Studies on the secondary metabolites from marine fungus 09-1-1-1
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Objective To search for novel antifungal structures produced by marine fungus.Methods Using the Pyricularia oryzae (P.oryzaae) bioassay method to screen marine fungi led to the isolation of marine fungus 09-1-1-1.Active metabolites were isolated from the broth of the marine fungus 09-1-1-1.Results Two compounds were extracted from the mycelium and their structures were elucidated by various spectroscopic methods as 3a,12c-dihydro-8-hydroxy-6-methoxy-7H-furo\furo\xanthen-7-one(Ⅰ,sterigmatocystin) and 1,3,6,8-tetrahydroxy-2-(1-hydroxyhexyl)anthraquinone(Ⅱ,averantin).Conclusion The P.oryzae bioassay was a cheap,quick and convenient method for the screening of bioactive substances from marine fungi.Compound Ⅱ showed potent inhibitory activity to the mycelia of P.oryzae.The MIC of compound Ⅱagainst P.oryzae was 1.6 μg·mL~(-1).Keywords:
Pyricularia
Sterigmatocystin
Marine fungi
Aspergillus oryzae
Secondary metabolite
Aspergillus versicolor
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To study the metabolites of marine fungus Alternalia sp.Compounds were separated by column chromatography and their structures were elucidated by means of chemical and spectral analysis.Six compounds were isolated from the ethyl acetate and n-butanol extracts of the fermentation of marine fungus Alternalia sp. Their structures were elucidated as p-benzyloxy-phenol ( I ), p-hydroxy phenyl ethylamine( II ), 3-hydroxymethyl-8-hydroxyl-pyrrolopiperazine-2, 5-dione ( III ), 3-isobutyl-6-secbutyl-piperazine-2, 5-dione (IV), 5alpha, 8alpha-epidioxy-ergosta-6, 22-diene-3beta-ol (V), 3beta-hydroxxy-cholesta-5-ene (VI).Compounds I , II, III, IV have the activity of inducing morphological deformation of mycelia germinated from conidia of Pyricularia oryzae. Compounds I , II , III were isolated from the genus Alternalia for the first time.
Pyricularia
Hydroxymethyl
Ethylamine
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Prenylated Diphenyl Ethers from the Marine Algal-Derived Endophytic Fungus Aspergillus tennesseensis
Considerable attention has been paid to marine derived endophytic fungi, owing to their capacity to produce novel secondary metabolites with potent bioactivities. In this study, two new compounds with a prenylated diphenyl ether structure—diorcinol L (1) and (R)-diorcinol B (2)—were isolated from the marine algal-derived endophytic fungus Aspergillus tennesseensis, along with seven known compounds: (S)-diorcinol B (3), 9-acetyldiorcinol B (4), diorcinol C (5), diorcinol D (6), diorcinol E (7), diorcinol J (8), and a dihydrobenzofuran derivative 9. Their structures were elucidated by extensive NMR spectroscopy studies. Compound 2 represents the first example of an R-configuration in the prenylated moiety. All these isolated compounds were examined for antimicrobial and cytotoxic activities. Compounds 1–9 exhibited antimicrobial activities against some human- and plant-pathogenic microbes with MIC values ranging from 2 to 64 μg/mL. Moreover, compound 9 displayed considerable inhibitory activity against the THP-1 cell line in vitro, with an IC50 value of 7.0 μg/mL.
Moiety
Marine fungi
Diphenyl ether
Anthraquinones
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A new anthraquinone compound, 5-acetyl-2-methoxy-1,4,6-trihydroxy-anthraquinone (1), together with four known naphthoquinones (2-5), were isolated from the culture of the mangrove fungus (No. b77). All the isolated compounds (1-5) and the acetyl derivative (1a) were established by comprehensive analysis of the spectral data, especially 1D- and 2D-NMR (HMQC and HMBC) spectra. In the primary bioassays, compound 3 showed strong inhibitory effects on the growth of hepG2 and hep2 cells, with IC(50) values of 1.0 and 2.5 microg mL(-1), respectively.
Anthraquinones
Derivative (finance)
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Objective The secondary metabolites of marine fungus zp6 and their antibacterial activities were studied.Methods The compounds were isolated by means of silica gel column and HPLC chromatography.Their structures were determined on the basis of physicochemical evidences and spectral methods.In order to evaluate the antifungal activity of the compounds,filter paper method was used.Results Eight compounds were isolated from the fermentation liquid extracted by ethyl acetate,and were identified as(22E)-3β,5α,9α-trihydroxy-ergosta-7,22-dien-6-one(1),5α,8α-epidioxy-ergosta-6,22-dien-3β-ol(2),erythritol(3),adenosine(4),(24R)-ergosta-7,22-diene-3β,5α,6β-trio1(5),arabinitol(6),9-octadecenoic acid(7),4-acetoxybenozic acid(8).Conclusion Compounds 1 and 5 showed antifungal activities.
Erythritol
Filter paper
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Four known metabolites have been isolated from the culture extracts of three 9F series marine fungi derived from Palau Islands. Their structures have been identified by spectral methods as trans-dehydrocurvularin (1),terrein(2),paxilline(3)and citreopyrone(4). The MIC of 1～4 against Pyricularia oryzae P-2b were 10,100,1.56,3.12 μg/mL. Compounds 1 were obtained from the cultures of marine fungi for the first time.
Pyricularia
Isolation
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The new anthraquinone derivative, 6,8-di-O-methylaverantin (1), together with six known congeners (2-7), were characterized from a culture extract of the marine algous fungus, Aspergillus versicolor EN-7. Their structures were elucidated by spectroscopic methods. A bioassay showed compounds 1, 2 and 5 to have weak inhibition against Escherichia coli, while compound 5 also displayed weak inhibition against Staphylococcus aureus.
Aspergillus versicolor
Anthraquinones
Derivative (finance)
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Objective To investigate the secondary metabolites and their bioactivities of a soft coral-derived fungus.Methods Under the guidance of bioassay,column chromatography on silica gel and Sephadex LH-20,and semi-preparative HPLC were used to isolate and purify the metabolites from the fermentation products of Aspergillus versicolor(ZJ-2008015),a fungus obtained from a soft coral Sarcophyton sp.collected from the South China Sea.The structures of the isolated compounds were identified by spectroscopic analysis including NMR and MS,and by comparison with the data of literature.The bioactivities of the compounds were evaluated with brine shrimp lethality and antibacteria models.Results Six compounds were isolated from the EtOAc extracts of the culture broth and the mycelia of A.versicolor(ZJ-2008015),and their structures were identified as(+)-sydonic acid(1),expansol G(2),(+)-sydowic acid(3),cyclo(L-Trp-L-Phe)(4),homodimeric WIN 64821(5),and ergosta-6α-hydroxy-4,22-dien-3-one(6).Conclusion The bisabolane sesquiterpene compounds 1~3 exhibited potent antibacterial activity against Staphylococcus albus and Staphylococcus aureus.
Aspergillus versicolor
Brine shrimp
Sephadex
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Abstract New compounds asporyzin A (I), asporyzin B (II) and asporyzin C (III), together with three known indoloditerpenes are isolated from an endophytic fungus Aspergillus oryzae.
Aspergillus oryzae
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Objective To isolate and identify the antitumor components of the deep-sea derived fungus Aspergillus sp.CXCTD-06-6a.Methods The extracts of the fungus were purified by solvent extraction,column chromatography and preparative HPLC guided by the bioassay results.Their structures were established by physicochemical properties and spectral analysis.Their proliferation inhibition activities were evaluated by MTT method.Results Five compounds(1~5) were isolated and identified as averufin(1),averufanin(2),ergosterol peroxide(3),versiol(4) and 5-hydroxy-2-methoxybenzoic acid(5),respectively.Compounds 1 and 3 showed activities against P388 and HeLa cell lines.It's the first time to report the proliferation inhibition evaluation of compounds 2 and 5 on P388,A549 and HeLa cells,and compounds 1 and 4 on P388 cells.Conclusion Deep sea is a rich resource for discovery of new active compounds.
HeLa
Ergosterol
Marine fungi
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Marine-derived fungi are a treasure house for the discovery of structurally novel secondary metabolites with potential pharmaceutical value. In this study, a pair of new nor-bisabolane derivative enantiomers (±)−1 and two new phthalides (4 and 5), as well as four known metabolites, were isolated from the culture filtrate of the marine algal-derived endophytic fungus Penicillium chrysogenum LD-201810. Their structures were established by detailed interpretation of spectroscopic data (1D/2D NMR and ESI-MS). The optical resolution of compound (±)−1 by chiral HPLC successfully afforded individual enantiomers (+)−1 and (−)−1, and their absolute configurations were determined by TDDFT-ECD calculations. Compound (±)−1 represents the first example of bisabolane analogs with a methylsulfinyl substituent group, which is rare in natural products. All of the isolated compounds 1–7 were evaluated for their cytotoxic activity against A549, BT-549, HeLa, HepG2, MCF-7, and THP-1 cell lines, as well as for antifungal activity against four plant pathogenetic fungi ( Alternaria solani , Botrytis cinerea , Fusarium oxysporum , and Valsa mali ). Compound 2, a bisabolane-type sesquiterpenoid, was shown to possess excellent activity for control of B. cinerea with half-maximal inhibitory concentration (IC 50 ) of 13.6 μg/mL, whereas the remaining investigated compounds showed either weak or no cytotoxic/antifungal activity in this study.
Penicillium chrysogenum
Alternaria solani
HeLa
Absolute Configuration
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