title: Phytotoxic Potential of Secondary Metabolites and Semisynthetic Compounds from Endophytic Fungus Xylaria feejeensis Strain SM3e-1b Isolated from Sapium macrocarpum.
abstract: Bioactivity-directed fractionation of the combined culture medium and mycelium extract of the endophytic fungus Xylaria feejeensis strain SM3e-1b, isolated from Sapium macrocarpum, led to the isolation of three known natural products: (4S,5S,6S)-4-hydroxy-3-methoxy-5-methyl-5,6-epoxycyclohex-2-enone or coriloxine, 1; 2-hydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 2; and 2,6-dihydroxy-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione or fumiquinone B, 3. This is the first report of compound 3 being isolated from this species. Additionally, four new derivatives of coriloxine were prepared: (4R,5S,6R)-6-chloro-4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-enone, 4; 6-hydroxy-5-methyl-3-(methylamino)cyclohexa-2,5- diene-1,4-dione, 5; (4R,5R,6R)-4,5-dihydroxy-3-methoxy-5-methyl-6-(phenylamino)cyclohex-2-enone, 6; and 2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, 7. X-ray analysis allowed us to unambiguously determine the structures and absolute configuration of semisynthetic derivatives 4, 5, and 6. The phytotoxic activity of the three isolated natural products and the coriloxine derivatives is reported. Germination of the seed, root growth, and oxygen uptake of the seedlings of Trifolium pratense, Medicago sativa, Panicum miliaceum, and Amaranthus hypochondriacus were significantly inhibited by all of the tested compounds. In general, they were more effective inhibiting root elongation than suppressing the germination and seedling oxygen uptake processes as shown by their IC50 values.
authors.forename: Marbella Claudia
authors.initials: MC
authors.lastname: García-Méndez
authors.affiliation: Facultad de Quı́mica, Departamento de Fisicoquı́mica, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria , Coyoacán, México, D.F. 04510, México.
authors.forename: Norma A
authors.initials: NA
authors.lastname: Macías-Ruvalcaba
authors.affiliation: Instituto de Biologı́a, Departamento de Botánica, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria , Coyoacán, México, D.F. 04510, México.
authors.forename: Patricia
authors.initials: P
authors.lastname: Lappe-Oliveras
authors.forename: Simón
authors.initials: S
authors.lastname: Hernández-Ortega
authors.forename: Martha Lydia
authors.initials: ML
authors.lastname: Macías-Rubalcava
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D060026:Endophytes / Q000737:chemistry* / Q000378:metabolism; D018525:Germination / Q000187:drug effects; D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000455:Medicago sativa / Q000187:drug effects / Q000254:growth & development; D015394:Molecular Structure; D031287:Sapium / Q000382:microbiology*; D064210:Secondary Metabolism; D012639:Seeds / Q000187:drug effects / Q000254:growth & development; D029921:Trifolium / Q000187:drug effects / Q000254:growth & development; D013098:Xylariales / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001688:Biological Products; D006540:Herbicides
keywords: Sapium macrocarpum; Xylaria feejeensis; coriloxine; endophytic fungi; phytotoxicity; quinones