The Study Of Active Secondary Metabolites From Three Marine Organisms

Sponges,as the secondary large species of marine organisms,not only produce rich novel bioactive secondary metabolites,also are the one of the largest host of marine microorganisms.A large number of papers had reported novel secondary metabolites from the sponges and their epiphytic or symbiotic microorganisms and bioactivities such as anti-cancer,antibacterial and anti-inflammatory.In this paper,three marine organisms:one sponge Hyrtios sp.and two marine microbial Aspergillus terreus and Streptomyces albidoflavus were researched in order to find the novel structure,physiological activity of secondary metabolites and further study the antibiotics to provide a scientific basis.The amino sesquiterpene quinone solution shows red or purple colors.Due to the terminal olefinic bond and two carbonyl group in the structure of quinone ring,the nuclear magnetic signal characteristic is obvious.Use this as the guidance,13 compounds were isolated from the dichloromethane extraction of sponge that taken from the yongxing island,South China Sea by silica gel column chromatography,ODS column chromatography,Sephadex LH-20 and HPLC.Using UV,MS,1D NMR(1H NMR and 13C NMR),2D NMR(1H-1H COSY,HSQC HMBC and NOESY)spectrum technology,combined with the literature,their structures were determined as 19-hydroxypolyfibrospongol A(A1),nakijiquinone V(A2),smenospongimine(A3),smenospongiarine(A4),sesquiter-penyl-amyl-amino-hydroxy-quinone(A5),smenospongidine(A6),dictyoceratin C(A7),dictyoceratin A(A8),polyfibrospongol A(A9),smenospongic acid(A10),des-hydroxygracilioether C(All),ergosterol peroxide(A12),4(3H)-quinazolinone(A13).Compound A1 and A2 are new compounds and A1 exhibited a weak effect against the PC9 cell line with an IC50 value of 20 μM and A2 showed weak effect against the MCF7 cell line with an IC50 value of 40 μM.Respectively.in the antifungal activity assay,A2 exhibited a weak effect against fungi Trichophyton rubrum 4438 and Candida albicans SC5314 with MIC values of 25μg/mL and Trichophyton mentagrophyte 4439 with MIC values of 12.5 μg/mL,A5 and A6 exhibited a moderate effect against fungi T.mentagrophyte 4439 with MIC values of 6.25 μg/mL and 3.13 μg/mL,besides A6 showed moderate effect against fungi T.rubrum 4438 with MIC values of 1.56 μg/mL.Silica gel column chromatography,ODS column chromatography,and HPLC were used to the EtOAc extraction of the fungi Aspergillus terreus and the actinomycete Streptomyces albidoflavus’s fermention to get compounds,Using UV,MS,1D NMR(1H NMR and 13C NMR),2D NMR(1H-1H COSY,HSQC HMBC and NOESY)spectrum technology,combined with the literature,their structures were determined as 6 compounds from fungi:4-demethylacetate-butyrolactone Ⅰ 3-sulfate(B1),3-hydroxy-5-{Methy1}-4-(4-hydroxyphenyl)-2(5H)-furanone(B2),butyrolactone Ⅰ 3-sulfate(B3),butyrolactone Ⅰ(B4),butyrolactones Ⅶ(B5),terrein(B6)and 6 from actinomycete antimycin A11(C1),daidzein(C2),genistein(C3),cyclo-(L-Pro-L-Tyr)(C4),N-acetyltyramine(C5),cyclo-(Ala-Leu)(C6),B1 was new compound.Antifungal activity was evaluated and only B6 exhibited a weak effect against fungi T.rubrum 4438 and C.albicans SC5314 with MIC values of 12.5 μg/mL and B2 exhibited a moderate effect against fungi T.rubrum 4438 with MIC values of 6.25 μg/mL.C1 exhibited a forceful effect against fungi C.albicans SC5314 with MIC values of 0.195 μg/mL and T.rubrum 4438 and T.mentagrophyte 4439 with MIC values of 1.56 μg/mLSeries of sesquiterpene quinonoid compounds were isolated from the sponge Hyrtios sp.include two news and this study.Series of crotonic acid lactone compounds were isolated from the fungi Aspergillus terreus include one new.This research not only enriched the metabolites diversity of genus Hyrtios sponge and genus Aspergillu fungi S,also has a certain guiding significance for the nature products of genus Hyrtios sponge.In addition,compound(C1)isolated from marine actinomycete(Streptomyces albidoflavus)was found to have good antifungal activity,with the value of further research.The diversity of marine organisms and chemical consitituents were revealed by this study of the sponge and the epiphytic fungi from South China Sea,further provided a certain scientific basis to the potential for the development of marine active drugs.