[Bjonnh.net]# _

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: Seon Beom Kim , Jonathan Bisson ORCID , J. Brent Friesen ORCID , Guido F. Pauli ORCID , Charlotte Simmler ORCID
Journal: Journal of Natural Products (RoMEO status: White)
Subjects:
CPC
CCC
Chlorophylls are present in all extracts from the aerial parts of green plant materials. Chlorophylls may act as in vitro bioassay nuisance compounds, possibly preventing the reproducibility and accurate measurement of readouts due to their UV/vis absorbance, fluorescence properties, and tendency to precipitate in aqueous media. Despite the diversity of methods used traditionally to remove chlorophylls, details about their mode of operation, specificity, and reproducibility are scarce. Herein, we report a selective and efficient 45 min liquid–liquid/countercurrent chlorophyll cleanup method using Centrifugal Partition Chromatography (CPC) with a solvent system composed of hexanes–EtOAc–MeOH–water (5:5:5:5, v/v) in elution-extrusion mode.
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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: Pierre-Marie Allard ORCID , Jonathan Bisson ORCID , Antonio Azzollini ORCID , Guido F. Pauli ORCID , Geoffrey A Cordell , Jean-Luc Wolfender ORCID
Journal: Current Opinion in Biotechnology (RoMEO status: Green)
Subjects:
Humans have co-evolved alongside numerous other organisms, some having a profound effect on health and nutrition. As the earliest pharmaceutical subject, pharmacognosy has evolved into a meta-discipline devoted to natural biomedical agents and their functional properties. While the acquisition of expanding data volumes is ongoing, contextualization is lagging. Thus, we assert that the establishment of an integrated and open databases ecosystem will nurture the discipline. After proposing an epistemological framework of knowledge acquisition in pharmacognosy, this study focuses on recent computational and analytical approaches.
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categories publications science
Authors: Kathryn M. Nelson ORCID , Jayme L. Dahlin ORCID , Jonathan Bisson ORCID , James Graham , Guido F. Pauli ORCID , Michael A. Walters ORCID
Journal: Journal of Medicinal Chemistry (RoMEO status: White)
Subjects:
Curcumin is a constituent (up to ∼5%) of the traditional medicine known as turmeric. Interest in the therapeutic use of turmeric and the relative ease of isolation of curcuminoids has led to their extensive investigation. Curcumin has recently been classified as both a PAINS (pan-assay interference compounds) and an IMPS (invalid metabolic panaceas) candidate. The likely false activity of curcumin in vitro and in vivo has resulted in >120 clinical trials of curcuminoids against several diseases.
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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

# Posters/

NAPRALERT, from an historical information silo to a linked resource able to address the new challenges in Natural Products Chemistry and Pharmacognosy.

Abstract from conference NAPRALERT is a database on natural products, including data on ethnobotany, chemistry, pharmacology, toxicology, and clinical trials from literature dating back to the 19th century. Established in 1975 by Norman R. Farnsworth, it became a web accessible resource in 2005 but soon became stagnant while literature grew exponentially. After a complete rewrite of the platform, the focus is now on connecting this resource to the rest of the existing databases and expanding its usability.
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category posters
Authors: Jonathan Bisson ORCID , Charlotte Simmler ORCID , Shao-Nong Chen ORCID , J. Brent Friesen ORCID , David C. Lankin ORCID , James McAlpine , Guido F. Pauli ORCID
Journal: Natural Product Reports (RoMEO status: Yellow)
Subjects:
NMR
The notion of data transparency is gaining a strong awareness among the scientific community. The availability of raw data is actually regarded as a fundamental way to advance science by promoting both integrity and reproducibility of research outcomes. Particularly, in the field of natural product and chemical research, NMR spectroscopy is a fundamental tool for structural elucidation and quantification (qNMR). As such, the accessibility of original NMR data, i.e., Free Induction Decays (FIDs), fosters transparency in chemical research and optimizes both peer review and reproducibility of reports by offering the fundamental tools to perform efficient structural verification.
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categories publications science

# Posters/

Grape Seed Proanthocyanidins: A Novel Source Of Dental Biomaterials And Unique Phytochemistry

Composite-based, tooth colored dental restorations, in spite of their aesthetic appeal, are limited by a short life span. Every subsequent restoration results in the loss of healthy dental tissue. Thus, a bio-mimetic approach has been developed to enhance the mechanical strength of dentin using plant-derived proanthocyanidins (PACs). From a panel of eight active plants, grape seed extract showed the highest dentin biomodification potential, a 15-fold enhancement of dentin stiffness measured in MPa.
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# Posters/

Reviving NAPRALERT and Making It Ready For Improvement and New Challenges In Natural Products Chemistry and Pharmacognosy

NAPRALERT is a database on natural products, including data on the ethnobotany, chemistry, pharmacology, toxicology, and clinical trials. It was established in 1975 by the late Norman R. Farnsworth, at a time when computerized databases were just starting. It became web-accessible in 2005. Due to resource constraints, few enhancements were made to the existing database structure. Now, 10 years later, NAPRALERT faces the challenge of catching-up with other well-established resources.
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category posters
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: Jonathan Bisson ORCID , James McAlpine , J. Brent Friesen ORCID , Shao-Nong Chen ORCID , James Graham , Guido F. Pauli ORCID
Journal: Journal of Medicinal Chemistry (RoMEO status: White)
Subjects:
IMP
High-throughput biology has contributed a wealth of data on chemicals, including natural products (NPs). Recently, attention was drawn to certain, predominantly synthetic, compounds that are responsible for disproportionate percentages of hits but are false actives. Spurious bioassay interference led to their designation as pan-assay interference compounds (PAINS). NPs lack comparable scrutiny, which this study aims to rectify. Systematic mining of 80+ years of the phytochemistry and biology literature, using the NAPRALERT database, revealed that only 39 compounds represent the NPs most reported by occurrence, activity, and distinct activity.
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categories publications science
Authors: Ariene A. Leme , Cristina M.P. Vidal , A.B.S. Sousa , Rasika Phansalkar , Joo-Won Nam ORCID , Jonathan Bisson ORCID , Shao-Nong Chen ORCID , Guido F. Pauli ORCID , Ana Bedran-Russo
Journal: Dental Materials (RoMEO status: Green)
Subjects:
NMR
Plant derived proanthocyanidins are well-established compounds exhibiting high dentin biomodification potency. Among the effects, enhanced tissue biomechanics and biostability are of relevance to restorative dentistry. This study evaluated the adhesive properties of an enriched proanthocyanidin primer on the bond strength of experimental resin-based adhesives containing variable concentrations of HEMA.

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/

Chemical nano shifts explain the NMR fingerprints of dentin-enhancing oligomeric proanthocyanidins

1D NMR spectra contain a wealth of vital structural information that can enhance the description of bioactive molecules. The present study demonstrates how quantum-mechanics driven 1H iterative Full Spin Analysis (QM-HiFSA) is capable of distinguishing spectral detail that cannot be interpreted manually or visually, but provides important information of the 3D structure and bonding (re-)activity of the molecules. This approach is established by analyzing 1D NMR spectra of oligomeric proanthocyanidins (OPACs), which exhibit high dentin bioactivity, and were isolated from the inner bark of pine.
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# 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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# Posters/

K-targeted isolation of C-glycosylflavones from Vitex agnus-castus by countercurrent methodology

C-glycosylated flavones, including orientin, isoorientin, vitexin, and isovitexin, are minor but biologically significant constituents of fruit extracts of the chaste-tree (Vitex agnus-castus L.), a botanical supplement used to treat PMS and postmenopausal symptoms. The partition coefficient, or K-value, is the ratio of the concentration of a compound in each phase of a biphasic solvent mixture and is a physicochemical property of a particular compound in a particular solvent system. This value can be used to predict retention volume (V ret) in a countercurrent separation procedure.
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# Posters/

Minimizing the problems with “PIMPs”

A recent article by Baell(1) on the problems experienced by medicinal chemists with pan-assay interference compounds (PAINS) and Shoichet’s work(2) on the impact of aggregation occurring in high throughput screening libraries, prompts a consideration of how these and other similar problems are experienced by pharmacognosists with promiscuous invalid metabolites as panaceas (PIMPs). Contrary to the classical definition of secondary metabolites as being species specific (or near specific), several natural products, particularly in the more extensively investigated plant kingdom, are common across species, genera, and even families (e.
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Authors: Cristina M.P. Vidal , Ariene A. Leme , Thaiane R. Aguiar , Rasika Phansalkar , Joo-Won Nam ORCID , Jonathan Bisson ORCID , James McAlpine , Shao-Nong Chen ORCID , Guido F. Pauli ORCID , Ana Bedran-Russo
Journal: Langmuir (RoMEO status: White)
Subjects:
NMR
Proanthocyanidins (PACs) are secondary plant metabolites that mediate nonenzymatic collagen cross-linking and enhance the properties of collagen based tissue, such as dentin. The extent and nature of cross-linking is influenced by the composition and specific chemical structure of the bioactive compounds present in certain PAC-rich extracts. This study investigated the effect of the molecular weight and stereochemistry of polyphenol compounds on two important properties of dentin, biomechanics, and biostability. For that, purified phenols, a phenolic acid, and some of its derivatives were selected: PAC dimers (A1, A2, B1, and B2) and a trimer (C1), gallic acid (Ga), its esters methyl-gallate (MGa) and propyl-gallate (PGa), and a pentagalloyl ester of glucose (PGG).
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categories publications science
Authors: Ariene A. Leme , Cristina M.P. Vidal , Thaiane R. Aguiar , A.B.S. Sousa , Rasika Phansalkar , Joo-Won Nam ORCID , Jonathan Bisson ORCID , Shao-Nong Chen ORCID , Guido F. Pauli ORCID , Ana Bedran-Russo
Journal: Dental Materials (RoMEO status: Green)
Subjects:
NMR
The polyphenol source and molecular structure complexity affects interactions of proanthocyanidins (PACs) with dentin matrix. Therefore, this study evaluated the dentin bioactivity of compounds from a non-galloylated PACs-rich extract.

categories publications science
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