DOCSLIB.ORG

(+)-Lariciresinol to Control Bacterial Growth of Staphylococcus Aureus and Escherichia Coli O157:H7

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
(+)-Lariciresinol to Control Bacterial Growth of Staphylococcus Aureus and Escherichia Coli O157:H7 fmicb-08-00804 April 29, 2017 Time: 14:57 # 1 ORIGINAL RESEARCH published: 03 May 2017 doi: 10.3389/fmicb.2017.00804 Efficacy of (C)-Lariciresinol to Control Bacterial Growth of Staphylococcus aureus and Escherichia coli O157:H7 Vivek K. Bajpai1†, Shruti Shukla2†, Woon K. Paek3, Jeongheui Lim3*, Pradeep Kumar4*, Pankaj Kumar5 and MinKyun Na6* 1 Department of Applied Microbiology and Biotechnology, Microbiome Laboratory, Yeungnam University, Gyeongsan, South Korea, 2 Department of Energy and Materials Engineering, Dongguk University, Seoul, Seoul, South Korea, 3 National Edited by: Science Museum, Ministry of Science, ICT and Future Planning, Daejeon, South Korea, 4 Department of Forestry, North Luis Cláudio Nascimento da Silva, Eastern Regional Institute of Science and Technology, Nirjuli, India, 5 Department of Microbiology, Dolphin (PG) College of CEUMA University, Brazil Science & Agriculture, Fatehgarh Sahib, India, 6 College of Pharmacy, Chungnam National University, Daejeon, South Korea Reviewed by: Diego Garcia-Gonzalo, This study was undertaken to assess the antibacterial potential of a polyphenolic University of Zaragoza, Spain Dinesh Yadav, compound (C)-lariciresinol isolated from Rubia philippinensis against selected Deen Dayal Upadhyay Gorakhpur foodborne pathogens Staphylococcus aureus KCTC1621 and Escherichia coli University, India C Osmar Nascimento Silva, O157:H7. ( )-Lariciresinol at the tested concentrations (250 mg/disk) evoked a Universidade Católica Dom Bosco, significant antibacterial effect as a diameter of inhibition zones (12.1–14.9 mm) with Brazil minimum inhibitory concentration (MIC), and minimum bactericidal concentration values *Correspondence: of 125–250 and 125–250 mg/mL, respectively. Furthermore, (C)-lariciresinol at MIC Pradeep Kumar C [email protected] showed reduction in bacterial cell viabilities, efflux of potassium (K ) ions and release Jeongheui Lim of 260 nm materials against E. coli O157:H7 and S. aureus KCTC1621. Moreover, [email protected] MinKyun Na deteriorated cell wall morphology of E. coli O157:H7 and S. aureus KCTC1621 cells [email protected] treated with (C)-lariciresinol at MIC further confirmed its inhibitory effect against the †These authors have contributed tested pathogens, suggesting it to be an alternative means of antimicrobials. equally to this work. Keywords: antimicrobial effect, Rubia philippinensis,(C)-lariciresinol, foodborne pathogens, scanning electron Specialty section: microscopy This article was submitted to Antimicrobials, Resistance and Chemotherapy, INTRODUCTION a section of the journal Frontiers in Microbiology Food industry and regulatory authorities are more concerned about the safety of food, and its Received: 14 January 2017 contamination by foodborne pathogenic bacteria (Al-zorekya and Al–Taher, 2015). Consumer Accepted: 19 April 2017 awareness on the knowledge of quality food information has raised greater concern to use Published: 03 May 2017 high quality food products due to possible contamination by foodborne pathogenic bacteria. Citation: Among foodborne pathogens, Staphylococcus aureus and Escherichia coli O157:H7 have posed Bajpai VK, Shukla S, Paek WK, serious concerns to consumers due to their reported foodborne outbreaks and foodborne illnesses Lim J, Kumar P, Kumar P and Na M (Awaisheh et al., 2013). In the USA, about 75 and 68% cases account for foodborne outbreaks (2017) Efficacy of (C)-Lariciresinol and reported cases of foodborne illnesses, respectively (Scot, 2003). Meat associated foodborne to Control Bacterial Growth illnesses in Canada costs about five hundred million dollars for their cure (Oussalah et al., of Staphylococcus aureus and Escherichia coli O157:H7. 2007). Furthermore, failure to control foodborne pathogens using current preservation techniques Front. Microbiol. 8:804. has raised a serious concern to explore new and natural classes of antimicrobials to combat doi: 10.3389/fmicb.2017.00804 against serious foodborne pathogens (Awaisheh and Ibrahim, 2009). Recently, it has been Frontiers in Microbiology| www.frontiersin.org 1 May 2017| Volume 8| Article 804 fmicb-08-00804 April 29, 2017 Time: 14:57 # 2 Bajpai et al. Antibacterial Potential of (C)-Lariciresinol found that currently available preservation techniques have not and identified by Dr. Phuong Thien Thuong at the Department provided optimal results to control or retard the growth of of Pharmaceutical Analysis and Herbal Standardization, National foodborne and food spoilage pathogens in vivo (Aneja et al., Institute of Medicinal Materials, Vietnam. A voucher specimen 2014). was deposited at the herbarium of the National Institute of On the other hand, current scenario in drug discovery Medicinal Materials, Hanoi, Vietnam, as well as the Laboratory of and development has consistently showed development of Pharmacognosy at the College of Pharmacy, Chungnam National resistance among the foodborne pathogens to the commercially University, Daejeon, Korea. available antibiotics (Militello et al., 2011). Though some synthetic antimicrobials have shown profound efficacy to control Extraction, Isolation, and foodborne pathogens (Shakiba et al., 2011; Shen et al., 2014), they Characterization of (C)-Lariciresinol have shown to exhibit several side effects as a serious human- (C)-Lariciresinol was obtained from the roots of R. philippinensis health threatening, including toxic, carcinogenic, and teratogenic by chromatographic methods. Briefly, the ethanol extract of effects (Hsouna et al., 2011). This has caused an alarming threat R. philippinensis (150 g) was suspended in H O (1.5 L) and to the consumers to acquire contamination free food or food 2 partitioned with CH Cl (2 L × 3) to yield CH Cl extract. products. 2 2 2 2 The CH Cl -soluble fraction (50 g) was subjected to silica gel For decades, plants or plant-based phyto-constituents have 2 2 VLC and eluted with n-hexane-EtOAc (20:1, 10:1, 5:1, 3:1, 2:1) been used as alternative means for the prevention and treatment and CHCl -MeOH (8:1) to afford six fractions (D-1 ! D-6). of various diseases, both in modern and traditional medicine 3 Fraction D-6 (10 g) was divided into 11 sub-fractions (D-6-1 ! system (Pandey and Rizvi, 2009; Vauzour et al., 2010; Bajpai et al., D-6-11) using MPLC with a gradient of MeOH-H O (10:90 ! 2015). Plant extracts from Trachyspermum ammi (L.) were found 2 100:0, 7 L). (C)-Lariciresinol (t 33.0 min, 31 mg) was obtained to be effectivive against different foodborne pathogens (Paul et al., R from D-6-3 (360 mg) by HPLC model 1200 using a Zorbax SB- 2011). Also, olive and oregano derived extracts found to effective C18 analytical column (4.6 mm × 150 mm, 5 mm particle size), against different foodborne pathogens includings, S. aureus, Agilent, Germany eluting with MeOH-H O (45:55, 4 mL/min, S. enterica, L. monocytogenes, and E. coli O157:H7 (Friedman 2 UV 254 nm). (C)-Lariciresinol: brownish amorphous powder, et al., 2013). Polyphenols and bioactive compounds extracted 1H NMR (300 MHz, methanol-d ): 2.38 (1H, m, H-8), 2.47 (1H, from Camellia sinensis showed significant inhibitory effects agaist 4 dd, J D 13.1, 11.7, H -7’), 2.72 (1H, m, H-8’), 2.91 (1H, dd, E. coli (Noormandi and Dabaghzadeh, 2015). In the present a J D 13.1, 4.5, H -7’), 3.63 (1H, dd, J D 10.8, 6.6, H -9), 3.72 study, a polyphenolic lignan, (C)-lariciresinol isolated from the b a (1H, dd, J D 8.1, 6.1, H -9’), 3.82 (1H, overlapped, H -9), 3.97 roots of Rubia philippinensis was assessed for its antimicrobial a b (1H, dd, J D 8.1, 6.1, H -9’), 4.75 (1H, d, J D 6.9, H-7), 6.63 efficacy against selected foodborne pathogens, Staphylococcus b (1H, dd, J D 8.0, 1.2, H-6’), 6.73 (1H, d, J D 8.0, H-5’), 6.78 (3H, aureus and Escherichia coli O157:H7. overlapped, H-6, H-5, H-2’), 6.91 (1H, d, J D 1.2, H-2); 13C NMR (75 MHz, methanol-d4): 135.7 (C-1), 110.6 (C-2), 148.9 (C-3), MATERIALS AND METHODS 146.9 (C-4), 116.0 (C-5), 119.8 (C-6), 83.9 (C-7), 53.9 (C-8), 60.4 (C-9), 133.5 (C-1’), 113.4 (C-2’), 148.9 (C-3’), 145.7 (C-4’), 116.2 Chemicals and Reagents (C-5’), 122.1 (C-6’), 33.6 (C-7’), 43.8 (C-8’), 73.4 (C-9’), 56.3, 56.3 × The nutrient broth (NB) medium was purchased from (2 OCH3-3,3’). Difco (USA). Other chemicals and reagents used were of very pure and high analytical grade. Test samples of (C)- Determination of Antibacterial Activity of lariciresinol isolated from R. philippinensis were prepared in (C)-Lariciresinol 1% dimethyl sulfoxide (DMSO) (Sigma-Aldrich, Germany). Standard agar diffusion method was used for antibacterial Spectrophotometric measurements were made using an enzyme- assay (Bajpai and Kang, 2010). Petri plates were prepared linked immunosorbent assay (ELISA) instrument (Tecan, by pouring 20 ml of LB medium and allowed to solidify. Infinite M200, Männedorf, Switzerland) was used. Plates were dried, and 100 mL of standardized inoculum containing approximately 107 CFU/mL of bacterial suspension Test Foodborne Pathogens was poured and uniformly spread. The inoculum was allowed Two selected foodborne pathogenic bacteria one Gram-positive to dry for 5 min. The compound was dissolved in 5% (Staphylococcus aureus KCTC1621), and one Gram-negative DMSO, and a Whatman No. 1 sterile filter paper disk (6 mm (Escherichia coli O157:H7, shiga-toxin producing bacterium) diameter) was impregnated with 50 mL of the compound (C)- were procured from the Korean Collection for Type Cultures lariciresinol corresponding to 250 mg/disk. Negative controls (KCTC, Korea) and used in this study. All the bacterial strains were prepared using the same solvent that was employed to were grown in the NB and incubated at 37◦C. The bacterial dissolve the sample. The plates were incubated at 37◦C for strains were maintained on nutrient agar slants at 4◦C.
Load more

Recommended publications
  • Fronza, Marcio Thesis
    Phytochemical investigation of the roots of Peltodon longipes and in vitro cytotoxic studies of abietane diterpenes INAUGURALDISSERTATION zur Erlangung des Doktorgrades der Fakultät für Chemie, Pharmazie und Geowissenschaften der Albert-Ludwigs-Universität Freiburg im Breisgau vorgelegt von Marcio Fronza aus Tucunduva, RS (Brasilien) June 2011 Dekan: Prof. Dr. Harald Hillebrecht Leiterin der Arbeit: Prof. Dr. Irmgard Merfort Referentin: Prof. Dr. Irmgard Merfort Korreferent: Prof. Dr. Stefan Laufer Drittprüfer: Prof. Dr. Andreas Bechthold Tag der Verkündigung des Prüfungsergebnisses: 15-07-2011 Parts of this work have been published in the following conference presentations and publications: Publications Fronza M., Lamy E., Günther S., Murillo R., Heinzmann B., Laufer S., Merfort I. In vitro cytotoxic molecular mechanism studies of abietane diterpenes from Peltodon longipes . In preparation. Fronza M., Murillo R., Ślusarczyk S., Adams M., Hamburger M., Heinzmann B., Laufer S., Merfort I. In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and S. sahendica . Bioorganic & Medicinal Chemistry, in press . Geller F., Schmidt C., Gottert M., Fronza M., Heinzmann B., Flores E.M., Merfort I., Laufer S. Identification of rosmarinic acid as the major active compound constituent in Cordia americana . Journal of Ethnopharmacology . v.130, p.333 - 338, 2010. Schmidt C. A., Fronza M., Gottert M., Geller F., Laufer S., Merfort I. Biological studies on Brazilian plants used in wound healing. Journal of Ethnopharmacology . v.122, p.523 - 532, 2009. Fronza M., Heinzmann B., Hamburger M., Laufer S., Merfort I. Determination of the wound healing effect of Calendula extracts using the scratch assay with 3T3 fibroblasts. Journal of Ethnopharmacology .
    [Show full text]
  • (D. Don Endl) and Taxodium Distichum (L. Rich) Cultivated in Egypt
    Comparative Pharmacognostical Study and Tissue Culture of Sequoia sempervirens (D. Don Endl) and Taxodium distichum (L. Rich) Cultivated in Egypt A thesis submitted by: Mahmoud Anter Mohamed Arafat Demonstrator of Pharmacognosy Department, Faculty of Pharmacy, Nahda University For the partial fulfillment of the M.Sc. in Pharmaceutical Sciences (Pharmacognosy) Under the supervision of: Prof. Dr. Seham Salah El-Din El-Hawary Professor of Pharmacognosy, Department of Pharmacognosy, Faculty of Pharmacy, Cairo University Assistant Prof. Mohamed Abd El-Atty Rabeh Assistant Professor of Pharmacognosy, Department of Pharmacognosy, Faculty of Pharmacy, Cairo University Assistant Prof. Essam M. Abd El-Kadder Assistant Professor at Horticulture Research Institute Agricultural Research Center Pharmacognosy Department Faculty of Pharmacy Cairo University 2018 1 Abstract: Aiming to identify and authenticate Sequoia sempervirens (D.Don Endl) and Taxodium distichum (L.Rich) cultivated in Egypt. RAPD technique was employed to identify unique DNA markers and establish a typical fingerprint for S. sempervirens and T. distichum. The amplification profile of S. sempervirens was screened and a total of 18 different RAPD fragments had been recorded while the amplification profile of T. distichum was screened and a total of 15 different RAPD fragments had been recorded. Macromorphological and micromorphological studies of S. sempervirens and T. distichum had been done. The results of preliminary phytochemical screening of both plants showed the absence of alkaloids, anthraquinones, catechol tannins or cardiac glycosides in non-flowering parts of S. sempervirens and T. distichum. Sterols and/or triterpenoids, pyrogallol tannins, carbohydrate and/or glycosides and flavonoids were detected in all of the tested parts of the plants.
    [Show full text]
  • Synthesis of New Sulfurated Derivatives of Natural and Synthetic Systems As Multitarget Anticancer Agents and Development of New Drug Discovery Methodologies
    Department of Pharmaceutical Sciences PhD Course in Pharmaceutical Sciences (XXIX Cycle) Synthesis of New Sulfurated Derivatives of Natural and Synthetic Systems as Multitarget Anticancer Agents and Development of New Drug Discovery Methodologies Supervisor: Prof. Anna SPARATORE Coordinator: Prof. Marco DE AMICI PhD Thesis of: Elena Gabriele R10658 Academic year 2015/2016 “I don’t believe there would be any science at all without intuition.” Rita Levi Montalcini A mio marito e ai miei genitori Preface This thesis is divided in two parts. The former has been carried out at the Universitá degli Studi di Milano, department of Pharmaceutical Sciences, in the research group of Professor Anna Sparatore. This project treats the synthesis of new sulfurated compounds with the aim of obtaining anticancer agents acting through a multitarget mechanism. This part, entitled "design and synthesis of new derivatives of natural and synthetic systems endowed with anticancer activity, through a multitarget mechanism" is discussed from page 1 to page 149. The latter has been developed at Swiss Federal Institute of Technology in Zurich (ETH Zurich), Institute of Pharmaceutical Sciences (IPW), under the supervision and in the research group of Professor Dario Neri. This project explains the advantages of using DNA-encoded chemical libraries (DECLs) in drug discovery process. In particular, since in the majority of cases DECLs require at least one-step of amide bond formation between amino modified DNA and a carboxylic acid, we optimized a new methodology of synthesis in order to facilitate the construction of single-pharmacophore libraries (DECLs). This part, entitled "optimized reaction conditions for amide bond formation in DNA-encoded combinatorial libraries" is discussed from page 151 to page 187.
    [Show full text]
  • <I>Agrobacterium Rhizogenes</I>
    ORIGINAL ARTICLES Department of Biology and Pharmaceutical Botany1, Medical University of Łódz;´ Department of Phytochemistry2, Institute of Pharmacology, Polish Academy of Sciences, Kraków; Intercollegiate Faculty of Biotechnology3, University of Gdansk and Medical University of Gdansk,´ Department of Biotechnology, Laboratory of Plant Protection and Biotechnology, Gdansk,´ Poland Genetic transformation of Salvia austriaca by Agrobacterium rhizogenes and diterpenoid isolation Ł. Kuzma´ 1, W. Kisiel 2, A. Królicka 3, H. Wysokinska´ 1 Received May 6, 2011, accepted June 6, 2011 Dr. Łukasz Ku´zma, Department of Biology and Pharmaceutical Botany, Medical University of Łód´z, Muszy´nskiego 1, 90-151 Łód´z, Poland [email protected] Pharmazie 66: 904–907 (2011) doi: 10.1691/ph.2011.1586 Hairy roots of Salvia austriaca Jacq. transformed with Agrobacterium rhizogenes strain A4 were obtained and transgenic status of the roots was confirmed by polymerase chain reaction (PCR) using rolB and rolC specific primers. The root cultures growing in half-strength Gamborg (1/2 B5) liquid medium supple- mented with sucrose (30 g L−1) under light conditions (photoperiod: 16 h light/8 h dark) were examined for their ability to produce diterpenoids. From n-hexane extract the abietane-type diterpenoids royleanone, 15-deoxyfuerstione and taxodione were isolated and identified. This is the first report on the genetic transformation of S. austriaca. 1. Introduction 2. Investigations, results and discussion Salvia is the largest genus in the family Lamiaceae with over Hairy roots of S. austriaca were induced by infection of leaves 900 species in the world. Many sage species have been culti- (leaf laminas and petioles) and shoot tips from in vitro grown vated and used as medicinal plants for the treatment of common shoots with Agrobacterium rhizogenes strain A4.
    [Show full text]
  • Forested Wetlands of the Southern United States: a Bibliography William Conner Clemson University, [email protected]
    Clemson University TigerPrints Publications Plant and Environmental Sciences 10-2001 Forested Wetlands of the Southern United States: A Bibliography William Conner Clemson University, [email protected] Nicole L. Hill Evander M. Whitehead William S. Busbee Marceau A. Ratard See next page for additional authors Follow this and additional works at: https://tigerprints.clemson.edu/ag_pubs Part of the Forest Sciences Commons Recommended Citation Please use publisher's recommended citation. This Article is brought to you for free and open access by the Plant and Environmental Sciences at TigerPrints. It has been accepted for inclusion in Publications by an authorized administrator of TigerPrints. For more information, please contact [email protected]. Authors William Conner, Nicole L. Hill, Evander M. Whitehead, William S. Busbee, Marceau A. Ratard, Mehmet Ozalp, Darrell L. Smith, and James P. Marshall This article is available at TigerPrints: https://tigerprints.clemson.edu/ag_pubs/3 United States Department of Agriculture Forest Service Forested Wetlands of the Southern United States: A Bibliography Southern Research Station William H. Conner, Nicole L. Hill, Evander M. Whitehead, General Technical William S. Busbee, Marceau A. Ratard, Mehmet Ozalp, Report SRS-43 Darrel L. Smith, and James P. Marshall The Authors William H. Conner, Professor, Clemson University, Baruch Institute of Coastal Ecology and Forest Science, Clemson University, Georgetown, SC; Nicole L. Hill, Land Protection Specialist, Southwest Michigan Land Conservancy, Kalamazoo, MI; Evander M. Whitehead, Graduate Student, University of South Carolina, Columbia, SC; William S. Busbee, Graduate Student, Greenville, SC; and Marceau A. Ratard, Mehmet Ozalp, and James P. Marshall, Graduate Students, Forestry Department, Clemson University, Clemson, SC, respectively.
    [Show full text]
  • Natural Products from the Cretaceous Relict Metasequoia Glyptostroboides Hu & Cheng—A Molecular Reservoir from the Ancient World with Potential in Modern Medicine
    Phytochem Rev (2016) 15:161–195 DOI 10.1007/s11101-015-9395-3 Growing with dinosaurs: natural products from the Cretaceous relict Metasequoia glyptostroboides Hu & Cheng—a molecular reservoir from the ancient world with potential in modern medicine Ole Johan Juvik • Xuan Hong Thy Nguyen • Heidi Lie Andersen • Torgils Fossen Received: 21 November 2014 / Accepted: 10 February 2015 / Published online: 22 February 2015 Ó The Author(s) 2015. This article is published with open access at Springerlink.com Abstract After the sensational rediscovery of living paleobotany are covered. Initial spectral analysis of exemplars of the Cretaceous relict Metasequoia glyp- recently discovered intact 53 million year old wood tostroboides—a tree previously known exclusively and amber of Metasequoia strongly indicate that the from fossils from various locations in the northern tree has remained unchanged for millions of years at hemisphere, there has been an increasing interest in the molecular level. discovery of novel natural products from this unique plant source. This article includes the first complete Keywords Metasequoia glyptostroboides Á Natural compilation of natural products reported from M. products Á Biological activity Á Paleobotany Á Living glyptostroboides during the entire period in which the fossil tree has been investigated (1954–2014) with main focus on the compounds specific to this plant source. Studies on the biological activity of pure compounds and extracts derived from M. glyptostroboides are Introduction reviewed for the first time. The unique potential of M. glyptostroboides as a source of bioactive constituents Metasequoia glyptostroboides Hu et Cheng (Cupres- is founded on the fact that the tree seems to have saceae) is a deciduous conifer native to southeast survived unchanged since the Cretaceous era.
    [Show full text]
  • Types of DRUGS ACTING on DNA (In Chapter 9) Intercalating Agents
    5/10/2017 Chap. 9 - DRUGS TARGETING NUCLEIC ACIDS DNA & RNA Types of DRUGS ACTING on DNA (in chapter 9) Intercalating agents Topoisomerase poisons Alkylating agents Metallating agents Chain cutters Chain terminators Control of gene transcription (and epigenetics) 1 © Oxford University Press, 2013 DRUGS ACTING ON DNA Intercalating agents Mechanism of action • Contain planar aromatic or heteroaromatic ring systems • Planar systems slip between the layers of nucleic acid pairs and disrupt the shape of the helix • A preference is often shown for either the minor or major groove • Intercalation prevents replication and transcription • Intercalation can inhibit topoisomerases too 2 © Oxford University Press, 2013 1 5/10/2017 Intercalating agents Proflavine, also called diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria. It has been used in the form of the dihydrochloride and hemisulfate salts as a topical antiseptic, and was formerly used as a urinary antiseptic. Proflavine is toxic and carcinogenic in mammals and so it is used only as a surface disinfectant or for treating superficial wounds. Proflavine is also known to have a mutagenic effect on DNA by intercalating between nucleic acid base pairs. It differs from most other mutagenic components by causing basepair-deletions or basepair- insertions and not substitutions. NH3 Cl Ar NH3 Cl H2N N NH2 HOSO Planar tricyclic system NH3 3 The amino substituents are protonated Ar Used as a topical antibacterial agent in WW II NH3 HOSO
    [Show full text]
  • Syntheses of Catechol Diterpenes and Their Biological Activities
    No.150 No.150 Syntheses of Catechol Diterpenes and Their Biological Activities Masahiro TADA Professor Emeritus Tokyo University of Agriculture and Technology Fuchu, Tokyo 183-8509, Japan 1. Biological activities of catechol diterpenes in food have been reported. Anti-oxidants in foods include vitamins, sulfur compounds, and many polyphenols. Because A bioactive organic compound has a unique three- the polyphenols can be oxidized by oxygen, they are unstable dimensional structure with specific functional groups in in air. Natural polyphenols can be classified as flavonoids (e.g., required positions on the skeleton. In general, derivatives of catechins in teas), stilbenes (e.g., resveratrol in wines), phenolic the same skeleton without the functional groups show very low diterpenes (anti-oxidants in rosemary), phloroglucinols (anti- or no biological activity. Synthesis of a bioactive compound oxidants in hops) and so on. Many anti-oxidants also show requires easy introduction of the functional groups into the other various bioactivities, such as plant defense compounds skeleton. Successful synthesis of a bioactive compound with against fungi, bacteria, or insects.1-10) a complex structure may result in the discovery of novel organic reactions, but may provide only a few mg of the desired compound. However, investigation on the biological activities of a compound requires a large amount of the compound. 2. Ortho-quinone and ortho-quinone methide Development of a facile synthesis of an important bioactive compound in large quantities may produce new science. Among the polyphenols, catechols are easily oxidized to Recently, many studies on the bioactivity of anti-oxidants ortho-quinones, which are tautomeric isomers of 2-hydroxy-1,4- O O O HO 100% O O O ? HO R R Fig.
    [Show full text]
  • Pharmacological Prospects of Oxygenated Abietane-Type Diterpenoids from Taxodium Distichum Cones
    Advances in Biological Chemistry, 2014, 4, 109-115 Published Online April 2014 in SciRes. http://www.scirp.org/journal/abc http://dx.doi.org/10.4236/abc.2014.42015 Pharmacological Prospects of Oxygenated Abietane-Type Diterpenoids from Taxodium distichum Cones Norihisa Kusumoto1,2*, Nobuhiro Aburai2, Tatsuya Ashitani2,3, Koetsu Takahashi2,3, Ken-ichi Kimura2,4 1Institute of Wood Technology, Akita Prefectural University, Noshiro, Japan 2The United Graduate School of Agricultural Sciences, Iwate University, Morioka, Japan 3Faculty of Agriculture, Yamagata University, Tsuruoka, Japan 4Graduate School of Agriculture, Iwate University, Morioka, Japan Email: *[email protected] Received 28 January 2014; revised 6 March 2014; accepted 15 March 2014 Copyright © 2014 by authors and Scientific Research Publishing Inc. This work is licensed under the Creative Commons Attribution International License (CC BY). http://creativecommons.org/licenses/by/4.0/ Abstract Eight naturally occurring diterpenoids, including 6,7-dehydroroyleanone, taxodal, taxodione, sal- vinolone, 14-deoxycoleon U, 5,6-dehydrosugiol, sandaracopimaric acid, and xanthoperol were isolated from Taxodium distichum cones and their biological properties evaluated in vitro against six different biological screening targets. Taxodione showed potent activity against a number of different targets, and salvinolone and 14-deoxycoleon U showed remarkable inhibitory activities against prolyl oligopeptidase (POP) and 17α-hydroxylase/C17,20-lyase (CYP17), respectively. These three compounds also showed strong cytotoxic activities against HL60 and K562 human leukemia cells. The structure-activity relationships of these compounds have also been considered. The findings in this study could lead to enhanced pharmacological prospects for the natural abietane- type diterpenoids consisting in conifer cones. Keywords Abietane Diterpenoid; Conifer Cone; Antibacterial Activity; 17α-Hydroxylase/C17,20-Lyase; Prolyl Oligopeptidase; Cytotoxicity 1.
    [Show full text]
  • The Abietane Diterpene Taxodione Contributes to the Antioxidant
    The abietane diterpene taxodione contributes to the antioxidant activity of rosemary by-product in muscle tissue Sylvie Morel, Nathalie Saint, Manon Vitou, Alessandra Lo Cicero, Xavier Nissan, Barbara Vernus, Béatrice Chabi, Anne Bonnieu, Gerald Hugon, Françoise Fons, et al. To cite this version: Sylvie Morel, Nathalie Saint, Manon Vitou, Alessandra Lo Cicero, Xavier Nissan, et al.. The abietane diterpene taxodione contributes to the antioxidant activity of rosemary by-product in muscle tissue. Journal of Functional Foods, Elsevier, 2019, 62, pp.103565. 10.1016/j.jff.2019.103565. hal-02291837 HAL Id: hal-02291837 https://hal.archives-ouvertes.fr/hal-02291837 Submitted on 12 Mar 2020 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. -RXUQDORI)XQFWLRQDO)RRGV Contents lists available at ScienceDirect Journal of Functional Foods journal homepage: www.elsevier.com/locate/jff The abietane diterpene taxodione contributes to the antioxidant activity of 7 rosemary by-product in muscle tissue Sylvie Morela,1, Nathalie Saintb,1, Manon Vitoua, Alessandra Lo
    [Show full text]
  • Brief Communication
    Antibacterial abietane-type diterpenoid, taxodone from Metasequoia glyptostroboides Miki ex Hu 533 Brief communication Antibacterial abietane-type diterpenoid, taxodone from Metasequoia glyptostroboides Miki ex Hu VIVEK K BAJPAI and SUN CHUL KANG* Department of Biotechnology, Daegu University, Kyoungsan, Kyoungbook 712-714, Republic of Korea *Corresponding author (Fax, +82-53-850-6559; Email, [email protected]) In an attempt to isolate bioactive constituents, ethyl acetate cone extract of Metasequoia glyptostroboides was subjected to a column chromatographic analysis that resulted in isolation of an abietane-type diterpenoid, taxodone. Its structure was elucidated by spectroscopic means. Further, taxodone showed potential antibacterial effect as diameters of zones of inhibition against foodborne pathogenic bacteria, such as Listeria monocytogenes ATCC 19166, Salmonella typhimurium KCTC 2515, S. enteritidis KCTC 2021, Escherichia coli ATCC 8739, E. coli O157:H7 ATCC 43888, Enterobacter aerogenes KCTC 2190, Staphylococcus aureus ATCC 6538 and S. aureus KCTC 1916, were found in the range of 9.4 to 14.2 mm. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of taxodone against the employed bacterial pathogens were found in the range of 250 to 1000 and 250 to <2000 μg/ml, respectively. Also the compound had a strong antibacterial effect on the viable counts of the tested bacteria. These fi ndings indicate that the bioactive compound taxodone present in M. glyptostroboides could be used as an antibacterial agent in food industry to inhibit the growth of certain important foodborne pathogens. [Bajpai V K and Kang S C 2010 Antibacterial abietane-type diterpenoid, taxodone from Metasequoia glyptostroboides Miki ex Hu; J.
    [Show full text]
  • Potential Role of Plant Extracts and Phytochemicals Against Foodborne Pathogens
    applied sciences Review Potential Role of Plant Extracts and Phytochemicals Against Foodborne Pathogens Farhat Ullah 1, Muhammad Ayaz 1,*, Abdul Sadiq 1, Farman Ullah 2, Ishtiaq Hussain 3, Muhammad Shahid 4, Zhanibek Yessimbekov 5, Anjana Adhikari-Devkota 6 and Hari Prasad Devkota 6,7,* 1 Department of Pharmacy, University of Malakand, Khyber Pakhtunkhwa (KP) 18000, Pakistan; [email protected] (F.U.); [email protected] (A.S.) 2 Department of Pharmacy, Kohat University of Science and Technology (KUST), Kohat 26000, Khyber Pakhtunkhwa, Pakistan; [email protected] 3 Department of Pharmaceutical Sciences, Abbottabad University of Science and Technology, Abbottabad 22010, Pakistan; [email protected] 4 Department of Pharmacy, Sarhad University of Science and Information Technology, Peshawar KPK 25000, Pakistan; [email protected] 5 Shakarim State University of Semey, Semey 071412, Kazakhstan; [email protected] 6 Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan; [email protected] 7 Program for Leading Graduate Schools, Health Life Sciences: Interdisciplinary and Glocal Oriendted (HIGO) Program, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan * Correspondence: [email protected] (M.A.); [email protected] (H.P.D.) Received: 26 May 2020; Accepted: 29 June 2020; Published: 2 July 2020 Abstract: Foodborne diseases are one of the major causes of morbidity and mortality, especially in low-income countries with poor sanitation and inadequate healthcare facilities. The foremost bacterial pathogens responsible for global outbreaks include Salmonella species, Campylobacter jejuni, Escherichia coli, Shigella sp., Vibrio, Listeria monocytogenes and Clostridium botulinum. Among the viral and parasitic pathogens, norovirus, hepatitis A virus, Giardia lamblia, Trichinella spiralis, Toxoplasma and Entamoeba histolytica are commonly associated with foodborne diseases.
    [Show full text]