Pierre Champy

Université Paris-Saclay

The molecular network-guided exploration of the alkaloid extract of Callichilia inaequalis stems revealed a cluster attributed tentatively to dimeric monoterpene indole alkaloids of the rare criophylline subtype, initiating the dual study reported herein. A patrimonial-themed portion of this work was aimed at performing a spectroscopic reassessment...

Phytochemical investigation of the dichloromethane crude extract from the bark of Ochreinauclea maingayi with the aid of LCMS/MS-based molecular networking guided the isolation and accelerated the elucidation of known and new indole alkaloids. The molecular networking analysis produces two main clusters, along with 41 non-prioritized clusters and s...

Malaria, a disease known for thousands of years and caused by parasites of the Plasmodium genus, continues to cause many deaths throughout the world today, particularly due to the emergence of parasite resistance to the current therapeutic arsenal. Plants of the Strychnos genus, remarkable due to their multiple traditional uses as well as their alk...

This data descriptor reports on the upload to a public repository (GNPS) of the IQAMDB, IsoQuinoline and Annonaceous Metabolites Data Base, comprising 320 tandem mass spectra. This project originated from our in-house collection of isoquinolines. The diversity of compounds included in this database was further extended through the contribution of t...

Introduction: Plants of the genus Strychnos , which include about 200 species, are used for multiple traditional purposes as hunting poison, for example, and have shown interesting pharmacological properties, especially curarizing and tetanizing, but also against malaria. Many monoterpene indole alkaloids have already been isolated and identified....

In less than 10 years, molecular networking (MN) strategy has revolutionized the art of Natural Products (NP) isolation to enter a rational workflow greatly increasing the probabilities of isolating new chemical entities. To pinpoint and streamline the isolation of new Monoterpene Indole Alkaloids (MIAs) in producing plants, we rendered publicly av...

The structure elucidation of theionbrunonine C, a thioether‐bridged dimeric monoterpene indole alkaloid (MIA), and more generally, one of the very few Sulfur‐containing MIA, is reported after its isolation from Mostuea brunonis (Gelsemiaceae). This unstable structure had already been targeted for isolation in our former, molecular network‐guided, i...

Annonaceous acetogenins are natural products held responsible for atypical Parkinsonism due to chronic consumption in traditional medicine or as food, leading to the development of analytical strategies for their complete chemical characterization in complex mixtures. Characterization by tandem mass spectrometry (MS/MS) of acetogenins using collisi...

We herein report on the first chemical assessment of Erythrococca anomala (Juss. ex Poir.) Prain (Euphorbiaceae), a genus that was – to the best of our knowledge – not studied yet from a phytochemical perspective. A molecular networking strategy was implemented to rapidly identify the known specialized metabolites from untargeted MS/MS analyses of...

Hemitheion (1), a new sulfur-containing vobasane-type indole alkaloid, was isolated, together with three known compounds, vobasine (2), gelsedine (3), and gelsemicine (4), from the alkaloid extract of the stems of Mostuea brunonis Didr. (Gelsemiaceae). Compound 1 could be straightforwardly isolated. Its structure was elucidated by a combination of...

Four undescribed alkaloids have been isolated from the bulbs of the previously unstudied Crinum scillifolium. These compounds were targeted following a state-of-the-art molecular networking strategy comprising a dereplication against in silico databases and re-ranking of the candidate structures based on taxonomically informed scoring. The unreport...

The Chemical study of methanolic extract of the seeds from Erythrophleum ivorense led to the isolation of one original cassane diterpenoid (1) along with six known cassane diterpenoids (2–7). In addition, the known compounds (2–7) are isolated for the first time in E. ivorense. Their structures were established according to their spectral data (NMR...

Five new cassane-type diterpenoid heterosides, i. e. two cassane-type amides (1–2), two erythrophlamine-type amine esters (3–4) and a non‑nitrogenous erythrophlamine analogue (5) were isolated from the root barks (1–2) and the seeds (3–5) of Erythrophleum suaveolens. Their structures were unambiguously established by interpretation of their HRESIMS...

Inaequalisines A and B (1 and 2), the first examples of hybrid alkylated phenylpropane monoterpene indole alkaloids, were isolated from the roots of Callichilia inaequalis, guided by the combined use of molecular networking and substructure annotation. Their structures, including absolute configuration, were elucidated by spectroscopic methods and...

Mareya micrantha (Euphorbiaceae) is an Ivorian medicinal plant widely used in gastrointestinal disorders. So as to understand and identify metabolites possibly implicated in the activity of the plant on intestinal muscles, this study has been undertaken. From the crude ethanolic extract EE of the leaves, hexanic (EH), chloromethylene (EC), ethyl ac...

Bioassay guided fractionation of the stem barks of Isolona cooperi led to the isolation of a new lactone, apoprunellelactone (APL, 1), and two known compounds, 5-[1-hydroxyhexyl]-2H-furan-2-one (2) and oleic acid (3). Their structures were elucidated by spectral analysis including MS, UV, IR, 1D and 2D-NMR spectroscopy. Evaluated for its antiprotoz...

Epicatechocorynantheines A and B, and epicatechocorynantheidine were isolated from the stem bark of Corynanthe pachyceras. These molecules were pinpointed, and their isolation streamlined, by a molecular networking strategy. The structural elucidation was unambiguously accomplished from HRMS and 1D/2D NMR data. These compounds represent the first e...

During our research to contribute to the elucidation of the chemical composition of the root bark of E. suaveolens, six non-nitrogenous cassane diterpenoids (1–6) were isolated and identified. Of these secondary metabolites, three have never been previously described: Cassan-13,15-dien-3-oxo-17-oic acid (2), Cassan-15-en-[7,17]-γ-lactone (3) and 6α...

Traditional natural products discovery workflows implying a combination of different targeting strategies including structure-and/or bioactivity-based approaches,afford no information about new compound structure until late in the discovery pipeline. By integrating a MS/MS prediction module and a collaborative library of (bio)chemical transformatio...

The data are related to the research article entitled ''New cassane diterpenoids from the root bark of Erythrophleum suaveolens'' (Jacques et al., 2019). The article provides method of purification and data to determine structure of two novel cassane diterpenoid amines: 3β-hydroxy-3-methylbutanoyloxy-6α-hydroxy-nor-cassamine (1) and 3β-hydroxy-3-me...

Landmark advances in bioinformatics tools have recently enhanced the field of natural products research, putting today's natural product chemists in the enviable position of being able to perform the efficient targeting/discovery of previously undescribed molecules by expediting the prioritization of the isolation workflow. Among these advances, MS...

p>Traditional natural products discovery workflows implying a combination of different targeting strategies including structure- and/or bioactivity-based approaches, afford no information about new compound structure until late in the discovery pipeline. By integrating a MS/MS prediction module and a collaborative library of (bio)chemical transform...

this Data Descriptor announces the submission to public repositories of the monoterpene indole alkaloid database (MIADB), a cumulative collection of 172 tandem mass spectrometry (MS/MS) spectra from multiple research projects conducted in eight natural product chemistry laboratories since the 1960s. All data have been annotated and organized to pro...

Theionbrunonines A and B (1 and 2), the first examples of monoterpene bisindole alkaloids linked by a thioether bridge, were isolated from the stems of Mostuea brunonis, guided by a molecular networking-based dereplication strategy. Their structures were elucidated by a combination of spectroscopic data and ECD calculations. A plausible biosyntheti...

Pleiokomenines A and B (1 and 2), first examples of dimeric aspidofractinine alkaloids linked by a methylene bridge, were isolated from the stem bark of Pleiocarpa mutica. Their structures were elucidated by a combination of spectroscopic analyses and semisynthetic derivatization of pleiocarpinine (3) and a formaldehyde equivalent mediated by scand...

The chemical investigation of the antimalarial plant Phyllanthus fraternus G. L. Webster (Phyllanthaceae) resulted in the discovery of the Securinega alkaloid (+)-allonorsecurinine (1), previously reported as a synthetic compound, together with the known ent-norsecurinine (2), nirurine (3), bubbialine (4), epibubbialine (5) and the lignan phyllanth...

Introduction: Acetogenins are plant polyketides known to be cytotoxic and proposed as antitumor candidates. They are also suspected to be alimentary neurotoxins. Their occurrence as complex mixtures renders their dereplication and structural identification difficult using liquid chromatography coupled to tandem mass spectrometry and efforts are re...

Three new monoterpene indole alkaloids (1–3) have been isolated from the bark of Geissospermum laeve, together with the known alkaloids (−)-leuconolam (4), geissolosimine (5), and geissospermine (6). The structures of 1–3 were elucidated by analysis of their HRMS and NMR spectroscopic data. The absolute configuration of geissolaevine (1) was deduce...

Introduction: Annonaceous acetogenins (AAGs) constitute a group of environmental neurotoxins, possibly implicated in sporadic atypical Parkinsonism/dementia complexes. The recent evidencing of complex mixtures of AAGs in edible fruits and derived food products requires efficient and practical analytical tools for an estimation of human exposure....

Annonaceous acetogenins (AAGs) are neurotoxins possibly responsible for atypical Parkinsonism / dementia clusters, via the consumption of edible Annonaceae fruits. Their presence was investigated in fruit pulps of Annona squamosa from different locations. Qualitative analysis of other AAGs was performed. We here report the identification of squamoc...

Plasminogen activator inhibitor-1 (PAI-1) is the main inhibitor of the tissue type and urokinase type plasminogen activators. High levels of PAI-1 are correlated with an increased risk of thrombotic events and several other pathologies. Despite several compounds with in vitro activity being developed, none of them are currently in clinical use. In...

The use of medicinal plants for the treatment of diseases including malaria is commonplace in Ghanaian traditional medicine, though the therapeutic claims for most plants remain unvalidated. Antiplasmodial activity of the aqueous extracts and successively obtained petroleum ether, ethyl acetate and methanol fractions of the whole Phyllanthus frater...

In the pathogenesis of tauopathies, genetic and environmental factors have been identified. While familial clustering led to the identification of mutations in MAPT encoding the microtubule‐associated protein tau, the high incidence of a sporadic tauopathy endemic in Guadeloupe was linked to the plant‐derived mitochondrial complex I inhibitor annon...

Annonaceous acetogenins (AAGs) are environmental neurotoxins from the fruit pulp of several Annonaceae species, whose consumption was linked to the occurrence of sporadic atypical Parkinsonism with dementia. The quantification of the prototypical AAG annonacin in Rat brain homogenates was performed by UPLC-MS/MS in selected reaction monitoring (SRM...

The Annonaceous acetogenin annonacin is an environmental neurotoxin identified in the pulp of several fruits of the Annonaceae family, whose consumption was linked to the occurrence of sporadic atypical Parkinsonism with dementia. A method for its quantification in Rat brain homogenates by UPLC-MS/MS in selected reaction monitoring (SRM) mode was d...

Résumé Le profil chromatographique des métabolites phytochimiques constitue un outil pour le contrôle de qualité des phytomédicaments africains. Notre objectif était de proposer un protocole de préparation d’échantillon et d’établissement de profil chromatographique liquide des métabolites apolaires pour l’évaluation de la qualité de phytomédicamen...

The Antimalarial Potential of Three Ghanaian Medicinal Plants Objective: Malaria is a major public health problem in Ghana and many indigenes, especially those in rural areas, resort to the use of medicinal plants to treat the disease. The plants: Persea americana Mill. (Lauraceae), Theobroma cacao L. (Malvaceae) and Tridax procumbens (L.) L. (Com...

Annonacin is an environmental neurotoxin identified in the pulp of several fruits of the Annonaceae family (for example in Annona muricata, Asimina triloba), whose consumption was linked with the occurrence of sporadic atypical Parkinsonism with dementia. Pharmacokinetic parameters of this molecule are unknown. A method for its quantification in Ra...

The two new acylphloroglucinol derivatives, methylene-bis-aspidinol AB (1) and mallopposinol (2), together with the nine known compounds, aspidinol B (3), methylene-bis-aspidinol (4), (+)-α-tocopherol (5), lupeol (6), stigmasterol (7), phytol (8), bergenin (9), squalene (11) and methyl gallate (10) were isolated from the leaves of Mallotus oppositi...

Uvaria afzelii Scott Elliot (Annonaceae) is an African traditional medicinal plant. In Ivory Coast, roots of the plant are commonly used as antiparasitic and against others ailments. During our previous investigation on the roots one 1-indanone derivative was obtained together with other compounds that showing interesting antiprotozoal activities....

Phytochemical investigation of the stem bark of Erythrophleum suaveolens yielded four new cassane diterpenoids; 6α-hydroxy-cassamic acid, methyl ester, 4β-carbomethoxy-14-methyltotarol, 6α-hydroxy-nor-cassamine, and 8,9-dehydro-nor-cassamine, along with four known cassane diterpenoids. All structures were elucidated on the basis of one- and two-dim...

Un aperçu des ventes de plantes médicinales et de produits de santé à base de plantes dans différents circuits de distribution en France et aux États-Unis est proposé ici. Il fait suite au bilan dressé dans le numéro 77 de La Phytothérapie Européenne. Ces données, publiées en 2014 par l’Agence Nationale de Sécurité des Médicaments (ANSM), le Syndic...

Curcumin, a natural polyphenolic compound, showed antiparasitic potential, including trypanocidal and leishmanicidal activity, in several in vitro and in vivo models. The molecule is well tolerated in humans. However, it is insoluble in water and displays poor oral bioavailability as a result of low absorption. New derivatives of curcumin were prep...

Four new cassane diterpenoid amides, 1-4 and six known cassane diterpenoid amides have been isolated from the stem bark of Erythrophleum suaveolens. The isolated compounds were subjected to phytochemical investigation. The structures of those compounds were elucidated on the basis of one-and two-dimensional NMR, HRMS and ESIMS analyses. Nor-cassami...

Epidemiological and toxicological studies suggested Annonaceaeous acetogenins to be environmental neurotoxins responsible for sporadic atypical parkinsonism / dementia in tropical areas. These compounds are present in the tropical genus Annona (Annonaceae), known for its fruits-yielding cultivated species such as A. cherimolia. This species is wide...

Cladodes and fruits of Opuntia ficus-indica are used in traditional medicine for the treatment of abscess and skin inflammation. It was therefore interesting to assess whether an antileishmanial activity could be associated to skin healing. This study reports on the antileishmanial activity of Opuntia ficus-indica extracts from cladodes and fruits....

Une enquête ethnobotanique semi-dirigée, focalisée sur le traitement traditionnel des ophtalmies, a été menée auprès de 17 vendeuses de plantes médicinales, issues d’ethnies diverses, installées sur les marchés d’Adjamé et d’Abobo, communes du District d’Abidjan (Côte d’Ivoire). Les pathologies oculaires prises en charge sont notamment les conjonct...

Both genetic and environmental factors likely contribute to the neuropathology of tauopathies, but it remains unclear how specific genetic backgrounds affect the susceptibility towards environmental toxins. Mutations in the tau gene have been associated with familial tauopathies, while annonacin, a plant-derived mitochondrial inhibitor, has been im...

Les huiles essentielles prennent une place croissante dans les armoires à pharmacie domestiques, notamment en raison de la mise sur le marché de produits prêts à l’emploi, d’accès facilité par leur statut généralement non médicamenteux (produits cosmétiques, compléments alimentaires, etc.). En phytothérapie usuelle, l’aromathérapie est traditionnel...

The invention relates to a compound of the following formula (I), or to a pharmaceutically acceptable salt thereof or to a stereoisomer or mixture of stereoisomers at any proportions, where: X1 is a CH2 or C═O group; X2 is a linear saturated or unsaturated carbohydrate chain with 8 to 24 carbon atoms; R1 is a hydrogen atom or an OH or (C1-C6)alkox...

Plusieurs journaux et organismes ont publié cette année un aperçu des ventes de plantes médicinales et de compléments alimentaires à base de plantes dans différents circuits de distribution en France et aux États-Unis. Ces données, fournies par l’Agence Nationale de Sécurité des Médicaments (ANSM), Ethnopharmacologia, HerbalGram, Le Moniteur des Ph...

The quality assessment of African traditional herbal medicinal products is a difficult challenge since they are complex mixtures of several herbal drug or herbal drug preparations. The plant source is also often unknown and/or highly variable. Plant metabolites chromatographic profiling is therefore an important tool for quality control of such her...

The present invention relates to compounds of Formula (I) below, to their pharmaceutically acceptable salts and to their isomers or mixtures of isomers: HetAr—X—CHR1R2 (I) in which: —HetAr represents a group chosen from: —X represents a linear, saturated or unsaturated, hydrocarbon-based chain comprising from 8 to 22 carbon atoms, optionally interr...

Highlights ► Monodora crispata and M. brevipes (Annonaceae) now belong to the Monodoreae tribe. ► Their chemical composition is poorly known. ► 11 benzylisoquinolines, mainly aporphinoids, were obtained from their leaves. ► Presence of 2 morphinandienones was ascertained in M. crispata. ► N,N-dimethylated isoquinolines are proposed as a distinctive...

Dichrostachys cinerea (L.) Wight et Arn. (Fabaceae) root bark is used in Ivorian Traditional Medicine to treat asthma, which is a respiratory disorder characterized by inflammation and the restriction of tracheal muscles obstructing the air circulation. The tracheal relaxant effect of a crude aqueous-alcoholic extract of the plant root bark was pre...

Annonaceous acetogenins (AAGs) are a homogenous class of polyketides proposed as environmental neurotoxins. Previous dereplication studies of AAGs were limited by the use of low-resolution mass spectrometers. Only poor information in terms of structures was provided due to the limited fragmentation of protonated or sodium cationized species. An inn...

Two new unusual 6-furanoflavones, hoslunfuranine (5) and 5-O-methylhoslunfuranine (6), were isolated from the leaves of Hoslundia opposita Vahl.. Four known methylpyranoflavonic analogues [hosloppin (1), hoslundin (2), 5-O-methylhoslundin (3), oppositin (4)], all specific of the species, were also obtained. Their structures were established on the...

Annonacin is a prototypical Annonaceous acetogenin and is proposed as an environmental neurotoxin responsible for Guadeloupean atypical Parkinsonism, via consumption of fruits of Annona muricata L. (soursop). The molecule induces neurodegeneration in several rodent models. Phase 1 metabolism of annonacin was determined in vitro, using Rat and Human...

Annonaceous acetogenins (AAGs) are a homogenous class of polyketides proposed as environmental neurotoxins. Previous dereplication studies of AAGs were limited by the use of low-resolution mass spectrometers. Only poor information in terms of structures was provided due to the limited fragmentation of protonated or sodium cationized species. An inn...

This chapter summarizes toxicological data of acetogenins and reviews the proposition of using them as environmental neurotoxins. Annona squamosa seeds constitute a major source of annonaceous acetogenins (ACGs), which are potent lipophilic complex I inhibitors. Seeds are also often reported as traditional pesticides, and, less frequently, as fish...

Guadeloupean Parkinsonism has been linked epidemiologically to the consumption of Annonaceae fruits. These were proposed to be etiological agents for sporadic atypical Parkinsonism worldwide, because of their content of neurotoxins such as isoquinolinic alkaloids and Annonaceous acetogenins. The pulp of Annona cherimolia Mill. from Spain was screen...

The acetogenin, annonacin, from the tropical annonaceous plant Annona muricata, is a lipophilic, mitochondrial complex I inhibitor reported to be more toxic than rotenone to mesencephalic neurons. The temperate annonaceous plant Asimina triloba (pawpaw) is native to the Eastern United States and products are available online. This study determined...

Les feuilles de Boerhavia diffusa Linn. Sp. (Nyctaginaceae), Baphia nitida Lodd., Cassia occidentalis Linn. Sp., Desmodium adscendens (Sw.) DC. et l’ecorce de racines de Dichrostachys cinerea (L.) Wight et Arn. (Fabaceae) sont traditionnellement utilisees pour traiter l’asthme en Cote d’Ivoire. Les proprietes antispasmodiques de quatre extraits tot...

Leaves of Boerhavia diffusa (Nyctaginaceae), Baphia nitida, Cassia occidentalis, Desmodium adscendens (Fabaceae), and root bark of Dichrostachys cinerea (Fabaceae) are used in Ivory Coast for the treatment of asthma. The aim of this study was to evaluate the potential airway relaxant activity of different extracts of these plants. Extracts of diffe...

Two novel labdane diterpenoids, 15ξ-methoxy-labdan-8(17),11(E),13(14)-trien-15,16-olide (1) and 12(S)-hydroxy-15ξ-methoxy-labdan-8(17),13(14)-dien-15,16-olide (2) were isolated from the rhizomes of Aframomum sceptrum K. Schum (Zingiberaceae). Their structures were established on the basis of their spectroscopic data. Stigmast-4-en-6β-ol-3-one and c...

The antiproliferative activities of six medicinal plant extracts from Burkina Faso were evaluated in order to justify their traditional use for the treatment of cancer. The SOS chromotest method was used in vitro on Escherichia coli PQ37 to evaluate the mutagenic effect of the plant extracts. The DPPH method was used to evaluate the antioxidant act...

The essential oil from the rhizomes of Aframomum sceptrum (Zingiberaceae) was analyzed by GC/MS, and its major constituents were found to be β-pinene (12.7%), caryophyllene oxide (10.0%), and cyperene (6.0%). The oil was also evaluated for antimicrobial activities, in comparison with β-pinene, caryophyllene oxide, and the leaf essential oil of Mela...

Collision-induced dissociation experiments of seven annonaceous acetogenins were carried out under high and low collision energy conditions. Each compound was studied as protonated or deprotonated and lithium- or sodium- cationized molecules, using ElectroSpray Ionisation (ESI) with a hybrid linear trap/orbitrap mass spectrometer (LTQ-Orbitrap®). T...

N-fatty acyl tryptamines constitute a scarce group of natural compounds mainly encountered in Annonaceous plants. No biological activity was reported so far for these rare molecules. This study investigated the neurotrophic properties of these natural tryptaminic derivatives on dopaminergic (DA) neurons in primary mesencephalic cultures. A structur...

Annonaceous acetogenins are proposed as environmental neurotoxicants consumed through medicinal and alimentary habits and responsible for atypical parkinsonian syndromes observed in tropical areas. Potential sources of exposure still have to be determined, as, to date, only a few batches of products for human consumption were searched for these com...

A methylene chloride extract of the pulp of Annona muricata L. was fractionated in search for scarcely functionalized Annonaceous acetogenins (type E). Previously known C-35 and C-37 mono-epoxy unsaturated compounds, epomuricenins-A and -B (1+2) and epomusenins-A and -B (3+4), were obtained. Two new mono-epoxy saturated C-35 representatives, epomur...

Annonacin, a natural lipophilic inhibitor of mitochondrial complex I has been implicated in the etiology of a sporadic neurodegenerative tauopathy in Guadeloupe. We therefore studied further compounds representing the broad biochemical spectrum of complex I inhibitors to which humans are potentially exposed. We determined their lipophilicity, their...

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From the less polar fractions of an Annona squamosa (Annonaceae) seeds extract, four new annonaceous acetogenins, dieposabadelin (1), squamocenin (2), lepirenin (3) and dotistenin (4), were isolated, along with sixteen known acetogenins: corepoxylone, diepomuricanins A and B, dieporeticenine, tripoxyrollin, bullatencin, glabrencin B, reticulatains-...

Basic CH2Cl2 extract of the trunk bark of Cleistopholis patens (Annonaceae) exhibited antifungal activities against Candida albicans, C. parapsilosis, and C. glabrata using an agar well-diffusion assay method. Bioassay-guided fractionation of the extract led to the isolation of 8-hydroxysampangine. The methanolic extract displayed anthelmintic acti...