title: Phytotoxic eremophilane sesquiterpenes from the coprophilous fungus Penicillium sp. G1-a14.
abstract: Bioassay-directed fractionation of an extract from the grain-based culture of the coprophilous fungus Penicillium sp. G1-a14 led to the isolation of a new eremophilane-type sesquiterpene, 3R,6R-dihydroxy-9,7(11)-dien-8-oxoeremophilane (1), along with three known analogues, namely, isopetasol (2), sporogen AO-1 (3), and dihydrosporogen AO-1 (4). The structure of 1 was elucidated using 1D and 2D NMR and single-crystal X-ray diffraction. Assignment of absolute configuration at the stereogenic centers of 1 was achieved using ECD spectroscopy combined with time-dependent density functional theory calculations. Sporogen AO-1 (3) and dihydrosporogen AO-1 (4) caused significant inhibition of radicle growth against Amaranthus hypochondriacus (IC50 = 0.17 mM for both compounds) and Echinochloa crus-galli (IC50 = 0.17 and 0.30 mM, respectively).
authors.affiliation: Facultad de Química, Universidad Nacional Autónoma de México , México DF 04510, México.
authors.forename: Paulina
authors.initials: P
authors.lastname: Del Valle
authors.forename: Mario
authors.initials: M
authors.lastname: Figueroa
authors.forename: Rachel
authors.initials: R
authors.lastname: Mata
mesh_terms: D000465:Algorithms; D027721:Amaranthus / Q000187:drug effects / Q000254:growth & development; D018360:Crystallography, X-Ray; D031747:Echinochloa / Q000187:drug effects / Q000254:growth & development; D005658:Fungi / Q000187:drug effects; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: C000600375:3R,6R-dihydroxy-9,7(11)-dien-8-oxoeremophilane; D012717:Sesquiterpenes