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  • 1.
    Bergström, Maria
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Ganji, Suresh
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Naidu Veluru, Ramesh
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Unelius, C. Rikard
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    N-Iodosuccinimide (NIS) in Direct Aromatic Iodination2017In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 22, p. 3234-3239Article in journal (Refereed)
    Abstract [en]

    N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono-and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA.

  • 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.
    Rao, M. Suri Appa
    et al.
    CSIR, India.
    Ganji, Suresh
    CSIR, India.
    Yadav, P. Ashok
    CSIR, India.
    Prasad, K. Rajendra
    CSIR, India.
    Rani, P. Usha
    CSIR, India.
    Rao, C. Venkata
    Sri Venkateswara Univ, India.
    Babu, K. Suresh
    CSIR, India.
    Piscidinols H-L, apotirucallane triterpenes from the leaves of Walsura trifoliata and their insecticidal activity2015In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 71, no 9, p. 1431-1437Article in journal (Refereed)
    Abstract [en]

    Five new apotirucallane-type terpenoids, Piscidinols H-L (1-5), were isolated from the leaves of Walsura trifoliate and their structures were fully established on the basis of detailed spectroscopic (especially 20 NMR and mass) analysis. These new compounds possessed tetracyclic and acetal rings. All the new isolates were evaluated for their antifeedant activities in tobacco caterpillar (Spodoptera aura) and castor semilooper (Achaea janata) using a no-choice laboratory bioassay and the test compounds (1-6) exhibited moderate insecticidal activities. (C) 2015 Elsevier Ltd. All rights reserved.

  • 4.
    Schiebe, Christian
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Swedish University of Agricultural Sciences, Sweden.
    Unelius, C. Rikard
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Ganji, Suresh
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Binyameen, Muhammad
    Bahauddin Zakariya Univ, Pakistan;Czech Univ Life Sci Prague, Czech Republic.
    Birgersson, Göran
    Swedish University of Agricultural Sciences, Sweden.
    Schlyter, Fredrik
    Swedish University of Agricultural Sciences, Sweden;Czech Univ Life Sci Prague, Czech Republic.
    Styrene, (+)-trans-(1R,4S,5S)-4-Thujanol and Oxygenated Monoterpenes Related to Host Stress Elicit Strong Electrophysiological Responses in the Bark Beetle Ips typographus2019In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 45, no 5-6, p. 474-489Article in journal (Refereed)
    Abstract [en]

    Bark beetles kill apparently vigorous conifers during epidemics by means of pheromone-mediated aggregation. During non-endemic conditions the beetles are limited to use trees with poor defense, like wind-thrown. To find olfactory cues that help beetles to distinguish between trees with strong or weak defense, we collected volatiles from the bark surface of healthy felled or standing Picea abies trees. Furthermore, living trees were treated with methyl jasmonate in order to induce defense responses. Volatiles were analyzed by combined gas chromatography and electroantennographic detection (GC-EAD) on Ips typographus antennae. Compounds eliciting antennal responses were characterized by single sensillum recording for identification of specific olfactory sensory neurons (OSN). Release of monoterpene hydrocarbons decreased, while oxygenated compounds increased, from spring to early summer in felled trees. In both beetle sexes particular strong EAD activity was elicited by trace amounts of terpene alcohols and ketones. 4-Thujanol gave a very strong response and the absolute configuration of the tested natural product was assigned to be (+)-trans-(1R,4S,5S)-thujanol by stereoselective synthesis and enantioselective gas chromatography. One type of OSN responded to all ketones and five other OSN were characterized by the type of compounds that elicited responses. Three new OSN classes were found. Of the eight EAD-active compounds found in methyl jasmonate-treated bark, the known anti-attractant 1,8-cineole was the one most strongly induced. Our data support the hypothesis that highly active oxygenated host volatiles could serve as positive or negative cues for host selection in I. typographus and in other bark beetles.

  • 5.
    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.

  • 6.
    Zhao, Tao
    et al.
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. KTH Royal Instute of Technology, Sweden;Örebro University, Sweden.
    Ganji, Suresh
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Bohman, Björn
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. University of Western Australia, Australia.
    Weinstein, Philip
    University of Adelaide, Australia.
    Krokene, Paal
    Norwegian Institute of Bioeconomy Research, Norway.
    Borg-Karlsson, Anna-Karin
    KTH Royal Instute of Technology, Sweden.
    Unelius, C. Rikard
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.
    Convergent evolution of semiochemicals across Kingdoms: bark beetles and their fungal symbionts2019In: The ISME Journal, ISSN 1751-7362, E-ISSN 1751-7370, Vol. 13, no 6, p. 5-1545Article in journal (Refereed)
    Abstract [en]

    Convergent evolution of semiochemical use in organisms from different Kingdoms is a rarely described phenomenon. Treekilling bark beetles vector numerous symbiotic blue-stain fungi that help the beetles colonize healthy trees. Here we show for the first time that some of these fungi are able to biosynthesize bicyclic ketals that are pheromones and other semiochemicals of bark beetles. Volatile emissions of five common bark beetle symbionts were investigated by gas chromatography-mass spectrometry. When grown on fresh Norway spruce bark the fungi emitted three well-known bark beetle aggregation pheromones and semiochemicals (exo-brevicomin, endo-brevicomin and trans-conophthorin) and two structurally related semiochemical candidates (exo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane and endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1] nonane) that elicited electroantennogram responses in the spruce bark beetle Ips typographus. When grown on malt agar with 13C D-Glucose, the fungus Grosmannia europhioides incorporated 13C into exo-brevicomin and trans-conophthorin. The enantiomeric compositions of the fungus-produced ketals closely matched those previously reported from bark beetles. The production of structurally complex bark beetle pheromones by symbiotic fungi indicates cross-kingdom convergent evolution of signal use in this system. This signaling is susceptible to disruption, providing potential new targets for pest control in conifer forests and plantations.

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