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Authors: Pierre-Marie AllardORCID , Jonathan BissonORCID , Antonio AzzolliniORCID , Guido F. PauliORCID , Geoffrey A Cordell, Jean-Luc WolfenderORCID
Journal: Current Opinion in Biotechnology (RoMEO status: Green)
Subjects: Pharmacognosy Computers Data Digital Nanopublications Mining Contextualization
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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Authors: Kathryn M. Nelson, Jayme L. Dahlin, Jonathan BissonORCID , James Graham, Guido F. PauliORCID , Michael A. Walters
Journal: Journal of Medicinal Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry Curcumin IMPs PAINS Review
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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Authors: Rasika S. Phansalkar, Charlotte Simmler, Jonathan BissonORCID , Shao-Nong Shen, David C. Lankin, James B. McAlpine, Matthias Niemitz, Guido F. PauliORCID
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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# 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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# Posters/

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

Conference: ICSB-ASP, Oxford, Mississippi, 11–14. April 2016
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Categories: posters
Subjects: NAPRALERT database 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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Authors: Pierre-Marie AllardORCID , Tiphaine Péresse, Jonathan BissonORCID , Katia Gindro, Laurence Marcourt, Van Cuong Pham, Fanny Roussi, Marc Litaudon, Jean-Luc WolfenderORCID
Journal: Analytical Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry MS Fragmentation Molecular Networking Virtual pharmacognosy
Dereplication represents a key step for rapidly identifying known secondary metabolites in complex biological matrices. In this context, liquid-chromatography coupled to high resolution mass spectrometry (LC-HRMS) is increasingly used and, via untargeted data-dependent MS/MS experiments, massive amounts of detailed information on the chemical composition of crude extracts can be generated. An efficient exploitation of such data sets requires automated data treatment and access to dedicated fragmentation databases. Various novel bioinformatics approaches such as molecular networking (MN) and in-silico fragmentation tools have emerged recently and provide new perspective for early metabolite identification in natural products (NPs) research.
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Authors: Guido F. PauliORCID , Matthias Niemitz, Jonathan BissonORCID , Michael W. Lodewyk, Cristian Soldi, Jared T. Shaw, Dean J. Tantillo, Jordy M. Saya, Klaas Vos, Roel A. Kleinnijenhuis, Henk Hiemstra, Shao-Nong Chen, James McAlpine, David C. Lankin, J. Brent Friesen
Journal: Journal of Organic Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry NMR FID raw data Spin simulation
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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Authors: Jonathan BissonORCID , James McAlpine, J. Brent Friesen, Shao-Nong Chen, James Graham, Guido F. PauliORCID
Journal: Journal of Medicinal Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry Perspectives Fundamental research IMP bioactivity data mining NAPRALERT
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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Authors: Ariene A. Leme, Cristina M.P. Vidal, A.B.S. Sousa, Rasika Phansalkar, Joo-Won Nam, Jonathan BissonORCID , Shao-Nong Chen, Guido F. PauliORCID , Ana Bedran-Russo
Journal: Dental Materials (RoMEO status: Green)
Subjects: Pharmacognosy Phytochemistry Dentistry OPAC 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.

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Authors: Joo-Won Nam, Rasika Phansalkar, David C. Lankin, Jonathan BissonORCID , James McAlpine, Ariene A. Leme, Cristina M.P. Vidal, Benjamin Ramirez, Matthias Niemitz, Ana Bedran-Russo, Shao-Nong Chen, Guido F. PauliORCID
Journal: Journal of Organic Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry Dentistry OPAC 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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# 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, Jonathan BissonORCID , James McAlpine, Shao-Nong Chen, Guido F. PauliORCID , Ana Bedran-Russo
Journal: Langmuir (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry Dentistry Polyphenols 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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Authors: Ariene A. Leme, Cristina M.P. Vidal, Thaiane R. Aguiar, A.B.S. Sousa, Rasika Phansalkar, Joo-Won Nam, Jonathan BissonORCID , Shao-Nong Chen, Guido F. PauliORCID , Ana Bedran-Russo
Journal: Dental Materials (RoMEO status: Green)
Subjects: Pharmacognosy Phytochemistry Dentistry OPAC 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.

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Authors: Yorgos Papastamoulis, Jonathan BissonORCID , Hamza Temsamani, Tristan Richard, Axel Marchal, Jean-Michel Mérillon, Pierre Waffo-Téguo
Journal: Tetrahedron (RoMEO status: Green)
Subjects: Pharmacognosy Phytochemistry Vine Wine Stilbenoids Polyphenols CPC Mass Spectrometry
Stilbenoids have received increasing attention over the last two decades since the discovery of resveratrol in wine. With an ever-growing rhythm, a multitude of biological activities of naturally occurring stilbenes are being reported. In this work, we investigated minor stilbenoid compounds from Vitis vinifera stalks. The compounds were purified by means of centrifugal partition chromatography (CPC), a countercurrent-separation technique. Electrospray ionization–ion trap mass spectrometry (ESI–IT-MS) after optimization proved to be extremely efficient for the detection of these new molecules, providing both structural information for structure elucidation and a means to achieve identification even with minute amounts.
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Authors: Thierry Buffeteau, Dominique Cavagnat, Jonathan BissonORCID , Axel Marchal, Gilbert D. Kapche, Ilaria Battistini, Gregory Da Costa, Alain Badoc, Jean-Pierre Monti, Jean-Michel Mérillon, Pierre Waffo-Téguo
Journal: Journal of Natural Products (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry VCD Stereochemistry
Dimeric stilbene glucosides 1–3 [two diastereomers of (−)-gnemonoside A (1a and 1b), (−)-gnemonoside C (2), and (−)-gnemonoside D (3)] as well as a mixture of the two enantiomers of gnetin C (4) were isolated from the rhizomes of Gnetum africanum. The two enantiomers of gnetin C, (+)-4 and (−)-4, were obtained from the aglycones of 1a and 1b, respectively. The configurations of these stilbenoids were investigated by NMR and vibrational circular dichroism (VCD) experiments.
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Authors: Guido F. PauliORCID , Shao-Nong Chen, David C. Lankin, Jonathan BissonORCID , Ryan J. Case, Lucas R. Chadwick, Tanja Gödecke, Taichi Inui, Aleksej Krunic, Birgit U. Jaki, James B. McAlpine, Shunyan Mo, José G. Napolitano, Jimmy Orjala, Juuso Lehtivarjo, Samuli-Petrus Korhonen, Matthias Niemitz
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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Authors: Carole Lambert, Tristan Richard, Elodie Renouf, Jonathan BissonORCID , Pierre Waffo-Téguo, Louis Bordenave, Nathalie Ollat, Jean-Michel Mérillon, Stéphanie Cluzet
Journal: Journal of Agricultural and Food Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry Vine Wine Stilbenoids Polyphenols NMR Mass Spectrometry
Grapevine canes are rich in resveratrol and its complex derivatives. These compounds have many biological activities and are needed mainly for health purposes. Canes, which are often wasted, can be used to produce these high-value compounds at low cost. We studied sixteen Vitis vinifera L. cultivars among the most widely cultivated ones worldwide. Polyphenols were extracted from their canes and identified by liquid chromatography–nuclear magnetic resonance spectroscopy. We accurately determined the content of E-ε-viniferin, E-resveratrol, E-piceatannol, and vitisin B and, for the first time, that of hopeaphenol and miyabenol C.
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Authors: Merian Nassra, Stéphanie Krisa, Yorgos Papastamoulis, Gilbert Deccaux Kapche, Jonathan BissonORCID , Caroline André, Jan-Pieter Konsman, Jean-Marie Schmitter, Jean-Michel Mérillon, Pierre Waffo-Téguo
Journal: Planta Medica (RoMEO status: Blue)
Subjects: Pharmacognosy Phytochemistry Vine Wine Stilbenoids Polyphenols Bioactivity
Microglia-driven inflammatory processes are thought to play an important role in ageing and several neurological disorders. Since consumption of a diet rich in polyphenols has been associated with anti-inflammatory and neuroprotective effects, we studied the effects of twenty-five stilbenoids isolated from Milicia excelsa, Morus alba, Gnetum africanum, and Vitis vinifera. These compounds were tested at 5 and 10 µM on BV-2 microglial cells stimulated with bacterial lipopolysaccharide. Ten stilbenoids reduced lipopolysaccharide-induced nitric oxide production at 5 and/or 10 µM.
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Authors: Alison D. Pawlus, Ramla Sahli, Jonathan BissonORCID , Céline Rivière, Jean-Claude Delaunay, Tristan Richard, Eric Gomès, Louis Bordenave, Pierre Waffo-Téguo, Jean-Michel Mérillon
Journal: Journal of Agricultural and Food Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry Vine Wine Stilbenoids Polyphenols NMR Mass Spectrometry
We present stilbenoid profiles of canes from 16 grapevines. Fifteen stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α]D or as commercial standards. An HPLC–UV method for the simultaneous quantification of nine of these stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V.
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Authors: Carole Lambert, Jonathan BissonORCID , Pierre Waffo-Téguo, Yorgos Papastamoulis, Tristan Richard, Marie-France Corio-Costet, Jean-Michel Mérillon, Stéphanie Cluzet
Journal: Journal of Agricultural and Food Chemistry (RoMEO status: White)
Subjects: Pharmacognosy Phytochemistry Vine Wine Stilbenoids Polyphenols Bioactivity Antifungal
The interaction between Vitis vinifera and trunk disease fungi requires better understanding. We studied the role of phenolics as possible plant defense compounds in this context. The impact of 24 grapevine phenolic compounds was determined on 6 major wood decay fungi by an in vitro agar plate assay. Hydroxystilbenoids, especially oligomers such as miyabenol C, isohopeaphenol, and vitisin A and B, greatly reduced the growth of the fungi, except that of Phaeoacremonium aleophilum.
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