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Authors / James B. McAlpine >


Publication / The Untargeted Capability of NMR Helps Recognizing Nefarious Adulteration in Natural Products >

Access: 10.1021/acs.jnatprod.0c01196
authors Seon Beom Kim , Jonathan Bisson ORCID , J. Brent Friesen ORCID , Luca Bucchini , Stefan Gafner , David C. Lankin ORCID , Shao-Nong Chen ORCID , Guido F. Pauli ORCID , James B. McAlpine ORCID
journal Journal of Natural Products (RoMEO status: White)
subjects NMR Adulteration Natural products
Curcuma longa (turmeric) has an extensive history of ethnomedical use for common ailments, and “curcumin”-containing dietary supplements (CDS) are a highly visible portion of today’s self-medication market. Owing to raw material cost pressure, CDS products are affected by economically motivated, nefarious adulteration with synthetic curcumin (“syncumin”), possibly leading to unexpected toxicological issues due to “residual” impurities. Using a combination of targeted and untargeted (phyto)chemical analysis, this study investigated the botanical integrity of two commercial “turmeric” CDS with vitamin and other additives that were associated with reported clinical cases of hepatotoxicity.
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categories publications science

Publication / NMR reveals an undeclared constituent in custom synthetic peptides >

Access: 10.1016/j.jpba.2019.112915
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 Quality control Peptide Adulteration
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

Publication / Quality Control of Therapeutic Peptides by 1H NMR HiFSA Sequencing >

Access: 10.1021/acs.joc.8b02704
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 Quality control Peptide Sequencing
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

Publication / The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research OpenAccess >

Access: 10.1039/C7NP00064B
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 Open Data Natural Products Integrity
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

Publication / Evolution of Quantitative Measures in NMR: Quantum Mechanical qHNMR Advances Chemical Standardization of a Red Clover (Trifolium pratense) Extract OpenAccess >

Access: 10.1021/acs.jnatprod.6b00923
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 Pharmacognosy Phytochemistry NMR qNMR HiFSA
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

Poster / Dissemination of original NMR data enhances the reproducibility of natural product research >

Conference: American Society of Pharmacognosy Annual Meeting, Copper Mountain, Colorado, 25–29 July 2015
subjects Pharmacognosy Phytochemistry NMR FID raw data Spin simulation
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

Publication / Essential Parameters for Structural Analysis and Dereplication by 1H NMR Spectroscopy OpenAccess >

Access: 10.1021/np5002384
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 Pharmacognosy Phytochemistry NMR Spin simulation
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