Chemical Constituents Of An Endolichenic Fungus From Lobaria Retigera And An Endophytic Fungus From Lepidozia Vitrea Steph

Endophytes are bacteria, fungi, and actinomyces, which have a certain stage or the whole stage of life inside healthy plant tissues or organs with no obvious negative influence on their host. In contrast to fungal endophytes feom plants which have been subjected to numerous chemical investigations, only a limited number of endolichenic fungi or endophytic fungi from mosses or liverworts have thus far been investigated for their secondary metabolites, but they also proved to be rich sources of structurally diverse and biologically active small-molecule metabolites.A strain of endolichenic fungi, Aspergillus versicolor, and an endophytic fungus of a liverwort, Penicillium sp. SD1617, were subjected to chemical investigation. After separation and purification by column chromatography of silica gel, sephadex LH-20, and C18reversed phase silica gel, as well as by HPLC preparation, a total of36compounds, including15anthraquinones, three xanthones, seven alkaloids, five benzene derivatives, three steroids, two kojic acid derivatives, and a meroterpenoid, were obtained. The structures of these compounds were determined on the basis of extensive NMR, MS, IR, and UV spectroscopy.A strain of endolichenic fungi, Aspergillus versicolor, isolated from Lobaria retigera was cultivated in rice and the PDB media and the metablites were chemically studied. Fourteen anthraquinones,8-O-methylversicolorins A and B (1and2),8-O-methylaverythin (3),1’-O-ethyl-6,8-di-O-methylaverantin (4),6,8,1’-tri-O- methylaverantin (5),6,8-di-O-methylaverufin (6), aversin (7),6,8-di-O-methylversicolorin A (8),1’-O-methylaverantin (9),6,8-di-O-methylnidurufin (10), averythin (11),6,8-di-O-mrthyl averufanin (21), questin (22), and1-O-methylparirtin (23); three xanthones, sterigmatocystin (12),5-methoxysterigmatocystin (13), and dihydrosterigmatocystin (14); five alkaloids, notoamide C (15), dehydronotoamide C (16),(-)-cyclopenol (17), phomopsin A (18), and3-formylindole (26); two benzene derivatives, dibutyl phthalate (24) and dimethyl phthalate (25); three steroids stigmasterol (19), ergosterol-5,7-dien-3β-o1(27), and dankasterone A (28); as well as one meroterpenoid, asperdemin (20), were obtained. The new compounds1-4were screened for their cytotoxic activity. Compounds1and2showed weak cytotoxic activity against the PC-3and H460cancer cell lines.Eight known compounds, including one anthraquinone, citreorosein (33); two alkaloids, ditryptophenaline (29) and brevianamide F (30); three benzene derivatives4-hydroxybenzaldehyde (34), flemingipanic acid (35), and4-hydroxy-2-methoxy-3,6-dimethylbenzoic acid (36); as well as two kojic acid derivatives, kojic acid (31) and7-O-acetylkojic acid (32), were obtained from one strain of the endophytic fungus(Penicillium sp. SD1617) from the liverwort Lepidozia vitrea Steph.