p-Terphenyl alcohols from a marine sponge-derived fungus, Aspergillus candidus OUCMDZ-1051

In order to discover structurally new and bioactive conipounds from marine life,we studied the secondary metabolites of the marine-derived fungi associated with a marine sponge(XS-3)from the Xisha islands.As a result,4-O-methylcandidusin A(1),a new p-terphenyl alcohol,along with nine known analogs(2-10),were isolated and identified from the marine spongederived fungus Aspergillus candidus OUCMDZ-1051.The structures of these compounds were determined by analyzing spectroscopic data,especially ID and 2D NMR.The new compound 1 selectively inhibited the growth of the MDA-MB-46&BT474 and A431 human cancer cell lines with the IC_(50) values of 1.84,6.05 and 0.98 pmol/L,respectively.Compound 1 also displayed a selective antimicrobial activity against Escherichia coli with an MIC value of 27.3 pmol/L.The results indicated 4-O-methylcandidusin A(1)as a potential lead in the new drug discovery for triple negative breast cancer,invasive ductal breast cancer and epidermoid cancer.The antimicrobial metabolites also evidenced a clue for chemical defense of sponges by their associated microorganisms.

Production and purification of a bioactive substance against multi-drug resistant human pathogens from the marine-sponge-derived Salinispora sp.

Objective:To isolate,purify,characterize,elucidate structure and evaluate bioactive compounds from the sponge-derived Salinispora sp.FS-0034.Methods:The symbiotic actinomycete strain FS-0034 with an interesting bioactivity profile was isolated from the Fijian marine sponge Theonella sp.Based on colony morphology and obligatory requirement of seawater for growth,and mycelia morphological characteristics the isolate FS-0034 was identified as a Salinispora sp.The bioactive compound was identified by using various spectral analysis of ultraviolet,high resolution electrospray ionization mass spectroscopy,H nuclear magnetic resonance,correlated spectroscopy and heteronuclear multiple bond coherence spectral data.A minimum inhibitory concentration assay were performed to evaluate the biological properties of the pure compound against multi-drug resistant pathogens.Results:Bioassay guided fractionation of the ethyl acetate extract of the culture of Salinispora sp.FS-0034 by different chromatographic methods yielded the isolation of an antibacterial compound,which was identified as rifamycin W(compound 1).Rifamycin W was reported for its potent antibacterial activity against methicillin-resistant Staphylococcus aureus,wild type Staphylococcus aureus and vancomycin-resistant Enterococcus faecium and displayed minimum inhibitory concentrations of 15.62,7.80 and 250.00 μg/mL,respectively.Conclusions:The present study reported the rifamycin W from sponge-associated Salinispora sp.and it exhibited appreciable antibacterial activity against multi-drug resistant human pathogens which indicated that sponge-associated Actinobacteria are significant sources of bioactive metabolites.

Metabolites of Marine-derived Mangrove Endophytic Fungus #2492 from the South China Sea

Two metabolites （A and B） were isolated from the mycelium of mangrove endophytic fungus Stysanus like sp. （#2492） from the South China Sea. Their structures were identified by spectral data as N-（2-hydroxytetracosyl）-2-amino-1,3,4-trihydroxyoctadecane （A） and γ -stearolactone （B）. It is the first report that γ -stearolactone （B） is isolated from marine fungus as natural product.

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

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.

Eremophilane sesquiterenes from the marine fungus Penicillium sp.BL27-2

Six eremophilane sesquiterpenes were obtained from a marine fungus Penicillium sp. BL27-2. Their structures were elucidated as 3-acetyl-9, 7 （11）-dien-7a-hydroxy-8-oxoeremophilane （1）, 3-acetyl-13-deoxyphomenone （2）, Sporogen-AO 1 （3）, 7-hydro- xypetasol （4）, 8a-hydroxy-13-deo -xyphomenone （5） and 6-dehydropetasol （6） based on detailed NMR analysis. 1 was a new compound and 2 was obtained as a new natural compound. These compounds were assayed for their cytotoxic activity on P388, A549, HL60, BEL7402 and K562 cell lines by the MTT method. The assay results suggested the epoxide rings in eremophilane molecules were essential for their activity, and acetylation could enhance their activity.

Isolation and Neuroprotective Activity of Phenolic Derivatives from the Marine-Derived Fungus Penicillium janthinellum

A new phenolic compound, 6-(2-acetyl-3,5-dihydroxybenzyl)-4-hydroxy-3-methyl-2H-pyran-2-one(1), along with other six known phenolic derivatives(2-7), were isolated from the mangrove rhizosphere fungus Penicillium janthinellum HK1-6 cultured in potato dextrose broth medium containing 30 g L^(-1) of natural sea salt. The structure of the new compound(1) was elucidated by comprehensive analysis of spectroscopic data including 1D and 2D NMR spectra. The proposed biosynthetic pathway of compound 1 was also studied in this research. Interestingly, a brominated phenolic derivative, aryl bromide(compound 8), was obtained from this fungal strain cultured in medium containing 30 g L^-1 of NaBr instead of natural sea salt. Compound 8 is proposed as a new natural product and formed through bromination of compound 7 when the fungus was cultured with NaBr. The neuroprotective effect of compound 1 on oxygen-glucose deprivation(OGD)-induced injury was investigated in rat spinal cord astrocytes. MTT assay demonstrated that compound 1 can attenuate OGD-induced cell viability loss in rat spinal cord astrocytes.

A new nine-membdered lactone from a marine fungus Cladosporium sp.F14

A new nine-membered lactone,cladospolide E（1）,was isolated from a culture broth of a marine fungus Cladosporium sp.F14. The structure of compound 1 was determined on the basis of extensive spectroscopic analysis,including 1D and 2D NMR data.

Decumbenones A–C from marine fungus <i>Aspergillus sulphureus</i>as stimulators of the initial stages of development of agricultural plants

The effect of decumbenones A (1), B (2) and C (3) from the marine-derived strain of the fungus Aspergillus sulphureus on the growth of seedling roots of buckwheat, wheat, barley and corn at the concentration range 10﹣5 - 10﹣18 M was studied. It was shown that decumbenone B had a stimulatory effect on the growth of seedling roots of buckwheat, decumbenone A—on the growth of seedling roots of spring soft wheat, decumbenone C—on the growth of seedling roots of spring barley, decumbenone A, B and C —on the growth of seedling roots of corn. The stimulatory effect for some substances was shown at ultra-low concentrations 10﹣12 - 10﹣18 M. It is possible to recommend decumbenones A, B and C for studying in field conditions as growth factors of buckwheat, wheat, barley and corn.

Structural Determination of Three Sphingolipids from Two Marine-derived Mangrove Endophytic Fungal Strains

A set of three sphingolipids, N-2′-hydroxyplmitoyl-1-O-β-D-glucopyranosyl-9-methyl-4E, 8E-sphingadiene （A）, N-2′-hydroxyl-3′E-octadecenoyl-1-O-β-D-glucopyranosyl-9-methyl-4E, 8E-sphingediene （B） and N-palmitoyldihydrosphingosine （C）, were isolated from two marine-derived mangrove endophytic fungal strains （strains No. 1924 and 3893） from the South China Sea. Their structures were elucidated by 2D NMR and FABMS methods. It is the first time that these sphingolipids were separated and obtained from marine-derived mangrove endophytic fungus from the South China Sea.

Algicidal activities of secondary metabolites of marine macroalgal-derived endophytic fungi

Red tide occurrs frequently and causes signi?cant damage to the environment and human health. As a result, development of new effcient and environment friendly red-tide microalgae inhibitors has gained increasing attention in recent times. Algicolous endophytic fungi with unique habitats are promising sources for active agents owing to their abundant secondary metabolites and distinguished activities. In this study, the algicidal activities of 49 marine macroalgal-derived endophytic fungi against phytoplankton Alexandrium tamarense, Prorocentrum donghaiense, Heterosigma akashiwo, and Chattonella marina were examined using 96-well microplate. Four fungal strains, including Aspergillus wentii(pt-1), A. ustus(cf-42),and A. versicolor(dl-29, pt-20), exhibited potent algicidal activities. A total of 32 pure compounds isolated from these fungi were noted to possess dif ferent degrees of algicidal activities. Of those, 11 compounds comprising ?ve anthraquinones, two terpenoids, and four steroids showed high 24-h inhibition rates for the four red tide algae, with 24 h EC_(50) values ranging from 0.01 to 14.29 μg/mL. Among them, compound1(1,5-dihydroxy-3-methoxy-7-methylanthraquinone) presented the strongest activity against H. akashiwo,and could decrease its chlorophyll a(Chl a) and superoxide dismutase contents and increase the soluble protein, malondialdehyde, and peroxidase contents. These results suggested that the identi?ed anti-algal compound might inhibit the growth of red tide algae by weakening photosynthesis(reducing Chl a content),destroying cell membrane, and damaging the antioxidant system.

Uncommon N-Methoxyindolediketopiperazines from Acrostalagmus luteoalbus,a Marine Algal Isolate of Endophytic Fungus

Main observation and conclusion Four new N-methoxyindolediketopiperazines(acrozines D—G,1—4)and six known congeners(5—10)were purified from the organic extract of Acrostalagmus luteoalbus TK-43,which was a marine algal-derived fungus obtained from Codium fragile.Their structures were determined by interpretation of NMR and mass spectroscopic data.The structures of compounds 1,2,and 4 including their absolute configurations were confirmed by single-crystal X-ray diffraction,while the absolute configuration of compound 3 was elucidated by comparative analysis of ECD and TDDFT-ECD calculations.Compounds 1—4,with a unique methoxy substitution at N-2,were rarely discovered among indolediketopiperazine alkaloids.All these compounds were evaluated for antimicrobial activities against human-and aquatic-pathogenic bacteria and plant-related pathogenic fungi,with compounds 5 and 7 exhibiting potent activity against Edwardsiella icataluri(MIC=3 and 5μmol/L,respectively),while compound 9 displayed a broad spectrum of antibacterial activities.The four new compounds were further tested for anti-acetylcholinesterase(AChE)properties,and compound 3 exhibited inhibitory activity with IC_(50)value of 8.4μmol/L.

Four new steroids from the marine soft coral-derived fungus Penicillium sp. SCSIO41201

Penicildiones A-D(1-4), four new steroids derivatives together with three known compounds including 16α-methylpregna-17α,19-dihydroxy-(9,11)-epoxy-4-ene-3,18-dione-20-acetoxy(5), stachybotrylactone B(6) and stachybotrin(7) were isolated from the soft coral-derived fungus Penicillium sp. SCSIO41201, cultured in the 1% NaCl PDB substrate. Their structures were determined through spectroscopic methods and X-ray crystallography. Biological evaluation results revealed that 6 exhibited significant cytotoxic activity against HL-60, K562, MOLT-4, ACHN, 786-O, and OS-RC-2 cell lines with IC50 values of 5.23, 4.12, 4.31, 23.55, 7.65 and 10.81 μmol·L-1, respectively, while other compounds showed weak or no cytotoxicity at 50 μmol·L-1.

Fusarielin E,a new antifungal antibiotic from Fusarium sp.

A new antifungal antibiotic, fusarielin E, was isolated from the marine-derived fungus Fusarium sp. Its structure was established on the basis of various NMR spectroscopic analyses and HR-FAB-MS. Fusarielin E displayed significant biological activity against Pyricularia oryzae.

Mycochemistry of marine algicolous fungi

Marine algicolous fungi refer to the fungi inhabiting or associated with marine algae,which have attracted a great attention for natural product researchers due to their chemical diversity and biological activity during the past two decades.Up to the end of 2014,a total of 366 new natural products,including polyketides,terpenoids,polyketide-terpenoids,peptides,alkaloids,and shikimate derivatives,have been characterized from them.Among these metabolites,240 compounds feature cytotoxic,antibacterial,antifungal,antimicroalgal,zooplankton-toxic,antiprotozoal,antioxidative,enzyme-modulatory,and/or some other activities.This review gives a comprehensive coverage of both chemical and biological aspects of the secondary metabolites from marine algicolous fungi.

Structures and Antiviral Activities of Butyrolactone Derivatives Isolated from Aspergillus terreus MXH-23

A new butyrolactone derivative,namely butyrolactone Ⅷ （1）,and six known butyrolactones （2-7） were separated from the ethyl acetate （EtOAc） extract of the fermentation broth of a fungus,Aspergillus terreus MXH-23.The chemical structures of these metabolites were identified by analyzing their nuclear magnetic resonance （NMR） and mass spectrometry （MS）.Known butyrolactone derivatives contain an α,β-unsaturated γ-lactone ring with α-hydroxyl and y-benzyl,and butyrolactone Ⅷ （1） was the first butyrolactones contains α-benzyl and γ-hydroxyl on α,β-unsaturated lactone ring.All of the butyrolactone derivatives were tested for their anti-influenza （H 1N 1） effects.Derivatives 4 and 7 showed moderate antiviral activities while the newly-identified,derivative 1,did not.

A cytotoxic pyrrolidinoindoline diketopiperazine dimer from the algal fungus Eurotium herbariorum HT-2

A new cytotoxic pyrrolidinoindoline diketopiperazine dimer, cristatumin E （1）, was isolated from the fermentation broth of the algal fungus Eurotium herbariorum HT-2 associated with the marine algae, Enteromorpha prolifera. The structure was determined by spectroscopic analyses and Marfey＇s amino acid analysis. Cristatumin E （1） showed cytotoxicity against K562 tumor cell line and antibacterial activity against Enterobacter aerogenes and Escherichia coli with IC50 and MIC values of 8.3, 44.0 and 44.0 μmol/L, respectively.

Removal of dyes from wastewater by growing fungal pellets in a semi-continuous mode

To increase the efficiency of dye removal from wastewater using mycelial pellets, a bubble column reactor with a simple structure was designed and efficiently used to remove dyes from solution containing dyes. The mycelial pellets were prepared by marine fungus Aspergillus niger ZJUBE-1. Eight dyes were tested as dye targets for the adsorption capacity of mycelial pellets and good removal results were obtained. Eriochrome black T was selected as a model dye for characterizing the adsorption processes in detail. The measurement results of Zeta potential and FT- IR analysis indicate that the electrostatic attraction may play a key role in the biosorption process. The bubble column reactor was utilized to study the batch dye-removal efficiency of mycelial pellets. A re-culture process between every two batches, which was under non-sterile condition, successfully enhanced the utilization of mycelium bio- mass. The dye removal rate is 96.4% after 12 h in the first batch and then decreases slowly in the following batches. This semi-continuous mode, which consists of commutative processes of dye-removal and re-culture, has some outstanding advantages, such as low power consumption, easy operation, high dye removal rate, and efficient biomass utilization.