,6-trimethoxy-1-methyl-9H-xanthen-9-one 18 revealed a potent fungistatic and fungicidal activity against dermatophytes clinical strains (T. rubrum, M. canis, and E. floccosum (MIC = 4–8 µg/mL)). Moreover, when evaluated for its synergistic effect for T. rubrum, compound 18 exhibited synergy with fluconazole (ΣFIC = 0.289). These results disclosed new hit xanthones for both antibacterial and antifungal activity.

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“… Moreover, xanthone structures have recently been identified as lichen or fungal metabolites. In the plant kingdom, 24 families have been reported so far to contain xanthones, while extensive studies on xanthone chemistry were made, e.g ., in the Clusiaceae , Gentianaceae , Guttiferae and Hypericaceae families, etc . Because of interesting biological and pharmacological features, such as antioxidant, antimicrobial, antiviral, cytotoxic, anticancer, anti‐inflammatory, hepatoprotective and MAO inhibitor activities, etc ., this compound class is attracting growing attention.…”

Section: Introductionmentioning

confidence: 99%

Structure Elucidation of the Main Tetrahydroxyxanthones of Hypericum Seeds and Investigations into the Testa Structure

Lorenz

Heller

Bunse

et al. 2018

Chemistry & Biodiversity

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Seeds from Hypericum species have recently been identified as an interesting source of xanthone derivatives. Extraction of seeds from H. perforatum with MeOH and subsequent concentration via polyamide adsorption yielded a fraction enriched in tetrahydroxyxanthones (THX), which were further semipurified by silica gel chromatography. Based on tentative structure assignment of the two main THX X1 and X2 by NMR a total synthesis was performed for both compounds (THX 1 and 2, respectively), starting with an Ullmann ether synthesis. The synthesized 1 and 2 were characterized via 1D- and 2D-NMR methods as well as by LC/HR-MS analysis and proven to be 1,4,6,7-THX (1) and 1,2,6,7-THX (2). Final structure assignment of the natural Hypericum THX constituents was accomplished by comparing chromatographic and spectroscopic data (LC/MS and GC/MS) with those of 1 and 2 which were obtained by synthesis. Beyond, investigations into the seeds of H. perforatum and H. tetrapterum by scanning electron microscopy (SEM) provided insights of the structure of the testa (seed coat), which is established by two cell layers, with the lignified sclerenchyma presumably being the depository of the xanthones.

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New chlorinated xanthone and anthraquinone produced by a mangrove-derived fungus Penicillium citrinum HL-5126

Cited by 45 publications

References 21 publications

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

Lichen Xanthones as Models for New Antifungal Agents

Structure Elucidation of the Main Tetrahydroxyxanthones of Hypericum Seeds and Investigations into the Testa Structure

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