Integrating Molecular Networking and 1H NMR To Target the Isolation of Chrysogeamides from a Library of Marine-Derived Penicillium Fungi

Hou, Xuemei; Li, Yue-Ying; Shi, Yunwei; Fang, Yiwu; Chao, Rong; Gu, Yu‐Cheng; Wang, Chang‐Yun; Shao, Chang‐Lun

doi:10.1021/acs.joc.8b02614

Cited by 52 publications

(38 citation statements)

References 35 publications

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“…Nevertheless, based on its fungal origin, we tentatively propose that the HMDA moiety in oryzamides from Nigrospora oryzae [17] and scopularides from Scopulariopsis sp. CMB-F458 [18], the homologous 3-hydroxy-4-methylhexanoic acid (HMHA) moiety in chrysogenamide D from Penicillium chrysogenum [19], and the homologous HMHDA unit of TKR2999 share all the same 3S, 4S absolute configuration for the two chiral centers of the fatty acid chain.…”

Section: Resultsmentioning

confidence: 99%

Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens

et al. 2020

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An antifungal lipodepsipeptide was obtained from cultures of the fungus Foliophoma fallens CF-236885. Its structure, elucidated by HRMS and NMR spectroscopy, contained Gly, Thr, Asn, β-Ala, Orn, Ala, two Ser residues, and 3-hydroxy-4-methylhexadecanoic acid. The absolute configuration of its amino acid residues was determined using Marfey’s analysis and J-based configuration analysis helped to establish the relative configuration of the 3-hydroxy-4-methylhexadecanoic acid moiety. A literature search retrieved a patent describing antibiotic TKR2999 (1), whose non-disclosed structure was confirmed to be identical to that found for our compound, according to its physicochemical properties and NMR spectra. Compound 1 displayed potent antifungal activity against Aspergillus fumigatus and a panel of Candida strains.

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Section: Resultsmentioning

confidence: 99%

Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens

et al. 2020

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“…41), including the new compounds 235-237 (chrysogeamides A-C) and 240-244 (hrysogeamides D-H), as well as the known compounds 238 and 239 (scopularides A and B) ( Fig. 42) (Hou et al 2019b). These cyclohexadepsipeptides contain the same D-Leu fragment, and 235 and 242 are reported for the first time featuring a 3-hydroxy-4-methylhexanoic acid (HMHA) moiety of cyclodepsipeptides.…”

Section: Peptidesmentioning

confidence: 99%

“…Reniochalistatin E, an octapeptide isolated and characterized from the marine sponge Reniochalina stalagmitis, displayed significant cytotoxic activity (Zhan et al 2014). In our studies, a total of 34 peptides were identified, of which more than half are cyclopeptides involved in 18 new peptides (Chen et al 2014c;Hou et al 2019bHou et al , 2019c. Particularly, LC-MS/MS-dependent molecular networking and 1 H NMR techniques were applied in order to identify new peptides.…”

Section: Peptidesmentioning

confidence: 99%

“…Interestingly, isotope labelling feeding experiments demonstrated that 13 C 1 -L-Leu was transformed into 13 C 1 -D-Leu moiety in 238 and 239 indicating that D-Leu in these molecules may be epimerized from L-Leu by a leucine racemase. Compounds 235-239 displayed selective activity in promoting angiogenesis toward the Tg (Flk1: EGFP) transgenic zebra fish D. rerio embryo (Hou et al 2019b). Applying molecular networking techniques, three new cycloheptapeptides, 245-247 (asperversiamides A-C) ( Fig.…”

Section: Peptidesmentioning

confidence: 99%

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Metabolites from marine invertebrates and their symbiotic microorganisms: molecular diversity discovery, mining, and application

Liu

Zheng

Shao

et al. 2019

Mar Life Sci Technol

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Metabolites from marine organisms have proven to be a rich source for the discovery of multiple potent bioactive molecules with diverse structures. In recent years, we initiated a program to investigate the diversity of the secondary metabolites from marine invertebrates and their symbiotic microorganisms collected from the South China Sea. In this review, representative cases are summarized focusing on molecular diversity, mining, and application of natural products from these marine organisms. To provide a comprehensive introduction to the field of marine natural products, we highlight typical molecules including their structures, chemical synthesis, bioactivities and mechanisms, structure-activity relationships as well as biogenesis. The mining of marine-derived microorganisms to produce novel secondary metabolites is also discussed through the OSMAC strategy and via partial chemical epigenetic modification. A broad prospectus has revealed a plethora of bioactive natural products with novel structures from marine organisms, especially from soft corals, gorgonians, sponges, and their symbiotic fungi and bacteria.

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“…Therefore, FBMN has recently been used in an increasing number of research reports as a method for the comprehensive investigation of natural products. 23,[28][29][30][31] In this study, we first established a solid-state fermentation system that stabilizes EGCG by β-CD inclusion complexation. The fungi isolated from FBT were incubated in the system and screened for analogues of EGCG within the LC-MS data using FBMN.…”

Section: Introductionmentioning

confidence: 99%

Feature-Based Molecular Networking Analysis of the Metabolites Produced by in vitro Solid-State Fermentation Reveals Pathways for the Bioconversion of Epigallocatechin Gallate

Xie¹,

Kong²,

Li³

et al. 2020

Preprint

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Dark teas are prepared by a microbial fermentation process. Flavan-3-ol B-ring fission analogues (FBRFAs) are some of the key bioactive constituents that characterise dark teas. The precursors and the synthetic mechanism involved in the formation of FBRFAs are not known. Using a unique solid-state fermentation system with β-cyclodextrin inclusion complexation, as well as targeted chromatographic isolation, spectroscopic identification, and Feature-based Molecular Networking (FBMN) on the Global Natural Products Social Molecular Networking (GNPS) web-platform, we reveal that dihydromyricetin and the FBRFAs, including teadenol A and fuzhuanin A, are derived from epigallocatechin gallate (EGCG) upon exposure to fungal strains isolated from Fuzhuan brick tea. In particular the strains from subphylum Pezizomycotina were key drivers for these B-/C-ring oxidation transformations. These are the same transformations seen during the fermentation process of dark teas. These discoveries set the stage to enrich dark teas and other food products for these health promoting constituents.

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Integrating Molecular Networking and ¹H NMR To Target the Isolation of Chrysogeamides from a Library of Marine-Derived Penicillium Fungi

Cited by 52 publications

References 35 publications

Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens

Structural Elucidation of Antibiotic TKR2999, an Antifungal Lipodepsipeptide Isolated from the Fungus Foliophoma fallens

Metabolites from marine invertebrates and their symbiotic microorganisms: molecular diversity discovery, mining, and application

Feature-Based Molecular Networking Analysis of the Metabolites Produced by in vitro Solid-State Fermentation Reveals Pathways for the Bioconversion of Epigallocatechin Gallate

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