ABSTRACT
Three new mycophenolic acid derivatives, penicacids E-G (1-3), together with three known analogues, mycophenolic acid (4), 4'-hydroxy-mycophenolic acid (5) and mycophenolic methyl ester (6), were isolated from a marine-derived fungus Penicillium parvum HDN17-478 from a South China Sea marine sediment sample. The structures of compounds 1-3 were elucidated by HRMS, NMR, and Mosher's method. Among them, compounds 1 and 2 were the first examples of mycophenolic acid analogs with a double bond at C-3'/C-4' position. The cytotoxicity of 1-6 was evaluated against the HCT-116, BEL-7402, MGC-803, SH-SY5Y, HO-8910 and HL-60 cell lines, and compounds 4 and 6 showed potent cytotoxicity with IC
ABSTRACT
Objective: To study the secondary metabolites from the fermentation broth of marine-derived fungus Aspergillus sp. SCS-KFD66. Methods: The constituents were isolated and purified by silica gel, Sephadex LH-20 column chromatography and HPLC methods. The structures of the compounds were identified by spectral data analysis. The DPPH radical scavenging, acetylcholinesterase and α-glucosidase inhibitory activities of compounds were evaluated by DPPH method, Ellman colorimetric method and PNPG method, respectively. The inhibitory effect and the minimal inhibitory concentration (MIC) of compounds on Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Listeria monocytogenes were tested using 96-well microtiter plates method. Results: A total of 13 compounds were isolated from the fermentation broth of marine-derived fungus Aspergillus sp. SCS-KFD66 and identified as 3-epi-trans-4-hydroxylinalool 3,6-oxide (1), trans-4-hydroxylinalool 3,6-oxide (2), aloe emodin (3), emodin (4), citreorosein (5), protocatechualdehyde (6), 2,5-dihydroxybenzaldehyde (7), methyl 4-hydroxyphenylacetate (8), 4-hydroxybenzoic acid (9), 4-hydroxyphenylacetic acid (10), 2-(4-hydroxyphenyl) ethanol (11), (E)-p-hydroxycinnamic acid (12) and (E)-ferulic acid (13), respectively. Compounds 1, 6, 7 and 9-13 showed DPPH radical scavenging activities; Compounds 4 and 6 showed acetylcholinesterase inhibitory activity; Compounds 6 and 7 exhibited inhibitory activity against α-glucosidase. Compound 4 has inhibitory activity against S. aureus and B. subtilis with the MIC values of 16 μg/mL and 64 μg/mL, respectively. Compound 6 showed inhibitory activity against E. coli, B. subtilis and L. monocytogenes, with MIC values of 64, 128 and 128 μg/mL, respectively. Conclusion: Twelve known compounds and one new compound were isolated. Compound 1 is a new compound named as aspergfuranol.
ABSTRACT
OBJECTIVE: To study the secondary metabolites of marine-derived fungus Aspergillus fumigatus YK-7. METHODS: The compounds were isolated by several column chromatographic techniques, including silica gel, ODS, Sephadex LH-20 column chromatography, and HPLC, and their structures were identified on the basis of physicochemical properties and spectroscopic analysis. Trypan blue and MTT methods were applied for determining the effects of the compounds on proliferation of cancer cells in vitro. RESULTS: Ten compounds were obtained, and their structures were identified as pseurotin A (1), pseurotin A1(2), 14-norpseurotin A (3), FD-838 (4), demethoxyfumitremorgin C (5), 9β-hydroxyverruculogen TR-2 (6), 6-methoxyspirotryprostatin B (7), spiro[5H, 10H-dipyrrolo[1, 2-a:1', 2'-d]pyrazine-2-(3H), 2'-[2H]indole]-3', 5, 10(1'H)-trione (8), terezine D (9), and 14-hydroxyterezine D (10). CONCLUSION: Compounds 3, 6, 7, 9, and 10 are isolated from marine-derived fungus Aspergillus fumigatus for the first time. Compounds 1-4 exhibite moderate antiproliferative activity against selected cancer cell lines in vitro.
ABSTRACT
Two new azaphilone derivatives containing 1,3-dioxolane moiety, penidioxolanes A (1) and B (2), were isolated from marine-derived fungus Penicillium sp. KCB12C078, together with four known compounds (3-6) by chemical investigation. Compounds 1 - 6 were isolated by combination of silica gel, ODS column chromatography and preparative HPLC. Their structures were determined by analysis of spectroscopic data including 1D-, 2D-NMR, and MS techniques. The isolates were evaluated against cancer cell growth inhibition effects and antimicrobial activity.
Subject(s)
Chromatography , Chromatography, High Pressure Liquid , Fungi , Penicillium , Silica GelABSTRACT
Two new thiodiketopiperazines (TDKPs), designated graphiumins I (1) and J (2), were isolated from the culture broth of the marine-derived fungus Graphium sp. OPMF00224 by solvent extraction, silica gel column chromatography, and HPLC. Their absolute structures were elucidated by spectroscopic analyses (1D and 2D NMR data, ROESY correlations, and CD data) and chemical methods. They were found to be structurally rare TDKPs with a phenylalanine-derived indolin substructure. Compounds 1 and 2 inhibited yellow pigment production by methicillin-resistant Staphylococcus aureus (MRSA) with IC50 values of 63.5 and 76.5 microg/ml, respectively, without inhibiting its growth, even at 250 microg/ml.
Subject(s)
Chromatography , Chromatography, High Pressure Liquid , Fungi , Inhibitory Concentration 50 , Methicillin-Resistant Staphylococcus aureus , Silica GelABSTRACT
OBJECTIVE: To study the secondary metabolites of marine-derived fungus Penicillium sacculum. METHODS: The compounds were separated by several column chromatographic techniques, and their structures were elucidated by means of physico-chemical properties and spectral data. Trypan blue exclusion assay and MTT method were used to test the anti-tumor activities. RESULTS: Ten compounds were isolated from the fermentation broth and mycelium. Their structures were identified as(R)-1, 3-di-hydro-6-methoxy-3-methylisobenzofuran-4, 5-diol(curvulol)(1), griseofulvin(2), 1, 6-dihydroxy-3-methoxy-8-methylxanthone(3), 1-hydroxy-3-methylxanthone(4), 1, 3, 6-trihydroxy-8-methylxanthone(5), 1, 8-dihydroxy-3-methylanthraquinon(6), 1, 3, 5-trihy-droxy-7-methylanthraquinone(7), citreorosein(8), adenine(9) and thymine(10). Among them, compounds 1 and 3 showed respectively potent and moderate growth inhibitory activities against human leukemia HL-60 cells. CONCLUSION: Compounds 1 and 4 were isolated for the first time from the genus of marine-derived fungus. The 1H-NMR and 13C-NMR signals of compound 1 were assigned for the first time. Compounds 1 and 3 have anti-tumor activities. Copyright 2012 by the Chinese Pharmaceutical Association.
ABSTRACT
Anti-tyrosinase assay guided isolation of marine-derived fungus Botrytis sp.led to separation of three ?-pyrone compounds.The structures of these compounds were elucidated by various physicochemical analytical methods.The bioactivities of these ?-pyrone derivatives were evaluated in terms of anti-tyrosinase activity.By correlating the bioactivities of these compounds with their structures,it concluded that the ?-pyrone with pentyl group gives highest anti-tyrosinase activity.