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  • 1. Boone, Celia K
    et al.
    Keefover-Ring, Ken
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology.
    Mapes, Abigail C
    Adams, Aaron S
    Bohlmann, Jörg
    Raffa, Kenneth F
    Bacteria associated with a tree-killing insect reduce concentrations of plant defense compounds2013In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 39, no 7, p. 1003-1006Article in journal (Refereed)
  • 2. Holeski, Liza M
    et al.
    Keefover-Ring, Ken
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology.
    Bowers, M Deane
    Harnenz, Zoe T
    Lindroth, Richard L
    Patterns of phytochemical variation in Mimulus guttatus (Yellow Monkeyflower)2013In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 39, no 4, p. 525-536Article in journal (Refereed)
    Abstract [en]

    The search for general patterns in the production and allocation of plant defense traits will be facilitated by characterizing multivariate suites of defense, as well as by studying additional plant taxa, particularly those with available genomic resources. Here, we investigated patterns of genetic variation in phytochemical defenses (phenylpropanoid glycosides, PPGs) in Mimulus guttatus (yellow monkeyflower). We grew plants derived from several natural populations, consisting of multiple full-sibling families within each population, in a common greenhouse environment. We found substantial variation in the constitutive multivariate PPG phenotype and in constitutive levels of individual phytochemicals within plants (among leaves of different ages), within populations (among full-sibling families), and among populations. Populations consisting of annual plants generally, but not always, had lower concentrations of phytochemicals than did populations of perennial plants. Populations differed in their plastic response to artificial herbivory, both in the overall multivariate PPG phenotype and in the individual phytochemicals. The relationship between phytochemistry and another defense trait, trichomes, differed among populations. Finally, we demonstrated that one of the PPGs, verbascoside, acts as a feeding stimulant rather than a feeding deterrent for a specialist herbivore of M. guttatus, the buckeye caterpillar (Junonia coenia Nymphalidae). Given its available genetic resources, numerous, easily accessible natural populations, and patterns of genetic variation highlighted in this research, M. guttatus provides an ideal model system in which to test ecological and evolutionary theories of plant-herbivore interactions.

  • 3.
    Keefover-Ring, Ken
    et al.
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC). Department of Entomology, University of Wisconsin-Madison, Madison, Wisconsin, United States of America.
    Ahnlund, Maria
    Department of Forest Genetics and Plant Physiology, Swedish University of Agricultural Sciences, Umeå Plant Science Centre, Umeå, Sweden.
    Abreu, Ilka Nacif
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC). Department of Forest Genetics and Plant Physiology, Swedish University of Agricultural Sciences, Umeå Plant Science Centre, Umeå, Sweden.
    Jansson, Stefan
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC).
    Moritz, Thomas
    Department of Forest Genetics and Plant Physiology, Swedish University of Agricultural Sciences, Umeå Plant Science Centre, Umeå, Sweden.
    Albrectsen, Benedicte Riber
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC). Department of Plant and Environmental Sciences, University of Copenhagen, Frederiksberg, Denmark.
    No evidence of geographical structure of salicinoid chemotypes within Populus tremula2014In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 9, no 10, p. e107189-Article in journal (Refereed)
    Abstract [en]

    Salicinoids are well-known defense compounds in salicaceous trees and careful screening at the population level is warranted to fully understand their diversity and function. European aspen, Populus tremula, is a foundation species in Eurasia and highly polymorphic in Sweden. We exhaustively surveyed 102 replicated genotypes from the Swedish Aspen collection (SwAsp) for foliar salicinoids using UHPLC-ESI-TOF/MS and identified nine novel compounds, bringing the total to 19 for this species. Salicinoid structure followed a modular architecture of a salicin skeleton with added side groups, alone or in combination. Two main moieties, 2'-cinnamoyl and 2'-acetyl, grouped the SwAsp population into four distinct chemotypes, and the relative allocation of salicinoids was remarkably constant between different environments, implying a highly channeled biosynthesis of these compounds. Slightly more than half of the SwAsp genotypes belonged to the cinnamoyl chemotype. A fraction synthesized the acetyl moiety alone (similar to 7%) or in combination with cinnamoyl (similar to 2%), and close to forty percent lacked either of the two characteristic moieties, and thus resemble P. tremuloides in their salicinoid profile. The two most abundant chemotypes were evenly distributed throughout Sweden, unlike geographical patterns reported for SwAsp phenology traits, plant defense genes, and herbivore community associations. Here we present the salicinoid characterization of the SwAsp collection as a resource for future studies of aspen chemical ecology, salicinoid biosynthesis, and genetics.

  • 4.
    Keefover-Ring, Ken
    et al.
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC).
    Carlsson, Marcus
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Albrectsen, Benedicte R
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC).
    2 '-(Z)-Cinnamoylsalicortin: A novel salicinoid isolated from Populus tremula2014In: Phytochemistry Letters, ISSN 1874-3900, E-ISSN 1876-7486, Vol. 7, p. 212-216Article in journal (Refereed)
    Abstract [en]

    Using a combination of NMR and mass spectroscopic techniques, we have isolated a new salicinoid from the foliage of European aspen (Populus tremula) and identified it as 2'-(Z)-cinnamoylsalicortin. The relatively high amounts in foliage and the similarity in structure to bioactive salicinoids isolated from other salicaceous trees indicates that this compound may have implications for the study of P. tremulaherbivore interactions.

  • 5.
    Keefover-Ring, Ken
    et al.
    Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC). Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Department of Entomology, University of Wisconsin, USA.
    Holeski, Liza M.
    Bowers, M. Deane
    Clauss, Allen D.
    Lindroth, Richard L.
    Phenylpropanoid glycosides of Mimulus guttatus (yellow monkeyflower)2014In: Phytochemistry Letters, ISSN 1874-3900, E-ISSN 1876-7486, Vol. 10, p. 132-139Article in journal (Refereed)
    Abstract [en]

    Yellow monkeyflower [Mimulus guttatus DC., (Phyrmaceae)] has long been a model plant species for studies in genetics, evolution, and ecology, including plant-animal interactions. Nonetheless, exceedingly little is known about its secondary chemistry. We have discovered that the foliage of yellow monkeyflower contains a diverse suite of phenylpropanoid glycosides (PPGs); a class of compounds with many known biological activities. Using H-1 and C-13 NMR and UV and MS chromatography techniques, we positively identified five PPGs from the leaves of yellow monkeyflower. Four of these compounds occur in other species and one is previously undescribed. We also present UV and high- resolution tandem MS data that putatively identify 11 additional foliar compounds as PPGs. This initial discovery and elucidation of yellow monkeyflower's secondary chemistry will be important for continued study of the genetics and ecology of this model species. (C) 2014 Phytochemical Society of Europe. 

  • 6.
    Keefover-Ring, Kenneth
    Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC).
    Making scents of defense: Do fecal shields and herbivore-caused volatiles match host plant chemical profiles?2013In: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 23, no 1, p. 1-11Article in journal (Refereed)
    Abstract [en]

    Many plant families have aromatic species that produce volatile compounds which they release when damaged, particularly after suffering herbivory. Monarda fistulosa (Lamiaceae) makes and stores volatile essential oils in peltate glandular trichomes on leaf and floral surfaces. This study examined the larvae of a specialist tortoise beetle, Physonota unipunctata, which feed on two M. fistulosa chemotypes and incorporate host compounds into fecal shields, structures related to defense. Comparisons of shield and host leaf chemistry showed differences between chemotypes and structures (leaves vs. shields). Thymol chemotype leaves and shields contained more of all compounds that differed than did carvacrol chemotypes, except for carvacrol. Shields had lower levels of most of the more volatile chemicals than leaves, but more than twice the amounts of the phenolic monoterpenes thymol and carvacrol and greater totals. Additional experiments measured the volatiles emitted from M. fistulosa in the absence and presence of P. unipunctata larvae and compared the flower and foliage chemistry of plants from these experiments. Flowers contained lower or equal amounts of most compounds and half the total amount, compared to leaves. Plants subjected to herbivory emitted higher levels of most volatiles and 12 times the total amount, versus controls with no larvae, including proportionally more of the low boiling point chemicals. Thus, chemical profiles of shields and volatile emissions are influenced by the amounts and volatilities of compounds present in the host plant. The implications of these results are explored for the chemical ecology of both the plant and the insect. 

  • 7.
    Pratt, Jessica D.
    et al.
    Univ Calif Irvine, Dept Ecol & Evolutionary Biol, Irvine, CA 92697 USA.
    Keefover-Ring, Ken
    Umeå University, Faculty of Science and Technology, Umeå Plant Science Centre (UPSC). Umeå University, Faculty of Science and Technology, Department of Plant Physiology. Univ Wisconsin, Dept Entomol, Madison, WI 53706 USA.
    Liu, Lawrence Y.
    Univ Calif Irvine, Dept Ecol & Evolutionary Biol, Irvine, CA 92697 USA.
    Mooney, Kailen A.
    Univ Calif Irvine, Dept Ecol & Evolutionary Biol, Irvine, CA 92697 USA.
    Genetically based latitudinal variation in Artemisia californica secondary chemistry2014In: Oikos, ISSN 0030-1299, E-ISSN 1600-0706, Vol. 123, no 8, p. 953-963Article in journal (Refereed)
    Abstract [en]

    Steep climatic gradients may select for clinal adaptation in plant functional traits with implications for interspecific interactions and response to future climate change. Terpenes are common in Mediterranean environments and mediate plant interactions with both the abiotic and biotic environment, including herbivores. Clines in traits such as terpenes have received much attention because they are linked to plant fitness and experience strong selection from the abiotic and biotic environment. In this study, we tested for intraspecific variation in Artemisia californica terpene chemistry in a common garden of plants sourced from populations spanning a large precipitation gradient (6 latitude) and grown in treatments of high and low precipitation. We found genetic variation in terpene richness, diversity, concentration and composition among A. californica populations spanning this species' range. Of these traits, terpene composition and monoterpene concentration varied clinally with respect to source site latitude. Regarding terpene composition, pairwise dissimilarity among populations increased in parallel with geographic distance between source sites. At the same time, monoterpene concentration decreased monotonically from plants of southern origin (source sites with high temperature, aridity, and precipitation variability) to plants of northern origin. Our precipitation manipulation suggests that phenotypic selection by precipitation may underlie this clinal variation in monoterpene concentration, and that monoterpene concentration and other aspects of terpene chemistry are not phenotypically plastic. In summary, this study provides novel evidence for a genetically based latitudinal cline in plant secondary chemistry and suggests that adaptation to a key aspect of the abiotic environment may contribute to this intraspecific variation. Accordingly, changes in terpene chemistry under projected future climates will likely occur solely through the relatively slow process of adaptation, with important consequences for plant interactions with the abiotic environment and a diverse community of associates.

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