title: Secondary metabolites of the sponge-derived fungus Acremonium persicinum.
abstract: This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines O (6), P (7), Q (8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (1S, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by ¹H NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The ³J(H-C) values in acremine P were measured using the pulse sequence EXSIDE, and the observed ³J(H8-C4) of 5.4 Hz and small ³J(H-C) values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q, NOESY data combined with molecular modeling established the preferred diastereomer 8a.
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland , Brisbane QLD 4072, Australia.
authors.lastname: Suciati
authors.forename: James A
authors.initials: JA
authors.lastname: Fraser
authors.forename: Lynette K
authors.initials: LK
authors.lastname: Lambert
authors.forename: Gregory K
authors.initials: GK
authors.lastname: Pierens
authors.forename: Paul V
authors.initials: PV
authors.lastname: Bernhardt
authors.forename: Mary J
authors.initials: MJ
authors.lastname: Garson
mesh_terms: D000164:Acremonium / Q000737:chemistry*; D000818:Animals; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D011161:Porifera / Q000382:microbiology*; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D013729:Terpenes; C584587:acremine P