Emerixanthone E,a new xanthone derivative from deep sea fungus Emericella sp SCSIO 05240

The marine fungus Emericella sp was isolated from the deep sea sediments. The fungus was identified by its morphology and ITS region. A new emerixanthone E (1) together with four (2–5) known emodin derivatives were isolated from the metabolites of the fungus Emericella SCSIO05240. The structures were elucidated on the basis of NMR spectroscopic analysis and mass spectrometry. The biological properties of those compounds (1–5) were explored for antimicrobial, antifungal and antitumor activity.     

Isochromanes from Aspergillus fumigatus,an endophytic fungus from Cordyceps sinensis

Four previously undescribed isochromanes were isolated from the fermentation broth of an endophytic fungus Aspergillus fumigatus, which was obtained from the fruiting body of Cordyceps sinensis. Their structures were elucidated through extensive spectroscopic analyses. One racemic isochromane was further purified by chiral HPLC to yield a pair of enantiomers and their absolute configurations were determined by quantum chemical ECD calculations. These isolated compounds were evaluated for cytotoxicity against two cell lines (MV4-11 and MDA-ME-231) and the result showed that compounds 1a and 2 exhibited moderate growth inhibition against MV4-11 cell line.     

Aspergillolide,a new 12-membered macrolide from sea cucumber-derived fungus Aspergillus sp. S-3-75

Abstract

A new 12-membered macrolide, aspergillolide (1), along with nine known compounds (2–10), were isolated from the fungus Aspergillus sp. S-3-75 associated with the sea cucumber Holothuria nobilis Selenka. The structure and absolute stereochemistry of 1 were elucidated on the basis of extensive spectroscopic methods and single crystal X-ray diffraction analysis.     

A new diketopiperazine derivative from a deep sea-derived Streptomyces sp. SCSIO 04496

A new diketopiperazine (DKP) derivative, (6R,3Z)-3-benzylidene-6-isobutyl-1-methyl piperazine-2,5-dione (1), as well as five known DKPs 2–6 was isolated from a deep sea-derived Streptomyces sp. SCSIO 04496. The structure of 1 was elucidated using a combination of 1D and 2D NMR, HR-ESI-MS and chiral-phase HPLC techniques. Compounds 1–6 did not show cytotoxic activity at a concentration of 100 μM in bioactivity assay.     

A mycophenolic acid derivative from the fungus Penicillium sp. SCSIO sof101

Abstract

Mycophenolic acid (MPA) is a group of metabolite derived from several species of Penicillium, which shows potent bioactivity. In this study, a new derivative of MPA compound named penicacid D (1), was isolated from the marine derived fungus Penicillium sp. SCSIO sof101, along with seven known compounds (2-8). Their structures were elucidated based on the HR-ESI-MS and NMR data. Moreover, the ¹H and ¹³C NMR data of compound 2 and the ¹³C NMR data of compound 3 are reported. Compounds 1, 4 and 6 exhibited weak activities against Escherichia coli (clinical isolation number 100385570) and Acinetobacter baumannii (clinical isolation number 100069).     

New alkaloids and isocoumarins from the marine gorgonian-derived fungus Aspergillus sp. SCSIO 41501

Abstract

Two new β-carboline alkaloids, aspergillspins A-B (1–2), three new quinolone alkaloids, aspergillspins C-E (3–5), and two new isocoumarins, aspergillspins F-G (6–7), together with four known alkaloids were isolated from the marine gorgonian-derived fungus Aspergillus sp. SCSIO 41501. Their structures were identified by spectroscopic analysis, and the absolute configurations of several chiral carbons in 2 and 3 were further established by quantum chemical calculations of the electronic circular dichroism (ECD) spectra. Their cytotoxic and antibacterial activities were also evaluated.     

Discovery of a new biphenyl derivative by epigenetic manipulation of marine-derived fungus Aspergillus versicolor

Cultivation of the marine-derived Aspergillus versicolor MCCC 3A00080 with the addition of a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), significantly enhanced the diversity of secondary metabolites. From the culture treated, a new biphenyl derivative, named versiperol A (1), along with two known compounds, 2,4-dimethoxyphenol (2) and diorcinol (3) were isolated. The structures of 1–3 were established based on spectroscopic analysis and comparison with literature data. Among the isolates, versiperol A (1) exhibited modest inhibition of Staphylococcus aureus growth with MIC value of 8 μg/mL.     

A new naphthoquinoneimine derivative from the marine algal-derived endophytic fungus Aspergillus niger EN-13

Cultivation of an endophytic fungus Aspergillus niger EN-13 that was isolated from the inner tissue of the marine brown alga Colpomenia sinuosa resulted in the characterization of a new naphthoquinoneimine derivative,namely,5,7-dihydroxy-2-[1-(4- methoxy-6-oxo-6H-pyran-2-yl)-2-phenylethylamino]-[1,4]naphthoquinone.The structure of the new compound was established on the basis of various NMR spectroscopic analyses including 2D NMR techniques,EI-MS,and HR-ESI-MS.This compound displayed moderate antifungal activity.     

Ascomycotin A,a new citromycetin analogue produced by Ascomycota sp. Ind19F07 isolated from deep sea sediment

A new citromycetin analogue, ascomycotin A (1), together with eight known compounds, wortmannilactone E (2), orcinol (3), orsellinic acid (4), isosclerone (5), (3R,4S)-( ? )-4-hydroxymellein (6), diorcinol (7), chaetocyclinone B (8) and 2,5-dimethoxy-3,6-di(p-methoxypheny1)-1,4-benzoquinone (9), was isolated from the fungal strain Ascomycota sp. Ind19F07, which was isolated from the deep sea sediment of the Indian Ocean. The structures of the compounds were established by spectroscopic data including 1D and 2D NMR and HR-ESI-MS. Compounds (1–9) were evaluated for antibacterial activity.     

Versicorin,a new lovastatin analogue from the fungus Aspergillus versicolor SC0156

A new lovastatin analogue versicorin (1), together with three related compounds, decumbenones A (2) and B (3) and versiol (4), were isolated from mycelial solid cultures of Aspergillus versicolor SC0156. Their structures were elucidated on the basis of MS data and NMR spectroscopic analysis. The new compound versicorin (1) possesses a hexahydro-2H-naphtho[1,8-bc]furan moiety, which is a rare type of the lovastatin-analogous compounds. A hypothetical biosynthetic pathway for compounds 1–4 was proposed.     

A novel cyclic dipeptide from deep marine-derived fungus Aspergillus sp. SCSIOW2

A novel cyclic dipeptide, 14-hydroxy-cyclopeptine (1), was purified from a deep sea derived fungal isolate identified as an Aspergillus sp. The structure was elucidated by detailed spectroscopic analyses using 1D and 2D NMR experiments and high resolution mass spectrometry. The absolute configuration of the amino acid was determined by Marfey's method. Two conformational isomers of 1 were established by ROE analyses. 1 inhibited nitric oxide production with IC₅₀ values at 40.3 μg/mL in a lipopolysaccharide and recombinant mouse interferon-γ -activated macrophage-like cell line, RAW 264.7 and showed no cytotoxic effect in the tested dose range up to 100 μg/mL.     

Aspergilolide,a steroid lactone produced by an endophytic fungus Aspergillus sp. MBL1612 isolated from Paeonia ostii

A new steroid lactone aspergilolide (1), and nine known compounds helvolic acid (2), verruculogen (3), tryprostatin B (4), 13-oxofumitremorgin B (5), fumitremorgin C (6), demethoxy fumitremorgin C (7), terezine D (8), aszonalenin (9), 12, 13-dihydroxy-fumitremorgin C (10) from cultures of the endophytic fungus Aspergillus sp. MBL1612. Their chemical structures were determined by a series of extensive spectroscopic methods. All of the compounds were isolated from this genus for the first time. The cytotoxicity against five human cancer cell lines of new compound were detected.     

New asymmetrical bispyrrolidinoindoline diketopiperazines from the marine fungus Aspergillus sp. DX4H

Known diketopiperazine WIN 64821 and its asymmetric stereoisomers (1–3) had been isolated from the culture broth of a marine gut fungus Aspergillus sp. DX4H. The planar and stereochemistry for new compounds were determined by a suite of techniques including mass, NMR and CD spectra together with Marfey’s method. Their inhibitory activity against PC3 cell line had been tested.     

A new lumazine peptide penilumamide E from the fungus Aspergillus terreus

A new rare lumazine peptide, penilumamide E (1), together with 13 known compounds (2–14) were isolated from the fungus Aspergillus terreus. Their structures were identified by spectroscopic techniques. The relative configuration of 1 was confirmed by single-crystal X-ray diffraction analysis. Compound 10 exhibited antimalarial activity against Plasmodium falciparum with IC₅₀ values of 2.83 μg/mL. Compounds 4 and 6 showed weak cytotoxicity against cholangiocarcinoma (CCA) cell lines. In addition, 4 and 11 exhibited weak cytotoxicity against human hepatoma cell line.     

A new cyclohexenone from the tin mine tailings-derived fungus Aspergillus flavus YIM DT 10012

A new cyclohexenone, named phomaligol D (1), together with two known compounds, kojic acid (2) and phomaligol A (3) were isolated from the tin mine tailings-derived fungus Aspergillus flavus YIM DT 10012. Their structures were elucidated by detailed analysis of spectroscopic data.     

Terrenolide S,a new antileishmanial butenolide from the endophytic fungus Aspergillus terreus

Terrenolide S, a new butenolide derivative (6), together with six known compounds: (22E,24R)-stigmasta-5,7,22-trien-3-β-ol (1), stigmast-4-ene-3-one (2), stigmasta-4,6,8(14),22-tetraen-3-one (3), terretonin A (4), terretonin (5) and butyrolactone VI (7) have been isolated from the endophytic fungus Aspergillus terreus isolated from the roots of Carthamus lanatus (Asteraceae). Their structures were established by extensive spectroscopic analyses (1D, 2D NMR and HRESIMS), as well as optical rotation measurement and comparison with literature data. Compound 1 displayed a potent activity towards methicillin-resistant Staphylococcus aureus (MRSA) and Cryptococcus neoformans with IC₅₀ values of 2.29 and 10.68 µM, respectively. Moreover, 1, 2 and 6 exhibited antileishmanial activity towards Leishmania donovani with IC₅₀ values of 11.24, 15.32 and 27.27 µM, respectively and IC₉₀ values of 14.68, 40.56 and 167.03 µM, respectively.     

A new furan derivative from an endophytic Aspergillus flavus of Cephalotaxus fortunei

A new furan derivative named 5-acetoxymethylfuran-3-carboxylic acid (2), together with a known furan compound, 5-hydroxymethylfuran-3-carboxylic acid (1), were isolated from the fermentation of Aspergillus flavus, endophytic fungi in Cephalotaxus fortunei. The structures of 1 and 2 were elucidated by NMR, IR, UV and MS data, as well as compared with literature data. The compounds 1 and 2 exhibited potent antibacterial activity against Staphylococcus aureus with MIC values of 31.3 and 15.6 μg/mL, respectively. The compound 2 showed moderate antioxidant activity.     

A new pyrone derivative from an endophytic Aspergillus tubingensis of Lycium ruthenicum

A new pyrone named 6-isovaleryl-4-methoxy-pyran-2-one (1), along with three known pyrone compounds, rubrofusarin B (2), asperpyrones A (3) and campyrone A (4), was isolated from fermentation of Aspergillus tubingensis in Lycium ruthenicum. Their structures were confirmed by spectroscopic techniques, such as IR, NMR and HRESI-MS. Compound 2 indicated strong inhibitory activity against Escherichia coli, with MIC value of 1.95 μg/mL.     

Sphingofungins G and H: new five-membered lactones from Aspergillus penicilliodes Speg.

Two new sphingofungins G (1) and H (2) with a five-membered lactone ring were identified from the solid-state fermentation of Aspergillus penicilliodes Speg., a dominant microorganism isolated previously from the post-fermentation of ripe Pu-er tea, together with six known metabolites. Their structures were elucidated by extensive spectroscopic methods. All of them were isolated from the mycelia culture of A. penicilliodes for the first time. The known compound, trypacidin, exhibited potent cytotoxities against five human cancer cell lines, e.g. myeloid leukemia HL-60, lung cancer A-549, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480, with IC₅₀ values of 0.55, 11.45, 10.95, 3.58, and 3.49 μM, resp., while cisplatin as the positive control, with IC₅₀ values of 8.63, 24.15, 21.99, 27.29, and 23.61 μM, resp.