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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. The antifungal activity of Paraphaeosphaeria sp. cultured by extract of G. biloba against the plant pathogen Alternaria alternata was significant and higher than that of PDB medium. Tested compounds indicated antifeedant activities against silkworms with feeding deterrence index at 10–70%. Paraphaone, paraphaterpenes A, C, D and alternariol methyl ether showed significant antifungal activities against the phytopathogens A. alternata , Aspergillus fumigatus , and entomopathogen Beauveria bassiana with MICs ≤4 μg/mL. And the preliminary structure-activity relationship of eremophilane sesquiterpenoids was exhibited. The culture of Paraphaeosphaeria sp. by host G. biloba medium afforded agricultural antibiotics. [Display omitted] • Five undescribed terpenoids were found from Paraphaeosphaeria sp. • The meroterpenoid, sesquiterpenoids, and alternariol derivative showed significant antibiosis. • The interaction of Paraphaeosphaeria sp. and host G. biloba induced the antifungal activity. • The structure-activity relationships of eremophilane sesquiterpenoids were indicated. [ABSTRACT FROM AUTHOR]

Eight previously undescribed metabolites including of lovastatin analogues, a pair of diastereoisomers, a cyclopentenone dimer, and three polyketides were isolated from the culture of Aspergillus terreus YIM PH30711. Two types of unprecedented skeletons, benzene-cyclopentanone complex and linear polyketide, and an unusual dimer structure were determined by spectral analysis. Compound, 3α-hydroxy-3,5-dihydromonacolin L showed moderate activity against HMG-CoA reductase, with an inhibition ratio of 34% at the concentration of 50 μM, while lovastatin and dihydromonacolin K ethyl ester presented much stronger activity against HMGR with inhibition rates of 85% and 90% at the concentration of 50 μM, respectively. Aspereusin A was active against AChE with a ratio of 62% at the concentration of 50 μM, while its stereomers did not showed obvious inhibition (<10%). The configuration at C-4 of these three diastereoisomers was crucial in the inhibition against AChE, and the β -orientation of substituted methoxyl acrylic acid should be beneficial to the combining with AChE. [ABSTRACT FROM AUTHOR]

Two undescribed polyketides canecines A-B, one unreported cyclopentenone canecine C, together with 12 known compounds were isolated from an extract of the fungus Penicillium canescens DJJ-1. Their structures were elucidated by detailed analysis of spectroscopic data, NMR calculations with d J -DP4 or DP4+, and their absolute configurations were further determined by quantum chemical calculations of ECD spectra or X-crystallography. Canecine A was a grisan polyketide featuring a dimethyltetrahydro-4 H -furo[2,3- b ]pyran. Canecine A exhibited significant inhibitory activity against Candida albicans with an MIC value of 1 μg/mL and showed inhibitory effect on nitric oxide production in LPS-activated RAW264.7 macrophages. These results enrich the structural diversities of polyketides from endophytic fungi. Polyketides with antimicrobial activities from Penicillium canescens DJJ-1 of Aconitum brevicalcaratum Diels (Ranunculaceae). [Display omitted] • Three undescribed polyketides were isolated from Penicillium canescens DJJ-1. • One compound showed antimicrobial activities. • One compound showed inhibitory effects on LPS-induced NO production. [ABSTRACT FROM AUTHOR]

The fungus Pseudopestalotiopsis theae isolated from the fresh leaves of Illigera celebica, has been reported to be a pathogenic fungus that can cause gray blight on tea leaves, a disease characterized by the appearance of necrotic lesions on tea leaves. The pathogenic substances in this fungus have not been clearly identified. Considering the possible involvement of specialized metabolites in symptom appearance, a chemical investigation of specialized metabolites on P. theae was conducted, resulting in the isolation of eight meroterpenoids, including six undescribed biscognienynes G-L and two known ones (biscognienynes B and D). The structures of these new compounds were characterized by extensive NMR spectroscopic and HR-ESI-MS data, and their absolute configurations were elucidated by ECD calculations. Except for biscogniyne L, all the isolated biscognienynes showed different degrees of phytotoxicity to tea in vivo , thereby revealing for the first time the substances in P. theae that cause tea gray blight. Inspired by the fact that phytotoxins produced by pathogenic fungus are an effective resource for designing natural and safe bioherbicides, when assayed the herbicidal activity through Petri dish bioassays, biscognienynes G-J showed phytotoxic effects against seed germination and seedling growth of Setaria viridis , strongly inhibiting seed germination percentage and radicle and germ lengths of seedlings. The results of this study demonstrated the great potential of biscognienynes G-J to be proposed and developed as ecofriendly herbicides. Six undescribed meroterpenoids were isolated from Pseudopestalotiopsis theae , four of them showed potential herbicidal activity toward Setaria viridis. [Display omitted] • Six undescribed meroterpenoids were isolated from Pseudopestalotiopsis theae. • Biscognienynes G-K showed varying degrees of phytotoxicity to tea leaves in vivo. • Biscognienynes G-J showed potential herbicidal activities toward Setaria viridis. [ABSTRACT FROM AUTHOR]

Five unprecedented polyketide metabolites were isolated and characterized from a rhizospheric soil-derived Penicillium sp. YUD17004. Their diverse structures included two indanone-type polyketides penicillyketides A and B, a phthalide-like polyketides penicillyketide C, a symmetrical chromone dimer penicillyketide D, along with a pyrone derivative pyranlyketide, which were elucidated by spectroscopic data interpretation and quantum chemical electronic circular dichroism calculation. Notably, the structures of penicillyketides A and B feature a highly functionalized indanone ring nucleus, but differ from other indanone-containing polyketides by the alkyl substitution pattern. The structure of penicillyketide C comprises a furanone ring instead of the hydroxycyclopentenone ring characteristic for penicillyketides A and B, and represents an undescribed arrangement within C 17 polyketides. Penicillyketide D represented the first example of a chromone homodimer with the bridge at C-2/2′. Penicillyketide B exhibited weak anti-inflammatory activity with an IC 50 value of 32 ± 1.0 μM. Penicillyketide D displayed weak cytotoxicity against MCF-7 cell line with an IC 50 value of 25 ± 0.9 μM. [Display omitted] • Five undescribed polyketides were isolated from a rhizospheric soil-derived Penicillium sp. YUD17004. • All of the isolated polyketides represent four skeletons. • The stereochemistry was elucidated by TDDFT-ECD calculation methods. • Their cytotoxic and anti-inflammatory activities were evaluated. [ABSTRACT FROM AUTHOR]

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. Cryptic metabolites, monaspurpurone was first found in Penicillium. 4-Methoxy-3-methylgoniothalamin, and 2-hydroxy-l-phenyl-l,4-pentanedione were second example of isolation. Penicichrin A, monaspurpurone, 4-methoxy-3-methylgoniothalamin, physcion, ergosterol, and ergosta-7,22-dien-3 β -ol had antifungal activities against phytopathogens, P. chrysogenum , Alternaria alternata and Aspergillus fumigatus with MICs ≤2 μg/mL, and 2-hydroxy-l-phenyl-l,4-pentanedione had flowering activity. So the chemical constituents from Z. jujuba could induce the productions of cryptic metabolites with plant growth-promoting activity from endophyte P. chrysogenum. [Display omitted] • Cryptic metabolites including three undescribed ones were found from P. chrysogenum by host medium. • The spiro β -lactone, and gem-dimethyl dihydroxylation in penicichrins were rare in natural products. • The induced compounds indicated plant growth-promoting activities. [ABSTRACT FROM AUTHOR]

A chemical investigation of the endophytic fungus Diaporthe destruens from the Hernandiaceae plant Illigera orbiculata C. Y. Wu collected from southern Yunnan Province, China, led to the isolation of six undescribed compounds, including two azaphilone analogs, which are a pair of epimers (13 R- hydroxy-chermesinone A and 13 S- hydroxy-chermesinone A); a pyrrole derivative (1-(4-(methoxymethyl)-1H-pyrrol-3-yl)ethan-1-one); an isoindolone derivative (4-hydroxy-6-methoxyisoindolin-1-one); a benzylbenzene derivative (destruensine A) and a conjectural fragment of polyketide ((2 R ,4 R)-2-(methoxymethyl)pentane-1,4-diol) along with nine known compounds. Their structures were elucidated by spectroscopic methods and HRESIMS, and the absolute configurations were further confirmed by electronic circular dichroism (ECD) and chemical derivatization. The antimicrobial activities, anti-acetylcholinesterase activities, antiproliferation, and NO production inhibitory effects of compounds 1 – 15 were evaluated. Fifteen specialised products, including six undescribed structures, were obtained from Diaporthe destruens hosted in Illigera orbiculata. Their bioactivities were evaluated. [Display omitted] • Six undescribed compounds were isolated from the fungus Diaporthe destruens. • The absolute configurations of the undescribed compounds were established. • The bioactivities of the isolated compounds were evaluated. [ABSTRACT FROM AUTHOR]

Ten undescribed C 12 polyketide phialocetones A-J, featuring twelve-, six- and five-membered lactone moieties, were isolated from a rhizospheric soil-derived Phialocephala sp. YUD18001 associated with Gastrodia elata. Their structures were established by NMR spectroscopic analysis and HRMS, while their absolute configurations were determined by computational methods and chemical reactions. All isolated compounds were evaluated for their anti-inflammatory and cytotoxic activities. As a result, phialocetone D exhibited moderate effects against NO production in lipopolysaccharide (LPS)-induced RAW264.7 cells with an IC 50 value of 14.77 μ M, while phialocetone E showed cytotoxicity against HL-60 and SW480 cell lines with IC 50 values of 19.04 and 10.22 μ M, respectively. Ten undescribed C 12 polyketide phialocetones were isolated from a rhizospheric soil-derived Phialocephala sp. YUD18001 associated with Gastrodia elata. [Display omitted] • Ten undescribed C 12 lactones were isolated from Phialocephala sp. YUD18001. • The lactones were divided into three types, including 12-, 6- and 5-membered ring. • Some of the lactones showed significant biological activities. [ABSTRACT FROM AUTHOR]

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. sorghinum cultured in T. ganbajun. Episorin A and epicosorin A were produced from E. sorghinum induced by culturing in host medium. Episorin A was the first example of perylenequinone analogue in the natural products. These induced compounds and other metabolites showed notable antibiosis against endogenous fungi, and insect existing in mushroom. Induced episorin A showed significant inhibitory effects on nitric oxide production in LPS-activated macrophages, and anti-acetylcholinesterase with the IC 50 at 5.40 ± 0.25 μ M, and 4.32 μ M, respectively, and cytotoxicity against HL-60, A-549, SMMC-7721, MCF-7 and SW480 with IC 50 at 14.21 ± 0.53, 17.93 ± 0.22, 18.17 ± 0.63, 28.36 ± 0.43, and 18.20 ± 1.03 μ M. [Display omitted] • Six undescribed compounds were found from culture of Epicoccum sorghinum in Thelephora ganbajun medium. • The inducing novel antibiotic, episorin A indicated significant activities. • The interaction of host and endogenous fungi can induce the production of novel antibiotics. [ABSTRACT FROM AUTHOR]

Diterpenoid alkaloids, named vilmorines A–D, in addition to fifteen known alkaloids, were isolated from roots of Aconitum vilmorinianum . Their structures were established on the basis of extensive spectroscopic analyses. Antibacterial and antioxidant studies on isolated compounds were also carried out. [ABSTRACT FROM AUTHOR]

The investigation of the metabolites from Arthrinium arundinis DJ-13 grown in solid medium revealed six undescribed cytochalasans, arundisins A-F and twelve known compounds. Their structures were initially investigated in detail by spectroscopic analyses and were further confirmed by X-crystallography and ECD experiments. In the in vitro bioassays, arundisins A and B showed cytotoxic activity against the MCF-7 breast cancer cell line with IC 50 values of 18.82 ± 0.36 and 15.20 ± 0.42 μ M, respectively. Arundisin F exhibited potent antibacterial activity against Escherichia coli with MIC of 8.00 μ g/mL (kanamycin, 2.00 μ g/mL), and arundisin D displayed gently antibacterial activity against Candida albicans with MIC of 32.00 μ g/mL (Nystatin, 1.00 μ g/mL). Six undescribed cytochalasans were isolated from Arthrinium arundinis DJ-13. [Display omitted] • Six previously undescribed cytochalasans were isolated from Arthrinium arundinis DJ-13. • Three compounds showed cytotoxic activity. • Two compounds showed antibacterial activity. [ABSTRACT FROM AUTHOR]

Seven previously undescribed sesterterpenes were characterized from Penicillium roqueforti YJ-14 by solid fermentation. Their structures were initially investigated in detail by spectroscopic analyses and HR-ESI-MS and were further confirmed by X-crystallography. In in vitro bioassays, compounds 1 , 5 and 7 showed cytotoxic activity against the MCF-7 breast cancer cell line with IC 50 values of 7.98 ± 0.93, 6.42 ± 0.41 and 7.32 ± 0.18 μ M, respectively. Compounds 5 and 7 displayed significant cytotoxicity against the A549 lung cancer cell line (IC 50 values of 4.83 ± 0.22 μ M and 4.58 ± 0.85 μ M, respectively). In addition, compound 5 showed an obvious inhibitory effect on nitric oxide production in LPS-activated RAW264.7 macrophages with an IC 50 value of 9.53 ± 0.16 μ M. [Display omitted] • Seven new sesterterpenes were isolated from Penicillium roqueforti YJ-14. • Three compounds showed cytotoxic activity. • One compound showed anti-inflammatory activity. [ABSTRACT FROM AUTHOR]