Two new sesquiterpenes from cultures of the higher fungus Pholiota nameko

Two new sesquiterpenes (1–2), along with one known sesquiterpene (3), were isolated from cultures of the higher fungus Pholiota nameko. The structures of new compounds were elucidated by extensive spectroscopic methods. The known compound was identified by comparing its spectroscopic data with those reported in the literature. All compounds were evaluated for their cytotoxicities against five human cancer cell lines.     

Two new acids from mangrove endophytic fungus (No. ZZF13)

Two new acids 1 and 2, together with a known compound, purpactin A (3), were isolated from endophytic fungus No. ZZF13. Their structures were elucidated on the basis of 1D, 2D NMR, and HREIMS spectra. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp.336-337, July-August, 2008. Original articlesubmitted April 24, 2007.     

Two new aromatic polyketides from a deep-sea fungus Penicillium sp. SCSIO 06720

Abstract

Two new compounds, 5-[2-hydroxypropane-1-yl]-2,6-dimethlbenzene-1,3-diol (1) and coniochaetone L (2), together with 19 known compounds (3–21), were isolated from a deep-sea fungus, Penicillium sp. SCSIO 06720. Their structures and absolute configurations were elucidated by detailed NMR, MS spectroscopic analyses, chiral-phase HPLC analysis, and electronic circular dichroism spectra. All the isolated compounds (1–21) were tested for their antibacterial and HIV latency-reversal activities. Among these compounds, compound 16 showed moderate antibacterial activities against Staphylococcus aureus ATCC 29213 and Methicillin-Resistant Staphylococcus Aureus-shh-1 with MIC values of 10.4?±?3.7?μg/mL and 46.9?±?29.7?μg/mL, respectively, which were comparable to that of the positive control ampicillin with MIC values of 0.5?±?0.4?μg/mL and 2.7?±?0.9?μg/mL, respectively.     

Two new phenylspirodrimanes from the deep-sea derived fungus Stachybotrys sp. MCCC 3A00409

Two new phenylspirodrimanes, stachybotrin H (1) and stachybotrysin H (9) together with eleven known analogues (2–8, 10–13) were isolated from deep-sea derived Stachybotrys sp. MCCC 3A00409. Their structures were determined by extensive NMR data and mass spectroscopic analysis. Compounds 9–12 showed weak cytotoxicity against three human cancer cell lines K562, Hela and HL60 with IC₅₀ in the range of 18.5–52.8 μM.     

Two new isochromane derivatives penisochromanes A and B from ascidian-derived fungus Penicillium sp. 4829

Seven polyketides, including two new isochromanes, penisochromanes A and B (1 and 2), as well as five known compounds were obtained from an ascidian-derived fungus Penicillium sp. 4829. Their structures were identified by extensive spectroscopic analyses. The structures of compounds 1 and 3 were further determined by the X-ray crystallography. Compounds 1 and 2 were the first example of isochromane with three adjacent oxy substituents in natural source. Compound 4 exhibited selective activities against two Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, with MIC values 6.25 and 12.5 μM, respectively.     

Two new secondary metabolites from a mangrove-derived fungus Cladosporium sp. JJM22

Two new compounds (1 and 2), together with six known compounds (3–8), were obtained from the Cladosporium sp. JJM22, an endophytic fungus isolated from the stem bark of the mangrove plant Ceriops tagal collected in South China Sea. Their structures were elucidated on the basis of detailed spectroscopic analysis. The absolute configurations of 1 and 2 were confirmed by the comparison of optical rotation and the CD data with those of known compounds. The inhibitory activities of the isolated compounds against six terrestrial pathogenic bacteria and human cervical carcinoma Hela cell line were evaluated. Compound 3 exhibited a broad spectrum of antibacterial activities.     

Two new polyhydroxysterols produced by Fusarium solani,an endophytic fungus from Chloranthus multistachys

A highly antagonistic endophytic fungus, designated strain CL39, was originated from the leaves of Chloranthus multistachys collected in Wulong of Chongqing municipality of China in November 2015. The strain was identified as Fusarium solani based on morphological characteristics, 5.8S gene and internal transcribed spacer sequence analysis. Two new compounds, 2β, 9α-dihydroxy-5α-methoxyergosta-7, 22-diene (1), 2β, 6β-dihydroxy-5α-methoxyergosta-7, 22-diene (2) have been isolated from the culture broth of the strain. Structures of the new compounds were elucidated by detailed analysis of their spectroscopic data aided by the comparison with reported data of related derivatives, and found to belong to the polyhydroxylated steroids with a hydroxyl at C-2 instead of C-3, a rare structure among the steroids. The extract of this strain and all isolated compounds were evaluated for their antagonistic activities.     

A New Macrocyclic Trichochecene from Soil Fungus

From fermentation broth of soil fungus 254-2 obtained from Yunnan province, a new macrocylic trichochecene was isolated. The structure was determined on the basis of spectroscopie evidences especially the 2-D NMR spectra.     

A new isochroman from the marine endophytic fungus 1893#

A new isochroman, 6-hydroxy-3-methylisochroman-5-carboxylic acid, and six known compounds were isolated from the culture of marine-derived mangrove fungus 1893#. Their structures were elucidated by analysis of spectroscopic data. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 114–116, March–April, 2006.     

Three new aspochalasin derivatives from the marine-derived fungus Spicaria elegans

<正>Three new aspochalsins(R-T)(1-3) were isolated from the marine-derived fungus Spicaria elegans.Their structures were elucidated on the basis of comprehensive spectral analysis including 1D and 2D NMR techniques,and HR-ESI-MS.     

Two new compounds,Talaromycin A and B,isolated from an endophytic fungus,Talaromyces aurantiacus

Abstract

Two new compounds Talaromycin A (1) and Talaromycin B (2) were isolated from a liquid culture of Talaromyces aurantiacus. The structures of 1 and 2 were elucidated by IR, MS, 1D and 2D NMR spectra and comparison of the experimental and calculated electronic circular dichroism spectra. Additional known compounds (3–6) were also isolated. These compounds were tested for monoamine oxidase, acetylcholinesterase and PI3K inhibitory activity, but showed only weak activity.     

A new azaphilone from the entomopathogenic fungus Hypocrella sp.

This report describes the isolation of a new azaphilone, designated hypocrellone A (2), together with five known compounds (1, 3–6) from a submerged culture of the entomopathogenic fungus Hypocrella sp. (isolate WYTY-21). The absolute stereostructures of the two compounds (1 and 2) were elucidated based on 1D and 2D NMR spectroscopic and mass spectrometric data combined with the data from various chemical transformations. Hypocrellone A (2) and three (3–6) of the five known compounds were cytotoxic to hepatoma cells (cell line BEL-7404); IC₅₀ values ranged from 6.2 to 17.4 μM. At 200 μM, none of the six compounds was toxic to normal human liver cells (cell line HL-7702) or to normal human kidney epithelial cells (cell line HEK-293T).     

The Purified Siderophore from Streptomyces tricolor HM10 Accelerates Recovery from Iron-Deficiency-Induced Anemia in Rats

Iron-deficiency-induced anemia is associated with poor neurological development, including decreased learning ability, altered motor functions, and numerous pathologies. Siderophores are iron chelators with low molecular weight secreted by microorganisms. The proposed catechol-type pathway was identified based on whole-genome sequences and bioinformatics tools. The intended pathway consists of five genes involved in the biosynthesis process. Therefore, the isolated catechol-type siderophore (Sid) from Streptomyces tricolor HM10 was evaluated through an anemia-induced rat model to study its potential to accelerate recovery from anemia. Rats were subjected to an iron-deficient diet (IDD) for 42 days. Anemic rats (ARs) were then divided into six groups, and normal rats (NRs) fed a standard diet (SD) were used as a positive control group. For the recovery experiment, ARs were treated as a group I; fed an IDD (AR), group II; fed an SD (AR + SD), group III, and IV, fed an SD with an intraperitoneal injection of 1 μg Sid Kg⁻¹ (AR + SD + Sid1) and 5 μg Sid Kg⁻¹ (AR + SD + Sid5) twice per week. Group V and VI were fed an iron-enriched diet (IED) with an intraperitoneal injection of 1 μg Sid Kg⁻¹ (AR + IED + Sid1) and 5 μg Sid Kg⁻¹ (AR + IED + Sid5) twice per week, respectively. Weight gain, food intake, food efficiency ratio, organ weight, liver iron concentration (LIC) and plasma (PIC), and hematological parameters were investigated. The results showed that ~50–60 mg Sid L⁻¹ medium could be producible, providing ~25–30 mg L⁻¹ purified Sid under optimal conditions. Remarkably, the AR group fed an SD with 5 μg Sid Kg⁻¹ showed the highest weight gain. The highest feed efficiency was observed in the AR + SD + Sid5 group, which did not significantly differ from the SD group. Liver, kidneys, and spleen weight indicated that diet and Sid concentration were related to weight recovery in a dose-dependent manner. Liver iron concentration (LIC) in the AR + IED + Sid1 and AR + IED + Sid5 groups was considerably higher than in the AR + SD + Sid1 AR + SD + Sid5 groups or the AR + SD group compared to the AR group. All hematological parameters in the treated groups were significantly closely attenuated to SD groups after 28 days, confirming the efficiency of the anemia recovery treatments. Significant increases were obtained in the AR + SD + Sid5 and AR + IED + Sid5 groups on day 14 and day 28 compared to the values for the AR + SD + Sid1 and AR + IED + Sid1 groups. The transferrin saturation % (TSAT) and ferritin concentration (FC) were significantly increased with time progression in the treated groups associatively with PIC. In comparison, the highest significant increases were noticed in ARs fed IEDs with 5 μg Kg⁻¹ Sid on days 14 and 28. In conclusion, this study indicated that Sid derived from S. tricolor HM10 could be a practical and feasible iron-nutritive fortifier when treating iron-deficiency-induced anemia (IDA). Further investigation focusing on its mechanism and kinetics is needed.     

Two new metabolites of a marine endophytic fungus (No. 1893) from an estuarine mangrove on the South China Sea coast

The endophytic fungus No. 1893 was isolated from the dropper of Kandelia candel from an estuarine mangrove on the South China Sea coast. The ethyl acetate extract of the fermentation broth of this fungus strain exhibited cytotoxicity toward NCI4460 and Bel-7402, and high activities against Heliothis armigera (Hühner) and Sinergasilus spp. Two new lactones, 1893A (1) and B (2), together with 5-(p-hydroxybenzyl)hydantoin and two cyclodipeptides, cyclo-(Ser-Leu) and cyclo-(Phe-Gly), were isolated from the extract. Their structures were determined by spectroscopic experiments, including X-ray diffraction.     

Two new diterpenoids from the endophytic fungus Trichoderma sp. Xy24 isolated from mangrove plant Xylocarpus granatum

Two new harziane diterpenoids, named(9R,10R)-dihydro-harzianone(1) and harzianelactone(2), were isolated from the endophytic fungus Trichoderma sp. Xy24 by using various column chromatography techniques. Their structures were determined on the basis of extensive spectroscopic(HR-ESI-MS, 1D NMR, 2D NMR and CD) analyses. Among them, 1 was the reductive product of harzianone and 2 was the Baeyer–Villiger monooxygenase catalyzed oxidation product of harzianone. Compound 1 exhibited cytotoxic activity against He La and MCF-7 cell lines with IC_(50) values of 30.1 μmol/L and 30.7 μmol/L,respectively.     

Two new tremulane sesquiterpenes from a mangrove endophytic fungus,Coriolopsis sp. J5

Two new tremulane sesquiterpenes coriolopsin A (1) and coriolopsin B (2), together with two known ones conocenol C (3) and ceriponol E (4), were isolated from the fermentation extract of endophytic fungus Coriolopsis sp. J5 from Ceriops tagal. The structures and absolute configuration of compounds 1 and 2 were determined based on HR-ESI-MS and spectroscopic data (IR, UV, 1D, 2D NMR and X-ray crystallographic analysis).     

A new polyketide,penicillolide from the marine-derived fungus Penicillium sacculum

A new polyketide, penicillolide (1) was isolated from the fermentation broth of the marine-derived fungus Penicillium sacculum GT-308. Compound 1 is a polyketide with a unique carbon skeleton. The structure of this compound was established via extensive spectroscopic analyses including 1D-, 2D-NMR, and HRESI-MS.     

A new biphenyl derivative from an unidentified marine fungus E33

A new biphenyl derivative 3,5′-dihydroxy-4′,5-dimethoxy-2′-methyl-[1,1′-biphenyl]-2-carboxylic acid methyl ester (1), was isolated from the culture broth of a fungus isolated from the rhizosphere soil of mangrove root on the South China Sea. The structure of 1 was determined by comprehensive spectroscopic methods, primarily 2D NMR techniques. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 128–129, March–April, 2008.     

Two new triterpenoids from the fungus Diplodia cupressi

Abstract

One new pentanortriterpenoid, 23,24,25,26,27-pentanorlanost-7,9(11)-dien-3β,22-diol (1), one new triterpenoid, lanost-8-en-3β,22S,23S-triol (2), together with the known triterpenoid, 23,24,25,26,27-pentanorlanost-8-en-3β,22-diol (3), were obtained from culture of the fungus Diplodia cupressi associated with the moss Polytrichum commune. The structures of the new compounds were elucidated by extensive spectroscopic techniques including HR-ESIMS and 1?D and 2?D NMR experiments. The cytotoxicity of these compounds against human cancer cell lines (A549, Hep G2, Hepa 1c1c7, and Hela) was evaluated and compound 2 exhibited weak inhibitory activity with IC₅₀ value of 35.0?±?2.3?μM against the proliferation of the Hepa 1c1c7 cells.     

A new sesquiterpene from the entomogenous fungus Phomopsis amygdali

A new sesquiterpene, (+)-S-1-methyl-abscisic-6-acid (1), together with five known compounds, (+)-S-abscisic acid (2), fusicoccin J (3), 3α-hydroxyfusicoccin J (4), (R)-5-hydroxymethylmellein (5) and 4-hydroxyphenethyl acetate (6) was isolated from the fermentation extract of Phomopsis amygdali, an entomogenous fungus isolated from Call midge. Their structures were determined mainly by analysis of MS and NMR spectroscopic data. Compounds 1–6 were tested for antimicrobial activity against three plant pathogenic fungi: Gibberella zeae, Verticillium albo-atrum, and Fusarium nivale, and two bacteria: Escherichia coli and Pseudomonas aeruginosa 2033E. As a result, compounds 1–4 displayed antibacterial activity against Gram-negative P. aeruginosa 2033E, and the minimum inhibition concentration (MIC value) of 1–4 is 30 μg/mL, 58 μg/mL, 26 μg/mL, and 26 μg/mL, respectively.