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  • 1. Albabtain, Reham
    et al.
    Azeem, Muhammad
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. Karolinska Institutet, Sweden.
    Wondimu, Zenebech
    Lindberg, Tulay
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Gustafsson, Anders
    Investigations of a Possible Chemical Effect of Salvadora persica Chewing Sticks2017In: Evidence-based Complementary and Alternative Medicine, ISSN 1741-427X, E-ISSN 1741-4288, article id 2576548Article in journal (Refereed)
    Abstract [en]

    Salvadora persica is commonly used chewing sticks in many parts of the world as an oral hygiene tool. This study measured the amount of benzyl isothiocyanate (BITC) released into the mouth and assessed its retention time in saliva. The study also tested if the released amount of BITC could potentially be antibacterial or cytotoxic. Twelve subjects brushed their teeth with fresh Miswak once, twice, and four times. The amount of BITC in the saliva and in the used brushes was quantified using gas chromatography-mass spectrometry. The antibacterial effect of BITC and Miswak essential oil (MEO) was tested against Haemophilus influenzae, Aggregatibacter actinomycetemcomitans, and Porphyromonas gingivalis. The cytotoxic effect on gingival fibroblasts and keratinocytes was tested using MTT. The highest amount of the active compounds was detected in saliva after using the Miswak tip for once and immediately. It significantly decreased when the Miswak tip was used more than once and thus after 10 min. The growth of the tested bacteria was inhibited by MEO and BITC in a dose dependent manner, P. gingivalis being the most sensitive. MTT assay showed that BITC and MEO were cytotoxic towards gingival fibroblasts while oral keratinocytes showed resistance. This study suggests that the Miswak tip should be cut before each use to ensure the maximum effect.

  • 2.
    Azeem, Muhammad
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Microbes Associated with Hylobius abietis: A Chemical and Behavioral Study2013Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is based on three inter-related studies: the first part deals with the microbial consortium, the identification of microbes and their volatiles, the second part deals with the study of bio-chemical control methods of two conifer pests; the pine weevil Hylobius abietis (L.) and the root rot fungi Heterobasidion spp., and the third part describes the production of styrene by a fungus using forest waste.The large pine weevil (Hylobius abietis L.) is an economically important pest insect of conifers in reforestation areas of Europe and Asia. The female weevils protect their eggs from feeding conspecifics by adding frass (mixture of weevil feces and chewed bark) along with the eggs. In order to understand the mechanism behind frass deposition at the egg laying site and to find repellents/antifeedants for pine weevils, microbes were isolated from the aseptically collected pine weevil frass. Microbial produced volatile organic compounds (VOCs) were collected by solid phase micro extraction and analyzed by GC-MS after cultivating them on weevil frass broth. The major VOCs were tested against pine weevils using a multi-choice olfactometer. Ewingella sp., Mucor racemosus, Penicillium solitum, P. expansum, Ophiostoma piceae, O. pluriannulatum, Debaryomyces hansenii and Candida sequanensis were identified as abundant microbes. Styrene, 6-protoilludene, 1-octene-3-ol, 3-methylanisole, methyl salicylate, 2-methoxyphenol and 2-methoxy-4-vinylphenol were the VOCs of persistently isolated microbes. In behavioral bioassay, methyl salicylate, 3-methylanisole and styrene significantly reduced the attraction of pine weevils to their host plant volatiles. Heterobasidion spp. are severe pathogenic fungi of conifers that cause root and butt rot in plants. Bacterial isolates were tested for the antagonistic activity against fungi on potato dextrose agar. Bacillus subtilis strains significantly inhibited the growth of H. annosum and H. parviporum. Styrene is an industrial chemical used for making polymeric products, currently produced from fossil fuel. A strain of Penicillium expansum isolated from pine weevil frass was investigated for the production of styrene using forest waste. Grated pine stem bark and mature oak bark supplemented with yeast extract produced greater amounts of styrene compared to potato dextrose broth.

  • 3.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Borg-Karlson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kuttuva Rajarao, Gunaratna
    KTH, School of Biotechnology (BIO), Environmental Microbiology.
    Antagonistic activity of Bacillus subtilis A18 – A19 against Heterobasidion speciesArticle in journal (Other academic)
  • 4.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Borg-Karlson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kuttuva Rajarao, Gunaratna
    KTH, School of Biotechnology (BIO), Industrial Biotechnology.
    Sustainable bio-production of styrene from forest waste2013In: Bioresource Technology, ISSN 0960-8524, E-ISSN 1873-2976, Vol. 144, p. 684-688Article in journal (Refereed)
    Abstract [en]

    A strain of Penicillium expansum was studied for the production of styrene using forest waste biomass as a feeding substrate. The fungal strain was cultivated on bark of various trees supplemented with yeast extract and the volatiles produced were collected on Tenax TA and analyzed by gas chromatography-mass spectrometry. Fungus cultured on grated soft bark of pine (Pinus sylvestris) stems (GPB) and mature bark of oak (Quercus robur) supplemented with yeast extract produced relatively the highest amounts of styrene. The maximum styrene production rate was 52.5 mu g/h, 41 mu g/h and 27 mu g/h from fungus cultivated on 50 mL liquid media with 10 g GPB or mature bark of oak and potato dextrose broth respectively. These promising results suggest that the fungal strain could be used to produce "green" styrene plastics using renewable forest waste biomass.

  • 5.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kuttuva Rajarao, Gunaratna
    KTH, School of Biotechnology (BIO), Environmental Microbiology.
    Nagahama, Kazuhiro
    Terenius, Olle
    Dept of genetics microbiology and toxicology, Stockholm University.
    Nordenhem, Henrik
    SLU, Uppsala.
    Nordlander, Göran
    SLU, Uppsala.
    Borg-Karlson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Chemo- and biodiversity of microbes associated with pine weevil (Hylobius abietis)Manuscript (preprint) (Other academic)
  • 6.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kuttuva Rajarao, Gunaratna
    KTH, School of Biotechnology (BIO), Environmental Microbiology (closed September 2009).
    Nordenhem, Henrik
    SLU, Uppsala.
    Nordlander, Göran
    SLU, Uppsala.
    Borg-Karlson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Penicillium expansum Volatiles Reduce Pine Weevil Attraction to Host Plants2013In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 39, no 1, p. 120-128Article in journal (Refereed)
    Abstract [en]

    The pine weevil Hylobius abietis (L.) is a severe pest of conifer seedlings in reforested areas of Europe and Asia. To identify minimally toxic and ecologically sustainable compounds for protecting newly planted seedlings, we evaluated the volatile metabolites produced by microbes isolated from H. abietis feces and frass. Female weevils deposit feces and chew bark at oviposition sites, presumably thus protecting eggs from feeding conspecifics. We hypothesize that microbes present in feces/frass are responsible for producing compounds that deter weevils. Here, we describe the isolation of a fungus from feces and frass of H. abietis and the biological activity of its volatile metabolites. The fungus was identified by morphological and molecular methods as Penicillium expansum Link ex. Thom. It was cultured on sterilized H. abietis frass medium in glass flasks, and volatiles were collected by SPME and analyzed by GC-MS. The major volatiles of the fungus were styrene and 3-methylanisole. The nutrient conditions for maximum production of styrene and 3-methylanisole were examined. Large quantities of styrene were produced when the fungus was cultured on grated pine bark with yeast extract. In a multi-choice arena test, styrene significantly reduced male and female pine weevils' attraction to cut pieces of Scots pine twigs, whereas 3-methylanisole only reduced male weevil attraction to pine twigs. These studies suggest that metabolites produced by microbes may be useful as compounds for controlling insects, and could serve as sustainable alternatives to synthetic insecticides.

  • 7.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. COMSATS Inst Informat Technol, Dept Chem, Abbottabad 22060, Pakistan.
    Kuttuva Rajarao, Gunaratna
    KTH, School of Biotechnology (BIO), Industrial Biotechnology.
    Terenius, Olle
    Nordlander, Goran
    Nordenhem, Henrik
    Nagahama, Kazuhiro
    Norin, Emil
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Borg Karlsson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    A fungal metabolite masks the host plant odor for the pine weevil (Hylobius abietis)2015In: Fungal ecology, ISSN 1754-5048, E-ISSN 1878-0083, Vol. 13, p. 103-111Article in journal (Refereed)
    Abstract [en]

    The pine weevil is one of the most important pest insects of conifer reforestation areas in Europe. Female pine weevils cover their eggs with chewed bark and feces (frass) resulting in avoidance behavior of feeding conspecifics towards egg laying sites. It has been suggested that microorganisms present in the frass may be responsible for producing deterrent compounds for the pine weevil. The fungi Ophiostoma canum, O. pluriannulatum, and yeast Debaryomyces hansenii were isolated from aseptically collected pine-weevil frass. The isolated fungi were cultured on weevil frass broth and their volatiles were collected by SPME and identified by GC MS. D. hansenii produced methyl salicylate (MeS) as a major compound, whereas, in addition, O. canum and O. pluriannulatum produced 6-protoilludene. In a multi-choice lab bioassay, MeS strongly reduced pine weevil's attraction to the Pinus sylvestris volatiles. Thus, a fungal metabolite was found that strongly affects the pine weevil host-odor search. (C) 2014 Elsevier Ltd and The British Mycological Society. All rights reserved.

  • 8.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Norin, Emil
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Terenius, Olle
    Dept of genetics microbiology and toxicology, Stockholm University.
    Kuttuva Rajarao, Gunaratna
    KTH, School of Biotechnology (BIO), Environmental Microbiology.
    Nordlander, Göran
    SLU, Uppsala.
    Nordenhem, Henrik
    SLU, Uppsala.
    Borg-Karlson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fungal metabolite mask the host plant odor of the pine weevil (Hylobius abietis)Article in journal (Other academic)
  • 9.
    Azeem, Muhammad
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, Pakistan.
    Terenius, Olle
    Rajarao, Gunaratna Kuttuva
    KTH, School of Biotechnology (BIO), Industrial Biotechnology.
    Nagahama, Kazuhiro
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Sojo University, Faculty of Biotechnology and Life Science, Department of Applied Microbial Technology, 4-22-1 Ikeda, Nishi-ku, Kumamoto, Japan.
    Nordenhem, Henrik
    Nordlander, Goran
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Tartu University, Institute of Technology, Division of Organic Chemistry, Tartu, Estonia.
    Chemodiversity and biodiversity of fungi associated with the pine weevil Hylobius abietis2015In: Fungal Biology, ISSN 1878-6146, E-ISSN 1878-6162, Vol. 119, no 8, p. 738-46Article in journal (Refereed)
    Abstract [en]

    The pine weevil Hylobius abietis is a severe pest of conifer seedlings in reforestation areas. Weevils lay eggs in the root bark or in the soil near roots of recently dead trees and cover the eggs with frass (feces combined with chewed bark), possibly to avoid conspecific egg predation. The aim of the present investigation focused on isolation, identification, and volatile production of fungi from pine-weevil feces and frass. Fungi were isolated from weevil frass and feces separately, followed by identification based on ITS sequencing. Fifty-nine isolates belonging to the genera Penicillium, Ophiostoma, Mucor, Leptographium, Eucasphaeria, Rhizosphaera, Debaryomyces, and Candida were identified. Volatile organic compounds (VOCs) produced by the fungal community and fungal isolates cultured on weevil-frass broth were identified by SPME-GCMS. Major VOCs emitted from the fungal community and pure isolates were species- and strain specific and included isopentylalcohol, styrene, 3-octanone, 6-protoilludene, methyl salicylate, 3-methylanisole, 2-methoxyphenol, and phenol. Some of these are known to influence the orientation of pine weevils when tested among highly attractive newly planted conifer seedlings.

  • 10.
    El-Seedi, Hesham R.
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. Uppsala University, Sweden.
    Azeem, Muhammad
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. COMSATS Institute of Information Technology, Pakistan.
    Khalil, Nasr S.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. Agricultural Research Centre, Egypt.
    Sakr, Hanem H.
    Khalifa, Shaden A. M.
    Awang, Khalijah
    Saeed, Aamer
    Farag, Mohamed A.
    AlAjmi, Mohamed F.
    Pålsson, Katinka
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Essential oils of aromatic Egyptian plants repel nymphs of the tick Ixodes ricinus (Acari: Ixodidae)2017In: Experimental & applied acarology, ISSN 0168-8162, E-ISSN 1572-9702, Vol. 73, no 1, p. 139-157Article in journal (Refereed)
    Abstract [en]

    Due to the role of Ixodes ricinus (L.) (Acari: Ixodidae) in the transmission of many serious pathogens, personal protection against bites of this tick is essential. In the present study the essential oils from 11 aromatic Egyptian plants were isolated and their repellent activity against I. ricinus nymphs was evaluated Three oils (i.e. Conyza dioscoridis L., Artemisia herba-alba Asso and Calendula officinalis L.) elicited high repellent activity in vitro of 94, 84.2 and 82%, respectively. The most active essential oil (C. dioscoridis) was applied in the field at a concentration of 6.5 A mu g/cm(2) and elicited a significant repellent activity against I. ricinus nymphs by 61.1%. The most repellent plants C. dioscoridis, C. officinalis and A. herba-alba yielded essential oils by 0.17, 0.11 and 0.14%, respectively. These oils were further investigated using gas chromatography-mass spectrometry analysis. alpha-Cadinol (10.7%) and hexadecanoic acid (10.5%) were the major components of C. dioscoridis whereas in C. officinalis, alpha-cadinol (21.2%) and carvone (18.2%) were major components. Artemisia herba-alba contained piperitone (26.5%), ethyl cinnamate (9.5%), camphor (7.7%) and hexadecanoic acid (6.9%). Essential oils of these three plants have a potential to be used for personal protection against tick bites.

  • 11. El-Seedi, Hesham R.
    et al.
    El-Shabasy, Rehan
    Sakr, Hanem
    Zayed, Mervat
    El-Said, Asmaa M. A.
    Helmy, Khalid M. H.
    Gaara, Ahmed H. M.
    Turki, Zaki
    Azeem, Muhammad
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ahmed, Ahmed M.
    Boulos, Loutfy
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Göransson, Ulf
    Anti-schistosomiasis triterpene glycoside from the Egyptian medicinal plant Asparagus stipularis2011In: REV BRAS FARMACOGN, ISSN 0102-695X, Vol. 22, no 2, p. 314-318Article in journal (Refereed)
    Abstract [en]

    Bioassay-guided isolation using an in vitro assay testing for anti-schistosomiasis yielded a novel triterpene saponin, asparagalin A, from the n-butanol extract of the roots of Asparagus stipularis Forssk., Asparagaceae. The structure was elucidated by spectroscopic analysis and chemical transformations. Administration of asparagalin A resulted in a retardation of worm growth and locomotion at the first day and showed a significant activity of egg-laying suppression at 200 mu g/mL concentration.

  • 12. El-Seedi, Hesham R.
    et al.
    Khalil, Nasr S.
    Azeem, Muhammad
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Taher, Eman A.
    Goransson, Ulf
    Pålsson, Katinka
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Chemical Composition and Repellency of Essential Oils From Four Medicinal Plants Against Ixodes ricinus Nymphs: (Acari Ixodidae)2012In: Journal of medical entomology, ISSN 0022-2585, E-ISSN 1938-2928, Vol. 49, no 5, p. 1067-1075Article in journal (Refereed)
    Abstract [en]

    In our search for effective tick repellents from plant origin, we investigated the effect of essential oils of four medicinal and culinary plants belonging to the family Lamiaceae on nymphs of the tick Ixodes ricinus (L.). The essential oils of the dry leaves of Rosmarinus officinalis (Rosemary) (L.), Mentha spicata (Spearmint) (L.), Origanum majorana (Majoram) (L.), and Ocimum basilicum (Basil) (L.) were isolated by steam distillation and 15 mu g/cm(2) concentration of oils was tested against ticks in a laboratory bioassay. The oils of R. officinalis, M. spicata, and O. majorana showed strong repellency against the ticks 100, 93.2, and 84.3%, respectively, whereas O. basilicum only showed 64.5% repellency. When tested in the field, the oils of R. officinalis and M. spicata showed 68.3 and 59.4% repellency at a concentration of 6.5 mu g/cm(2) on the test cloths. The oils were analyzed by gas chromatography mass spectrometry and the major compounds from the most repellent oils were 1,8-cineole, camphor, linalool, 4-terpineol, borneol, and carvone.

  • 13. Kännaste, A.
    et al.
    Laanisto, L.
    Pazouki, L.
    Copolovici, L.
    Suhorutšenko, M.
    Azeem, Muhammad
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. COMSATS Institute of Information Technology, Pakistan.
    Toom, L.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry. University of Tartu, Estonia.
    Niinemets, Ü.
    Diterpenoid fingerprints in pine foliage across an environmental and chemotypic matrix: Isoabienol content is a key trait differentiating chemotypes2018In: Phytochemistry, ISSN 0031-9422, E-ISSN 1873-3700, Vol. 147, p. 80-88Article in journal (Refereed)
    Abstract [en]

    Diterpenoids constitute an important part of oleoresin in conifer needles, but the environmental and genetic controls on diterpenoid composition are poorly known. We studied the presence of diterpenoids in four pine populations spanning an extensive range of nitrogen (N) availability. In most samples, isoabienol was the main diterpenoid. Additionally, low contents of (Z)-biformene, abietadiene isomers, manoyl oxide isomers, labda-7,13,14-triene and labda-7,14-dien-13-ol were quantified in pine needles. According to the occurrence and content of diterpenoids it was possible to distinguish ‘non diterpenoid pines’ ‘high isoabienol pines’ ‘manoyl oxide – isoabienol pines’ and ‘other diterpenoid pines’. ‘Non diterpenoid pines’ ‘high isoabienol pines’ and ‘other diterpenoid pines’ were characteristic to the dry forest, yet the majority of pines (>80%) of the bog Laeva represented ‘high isoabienol pines’. ‘Manoyl oxide – isoabienol pines’ were present only in the wet sites. Additionally, orthogonal partial least-squares analysis showed, that in the bogs foliar nitrogen content per dry mass (NM) correlated to diterpenoids. Significant correlations existed between abietadienes, isoabienol and foliar NM in ‘manoyl oxide – isoabienol pines’ and chemotypic variation was also associated by population genetic distance estimated by nuclear microsatellite markers. Previously, the presence of low and high Δ-3-carene pines has been demonstrated, but the results of the current study indicate that also diterpenoids form an independent axis of chemotypic differentiation. Further studies are needed to understand whether the enhanced abundance of diterpenoids in wetter sites reflects a phenotypic or genotypic response.

  • 14. Sofrata, Abier
    et al.
    Santangelo, Ellen M.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Azeem, Muhammad
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Gustafsson, Anders
    Putsep, Katrin
    Benzyl Isothiocyanate, a Major Component from the Roots of Salvadora Persica Is Highly Active against Gram-Negative Bacteria2011In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 6, no 8, p. e23045-Article in journal (Refereed)
    Abstract [en]

    Plants produce a number of antimicrobial substances and the roots of the shrub Salvadora persica have been demonstrated to possess antimicrobial activity. Sticks from the roots of S. persica, Miswak sticks, have been used for centuries as a traditional method of cleaning teeth. Diverging reports on the chemical nature and antimicrobial repertoire of the chewing sticks from S. persica led us to explore its antibacterial properties against a panel of pathogenic or commensal bacteria and to identify the antibacterial component/s by methodical chemical characterization. S. persica root essential oil was prepared by steam distillation and solid-phase microextraction was used to sample volatiles released from fresh root. The active compound was identified by gas chromatography-mass spectrometry and antibacterial assays. The antibacterial compound was isolated using medium-pressure liquid chromatography. Transmission electron microscopy was used to visualize the effect on bacterial cells. The main antibacterial component of both S. persica root extracts and volatiles was benzyl isothiocyanate. Root extracts as well as commercial synthetic benzyl isothiocyanate exhibited rapid and strong bactericidal effect against oral pathogens involved in periodontal disease as well as against other Gram-negative bacteria, while Gram-positive bacteria mainly displayed growth inhibition or remained unaffected. The short exposure needed to obtain bactericidal effect implies that the chewing sticks and the essential oil may have a specific role in treatment of periodontal disease in reducing Gram-negative periodontal pathogens. Our results indicate the need for further investigation into the mechanism of the specific killing of Gram-negative bacteria by S. persica root stick extracts and its active component benzyl isothiocyanate.

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