Charlotte Simmler

Institut Méditerranéen de Biodiversité et d'Ecologie Marine et Continentale | IMBE · Diversity and Functioning from Molecules to Ecosystems

Aloe plant species have been used for centuries in traditional medicine and are reported to be an important source of natural products. However, despite the large number of species within the Aloe genus, only a few have been investigated chemotaxonomically. A Molecular Network approach was used to highlight the different chemical classes characteri...

Sponges are prolific producers of specialized metabolites with unique structural scaffolds. Their chemical diversity has always inspired natural product chemists working in drug discovery. As part of their metabolic filter-feeding activities, sponges are known to release molecules, possibly including their specialized metabolites. These released "E...

The wastewater from hospitals, pharmaceutical industries and more generally human and animal dejections leads to environmental releases of antibiotics that cause severe problems for all living organisms. The aim of this study was to investigate the capacity of three fungal strains to biotransform the fluoroquinolone levofloxacin. The degradation pr...

An extract from Artemisia dracunculus L. (termed PMI-5011) improves glucose homeostasis by enhancing insulin action and reducing ectopic lipid accumulation, while increasing fat oxidation in skeletal muscle tissue in obese insulin resistant male mice. A chalcone, DMC-2, in PMI-5011 is the major bioactive that enhances insulin signaling and activati...

Many botanicals used for women's health contain estrogenic (iso)flavonoids. The literature suggests that estrogen receptor beta (ERβ) activity can counterbalance estrogen receptor alpha (ERα)-mediated proliferation, thus providing a better safety profile. A structure-activity relationship study of (iso)flavonoids was conducted to identify ERβ-prefe...

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 diversi...

Complementing classical drug discovery, phytochemicals act on multiple pharmacological targets, especially in botanical extracts, where they form complex bioactive mixtures. The reductionist approach used in bioactivity-guided fractionation to identify single bioactive phytochemicals is inadequate for capturing the full therapeutic potential of the...

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 finish...

Occurring in hops (Humulus lupulus) and beer as a racemic mixture, (2R,2S)-8-prenylnaringenin (8-PN) is a potent phytoestrogen in hop dietary supplements used by women as alternatives to conventional hormone therapy. With a half-life exceeding 20 h, 8-PN is excreted primarily as 8-PN-7-O-glucuronide or 8-PN-4’-O-glucuronide. Human liver microsomes...

Correction for ‘The value of universally available raw NMR data for transparency, reproducibility, and integrity in natural product research’ by James B. McAlpine et al. , Nat. Prod. Rep. , 2018, DOI: 10.1039/c7np00064b.

Women are increasingly using botanical dietary supplements (BDS) to reduce menopausal hot flashes. While licorice (Glycyrrhiza sp.) is one of the frequently used ingredients in BDSs, the exact plant species is often not identified. We previously showed that in breast epithelial cells (MCF-10A), Glycyrrhiza glabra (GG) and G. inflata (GI), and their...

Covering: up to 2018 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....

Postmenopausal women are increasingly using botanicals for menopausal symptom relief due to the increased breast cancer risk associated with traditional estrogen therapy. The deleterious effects of estrogens are associated with estrogen receptor (ER)α-dependent proliferation, while ERβ activation could enhance safety by opposing ERα effects. Three...

This perspective article explores the meaning of authenticity in the context of quality assessment of herbal/botanical materials and the challenges associated with discerning adulterations vs. contaminations vs. impurities. Authentic botanicals are by definition non-adulterated, a mutually exclusive relationship that is confirmed through the applic...

This report describes an approach using ¹H NMR iterative full-spin analysis (HiFSA) to extract definitive structural information on unknown peptides from 1D ¹H NMR data. By comparing the experimental data and HiFSA fingerprint of a known analogue, it is possible to isolate the characteristic ¹H subspectrum of the different amino acids and, thus, el...

Moringa oleifera Lam. is a tropical plant, used for centuries as food and traditional medicine. The aim of this study was to develop, validate and biochemically characterize an isothiocyanate-enriched moringa seed extract (MSE), and to compare the anti-inflammatory effects of MSE-containing moringa isothiocyanate-1 (MIC-1) with a curcuminoid-enrich...

Annotated 1H NMR spectrum of MIC-1. (DOCX)

1H NMR spectrum and quantitative analysis of CTE and CEM. (DOCX)

Structure of glucosinolates and the related metabolites. (DOCX)

Nutritional analysis of MSE. (DOCX)

Isothiocyanate-enriched moringa seed extract alleviates ulcerative colitis symptoms in mice. (PDF)

The potential of licorice dietary supplements to interact with drug metabolism was evaluated by testing extracts of three botanically identified licorice species (Glycyrrhiza glabra L., Glycyrrhiza uralensis Fish. ex DC. and Glycyrrhiza inflata Batalin) and 14 isolated licorice compounds for inhibition of 9 cytochrome P450 enzymes using a UHPLC-MS/...

In an effort to explore the residual complexity of naturally occurring chalcones from the roots of Glycyrrhiza inflata (Fabaceae), two new licochalcone A (LicA) derivatives were isolated as trace metabolites from enriched fractions. Both constituents contain a dihydrofuran moiety linked to carbons C-4 and C-5 of the retrochalcone core. Compound 1 (...

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 (1)H NMR (qHNMR), this study determined...

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 funda...

The concept of botanical integrity (BI), introduced previously in HerbalGram issue 106, involves the determination of identity, homogeneity, bioactivity, and safety of plant-derived materials designated for human consumption.1 It goes beyond previously established quality control principles. The inaugural article in this series described the three...

Botanical authenticity (i.e., “of undisputed origin”, “validity”) is best determined by a multi-layered approach that goes beyond botanical identity (i.e., “character”) by integrating phytochemical analyses and traceability documentation. Botanical or taxonomical identity has its roots in the anatomic description and genomic information of the plan...

In the field of food and nutrition, complex natural products (NPs) are typically obtained from cells/tissues of diverse organisms such as plants, mushrooms, and animals. Among them, edible fruits, grains, and vegetables represent most of the human diet. Because of an important dietary dependence, the comprehensive metabolomic analysis of dietary NP...

Page SI-9 of Supporting Information file jm500734a_si_001.pdf. The correct molecular weight of the target compound (MWt) is 290.27 g/mol, rather than 209.29 g/mol, and is reflected in the Supporting Information for this Addition and Correction.

Unlabelled: For the alleviation of menopausal symptoms, women frequently turn to botanical dietary supplements, such as licorice and hops. In addition to estrogenic properties, these botanicals could also have chemopreventive effects. We have previously shown that hops and its Michael acceptor xanthohumol (XH) induced the chemoprevention enzyme,...

Raw licorice roots represent heterogeneous materials obtained from mainly three Glycyrrhiza species. G. glabra, G. uralensis, and G. inflata exhibit marked metabolite differences in terms of flavanones (Fs), chalcones (Cs), and other phenolic constituents. The principal objective of this work was to develop complementary chemometric models for the...

Estrogen chemical carcinogenesis involves 4-hydroxylation of estrone/estradiol (E1/E2) by P450 1B1, generating catechol and quinone genotoxic metabolites that cause DNA mutations and initiate/promote breast cancer. Inflammation enhances this effect by up-regulating P450 1B1. The present study tested the three authenticated medicinal species of lico...

The present study explores Countercurrent Separation (CCS) as a powerful method to Deplete and Enrich Select Ingredients to Generate Normalized Extract Resources. A DESIGNER extract of European licorice (Glycyrrhiza glabra L.) depleted of glabridin (1) and four congeneric metabolites (2 – 5) was prepared for biological testing. Solvent system (SS)...

Licorice sold as Botanical Dietary Supplements (BDSs) can be obtained from mainly three Glycyrrhiza species: G. glabra, G. uralensis, and G. inflata.1 Therefore, BDSs are composed of either single Glycyrrhiza species, mixtures of Glycyrrhiza species, or even hybrids. A DNA barcoding method2 was optimized and applied for the authentication of 51 lic...

The risk of breast cancer increases with cumulative exposure to estrogens. Estrogens are metabolized to genotoxic metabolites by P450 1B1, which is up-regulated through inflammation and activation of the aryl hydrocarbon receptor (AhR). Accordingly, cytokine-induced P450 1B1 mRNA levels were inhibited by either a nuclear factor-kappaB (NF-κB) inhib...

The invention relates to novel eucomic acid (2-(4-hydroxybenzyl)malic acid) derivatives or plant extracts comprising such derivatives, and also to cosmetic or dermatological compositions containing these compounds or these extracts, and to cosmetic care methods using said compositions. Exemplary compounds are represented by formula (I) below: in w...

This report describes a fragment-based approach to the examination of congeneric organic compounds by NMR spectroscopy. The method combines the classic interpretation of 1D- and 2D-NMR data sets with contemporary computer-assisted NMR analysis. Characteristic NMR profiles of key structural motifs were generated by (1)H iterative full spin analysis...

Raw materials, ingredients, and products derived from plants are commonly referred to as herbs or botanicals in both the biomedical literature and the natural products health industry. This overarching term includes the breadth of crude herbs, plant parts, and the ingredients made from them, and also covers finished products such as botanical dieta...

This study introduces a flexible and compound targeted approach to Deplete and Enrich Select Ingredients to Generate Normalized Extract Resources, generating DESIGNER extracts, by means of chemical subtraction or augmentation of metabolites. Targeting metabolites based on their liquid-liquid partition coefficients (K values), K targeting uses count...

In any biomedical and chemical context, a truthful description of chemical constitution requires coverage of both structure and purity. This qualification affects all drug molecules, regardless of development stage (early discovery to approved drug) and source (natural product or synthetic). Purity assessment is particularly critical in discovery p...

Licorice botanicals are produced from the roots of Glycyrrhiza species (Fabaceae), encompassing metabolites of both plant and rhizobial origin. The composition in both primary and secondary metabolites (1°/2°Ms) reflects the physiologic state of the plant at harvest. Interestingly, the relative abundance of 1°Ms vs 2°Ms in licorice extracts remains...

Reported purification processes of glabridin (1) from the crude extract of European licorice (Glycyrrhiza glabra L.) generally involves a minimum of three liquid chromatography (LC) steps. Isolation methods using high speed counter current chromatography (HSCCC) have not been reported. The present study explores HSCCC as a powerful, targeted method...

Licorice (Glycyrrhizasp.), the root and underground stems of Glycyrrhiza species, has been used as a medicinal herb since ancient times, and approximately 18 species are distributed widely around the world. Due to the similarity between some of these species, distinguishing them based on microscopic and macroscopic examination is challenging. Here,...

The major bioactive markers characterizing the roots of licorice (Glycyrrhiza sp., Fabaceae) are secondary metabolites (2 °Ms) such as glycyrrhizin, a triterpene saponin, and glycosides of liquiritigenin (flavanone)/isoliquiritigenin (chalcone).¹ Consistent with our previous UHPLC-UV results,² and in agreement with the literature, these 2 °Ms accou...

Major phenolics from licorice roots (Glycyrrhiza sp.) are glycosides of the flavanone liquiritigenin (F) and its 2′-hydroxychalcone isomer, isoliquiritigenin (C). As the F and C contents fluctuate between batches of licorice, both quality control and standardisation of its preparations become complex tasks. To characterise the F and C metabolome in...

Nuclear Magnetic Resonance (NMR) is a universal and quantitative analytical technique. Being a unique structural tool, NMR also competes with metrological techniques for purity determination and reference material analysis. In pharmaceutical research, applications of quantitative NMR (qNMR) cover mostly the identification and quantification of drug...

The title compound {systematic name: 4-[(3R)-8,8-dimethyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol, commonly named glabridin}, C20H20O4, is a species-specific biomarker from the roots Glycyrrhiza glabra L. (European licorice, Fabaceae). In the present study, this prenylated isoflavan has been purified from an enriched CHCl3 fractio...

A fractionation methodology aimed at the metabolomic mining of new phytoconstituents for the widely used botanical, wild yam (Dioscorea villosa), makes use of 1D qHNMR and 2D NMR profiles along the preparative fractionation pathway. This quantifiable and structural guidance led to the isolation of 14 diarylheptanoids (1−14), including five new comp...

The increased cancer risk associated with hormone therapies has encouraged many women to seek non-hormonal alternatives including botanical supplements such as hops (Humulus lupulus) and licorice (Glycyrrhiza spec.) to manage menopausal symptoms. Previous studies have shown estrogenic properties for hops, likely due to the presence of 8-prenylnarig...

Licorice botanicals are produced from the roots of Glycyrrhiza species (Fabaceae), encompassing metabolites of both plant and rhizobial origin. The composition in both primary and secondary metabolites (1°/2°Ms) reflects the physiologic state of the plant at harvest. Interestingly, the relative abundance of 1°Ms vs 2°Ms in licorice extracts remains...

This study develops K-targeted metabolomic profiling as a new method for botanical standardization. The method combines selective enrichment of a metabolite, or a group of congeneric metabolites, from a complex extract by means of countercurrent separation (CCS), with exhaustive chemical characterization of the end-products, namely the isolated met...

The use of herbal medicines and dietary supplements (DS) in alleviating health symptoms has become popular worldwide, as reflected by the increased number of publications on the subject.1 In the United States in 2006, almost 50% of adults used dietary supplements with an uptrend percentage.² However, reports on apparently “identical” botanical mate...

This research investigated the bioactivity of different traditional remedies from the Lao PDR (Laos) to treat tuberculosis. In order to determine which plants have been in use over a long period of time, centuries-old medical documents were analyzed. Follow-up research involved field interviews with contemporary healers about plants that they are c...

Flavanones and their 2'-hydroxychalcones isomers are biosynthetically related and chemically interchangeable. This relationship is defined as a dynamic equilibrium, exemplifying the notion of residual complexity in natural compounds.1 We demonstrated recently that the interconversion between the flavanone liquiritigenin (LigF) and its chalcone isom...

Bioactive components in food plants can undergo dynamic processes that involve multiple chemical species. For example, 2'-hydroxychalcones can readily isomerize into flavanones. Although chemically well documented, this reaction has barely been explored in the context of cell-based assays. The present time-resolved study fills this gap by investiga...

A fractionation methodology aimed at the metabolomic mining of new phytoconstituents for the widely used botanical, wild yam (Dioscorea villosa), makes use of 1D qHNMR and 2D NMR profiles along the preparative fractionation pathway. This quantifiable and structural guidance led to the isolation of 14 diarylheptanoids (1-14), including five new comp...

Although well-studied from a chemical perspective, the real-time biological impact of the chalcone-flavanone isomerization, e.g., under cell-based bioassay conditions is not fully understood yet. Among the principal polyphenols of licorice roots (Glycyrrhiza sp. Fabaceae) are glycosides of the flavanone, liquiritigenin (LigF), and the chalcone, iso...

Glycyrrhiza glabra L. and G. uralensis Fisch. (Fabaceae) are the most widely used licorice species. Despite their chemical similarities, each species is defined by the presence of a broad range of secondary metabolites found in trace amounts. For our aim, which is directed toward their exhaustive metabolomic characterization, a 3-step fractionation...

Eucomic acid [(2R)-2-(p-hydroxybenzyl)malic acid)] (1) and three new glucopyranosyloxybenzyl eucomate derivatives, vandaterosides I (2), II (3), and III (4), were isolated and identified from the stems of Vanda teres. Their cellular antiaging properties were evaluated in a human immortalized keratinocyte cell line (HaCaT) by monitoring their effect...

The family of the orchids to date is poorly studied as a potential source of molecules with biological activity. The phytochemical analysis of extracts of Vanda coerulea stems (Orchidaceae), the isolation and the purification of the secondary metabolites realized by CLHP followed with high-resolution mass spectrometry and mono and two-dimensional n...

Concentration-dependent effect of stilbenoids (1-3) on PGE-2 release from irradiated (UVB 60 mJ/cm2) normal human epidermal keratinocytes (NHEK). Histogram represents the quantity of PGE-2 produced (PGE-2/ total NHEK proteins pg/µg) according to different treatments. Untreated irradiated (UVB+) and non irradiated (UVB-) NHEK were used as positive a...

In our investigations towards the isolation of potentially biologically active constituents from Orchidaceae, we carried out phytochemical and biological analyses of Vanda species. A preliminary biological screening revealed that Vanda coerulea (Griff. ex. Lindl) crude hydro-alcoholic stem extract displayed the best DPPH /(•)OH radical scavenging a...

Background: According to our previous results [1], imbricatin (1) and methoxycoleonin (2), the two major dihydrophenanthrenes isolated from V. coerulea Griff ex. Lindl (Orchidaceae) stems, displayed radical scavenging activities and inhibited PGE-2 release from UVB (60mJ/cm2) irradiated human normal epidermal keratinocytes (NHEK). It has been repor...

In the framework of our investigations towards the isolation of biologically active constituents from Orchidaceae, we carried out biological screening of various Orchids. Among the metabolites isolated from Vanda coerulea, three stilbenoids corresponding to imbricatin, methoxycoelonin and gigantol, display protective antioxidant and anti-inflammato...