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Authors: Kathryn M. Nelson ORCID , Jonathan Bisson ORCID , Gurpreet Singh ORCID , James G. Graham ORCID , Shao-Nong Chen ORCID , J. Brent Friesen ORCID , Jayme L. Dahlin ORCID , Matthias Niemitz ORCID , Michael A. Walters ORCID , Guido F. Pauli ORCID
Journal: Journal of Medicinal Chemistry (RoMEO status: White)
Subjects:
This Perspective of the published essential medicinal chemistry of cannabidiol (CBD) provides evidence that the popularization of CBD-fortified or CBD-labeled health products and CBD-associated health claims lacks a rigorous scientific foundation. CBD’s reputation as a cure-all puts it in the same class as other “natural” panaceas, where valid ethnobotanicals are reduced to single, purportedly active ingredients. Such reductionist approaches oversimplify useful, chemically complex mixtures in an attempt to rationalize the commercial utility of natural compounds and exploit the “natural” label.
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categories publications science
Authors: Mary P. Choules ORCID , Jonathan Bisson ORCID , Charlotte Simmler ORCID , James B. McAlpine ORCID , Gabriel Giancaspro , Anton Bzhelyansky , Matthias Niemitz ORCID , Guido F. Pauli ORCID
Journal: Journal of Pharmaceutical and Biomedical Analysis (RoMEO status: V2)
Subjects:
NMR
Whereas generic, LC-based pharmaceutical control quality procedures depend largely on the detection mode and can be particularly ‘blind’ to certain impurities, NMR is a more versatile and, thus, often more judicious detector. While adulteration presents ever-evolving challenges for the analysis of active pharmaceutical ingredients (APIs) and finished products sold in the worldwide (online) marketplace, research chemicals are usually trusted rather than being considered flawed or even adulterated. This report shows how NMR analysis uncovered the unanticipated presence of substantial amounts of mannitol (20 and 43% w/w) as undeclared constituent in two custom synthetic peptides, DR and DRVYI, that were sourced commercially.
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categories publications science
Authors: Mary P. Choules ORCID , Jonathan Bisson ORCID , Wei Gao , David C. Lankin ORCID , James B. McAlpine ORCID , Matthias Niemitz ORCID , Birgit U. Jaki ORCID , Scott G. Franzblau ORCID , Guido F. Pauli ORCID
Journal: Journal of Organic Chemistry (RoMEO status: White)
Subjects:
NMR
Ensuring identity, purity, and reproducibility are equally essential during synthetic chemistry, drug discovery, and for pharmaceutical product safety. Many peptidic APIs are large molecules that require considerable effort for integrity assurance. This study builds on quantum mechanical 1H iterative Full Spin Analysis (HiFSA) to establish NMR peptide sequencing methodology that overcomes the intrinsic limitations of principal compendial methods in identifying small structural changes or minor impurities that affect effectiveness and safety.
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categories publications science
Authors: James B. McAlpine ORCID , Shao-Nong Chen ORCID , Andrei Kutateladze ORCID , John B. MacMillan , Giovanni Appendino ORCID , Andersson Barison , Mehdi A. Beniddir ORCID , Maique W. Biavatti ORCID , Stefan Bluml , Asmaa Boufridi ORCID , Mark S. Butler ORCID , Robert J. Capon , Young H. Choi , David Coppage , Phillip Crews ORCID , Michael T. Crimmins , Marie Csete ORCID , Pradeep Dewapriya , Joseph M. Egan ORCID , Mary J. Garson , Gregory Genta-Jouve ORCID , William H. Gerwick ORCID , Harald Gross , Mary Kay Harper , Precilia Hermanto , James M. Hook , Luke Hunter , Damien Jeannerat ORCID , Nai-Yun Ji ORCID , Tyler A. Johnson , David G. I. Kingston ORCID , Hiroyuki Koshino , Hsiau-Wei Lee , Guy Lewin , Jie Li ORCID , Roger G. Linington , Miaomiao Liu , Kerry L. McPhail ORCID , Tadeusz F. Molinski ORCID , Bradley S. Moore ORCID , Joo-Won Nam ORCID , Ram P. Neupane , Matthias Niemitz ORCID , Jean-Marc Nuzillard ORCID , Nicholas H. Oberlies ORCID , Fernanda M. M. Ocampos ORCID , Guohui Pan ORCID , Ronald J. Quinn , D. Sai Reddy , Jean-Hugues Renault ORCID , José Rivera-Chávez , Wolfgang Robien ORCID , Carla M. Saunders ORCID , Thomas J. Schmidt ORCID , Christoph Seger , Ben Shen ORCID , Christoph Steinbeck ORCID , Hermann Stuppner , Sonja Sturm , Orazio Taglialatela-Scafati , Dean J. Tantillo ORCID , Robert Verpoorte ORCID , Bin-Gui Wang ORCID , Craig M. Williams ORCID , Philip G. Williams , Julien Wist ORCID , Jian-Min Yue ORCID , Chen Zhang , Zhengren Xu ORCID , Charlotte Simmler ORCID , David C. Lankin ORCID , Jonathan Bisson ORCID , Guido F. Pauli ORCID
Journal: Natural Product Reports (RoMEO status: Yellow)
Subjects:
NMR
With contributions from the global natural product (NP) research community, and continuing the Raw Data Initiative, this review collects a comprehensive demonstration of the immense scientific value of disseminating raw nuclear magnetic resonance (NMR) data, independently of, and in parallel with, classical publishing outlets. A comprehensive compilation of historic to present-day cases as well as contemporary and future applications show that addressing the urgent need for a repository of publicly accessible raw NMR data has the potential to transform natural products (NPs) and associated fields of chemical and biomedical research.
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categories publications science
Authors: Rasika S. Phansalkar , Charlotte Simmler ORCID , Jonathan Bisson ORCID , Shao-Nong Shen , David C. Lankin ORCID , James B. McAlpine ORCID , Matthias Niemitz ORCID , Guido F. Pauli ORCID
Journal: Journal of Natural Products (RoMEO status: White)
Subjects:
NMR
Chemical standardization, along with morphological and DNA analysis ensures the authenticity and advances the integrity evaluation of botanical preparations. Achievement of a more comprehensive, metabolomic standardization requires simultaneous quantitation of multiple marker compounds. Employing quantitative 1H NMR (qHNMR), this study determined the total isoflavone content (TIfCo; 34.5–36.5% w/w) via multimarker standardization and assessed the stability of a 10-year-old isoflavone-enriched red clover extract (RCE). Eleven markers (nine isoflavones, two flavonols) were targeted simultaneously, and outcomes were compared with LC-based standardization.
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categories publications science
Authors: Guido F. Pauli ORCID , Matthias Niemitz ORCID , Jonathan Bisson ORCID , Michael W. Lodewyk , Cristian Soldi , Jared T. Shaw , Dean J. Tantillo ORCID , Jordy M. Saya , Klaas Vos , Roel A. Kleinnijenhuis , Henk Hiemstra , Shao-Nong Chen ORCID , James McAlpine , David C. Lankin ORCID , J. Brent Friesen ORCID
Journal: Journal of Organic Chemistry (RoMEO status: White)
Subjects:
NMR
FID
The revision of the structure of the sesquiterpene aquatolide from a bicyclo[2.2.0]hexane to a bicyclo[2.1.1]hexane structure using compelling NMR data, X-ray crystallography, and the recent confirmation via full synthesis exemplify that the achievement of “structural correctness” depends on the completeness of the experimental evidence. Archived FIDs and newly acquired aquatolide spectra demonstrate that archiving and rigorous interpretation of 1D 1H NMR data may enhance the reproducibility of (bio)chemical research and curb the growing trend of structural misassignments.
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categories publications science
Authors: Joo-Won Nam ORCID , Rasika Phansalkar , David C. Lankin ORCID , Jonathan Bisson ORCID , James McAlpine , Ariene A. Leme , Cristina M.P. Vidal , Benjamin Ramirez , Matthias Niemitz ORCID , Ana Bedran-Russo , Shao-Nong Chen ORCID , Guido F. Pauli ORCID
Journal: Journal of Organic Chemistry (RoMEO status: White)
Subjects:
NMR
The ability of certain oligomeric proanthocyanidins (OPACs) to enhance the biomechanical properties of dentin involves collagen cross-linking of the 1.3–4.5 nm wide space via protein–polyphenol interactions. A systematic interdisciplinary search for the bioactive principles of pine bark has yielded the trimeric PAC, ent-epicatechin-(4β→8)-epicatechin-(2β→O→7,4β→8)-catechin (3), representing the hitherto most potent single chemical entity capable of enhancing dentin stiffness. Building the case from two congeneric PAC dimers, a detailed structural analysis decoded the stereochemistry, spatial arrangement, and chemical properties of three dentin biomodifiers.
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categories publications science

# Posters/

Dissemination of original NMR data enhances the reproducibility of natural product research

The acquisition of 1D 1H NMR (HNMR) spectra is one of earliest steps in characterizing natural products and other organic molecules. For publication, HNMR information usually is “converted” into a table format, and sometimes spectral plots are provided. However, this transformation is lossy and frequently insufficient for unambiguous dereplication. This ambiguity can even lead to structural revision, such as in the recent case of aquatolide (1), a sesquiterpene lactone from Asteriscus aquaticus.
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category posters
Authors: Guido F. Pauli ORCID , Shao-Nong Chen ORCID , David C. Lankin ORCID , Jonathan Bisson ORCID , Ryan J. Case , Lucas R. Chadwick , Tanja Gödecke , Taichi Inui , Aleksej Krunic , Birgit U. Jaki ORCID , James B. McAlpine ORCID , Shunyan Mo , José G. Napolitano , Jimmy Orjala , Juuso Lehtivarjo , Samuli-Petrus Korhonen , Matthias Niemitz ORCID
Journal: Journal of Natural Products (RoMEO status: White)
Subjects:
NMR
The present study demonstrates the importance of adequate precision when reporting the δ and J parameters of frequency domain 1H NMR (HNMR) data. Using a variety of structural classes (terpenoids, phenolics, alkaloids) from different taxa (plants, cyanobacteria), this study develops rationales that explain the importance of enhanced precision in NMR spectroscopic analysis and rationalizes the need for reporting Δδ and ΔJ values at the 0.1–1 ppb and 10 mHz level, respectively.
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categories publications science