DOCSLIB.ORG

Applications of the Achmatowicz Rearrangement in Natural Product Synthesis

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Applications of the Achmatowicz Rearrangement in Natural Product Synthesis Hobson, Stephen (2010) Applications of the achmatowicz rearrangement in natural product synthesis. PhD thesis. http://theses.gla.ac.uk/1660/ Copyright and moral rights for this thesis are retained by the author A copy can be downloaded for personal non-commercial research or study, without prior permission or charge This thesis cannot be reproduced or quoted extensively from without first obtaining permission in writing from the Author The content must not be changed in any way or sold commercially in any format or medium without the formal permission of the Author When referring to this work, full bibliographic details including the author, title, awarding institution and date of the thesis must be given. Glasgow Theses Service http://theses.gla.ac.uk/ [email protected] Applications of the Achmatowicz Rearrangement in Natural Product Synthesis Stephen Hobson B.Sc (Hons) Submitted in fulfilment of the requirements for the Degree of Doctor of Philosophy Department of Chemistry Faculty of Physical Sciences University of Glasgow Submitted January 2010 ii Abstract The structurally related PM-94128 and Ajudazols A and B exhibit differing biological activities but share the isocoumarin core structure. PM-94128 belongs to a large family of compounds known as the aminodihydroisocoumarins and was isolated in 1997. It has been shown to be an inhibitor of DNA and RNA synthesis and have potent cytotoxic activity in vivo . The Ajudazols A and B were isolated in 2004 and have antifungal activity against several important food spoilers. The work that follows details the design and development of a novel method for the generation of the isocoumarin core from isobenzofuran utilizing the Achmatowicz rearrangement of α-hydroxyisobenzofurans. Spirocyclic pyrans such as Polymaxenolide are structurally complex molecules, containing large amounts of functionality. The biological activity of Polymaxenolide is unknown and there have been no total syntheses reported to date. ii iii Also reported in this thesis is the design and synthesis of a model system of Polymaxenolide, using the Achmatowicz rearrangement of α-hydroxyfurans. iii iv Table of Contents Abstract...................................................................................... ii Table of Contents ..........................................................................iv List of Figures ...............................................................................vi List of Tables............................................................................... vii List of Schemes ............................................................................ vii Acknowledgments ..........................................................................xi Author Declaration ........................................................................ xii Abbreviations ............................................................................. xiii 1. Introduction.............................................................................. 1 1.1. Isocoumarins...................................................................... 1 1.1.1. Bacillus isocoumarins ...................................................... 1 1.1.2. Streptomycetes isocoumarins ............................................ 2 1.1.3. Xenorhabdus isocoumarins................................................ 3 1.1.4. Bachiphelacin ............................................................... 3 1.1.5. PM-94128 and Y-05460M-A ................................................ 4 1.1.6. Amicoumacin A to C ....................................................... 5 1.1.7. AI-77s and Sg17-1-4 ........................................................ 9 1.1.8. Shioiri’s synthesis of AI-77-B............................................. 12 1.1.9. Kotsuki’s synthesis of AI-77-B ........................................... 15 1.1.10. Vallee’s sythesis of PM-94128......................................... 19 1.1.11. Other notable syntheses............................................... 21 1.2. Isochromanones................................................................. 24 1.2.1. Ajudazol A and B .......................................................... 24 1.2.2. Taylor’s synthesis of the C15-C29 fragment, 104..................... 28 1.2.3. Rizzacasa’s synthesis of the C9-C29 fragment 121 ................... 31 1.3. Other isocoumarin containing natural products............................ 35 1.4. Biosynthetic origin.............................................................. 38 2. Results and discussion ................................................................. 44 2.1. Synthesis of PM-94128 ......................................................... 44 2.1.1. Proline organocatalysis ................................................... 45 2.1.2. Initial synthetic efforts................................................... 48 2.2. An alternate approach ......................................................... 55 2.2.1. Model system synthesis................................................... 57 2.2.2. Studies towards the synthesis of Ajudazol A .......................... 67 2.2.3. Mitsunobu inversion....................................................... 73 2.2.4. An unexpected product .................................................. 75 2.2.5. Studies towards the Ajudazol A C15-C29 fragment. ................. 77 2.3. Future work...................................................................... 79 2.3.1. Introduction of the C8 hydroxyl......................................... 79 2.3.2. Alkylation regioselectivity ............................................... 81 2.3.3. Enantiopure Aldehyde .................................................... 81 2.3.4. Completion of the C1-C14 fragment.................................... 82 2.3.5. Further work ............................................................... 82 3. Experimental............................................................................ 85 4. Introduction............................................................................129 4.1. Spirocyclic pyrans .............................................................129 4.2. Isolation and characterization ...............................................129 4.3. Biosynthesis.....................................................................131 4.4. Structural features ............................................................133 iv v 4.5. Spirocyclic pyrans .............................................................134 4.5.1. Ring closing metathesis .................................................134 4.5.2. Spiroannulation...........................................................137 4.5.3. Prins cyclisations .........................................................138 4.5.4. Pauson Khand .............................................................140 4.5.5. Other methods............................................................141 5. Results and discussion ................................................................143 5.1. Spirocyclic natural products .................................................143 5.1.1. Initial findings ............................................................143 5.1.2. Retrosynthesis ............................................................145 5.1.3. Synthesizing lactol, 397. ................................................145 5.1.4. Other ring systems .......................................................148 5.1.5. Synthesis of the [4.5] spirocycle .......................................148 5.1.6. Optimisation of the cyclisation protocol..............................151 5.2. Methoxy directed cyclisations ...............................................152 5.2.1. First synthetic route .....................................................153 5.2.2. Palladium cross coupling reactions ....................................156 5.2.3. Molybdenum catalyzed allylic substitution...........................161 5.2.4. Original route .............................................................162 5.2.5. Cyclisation vs dehydration ..............................................162 5.3. Future Work ....................................................................166 5.3.1. Spirocyclic products .....................................................166 5.3.2. Methoxy directed cyclisations..........................................168 6. Experimental...........................................................................169 7. Appendices .............................................................................206 7.1. Appendix 1 - Reaction of diene 208 and dienophile 198 .................206 7.2. Appendix 2 - Reaction of modified dienes 202 and 206..................207 7.3. Appendix 3 - Microwave conditions. ........................................208 7.4. Appendix 4 - Neat Diels Alder series........................................209 7.5. Appendix 5 – X-ray data for 198 .............................................209 7.6. Appendix 6 – X-Ray data for 244.............................................211 7.7. Appendix 7 – X- Ray data for 261 ............................................214 7.8. Appendix 8 – X-Ray data for 264.............................................217 7.9. Appendix 9 – X-ray data for 276 .............................................221 7.10. Appendix 10 – X-ray data for 289 .........................................224 7.11. Appendix 11 – X-ray data for 298 .........................................228 7.12. Appendix 12 – Org. Lett., 2008, 10 , 2813 ...............................233
Load more

Recommended publications
  • Importance of the 4-Substituted Resorcinol Moiety
    International Journal of Molecular Sciences Article Urolithin and Reduced Urolithin Derivatives as Potent Inhibitors of Tyrosinase and Melanogenesis: Importance of the 4-Substituted Resorcinol Moiety Sanggwon Lee 1,†, Heejeong Choi 1,† , Yujin Park 1, Hee Jin Jung 1 , Sultan Ullah 2, Inkyu Choi 1, Dongwan Kang 1, Chaeun Park 1, Il Young Ryu 1, Yeongmu Jeong 1, YeJi Hwang 1, Sojeong Hong 1, Pusoon Chun 3 and Hyung Ryong Moon 1,* 1 College of Pharmacy, Pusan National University, Busan 46241, Korea; [email protected] (S.L.); [email protected] (H.C.); [email protected] (Y.P.); [email protected] (H.J.J.); [email protected] (I.C.); [email protected] (D.K.); [email protected] (C.P.); [email protected] (I.Y.R.); [email protected] (Y.J.); [email protected] (Y.H.); [email protected] (S.H.) 2 Department of Molecular Medicine, The Scripps Research Institute, Jupiter, FL 33458, USA; [email protected] 3 College of Pharmacy and Inje Institute of Pharmaceutical Sciences and Research, Inje University, Gimhae 50834, Korea; [email protected] * Correspondence: [email protected]; Tel.: +82-51-510-2815; Fax: +82-51-513-6754 † These authors (S. Lee and H. Choi) contributed equally to this work. Abstract: We previously reported (E)-β-phenyl-α,β-unsaturated carbonyl scaffold ((E)-PUSC) played an important role in showing high tyrosinase inhibitory activity and that derivatives with a 4- Citation: Lee, S.; Choi, H.; Park, Y.; substituted resorcinol moiety as the β-phenyl group of the scaffold resulted in the greatest tyrosinase Jung, H.J.; Ullah, S.; Choi, I.; Kang, D.; inhibitory activity.
    [Show full text]
  • Glycosides Pharmacognosy Dr
    GLYCOSIDES PHARMACOGNOSY DR. KIBOI Glycosides Glycosides • Glycosides consist of a sugar residue covalently bound to a different structure called the aglycone • The sugar residue is in its cyclic form and the point of attachment is the hydroxyl group of the hemiacetal function. The sugar moiety can be joined to the aglycone in various ways: 1.Oxygen (O-glycoside) 2.Sulphur (S-glycoside) 3.Nitrogen (N-glycoside) 4.Carbon ( Cglycoside) • α-Glycosides and β-glycosides are distinguished by the configuration of the hemiacetal hydroxyl group. • The majority of naturally-occurring glycosides are β-glycosides. • O-Glycosides can easily be cleaved into sugar and aglycone by hydrolysis with acids or enzymes. • Almost all plants that contain glycosides also contain enzymes that bring about their hydrolysis (glycosidases ). • Glycosides are usually soluble in water and in polar organic solvents, whereas aglycones are normally insoluble or only slightly soluble in water. • It is often very difficult to isolate intact glycosides because of their polar character. • Many important drugs are glycosides and their pharmacological effects are largely determined by the structure of the aglycone. • The term 'glycoside' is a very general one which embraces all the many and varied combinations of sugars and aglycones. • More precise terms are available to describe particular classes. Some of these terms refer to: 1.the sugar part of the molecule (e.g. glucoside ). 2.the aglycone (e.g. anthraquinone). 3.the physical or pharmacological property (e.g. saponin “soap-like ”, cardiac “having an action on the heart ”). • Modern system of naming glycosides uses the termination '-oside' (e.g. sennoside). • Although glycosides form a natural group in that they all contain a sugar unit, the aglycones are of such varied nature and complexity that glycosides vary very much in their physical and chemical properties and in their pharmacological action.
    [Show full text]
  • Antioxidant Content and Free Radical Scavenging Ability of Fresh Red Pummelo [Citrus Grandis (L.) Osbeck] Juice and Freeze-Dried Products
    J. Agric. Food Chem. 2007, 55, 2867−2872 2867 Antioxidant Content and Free Radical Scavenging Ability of Fresh Red Pummelo [Citrus grandis (L.) Osbeck] Juice and Freeze-Dried Products HSIU-LING TSAI,†,§ SAM K. C. CHANG,# AND SUE-JOAN CHANG*,† Department of Life Sciences, National Cheng Kung University, Tainan 701, Taiwan; Department of Food Nutrition, Chung Hwa College of Medical Technology, Jente, Tainan 717, Taiwan; and Department of Cereal and Food Sciences, North Dakota State University, Fargo, North Dakota 58105 The antioxidative phytochemicals in various fruits and vegetables are widely recognized for their role in scavenging free radicals, which are involved in the etiology of many chronic diseases. Colored fruits are especially considered a quality trait that correlates with their nutritional values and health benefits. The specific aim of this study was to investigate the antioxidants in the juice and freeze- dried flesh and peel of red pummelo and their ability to scavenge free radicals and compare them with those in white pummelo juice. The total phenolic content of red pummelo juice extracted by methanol (8.3 mg/mL) was found to be significantly higher than that of white pummelo juice (5.6 mg/mL). The carotenoid content of red pummelo juice was also significantly higher than that in white pummelo juice. The contents of vitamin C and δ-tocopherol in red pummelo juice were 472 and 0.35 µg/mL, respectively. The ability of the antioxidants found in red pummelo juice to scavenge radicals were found by methanol extraction to approximate that of BHA and vitamin C with a rapid rate in a kinetic model.
    [Show full text]
  • 11695634.Pdf
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Epsilon Open Archive SWEET AND BITTER TASTE IN ORGANIC CARROT Lars Kjellenberg Introductory Paper at the Faculty of Landscape Planning, Horticulture and Agricultural Science 2007:2 Swedish University of Agricultural Sciences Alnarp, September 2007 ISSN 1654-3580 SWEET AND BITTER TASTE IN ORGANIC CARROT Lars Kjellenberg Introductory Paper at the Faculty of Landscape Planning, Horticulture and Agricultural Science 2007:2 Swedish University of Agricultural Sciences Alnarp, September 2007 2 © by the author Table 1,2, and figure 1,2 3, 4 reprinted with the kind permission from CABI Publishing Table 3, 4,5 and figure 5, 6, 7, 10 reprinted with the kind permission from the American Chemical Society Table 6 reprinted with the kind permission from the author Thomas Alföldi Table 8 reprinted with the kind permission from Blackwell Publishing Inc. Figure 8, 9 reprinted with the kind permission from the author Tim Jacob 3 Summary Carrot, Daucus carota L., is valuable for its taste, good digestibility and high contents of provitamin A. Both epidemiological and nutritional studies have pointed out its positive impact on human health. The taste of carrots is a unique composition between sweet, fruity and more harsh or bitter flavours. Many factors affect the balance between the different flavours in carrots and thus contribute to the final taste. Sweet taste is more common in the centre and lower, tip, part of the carrot. The phloem is mostly sweeter and also bitterer than the xylem. Bitter taste is more often detected in the upper and outer part of the carrot.
    [Show full text]
  • Antiplasmodial Natural Products: an Update Nasir Tajuddeen and Fanie R
    Tajuddeen and Van Heerden Malar J (2019) 18:404 https://doi.org/10.1186/s12936-019-3026-1 Malaria Journal REVIEW Open Access Antiplasmodial natural products: an update Nasir Tajuddeen and Fanie R. Van Heerden* Abstract Background: Malaria remains a signifcant public health challenge in regions of the world where it is endemic. An unprecedented decline in malaria incidences was recorded during the last decade due to the availability of efective control interventions, such as the deployment of artemisinin-based combination therapy and insecticide-treated nets. However, according to the World Health Organization, malaria is staging a comeback, in part due to the develop- ment of drug resistance. Therefore, there is an urgent need to discover new anti-malarial drugs. This article reviews the literature on natural products with antiplasmodial activity that was reported between 2010 and 2017. Methods: Relevant literature was sourced by searching the major scientifc databases, including Web of Science, ScienceDirect, Scopus, SciFinder, Pubmed, and Google Scholar, using appropriate keyword combinations. Results and Discussion: A total of 1524 compounds from 397 relevant references, assayed against at least one strain of Plasmodium, were reported in the period under review. Out of these, 39% were described as new natural products, and 29% of the compounds had IC50 3.0 µM against at least one strain of Plasmodium. Several of these compounds have the potential to be developed into≤ viable anti-malarial drugs. Also, some of these compounds could play a role in malaria eradication by targeting gametocytes. However, the research into natural products with potential for block- ing the transmission of malaria is still in its infancy stage and needs to be vigorously pursued.
    [Show full text]
  • (EGCG): Preparations and Bioactivities
    Lipophilized Derivatives of Epigallocatechin Gallate (EGCG): Preparations and Bioactivities By Nishani Perera A thesis submitted to the School of Graduate Studies in Partial fulfillment of the requirement of the degree of Masters in Food Science Department of Biochemistry Memorial University of Newfoundland April 2015 ABSTRACT Green tea polyphenols (GTP) are a major source of dietary phenolics that render a myriad of health benefits. Among GTP, epigallocatechin gallate (EGCG) is dominant and has been considered as being effective in both food and biological systems. However, its application and benefits may be compromised due to limited absorption and bioavailability. In order to expand the application of EGCG to more diverse systems, it may be lipophilized through structural modification. In this work, lipophilized derivatives of EGCG were prepared by acylation with different chain lengths fatty acyl chlorides such as acetyl chloride, C2:0; propionyl chloride, C3:0; hexanoyl chloride, C6:0; octanoyl chloride, C8:0; dodecanoyl chloride, C12:0; octadecanoyl chloride, C18:0; and docosahexaenoyl chloride, C22:6. The resultant products, mainly tetra-esters, were purified and their bioactivities evaluated, including antioxidant activities in different model systems and anti-glycation activities. The lipophilicity of the esters increased with increasing chain length of the acyl group and also led to the enhancement of their antioxidant properties that were evaluated using assays such as 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging capacity, oxygen radical absorbance capacity (ORAC) and reducing power of the molecules involved. These findings strongly suggest that the EGCG ester derivatives have great potential as lipophilic alternatives to the water-soluble EGCG.
    [Show full text]
  • Fungal Endophytes As Efficient Sources of Plant-Derived Bioactive
    microorganisms Review Fungal Endophytes as Efficient Sources of Plant-Derived Bioactive Compounds and Their Prospective Applications in Natural Product Drug Discovery: Insights, Avenues, and Challenges Archana Singh 1,2, Dheeraj K. Singh 3,* , Ravindra N. Kharwar 2,* , James F. White 4,* and Surendra K. Gond 1,* 1 Department of Botany, MMV, Banaras Hindu University, Varanasi 221005, India; [email protected] 2 Department of Botany, Institute of Science, Banaras Hindu University, Varanasi 221005, India 3 Department of Botany, Harish Chandra Post Graduate College, Varanasi 221001, India 4 Department of Plant Biology, Rutgers University, New Brunswick, NJ 08901, USA * Correspondence: [email protected] (D.K.S.); [email protected] (R.N.K.); [email protected] (J.F.W.); [email protected] (S.K.G.) Abstract: Fungal endophytes are well-established sources of biologically active natural compounds with many producing pharmacologically valuable specific plant-derived products. This review details typical plant-derived medicinal compounds of several classes, including alkaloids, coumarins, flavonoids, glycosides, lignans, phenylpropanoids, quinones, saponins, terpenoids, and xanthones that are produced by endophytic fungi. This review covers the studies carried out since the first report of taxol biosynthesis by endophytic Taxomyces andreanae in 1993 up to mid-2020. The article also highlights the prospects of endophyte-dependent biosynthesis of such plant-derived pharma- cologically active compounds and the bottlenecks in the commercialization of this novel approach Citation: Singh, A.; Singh, D.K.; Kharwar, R.N.; White, J.F.; Gond, S.K. in the area of drug discovery. After recent updates in the field of ‘omics’ and ‘one strain many Fungal Endophytes as Efficient compounds’ (OSMAC) approach, fungal endophytes have emerged as strong unconventional source Sources of Plant-Derived Bioactive of such prized products.
    [Show full text]
  • ORTHOPTERA: ACRIDIDAE) and Diaprepes Abbreviatus (COLEOPTERA: CURCULIONIDAE)
    ANTIFEEDANT EFFECT OF COMMERCIAL CHEMICALS AND PLANT EXTRACTS AGAINST Schistocerca americana (ORTHOPTERA: ACRIDIDAE) AND Diaprepes abbreviatus (COLEOPTERA: CURCULIONIDAE) By ANDRES FELIPE SANDOVAL MOJICA A THESIS PRESENTED TO THE GRADUATE SCHOOL OF THE UNIVERSITY OF FLORIDA IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE UNIVERSITY OF FLORIDA 2009 1 © 2009 Andres Felipe Sandoval Mojica 2 To my family, the source of my strength 3 ACKNOWLEDGMENTS I thank my committee members Dr. John Capinera, Dr. Michael Scharf, and Dr. Heather McAuslane for their advice, support and commitment to this study. 4 TABLE OF CONTENTS page ACKNOWLEDGMENTS.................................................................................................................... 4 LIST OF TABLES................................................................................................................................ 7 LIST OF FIGURES .............................................................................................................................. 8 ABSTRACT ........................................................................................................................................ 10 CHAPTER 1 INTRODUCTION....................................................................................................................... 12 Conceptual Framework ............................................................................................................... 12 Pest Insects..................................................................................................................................
    [Show full text]
  • Chemistry of Secondary Polyphenols Produced During Processing of Tea and Selected Foods
    Int. J. Mol. Sci. 2010, 11, 14-40; doi:10.3390/ijms11010014 OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 www.mdpi.com/journal/ijms Review Chemistry of Secondary Polyphenols Produced during Processing of Tea and Selected Foods Takashi Tanaka *, Yosuke Matsuo and Isao Kouno Laboratory of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan; E-Mails: [email protected] (Y.M.); [email protected] (I.K.) * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +81-95-819-2433; Fax: +81-95-819-2477. Received: 19 November 2009; in revised form: 19 December 2009 / Accepted: 24 December 2009 / Published: 28 December 2009 Abstract: This review will discuss recent progress in the chemistry of secondary polyphenols produced during food processing. The production mechanism of the secondary polyphenols in black tea, whisky, cinnamon, and persimmon fruits will be introduced. In the process of black tea production, tea leaf catechins are enzymatically oxidized to yield a complex mixture of oxidation products, including theaflavins and thearubigins. Despite the importance of the beverage, most of the chemical constituents have not yet been confirmed due to the complexity of the mixture. However, the reaction mechanisms at the initial stages of catechin oxidation are explained by simple quinone–phenol coupling reactions. In vitro model experiments indicated the presence of interesting regio- and stereoselective reactions. Recent results on the reaction mechanisms will be introduced. During the aging of whisky in oak wood barrels, ellagitannins originating from oak wood are oxidized and react with ethanol to give characteristic secondary ellagitannins.
    [Show full text]
  • Dr. Duke's Phytochemical and Ethnobotanical Databases Chemicals Found in Artemisia Dracunculus
    Dr. Duke's Phytochemical and Ethnobotanical Databases Chemicals found in Artemisia dracunculus Activities Count Chemical Plant Part Low PPM High PPM StdDev Refernce Citation 0 (E)-2-DIHYDROXY-4- Plant -- METHOXY-4- METHOXYCINNAMIC-ACID- METHYL-ETHER 0 (E)-ARTEMIDIN Plant J.S. Glasby Dict.Pls Containing 2ndary Metabolite. 1991. 0 (Z)-ARTEMIDIN Plant J.S. Glasby Dict.Pls Containing 2ndary Metabolite. 1991. 0 1,2-DIMETHOXY-4-ALLYL- Shoot -- BENZENE 0 1,8-CINEOL Leaf Essent. Oil 50000.0 -0.6071044965246614 -- 0 1,8-CINEOL Essential Oil 68800.0 -0.23220200822943154 -- 67 1,8-CINEOLE Shoot 50.0 500.0 -0.12842761628622745 -- 0 1-(BUT-2-YNYL)- Root 270.0 -- ISOCOUMARIN 0 1-(BUT-2-YNYL)- Shoot 42.0 -- ISOCOUMARIN 0 2,4,6- Shoot 11.0 -- TRIMETHOXYCINNAMYL- ALCOHOL 0 2-CARBOXYARABINITOL Leaf 903.0 1.9532419928562945 Moore, B. D., Isidoro, E., Seemann, J. R. 1993. Distribution of 2- Carboxyarabinitol Among Plants. Phytochemistry 34 3: 703-707. Dept. Biochem. Univ. Nevada Reno 89557, USA. 0 2-HEPTANONE Plant -- 0 2-HYDROXY-4-METHOXY- Leaf 143.0 -- TRANS-CINNAMIC-ACID 0 3',5'-DIHYDROXY-4',7- Shoot 16.0 -- DIMETHOXY-FLAVANONE 0 3,4',5-TRIHYDROXY-3',7- Shoot 312.0 -- DIMETHOXY-FLAVANONE 0 3,4',5-TRIHYDROXY-7- Shoot 250.0 -- METHOXY-FLAVANONE 0 3-(BUT-CIS-1-YNYL)- Root 1500.0 -- ISOCOUMARIN 0 3-(BUT-TRANS-1-YNYL)-5- Root 50.0 -- HYDROXY-ISOCOUMARIN 0 3-(BUT-TRANS-1-YNYL)-8- Root 15.0 -- HYDROXY-ISOCOUMARIN Activities Count Chemical Plant Part Low PPM High PPM StdDev Refernce Citation 0 3-(BUT-TRANS-1-YNYL)- Root 100.0 -- ISOCOUMARIN 0 3-BUT-CIS-1-ENYL- Root 1500.0 -- ISOCOUMARIN 0 3-BUT-TRANS-1-ENYL-5- Root 50.0 -- HYDROXY-ISOCOUMARIN 0 3-BUT-TRANS-1-ENYL-8- Root 15.0 -- HYDROXY-ISOCOUMARIN 0 3-BUT-TRANS-1-ENYL- Root 100.0 -- ISOCOUMARIN 0 4-ALLYL-1,2- Shoot Essent.
    [Show full text]
  • Carrot Anthocyanins Genetics and Genomics: Status and Perspectives to Improve Its Application for the Food Colorant Industry
    G C A T T A C G G C A T genes Review Carrot Anthocyanins Genetics and Genomics: Status and Perspectives to Improve Its Application for the Food Colorant Industry Massimo Iorizzo 1,2,*, Julien Curaba 1, Marti Pottorff 1, Mario G. Ferruzzi 1, Philipp Simon 3,4 and Pablo F. Cavagnaro 5,6 1 Plants for Human Health Institute, North Carolina State University, Kannapolis, NC 28081, USA; [email protected] (J.C.); [email protected] (M.P.); [email protected] (M.G.F.) 2 Department of Horticultural Science, North Carolina State University, Raleigh, NC 27695, USA 3 Department of Horticulture, University of Wisconsin–Madison, Madison, WI 53706, USA; [email protected] 4 Vegetable Crops Research Unit, US Department of Agriculture–Agricultural Research Service, Madison, WI 53706, USA 5 National Scientific and Technical Research Council (CONICET), National Agricultural Technology Institute (INTA) E.E.A. La Consulta, Mendoza 5567, Argentina; [email protected] 6 Faculty of Agricultural Sciences, National University of Cuyo, Mendoza 5505, Argentina * Correspondence: [email protected] Received: 3 July 2020; Accepted: 31 July 2020; Published: 7 August 2020 Abstract: Purple or black carrots (Daucus carota ssp. sativus var. atrorubens Alef) are characterized by their dark purple- to black-colored roots, owing their appearance to high anthocyanin concentrations. In recent years, there has been increasing interest in the use of black carrot anthocyanins as natural food dyes. Black carrot roots contain large quantities of mono-acylated anthocyanins, which impart a measure of heat-, light- and pH-stability, enhancing the color-stability of food products over their shelf-life.
    [Show full text]
  • Chemical Constituents of Plants from the Genus Patrinia
    Natural Product Sciences 19(2) : 77-119 (2013) Chemical Constituents of Plants from the Genus Patrinia Ju Sun Kim and Sam Sik Kang* Natural Products Research Institute and College of Pharmacy, Seoul National University, Seoul 151-742, Korea Abstract − The genus Patrinia, belonging to the Valerianaceae family, includes ca. 20 species of herbaceous plants with yellow or white flowers, distributed in Korea, China, Siberia, and Japan. Among them, P. scabiosaefolia (yellow Patrinia), P. saniculaefolia, P. villosa (white Patrinia), and P. rupestris are found in Korea. Several members of this genus have long been used in folk medicine for the treatment of inflammation, wound healing, ascetics, and abdominal pain after childbirth. Thus far, ca. 217 constituents, namely flavonoids, iridoids, triterpenes, saponins, and others have been identified in this genus. Crude extract and isolated compounds have been found to exhibit anticancer, anti-inflammatory, antioxidant, antifungal, antibacterial, cytotoxic activities, lending support to the rationale behind several of its traditional uses. The present review compiles information concerning the phytochemistry and biological activities of Patrinia, with particular emphasis on P. villosa, as studied by our research group. Keywords − Valerianaceae, Patrinia species, Natural products chemistry, Biological activities Introduction of the compounds/extracts obtained from this plants. Patrinia is a genus of herbaceous plants in the Chemical Constituents Valerianaceae family. There are about 20 species native to grassy mountain habitats in China, Siberia, and Japan. The reported chemical constituents from the genus Among them, P. scabiosaefolia (yellow Patrinia), P. Patrinia number, thus far, approximtely 217, include saniculaefolia, P. villosa (white Patrinia), and P. rupestris flavonoids, iridoids, triterpenes, saponins, steroids, and a are found in Korea (Lee, 1989; Bae, 2000).
    [Show full text]