New Antifungal and Antifeedant Metabolites from Daldinia Eschscholtzii Cocultured with Colletotrichum Pseudomajus.

The synchronous co-culture of Daldinia eschscholtzii and Colletotrichum pseudomajus produced one new linear polyketide, eschscholin C (1), along with three known compounds (2-4). One new acorane sesquiterpene, coldaldrin A (5), and one new amide derivative, coldaldamide A (6) as the probe for polyketide intermediate capture, and three known compounds (7-9) were isolated from the sequential co-culture of D. eschscholtzii with C.

The Antiphytopathogenic Metabolites and the Synergy of Endophytes sp., from the Same Host.

Two endophytes from the same host were isolated and cultured separately. Three new eremophilane sesquiterpenoids (), three new furan derivates (, -), one new polyketide (), and four known compounds (, , , ) from sp. and two new 10-membered macrolides (-), a new liner polyketide (), a new benzofuran (), and six known compounds (-) from were isolated.

The new analogues of --bergamotene from endophytic fungus sp. E121 with yam culture medium.

Two new bicyclic sesquiterpenes,Δ-2, 5, 11-trihydroxyl--cis-bergamotene () and Nigrohydroin A (), together with ten known compounds ( and -) were obtained from endophytic fungus sp. E121. The structures were elucidated on the basis of their 1D and 2D NMR spectra and mass spectrometric data.

Antifeedant, Antifungal Cryptic Polyketides with Six Structural Frameworks from Tea Endophyte Propelled by the Antagonistic Coculture with Phytopathogen and Different Culture Methods.

The antagonistic coculture with tea phytopathogen induces antifungal cryptic metabolites from isogenesis endophyte against tea phytopathogens. Sixteen new polyketides with six structural frameworks including ten cryptic ones, named coldaldols A-C (-), collediol (), and daldinrins A-L (- and ), were found from the coculture of and by different culture methods. The unique framework of compounds and featured a benzopyran-C polyketone hybrid, and compounds - were characterized by the novel benzopyran dimer.

The antifungal metabolites isolated from maize endophytic fungus Fusarium sp. induced by OSMAC strategy.

Six new sesquiterpenes, fusarchlamols A-F (1, 2, 4-7); one new natural product of sesquiterpenoid, methyltricinonoate (3); and ten known compounds were found from Fusarium sp. cultured in two different media by the one strain many compounds strategy. The compounds (1, 2, and 4-11) were isolated from Fusarium sp.

The antifungal metabolites from coculture of and associated with .

One new cyclohexenone derivative, asperfumtone A () along with six known compounds were obtained from the coculture of and associated with The configuration of was first reported in the research. The structures were determined by extensive spectroscopic analyses, and ECD calculation. Compounds , and showed significant antifungal activities against coffee phytopathogens and with MICs of 1 μg/mL.

Antifungal and antifeedant terpenoids from Paraphaeosphaeria sp. cultured by extract of host Ginkgo biloba.

Five undescribed terpenoids including a polyketide-terpenoid hybrid paraphaone, and four eremophilane sesquiterpenoids, paraphaterpenes A-D, as well as two known compounds were isolated from the endophytic fungus Paraphaeosphaeria sp. cultured by extract of host Ginkgo biloba L. The structures were established by spectroscopic analyses, and the single-crystal X-ray diffraction.

Novel Antifungal and Antifeedant Metabolites from Penicillium chrysogenum Co-Cultured with Nemania primolutea and Aspergillus fumigatus.

The endophyte Nemania primolutea, inhibited the growth of Penicillium chrysogenum in the coculture system. Four new compounds, nemmolutines A-B (1-2), and penigenumin (3) from N. primolutea, penemin (4) from P.

Three new fumagillol analogues and antifungal activity from Aspergillus fumigatus cocultured with Paraphaeosphaeria sp.

Two fungi Aspergillus fumigatus YXG-12-2, and Paraphaeosphaeria sp. YXG-18 were isolated from medicinal plant Ginkgo biloba. The interaction of endophytes and host could induce the productions of antifungal metabolites against pathogens for the plant resistance.

The antifeedant and antifungal cryptic metabolites isolated from tobacco endophytes induced by host medium and coculture.

Four new cryptic metabolites including one fumagillol derivative (2), one cyclohexenone derivative (4), one 10-membered lactone (5), and one natural 4-epi-brefeldin C (8), along with seven known compounds were found from isogenesis endophytes Aspergillus fumigatus, Penicillium janthinellum, Nigrospora sp., and Stagonosporopsis sp. induced by host Nicotiana tabacum medium and co-culture.

The induced cryptic metabolites and antifungal activities from culture of Penicillium chrysogenum by supplementing with host Ziziphus jujuba extract.

The productions of cryptic metabolites including three undescribed drimane sesquiterpenoids, penicichrins A-C, and three known compounds from Penicillium chrysogenum were activated by the host Ziziphus jujuba medium. The structures were established by comprehensive analysis of spectroscopic data. The spiro β-lactone, and gem-dimethyl dihydroxylation in induced penicichrins A-C were rare in natural products.

Chlorinated Cyclopentene Derivatives and Antifungal Activities from sp. Induced by the One Strain Many Compounds Strategy and Host Plant Culture.

Eleven new chlorinated cyclopentene derivatives, periconsins A-K, and a new diketopiperazine, periconzin, were found from cultured in three different media by the one strain many compounds strategy. Additionally, the C-1 methyl hydroxylation of chlorinated cyclopentene was found for the first time in the host plant culture. The structures were identified by extensive spectroscopic analyses, electronic circular dichroism (ECD) and C NMR calculations, and single-crystal X-ray diffraction.

The production of broad-spectrum antibiotics from phytopathogen Epicoccum sorghinum by culturing in host edible mushroom Thelephora ganbajun extract.

Metabolism of special endophytes and phytopathogens can be induced by the symbiotic interactions with the host. A phytopathogen Epicoccum sorghinum cultured in host mushroom Thelephora ganbajun medium exhibited different metabolites compared with that of ordinary medium. An unprecedented scaffold possessing the same substructure as perylenequinone mycotoxin, a first methyl rearrangement product of phytotoxin, epoxydon 6-methylsalicylate ester, three undescribed compounds, and an undescribed natural product were isolated from E.

New Metabolites, Antifeedant, Insecticidal Activities, and Reciprocal Relationship Between Insect and Fungus from Endophyte Schizophyllum commune.

Five new bisabolane sesquiterpenes, a new polyketide, along with seven known compounds, were isolated from endophyte Schizophyllum commune associated with a famous medicinal and edible plant, Gastrodia elata. Most compounds 1-12, and extract indicated antifeedant activities against silkworm with feeding deterrence index (FDI) of 21-85 %, at concentrations of 20 μg/cm , 40 μg/cm , respectively. Compound 6 indicated obvious insecticidal activity with fatality rate of 60 %, at the concentration of 20 μg/cm .

A new butenolide with antifungal activity from solid co-cultivation of and .

A new antifungal butenolide irperide () along with five known compounds were isolated from the co-culture of endophyte and pathogenic . The structure of , including the absolute configuration, was elucidated by analysis of NMR, HR-ESI-MS data and ECD spectra. Compounds , and exhibited significant antifungal activity against , with MIC values of 1, 2 and 1 μg/mL, respectively.

Antifeedant and Antifungal Activities of Metabolites Isolated from the Coculture of Endophytic Fungus Aspergillus tubingensis S1120 with Red Ginseng.

A new globoscinic acid derivative, aspertubin A (1) along with four known compounds, were obtained from the co-culture of Aspergillus tubingensis S1120 with red ginseng. The chemical structures of compounds were characterized by using spectroscopic methods, the calculated and experimental electronic circular dichroism. Panaxytriol (2) from red ginseng, and asperic acid (4) showed significant antifeedant effect with the antifeedant rates of 75 % and 80 % at the concentrations of 50 μg/cm .

The selective anti-fungal metabolites from Irpex lacteus and applications in the chemical interaction of Gastrodia elata, Armillaria sp., and endophytes.

The investigation of the metabolites from endophyte Irpex lacteus cultured in host "tian ma" (Gastrodia elata) revealed five new tremulane sesquiterpenes (1-5), and a new tetrahydrofuran derivative (6). Compound 1 was the first tremulane glucoside, and 6 possessed a rare tetrahydropyran-tetrahydrofuran scaffold. Main metabolite (2,3-dihydroxydodacane-4,7-dione, 14) from I.

The chemical diversity, the attractant, anti-acetylcholinesterase, and antifungal activities of metabolites from biocontrol Trichoderma harzianum uncovered by OSMAC strategy.

Eight new compounds (1-8) were discovered from Trichoderma harzianum associated with edible mushroom by the one strain many compounds (OSMAC) strategy. Triharzianin A (1) is the first naturally scaffold characterized by a C-prostaglandin skeleton. The configurations of 1-3, and 5 were determined by the Mosher's method, experimental and calculated ECD spectra, and plausible biosynthesis of stereospecific epoxidation.

Paraverrucsins A-F, Antifeedant, and Antiphytopathogenic Polyketides from Rhizospheric and Induced Bioactivity Enhancement by Coculturing with Host Plant .

Six new polyketides named paraverrucsins A-F (-) with oxabicyclic and dioxatricyclic skeletons, together with eight known metabolites (-), were discovered and isolated from the fermentation medium of . Paraverrucsin A-C possessed a novel decarboxylated skeleton compared with that of trichocladinols. Their structures were elucidated by extensive spectral analysis and DP4+ calculations.

Antifeedant and antiphytopathogenic metabolites from co-culture of endophyte Irpex lacteus, phytopathogen Nigrospora oryzae, and entomopathogen Beauveria bassiana.

Five new tremulane sesquiterpenoids were isolated from co-culture of endophyte Irpex lacteus, phytopathogen Nigrospora oryzae, and entomopathogen Beauveria bassiana. All compounds showed obvious antifeedant activities against silkworm with inhibition percentages of 73-99%, at concentrations of 50 μg/cm. Compound 11 indicated notable antifeedant activity with inhibition percentage of 93% at concentration of 6.

Biotransformation of natural polyacetylene in red ginseng by .

Background: Fermentation has been shown to improve the biological properties of plants and herbs. Specifically, fermentation causes decomposition and/or biotransformation of active metabolites into high-value products. Polyacetylenes are a class of polyketides with a pleiotropic profile of bioactivity.

The Cocultured and , , and the Plant Host Bidirectionally Regulate the Production of Phytotoxins by Anti-phytopathogenic Metabolites.

The distinctive nature of the endophyte , host plant, and the phytopathogen resulted in both negative and positive regulation of the production of phytotoxins from . The coculture of nonhomologous and resulted in a greater number of anti-phytopathogenic metabolites from the dominant endophyte than the coculture of homologous and The coculture of the phytopathogen and either the nonhomologous (isolation of and from the different plants) or homologous (isolation of and from the same plant) endophyte from different sources indicated that the nonhomologous grew faster than the homologous , and the production of phytotoxic azaphilone from the phytopathogenic decreased due to the inhibition resulting from being cocultured with nonhomologous . On the other hand, the production of phytotoxic azaphilone was promoted by the coculture of two phytopathogens, and .

Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut and The Potential Bioactivity Modification by Oxidative Metabolism.

The ω-hydroxyl-panaxytriol () and ω-hydroxyl-dihydropanaxytriol ()-are rare examples of polyacetylene metabolism by microbial transformation, and these new metabolites (, ) from fermented red ginseng (FRG) by solid co-culture induction of two should be the intermediates of biotransformation of panaxylactone (metabolite ). The metabolic pathway of panaxylactone was also exhibited. The ingredients of red ginseng (RG) also induced the production of rare 6/5/5 tricyclic ring spiro-γ-lactone skeleton ().

Induction of Antiphytopathogenic Metabolite and Squalene Production and Phytotoxin Elimination by Adjustment of the Mode of Fermentation in Cocultures of Phytopathogenic and .

The investigation of the metabolites from different cocultures of and in solid medium revealed two new squalenes ( and ); one new azaphilone (); two new tremulane sesquiterpenes ( and ); and three known compounds, conocenol B (), conocenol C (), and 4-(4-dihydroxymethylphenoxy)benzaldehyde (). The antagonistic relationship was examined by studying metabolite production. The production of compounds and by after the induction of coculture indicated significant selectivity for antifungal activity against phytopathogenic , with MICs of 16 μg/mL; compounds and also exhibited antifungal activities in vivo against infected by at concentrations of 100 μg/mL.