Study On The Chemical Constituents Of Two Symbiotic Fungi Xylaria Feejeenisis And Daldinia Eschscholtzii Associated From Spong

In the unique ecological environment of the ocean,marine symbiotic microorganisms and invertebrates in the long process of evolution forming a unique symbiotic mechanism,which can produce a variety of biologically active secondary metabolites.Therefore,marine symbiotic microorganisms as the active material resources of drug which can sustainable development,have become a hot spot in the field of drug research and development.This research investigated the chemical constituents and pharmacological activities of fungi Xylaria feejeenisis and Daldinia eschscholtzii associated with Stylissa massa.37 compounds,including 12 novel compounds,were isolated from the ethyl acetate extraction by column chromatography on silica gel,Sephadex LH-20,and semi-preparative HPLC.By detailed analysis of spectroscopic data NMR,IR,HR-MS,ECD and comparisons with reported data,the structures of these compounds were identified,including 10 terpenes,24 polyketones and 3 ergosterols.Twenty-four compounds were obtained from the fungus Xylaria feejeenisis and identified as:Rubianol-ml?Ml?,?11R*?-0,11,12-guaianetetrol?M2?,?11S*?-10,11,12-guaianetetrol?M3?,2,10,12-guaianetetrol?M4?,stagonolide G?M5?,pestalotiopyrones M?M6?,pestalotiopyrones N?M7?,?1'R?-LL-P880??M8?,?1'S?-LL-P880??M9?,?1'R%2'R?-LL-P880y?M10?,?1'R,2'S?-LL-P880y?M11?,Necpyrone C?M12?,Scirpyrone D?M13?,?6S,1'S?-LL-P880a?M14?,Hydroxypestalotin 5b?M15?,?6S,1'R,2'S?-LL-P880??M16?,?6R,1'R,2'R?-LL-P880??M17?,Scirpyrone I?M18?,annularin D?M19?,Annularins C?M20?,Annularins B?M21?,Annularins A?M22?,3?,5?,6?_22E,24R-ergosta-7,22-dien-3,5,6-triol?M23?,3?,5?,9?-trihydroxy-?22E,24R?-ergosta-7,22-dien-6-one?M24?.Thirteen compounds were obtained from the fungus Daldinia eschscholtzii and identified as:rel-3S,6S,7R,10R-neroplofurol?PI?,rel-3S,6R,7S,10R-neroplofurol?P2?,rel-3S,6S,7S,10R-neroplofurol?P3?,phellinuins I?P4?,?1E,10R*?-1,10-dodecadiene-3,6,7-triol-3,7,11-trimethyl?P5?,?1E,10S*?-1,10-dodecadiene-3,6,7-triol-3,7,11-trimethyl?P6?,eschscholtzii A?P7?,daldinisides C?P8?,8-methoxy-1-naphthalenol-6-O-a-D-ribofuranoside?P9?,helicascolide D?P10?,aspergones R?P11?,aspergones S?P12?,Ergosterol peroxide?P13?.In vitro structure-activity screening,compounds M5-M24 were evaluated for cytotoxicity against cell line A549,cell line SMMC-7721,antifungal activity against Candida parapsilosis ATCC 22019,Candida glabrata 537 and against osteoclast cells activity.A preliminary structure-activity analysis revealed M5,M13,M14 and M23 exhibited inhibitory activity against osteoclast cells.