Characterization And Bioactivity Of Secondary Metabolites From Diplodia Cupressi And Casealpinia Mimosoides

One strain of endobryophytic fungus,Diplodia cupressi,and one medicinal plant,Casealpinia mimosoides Lam.,were chemically investigated in this paper.A total of 45 secondary metabolites including 9 new ones were obtained after repeated column chromatography of silica gel,sephadex LH-20,and Cis reverse-phased silica gel together with semi-preparative HPLC.The structures of these compounds were determined on the basis of NMR,MS,IR,and CD spectroscopy.The compounds obtained were screened for their cytotoxic activity in vitro,and some of them showed different degrees of inhibitory activity on the proliferation of cancer cells.One strain of endobryophytic fungi,Diplodia cupressi,isolated from healthy tissues of the moss Polytrichum commune,was fermented on rice medium and the metaboities were chemically studied.Seven new compounds including two triterpenoids,23,24,25,26,27-pentanorlanost-7,9(11)-dien-3?,22-diol(1)and lanost-8-en-3?,22S,23S-triol(2);one isopimarane-type diterpenoid,diplocupressin D(3);one alkaloid,diplocupredin A(4),one coumarin,diplocuprerin A(5),as well as two triketides,cupressidones D(6)and E(7)were obtained.The 32 known compounds were characterized as one isopimarane-type diterpenoid,sphaeropsidin C(8);one triterpenoid,23,24,25,26,27-pentanorlanost-8-ene-3,22-diol(9);three sesterterpenoids,fusaproliferin(10),(-)-terpestacin(11),and saponaroxin A(12);seven steroids,5,8-epidioxy-5?,8?-ergosta-6,22E-dien-3?-ol(13),5,8-epidioxy-5?,8?-ergosta-6,9,22E-tien-3?-ol(14),ergosterol(15),?-sitosterol(16),stigmasterol(17),pleurocin A(18),and(22E,24R)-3?,5?,9?-trihydroxy-ergosta-7,22-dien-6-one(19);two sesqui-terpenoids,schisansphenin A(20)and 13-nor-4,5-epoxy-7?-cadina-10(14)-en-11-ol(21);nine pentaketides,6-hydroxymellein(22),(R)-4-hydroxymellein(23),(2S,4S)-3,4-dihydro-2,4,8-trihydroxy-1(2H)-naphthalenone(24),(3R,4S)-3,4-dihydro-3,4,8-trihydroxy-1(2H)-naphthalenone(25),(-)-regiolone(26),isoochracinic acid(27),methyl orsellinate(28),ethyl orsellinate(29),and tafuketide(30);six aromatic compounds,4-hydroxyphenylacetic acid(31),4-methoxyphenylacetic acid(32),tyrosol(33),vanillic acid(34),orcinol(35),and bis(2-ethyldecyl)phthalate(36);one lactam,cladosporilactam A(37);one triketide lactone,(R)-mevalonolactone(38),and an unsaturated fatty acid,2,3-dihydroxypropyl 9Z,12Z-octadecadienoate(39).Some compounds were assayed for their anti-proliferative activity,and compounds 10,13,14,18,and 30 showed different degrees of inhibitory activity against the A549,Hep G2 and DU145 cancer cell lines.Two new compounds,including one homoisoflavonoid,(R)-3-(2',4'-dimethoxy-benzyl)-7-hydroxychroman-4-one(40)and one cassane-type diterpenoid,caesalpin I(41),as well as five known ones,including one cassane-type diterpenoid,neocaesalpin(42);one flavone,5,3'-diydroxy-3,7,4'-trimethoxyflavone(43);one homoisoflavonoid,bonducellin(44);two aromatic compounds,1,2,4-trimethoxy-benzene(45)and vanillic acid(34)were isolated from the stems and leaves of C.mimosoides.