Studies On The Secondary Metabolites From Three Fungi

As sources of structurally novel and biologically active secondary metabolites,fungi play an important role in lead compound research.In the course of our ongoing studies of new bioactive natural products from fungi,compounds in the secondary metabolites of three fungi from different sources were isolated and elucidated by extensive NMR and HR-ESI-MS experiments.Penicillium griseofulvum T21-03 was collected from Acrostichum aureum in Hainan intertidal fern.From its fermentation broth and mycelia,17 compounds were isolated and elucidated according to their physical and chemical properties and spectral characteristics as follows:4,6-dimethylcurvulinic acid(T1),penicitrinol P(T2),penicitrinone A(T3),penicitrinone B(T4),6,8-dihydroxy-3,4,5,7-tetramethyl-3,4-dihydroisocoumarin(T5),Decarboxydihydrocitrinin(T6),1-(3,5-dihydroxy-2,4-dimethylphenyl)propan-2-one(T7),2hydroxy-3,5-dimethyl-6-(2-oxopropyl)cyclohexa-2,5-diene-1,4-dione(T8),4-methyl phenol A(T9),phenol A(T10),phenethyl alcohol(T11),p-hydroxyphenylacetic acid methyl ester(T12),p-hydroxyphenylethanol-2’-(S)-hydroxy propionic acid ester(T13),quinoloniruide(T14),Cyclo(Tyr-Phe)(T15),Cyclo(Pro-Val)(T16),succinic acid(T17).Specially,T1 and T2 were new compounds among them.Xylariaceae sp.DWS-5-p-11 was isolated from soil on Daweishan,in May,2014.We isolated 22 compounds from its fermentation broth and mycelia.According to the physicochemical properties and spectral data,we elucidated their structures as follows:NbAcetyltryptamine(Dl),3-Hydroxy-3-methyl-2-mdolinone(D2),3-Hydroxy-1,3-dimethylindolin-2-one(D3),questin(D4),Cyclo(Leu-Ile)(D5),Cyclo(Hpro-Phe)(D6),Cyclo(Pro-Phe)(D7),Cyclo(Phe-Gly)(D8),Cyclo(Leu-Hpro)(D9),Cyclo(Trp-Pro)(D10),Cyclo(Val-Phe)(D11),Cyclo(Tyr-Phe)(D12),butyrolactone I(D13),flazine(D14),2-hydroxy benzene acetic acid 4-hydroxy ethyl benzene(D15),Cyclo(Ala-Gly)(D16),uracil(D17),mannitol(D18),alanine(D19),Cyclo(Leu-Phe)(D20),phenylalanine(D21),β-adenosine(D22).The fungus Aspergillus flavipes PJ03-11 was isolated from the wetland soil collected from Panjin Red Beach National Nature Reserve.17 compounds were isolated from the fermentation products.According to the physical chemical properties and spectral data,15 compounds were identified as follows:butyl 2,4-dichloroasterrate(PJ1),2-ethylhexy1-2,4-dichloroasterrate(PJ2*),Butyl Asterrate(PJ3),butyl 2,4-dichloroasterric acid(PJ4),2,4-dichloroasterric acid(PJ5),methyl dichloroasterrate(PJ6),questin(PJ7),isorhodoptilometrin(PJ8),2-O-Methylbutyrolactone I(PJ9),aspergillin PZ(PJ10),flavipesoside 1(PJ11),flavipesoside 3(PJ12),Acetylflavipesoside 1(PJ13),flavipesoside 5(PJ14)and flavipesene 3(PJ15).Among them,PJ2,PJ4,PJ11-PJ14 are new compounds.The cytotoxic effects of compounds PJ1-PJ3,PJ11-PJ15 were evaluated by the MTT method on HL-60,HCT116,PC-3 or HT-29 cancer cell lines.The results showed that PJ1-PJ3,PJ14,J15 showed cytotoxic activities.