Full Text Journal Articles by
Author Frank C Schroeder

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An Untargeted Approach for Revealing Electrophilic Metabolites.

Yan Yu, Henry H Le, Brian J Curtis, Chester J J Wrobel, Bingsen Zhang, Danielle N Maxwell, Judy Y Pan, Frank C Schroeder,

Reactive electrophilic intermediates such as coenzyme A esters play central roles in metabolism but are difficult to detect with conventional strategies. Here, we introduce hydroxylamine-based stable isotope labeling to convert reactive electrophilic intermediates into stable derivatives that are easily detectable via LC-MS. In the model system Caenorhabditis elegans, parallel treatment ... Read more >>

ACS Chem Biol (ACS chemical biology)
[2020, :]

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Deep Interrogation of Metabolism Using a Pathway-Targeted Click-Chemistry Approach.

Jason S Hoki, Henry H Le, Karlie E Mellott, Ying K Zhang, Bennett W Fox, Pedro R Rodrigues, Yan Yu, Maximilian J Helf, Joshua A Baccile, Frank C Schroeder,

Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based ... Read more >>

J Am Chem Soc (Journal of the American Chemical Society)
[2020, :]

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Modular metabolite assembly in C. elegans depends on carboxylesterases and formation of lysosome-related organelles.

Henry H Le, Chester Jj Wrobel, Sarah M Cohen, Jingfang Yu, Heenam Park, Maximilian J Helf, Brian J Curtis, Joseph C Kruempel, Pedro Reis Rodrigues, Patrick J Hu, Paul W Sternberg, Frank C Schroeder,

Signaling molecules derived from attachment of diverse metabolic building blocks to ascarosides play a central role in the life history of C. elegans and other nematodes; however, many aspects of their biogenesis remain unclear. Using comparative metabolomics, we show that a pathway mediating formation of intestinal lysosome-related organelles (LROs) is ... Read more >>

Elife (eLife)
[2020, 9:]

Cited: 0 times

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Toward spatially resolved metabolomics.

Bennett W Fox, Frank C Schroeder,

Nat. Chem. Biol. (Nature chemical biology)
[2020, 16(10):1039-1040]

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Identification of Uric Acid Gluconucleoside-Ascaroside Conjugates in Caenorhabditis elegans by Combining Synthesis and MicroED.

Brian J Curtis, Lee Joon Kim, Chester J J Wrobel, James M Eagan, Rubin A Smith, Jessica E Burch, Henry H Le, Alexander B Artyukhin, Hosea M Nelson, Frank C Schroeder,

Few nucleoside-derived natural products have been identified from animals, despite the ubiquity of nucleosides in living organisms. Here, we use a combination of synthesis and the emerging electron microscopy technique microcrystal electron diffraction to determine the structures of several N3-(β-glucopyranosyl)uric acid derivatives in Caenorhabditis elegans. These noncanonical gluconucleosides further integrate ... Read more >>

Org Lett (Organic letters)
[2020, 22(17):6724-6728]

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Interception of the Bycroft-Gowland Intermediate in the Enzymatic Macrocyclization of Thiopeptides.

Jonathan W Bogart, Nicholas J Kramer, Aneta Turlik, Rachel M Bleich, Daniel S Catlin, Frank C Schroeder, Satish K Nair, R Thomas Williamson, K N Houk, Albert A Bowers,

Thiopeptides are a broad class of macrocyclic, heavily modified peptide natural products that are unified by the presence of a substituted, nitrogen-containing heterocycle core. Early work indicated that this core might be fashioned from two dehydroalanines by an enzyme-catalyzed aza-[4 + 2] cycloaddition to give a cyclic-hemiaminal intermediate. This common ... Read more >>

J Am Chem Soc (Journal of the American Chemical Society)
[2020, 142(30):13170-13179]

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Population Density Modulates the Duration of Reproduction of C. elegans.

Spencer S Wong, Jingfang Yu, Frank C Schroeder, Dennis H Kim,

Population density can modulate the developmental trajectory of Caenorhabditis elegans larvae by promoting entry into dauer diapause, which is characterized by metabolic and anatomical remodeling and stress resistance [1, 2]. Genetic analysis of dauer formation has identified the involvement of evolutionarily conserved endocrine signaling pathways, including the DAF-2/insulin-like receptor signaling ... Read more >>

Curr Biol (Current biology : CB)
[2020, 30(13):2602-2607.e2]

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A neurotransmitter produced by gut bacteria modulates host sensory behaviour.

Michael P O'Donnell, Bennett W Fox, Pin-Hao Chao, Frank C Schroeder, Piali Sengupta,

Animals coexist in commensal, pathogenic or mutualistic relationships with complex communities of diverse organisms, including microorganisms1. Some bacteria produce bioactive neurotransmitters that have previously been proposed to modulate nervous system activity and behaviours of their hosts2,3. However, the mechanistic basis of this microbiota-brain signalling and its physiological relevance are largely ... Read more >>

Nature (Nature)
[2020, 583(7816):415-420]

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Natural diversity in the predatory behavior facilitates the establishment of a robust model strain for nematode-trapping fungi.

Ching-Ting Yang, Guillermo Vidal-Diez de Ulzurrun, A Pedro Gonçalves, Hung-Che Lin, Ching-Wen Chang, Tsung-Yu Huang, Sheng-An Chen, Cheng-Kuo Lai, Isheng J Tsai, Frank C Schroeder, Jason E Stajich, Yen-Ping Hsueh,

Nematode-trapping fungi (NTF) are a group of specialized microbial predators that consume nematodes when food sources are limited. Predation is initiated when conserved nematode ascaroside pheromones are sensed, followed by the development of complex trapping devices. To gain insights into the coevolution of this interkingdom predator-prey relationship, we investigated natural ... Read more >>

Proc. Natl. Acad. Sci. U.S.A. (Proceedings of the National Academy of Sciences of the United States of America)
[2020, 117(12):6762-6770]

Cited: 2 times

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Photoaffinity probes for nematode pheromone receptor identification.

Ying K Zhang, Douglas K Reilly, Jingfang Yu, Jagan Srinivasan, Frank C Schroeder,

Identification of pheromone receptors plays a central role for uncovering signaling pathways that underlie chemical communication in animals. Here, we describe the synthesis and bioactivity of photoaffinity probes for the ascaroside ascr#8, a sex-pheromone of the model nematode, Caenorhabditis elegans. Structure-activity studies guided incorporation of alkyne- and diazirine-moieties and revealed ... Read more >>

Org. Biomol. Chem. (Organic & biomolecular chemistry)
[2019, 18(1):36-40]

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Diketopiperazine Formation in Fungi Requires Dedicated Cyclization and Thiolation Domains.

Joshua A Baccile, Henry H Le, Brandon T Pfannenstiel, Jin Woo Bok, Christian Gomez, Eileen Brandenburger, Dirk Hoffmeister, Nancy P Keller, Frank C Schroeder,

Cyclization of linear dipeptidyl precursors derived from nonribosomal peptide synthetases (NRPSs) into 2,5-diketopiperazines (DKPs) is a crucial step in the biosynthesis of a large number of bioactive natural products. However, the mechanism of DKP formation in fungi has remained unclear, despite extensive studies of their biosyntheses. Here we show that ... Read more >>

Angew Chem Int Ed Engl (Angewandte Chemie (International ed. in English))
[2019, 58(41):14589-14593]

Cited: 1 time

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Co-option of neurotransmitter signaling for inter-organismal communication in C. elegans.

Christopher D Chute, Elizabeth M DiLoreto, Ying K Zhang, Douglas K Reilly, Diego Rayes, Veronica L Coyle, Hee June Choi, Mark J Alkema, Frank C Schroeder, Jagan Srinivasan,

Biogenic amine neurotransmitters play a central role in metazoan biology, and both their chemical structures and cognate receptors are evolutionarily conserved. Their primary roles are in cell-to-cell signaling, as biogenic amines are not normally recruited for communication between separate individuals. Here, we show that in the nematode C. elegans, a ... Read more >>

Nat Commun (Nature communications)
[2019, 10(1):3186]

Cited: 1 time

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Metabolome-Scale Genome-Wide Association Studies Reveal Chemical Diversity and Genetic Control of Maize Specialized Metabolites.

Shaoqun Zhou, Karl A Kremling, Nonoy Bandillo, Annett Richter, Ying K Zhang, Kevin R Ahern, Alexander B Artyukhin, Joshua X Hui, Gordon C Younkin, Frank C Schroeder, Edward S Buckler, Georg Jander,

Cultivated maize (Zea mays) has retained much of the genetic diversity of its wild ancestors. Here, we performed nontargeted liquid chromatography-mass spectrometry metabolomics to analyze the metabolomes of the 282 maize inbred lines in the Goodman Diversity Panel. This analysis identified a bimodal distribution of foliar metabolites. Although 15% of ... Read more >>

Plant Cell (The Plant cell)
[2019, 31(5):937-955]

Cited: 2 times

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Ethylene signaling regulates natural variation in the abundance of antifungal acetylated diferuloylsucroses and Fusarium graminearum resistance in maize seedling roots.

Shaoqun Zhou, Ying K Zhang, Karl A Kremling, Yezhang Ding, John S Bennett, Justin S Bae, Dean K Kim, Hayley H Ackerman, Michael V Kolomiets, Eric A Schmelz, Frank C Schroeder, Edward S Buckler, Georg Jander,

The production and regulation of defensive specialized metabolites play a central role in pathogen resistance in maize (Zea mays) and other plants. Therefore, identification of genes involved in plant specialized metabolism can contribute to improved disease resistance. We used comparative metabolomics to identify previously unknown antifungal metabolites in maize seedling ... Read more >>

New Phytol (The New phytologist)
[2019, 221(4):2096-2111]

Cited: 3 times

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A Single-Neuron Chemosensory Switch Determines the Valence of a Sexually Dimorphic Sensory Behavior.

Kelli A Fagan, Jintao Luo, Ross C Lagoy, Frank C Schroeder, Dirk R Albrecht, Douglas S Portman,

Biological sex, a fundamental dimension of internal state, can modulate neural circuits to generate behavioral variation. Understanding how and why circuits are tuned by sex can provide important insights into neural and behavioral plasticity. Here we find that sexually dimorphic behavioral responses to C. elegans ascaroside sex pheromones are implemented by ... Read more >>

Curr Biol (Current biology : CB)
[2018, 28(6):902-914.e5]

Cited: 9 times

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NRPS-Derived Isoquinolines and Lipopetides Mediate Antagonism between Plant Pathogenic Fungi and Bacteria.

Saima Khalid, Joshua A Baccile, Joseph E Spraker, Joanna Tannous, Muhammad Imran, Frank C Schroeder, Nancy P Keller,

Bacterial-fungal interactions are presumed to be mediated chiefly by small-molecule signals; however, little is known about the signaling networks that regulate antagonistic relationships between pathogens. Here, we show that the ralstonins, lipopeptides produced by the plant pathogenic bacteria Ralstonia solanacearum, interfere with germination of the plant-pathogenic fungus Aspergillus flavus by ... Read more >>

ACS Chem. Biol. (ACS chemical biology)
[2018, 13(1):171-179]

Cited: 7 times

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Detecting the interaction of peptide ligands with plant membrane receptors.

Sarah Refi Hind, Jason S Hoki, Joshua A Baccile, Patrick C Boyle, Frank C Schroeder, Gregory B Martin,

The field of plant receptor biology has rapidly expanded in recent years, however the demonstration of direct interaction between receptor-ligand pairs remains a challenge. Click chemistry has revolutionized small molecule research but lacks popularity in plant research. Here we describe a method that tests for the direct physical interaction of ... Read more >>

Curr Protoc Plant Biol (Current protocols in plant biology)
[2017, 2:240-269]

Cited: 0 times

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Pheromone-sensing neurons regulate peripheral lipid metabolism in Caenorhabditis elegans.

Rosalind Hussey, Jon Stieglitz, Jaleh Mesgarzadeh, Tiffany T Locke, Ying K Zhang, Frank C Schroeder, Supriya Srinivasan,

It is now established that the central nervous system plays an important role in regulating whole body metabolism and energy balance. However, the extent to which sensory systems relay environmental information to modulate metabolic events in peripheral tissues has remained poorly understood. In addition, it has been challenging to map ... Read more >>

PLoS Genet. (PLoS genetics)
[2017, 13(5):e1006806]

Cited: 6 times

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3,7-Isoquinoline quinones from the ascidian tunicate Ascidia virginea.

Sven T Possner, Frank C Schroeder, Hans Tore Rapp, Volker Sinnwell, Stefan Franke, Wittko Francke,

A new isoquinoline quinone system and its iodinated derivatives were isolated from the ascidian tunicate Ascidia virginea Müller 1776 (Phlebobranchia: Ascidiidae). Structures were elucidated by spectroscopic methods and derivatization reactions. Ascidine A (3,7-dihydro-1,8-dihydroxy-4-(4'-hydroxyphenyl)isoquinoline-3,7-dione (1), ascidine B (3,7-dihydro-1,8-dihydroxy-4-(4'-hydroxy-3'-iodophenyl)isoquinoline-3,7-dione (2), and ascidine C (3,7-dihydro-1,8-dihydroxy-4-(4'-hydroxy-3',5'-diiodophenyl)isoquinoline-3,7-dione (3) represent a novel type of tyrosine-derived alkaloids. ... Read more >>

Z. Naturforsch., C, J. Biosci. (Zeitschrift fur Naturforschung. C, Journal of biosciences)
[2017, 72(7-8):259-264]

Cited: 2 times

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Biosynthesis of Modular Ascarosides in C. elegans.

Oishika Panda, Allison E Akagi, Alexander B Artyukhin, Joshua C Judkins, Henry H Le, Parag Mahanti, Sarah M Cohen, Paul W Sternberg, Frank C Schroeder,

The nematode Caenorhabditis elegans uses simple building blocks from primary metabolism and a strategy of modular assembly to build a great diversity of signaling molecules, the ascarosides, which function as a chemical language in this model organism. In the ascarosides, the dideoxysugar ascarylose serves as a scaffold to which diverse ... Read more >>

Angew Chem Int Ed Engl (Angewandte Chemie (International ed. in English))
[2017, 56(17):4729-4733]

Cited: 14 times

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Improved Synthesis for Modular Ascarosides Uncovers Biological Activity.

Ying K Zhang, Marco A Sanchez-Ayala, Paul W Sternberg, Jagan Srinivasan, Frank C Schroeder,

A versatile synthesis of modular ascarosides, a family of signaling molecules from Caenorhabditis elegans and other nematodes, via hydrogenolysis of a cyclic sulfate derived from methyl-α-l-rhamnopyranoside is reported. The route enables selective introduction of different side chains at the 1, 2, and 4 positions of the sugar, as demonstrated for ... Read more >>

Org Lett (Organic letters)
[2017, 19(11):2837-2840]

Cited: 5 times

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Nematophagous fungus Arthrobotrys oligospora mimics olfactory cues of sex and food to lure its nematode prey.

Yen-Ping Hsueh, Matthew R Gronquist, Erich M Schwarz, Ravi David Nath, Ching-Han Lee, Shalha Gharib, Frank C Schroeder, Paul W Sternberg,

To study the molecular basis for predator-prey coevolution, we investigated how Caenorhabditis elegans responds to the predatory fungus Arthrobotrys oligospora. C. elegans and other nematodes were attracted to volatile compounds produced by A. oligospora. Gas-chromatographic mass-spectral analyses of A. oligospora-derived volatile metabolites identified several odors mimicking food cues attractive to ... Read more >>

Elife (eLife)
[2017, 6:]

Cited: 9 times

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Molecular Determinants of the Regulation of Development and Metabolism by Neuronal eIF2α Phosphorylation in Caenorhabditis elegans.

Warakorn Kulalert, Harini Sadeeshkumar, Ying K Zhang, Frank C Schroeder, Dennis H Kim,

Cell-nonautonomous effects of signaling in the nervous system of animals can influence diverse aspects of organismal physiology. We previously showed that phosphorylation of Ser49 of the α-subunit of eukaryotic translation initiation factor 2 (eIF2α) in two chemosensory neurons by PEK-1/PERK promotes entry of Caenorhabditis elegans into dauer diapause. Here, we ... Read more >>

Genetics (Genetics)
[2017, 206(1):251-263]

Cited: 4 times

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Elucidating the Rimosamide-Detoxin Natural Product Families and Their Biosynthesis Using Metabolite/Gene Cluster Correlations.

Ryan A McClure, Anthony W Goering, Kou-San Ju, Joshua A Baccile, Frank C Schroeder, William W Metcalf, Regan J Thomson, Neil L Kelleher,

As microbial genome sequencing becomes more widespread, the capacity of microorganisms to produce an immense number of metabolites has come into better view. Utilizing a metabolite/gene cluster correlation platform, the biosynthetic origins of a new family of natural products, the rimosamides, were discovered. The rimosamides were identified in Streptomyces rimosus ... Read more >>

ACS Chem Biol (ACS chemical biology)
[2016, 11(12):3452-3460]

Cited: 6 times

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Tomato receptor FLAGELLIN-SENSING 3 binds flgII-28 and activates the plant immune system.

Sarah R Hind, Susan R Strickler, Patrick C Boyle, Diane M Dunham, Zhilong Bao, Inish M O'Doherty, Joshua A Baccile, Jason S Hoki, Elise G Viox, Christopher R Clarke, Boris A Vinatzer, Frank C Schroeder, Gregory B Martin,

Plants and animals detect the presence of potential pathogens through the perception of conserved microbial patterns by cell surface receptors. Certain solanaceous plants, including tomato, potato and pepper, detect flgII-28, a region of bacterial flagellin that is distinct from that perceived by the well-characterized FLAGELLIN-SENSING 2 receptor. Here we identify ... Read more >>

Nat Plants (Nature plants)
[2016, 2:16128]

Cited: 35 times

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