| STUDIES ONTHE ACTIVE SECONDARYMETABOLITES OF SOIL FUNGIGraduator: Zhang YiSpecial field: MedicinaI chemistryTutor: Pei YuehuABSTRACTA bioassay through detecting deformation or groWth inhibition ofmycelia geminated from conidia of Pyricularia oIyZae, a plant pathogeincfungUs was efficiently applied fOr the primary screeinng of antitUmor andantifungi agents from secondny metabolites of soil fungi. So far 4930fungi were isolated from soil, and six of them (07-1 l, 0288-l, 76-6, l2l-l,l00-3, 0254-2) with stable bioactivity were obtained. Strains 07-1l,0288-1 and 76-6 were identified as Penicillium multicolor Grigoriev-Manoilova & Poradielova, AsPergllus awamori Nakazawa andPenicillium janthinellium Biourge respectively. Sixteen compounds wereobtained from metabolites of them by activty-gUided method.Structures of the sixteen compounds were elucidated byphysicochendcal evidences, spectroscopic methods and X-ray analysis.ErpoSta7, 22-diene-3, 6-dione (Pm-A), N-(4-hydroxy-2-methoxyphenyl)acetamide (Pm-B), 2-hydroxybenZoic acid (Pm-C), 4, 6-dihydroxy-5-methyl- 1(3H)-isobenzofuranone (Pm-D), 2-formyl-3, 5-dihydroxy-4-3methylbenzoic acid (Pm-E) were isolated from P multicolor. 36, 3aa, 4a,6aa-Tetrahydro-l0a-hydroxy-4P, 5, 7atrimethy1-3a-(2-methylpropyl)[cis-transoid-cis-(l2-oxatricyc. l .0"'])]dodeco[4, 3-d]isoindole-l (H), l3-dione (Asp-A), ergosta-5, 7, 22-trien-30-ol (Asp-B), hexadecanoic acid (Asp-C), ergosta-7, 22-diene-36, 5Q, 66-triol (Asp-D), 5%8a-epidioxyergosta-6, 22-diene-30-ol (Asp-E) and ergosta-7, 22-diene-3,6-dione (Asp-F) were separated from A. awamori. From metabolites of Pjanthinellium 5-(l-methylpropyl)-3, 6-dioxo-2-piperaZinepanoic acid (Pj-A), 3-(l-methylethyl)-6-(l-methylpr 5-piperaZinedione (P j-B),(3S, 8aS)-3-methyl-1, 2, 3, 4, 6, 7, 8, 8a-octahydropyrrolo[l, 2-a]-pyrazine-l, 4-dione (P j-C) and docosanoic acid (P j-D) and 2-f Ormyl-3,5-dihydroxy-4-methylbenzoic acid (P j-E) were obtained. CompoundPm-A was identical with Asp-F, and Pm-E was the same as Pj-E.Among thepe Pm-B was isolated as a new natUral product, and itsNMR data were reported for the first time. Asp-A was a novelisoindole-alkaloid with new skeleton. The cyclodipeptide Pj-A was a newcompound too. Pm-A, Pm-D, Asp-F, Pj-B were all obtained from theirgenus fOr the first time. Pm-E and Pj-E were isolated from their speciesfirstly. Comp1ete lH-N'MR signals of compound Pm-A (Asp-F) wereassigned on the basis of 2D-wi spectrum.Compound Asp-A could induce morphological defOrmation ofcoaidia of p. oIyZae. Ergosterols and phenolic acids such as Pm-A(Asp-F), Asp-B, Asp-D, Asp-E, Pm-B, Pm-C, Pm-D, Pm-E (P j-E)could inhibit conidia to gendnate. In the presence of compounds Asp-Dand Asp-E, the spores could geminate normally, but hyphal groWth wasvery abnormal at lower concentration. The cyclodipepitides Pj-A, Pj-B,Pj-C induced mycelia of P oryZae to deform moderately. But fatty acids4Asp-C and Pj-D showed weak effect on curling of hyphal of P. oryzae even in higher concentration. Compounds Pm-B, Pm-C, Pm-D, Asp-A, Asp-B showed no activities to C. albicans.On the basis of ergosterols isolated and the literatures, the spectral characteristics of this kind of compounds were conclude. |
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