title: Antileishmanial metabolites from Geosmithia langdonii.
abstract: Antileishmanial bioassay guided fractionation of Geosmithia langdonii has resulted in the isolation and identification of two new compounds (1 and 2) together with 10 known compounds (3-12). The structures of the isolated metabolites were elucidated based on comprehensive 1D and 2D NMR spectroscopic data as well as mass spectrometry. The absolute configuration at C4, C5, and C6 of 2 was determined as R using a modified Mosher esterification method and NOESY correlations. The extracts and the isolated metabolites were evaluated for their antileishmanial activities. Compounds 3, 9, 11, and 12 were found to be active against Leishmania donovani with IC50 values of 6.9, 3.3, 8.5, and 9.2 μM, respectively, while compounds 1, 5, and 10 showed lower activities against L. donovani with IC50 values of 13.0, 47.3, and 34.0 μM, respectively.
authors.affiliation: National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi , University, Mississippi 38677, United States.
authors.forename: Lourin G
authors.initials: LG
authors.lastname: Malak
authors.forename: Mohamed Ali
authors.initials: MA
authors.lastname: Ibrahim
authors.forename: Daoud W
authors.initials: DW
authors.lastname: Bishay
authors.forename: Afaf M
authors.initials: AM
authors.lastname: Abdel-baky
authors.forename: Ahmed M
authors.initials: AM
authors.lastname: Moharram
authors.forename: Babu
authors.initials: B
authors.lastname: Tekwani
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Cutler
authors.forename: Samir A
authors.initials: SA
authors.lastname: Ross
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry; D001232:Aspergillus fumigatus / Q000187:drug effects; D001559:Benzhydryl Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects; D003512:Cyclohexanones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects; D006999:Hypocreales / Q000737:chemistry*; D007893:Leishmania donovani / Q000187:drug effects*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D015269:Mycobacterium avium Complex / Q000187:drug effects; D010963:Plasmodium falciparum / Q000187:drug effects; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012459:Salicylates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: C000594555:(4R,5R,6R)-4,5-dihydroxy-6-(6'-methylsalicyloxy)-2-methyl-2-cyclohexen-1-one; C000594554:4-(2',4'-dihydroxy-6'-(hydroxymethyl)benzyl)benzene-1,2-diol; D000972:Antineoplastic Agents, Phytogenic; D001559:Benzhydryl Compounds; D003512:Cyclohexanones; D012459:Salicylates
references.citation: Mycol Res. 2005 Dec;109(Pt 12):1323-36
references.pmid: 16353633
references.citation: Trans R Soc Trop Med Hyg. 2001 May-Jun;95(3):239-43
references.pmid: 11490989
references.citation: J Nat Prod. 2002 Sep;65(9):1278-82
references.pmid: 12350147
references.citation: Antimicrob Agents Chemother. 2004 Nov;48(11):4450-2
references.pmid: 15504880
references.citation: Chemistry. 2007;13(4):1064-77
references.pmid: 17171737
references.citation: Planta Med. 2012 Oct;78(15):1690-7
references.pmid: 22903383
references.citation: Comp Immunol Microbiol Infect Dis. 2004 Sep;27(5):305-18
references.pmid: 15225981
references.citation: Bioorg Med Chem. 2007 Jan 1;15(1):87-96
references.pmid: 17070063
references.citation: Toxicol In Vitro. 2004 Oct;18(5):703-10
references.pmid: 15251189
references.citation: Int J Mol Med. 2008 Sep;22(3):277-86
references.pmid: 18698485
references.citation: J Infect. 1990 Nov;21(3):261-70
references.pmid: 2273273
references.citation: Biosci Biotechnol Biochem. 2008 Aug;72(8):2069-73
references.pmid: 18685216
references.citation: J Antibiot (Tokyo). 2001 Nov;54(11):882-9
references.pmid: 11827029