Relative and absolute structure of phomolide C

Ito, Atsushi; Maeda, Hayato; Tonouchi, Akio; Hashimoto, Minoru

doi:10.1080/09168451.2015.1015953

Cited by 7 publications

(3 citation statements)

References 8 publications

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“…The phomolides are another group of closely related metabolites from Diaporthe . For instance, phomolide C exhibited inhibitory effects against the proliferation of human colon adenocarcinoma cells at a concentration of 50 µg/mL ( 34 ). Xylarolide and xylarolide A, other 10-membered lactones isolated from endophytic Diaporthe spp., have shown interesting cytotoxic properties ( 35 ).…”

Section: Discussionmentioning

confidence: 99%

Metabolomics insights into the polyketide-lactones produced by Diaporthe caliensis sp. nov., an endophyte of the medicinal plant Otoba gracilipes

Charria-Girón,

Marin-Felix,

Beutling

et al. 2023

Microbiol Spectr

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Plants of the genus Otoba have been the basis for the treatment of tropical diseases in indigenous communities of countries like Colombia. Despite the lack of knowledge about their bioactive principles, endophytic fungi derived from medicinal plants are a prolific source of innovative chemistry. We systematically investigated the secondary metabolite production of a previously undescribed species of Diaporthe , herein introduced as Diaporthe caliensis sp. nov., using different metabolomics approaches together with classical chemical screening. To get an outline of the chemical space produced by this fungus, an exploratory molecular networking (MN) analysis was undertaken. A major molecular family was found to contain the known 10-membered lactone phomol ( 1 ), together with other putative congeners as compound 3 . After isolation by preparative high-performance liquid chromatography, we confirmed phomol ( 1 ) as the main reason for the antimicrobial activity of the crude extract. The unknown absolute configuration of 1 was determined by the synthesis of α-methoxy-α-trifluoromethylphenylacetyl (MTPA)-esters and chemical degradation experiments. Moreover, caliensolides A ( 2 ) and B ( 3 ) were isolated, and their structures were elucidated as novel butenolides structurally unrelated to 1 . Overall, the initial MN analysis incorrectly clustered compounds 1 and 3 within a single molecular family, despite evident differences in chemical structures and biosynthetic origin. Contrariwise, the unsupervised substructure discovery algorithm MS2LDA provided a deeper understanding of the fragmentation patterns and correctly clustered the polyketide-lactones produced by D. caliensis sp. nov. Our findings encourage the exploration of Colombian fungal diversity, which as demonstrated here could result in the discovery of new natural products. IMPORTANCE The integration of metabolomics-based approaches into the discovery pipeline has enabled improved mining and prioritization of prolific secondary metabolite producers such as endophytic fungi. However, relying on automated untargeted analysis tools might lead to misestimation of the chemical complexity harbored in these organisms. Our study emphasizes the importance of isolation and structure elucidation of the respective metabolites in addition to deep metabolome analysis for the correct interpretation of untargeted metabolomics approaches such as molecular networking. Additionally, it encourages the further exploration of endophytic fungi from traditional medicinal plants for the discovery of natural products.

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Section: Discussionmentioning

confidence: 99%

Metabolomics insights into the polyketide-lactones produced by Diaporthe caliensis sp. nov., an endophyte of the medicinal plant Otoba gracilipes

Charria-Girón,

Marin-Felix,

Beutling

et al. 2023

Microbiol Spectr

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“…Another similar chemical constituent, phomolide C, was obtained from the strain Phomopsis sp. B27 [30] and from the fungus Diaporthe sp., however it did not show antifungal activity against Cochliobolus miyabeanus [31].…”

Section: Antimicrobial Activity Of Marine Macrolidesmentioning

confidence: 99%

Marine Macrolides with Antibacterial and/or Antifungal Activity

Karpiński

2019

Marine Drugs

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Currently, the increasing resistance of microorganisms to antibiotics is a serious problem. Marine organisms are the source of thousands of substances, which also have antibacterial and antifungal effects. Among them, marine macrolides are significant. In this review, the antibacterial and/or antifungal activities of 34 groups of marine macrolides are presented. Exemplary groups are chalcomycins, curvulides, halichondramides, lobophorins, macrolactins, modiolides, scytophycins, spongistatins, or zearalanones. In the paper, 74 antibiotics or their analog sets, among which 29 with antifungal activity, 25 that are antibacterial, and 20 that are both antifungal and antibacterial are summarized. Also, 36 macrolides or their sets are produced by bacteria, 18 by fungi, ten by sponges, seven by algae, two by porifera, and one by nudibranch. Moreover, the chemical structures of representatives from each of the 34 groups of these antibiotics are presented. To summarize, marine organisms are rich in natural macrolides. Some of these may be used in the future in the treatment of bacterial and fungal infections. Marine macrolides can also be potential drugs applicable against pathogens resistant to currently known antibiotics.

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“…on Aucuba japonica var. borealis inhibited the proliferation of human colon adenocarcinoma cells at a concentration of 50 µg/mL[45]. Compound 18-des-hydroxy cytochalasin H(22) from the endophytic fungus D. phaseolorum-92C inhibited leishmanicidal activity and moderate antioxidant activity against the breast cancer cells MDA-MB-231 and MCF-7[26].…”

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confidence: 99%

Potential of Secondary Metabolites of Diaporthe Species Associated with Terrestrial and Marine Origins

Wei

Khan

Dai

et al. 2023

JoF

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Diaporthe species produce versatile secondary metabolites (SMs), including terpenoids, fatty acids, polyketides, steroids, and alkaloids. These structurally diverse SMs exhibit a wide range of biological activities, including cytotoxic, antifungal, antibacterial, antiviral, antioxidant, anti-inflammatory, and phytotoxic activities, which could be exploited in the medical, agricultural, and other modern industries. This review comprehensively covers the production and biological potencies of isolated natural products from the genus Diaporthe associated with terrestrial and marine origins. A total of 275 SMs have been summarized from terrestrial (153; 55%) and marine (110; 41%) origins during the last twelve years, and 12 (4%) compounds are common to both environments. All secondary metabolites are categorized predominantly on the basis of their bioactivities (cytotoxic, antibacterial, antifungal, and miscellaneous activity). Overall, 134 bioactive compounds were isolated from terrestrial (92; 55%) and marine (42; 34%) origins, but about half the compounds did not report any kind of activity. The antiSMASH results suggested that Diaporthe strains are capable of encoding a wide range of SMs and have tremendous biosynthetic potential for new SMs. This study will be useful for future research on drug discovery from terrestrial and marine natural products.

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Relative and absolute structure of phomolide C

Abstract: Phomolide C (1) was isolated from a fungus Diaporthe sp. being found at Shirakami mountainous area. Although only the planar structure of 1 has been known, our detailed NMR spectroscopic analysis and ECD studies revealed its both relative and absolute configuration.

Cited by 7 publications

References 8 publications

Metabolomics insights into the polyketide-lactones produced by Diaporthe caliensis sp. nov., an endophyte of the medicinal plant Otoba gracilipes

Metabolomics insights into the polyketide-lactones produced by Diaporthe caliensis sp. nov., an endophyte of the medicinal plant Otoba gracilipes

Marine Macrolides with Antibacterial and/or Antifungal Activity

Potential of Secondary Metabolites of Diaporthe Species Associated with Terrestrial and Marine Origins

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