Cinatrins D and E, and virgaricin B, three novel compounds produced by a fungus, Virgaria boninensis FKI-4958

Ishii, Takahiro; Nonaka, Kenichi; Sugawara, Akihiro; Iwatsuki, Masato; Masuma, Rokuro; Hirose, Tomoyasu; Sunazuka, Toshiaki; Ōmura, Satoshi; Shiomi, Kazuro

doi:10.1038/ja.2015.45

Cited by 12 publications

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References 14 publications

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“…Although this transformation seems straightforward, very few natural products have been described from similar metabolic pathways. As examples, we can cite some citric acid derivatives connected to a long alkyl chain mostly isolated from fungi or other fungal itaconic acid derivatives derived from an aldol condensation between pyruvic acid and fatty acids in the same manner. − We were not able to find other fatty acid derivatives connected to an aromatic derivative such as phenylalanine or tyrosine in the literature. Interestingly, the control of the stereochemistry of the C-2/C-2′ bond would suggest the involvement of an enzymatic process.…”

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confidence: 99%

Callyspongidic Acids: Amphiphilic Diacids from the Tropical Eastern Pacific Sponge Callyspongia cf. californica

et al. 2018

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The first chemical study of the marine sponge Callyspongia cf. californica widely distributed along the coasts of the Tropical Eastern Pacific led to the identification of a new family of amphiphilic derivatives called callyspongidic acids. The four isolated metabolites 1−4 feature a hydrophilic diacid end opposed to both an aromatic moiety and a long alkyl chain. They were evaluated against a panel of pathogenic microbes and seven tumoral cell lines, displaying moderate inhibitory properties against the A2058 melanoma cell line with an IC 50 of 3.2 μM for callyspongidic acid C13:0 (2).

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confidence: 99%

Callyspongidic Acids: Amphiphilic Diacids from the Tropical Eastern Pacific Sponge Callyspongia cf. californica

et al. 2018

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“…The geometries of ∆ 7,9,13,15 were deduced as E -form by their large coupling constants ( Table 1 ) and the chemical shift of terminal methyl (C-21) was δ C 18.1, revealing the geometry of ∆ 19 was E -form [ 11 , 12 ]. Therefore, 1 was determined as a new variotin derivative with a non-branched side chain and named variotin B [ 13 ].…”

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confidence: 99%

Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus Aspergillus unguis and Their Anti-Inflammatory Activity

et al. 2022

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Aspergillus is well-known as the second-largest contributor of fungal natural products. Based on NMR guided isolation, three nitrogen-containing secondary metabolites, including two new compounds, variotin B (1) and coniosulfide E (2), together with a known compound, unguisin A (3), were of isolated from the ethyl acetate (EtOAc) extract of the deep-sea fungus Aspergillus unguis IV17-109. The planar structures of 1 and 2 were elucidated by an extensive analysis of their spectroscopic data (HRESIMS, 1D and 2D NMR). The absolute configuration of 2 was determined by comparison of its optical rotation value with those of the synthesized analogs. Compound 2 is a rare, naturally occurring substance with an unusual cysteinol moiety. Furthermore, 1 showed moderate anti-inflammatory activity with an IC50 value of 20.0 µM. These results revealed that Aspergillus unguis could produce structurally diverse nitrogenous secondary metabolites, which can be used for further studies to find anti-inflammatory leads.

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“…The large values of J 8 , 9 (15.4 Hz) and J 10 , 11 (15.1 Hz) supported the E configuration for the double bonds at C-8/C-9 and C-10/C-11 in 2 . The relative configuration of the γ-lactam ring was deduced through the ROESY spectrum and by comparison with pramanicin A ( 1 ) ( Harrison et al, 2000 ), virgaricins A and B ( Ishii et al, 2012 , 2015 ). The NOE correlations between 3-OH/H-4, H-4/H 2 -6 indicated that 3-OH, H-4 and H 2 -6 were located on the same side of the ring.…”

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confidence: 99%

Induction of New Lactam Derivatives From the Endophytic Fungus Aplosporella javeedii Through an OSMAC Approach

et al. 2020

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Fermentation of the endophytic fungus Aplosporella javeedii on solid rice medium in presence of either 3.5% NaNO 3 or 3.5% monosodium glutamate caused a significant change of the fungal metabolite pattern compared to fungal controls grown only on rice. Chemical investigation of the former fungal extracts yielded 11 new lactam derivatives, aplosporellins A–K ( 2 – 12 ), in addition to the known compound, pramanicin A ( 1 ). All of these compounds were not detected when the fungus was grown on rice medium without these activators thereby indicating the power of this OSMAC approach. The structures of the new compounds were elucidated by one- and two- dimensional NMR spectroscopy, DFT-NMR calculations and by mass spectrometry as well as by comparison with the literature whereas the absolute configuration of the lactam core was determined by TDDFT-ECD and OR calculations. Pramanicin A ( 1 ) showed strong cytotoxicity against human lymphoma (Ramos) and leukemia (Jurkat J16) cells with IC 50 values of 4.7 and 4.4 μM, respectively. Mechanistic studies indicated that 1 activates caspase-3 and induces apoptotic cell death.

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Cinatrins D and E, and virgaricin B, three novel compounds produced by a fungus, Virgaria boninensis FKI-4958

Cited by 12 publications

References 14 publications

Callyspongidic Acids: Amphiphilic Diacids from the Tropical Eastern Pacific Sponge Callyspongia cf. californica

Callyspongidic Acids: Amphiphilic Diacids from the Tropical Eastern Pacific Sponge Callyspongia cf. californica

Nitrogen-Containing Secondary Metabolites from a Deep-Sea Fungus Aspergillus unguis and Their Anti-Inflammatory Activity

Induction of New Lactam Derivatives From the Endophytic Fungus Aplosporella javeedii Through an OSMAC Approach

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