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Title: Droplet probe: coupling chromatography to the in situ evaluation of the chemistry of nature

Abstract

The chemistry of nature can be beautiful, inspiring, beneficial and poisonous, depending on perspective. Since the isolation of the first secondary metabolites roughly two centuries ago, much of the chemical research on natural products has been both reductionist and static. Typically, compounds were isolated and characterized from the extract of an entire organism from a single time point. While there could be subtexts to that approach, the general premise has been to determine the chemistry with very little in the way of tools to differentiate spatial and/or temporal changes in secondary metabolite profiles. However, the past decade has seen exponential advances in our ability to observe, measure, and visualize the chemistry of nature in situ. Many of those techniques have been reviewed in this journal, and most are tapping into the power of mass spectrometry to analyze a plethora of sample types. In nearly all of the other techniques used to study chemistry in situ, the element of chromatography has been eliminated, instead using various ionization sources to coax ions of the secondary metabolites directly into the mass spectrometer as a mixture. Much of that science has been driven by the great advances in ambient ionization techniques used with amore » suite of mass spectrometry platforms, including the alphabet soup from DESI to LAESI to MALDI. This review discusses the one in situ analysis technique that incorporates chromatography, being the droplet-liquid microjunction-surface sampling probe, which is more easily termed “droplet probe”. In addition to comparing and contrasting the droplet probe with other techniques, we provide perspective on why scientists, particularly those steeped in natural products chemistry training, may want to include chromatography in in situ analyses. Moreover, we provide justification for droplet sampling, especially for samples with delicate and/or non-uniform topographies. Furthermore, while the droplet probe has been used the most in the analysis of fungal cultures, we digest a variety of other applications, ranging from cyanobacteria, to plant parts, and even delicate documents, such as herbarium specimens.« less

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]
  1. Department of Chemistry & Biochemistry, University of North Carolina at Greensboro, Greensboro, USA
  2. Mass Spectrometry and Laser Spectroscopy Group, Chemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, USA
Publication Date:
Research Org.:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1514761
Alternate Identifier(s):
OSTI ID: 1607134
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Published Article
Journal Name:
Natural Product Reports
Additional Journal Information:
Journal Name: Natural Product Reports Journal Volume: 36 Journal Issue: 7; Journal ID: ISSN 0265-0568
Publisher:
Royal Society of Chemistry
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Oberlies, Nicholas H., Knowles, Sonja L., Amrine, Chiraz Soumia M., Kao, Diana, Kertesz, Vilmos, and Raja, Huzefa A. Droplet probe: coupling chromatography to the in situ evaluation of the chemistry of nature. United Kingdom: N. p., 2019. Web. doi:10.1039/C9NP00019D.
Oberlies, Nicholas H., Knowles, Sonja L., Amrine, Chiraz Soumia M., Kao, Diana, Kertesz, Vilmos, & Raja, Huzefa A. Droplet probe: coupling chromatography to the in situ evaluation of the chemistry of nature. United Kingdom. https://doi.org/10.1039/C9NP00019D
Oberlies, Nicholas H., Knowles, Sonja L., Amrine, Chiraz Soumia M., Kao, Diana, Kertesz, Vilmos, and Raja, Huzefa A. Wed . "Droplet probe: coupling chromatography to the in situ evaluation of the chemistry of nature". United Kingdom. https://doi.org/10.1039/C9NP00019D.
@article{osti_1514761,
title = {Droplet probe: coupling chromatography to the in situ evaluation of the chemistry of nature},
author = {Oberlies, Nicholas H. and Knowles, Sonja L. and Amrine, Chiraz Soumia M. and Kao, Diana and Kertesz, Vilmos and Raja, Huzefa A.},
abstractNote = {The chemistry of nature can be beautiful, inspiring, beneficial and poisonous, depending on perspective. Since the isolation of the first secondary metabolites roughly two centuries ago, much of the chemical research on natural products has been both reductionist and static. Typically, compounds were isolated and characterized from the extract of an entire organism from a single time point. While there could be subtexts to that approach, the general premise has been to determine the chemistry with very little in the way of tools to differentiate spatial and/or temporal changes in secondary metabolite profiles. However, the past decade has seen exponential advances in our ability to observe, measure, and visualize the chemistry of nature in situ. Many of those techniques have been reviewed in this journal, and most are tapping into the power of mass spectrometry to analyze a plethora of sample types. In nearly all of the other techniques used to study chemistry in situ, the element of chromatography has been eliminated, instead using various ionization sources to coax ions of the secondary metabolites directly into the mass spectrometer as a mixture. Much of that science has been driven by the great advances in ambient ionization techniques used with a suite of mass spectrometry platforms, including the alphabet soup from DESI to LAESI to MALDI. This review discusses the one in situ analysis technique that incorporates chromatography, being the droplet-liquid microjunction-surface sampling probe, which is more easily termed “droplet probe”. In addition to comparing and contrasting the droplet probe with other techniques, we provide perspective on why scientists, particularly those steeped in natural products chemistry training, may want to include chromatography in in situ analyses. Moreover, we provide justification for droplet sampling, especially for samples with delicate and/or non-uniform topographies. Furthermore, while the droplet probe has been used the most in the analysis of fungal cultures, we digest a variety of other applications, ranging from cyanobacteria, to plant parts, and even delicate documents, such as herbarium specimens.},
doi = {10.1039/C9NP00019D},
journal = {Natural Product Reports},
number = 7,
volume = 36,
place = {United Kingdom},
year = {Wed Jul 17 00:00:00 EDT 2019},
month = {Wed Jul 17 00:00:00 EDT 2019}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1039/C9NP00019D

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Cited by: 21 works
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Works referenced in this record:

Two new cyclopeptides from the co-culture broth of two marine mangrove fungi and their antifungal activity
journal, January 2014


Ambient ionization mass spectrometry: A tutorial
journal, September 2011


Peramine and other fungal alkaloids are exuded in the guttation fluid of endophyte-infected grasses
journal, February 2007


Hypoxyvermelhotins A–C, new pigments from Hypoxylon lechatii sp. nov
journal, February 2014


Verticillin a, a new Anti-Biotic from Verticillium sf.
journal, January 1970


Emerging capabilities of mass spectrometry for natural products
journal, January 2014

  • Jarmusch, Alan K.; Cooks, R. Graham
  • Nat. Prod. Rep., Vol. 31, Issue 6
  • DOI: 10.1039/C3NP70121B

Asimilobin and cis- and trans-Murisolinones, Novel Bioactive Annonaceous Acetogenins from the Seeds of Asimina triloba
journal, October 1995

  • Woo, Mi Hee; Cho, Kyung Yol; Zhang, Yan
  • Journal of Natural Products, Vol. 58, Issue 10
  • DOI: 10.1021/np50124a009

Evaluation of imprint DESI-MS substrates for the analysis of fungal metabolites
journal, January 2015

  • Tata, Alessandra; Perez, Consuelo J.; Ore, Moriam O.
  • RSC Advances, Vol. 5, Issue 92
  • DOI: 10.1039/C5RA12805F

Review of operating principle and applications of the charged aerosol detector
journal, March 2010


Evaluation of Various Parts of the Paw Paw Tree, Asimina Triloba (Annonaceae), as Commercial Sources of the Pesticidal Annonaceous Acetogenins
journal, December 1992

  • Ratnayake, Sunil; Rupprecht, Kent J.; Potter, William M.
  • Journal of Economic Entomology, Vol. 85, Issue 6
  • DOI: 10.1093/jee/85.6.2353

Countercurrent Separation of Natural Products #
journal, August 2008

  • Pauli, Guido F.; Pro, Samuel M.; Friesen, J. Brent
  • Journal of Natural Products, Vol. 71, Issue 8
  • DOI: 10.1021/np800144q

Natural and engineered biosynthesis of fluorinated natural products
journal, January 2014

  • Walker, Mark C.; Chang, Michelle C. Y.
  • Chem. Soc. Rev., Vol. 43, Issue 18
  • DOI: 10.1039/C4CS00027G

Desorption electrospray ionization mass spectrometry reveals surface-mediated antifungal chemical defense of a tropical seaweed
journal, April 2009

  • Lane, A. L.; Nyadong, L.; Galhena, A. S.
  • Proceedings of the National Academy of Sciences, Vol. 106, Issue 18
  • DOI: 10.1073/pnas.0812020106

Phylogenetic and chemical diversity of fungal endophytes isolated from Silybum marianum (L) Gaertn. (milk thistle)
journal, January 2015


Metabolite induction via microorganism co-culture: A potential way to enhance chemical diversity for drug discovery
journal, November 2014


Chemical ecology of fungi
journal, January 2015


Annonaceous Acetogenins:  Recent Progress
journal, March 1999

  • Alali, Feras Q.; Liu, Xiao-Xi; McLaughlin, Jerry L.
  • Journal of Natural Products, Vol. 62, Issue 3
  • DOI: 10.1021/np980406d

Recent advances in engineering nonribosomal peptide assembly lines
journal, January 2016

  • Winn, M.; Fyans, J. K.; Zhuo, Y.
  • Natural Product Reports, Vol. 33, Issue 2
  • DOI: 10.1039/C5NP00099H

New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii : Diketopiperazine dimer
journal, June 2015

  • Kaur, Amninder; Raja, Huzefa A.; Darveaux, Blaise A.
  • Magnetic Resonance in Chemistry, Vol. 53, Issue 8
  • DOI: 10.1002/mrc.4254

ω-Hydroxyemodin Limits Staphylococcus aureus Quorum Sensing-Mediated Pathogenesis and Inflammation
journal, February 2015

  • Daly, Seth M.; Elmore, Bradley O.; Kavanaugh, Jeffrey S.
  • Antimicrobial Agents and Chemotherapy, Vol. 59, Issue 4
  • DOI: 10.1128/AAC.04564-14

Mapping the Fungal Battlefield: Using in situ Chemistry and Deletion Mutants to Monitor Interspecific Chemical Interactions Between Fungi
journal, February 2019

  • Knowles, Sonja L.; Raja, Huzefa A.; Wright, Allison J.
  • Frontiers in Microbiology, Vol. 10
  • DOI: 10.3389/fmicb.2019.00285

Fungi-derived lipopeptide antibiotics developed since 2000
journal, March 2019


Triggering cryptic natural product biosynthesis in microorganisms
journal, January 2009

  • Scherlach, Kirstin; Hertweck, Christian
  • Organic & Biomolecular Chemistry, Vol. 7, Issue 9
  • DOI: 10.1039/b821578b

Ion formation mechanisms in UV-MALDI
journal, January 2006


De Novo Production of Metabolites by Fungal Co-culture of Trichophyton rubrum and Bionectria ochroleuca
journal, May 2013

  • Bertrand, Samuel; Schumpp, Olivier; Bohni, Nadine
  • Journal of Natural Products, Vol. 76, Issue 6
  • DOI: 10.1021/np400258f

Ion Formation in MALDI:  The Cluster Ionization Mechanism
journal, February 2003

  • Karas, Michael; Krüger, Ralf
  • Chemical Reviews, Vol. 103, Issue 2
  • DOI: 10.1021/cr010376a

Eight New Peptaibols from Sponge-Associated Trichoderma atroviride
journal, December 2013

  • Panizel, Irina; Yarden, Oded; Ilan, Micha
  • Marine Drugs, Vol. 11, Issue 12
  • DOI: 10.3390/md11124937

Formation of exudate droplets by Metarhizium anisopliae and the presence of destruxins
journal, January 2010

  • Hutwimmer, Stefan; Wang, Hui; Strasser, Hermann
  • Mycologia, Vol. 102, Issue 1
  • DOI: 10.3852/09-079

Nonribosomal Peptide Synthesis-Principles and Prospects
journal, March 2017

  • Süssmuth, Roderich D.; Mainz, Andi
  • Angewandte Chemie International Edition, Vol. 56, Issue 14
  • DOI: 10.1002/anie.201609079

Mass spectrometry imaging under ambient conditions
journal, September 2012

  • Wu, Chunping; Dill, Allison L.; Eberlin, Livia S.
  • Mass Spectrometry Reviews, Vol. 32, Issue 3
  • DOI: 10.1002/mas.21360

Fungal secondary metabolism — from biochemistry to genomics
journal, December 2005

  • Keller, Nancy P.; Turner, Geoffrey; Bennett, Joan W.
  • Nature Reviews Microbiology, Vol. 3, Issue 12, p. 937-947
  • DOI: 10.1038/nrmicro1286

Asitrilobins C and D: two new cytotoxic mono-tetrahydrofuran annonaceous acetogenins from Asimina triloba seeds
journal, January 2000


Corona-Charged Aerosol Detection: An Analytical Approach
journal, May 2013

  • Ligor, Magdalena; Studzińska, Sylwia; Horna, Aleš
  • Critical Reviews in Analytical Chemistry, Vol. 43, Issue 2
  • DOI: 10.1080/10408347.2012.746134

Fungal Identification Using Molecular Tools: A Primer for the Natural Products Research Community
journal, February 2017


Peptaibols, Tetramic Acid Derivatives, Isocoumarins, and Sesquiterpenes from a Bionectria sp. (MSX 47401)
journal, May 2013

  • Figueroa, Mario; Raja, Huzefa; Falkinham, Joseph O.
  • Journal of Natural Products, Vol. 76, Issue 6
  • DOI: 10.1021/np3008842

Ambient molecular imaging by desorption electrospray ionization mass spectrometry
journal, March 2008

  • Wiseman, Justin M.; Ifa, Demian R.; Venter, Andre
  • Nature Protocols, Vol. 3, Issue 3
  • DOI: 10.1038/nprot.2008.11

Scanning Capillary Microscopy/Mass Spectrometry for Mapping Spatial Electrochemical Activity of Electrodes
journal, July 2001

  • Modestov, Alexander D.; Srebnik, Simcha; Lev, Ovadia
  • Analytical Chemistry, Vol. 73, Issue 17
  • DOI: 10.1021/ac001369+

Prealamethicin F50 and related peptaibols from Trichoderma arundinaceum: validation of their authenticity via in situ chemical analysis
journal, January 2017

  • Rivera-Chávez, José; Raja, Huzefa A.; Graf, Tyler N.
  • RSC Adv., Vol. 7, Issue 72
  • DOI: 10.1039/C7RA09602J

Chemical Epigenetics Alters the Secondary Metabolite Composition of Guttate Excreted by an Atlantic-Forest-Soil-Derived Penicillium citreonigrum
journal, May 2010

  • Wang, Xiaoru; Sena Filho, José G.; Hoover, Ashley R.
  • Journal of Natural Products, Vol. 73, Issue 5
  • DOI: 10.1021/np100142h

Enhancement of antibiotic and secondary metabolite detection from filamentous fungi by growth on nutritional arrays
journal, June 2008


Cytotoxic and Antihaptotactic Beauvericin Analogues from Precursor-Directed Biosynthesis with the Insect Pathogen Beauveria bassiana ATCC 7159
journal, September 2007

  • Xu, Yuquan; Zhan, Jixun; Wijeratne, E. M. Kithsiri
  • Journal of Natural Products, Vol. 70, Issue 9
  • DOI: 10.1021/np070262f

Ambient Mass Spectrometry
journal, March 2006


Editorial: EDITORIAL
journal, November 2003

  • Brückner, Hans
  • Journal of Peptide Science, Vol. 9, Issue 11-12
  • DOI: 10.1002/psc.536

Thin-Layer Chromatography and Electrospray Mass Spectrometry Coupled Using a Surface Sampling Probe
journal, November 2002

  • Van Berkel, Gary J.; Sanchez, Amaury D.; Quirke, J. Martin E.
  • Analytical Chemistry, Vol. 74, Issue 24
  • DOI: 10.1021/ac020540+

Asitrilobins A and B: cytotoxic mono-THF Annonaceous acetogenins from the seeds of Asimina triloba
journal, March 1999


Imprint Desorption Electrospray Ionization Mass Spectrometry Imaging for Monitoring Secondary Metabolites Production during Antagonistic Interaction of Fungi
journal, November 2015


Fully automated liquid extraction-based surface sampling and ionization using a chip-based robotic nanoelectrospray platform
journal, March 2010

  • Kertesz, Vilmos; Van Berkel, Gary J.
  • Journal of Mass Spectrometry, Vol. 45, Issue 3
  • DOI: 10.1002/jms.1709

Electrospray Device for Coupling Microscale Separations and Other Miniaturized Devices with Electrospray Mass Spectrometry
journal, February 2001

  • Wachs, Timothy; Henion, Jack
  • Analytical Chemistry, Vol. 73, Issue 3
  • DOI: 10.1021/ac000935y

Mycotoxins
journal, July 2003


Acetophenone derivatives from a freshwater fungal isolate of recently described Lindgomyces madisonensis (G416)
journal, June 2016


Evaluation of a surface-sampling probe electrospray mass spectrometry system for the analysis of surface-deposited and affinity-captured proteins
journal, January 2006

  • Van Berkel, Gary J.; Ford, Michael J.; Doktycz, Mitchel J.
  • Rapid Communications in Mass Spectrometry, Vol. 20, Issue 7
  • DOI: 10.1002/rcm.2428

Mevalocidin: A Novel, Phloem Mobile Phytotoxin from Fusarium DA056446 and Rosellinia DA092917
journal, January 2013

  • Gerwick, B. Clifford; Brewster, William K.; deBoer, Gerrit J.
  • Journal of Chemical Ecology, Vol. 39, Issue 2
  • DOI: 10.1007/s10886-013-0238-7

Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae
journal, September 2012

  • Figueroa, Mario; Graf, Tyler N.; Ayers, Sloan
  • The Journal of Antibiotics, Vol. 65, Issue 11
  • DOI: 10.1038/ja.2012.69

Contrasting roles of H3K4me3 and H3K9me3 in regulation of apoptosis and gemcitabine resistance in human pancreatic cancer cells
journal, February 2018


Indoor fungal composition is geographically patterned and more diverse in temperate zones than in the tropics
journal, June 2010

  • Amend, A. S.; Seifert, K. A.; Samson, R.
  • Proceedings of the National Academy of Sciences, Vol. 107, Issue 31
  • DOI: 10.1073/pnas.1000454107

Co-Cultivation—A Powerful Emerging Tool for Enhancing the Chemical Diversity of Microorganisms
journal, February 2014

  • Marmann, Andreas; Aly, Amal; Lin, Wenhan
  • Marine Drugs, Vol. 12, Issue 2
  • DOI: 10.3390/md12021043

Expanding the Fluorine Chemistry of Living Systems Using Engineered Polyketide Synthase Pathways
journal, September 2013


Total Synthesis of (+)-11,11'-Dideoxyverticillin A
journal, April 2009


Imaging mass spectrometry in microbiology
journal, August 2011

  • Watrous, Jeramie D.; Dorrestein, Pieter C.
  • Nature Reviews Microbiology, Vol. 9, Issue 9
  • DOI: 10.1038/nrmicro2634

The MLL1-H3K4me3 Axis-Mediated PD-L1 Expression and Pancreatic Cancer Immune Evasion
journal, January 2017

  • Lu, Chunwan; Paschall, Amy V.; Shi, Huidong
  • Journal of the National Cancer Institute, Vol. 109, Issue 6
  • DOI: 10.1093/jnci/djw283

The evolving field of imaging mass spectrometry and its impact on future biological research
journal, January 2011

  • Watrous, Jeramie D.; Alexandrov, Theodore; Dorrestein, Pieter C.
  • Journal of Mass Spectrometry, Vol. 46, Issue 2
  • DOI: 10.1002/jms.1876

Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids
journal, January 2013

  • Boyer, Nicolas; Morrison, Karen C.; Kim, Justin
  • Chemical Science, Vol. 4, Issue 4
  • DOI: 10.1039/c3sc50174d

An ecological perspective of microbial secondary metabolism
journal, August 2011


Epigenetic manipulation of a filamentous fungus by the proteasome-inhibitor bortezomib induces the production of an additional secondary metabolite
journal, January 2014

  • VanderMolen, Karen M.; Darveaux, Blaise A.; Chen, Wei-Lun
  • RSC Adv., Vol. 4, Issue 35
  • DOI: 10.1039/C4RA00274A

Fungal Fragments as Indoor Air Biocontaminants
journal, July 2002


Calothrixamides A and B from the Cultured Cyanobacterium Calothrix sp. UIC 10520
journal, September 2018


Reactive desorption electrospray ionization mass spectrometry (DESI-MS) of natural products of a marine alga
journal, March 2009

  • Nyadong, Leonard; Hohenstein, Edward G.; Galhena, Asiri
  • Analytical and Bioanalytical Chemistry, Vol. 394, Issue 1
  • DOI: 10.1007/s00216-009-2674-3

Importance of secondary metabolites in the Xylariaceae as parameters for
journal, October 2011

  • Stadler, Marc
  • Current Research in Environmental & Applied Mycology, Vol. 1, Issue 2
  • DOI: 10.5943/cream/1/2/1

The Peptaibiotics Database - A Comprehensive Online Resource
journal, May 2015

  • Neumann, Nora K. N.; Stoppacher, Norbert; Zeilinger, Susanne
  • Chemistry & Biodiversity, Vol. 12, Issue 5
  • DOI: 10.1002/cbdv.201400393

Biosynthesis of Fluorinated Peptaibols Using a Site-Directed Building Block Incorporation Approach
journal, June 2017


Dereplication of microbial extracts and related analytical technologies
journal, February 2014

  • Ito, Tatsuya; Masubuchi, Miyako
  • The Journal of Antibiotics, Vol. 67, Issue 5
  • DOI: 10.1038/ja.2014.12

Paw Paw and Cancer: Annonaceous Acetogenins from Discovery to Commercial Products
journal, July 2008

  • McLaughlin, Jerry L.
  • Journal of Natural Products, Vol. 71, Issue 7
  • DOI: 10.1021/np800191t

Cephaibols, New Peptaibol Antibiotics with Anthelmintic Properties from Acremonium tubakii DSM 12774.
journal, January 2001


Biologically active acetogenins from stem bark of Asimina triloba
journal, July 1993


Camptothecin and Taxol:  Historic Achievements in Natural Products Research
journal, February 2004

  • Oberlies, Nicholas H.; Kroll, David J.
  • Journal of Natural Products, Vol. 67, Issue 2
  • DOI: 10.1021/np030498t

A concise review of mass spectrometry imaging
journal, June 2010

  • Amstalden van Hove, Erika R.; Smith, Donald F.; Heeren, Ron M. A.
  • Journal of Chromatography A, Vol. 1217, Issue 25
  • DOI: 10.1016/j.chroma.2010.01.033

Peptaibiotics
journal, June 2007


Dereplication: racing to speed up the natural products discovery process
journal, January 2015

  • Gaudêncio, Susana P.; Pereira, Florbela
  • Natural Product Reports, Vol. 32, Issue 6
  • DOI: 10.1039/C4NP00134F

Laser Ablation Electrospray Ionization for Atmospheric Pressure, in Vivo, and Imaging Mass Spectrometry
journal, November 2007

  • Nemes, Peter; Vertes, Akos
  • Analytical Chemistry, Vol. 79, Issue 21
  • DOI: 10.1021/ac071181r

Enhanced dereplication of fungal cultures via use of mass defect filtering
journal, January 2017

  • Paguigan, Noemi D.; El-Elimat, Tamam; Kao, Diana
  • The Journal of Antibiotics, Vol. 70, Issue 5
  • DOI: 10.1038/ja.2016.145

Genome Mining for Novel Natural Product Discovery
journal, May 2008

  • Challis, Gregory L.
  • Journal of Medicinal Chemistry, Vol. 51, Issue 9
  • DOI: 10.1021/jm700948z

Optimizing production and evaluating biosynthesis in situ of a herbicidal compound, mevalocidin, from Coniolariella sp.
journal, May 2016

  • Sica, Vincent P.; Figueroa, Mario; Raja, Huzefa A.
  • Journal of Industrial Microbiology & Biotechnology, Vol. 43, Issue 8
  • DOI: 10.1007/s10295-016-1782-2

High-Resolution MS, MS/MS, and UV Database of Fungal Secondary Metabolites as a Dereplication Protocol for Bioactive Natural Products
journal, August 2013

  • El-Elimat, Tamam; Figueroa, Mario; Ehrmann, Brandie M.
  • Journal of Natural Products, Vol. 76, Issue 9
  • DOI: 10.1021/np4004307

Additional bioactive annonaceous acetogenins from Asimina triloba (Annonaceae)
journal, March 1997


The use of secondary metabolite profiling in chemotaxonomy of filamentous fungi
journal, February 2008


Biological variation of microbial metabolites by precursor-directed biosynthesis
journal, January 1993


Imaging mass spectrometry of natural products
journal, January 2009

  • Esquenazi, Eduardo; Yang, Yu-Liang; Watrous, Jeramie
  • Natural Product Reports, Vol. 26, Issue 12
  • DOI: 10.1039/b915674g

Are we ready for industrial production of bioactive plant secondary metabolites utilizing endophytes?
journal, January 2011

  • Kusari, Souvik; Spiteller, Michael
  • Natural Product Reports, Vol. 28, Issue 7
  • DOI: 10.1039/c1np00030f

Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia
journal, May 1971

  • Wani, Mansukhlal C.; Taylor, Harold Lawrence; Wall, Monroe E.
  • Journal of the American Chemical Society, Vol. 93, Issue 9
  • DOI: 10.1021/ja00738a045

High-Throughput Mode Liquid Microjunction Surface Sampling Probe
journal, August 2009

  • Van Berkel, Gary J.; Kertesz, Vilmos; King, Richard C.
  • Analytical Chemistry, Vol. 81, Issue 16
  • DOI: 10.1021/ac901098d

Evaporative light scattering detection: trends in its analytical uses
journal, June 2007

  • Lucena, R.; Cárdenas, S.; Valcárcel, M.
  • Analytical and Bioanalytical Chemistry, Vol. 388, Issue 8
  • DOI: 10.1007/s00216-007-1344-6

Dereplication of macrocyclic trichothecenes from extracts of filamentous fungi through UV and NMR profiles
journal, July 2010

  • Sy-Cordero, Arlene A.; Graf, Tyler N.; Wani, Mansukh C.
  • The Journal of Antibiotics, Vol. 63, Issue 9
  • DOI: 10.1038/ja.2010.77

H3K9 Trimethylation Silences Fas Expression To Confer Colon Carcinoma Immune Escape and 5-Fluorouracil Chemoresistance
journal, July 2015

  • Paschall, Amy V.; Yang, Dafeng; Lu, Chunwan
  • The Journal of Immunology, Vol. 195, Issue 4
  • DOI: 10.4049/jimmunol.1402243

Plasma pharmacokinetics and bioavailability of verticillin A following different routes of administration in mice using liquid chromatography tandem mass spectrometry
journal, May 2017

  • Wang, Jiang; Zhu, Xiaohua; Kolli, Shamala
  • Journal of Pharmaceutical and Biomedical Analysis, Vol. 139
  • DOI: 10.1016/j.jpba.2017.02.051

Structures of eleven zervamicin and two emerimicin peptide antibiotics studied by fast atom bombardment mass spectrometry
journal, October 1981

  • Rinehart, Kenneth L.; Gaudioso, Larry A.; Moore, Michael L.
  • Journal of the American Chemical Society, Vol. 103, Issue 21
  • DOI: 10.1021/ja00411a052

OSMAC approach leads to new fusarielin metabolites from Fusarium tricinctum
journal, March 2017

  • Hemphill, Catalina F. Pérez; Sureechatchaiyan, Parichat; Kassack, Matthias U.
  • The Journal of Antibiotics, Vol. 70, Issue 6
  • DOI: 10.1038/ja.2017.21

Biogenetically-Inspired Total Synthesis of Epidithiodiketopiperazines and Related Alkaloids
journal, April 2015

  • Kim, Justin; Movassaghi, Mohammad
  • Accounts of Chemical Research, Vol. 48, Issue 4
  • DOI: 10.1021/ar500454v

Chemical Aspects of the Extractive Methods of Ambient Ionization Mass Spectrometry
journal, April 2013


Twenty Years of Evaporative Light Scattering Detection
journal, October 2005

  • Megoulas, Nikolaos C.; Koupparis, Michael A.
  • Critical Reviews in Analytical Chemistry, Vol. 35, Issue 4
  • DOI: 10.1080/10408340500431306

Dereplicating and Spatial Mapping of Secondary Metabolites from Fungal Cultures in Situ
journal, July 2015


Fungus wars: basidiomycete battles in wood decay
journal, March 2018


Non-destructive chemical analysis of a Garcinia mangostana L. (Mangosteen) herbarium voucher specimen
journal, December 2018


Mass spectrometry imaging of secondary metabolites directly on fungal cultures
journal, January 2014

  • Sica, V. P.; Raja, H. A.; El-Elimat, T.
  • RSC Adv., Vol. 4, Issue 108
  • DOI: 10.1039/C4RA11564C

Mass Spectrometry Sampling Under Ambient Conditions with Desorption Electrospray Ionization
journal, October 2004


Spatial and Temporal Profiling of Griseofulvin Production in Xylaria cubensis Using Mass Spectrometry Mapping
journal, April 2016


Countercurrent Separation of Natural Products: An Update
journal, June 2015

  • Friesen, J. Brent; McAlpine, James B.; Chen, Shao-Nong
  • Journal of Natural Products, Vol. 78, Issue 7
  • DOI: 10.1021/np501065h

Media studies to enhance the production of verticillins facilitated by in situ chemical analysis
journal, September 2018

  • Amrine, Chiraz Soumia M.; Raja, Huzefa A.; Darveaux, Blaise A.
  • Journal of Industrial Microbiology & Biotechnology, Vol. 45, Issue 12
  • DOI: 10.1007/s10295-018-2083-8

Liquid microjunction surface sampling probe electrospray mass spectrometry for detection of drugs and metabolites in thin tissue sections
journal, April 2008

  • Van Berkel, Gary J.; Kertesz, Vilmos; Koeplinger, Kenneth A.
  • Journal of Mass Spectrometry, Vol. 43, Issue 4
  • DOI: 10.1002/jms.1340

Induced Production of N -Formyl Alkaloids from Aspergillus fumigatus by Co-culture with Streptomyces peucetius
journal, July 2011

  • Zuck, Karina M.; Shipley, Suzanne; Newman, David J.
  • Journal of Natural Products, Vol. 74, Issue 7
  • DOI: 10.1021/np200255f