Secondary Metabolites From Three Marine Fungi

In recent years, more and more people have begun to pay close attention to th e study of secondary metabolites of marine microorganisms, because they can produ ce many unique structures which may have good biological activity. Due to various reasons and conditions, the study on marine chemistry and metabolism of microorga nism started relatively later. From 1988, the study of the secondary metabolites of marine microorganisms had begun, to 2002,only 270 new compounds from marine microorganisms were discovered. But relatively rapid development has happened in r ecent years, in 2009 alone, 273 new compounds were isolated from the marine micr oorganisms. The secondary metabolites of marine fungi are the important part of me tabolites from marine microorganisms. The metabolites of marine fungi are varied. S uch as terpenoids, peptides, alkaloids, esters. In this paper, different types of compo unds were also isolated from the metabolites of marine fungi and some of them are novel.This thesis introduced the study on the marine fungi Pseudallescheria boydii.,Sc edosporium minutisporum.,Fusarium sp and their metabolites.17 compounds consistin g of three new compounds and fifteen known compounds were isolated from mediu m of Pseudallescheria boydii. by thin-layer chromatography, positive phase si-gel col umn chromatography, C-18 reversed-phase si-gel column chromatography,LH20 gel c olumn chromatography, high performance liquid chromatography and recrystallization methods. Their structure were determined by comprehensive analysis of 1DNMR、2DNMR、MS、CD、IR and X-ray single crystal diffraction combined with Literature retrieval methods as follow:pseudaboydinsA(2-1)、pseudaboydinsB(2-2)、(R)-2-(2-hy droxypropan-2-yl)-2,3-dihydro-5-methoxybenzofuran(2-3)、3,3’-dihydroxy-5,5’-dimethyldi phenylether(2-4)、3-(3-methoxy-5-methylphenoxy)-5-methylphenol(2-5)、cyclo-(L-try-L-phe)(2-6)、1,2,3,4-tetrahydro-2-methyl-3-methylene-1,4-dioxopyrazino[1,2-a]indole(2-7)、cyclo-(leu-val)(2-8)、cyclo(Phe-Val)(2-9)、hydroxysydonic acid(2-10)、3-(4-hydroxyphe nyl)propionic acid methyl ester(2-11)、3-isobutylpyrrolopiperazine-2,5-dione(2-12)、c yclo(L-Hyp-L-Ala)(2-13)、cyclo(Tyr-Tyr)(2-14)、cyclo(Phe-Tyr)(2-15)、cyclo(Phe-Tyr)(2-16)、phenyllactic acid(2-17). Among them, Pseudaboydins(2-1), pseudaboydins B(2-2) are new compounds. The absolute configuration of compound(2-3) was determine d as 2R by Circular Dichroism. Cytotoxic test results for compound pseudaboydinsA(2-1) in vitro show that the pseudaboydins A(2-1) show moderate inhibition again st the growth of human nasal cancer cells HONE1 and SUNE1, human lung cancer cell line GLC82 with IC50 37.1, 46.5 �'� 87.2μM,respectively.Four new compounds together with five known compounds were isolated from the culture of the fungus Scedosporium minutisporum. All the compounds were esta blished by comprehensive analysis of the spectral data, especially 1D and 2D-NMR(HMQC and HMBC) spectra. Their structures as follow:penicone A(3-1)、penicone B(3-2)、3-((1H-indol-3-yl)methyl)-6-methyl-3-(methylthio)piperazine-2,5-dione(3-3)、cyc lo(Trp-Ala)(3-4)、lasiodiplines F(3-5)、5,6-dihydroxylasiodiplodin(3-6)、5-hydroxylasio diplodin(3-7)、6-oxolasiodiplodin(3-8)、cyclo(L-Phe-L-Val)(3-9). Among them,penic one A(3-1), Penicone B(3-2), compounds(3-3),(3-6) are new compounds, and pen icone(3-1), Penicone B(3-2) posed novel skeleton structure.The absolute configu ration of penicone A(3-1) was finally established by X-ray single crystal diffraction.Four known compounds:haematocin(4-1)、PyripyropeneA(4-2)、ergosta-5,7,22E-t riene-3β-ol(4-3)and cyclo(leu-leu)(4-4)were isolated from the culture of the fungus F usarium sp. According to reports in the literature,haematocin showed antifungal acti vity,Pyripyropene A(4-2) belongs to pyripyropenes compounds which show inhibitio n against Acyl-CoA: Cholesterol Acyltransferase.