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  • 1.
    Bohman, Björn
    et al.
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Troger, A.
    University of Hamburg.
    Franke, S.
    University of Hamburg.
    Lorenzo, M. G.
    Fiocruz, Belo Horizonte, Brazil.
    Francke, W.
    University of Hamburg.
    Unelius, C. Rikard
    Linnaeus University, Faculty of Science and Engineering, School of Natural Sciences.
    Structure Elucidation and Synthesis of Dioxolanes Emitted by Two Triatoma Species (Hemiptera Reduviidae)2011In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 74, no 4, p. 690-694Article in journal (Refereed)
    Abstract [en]

    Volatiles from the metastemal glands of two species Of true bugs of the Triatominae subfamily, Triatoma brasiliensis and Triatoma infestans, Were analyzed by SPME-GC/MS. Two sets of new natural products were found: (4S,5S)- and (4R,SR)-2,2,4-triethyl-5-methyl-1,3-dioxolane (1) (major component) and (45*,5S*)-2,4-diethyl-2,S-dimethyl-1,3-dioxolane (2) (trace component),-,(2R/S,4S,SS)- as well as (2R/S,4R,5R)-4-ethyl-5-methyl-2-(1-methylethyl)-1,3-dioxolane (3) (minor component), (2R/S,4S*,5S*).-4-ethyl-5-methyl-2-(1-methylpropyl)-1,3-dioxolane (4), (trace component), and (2R/S,4S*,5S*)-4-ethyl-5-methyl-2-(2-methylpropyl)-1,3-dioxolane (5) (trace component). Syntheses of optically active 1 and 3 were carried out by reacting pure,enantiomers of 2,3-pentanediol with 3-pentanone or 2-methylpropanal. The preparation of, pure 1 stereoisomers of 2,3-pentanediol involved a novel key step for the synthesis of secondary alcohols: the reduction of a carboxylic ester by means of DIBAH and in situ alkylation of the intermediate by Grignard reaction at low temperature Starting from the pure enantiomers of methyl lactate; all four stereoisoniers of 2,3-pentanediol were synthesized. and transformed, to the corresponding isomers of 1 and 2. Relative configurations of the natural products and enantiomeric compositions of naturally occurring 1 and :2 were determined by comparison of their mass spectra and gas chromatographic retention times (co-injection) I with those of authentic reference samples.

  • 2.
    Nasrin, Shamima
    et al.
    Auburn Univ, USA.
    Ganji, Suresh
    Univ Mississippi, USA.
    Kakirde, Kavita S.
    Auburn Univ, USA.
    Jacob, Melissa R.
    Univ Mississippi, USA.
    Wang, Mei
    Univ Mississippi, USA.
    Ravu, Ranga Rao
    Univ Mississippi, USA.
    Cobine, Paul A.
    Auburn Univ, USA.
    Khan, Ikhlas A.
    Univ Mississippi, USA.
    Wu, Cheng-Cang
    Lucigen Corp, USA.
    Mead, David A.
    Varigen Biosci Corp, USA.
    Li, Xing-Cong
    Univ Mississippi, USA.
    Liles, Mark R.
    Auburn Univ, USA;Varigen Biosci Corp, USA.
    Chloramphenicol Derivatives with Antibacterial Activity Identified by Functional Metagenomics2018In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 81, no 6, p. 1321-1332Article in journal (Refereed)
    Abstract [en]

    A functional metagenomic approach identified novel and diverse soil-derived DNAs encoding inhibitors to methicillin-resistant Staphylococcus aureus (MRSA). A metagenomic DNA soil library containing 19 200 recombinant Escherichia coli BAC clones with 100 Kb average insert size was screened for antibiotic activity. Twenty-seven clones inhibited MRSA, seven of which were found by LC-MS to possess modified chloramphenicol (Cm) derivatives, including three new compounds whose structures were established as 1-acetyl-3-propanoylchloramphenicol, 1-acety1-3-butanoyl-chloramphenicol, and 3-butanoyl-1-propanoylchloramphenicol. Cm was used as the selectable antibiotic for cloning, suggesting that heterologously expressed enzymes resulted in derivatization of Cm into new chemical entities with biological activity. An esterase was found to be responsible for the enzymatic regeneration of Cm, and the gene trfA responsible for plasmid copy induction was found to be responsible for inducing antibacterial activity in some clones. Six additional acylchloramphenicols were synthesized for structure and antibacterial activity relationship studies, with 1-p-nitrobenzoylchloramphenicol the most active against Mycobacterium intracellulare and Mycobacterium tuberculosis, with MICs of 12.5 and 50.0 mu g/mL, respectively.

  • 3. Unelius, C. Rikard
    et al.
    Santangelo, E. M.
    KTH, Sweden.
    Coracini, M.
    SLU, Sweden.
    Witzgall, P.
    SLU, Sweden.
    Correa, A. G.
    Brazil.
    Identification, syntheses, and characterization of the geometric isomers of 9,11-hexadecadienal from female pheromone glands of the sugar cane borer Diatraea saccharalis2002In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 65, no 6, p. 909-915Article in journal (Refereed)
    Abstract [en]

    Chemical analysis of the pheromone glands of the sugar cane borer Diatraea saccharalis has shown the presence of the four geometric isomers of 9,11-hexadecadienal (1-4), in addition to hexadecanal and (Z)-hexadec-11-enal. We here report the syntheses and characterization of compounds 1-4. One starting material, 9-decen-1-ol, has been used to obtain all of them via divergent synthetic routes.

  • 4.
    Yu, Qian
    et al.
    University of Mississippi, USA;China Pharmaceut University, Peoples Republic of China.
    Ravu, Ranga Rao
    University of Mississippi, USA.
    Xu, Qiong-Ming
    University of Mississippi, USA.
    Ganji, Suresh
    University of Mississippi, USA.
    Jacob, Melissa R.
    University of Mississippi, USA.
    Khan, Shabana I.
    University of Mississippi, USA.
    Yu, Bo-Yang
    China Pharmaceut University, Peoples Republic of China.
    Li, Xing-Cong
    University of Mississippi, USA.
    Antibacterial Prenylated Acylphloroglucinols from Psorothamnus fremontii2015In: Journal of natural products (Print), ISSN 0163-3864, E-ISSN 1520-6025, Vol. 78, no 11, p. 2748-2753Article in journal (Refereed)
    Abstract [en]

    Psorothatins A-C (1-3), three antibacterial prenylated acylphloroglucinol derivatives, were isolated from the native American plant Psorothamnus fremontii. They feature an unusual alpha,beta-epoxyketone functionality and a beta-hydroxy-alpha,beta-unsaturated ketone structural moiety. The latter forms a pseudo-six-membered heterocyclic ring due to strong intramolecular hydrogen bonding, as indicated by the long-range proton-carbon correlations in the NMR experiments. Psorothatin C (3) was the most active compound against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium, with IC50 values in the range 1.4-8.8 mu g/mL. The first total synthesis of 3 described herein permits future access to structural analogues with potentially improved antibacterial activities.

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