0000000001308710

AUTHOR

Wenhan Lin

showing 41 related works from this author

Cytosporones, coumarins, and an alkaloid from the endophytic fungus Pestalotiopsis sp. isolated from the Chinese mangrove plant Rhizophora mucronata

2009

Chemical examination of the endophytic fungus Pestalotiopsis sp., isolated from the leaves of the Chinese mangrove Rhizophora mucronata, yielded 11 new compounds including cytosporones J-N (1-3, 5-6), five new coumarins pestalasins A-E (8-12), and a new alkaloid named pestalotiopsoid A (14), along with the known compounds cytosporone C (4), dothiorelone B (7), and 3-hydroxymethyl-6,8-dimethoxycoumarin (13). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis.

Spectrometry Mass Electrospray IonizationMagnetic Resonance SpectroscopyClinical BiochemistryPharmaceutical ScienceBiochemistryEndophyteCell Linechemistry.chemical_compoundAlkaloidsAscomycotaCoumarinsDrug DiscoveryBotanyAnimalsHumansPestalotiopsisMolecular BiologyRhizophora mucronatabiologyAlkaloidOrganic ChemistryRhizophoraceaePhenolic acidFungi imperfectibiology.organism_classificationchemistryRhizophoraceaeMolecular MedicineSpectrophotometry UltravioletMangroveBioorganic & Medicinal Chemistry
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Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a

2019

The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides. Fermentation of the fungus on solid rice medium yielded one new chlorinated diphenyl ether (1) and 13 known compounds (2-14). Addition of 5% NaBr to the rice medium increased the amounts of 4-6, while lowering the amounts of 8, 12, and 14. Furthermore, it induced the accumulation of 17 and two new brominated azaphilones, bromophilones A and B (15 and 16). Compounds 15 and 16 are the first example of azaphilones with the connection of a benzene moiety and the pyranoquinone core through a methylene group. The structures of the new compounds were elucidated based on the 1D and 2D NMR…

PharmacologyBicyclic molecule010405 organic chemistryStereochemistryOrganic ChemistryAbsolute configurationPharmaceutical ScienceEther01 natural sciences0104 chemical sciencesAnalytical Chemistry010404 medicinal & biomolecular chemistryPigmentchemistry.chemical_compoundComplementary and alternative medicinechemistryPenicillium canescensvisual_artDrug Discoveryvisual_art.visual_art_mediumMolecular MedicineMoietyFermentationMethyleneJournal of Natural Products
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Expanding the chemical diversity of an endophytic fungus Bulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach

2019

An endophytic fungus Bulgaria inquinans (isolate MSp3-1), isolated from mistletoe (Viscum album), was subjected to fermentation on solid Czapek medium. Chromatographic workup of the crude EtOAc extract yielded five new natural products (1–5). Subsequent application of the “One Strain, MAny Compounds” (OSMAC) strategy on this strain by the addition of a mixture of salts (MgSO4, NaNO3 and NaCl) to solid Czapek medium induced the accumulation of nine additional new secondary metabolites (6–13, 16), with most of them (8, 10–12) not detectable in cultures lacking the salt mixture. The structures of the new compounds were established on the basis of the 1D/2D NMR and HRESIMS data. The TDDFT-ECD m…

biologyStrain (chemistry)StereochemistryChemistryGeneral Chemical EngineeringAbsolute configuration02 engineering and technologyGeneral Chemistry010402 general chemistry021001 nanoscience & nanotechnologybiology.organism_classification01 natural sciences0104 chemical sciencesBulgaria inquinansViscum albumMoietyFermentationEnantiomer0210 nano-technologyTwo-dimensional nuclear magnetic resonance spectroscopyRSC Advances
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Cryptic Secondary Metabolites from the Sponge-Associated Fungus Aspergillus ochraceus

2019

The fungus Aspergillus ochraceus was isolated from the Mediterranean sponge Agelas oroides. The initial fermentation of the fungus on solid rice medium yielded 16 known compounds (4&ndash

Pharmaceutical ScienceBacillus subtilisOSMAC01 natural sciences03 medical and health sciencesHydrolysischemistry.chemical_compoundDrug DiscoveryAnthranilic acidAxeniclcsh:QH301-705.5Pharmacology Toxicology and Pharmaceutics (miscellaneous)030304 developmental biologyAspergillus ochraceuschemistry.chemical_classification0303 health sciencesbiology010405 organic chemistryfungiTryptophanfood and beveragesbiology.organism_classification0104 chemical sciencesAmino acidstomatognathic diseaseslcsh:Biology (General)chemistryBiochemistryco-cultivationcytotoxicityFermentationAspergillus ochraceusMarine Drugs
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Trimeric Hemibastadin Congener from the Marine Sponge Ianthella basta

2012

The first naturally occurring trimeric hemibastadin congener, sesquibastadin 1 (1), and the previously reported bastadins 3, 6, 7, 11, and 16 (2-6) were isolated from the marine sponge Ianthella basta, collected in Indonesia. The structure of 1 was elucidated on the basis of 1D and 2D NMR measurements and by HRMS. Among all the isolated compounds, the linear sesquibastadin 1 (1) and bastadin 3 (2) showed the strongest inhibition rates for at least 22 protein kinases (IC(50) = 0.1-6.5 μM), while the macrocyclic bastadins (3-6) demonstrated a strong cytotoxic potential against the murine lymphoma cell line L5178Y (IC(50) = 1.5-5.3 μM).

StereochemistryPharmaceutical ScienceMarine BiologySesquibastadinAnalytical ChemistryMiceIanthella bastaDrug DiscoveryHalogenated Diphenyl EthersAnimalsNuclear Magnetic Resonance BiomolecularProtein Kinase InhibitorsPharmacologyMolecular StructurebiologyMurine lymphomaOrganic Chemistrybiology.organism_classificationPoriferaSpongeCongenerComplementary and alternative medicineIndonesiaMolecular MedicineDrug Screening Assays AntitumorTwo-dimensional nuclear magnetic resonance spectroscopyJournal of Natural Products
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Two new metabolites from the endophytic fungus Xylaria sp. isolated from the medicinal plant Curcuma xanthorrhiza

2015

Abstract The endophytic fungus Xylaria sp. was isolated from healthy leaves of Curcuma xanthorrhiza, collected on the island of Timor, Indonesia. Two new compounds (1 and 2), together with the known resacetophenone (3), were isolated and their structures were elucidated on the basis of comprehensive NMR and mass spectral analyses. The enantiomers of rac-1 were separated by chiral HPLC and their HPLC-ECD spectra were recorded to determine the absolute configuration on the basis of TDDFT-ECD calculations. The (3R,3aR, 9aR) absolute configuration of the optically active 2 was established by comparing the experimental solution ECD spectrum with the TDDFT ones computed for the gas phase and solu…

biologyChemistryStereochemistryOrganic ChemistryAbsolute configurationXylariaEndophytic fungusOptically activebiology.organism_classificationXylaria sp.BiochemistryChiral column chromatographyCurcuma xanthorrhizaTermészettudományokDrug DiscoveryEnantiomerKémiai tudományok
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Targeted solid phase fermentation of the soil dwelling fungus Gymnascella dankaliensis yields new brominated tyrosine-derived alkaloids

2016

Seven new brominated tyrosine-derived alkaloids, gymnastatins T–Y (1–6) and dankastatin D (7), together with three known likewise brominated analogues gymnastatins I–K (8–10) were isolated from the soil fungus Gymnascella dankaliensis through fermentation on solid rice medium following addition of NaBr. None of these compounds were detected when the fungus was cultured on rice that either lacked NaBr or that contained NaCl instead, indicating a remarkable plasticity of the fungal secondary metabolism. All structures were elucidated on the basis of one and two dimensional NMR spectroscopic analyses and MS data. The absolute configuration of the new gymnastatin T (1) was determined by X-ray c…

biology010405 organic chemistryChemistryStereochemistryGeneral Chemical EngineeringAbsolute configurationGeneral ChemistryFungus010402 general chemistrybiology.organism_classification01 natural sciences0104 chemical sciencesCell culturePhase (matter)Organic chemistryFermentationTyrosineCytotoxicitySecondary metabolismRSC Advances
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Alkaloids from the Sponge-Associated FungusAspergillussp.

2012

Seven new alkaloids including tryptoquivaline K (1) and fumiquinazolines K–P (2–7), bearing a rare 1-aminocyclopropane-1-carboxylic acid residue, together with six known compounds (8–13), were isolated from the fungus Aspergillus sp. obtained from the Mediterranean sponge Tethya aurantium. The structures of the new compounds were determined by extensive analysis by 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configurations of tryptoquivaline K (1) and fumiquinazolines K and L (2, 3) were determined by TDDFT ECD calculations of their solution conformers, and the configurational assignment of the related fumiquinazolines M–P (4–7) was achieved by comparison of their ECD spe…

Circular dichroismAspergillusbiologyStereochemistryChemistryOrganic Chemistrybiology.organism_classificationMass spectrometrySpongePhysical and Theoretical ChemistryTethya aurantiumCytotoxicityConformational isomerismTwo-dimensional nuclear magnetic resonance spectroscopyEuropean Journal of Organic Chemistry
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Arthrinins A–D: Novel diterpenoids and further constituents from the sponge derived fungus Arthrinium sp.

2011

Bioassay-guided fractionation of a methanolic extract of the fungus Arthrinium sp., isolated from the Mediterranean sponge Geodia cydonium, afforded 10 natural products including five new diterpenoids, arthrinins A-D (1-4) and myrocin D (5). In addition, five known compounds were obtained, which included myrocin A (6), norlichexanthone (7), anomalin A (8), decarboxycitrinone (9) and 2,5-dimethyl-7-hydroxychromone (10). The structures of all isolated compounds were unambiguously elucidated based on extensive 1D and 2D NMR and HR-MS analyzes. The absolute configuration of arthrinins A-D (1-4) was established by the convenient Mosher method performed in NMR tubes and by interpretation of the R…

Vascular Endothelial Growth Factor AClinical BiochemistryPharmaceutical ScienceAntineoplastic AgentsBiochemistryMiceAscomycotaCell Line TumorNeoplasmsDrug DiscoveryAnimalsHumansMTT assayCytotoxicityProtein Kinase InhibitorsMolecular BiologyNeovascularization PathologicKinaseChemistryOrganic ChemistryTerpenoidIn vitroPoriferaEndothelial stem cellVascular endothelial growth factor ABiochemistryCell cultureMolecular MedicineDiterpenesProtein KinasesBioorganic & Medicinal Chemistry
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Hydroquinone derivatives from the marine-derived fungus Gliomastix sp.

2017

Eight new hydroquinone derivatives, gliomastins A–D (1–4), 9-O-methylgliomastin C (5), acremonin A 1-O-β-D-glucopyranoside (6), gliomastin E 1-O-β-D-glucopyranoside (7), and 6′-O-acetyl-isohomoarbutin (8), together with seven known analogues were isolated from the marine-derived fungus Gliomastix sp. Their structures were elucidated by extensive spectroscopic analysis including 1D and 2D NMR measurements aided by DFT NMR calculations as well as MS data. TDDFT-ECD and OR calculations were performed to determine the absolute configurations of 1 and the aglycones of 6 and 7. Compound 1 features a novel skeleton, biogenetically derived from a Diels–Alder reaction between derivatives of 11 and 1…

biologyHydroquinone010405 organic chemistryStereochemistryGeneral Chemical EngineeringAlkaloidGliomastixGeneral ChemistryFungusbiology.organism_classification01 natural sciences0104 chemical sciencesMycobacterium tuberculosis010404 medicinal & biomolecular chemistrychemistry.chemical_compoundTermészettudományokchemistryIc50 valuesKémiai tudományokCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyRSC Advances
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New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

2019

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

0106 biological sciencesStereochemistryPharmaceutical Science01 natural sciencesjasplakinolide Z<sub>5</sub>Drug Discovery<i>Jaspis splendens</i>Ic50 valuesCytotoxic T cellSpectral analysisPharmacology Toxicology and Pharmaceutics (miscellaneous)lcsh:QH301-705.5cytotoxic activitybiology010405 organic chemistryChemistry010604 marine biology & hydrobiologyMouse LymphomaJaspis splendensbiology.organism_classificationIn vitro0104 chemical sciencesSpongelcsh:Biology (General)Two-dimensional nuclear magnetic resonance spectroscopyjasplakinolide Z<sub>6</sub>Marine Drugs
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Cytotoxic Isomalabaricane Triterpenes from the Marine Sponge Rhabdastrella globostellata

2006

Fourteen isomalabaricane triterpenes were isolated from the marine sponge Rhabdastrella globostellata. In addition to the known compounds globostellatic acids A (1) and D (4) and stelliferin riboside (13), 11 of the compounds were new natural products, which included globostelletin (3), eight new globostellatic acid congeners, F to M (2, 5-11), and two new stelliferin ribosides (12 and 14). The isolated compounds were tested against three different cancer cell lines, L5178Y (mouse lymphoma), HeLa (human cervix carcinoma), and PC-12 (rat pheochromocytoma). The isomalabaricane derivatives were found to be selectively active toward the mouse lymphoma cell line L5178Y. The structures were deter…

StereochemistryRhabdastrella globostellataPharmaceutical ScienceAntineoplastic AgentsPharmacognosyPC12 CellsAnalytical ChemistryHeLaTerpeneMiceTriterpeneDrug DiscoveryTumor Cells CulturedAnimalsHumansPharmacologychemistry.chemical_classificationMolecular StructurebiologyOrganic ChemistryBiological activitybiology.organism_classificationTriterpenesTerpenoidPoriferaRatsSpongeComplementary and alternative medicinechemistryIndonesiaMolecular MedicineDrug Screening Assays AntitumorHeLa CellsJournal of Natural Products
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Pretrichodermamide C and N-methylpretrichodermamide B, two new cytotoxic epidithiodiketopiperazines from hyper saline lake derived Penicillium sp.

2015

Abstract Two new epidithiodiketopiperazines, pretrichodermamide C (1) and N-methylpretrichodermamide B (2) were isolated from the fungus Penicillium sp., derived from the sediment of a hyper saline lake located at Wadi El-Natrun in Egypt. The structures of 1 and 2 were unambiguously determined on the basis of one- and two-dimensional NMR spectroscopy and by high-resolution mass spectrometry, as well as by comparison with the literature. Compound 2 showed pronounced cytotoxicity against the murine lymphoma L5178Y cell line with an IC50 value of 2 μM.

Murine lymphomaStereochemistrymedicine.medical_treatmentPlant ScienceNuclear magnetic resonance spectroscopyBiologyMass spectrometrybiology.organism_classificationBiochemistryMicrobiologyPenicilliummedicineCytotoxic T cellCytotoxicityAgronomy and Crop ScienceSalineBiotechnologyPhytochemistry Letters
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Cytotoxic and protein kinase inhibiting nakijiquinones and nakijiquinols from the sponge Dactylospongia metachromia.

2014

Chemical investigation of the sponge Dactylospongia metachromia afforded five new sesquiterpene aminoquinones (1-5), two new sesquiterpene benzoxazoles (6 and 7), the known analogue 18-hydroxy-5-epi-hyrtiophenol (8), and a known glycerolipid. The structures of all compounds were unambiguously elucidated by one- and two-dimensional NMR and by MS analyses, as well as by comparison with the literature. Compounds 1-5 showed potent cytotoxicity against the mouse lymphoma cell line L5178Y with IC50 values ranging from 1.1 to 3.7 μM. When tested in vitro for their inhibitory potential against 16 different protein kinases, compounds 5, 6, and 8 exhibited the strongest inhibitory activity against AL…

Pharmaceutical ScienceAntineoplastic AgentsMarine BiologySesquiterpeneAnalytical Chemistrychemistry.chemical_compoundInhibitory Concentration 50MiceDrug DiscoveryAnimalsHumansProtein kinase ACytotoxicityIC50Nuclear Magnetic Resonance BiomolecularProtein Kinase InhibitorsPharmacologyBenzoxazolesMolecular StructureKinaseOrganic ChemistryQuinonesIn vitroPoriferaComplementary and alternative medicineBiochemistrychemistryCell cultureMolecular MedicineDrug Screening Assays AntitumorSesquiterpenesProto-oncogene tyrosine-protein kinase SrcJournal of natural products
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Secondary metabolites of the lichen-associated fungus Apiospora montagnei

2017

Abstract The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl w…

biology010405 organic chemistryStereochemistryAlkaloidOrganic ChemistryAbsolute configurationEtherbiology.organism_classification01 natural sciencesBiochemistryTerpenoid0104 chemical sciences010404 medicinal & biomolecular chemistrychemistry.chemical_compoundchemistryDrug DiscoveryXanthoneOrganic chemistryApiosporaTwo-dimensional nuclear magnetic resonance spectroscopyDerivative (chemistry)Tetrahedron Letters
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New 2-Methoxy Acetylenic Acids and Pyrazole Alkaloids from the Marine Sponge Cinachyrella sp.

2017

Three new 2-methoxy acetylenic acids (1–3) and a known derivative (4), in addition to three new natural pyrazole alkaloids (5–7) were isolated from an Indonesian marine sponge of the genus Cinachyrella. Compounds 5 and 6 have previously been reported as synthetic compounds. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopy as well as by mass spectrometric data. The absolute configuration of the new acetylenic acid derivatives (1–3) was established by ECD spectroscopy. All isolated compounds were evaluated for their cytotoxicity against L5178Y mouse lymphoma cells. Compounds 1–4 exhibited strong activity with an IC50 value of 0.3 µ…

food.ingredientLymphomaStereochemistrynatural productsCinachyrella sp.Pharmaceutical ScienceAntineoplastic AgentsPyrazole010402 general chemistry01 natural sciencesArticlepyrazole alkaloidMicechemistry.chemical_compoundAlkaloidsfoodTermészettudományokCell Line TumorDrug DiscoveryAnimalsOrganic chemistryKémiai tudományokCytotoxicitynatural products; marine sponge; Cinachyrella sp.; 2-methoxy acetylenic acid; pyrazole alkaloidPharmacology Toxicology and Pharmaceutics (miscellaneous)lcsh:QH301-705.5biology010405 organic chemistryChemistryAcetylenic acidAbsolute configurationNuclear magnetic resonance spectroscopybiology.organism_classificationMass spectrometricBiosynthetic PathwaysPorifera0104 chemical sciencesSpongelcsh:Biology (General)IndonesiaAlkynesddc:540Fatty Acids UnsaturatedPyrazolesDrug Screening Assays AntitumorCinachyrella2-methoxy acetylenic acidmarine spongeMarine Drugs
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Lactones from the Sponge-Derived Fungus Talaromyces rugulosus.

2017

The marine-derived fungus Talaromyces rugulosus isolated from the Mediterranean sponge Axinella cannabina and cultured on solid rice medium yielded seventeen lactone derivatives including five butenolides (1–5), seven (3S)-resorcylide derivatives (6–12), two butenolide-resorcylide dimers (13 and 14), and three dihydroisocoumarins (15–17). Among them, fourteen compounds (1–3, 6–16) are new natural products. The structures of the isolated compounds were elucidated by 1D and 2D NMR (Nuclear Magnetic Resonance) spectroscopy as well as by ESI-HRMS (ElectroSpray Ionization-High Resolution Mass Spectrometry). TDDFT-ECD (Time-Dependent Density Functional Theory-Electronic Circular Dichroism) calcul…

Circular dichroismElectrosprayTalaromyces rugulosusStereochemistryPharmaceutical ScienceFungus010402 general chemistry01 natural sciences<i>Talaromyces rugulosus</i>; lactones; ECD calculation; cytotoxicityECD calculationArticlelactonesMiceTermészettudományok4-ButyrolactoneCell Line TumorDrug DiscoveryAnimalsLeukemia L5178Kémiai tudományokCytotoxicitylcsh:QH301-705.5Pharmacology Toxicology and Pharmaceutics (miscellaneous)Nuclear Magnetic Resonance Biomolecularchemistry.chemical_classificationBiological Productsbiology010405 organic chemistryChemistryCircular DichroismTalaromyces rugulosusbiology.organism_classification0104 chemical sciencesPoriferaSpongelcsh:Biology (General)Talaromycesddc:540cytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyLactoneMarine drugs
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Cytotoxic 14-Membered Macrolides from a Mangrove-Derived Endophytic Fungus, Pestalotiopsis microspora.

2016

Seven new 14-membered macrolides, pestalotioprolides C (2), D-H (4-8), and 7-O-methylnigrosporolide (3), together with four known analogues, pestalotioprolide B (1), seiricuprolide (9), nigrosporolide (10), and 4,7-dihydroxy-13-tetradeca-2,5,8-trienolide (11), were isolated from the mangrove-derived endophytic fungus Pestalotiopsis microspora. Their structures were elucidated by analysis of NMR and MS data and by comparison with literature data. Single-crystal X-ray diffraction analysis was used to confirm the absolute configurations of 1, 2, and 10, while Mosher's method and the TDDFT-ECD approach were applied to determine the absolute configurations of 5 and 6. Compounds 3-6 showed signif…

StereochemistryMolecular ConformationPharmaceutical ScienceAntineoplastic Agents010402 general chemistryCrystallography X-Ray01 natural sciencesAnalytical ChemistryStructure-Activity RelationshipTermészettudományokDrug DiscoveryMicrosporaCytotoxic T cellStructure–activity relationshipHumansCameroonKémiai tudományokCytotoxicityIC50PharmacologyProtein Synthesis InhibitorsbiologyMolecular StructureXylariales010405 organic chemistryOrganic ChemistryPestalotiopsis microsporaFabaceaeEndophytic fungusbiology.organism_classification0104 chemical sciencesAnti-Bacterial AgentsComplementary and alternative medicineCell cultureMolecular MedicineMacrolidesJournal of natural products
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Tetrahydroanthraquinone Derivatives from the Endophytic Fungus Stemphylium globuliferm

2015

Four new tetrahydroanthraquinone derivatives, namely, dihydroaltersolanol B (1), dihydroaltersolanol C (2), and the atropisomers acetylalterporriol D (3) and acetylalterporriol E (4), were obtained from the endophytic fungus Stemphylium globuliferum, which was isolated from Juncus acutus growing in Egypt. The structures of the new compounds were unambiguously elucidated on the basis of one- and two-dimensional NMR spectroscopy, as well as by high-resolution mass spectrometry and electronic circular dichroism (ECD) spectroscopy. In addition, seven known anthraquinone derivatives 5–11 were isolated and identified on the basis of their spectral characteristics and by comparison with literature…

Circular dichroismbiologyChemistryStereochemistryOrganic ChemistryNuclear magnetic resonance spectroscopymedicine.disease_causebiology.organism_classificationPlant use of endophytic fungi in defenseMinimum inhibitory concentrationStemphylium globuliferumTermészettudományokJuncus acutusmedicinePhysical and Theoretical ChemistryAntibacterial activityKémiai tudományokEscherichia coli
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A new depsidone derivative from mangrove sediment derived fungus Lasiodiplodia theobromae

2018

A new depsidone derivative botryorhodine I (1), along with eight known compounds (2-9) were obtained from solid rice cultures of the fungal strain, Lasiodiplodia theobromae M4.2-2 isolated from a mangrove sediment sample. The structures of the isolated compounds were elucidated on the basis of 1 D and 2 D NMR analysis as well as by HRESIMS. All compounds were evaluated for their cytotoxic potential against the mouse lymphoma cell line L5178Y as well as for their antibacterial activities against a panel of Gram-positive and Gram-negative bacterial strains. Compound 3 revealed potent cytotoxic activity with an IC50 of 7.3 µM whereas compound 7 showed selective anti-bacterial activity against …

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Ircinal E, a New Manzamine Derivative from the Indonesian Marine Sponge Acanthostrongylophora ingens

2015

Chemical investigation of the MeOH extract of the sponge Acanthostrongylophora ingens afforded the new manzamine derivative ircinal E (1), in addition to six known metabolites (2–7). The structure of the new compound was unequivocally elucidated using one- and two-dimensional NMR spectroscopy, as well as high-resolution mass spectrometry. Compounds 1–6 exhibited strong to moderate cytotoxicity against the murine lymphoma L5178Y cell line with IC50 values ranging from 2.8 to 21.7 μM.

PharmacologyMurine lymphomabiologyStereochemistryAcanthostrongylophora ingensPlant ScienceGeneral MedicineNuclear magnetic resonance spectroscopybiology.organism_classificationMass spectrometrySpongechemistry.chemical_compoundComplementary and alternative medicinechemistryDrug DiscoveryBotanyMoleculeCytotoxicityDerivative (chemistry)Natural Product Communications
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Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp.

2016

Abstract Two new xanthone derivatives, 12-dimethoxypinselin ( 1 ) and 12- O -acetyl-AGI-B4 ( 2 ), as well as two new phenolic bisabolane-type sesquiterpenes, 11,12-dihydroxysydonic acid ( 15 ) and 1-hydroxyboivinianic acid ( 16 ), together with one new alkaloid, scopulamide ( 21 ) and one new α-pyrone derivative, scopupyrone ( 26 ), in addition to twenty-three known compounds ( 3 – 14 , 17 – 20 , 22 – 25 , 27 – 29 ) were isolated from solid rice cultures of the marine-derived fungus Scopulariopsis sp. obtained from the Red Sea hard coral Stylophora sp. All compounds were unambiguously identified through extensive NMR spectroscopic analyses, and by comparison with the literature. Marfey's re…

biology010405 organic chemistryChemistryStereochemistryMouse LymphomaAlkaloidOrganic ChemistryAbsolute configurationFungusbiology.organism_classificationSesquiterpene01 natural sciencesBiochemistry0104 chemical sciencesXanthone Derivatives010404 medicinal & biomolecular chemistrychemistry.chemical_compoundTermészettudományokDrug DiscoveryXanthoneScopulariopsisKémiai tudományokTetrahedron
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Induction of cryptic metabolites of the endophytic fungus Trichocladium sp. through OSMAC and co-cultivation

2019

The endophytic fungus Trichocladium sp. isolated from roots of Houttuynia cordata was cultured on solid rice medium, yielding a new amidepsine derivative (1) and a new reduced spiro azaphilone derivative (3) together with eight known compounds (4–11). Co-cultivation of Trichocladium sp. with Bacillus subtilis resulted in induction of a further new compound (2) and a 10-fold increase of 11 compared to the axenic fungal culture. Moreover, when the fungus was cultivated on peas instead of rice, a new sesquiterpene derivative (13) and two known compounds (12 and 14) were obtained. Addition of 2% tryptophan to rice medium led to the isolation of a new bismacrolactone (15). The structures of the …

biologyStereochemistryGeneral Chemical EngineeringTryptophan02 engineering and technologyGeneral ChemistryFungusBacillus subtilis010402 general chemistry021001 nanoscience & nanotechnologybiology.organism_classificationSesquiterpene01 natural sciences0104 chemical sciencesHouttuynia cordatachemistry.chemical_compoundchemistryCell culture0210 nano-technologyAxenicDerivative (chemistry)RSC Advances
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Polyketides from the marine-derived fungus Aspergillus falconensis: In silico and in vitro cytotoxicity studies.

2020

Abstract Fermentation of the marine-derived fungus Aspergillus falconensis, isolated from sediment collected from the Red Sea, Egypt on solid rice medium containing 3.5% NaCl yielded a new dibenzoxepin derivative (1) and a new natural isocoumarin (2) along with six known compounds (3–8). Changes in the metabolic profile of the fungus were induced by replacing NaCl with 3.5% (NH4)2SO4 that resulted in the accumulation of three further known compounds (9–11), which were not detected when the fungus was cultivated in the presence of NaCl. The structures of the new compounds were elucidated by HRESIMS and 1D/2D NMR as well as by comparison with the literature. Molecular docking was conducted fo…

Cell SurvivalClinical BiochemistryDrug Evaluation PreclinicalPharmaceutical ScienceAntineoplastic AgentsBiochemistrychemistry.chemical_compoundMiceStructure-Activity RelationshipCell MovementCell Line TumorDrug DiscoveryAnimalsHumansMTT assayCytotoxicityMolecular BiologyIC50Cell Proliferationchemistry.chemical_classificationbiologyDose-Response Relationship DrugMolecular StructureTopoisomeraseOrganic ChemistryOptical ImagingIn vitroIsocoumarinMolecular Docking SimulationEnzymeAspergillusBiochemistrychemistryPolyketidesbiology.proteinMolecular MedicineFermentationDrug Screening Assays AntitumorBioorganicmedicinal chemistry
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Tanzawaic acid derivatives from freshwater sediment-derived fungus Penicillium sp.

2018

Abstract Chemical investigation of a freshwater sediment-derived fungus, Penicillium sp. (S1a1), led to the isolation of three new tanzawaic acid derivatives, including penitanzchroman (1), tanzawaic acids Y (2) and Z (3), along with six known tanzawaic acid analogues (4-9), three known isochromans (10-12) and two known benzoquinones (13 and 14). The structures of the new compounds were established based on high-resolution mass spectrometry, and detailed analysis of one- and two-dimensional NMR spectroscopy. The relative configuration of the new compounds was assigned on the basis of NMR spectroscopic data including ROESY spectra. The absolute configuration was determined based on the speci…

Geologic SedimentsStereochemistrySediment (wine)Fresh WaterMicrobial Sensitivity TestsFungusMass spectrometry01 natural sciencesMiceCell Line TumorDrug DiscoveryBenzoquinonesAnimalsPharmacologyMolecular Structurebiology010405 organic chemistryChemistryPenicilliumAbsolute configurationGeneral MedicineNuclear magnetic resonance spectroscopybiology.organism_classification0104 chemical sciences010404 medicinal & biomolecular chemistryPenicilliumFatty Acids UnsaturatedWater MicrobiologyFitoterapia
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Indole alkaloids from the coprophilous fungus Aphanoascus fulvescens

2019

Abstract The Ascomycete fungus Aphanoascus fulvescens isolated from goose dung was investigated for its secondary metabolites, yielding five new indole alkaloids okaramines V–Z (1–5) and eleven known derivatives (6–16). Their structures were determined by 1D, 2D NMR spectra and HRMS data. Compounds 6, 8, 11 and 12 showed significant to moderate cytotoxicity against the mouse lymphoma cell line L5178Y with IC50 values ranging from 4.0 to 14.7 μM. Preliminary structure-activity relationships are discussed.

PharmacologyIndole testbiology010405 organic chemistryChemistryStereochemistryMouse LymphomaGeneral MedicineFungusAphanoascus fulvescensbiology.organism_classification01 natural sciences0104 chemical sciences010404 medicinal & biomolecular chemistryGoosebiology.animalDrug DiscoveryIc50 valuesCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyFitoterapia
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Cladosporinone, a new viriditoxin derivative from the hypersaline lake derived fungus Cladosporium cladosporioides

2015

A new cytotoxic viriditoxin derivative, cladosporinone (1), along with the known viriditoxin (2) and two viriditoxin derivatives (3 and 4) were obtained from the fungus C ladosporium cladosporioides isolated from the sediment of a hypersaline lake in Egypt. The structure of the new compound (1) was determined by 1D and 2D NMR measurements as well as by high-resolution ESIMS and electronic circular dichroism spectroscopy. All isolated compounds were studied for their cytotoxicity against the murine lymphoma cell line L5187Y and for their antibiotic activity against several pathogenic bacteria. Viriditoxin (2) was the most active compound in both bioassays. Compound 1 also exhibited strong cy…

Circular dichroismMagnetic Resonance SpectroscopyLymphomaAntiparasiticmedicine.drug_classStereochemistryCladosporium cladosporioidesAntineoplastic AgentsNaphtholsBiologymedicine.disease_cause01 natural sciencesInhibitory Concentration 50Micechemistry.chemical_compoundTermészettudományokBiosynthesisCell Line TumorDrug DiscoverymedicineAnimalsBioassayKémiai tudományokCytotoxicityPharmacologyBacteria010405 organic chemistryCircular DichroismPathogenic bacteriaHypersaline lakebiology.organism_classificationAnti-Bacterial Agents0104 chemical sciencesLakes010404 medicinal & biomolecular chemistrychemistryEgyptCladosporiumThe Journal of Antibiotics
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New Austalides from the Sponge-Associated Fungus Aspergillus sp.

2011

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded five new meroterpenoid metabolites, austalides M–Q (1–5), together with nine known compounds (6–13). The structures of the new compounds were unambiguously elucidated on the basis of extensive 1D and 2D NMR methods and by mass spectral analysis. Furthermore, the absolute configurations of 1 and 4 were determined by time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations, allowing the assignment of the absolute configuration of analogous compounds 2, 3, and 5. The calculations revealed that the conform…

Circular dichroismbiologyStereochemistryChemistryOrganic ChemistryAbsolute configurationTime-dependent density functional theoryChromophorebiology.organism_classificationPhthalidechemistry.chemical_compoundTermészettudományokPhysical and Theoretical ChemistryTethya aurantiumKémiai tudományokCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyEuropean Journal of Organic Chemistry
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Induction of Secondary Metabolites from the Marine-Derived Fungus Aspergillus versicolor through Co-cultivation with Bacillus subtilis

2019

AbstractA new cyclic pentapeptide, cotteslosin C (1), a new aflaquinolone, 22-epi-aflaquinolone B (3), and two new anthraquinones (9 and 10), along with thirty known compounds (2, 4 – 8, 11 – 34) were isolated from a co-culture of the sponge-associated fungus Aspergillus versicolor with Bacillus subtilis. The new metabolites were only detected in the co-culture extract, but not when the fungus was grown under axenic conditions. Furthermore, the co-culture extract exhibited an enhanced accumulation of the known constituents versicolorin B (14), averufin (16), and sterigmatocyctin (19) by factors of 1.5, 2.0, and 4.7, respectively, compared to the axenic fungal culture. The structures of the …

Circular dichroismMagnetic Resonance SpectroscopyStereochemistryPharmaceutical ScienceAnthraquinonesMicrobial Sensitivity TestsBacillus subtilisQuinolonesGram-Positive BacteriaPeptides CyclicMass SpectrometryAnalytical ChemistryMicechemistry.chemical_compoundTermészettudományokCell Line TumorDrug DiscoveryAnthraquinonesAnimalsKémiai tudományokAxenicPharmacologyDose-Response Relationship DrugbiologyCytotoxinsChemistryCircular DichroismOrganic ChemistryAbsolute configurationbiology.organism_classificationCoculture TechniquesAnti-Bacterial AgentsAspergillusComplementary and alternative medicineMolecular MedicineAspergillus versicolorAntibacterial activityBacteriaBacillus subtilisPlanta Medica
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Ophiobolin Sesterterpenoids and Pyrrolidine Alkaloids from the Sponge-Derived Fungus Aspergillus ustus

2011

Chemical examination of the fungus Aspergillus ustus isolated from the Mediterranean sponge Suberites domuncula yielded the five new ophiobolin-type sesterterpenoids 1–5 and the two new pyrrolidine alkaloids 6 and 7, together with the known compound aurantiamine and cerebroside D. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic-data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. All compounds were evaluated for their cytotoxicity against murine lymphoma cell line L5178Y.

biologyMurine lymphomaChemistryStereochemistryOrganic ChemistryFungusbiology.organism_classificationBiochemistryCatalysisCerebrosidePyrrolidineInorganic ChemistrySuberites domunculaSpongechemistry.chemical_compoundBiochemistryAspergillus ustusDrug DiscoveryPhysical and Theoretical ChemistryCytotoxicityHelvetica Chimica Acta
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Metabolites from Combretum dolichopetalum and its associated endophytic fungus Nigrospora oryzae--Evidence for a metabolic partnership.

2015

Abstract A new altersolanol derivative, 4-dehydroxyaltersolanol A ( 9 ), along with two known sesquiterpenoids, ( S )-7′-hydroxyabscisic acid ( 7 ) and ( S )-abscisic acid ( 8 ) were obtained from the endophytic fungus, Nigrospora oryzae , isolated from leaves of Combretum dolichopetalum . The host plant yielded six known compounds including ellagic acid ( 1 ), 3, 3′, 4-tri-O-methylellagic acid ( 2 ), arjunolic acid ( 3 ), 4′-dihydrophaseic acid ( 4 ), echinulin ( 5 ) and arestrictin B ( 6 ). Close structural similarities with regard to compounds 4 , 7 and 8 were observed between the metabolites from the host plant and those of the endophytic fungus. Furthermore compounds 5 and 6 are relate…

PharmacologybiologyMolecular StructureStereochemistryMouse LymphomaCombretumAnthraquinonesGeneral MedicineEndophytic fungusbiology.organism_classificationPlant Leaveschemistry.chemical_compoundMicechemistryAscomycotaCell Line TumorDrug DiscoveryEndophytesAnimalsCombretumArestrictin BNigrospora oryzaeCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyEllagic acidFitoterapia
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Cyclic heptapeptides from the soil-derived fungus Clonostachys rosea

2019

Abstract Three new cyclic heptapeptides (1–3) together with three known compounds (4–6) were isolated from a solid rice culture of the soil-derived fungus Clonostachys rosea. Fermentation of the fungus on white beans instead of rice afforded a new γ-lactam (7) and a known γ-lactone (8) that were not detected in the former extracts. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR spectra as well as by HRESIMS data. Compounds 1 and 4 exhibited significant cytotoxicity against the L5178Y mouse lymphoma cell line with IC50 values of 4.1 and 0.1 µM, respectively. Compound 4 also displayed cytotoxicity against the A2780 human ovarian cancer cell line with an IC50…

Cell SurvivalStereochemistryClinical BiochemistryPharmaceutical ScienceAntineoplastic AgentsFungusPeptides Cyclic01 natural sciencesBiochemistryMiceStructure-Activity RelationshipCell Line TumorDrug DiscoveryIc50 valuesAnimalsHumansCytotoxicityMolecular BiologyIC50Cell ProliferationDose-Response Relationship DrugMolecular Structurebiology010405 organic chemistryChemistryOrganic ChemistryGliocladiumbiology.organism_classification0104 chemical sciences010404 medicinal & biomolecular chemistryCell cultureFermentationClonostachys roseaMolecular MedicineFermentationDrug Screening Assays AntitumorTwo-dimensional nuclear magnetic resonance spectroscopyBioorganic &amp; Medicinal Chemistry
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A New Tetrahydrofuran Derivative from the Endophytic Fungus Chaetomium sp. Isolated from Otanthus maritimus

2009

1 A hitherto unidentified endophytic strain of the genus Chaetomium, isolated from the medicinal plant Otanthus maritimus, yielded a new tetrahydrofuran derivative, aureonitolic acid (), along with 5 known natural products, 2 - 6. The structure of 1 was determined by extensive spectroscopic analysis and comparison with reported data. Extracts of the fungus, grown either in liquid culture or on solid rice media, exhibited considerable cytotoxic activity when tested in vitro against L5178Y mouse lymphoma cells. Compounds 2 and 6 showed significant growth inhibition against L5178Y cells with EC50 values of 7.0 and 2.7 μg/mL, respectively, whereas 1 was inactive

Magnetic Resonance SpectroscopyStereochemistryChemical structureAntineoplastic AgentsFungusAsteraceaeChaetomiumMass SpectrometryGeneral Biochemistry Genetics and Molecular BiologyMicechemistry.chemical_compoundCell Line TumorBotanyAnimalsLeukemia L5178FuransPlants MedicinalbiologyStrain (chemistry)AsteraceaeChaetomiumbiology.organism_classificationOtanthuschemistryCell cultureGrowth inhibitionPolarographyZeitschrift für Naturforschung C
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Farinomalein derivatives from an unidentified endophytic fungus isolated from the mangrove plant Avicennia marina

2012

Five farinomalein derivatives including three new compounds, farinomaleins C–E (3–5), and one new isoindoline congener (6) were isolated from an unidentified endophytic fungus obtained from the inner tissues of healthy leaves of the mangrove plant Avicennia marina from Oman. The structures of the new compounds were unambiguously elucidated on the basis of their mass, as well as one and two dimensional NMR spectroscopic data.

Mangrove plantsbiologyChemistryOrganic ChemistryIsoindolineEndophytic fungusbiology.organism_classificationBiochemistryAvicenniachemistry.chemical_compoundCongenerAvicennia marinaDrug DiscoveryBotanyMangroveFarinomaleinTetrahedron Letters
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A new depsidone derivative from mangrove sediment derived fungus

2018

A new depsidone derivative botryorhodine I (1), along with eight known compounds (2-9) were obtained from solid rice cultures of the fungal strain, Lasiodiplodia theobromae M4.2-2 isolated from a mangrove sediment sample. The structures of the isolated compounds were elucidated on the basis of 1 D and 2 D NMR analysis as well as by HRESIMS. All compounds were evaluated for their cytotoxic potential against the mouse lymphoma cell line L5178Y as well as for their antibacterial activities against a panel of Gram-positive and Gram-negative bacterial strains. Compound 3 revealed potent cytotoxic activity with an IC50 of 7.3 µM whereas compound 7 showed selective anti-bacterial activity against …

Magnetic Resonance SpectroscopyStereochemistryPlant ScienceFungus01 natural sciencesBiochemistryDepsidesAnalytical Chemistrychemistry.chemical_compoundLactonesMiceAscomycotaAnimalsIC50biology010405 organic chemistryChemistryDepsidoneOrganic ChemistryBiological activitybiology.organism_classification0104 chemical sciences010404 medicinal & biomolecular chemistryCell cultureWetlandsMangroveDerivative (chemistry)Lasiodiplodia theobromaeNatural product research
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CCDC 1479852: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters58-dihydroxy-14-methyloxacyclotetradeca-369-trien-2-oneExperimental 3D Coordinates
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CCDC 1479853: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters58-dihydroxy-14-methyloxacyclotetradeca-369-trien-2-oneExperimental 3D Coordinates
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CCDC 1479850: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

213-dihydroxy-7-methyl-615-dioxabicyclo[12.1.0]pentadeca-311-dien-5-one monohydrateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1479851: Experimental Crystal Structure Determination

2016

Related Article: Shuai Liu, Haofu Dai, Gamall Makhloufi, Christian Heering, Christoph Janiak, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E. G. Müller, Matthias U. Kassack, Wenhan Lin, Zhen Liu, Peter Proksch|2016|J.Nat.Prod.|79|2332|doi:10.1021/acs.jnatprod.6b00473

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters58-dihydroxy-14-methyloxacyclotetradec-3-en-2-oneExperimental 3D Coordinates
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CCDC 1481781: Experimental Crystal Structure Determination

2016

Related Article: Hao Wang, Haofu Dai, Christian Heering, Christoph Janiak, Wenhan Lin, Raha S. Orfali, Werner E. G. Müller, Zhen Liu, Peter Proksch|2016|RSC Advances|6|81685|doi:10.1039/C6RA14554J

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersN-(6-bromo-1710-trihydroxy-5-oxo-3-oxatricyclo[4.3.1.024]decan-8-yl)-46-dimethyldodeca-24-dienamide methanol solvateExperimental 3D Coordinates
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CCDC 1517632: Experimental Crystal Structure Determination

2017

Related Article: Hao Wang, Blessing O. Umeokoli, Peter Eze, Christian Heering, Christoph Janiak, Werner E.G. Müller, Raha S. Orfali, Rudolf Hartmann, Haofu Dai, Wenhan Lin, Zhen Liu, Peter Proksch|2017|Tetrahedron Lett.|58|1702|doi:10.1016/j.tetlet.2017.03.052

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters8-hydroxy-3a911b-trimethyl-9-vinyl-3a455a89101111b11c-decahydro-3H-benzo[c]furo[34-f]chromene-17-dioneExperimental 3D Coordinates
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