DOCSLIB.ORG

Download Presentation (PDF)

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Download Presentation (PDF) Characterization of the Oxygen Heterocyclic Compounds (Coumarins, Psoralens, and Polymethoxylated Flavones) in Food Products Mariosimone Zoccali1, Adriana Arigò1, Marina Russo2, Francesca Rigano3, Paola Dugo1,2,3 and Luigi Mondello1,2,3 1Dipartimento di Scienze Chimiche, Biologiche, Farmaceutiche ed Ambientali, University of Messina, Italy 2University Campus Bio-Medico of Rome, Italy 3Chromaleont s.r.l. University of Messina, Italy Italy Universityof Messina, [email protected] Focus on the Oxygenated Heterocyclic Compounds secondary metabolites commonly found in all citrus plants Furocoumarin or Coumarin psoralen Polymethoxyflavone Beneficial effect on humans: Harmful effect on humans: ➢Anticancer ➢Phototoxic ➢Antioxidant ➢Inhibitor of intestinal and liver drug Italy Universityof Messina, ➢Antibacterial metabolism ➢Anti-inflammatory Development of high sensitive analytical methods Isolation of pure compounds Citrus essential oils Citrus bergamia Risso Food industry Cosmetic industry University of Messina, Italy Universityof Messina, Flavour and fragrance industry Opinion on Coumarin in Food products The Panel considered the toxicity studies and the studies on the metabolism of coumarin in humans with CYP2A6 polymorphism that have become available since the last opinion of 2004, as well as clinical studies, and concluded to maintain the TDI of 0.1 mg coumarin/kg bw allocated in the 2004 opinion. University of Messina, Italy Universityof Messina, Furocoumarins in Food products Furocoumarins are a class of photoactive compounds found in several plant species and may be responsible for the observed association between consumption of citrus products and the risk of skin cancer. When irradiated with UV light, furocoumarins can undergo photoactivation, putting them into an excited and highly reactive triplet state. In this state, certain Italy Universityof Messina, furocoumarins can form adducts with DNA, induce protein denaturation, form cycloadducts with saturated fatty acids, and react with ground state oxygen to form reactive oxygen species that can cause cellular damage Analytical techniques employed for the characterization of the oxygenated heterocyclic compounds Chromatography Detection/identification TLC NP-LC Fluorescence RP-LC EI-MS LC×LC APCI-MS Micro-LC PDA/UV Nano-LC LRI SFC Comprehensive two dimensional separation of oxygen LC) University of Messina, Italy Universityof Messina, - 5 heterocyclic components of lemon oil 2 81APCI- (P. Dugo, M. Ramírez Fernández, A. Cotroneo, G. 4 MS 6 Dugo, L. Mondello. J. Chromatogr. Sci. 44, (2006) 561) PDA/U 3 7 V 7 9 1 RF 11 Reversed phase (RP Reversedphase 9 10 The elution order in both dimensions represents a 6 EI-MS key information for the identification of unknown 10 11 in the 2D plot Normal phase (NP-LC) Identification strategies 1 The UV spectrum easily allows identifying the chemical class (coumarin, furocoumarin or polymethoxyflavones), as well as the position of substituents in the heterocyclic structure 2 The interpretation of MS spectra can lead to a more reliable identification 3 Both UV and MS spectra can be included in UV and MS libraries to make the identification process automatic and faster 4 Retention time information can be used complementarily to spectral data University of Messina, Italy Universityof Messina, UV library IUPAC NAME CAS University of Messina, Italy Universityof Messina, UV library: automatic identification University of Messina, Italy Universityof Messina, Both UV and retention time are necessary to confirm the identification. MS library University of Messina, Italy Universityof Messina, Usually, only the molecular weight information is provided (impossibility to identify isomers) Interferences from the matrix or a matrix effect can significantly reduce the spectral similarity (low identification reliability) mAU 200 195 196 195 201 202 200 221 222 222 The use The use of alibrary MS help the identification of species characterized by 250 254 254 254 268 269 270 300 287 288 289 313 314 314 350 nm Byakangelicol Phellopterin Byakangelicin identical UV spectrum MS library University of Messina, Italy Remarks/Evaluations In the case of molecules characterized by the same molecular weight, more powerful MS instrumentation (high resolution, tandem MS systems) would be necessary for structure elucidation. One of the main purpose of the present research is the finding of less expensive and easier solution to improve identification reliability of LC methods University of Messina, Italy Universityof Messina, Linear retention index (LRI) approach More recent approaches Identification tools in chromatography Retention behaviour Spectral information LC GC GC LC No universal Stable LRI system EI-MS spectra API-MS and/or LRI system by Van Den Dool UV spectra and Kratz* University of Messina, Italy Universityof Messina, HIGHLY RELIABLE IDENTIFICATION POOR IDENTIFICATION POWER *Van Den Dool and Kratz , J. Chrom. A, 11 (1963) 436-471 Use of LRI as additional filter • In gas chromatography LRI represents a system in which the retention times of analytes are correlated to a reference standard mixture, making retention data dependent only on the three terms interaction analyte-stationary phase-mobile phase and indipendent from other chromatographic conditions (column dimension, temperature program, mobile phase linear velocity) • LRI are normally employed as an extra criterion of mass spectral library searching: compounds with a high spectra matching but with a LRI value falling out from a selected range are automatically excluded from the list of possible candidates • In liquid chromatography retention data are strongly dependent from the mobile Italy Universityof Messina, phase composition, thus increasing the number of parameters to be considered. • The building of an LRI database would be more meaningful in the LC-MS system where retention data might be complementary to the identification capability of MS, as in GC-MS. LRI in LC A consistent literature refers about the employment of retention index during the decades ’80s-90s, sometimes combined with UV spectral information for identification purposes. An example Bogusz and Wu, J. Anal. Toxicol. 1991, 15, 188-197. The influence of several experimental conditions, such as the stationary phase chemistry or mobile phase composition, was evaluated, allowing to conclude that a standardization of the LC conditions is necessary to create a usable database. Bogusz et al. Italy Universityof Messina, «The elution conditions should be carefully standardized in order to obtain reproducible results» J. Liq. Chromatogr. R.T. 1996, 19, 1291-1316. In the last decades, the higher batch-to-batch reproducibility in LC columns and instrumentation can lead to a more reliable and stable LRI system, also at interlaboratory levels. Reference standard mixture “many attempts” 1-nitroalkanes Three homologue series have been reported in literature: alkan-2-ones from C3 to C23 (low UV absorption) Analytes alkyl aryl ketones from acetophenone to heptanophenone (long elution times) 1-nitroalkanes from nitromethane to 1-nitrooctane (low availibility) Alkyl aryl ketones Italy Universityof Messina, LRI calculation Bogusz et al. J. Anal. Toxicol. 1988, 12, 325-329 LC-MS/MS approach as a novel unified tool for the quali-quantitative characterization of oxygen heterocyclic compounds Comparison with the recent LC-PDA method University of Messina, Italy Universityof Messina, Project schedule (work-flow) Nexera-i Nexera X2 UHPLC LCMS-8060 ▪ Validation of the LC-PDA ▪ Validation of the LC-MS/MS method (LoD, LoQ, repeatability, accuracy, method (LoD, LoQ, repeatability, accuracy, linearity) linearity) ▪ Creation of an UV-library ▪ Optimization of MRM transition parameters for each target compouds ▪ Calculation of the LRI of each target compounds ▪ Creation of MS and MS/MS-libraries ▪ Identification of oxygenated ▪ Calculation of the LRI of each target heterocyclic compounds through compounds both UV library and LRI ▪ Identification of oxygenated ▪ Quantitative determination of targets heterocyclic compounds through Italy Universityof Messina, compounds in the real samples by means of both MS and MS/MS libraries and LRI calibration curves. ▪ Realization of calibration curves for each STD compounds ▪ Quantitative determination of targets compounds in the real samples by means of calibration curves Analysis conditions Column: Ascentis Express C18 (50 × 4.6 mm, 2.7 mm) Solvent A: Water/Methanol/THF 85:10:5 v/v) Solvent B: Methanol/THF 95:5 v/v) Gradient: Flow rate: 2 mL/min Oven Temperature: 40° C PDA parameters Time constant: 0.48 sec Sampling: 4.1667 Hz Range: 190-370 MS parameters Interface: APCI positive MRM mode University of Messina, Italy Universityof Messina, Nebulizing Gas Flow: 3 L/min Interface Temperature: 450° C DL Temperature: 300° C Heat Block Temperature: 300° C Drying Gas Flow: 15 L/min CID GAS: 270 kPa LC-PDA experimental work-flow Inject the sample solution Inject the reference homologue series for LRI calculation Identify the sample components by OHCs library using UV and LRI filters University of Messina, Italy Universityof Messina, Quantify the sample by external calibration UHPLC-PDA (iseries) instrumentation used in this study PDA chromatogram of all the target analytes mAU 315nm 10 20 3 24+25 12 26+27 22 23 15 2 11 28 29 33 35 1 5 20 34 8 9 13+14 31 10 6 15 21 4 7 16 18 32 5 17 19 30 0 University of Messina, Italy Universityof Messina, 0.0 1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0 9.0 10.0 11.0 min Mix of all STDs (35 compounds among
Load more

Recommended publications
  • Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity
    toxins Article Suspect and Target Screening of Natural Toxins in the Ter River Catchment Area in NE Spain and Prioritisation by Their Toxicity Massimo Picardo 1 , Oscar Núñez 2,3 and Marinella Farré 1,* 1 Department of Environmental Chemistry, IDAEA-CSIC, 08034 Barcelona, Spain; [email protected] 2 Department of Chemical Engineering and Analytical Chemistry, University of Barcelona, 08034 Barcelona, Spain; [email protected] 3 Serra Húnter Professor, Generalitat de Catalunya, 08034 Barcelona, Spain * Correspondence: [email protected] Received: 5 October 2020; Accepted: 26 November 2020; Published: 28 November 2020 Abstract: This study presents the application of a suspect screening approach to screen a wide range of natural toxins, including mycotoxins, bacterial toxins, and plant toxins, in surface waters. The method is based on a generic solid-phase extraction procedure, using three sorbent phases in two cartridges that are connected in series, hence covering a wide range of polarities, followed by liquid chromatography coupled to high-resolution mass spectrometry. The acquisition was performed in the full-scan and data-dependent modes while working under positive and negative ionisation conditions. This method was applied in order to assess the natural toxins in the Ter River water reservoirs, which are used to produce drinking water for Barcelona city (Spain). The study was carried out during a period of seven months, covering the expected prior, during, and post-peak blooming periods of the natural toxins. Fifty-three (53) compounds were tentatively identified, and nine of these were confirmed and quantified. Phytotoxins were identified as the most frequent group of natural toxins in the water, particularly the alkaloids group.
    [Show full text]
  • The Health Benefits of Grapefruit Furanocoumarins1 Yu Wang and Laura Reuss2
    FSHN18-8 The Health Benefits of Grapefruit Furanocoumarins1 Yu Wang and Laura Reuss2 Although not recommended for use with certain medica- tions, grapefruits are known for their numerous health benefits. Both these effects come from, in part, natural chemicals called furanocoumarins. Although these biologically active plant compounds, or phytochemicals, are beneficial to overall health, some compounds have been shown to interact with numerous medications, causing adverse effects known as the “grapefruit juice effect.” Furanocoumarins and flavanones are the major compounds responsible in these drug interactions. Several studies have reported that furanocoumarins present in grapefruit affect absorption of some medications by interfering with a cer- tain liver and intestinal enzyme (Guo et al. 2000). However, numerous studies have shown that compounds in citrus fruits, including furanocoumarins, reduce inflammation and stop cancer cells from multiplying. Furthermore, they Figure 1. Furanocoumarins in grapefruit originate from psoralen and include bergaptol, bergapten, bergamottin, and epoxybergamottin. may also help repair damaged DNA that would otherwise Red, Ruby Red, Ray Red, Star Ruby, Thompson Pink, Marsh contribute to the development of tumors. A variety of White, and Duncan (Girennavar et al. 2008). furanocoumarins can be found in all types of citrus, but those found in grapefruit possess several health-promoting Grapefruits have long been considered a part of a healthy properties that include anti-inflammatory, anti-cancer, diet due to being rich in vitamins, minerals, fiber, and anti-obesity, and bone-building effects (Madrigal-Bujaidar phytochemicals, such as flavonoid and furanocoumarins. It et al. 2013; Mahgoub 2002; Chudnovskiy et al. 2014). is these phytochemicals, in particular the furanocoumarins, that demonstrate anti-inflammatory, anti-cancer, and The furanocoumarins found in grapefruit all originate anti-oxidative effects (Lee et al.
    [Show full text]
  • Phytochemicals
    Phytochemicals HO O OH CH OC(CH3)3 3 CH3 CH3 H H O NH O CH3 O O O O OH O CH3 CH3 OH CH3 N N O O O N N CH3 OH HO OH HO Alkaloids Steroids Terpenoids Phenylpropanoids Polyphenols Others Phytochemicals Phytochemical is a general term for natural botanical chemicals Asiatic Acid [A2475] is a pentacyclic triterpene extracted from found in, for example, fruits and vegetables. Phytochemicals are Centella asiatica which is a tropical medicinal plant. Asiatic Acid not necessary for human metabolism, in contrast to proteins, possess wide pharmacological activities. sugars and other essential nutrients, but it is believed that CH3 phytochemicals affect human health. Phytochemicals are CH3 components of herbs and crude drugs used since antiquity by humans, and significant research into phytochemicals continues today. H C CH H C OH HO 3 3 O Atropine [A0754], a tropane alkaloid, was first extracted from H CH3 the root of belladonna (Atropa belladonna) in 1830s. Atropine is a HO competitive antagonist of muscarine-like actions of acetylcholine CH3 H and is therefore classified as an antimuscarinic agent. OH [A2475] O NCH3 O C CHCH2OH Curcumin [C0434] [C2302], a dietary constituent of turmeric, has chemopreventive and chemotherapeutic potentials against various types of cancers. OO CH3O OCH3 [A0754] HO OH Galantamine Hydrobromide [G0293] is a tertiary alkaloid [C0434] [C2302] found in the bulbs of Galanthus woronowi. Galantamine has shown potential for the treatment of Alzheimer's disease. TCI provides many phytochemicals such as alkaloids, steroids, terpenoids, phenylpropanoids, polyphenols and etc. OH References O . HBr Phytochemistry of Medicinal Plants, ed.
    [Show full text]
  • Bergamot Oil: Botany, Production, Pharmacology
    Entry Bergamot Oil: Botany, Production, Pharmacology Marco Valussi 1,* , Davide Donelli 2 , Fabio Firenzuoli 3 and Michele Antonelli 2 1 Herbal and Traditional Medicine Practitioners Association (EHTPA), Norwich NR3 1HG, UK 2 AUSL-IRCCS Reggio Emilia, 42122 Reggio Emilia RE, Italy; [email protected] (D.D.); [email protected] (M.A.) 3 CERFIT, Careggi University Hospital, 50139 Firenze FI, Italy; fabio.firenzuoli@unifi.it * Correspondence: [email protected] Definition: Bergamot essential oil (BEO) is the result of the mechanical manipulation (cold pressing) of the exocarp (flavedo) of the hesperidium of Citrus limon (L.) Osbeck Bergamot Group (synonym Citrus × bergamia Risso & Poit.), resulting in the bursting of the oil cavities embedded in the flavedo and the release of their contents. It is chemically dominated by monoterpene hydrocarbons (i.e., limonene), but with significant percentages of oxygenated monoterpenes (i.e., linalyl acetate) and of non-volatile oxygen heterocyclic compounds (i.e., bergapten). Keywords: bergamot; citrus; essential oil; production; review 1. Introduction The taxonomy, and consequently the nomenclature, of the genus Citrus, is particularly complicated and has been rapidly changing in recent years (see Table1). For over 400 years, the centre of origin and biodiversity, along with the evolution and phylogeny of the Citrus species, have all been puzzling problems for botanists and the confusing and changing Citation: Valussi, M.; Donelli, D.; nomenclature of this taxon over the years can reflect intrinsic reproductive features of Firenzuoli, F.; Antonelli, M. Bergamot Oil: Botany, Production, the species included in this genus, the cultural and geographical issues, and the rapidly Pharmacology. Encyclopedia 2021, 1, evolving techniques used to clarify its phylogeny [1].
    [Show full text]
  • Identification and Functional Characterization of the First Two
    Identification and functional characterization of the first two aromatic prenyltransferases implicated in the biosynthesis of furanocoumarins and prenylated coumarins in two plant families: Rutaceae and Apiaceae Fazeelat Karamat To cite this version: Fazeelat Karamat. Identification and functional characterization of the first two aromatic prenyl- transferases implicated in the biosynthesis of furanocoumarins and prenylated coumarins in two plant families: Rutaceae and Apiaceae. Agronomy. Université de Lorraine, 2013. English. NNT : 2013LORR0029. tel-01749560 HAL Id: tel-01749560 https://hal.univ-lorraine.fr/tel-01749560 Submitted on 29 Mar 2018 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. AVERTISSEMENT Ce document est le fruit d'un long travail approuvé par le jury de soutenance et mis à disposition de l'ensemble de la communauté universitaire élargie. Il est soumis à la propriété intellectuelle de l'auteur. Ceci implique une obligation de citation et de référencement lors de l’utilisation de ce document. D'autre part, toute contrefaçon, plagiat,
    [Show full text]
  • Natural Compounds, Fraxin and Chemicals Structurally Related to Fraxin Protect Cells from Oxidative Stress
    EXPERIMENTAL and MOLECULAR MEDICINE, Vol. 37, No. 5, 436-446, October 2005 Natural compounds, fraxin and chemicals structurally related to fraxin protect cells from oxidative stress Wan Kyunn Whang1, Hyung Soon Park2, genes expressed differentially by fraxin and to InHye Ham1, Mihyun Oh1, compare antioxidative effect of fraxin with its struc- Hong Namkoong3, Hyun Kee Kim3, turally related chemicals. Of the coumarins, protective 2 4 effects of fraxin against cytotoxicity induced by H2O2 Dong Whi Hwang , Soo Young Hur , were examined in human umbilical vein endothelial 4 5 Tae Eung Kim , Yong Gyu Park , cells (HUVECs). Fraxin showed free radical scavenging Jae-Ryong Kim6 and Jin Woo Kim3,4,7 effect at high concentration (0.5 mM) and cell protective effect against H2O2-mediated oxidative stress. Fraxin 1 College of Pharmacy, Chung-Ang University recovered viability of HUVECs damaged by H2O2- 221, Heukseok-dong, Dongjak-gu treatment and reduced the lipid peroxidation and the Seoul 156-861, Korea internal reactive oxygen species level elevated by H2O2 2KeyGene Life Science Institute treatment. Differential display reverse transcrip- KeyGene Science, Corp. tion-PCR revealed that fraxin upregulated antiapo- Ansan, Gyeonggido 425-791, Korea ptotic genes (clusterin and apoptosis inhibitor 5) and 3Molecular Genetic Laboratory tumor suppressor gene (ST13). Based on structural Research Institute of Medical Science similarity comparing with fraxin, seven chemicals, 4Department of Obstetrics and Gynecology fraxidin methyl ether (29.4% enhancement of viability), 5Department of Biostatistics prenyletin (26.4%), methoxsalen (20.8 %), diffratic acid College of Medicine (19.9%), rutoside (19.1%), xanthyletin (18.4%), and The Catholic University of Korea kuhlmannin (18.2%), enhanced more potent cell via- Seoul 137-040, Korea bility in the order in comparison with fraxin, which 6Department of Biochemistry and Molecular Biology showed only 9.3% enhancement of cell viability.
    [Show full text]
  • Distribution of Furanocoumarins in Grapefruit Juice Fractions
    5158 J. Agric. Food Chem. 2005, 53, 5158−5163 Distribution of Furanocoumarins in Grapefruit Juice Fractions JOHN A. MANTHEY* AND BEÄ LA S. BUSLIG Citrus and Subtropical Products Laboratory, Agricultural Research Service, U.S. Department of Agriculture, 600 Avenue S N.W., Winter Haven, Florida 33881 The reported effects of grapefruit (Citrus paradisi Macf.) juice on oral bioavailability of certain prescription drugs have led to the discovery of the inhibition by compounds in grapefruit of cytochrome P450 3A4 (CYP3A4) in the intestinal wall and liver. Recent evidence indicates that furanocoumarins related to bergamottin [5-[(3′,7′-dimethyl-2′,6′-octadienyl)oxy]psoralen] are primarily responsible for the grapefruit effect, yet the exact mechanisms and roles that specific compounds play in this effect are still uncertain. In the current experiments freshly extracted grapefruit juice was separated into four fractions, consisting of raw finished juice (∼5% fine pulp), centrifugal retentate (∼35% fine pulp), centrifuged supernatant (<1% pulp), and coarse finisher pulp. The relative concentrations of furanocoumarins in each of these grapefruit juice fractions were measured by HPLC-MS. These measurements showed that the centrifugal retentate had the highest furanocoumarin content, containing 892 ppm of bergamottin, 628 ppm of 6′,7′-dihydroxybergamottin, 116 ppm of 6′,7′- epoxybergamottin, 105 ppm of 7-geranyloxycoumarin, and ∼467 ppm of furanocoumarin dimers. These high furanocoumarin concentrations make this fraction a useful starting material for preparative- scale isolations of these compounds. MS analysis of this furanocoumarin-enriched fraction provided evidence of additional furanocoumarins in grapefruit juice that remain to be fully characterized and evaluated for their roles in the grapefruit-drug interactions.
    [Show full text]
  • The Fascinating History of Bergamot (Citrus Bergamia Risso & Poiteau
    Journal of Environmental Science and Engineering A 6 (2017) 22-30 doi:10.17265/2162-5298/2017.01.003 D DAVID PUBLISHING The Fascinating History of Bergamot (Citrus Bergamia Risso & Poiteau), the Exclusive Essence of Calabria: A Review Gina Maruca1, Gaetano Laghetti1, Rocco Mafrica2, Domenico Turiano3 and Karl Hammer4 1. Institute of Bioscience and Bioresouces, National Council of Research, Bari 70126, Italy 2. Institute of Agronomy, Department of Agrarian, Mediterranean University of Reggio Calabria, Reggio Calabria 89122, Italy 3. Sperimental Demonstrative Centre of the Straits of Messina, Regional Administration for the Development of the Calabrian Agriculture, Reggio Calabria 89100, Italy 4. Former Agrobiodiversity, University of Kassel, Witzenhausen D-37213, Germany Abstract: The bergamot (Citrus bergamia Risso et Poiteau), a citrus fruit growing almost exclusively in the South Italy, is considered the “prince of citrus” for its storical role in the perfume industry due to its essential oil, a product in great demand of a pleasant and refreshing scent. Recently, analgesic, anxiolytic, neuroprotective consistent effects have been ascribed to bergamot essential oil when it is used in aromatherapy, for the relief of pain and symptoms associated with stress-induced anxiety and depression. Moreover, today, bergamot fruit due to a considerable abundance and variety of nutraceutical compounds which are present in its juice, is becoming increasingly important also in the food, pharmaceutical and confectionery industries. In this review, it is discussed that the literature on C. bergamia, focusing on the several studies performed with the experimental data, and recently accumulated, may form the rational basis for further development. Key words: Bergamot (Citrus bergamia Risso & Poiteau), essential oil.
    [Show full text]
  • Download/Index.Php), and Onekp (
    bioRxiv preprint doi: https://doi.org/10.1101/2020.07.07.192757; this version posted July 8, 2020. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. 1 2 Parallel evolution of UbiA superfamily proteins into aromatic O- 3 prenyltransferases in plants 4 5 Authors 6 Ryosuke Munakata1,2, Alexandre Olry2, Tomoya Takemura1, Kanade Tatsumi1, Takuji Ichino1, Cloé 7 Villard2, Joji Kageyama1, Tetsuya Kurata3, Masaru Nakayasu1, Florence Jacob4, Takao Koeduka5 8 Hirobumi Yamamoto6, Eiko Moriyoshi1, Tetsuya Matsukawa7,8, Jeremy Grosjean2, Célia Krieger2 1 9 10 2* 1* 9 Akifumi Sugiyama , Masaharu Mizutani , Frédéric Bourgaud , Alain Hehn , and Kazufumi Yazaki 10 11 *Author for correspondence 12 Kazufumi Yazaki 13 Tel: +81 774 38 3621 14 Email: [email protected] 15 16 Alain Hehn 17 Tel: +33 3 72 74 40 77 18 Email: [email protected] 19 20 Affiliation 21 1 Laboratory of Plant Gene Expression, Research Institute for Sustainable Humanosphere, Kyoto 22 University, Uji, Kyoto, 611–0011, Japan 23 2 Université de Lorraine, INRA, LAE, F54000, Nancy, France 24 3 EditForce Inc., Fukuoka 810-0001, Japan bioRxiv preprint doi: https://doi.org/10.1101/2020.07.07.192757; this version posted July 8, 2020. The copyright holder for this preprint (which was not certified by peer review) is the author/funder. All rights reserved. No reuse allowed without permission. 25 4 PalmElit SAS, Montferrier sur Lez 34980, France 26 5 Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi 27 753-8515, Japan 28 6 Department of Applied Biosciences, Faculty of Life Sciences, Toyo University, Izumino 1–1-1, 29 Itakura-machi, Ora-gun, Gunma 374-0193, Japan 30 7 The Experimental Farm, Kindai University, Wakayama, Japan 31 8 Faculty of Biology-Oriented Science and Technology, Kindai University, 32 Wakayama, Japan 33 9 Functional Phytochemistry, Graduate School of Agricultural Science, Kobe University, Kobe, 34 Japan.
    [Show full text]
  • White and Colored Grapefruit Juice Produce Similar Pharmacokinetic Interactions
    ORIGINAL ARTICLES Clinical Pharmaceutics Laboratory, Department of Pharmaceutics, Meiji Pharmaceutical University, Tokyo, Japan White and colored grapefruit juice produce similar pharmacokinetic interactions Y. Uesawa, M. Abe, K. Mohri Received March 4, 2008, accepted March 28, 2008 Dr. Yoshihiro Uesawa, Clinical Pharmaceutics Laboratory, Department of Pharmaceutics, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan [email protected] Pharmazie 63: 598–600 (2008) doi: 10.1691/ph.2008.8550 Colored (pink and red) grapefruit pulp contains lower amounts of the furanocoumarin derivatives that cause pharmacokinetic interactions than white grapefruit pulp. However, few studies have ex- amined interactions with colored juice products. Therefore, we examined the potential interactions of both white and colored grapefruit products by measuring the concentrations of furanocoumarin derivatives and inhibition of the metabolizing cytochrome P450 (CYP) 3A enzymes, the target of the furanocoumarins. We measured concentrations of three major furanocoumarin derivatives, ber- gaptol, bergamottin, and 60,70-dihydroxybergamottin, with high-performance liquid chromatography in 21 brands of grapefruit juice sold in Japan, including 14 white and 7 colored brands. The mean difference in bergaptol, bergamottin, and 60,70-dihydroxybergamottin concentrations in white grape- fruit juice samples was 1.59, 0.902, and 1.03 times, respectively, the amounts in colored samples. White samples inhibited CYP3A-mediated testosterone-6b oxidation in human liver microsomes by 1.04 and 0.922 times (whole juice and furanocoumarin, respectively) the inhibition by colored juice. Thus, colored grapefruit juice may produce drug interactions at the same rate as white grapefruit juice. 1. Introduction 2. Investigations, results and discussion 2.1.
    [Show full text]
  • Esculetin) - an Antirheumatoid Arthritic Compound: an Update
    Online - 2455-3891 Vol 11, Special issue 4, 2018 Print - 0974-2441 Research Article COUMARIN (ESCULETIN) - AN ANTIRHEUMATOID ARTHRITIC COMPOUND: AN UPDATE JAYA KUMARI S*, ANANDHI N, MOUNISHA B, MOHAMED SAMEER MH Department of Pharmacognosy, School of Pharmaceutical Sciences, Vels Institute of Science Technology and Advanced Studies, Pallavaram, Chennai, Tamil Nadu, India. Email: [email protected] Received: 11 October 2018, Revised and Accepted: 15 December 2018 ABSTRACT Context: Esculetin is a natural polyphenolic compound. It is chemically 6,7-dihydroxycoumarin and one of the ingredients of Cortex fraxini, a Chinese traditional medicine. It is used as a dietary supplement and found as non-toxic. Recently, there are many research works evaluated on esculetin in arthritis with supported molecular mechanisms. Objectives: Esculetin becoming more attractive prodrug for arthritis. Hence, the present minireview will consolidate the targeted site of esculetin in the treatment of arthritis over the past decade. Results: The most important molecular mechanism of esculetin is an antioxidant activities with decreased level of reactive oxygen species/reactive nitrogen species. It also inhibited lipoxygenase 5, lipoxygenase 12, and tyrosinase enzymes. It reduces the inflammation by modulating the key inflammatory enzyme matrix metalloproteinase-1 activity. It also lowers the nitrous oxide and prostaglandin E2 level in synovial fluid. Esculetin derivatives such as 5-methoxy esculetin inhibited the activity of nitrogen-activated protein kinases. The updated data also reveal that esculetin suppresses the leukotriene B4 level in plasma of adjuvant-induced arthritis tested animals. Conclusion: The presented update showed that esculetin may be useful as a tool in regulating the mechanism and physiological functions of the inflammatory mediators and enzyme.
    [Show full text]
  • The Nonvolatile and Volatile Metabolites of Prangos Ferulacea and Their Biological Properties*
    Published online: 2019-03-20 Reviews The Nonvolatile and Volatile Metabolites of Prangos ferulacea and Their Biological Properties* Authors Maurizio Bruno 1, Vincenzo Ilardi2, Giulio Lupidi 2, Luana Quassinti 3, Massimo Bramucci 3, Dennis Fiorini 4, Alessandro Venditti5,FilippoMaggi3 Affiliations Correspondence 1 Department of Biological, Chemical and Pharmaceutical Prof. Maurizio Bruno Sciences and Technologies (STEBICEF), University of Department of Biological, Chemical and Pharmaceutical ʼ Palermo, Viale delle Scienze, Parco d Orleans II, Palermo, Sciences and Technologies (STEBICEF), University of Palermo Italy Viale delle Scienze Ed. 17, Parco dʼOrleans II, 90128 Palermo, 2 Department of Earth and Marine Sciences (DISTeM), Italy University of Palermo, Palermo, Italy Phone:+3909123897531 3 School of Pharmacy, University of Camerino, Camerino, [email protected] Italy 4 School of Science and Technologies, University of ABSTRACT Camerino, Camerino, Italy Prangos ferulacea (L.) Lindl. (Fam. Apiaceae), an orophilous 5 DepartmentofChemistry,UniversityofRome species of eastern Mediterranean and western Asia, possesses “La Sapienza”, Rome, Italy a number of biological properties that are worthy of exploita- tion in different fields. Phytochemical investigations revealed Key words the presence of coumarins, prenyl-coumarins, and furano- Prangos ferulacea, Apiaceae, coumarins, prenyl‑coumarins, coumarins as the main constituents of this species, as well as furano‑coumarins, essential oil several flavonoids. Among prenyl-coumarins, osthol is a promising apoptotic agent quite selective toward cancer cells. received December 18, 2018 In addition, the essential oils have been extensively investi- revised March 1, 2019 gated, and several chemotypes have been identified. This accepted March 5, 2019 work reviews the literature on this species published between Bibliography 1965 and 2018, describes its volatile and nonvolatile metabo- DOI https://doi.org/10.1055/a-0873-8622 lites, and outlines its pharmacological effects.
    [Show full text]