Novel Sorbicillin Derivatives with an Unprecedented Carbon Skeleton from the Sponge‐Derived Fungus <i>Trichoderma</i> Species

Neumann, Kerstin; Abdel‐Lateff, Ahmed; Wright, Anthony D.; Kehraus, Stefan; Krick, Anja; König, Gabriele M.

doi:10.1002/ejoc.200700548

Cited by 5 publications

(7 citation statements)

References 2 publications

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“…The unsaturated γ -lactone was supposed to be originated from sorbicillinol through reduction, hemiketal formation, retro -Claisen cleavage [ 32 ], and terminal hydroxylation. Neumann [ 33 ] postulated that the pyrone unit was derived from sorbicillinol by multiple steps. We suggest oxidation to lose a C 3 unit in sorbicillinol to produce 8 and 7 ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

Sorbicillinoid-Based Metabolites from a Sponge-Derived Fungus Trichoderma saturnisporum

et al. 2018

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Antibacterial activity assessment and high performance liquid chromatography associated with nuclear magnetic resonance (HPLC/NMR) data revealed that the EtOAc extract of the fermented endophytic fungus Trichoderma saturnisporum DI-IA, obtained from the marine sponge Dictyonella incisa, contained conjugated olefinic metabolites with antibacterial activity. Chemical examination of the fungal strain resulted in the isolation of eight new sorbicillinoid-based compounds, namely saturnispols A–H (1–8). Their structures were determined on the basis of extensive spectroscopic analysis, including the experimental and calculated electronic circular dichroism (ECD) data for the configurational assignments. Saturnispol F exerted significant inhibition against a panel of bacteria strains including vancomycin-resistant enterococci (VRE) with a minimum inhibitory concentrations (MIC) ranging from 1.63 to 12.9 μg/mL, while saturnispol H showed selective effects against VRE and B. subtilis.

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Section: Resultsmentioning

confidence: 99%

Sorbicillinoid-Based Metabolites from a Sponge-Derived Fungus Trichoderma saturnisporum

et al. 2018

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“…Compound 15 showed reduced L-glutamate toxicity in N18-RE-105 cells with EC 50 values of 71 µM, and compound 16 had DPPH radical scavenging activity (IC 50 , 30 µM) [15,16]. A new salicylamide derivative termed JBIR-58 (17) [17] and two new pyrazinones JBIR 56-57 (18)(19) (Figure 1) [18] were isolated from actinomyces Streptomyces SpD081030ME-02 and SpD081030SC-03, which originated in Demospongiae sponges, respectively. Compound 17 exhibited a weak cytotoxic effect on human cervical carcinoma (HeLa) cells (IC 50 , 28 µM).…”

Section: Class Demospongiaementioning

confidence: 99%

Biological and Chemical Diversity of Marine Sponge-Derived Microorganisms over the Last Two Decades from 1998 to 2017

et al. 2020

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Marine sponges are well known as rich sources of biologically natural products. Growing evidence indicates that sponges harbor a wealth of microorganisms in their bodies, which are likely to be the true producers of bioactive secondary metabolites. In order to promote the study of natural product chemistry and explore the relationship between microorganisms and their sponge hosts, in this review, we give a comprehensive overview of the structures, sources, and activities of the 774 new marine natural products from sponge-derived microorganisms described over the last two decades from 1998 to 2017.

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“…This led to the isolation of compounds 2 -11. The structures of all compounds were determined/confi rmed by interpretation of their spectroscopic data (1D and 2D NMR, CD, MS, UV and IR) (Neumann et al, 2007).…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…The fungus was cultivated on a solid glucose biomalt medium with added artifi cial sea water. Successive fractionation of the EtOAc extract, produced by extraction of the cultivation media and associated fungal mycelia, by vacuum liquid chromatography (VLC) over reversed phase (RP-18) silica followed by reversed phase (RP-18) HPLC yielded a new pyranone derivative, trichopyrone (1), and ten known compounds, namely four sorbicillinoid polyketide derivatives, trichodermanone A-D (2 -5) (Neumann et al, 2007), two hexaketide derivatives, rezishanone (6) (Maskey et al, 2005) and vertinolide (7) (Trifonov et al, 1982), three dodecaketides, trichodimerol (8) (Abe et al, 1998a), bislongiquinolide (trichotetronine, 9) (Abe et al, 1999), and bisvertinol (10) (Trifonov et al, 1986), as well as 2-furancarboxylic acid (11) (Corey et al, 1958) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Trichopyrone and Other Constituents from the Marine Sponge-Derived Fungus Trichoderma sp.

Abdel‐Lateff

Fisch

Wright

2009

Zeitschrift Für Naturforschung C

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The fungus Trichoderma viride was isolated from the Caribbean sponge Agelas dispar, which was collected from waters around the island of Dominica. Its EtOAc extract, exhibiting mild radical scavenging properties, was mass cultivated and found to produce a new pyranone derivative, trichopyrone (1), and ten compounds, namely four sorbicillinoid polyketide derivatives, trichodermanone A-D (2 -5), two hexaketide derivatives, rezishanone (6) and vertinolide (7), three known dodecaketides, trichodimerol (8), bislongiquinolide (trichotetronine, 9), and bisvertinol (10), as well as 2-furancarboxylic acid (11). The structures of all compounds were determined by interpretation of their spectroscopic data (1D and 2D NMR, MS, UV and IR). The biological activities of all isolates were evaluated in a series of bioassays (radical scavenging, antioxidant, antimicrobial, inhibition of HIV-1 RT). The majority had very weak or no effects in the applied test systems.

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Novel Sorbicillin Derivatives with an Unprecedented Carbon Skeleton from the Sponge‐Derived Fungus Trichoderma Species

Cited by 5 publications

References 2 publications

Sorbicillinoid-Based Metabolites from a Sponge-Derived Fungus Trichoderma saturnisporum

Sorbicillinoid-Based Metabolites from a Sponge-Derived Fungus Trichoderma saturnisporum

Biological and Chemical Diversity of Marine Sponge-Derived Microorganisms over the Last Two Decades from 1998 to 2017

Trichopyrone and Other Constituents from the Marine Sponge-Derived Fungus Trichoderma sp.

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