Chemistry of plant phosphorus compounds

Chemistry of Plant Phosphorus Compounds Chemistry of Plant Phosphorus Compounds Arlen W Frank AMSTERDAM • BOSTON • HEIDELBERG • LONDON • NEW YORK • OXFORD • PARIS SAN DIEGO • SAN FRANCISCO • SYDNEY • TOKYO Elsevier 225, Wyman Street, Waltham, MA 02451, USA The Boulevard, Langford Lane, Kidlington, Oxford OX5 GB, UK Radarweg 29, PO Box 211, 1000 AE Amsterdam, The Netherlands Copyright © 2013 Elsevier Inc All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher Permissions may be sought directly from Elsevier’s Science & Technology Rights Department in Oxford, UK: phone (ỵ44) (0) 1865 843830; fax (ỵ44) (0) 1865 853333; email: permissions@elsevier.com Alternatively you can submit your request online by visiting the Elsevier web site at http://elsevier.com/locate/ permissions, and selecting Obtaining permission to use Elsevier material Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products, instructions or ideas contained in the material herein Because of rapid advances in the medical sciences, in particular, independent verification of diagnoses and drug dosages should be made Library of Congress Cataloging-in-Publication Data Application Submitted British Library Cataloguing in Publication Data A catalogue record for this book is available from the British Library For information on all Elsevier publications visit our web site at store.elsevier.com Printed and bound in USA 13 14 15 16 17 10 ISBN: 978-0-12-407194-0 This book has been manufactured using Print On Demand technology Each copy is produced to order and is limited to black ink The online version of this book will show color Figures where appropriate About the Author Born Nov 22, 1928, in Lima, Peru; married May 24, 1958, in Galena, MD, Marcia D Craddock; three children, eight grandchildren Education: Gina´sio diploma, St Paul’s School, Sa˜o Paulo, Brazil, 1943; H S diploma, Sa˜o Paulo Graded School, 1945; B Sc (Chemistry and Mathematics), Acadia University, Wolfville, NS, Canada, 1950; Ph.D (Chemistry), McGill University, Montreal, PQ, Canada, 1954 Employment: Postdoctoral Fellow, National Research Council, Ottawa, Canada, 1954–1955; Research Chemist, Du Pont Experimental Station, Wilmington, DE, 1956–1959; Research Chemist, Research Center, Hooker Chemical Corp., Grand Island, NY, 1959–1966; Research Chemist, Southern Regional Research Center, U.S Department of Agriculture, New Orleans, LA, 1967–1990; Technical Editor, Gmelin Institute, Frankfurt-am-Main, Germany, 1990–1992 Publications Books: Frank, Arlen W., The Cotton Gazetteer, self-published, â 1985, xii ỵ 193 pp.; Frank, W A [sic], “Phosphonous Acids (Thio-, Seleno- Analogs) and Derivatives,” Chapter 10 in Kosolapoff, G M.; Maier, L “Organic Phosphorus Compounds,” Wiley-Interscience, New York, 1972, Vol (of 7), 531 pp Reviews: Frank, Arlen W., “The Phosphonous Acids and Their Derivatives,” Chem Rev 1961, 30(4), 389–424; Frank, Arlen W., “Synthesis and Properties of N-, O- and S- Phospho Derivatives of Amino Acids, Peptides, and Proteins,” Crit Rev Biochem Molec Biol 1984, 16(1), 51–101 Other Publications: About 50 articles and about 25 patents, mostly in the field of organophosphorus chemistry ix Preface This book had its inception in 1990 when I was beginning a 2-year tour of duty as a technical editor for the Gmelin Institute in Frankfurt am Main, Germany, one of the institutes of the Max Planck Society The multivolume GMELIN Handbook of Inorganic Chemistry series, published by Springer-Verlag since 1924, was published in German during its early years but increasingly in English in recent years Our task as editors was to render manuscripts written by authors not fully versed in the English language into a form suitable for publication The presence of the joint Gmelin/Beilstein Library onsite and the University of Frankfurt’s Senckenberg Library a short distance away prompted me to start work on a long-cherished dream—a comprehensive book on the chemistry of phosphorus compounds in plants—during periods of inactivity between editorial assignments Alas, the Handbook ceased publication in 1998 and the Gmelin Institute itself was closed in 1999, a victim of budget constraints following the merger of the former East German Science Institutes into the Max Planck Society in the early 1990s My original intent was to cover all types of phosphorus compounds found in plants, both organic and inorganic, but I soon realized that some measures would have to be taken to keep the book a manageable size The first to go were the nucleic acids RNA and DNA, despite their importance—they comprise, for example, 11.1% and 1.44%, respectively, of the total phosphorus in the duckweed Spirodela oligorrhiza (pp 442–443) Next to go were the inorganic phosphates—phosphoric acid (Pi), di- or pyrophosphoric acid (PPi), and the polyphosphoric acids—70.7%, 0.17%, and undetected,a respectively, in S oligorrhiza Phosphoric acid presents a problem because it is difficult (but not impossible) to distinguish Pi released during workup from Pi already present in the plant Last to go were the phosphoproteins because the information on them is too old and sparse to be relevant The coverage in this book is therefore restricted to monomeric phosphorus-containing compounds with the sole exception of the starch phosphates A substantial setback occurred on August 29, 2005 when hurricane Katrina, with a single violent surge of flood water, destroyed all of the reprints I had assembled over the years along with most of my notes Little did I know that this book would take 20 years to complete, but here it is at last, my magnum opus Slidell, LA, USA July 7, 2012 a The lower plants store phosphorus in the form of polyphosphates but the higher plants use phytic acid (Chapter 2) for this function.1 xi Acknowledgments I am grateful to the librarians and their staff of the Earl K Long Library at the University of New Orleans and the Howard-Tilton Library at Tulane University, New Orleans, where most of my research for this book was carried out; to the editors and staff of Elsevier, in particular to Mr Adrian Shell, Ph.D., Senior Acquisitions Editor, Oxford, UK, to Jessica Vaughan, Editorial Project Manager, Waltham, MA, and to my two Production Managers in Gurgaon, India,* Mr Hemachander Timiri Sundaram and his staff and Mr Mohana Priyan Rajendran and his staff, for carrying the project through to completion xiii Introduction Arlen W Frank This book is intended to be a reference source for scientists engaged in any aspect of plant research—chemistry, biochemistry, or physiology—with primary focus on the chemistry of phosphorus-containing compounds that occur naturally in the plant kingdom and specifically in the higher plants (Plantae) Algae, fungi, and other lower plant forms are not covered In general, the subject matter is treated in order of increasing complexity, compounds of C, H, and O in Chapters 1–3 and compounds of C, H, O, and N in Chapters 4–7 Chapter covers the various methods developed in early studies to determine the overall distribution of phosphorus-containing compounds in plants Appendix A covers the changes in phosphorus-containing compounds during germination and Appendix B their accumulation during growth and senescence The final sections of the book comprise a comprehensive list of references and a combined index of the plants and phosphorus compounds The Phosphorus Compounds Nomenclature The naming of the phosphorus compounds in this book conforms to the recommendations of the Drake Committee on the Nomenclature of Organic Phosphorus Compounds published in 1952.2 Chemical Abstracts followed closely these recommendations until the early 1970s but then began to move away from them toward the present system, which in effect subordinates P, O, N, and other atoms to C and indexes the compounds as derivatives of the organic compound having the longest carbon chain Thus, D-glyceraldehyde 3phosphate, formerly indexed as a derivative of D-glyceraldehyde, is now indexed as a derivative of propanal The rationale for doing this was to facilitate the searching and indexing of the chemical literature and was never intended to replace the IUC nomenclature: CHO IUC Name: D-Glyceraldehyde, 3-phosphate H OH CAS Name: Propanal, R-(2)-hydroxy-3-phosphonooxy)- CH2OP(O)(OH)2 The order of presentation for each compound in this book is as follows: (1) its IUC name; (2) its commonly used abbreviation in parentheses; (3) its molecular formula; Chemistry of Plant Phosphorus Compounds © 2013 Elsevier Inc All rights reserved xv xvi INTRODUCTION (4) its Beilstein reference if available; (5) its Chemical Abstracts name in italics; and (6) the year it was first reported to be a plant constituent Occurrence If the phosphorus compound is a common plant metabolite, as is often the case, its place in the metabolic sequence is illustrated by a figure The figures in this book are composites drawn from various sources, not reproductions from a single source, except for the few instances in which a reference is cited The shadowed boxes in the figures show metabolites inside the box and precursors and products outside the box The box itself does not represent a cell wall or other physical barrier If the phosphorus compound is unique for a particular plant species, which sometimes occurs owing to some metabolic quirk peculiar to that species, the original paper should be consulted for further details A few of the plant species in which a particular phosphorus compound was first mentioned are also cited under this heading, documenting the date given under (6) above Physical Properties The physical appearance and solubility characteristics of each compound are given if the information is available A few salts are included for each compound if useful for characterization but esters, amides, and other derivatives are not References to spectra, chromtography and electrophoresis are selective rather than comprehensive—usually a single citation selected from those that are available Synthesis A brief survey is given of the methods that have been used to prepare each compound in the laboratory The coverage is comprehensive with respect to the variety of methods but selective in the number of references cited, often just a single citation Hydrolysis The sensitivity of the compounds to cleavage of the phosphate group varies significantly from one compound to another Particular attention is given to hydrolysis under acid or alkaline conditions or in the presence of heavy metal catalysts Rate constants are given whenever possible Phosphorylation Studies under this heading are restricted to the phosphorylation of monophosphates to di-, tri-, or polyphosphates by means of known phosphorylating reagents Some enzymatic phosphorylations appear in the metabolic pathways discussed under the section “Occurrence” and some instances of the use of phosphorylating reagents to introduce a phosphate group elsewhere in the molecule appear under the section “Synthesis.” Introduction xvii Structure Studies under this heading are concerned with problems such as keto/enol tautomerism or pyranose/furanose conformation in phosphorylated sugars or preferred conformation in phytic acid Extraction No single extraction procedure is optimal for all phosphorus compounds Attention here is focused on the methods that are most suitable for a particular compound or class of compounds Methods that are generally applicable to a class of compounds are described in detail at the beginning of each chapter, with selected examples from the literature for methods that are widely accepted and in general use Separation and Analysis The same principles apply here Methods that are generally applicable to the separation and analysis of the individual phosphorus compounds present in an extract are described in detail at the beginning of each chapter Analysis Without Separation Two methods in particular fall under this heading: the 31P NMR method and the enzymatic method The first method provides a characteristic signal for each phosphorus compound, some of which are distinct enough to be useful for positive identification, and the second method may be specific enough to permit measurement of a particular phosphorus compound in a complex mixture Index of Compounds The phosphorus compounds are listed in the Index alphabetically according to their IUC names with cross-referencing to their CAS names and commonly used abbreviations The Plants Tables The plants are listed alphabetically in the various tables according to the binary scientific names adopted by the International Code of Botanical Nomenclature (ICBN) Their common English names are also given if known The measurements are presented in nmol/g as the preferred format unless stated otherwise xviii INTRODUCTION Index of Plants The plants are listed in the Index alphabetically according to their ICBN names with crossreferencing to their common names in English or other language that may be provided by the authors References In order to avoid duplication, all of the references are assembled in a single group near the end of the book Index 655 Perilla frutescens (Perilla Mint), 89t, 189t, 223t, 475–490 ssp japonica (Egoma), 475–490 Periwinkle See Vinca erecta; Vinca minor Periwinkle, Madagascar See Catharanthus roseus Persea americana (Avocado), 18t, 42t, 89t, 223t, 312t, 380t, 413t, 446t, 469t, 490–500 Persea gratissima (Avocado), 7t, 42t, 66t Persimmon See Diospyros discolor Persimmon, Japanese See Diospyros kaki Petroselinum crispum (Parsley), 89t, 212t, 223t, 380t, 392t, 413t, 458t, 475–490 Pe-Tsai See Brassica pekinensis Petunia hybrida (Garden Petunia), 89t, 212t, 223t, 475–500 Peucedanum graveolens See Anethum graveolens Peucedanum verticillare, 212t Peumus boldus (Boldo), 413t PG See Phosphatidylglycerol (PG) 6-PG See 6-Phosphogluconic Acid (6-PG) 2-PGA See 2-Phosphoglyceric Acid (2-PGA) 3-PGA See 3-Phosphoglyceric Acid (3-PGA) Phacelia tanacetifolia (Fiddleneck), 312t, 392t, 413t, 475–490 Phalaris canariensis (Canary Grass), 70t Phalsa See Grewia asiatica Pharbitis nil (Morning Glory), 223t, 312t, 413t, 446t Phaseolus acutifolius (Tepary Bean), 89t Phaseolus coccineus (Scarlet Runner Bean), 42t, 89t, 178t, 189t, 196t, 200t, 208t, 223t, 413t, 432t, 475–490 Phaseolus lunatus (Lima Bean), 70t, 89t, 152t, 223t, 455t, 475–490 Phaseolus vulgaris (Common Bean), 18t, 33t, 42t, 70t, 89t, 152t, 223t, 312t, 373, 380t, 392t, 413t, 432t, 455t, 462t, 475–490 ssp humilis (Bush Bean), 223t ssp napus (Dwarf Common Bean), 312t, 380t, 413t Phellodendron wilsonii (Amur Cork Tree), 312t, 475–490 Philonotis fontana, 223t Philydrella pygmaea, 223t Phlomis fruticosa (Shrubby Jerusalem Sage), 413t Phoenix dactylifera (Date Palm), 89t, 223t, 413t Phoenix sylvestris (Wild Date Palm, Khar-jur), 223t Phosphatides, 156, 460–461 Phosphatidic Acid (PA), 159, 160, 161t, 162–163, 164t, 165, 166, 166t, 167t, 170, 198–199, 220–222, 223t, 473t, 475–500 Phosphatidylcholine (PC), 159–160, 174–183, 178t, 475–500 Phosphatidylethanolamine (PE), 159–160, 160f, 186–193, 189t Phosphatidylglycerol (PG), 11, 41–53, 57, 62, 159–160, 161t, 162, 164t, 165, 166, 166t, 167t, 168–169, 168t, 170–171, 178t, 197, 198–205, 200t, 206, 223t, 473t, 475–500 Phosphatidylinositol (PI), 86, 135, 136, 140f, 141, 156, 157–158, 159–160, 161t, 164t, 165, 166, 166t, 167t, 168, 170–171, 172t, 198–199, 207–209, 208t, 210–212, 212t, 214–215, 223t, 473t, 475–500 Phosphatidylinositol Bisphosphate (PIP2), 156, 157–158, 159–160, 166, 207, 212t, 214–215, 216, 475–490 Phosphatidylinositol Phosphate (PIP), 156, 157–158, 159–160, 166, 207, 212t, 214–216, 475–490 Phosphatidylserine (PS), 159, 160, 164t, 165, 166, 167t, 168, 170, 198–199, 217–219, 223t, 473t, 475–500 Phosphocholine, 160 Phosphodextrin, 69 Phosphoenolpyruvic Acid (PEP), 2, 4t, 5, 6t, 9, 9f, 10–11, 13, 14, 16–17, 18t, 27, 61, 346–348, 349, 357, 360, 362, 380, 457–460, 473t, 475–500 Phosphoethanolamine, 160 6-Phosphogluconic Acid (6-PG), 1, 4t, 5–6, 6t, 30, 30f, 31, 35, 36–37, 36f, 38, 40, 41, 42t, 53, 57, 473t, 475–500 656 INDEX 2-Phosphoglyceric Acid (2-PGA), 1, 4t, 6t, 9, 10–11, 12, 14, 15–17, 18t, 27, 490–500 3-Phosphoglyceric Acid (3-PGA), 1, 2, 4t, 5, 6–7, 6t, 8–9, 9f, 10–11, 12, 13, 14, 15–17, 18t, 27, 34, 57, 475–500 Phospholipids (PL), 2, 159–304, 460, 471, 473t Phosphoproteins, 460 Phosphoric Acid (Pi), 2, 3, 4, 4t, 5, 8–9, 11, 14, 15, 16, 40–41, 56, 57, 59, 61–62, 63, 76, 84–86, 86t, 135, 142, 152t, 157, 168, 212t, 214, 217, 218t, 309t, 311, 354–355, 357, 358, 360, 362–363, 379, 380, 438, 453, 457–468, 458t, 462t, 469t, 471, 472, 472t, 473t, 475–500 Phosphorylserine, 473t PHPA See 1-Palmitoyl-sn-glycero-3(dihydrogen phosphate) (PHPA) PHPC See 1-Palmitoyl-sn-glycero-3phosphocholine (PHPC) PHPE See 1-Palmitoyl-sn-glycero-3-phospho10 -ethanolamine (PHPE) PHPG See 1-Palmitoyl-sn-glycero-3-phosphosn-10 -glycerol (PHPG) PHPI See 1-Palmitoyl-sn-glycero-3-phosphoD-myo-inositol (PHPI) PHPS See 1-Palmitoyl-sn-glycero-3-phosphoL-serine (PHPS) Phragmites australis, 312t Phragmites communis (Water Reed), 18t, 33t, 223t Phyllitis scolopendrium (Hart’s Tongue Fern), 223t Phyllocactus spp., 413t Phellodendron wilsonii, 312t, 475–490 Phylloglossum drummondii, 89t Phyllospadix iwatensis, 223t Phyllostachys bambusoides (Timber Bamboo), 312t Phyllostachys nigra (Black Bamboo), 312t Phyllostachys pubescens (Moso Bamboo), 223t, 312t, 392t, 413t Physalis ixocarpa (Tomatillo), 89t Physalis peruviana (Cape Gooseberry), 89t Phytic Acid (InsP6), 1, 75–134, 135–136, 136t, 137–138, 137t, 141, 143f, 145f, 147, 147f, 149, 151, 152t, 162–163, 457–461, 471, 472t, 473t, 475–500 Phytin, 75, 79, 82, 86t, 87–88 Phytoglycolipid, 475–490 Pi See Phosphoric Acid (Pi) Picea abies (Norway Spruce), 18t, 42t, 178t, 189t, 223t, 312t, 413t, 446t, 475–500 Picea glauca (White Spruce), 89t Picea mariana (Black Spruce), 89t, 223t, 462t, 490–500 Picea pungens (Colorado Spruce), 89t, 475–490 Picea spp (Spruce), 89t Pimpinella anisum, 223t Pinusmugo (Mugo Pine) ssp mughus, 89t ssp rostrata, 89t PIP See Phosphatidylinositol Phosphate (PIP) PIP2 See Phosphatidylinositol Bisphosphate (PIP2) Piper clusii (African Cubeb), 89t Piper guineense (Guinea Cubeb, Etinkane), 89t Piper nigrum (Black Pepper), 89t Pisonia alba (Lettuce Tree), 89t Pistacia atlantica (Mt Atlas Mastic Tree), 89t Pistacia mutica (Mt Atlas Mastic Tree), 312t Pistia stratiotes (Water Lettuce), 223t Pisum sativum (Pea), 6–7, 7t, 18t, 33t, 42t, 66t, 68t, 70t, 78t, 89t, 139t, 152t, 158t, 178t, 189t, 196t, 200t, 208t, 212t, 223t, 312t, 380t, 392t, 413t, 432t, 446t, 455t, 462t, 469t, 472t, 475500 Pithecellobium dulce (Manila Tamarind, Korukapalli), 89t ă bano), 89t Pithecellobium flexicaule (E PL See Phospholipids (PL) Plagiomnium ellipticum, 223t Plagiomnium medium, 223t Plane Tree See Platanus spp Plantago lanceolata (Narrowleaf Plantain), 413t Plantain See Musa  paradisiaca Plantain, Narroleaf See Plantago lanceolata Plantain, Water See Alisma orientale Index 657 Platanus occidentalis (Eastern Sycamore), 312t, 446t Platanus spp (Plane Tree), 223t, 490–500 Platycerium alcicorne, 223t, 413t Pleurozium schreberi, 223t PLnPA See 1-Palmitoyl-2-linolenoyl-snglycero-3-(dihydrogen phosphate) (PLnPA) PLnPC See 1-Palmitoyl-2-linolenoyl-snglycero-3-phosphocholine (PLnPC) PLnPE See 1-Palmitoyl-2-linolenoyl-snglycero-3-phospho-10 -ethanolamine (PLnPE) PLnPG See 1-Palmitoyl-2-linolenoyl-snglycero-3-phospho-10 -sn-glycerol (PLnPG) PLnPI See 1-Palmitoyl-2-linolenoyl-snglycero-3-phospho-D-myo-inositol (PLnPI) PLP See Pyridoxal 50 -Phosphate (PLP) PLPA See 1-Palmitoyl-2-linoleoyl-sn-glycero3-(dihydrogen phosphate) (PLPA) PLPC See 1-Palmitoyl-2-linoleoyl-sn-glycero3-phosphocholine (PLPC) PLPE See 1-Palmitoyl-2-linoleoyl-sn-glycero3-phospho-10 -ethanolamine (PLPE) PLPG See 1-Palmitoyl-2-linoleoyl-sn-glycero3-phospho-10 sn-glycerol (PLPG) PLPI See 1-Palmitoyl-2-linoleoyl-sn-glycero3-phospho-D-myo-inositol (PLPI) PLPS See 1-Palmitoyl-2-linoleoyl-sn-glycero3-phospho-L-serine (PLPS) Plum See Prunus domestica PMP See Pyridoxamine 50 -Phosphate (PMP) PNP See Pyridoxine 50 -Phosphate (PNP) Poa annua (Annual Bluegrass), 81, 89t, 223t, 312t, 469t Poa pratensis (Kentucky Bluegrass), 223t Podocarp, Cloud See Podocarpus nubigenus Podocarpus macrophyllus (Yew Plum Pine), 312t, 475–490 Podocarpus nivalis (Snow Totara), 223t Podocarpus nubigenus (Manio, Cloud Podo-carp), 223t Podocarpus salignus (Willow Podocarp), 223t Podocarp, Willow See Podocarpus salignus Poinciana, Royal See Delonix regia Polygonum amphibium (Water Smartweed), 223t Polypodium vulgare (European Polypody), 223t Polypody See Polypodium vulgare Polystichum spp., 7t Polytrichum commune (Polytrichum Moss), 223t, 413t Polytrichum juniperinum (Hair Cap Moss), 223t Pomegranate See Punica granatum Pomelo See Citrus paradisi Poncirus trifoliata  Citrus paradisi (Citrumelo), 223t Pondweed, Flatstem See Potamogeton zosteriformis Pondweed, Floating Leaf See Potamogeton natans Pondweed, Perfoliate See Potamogeton perfoliatus Pongamia glabra (Pongam, Karanja), 223t POPA See 1-Palmitoyl-2-oleoyl-sn-glycero-3(dihydrogen phosphate) (POPA) POPC See 1-Palmitoyl-2-oleoyl-sn-glycero-3phosphocholine (POPC) POPE See 1-Palmitoyl-2-oleoyl-sn-glycero-3phospho-10 -ethanolamine (POPE) POPG See 1-Palmitoyl-2-oleoyl-sn-glycero-3phospho-10 -sn-glycerol (POPG) POPI See 1-Palmitoyl-2-oleoyl-sn-glycero-3phospho-D-myo-inositol (POPI) Poplar, Black See Populus nigra Poplar, Carolina See Populus euramericana Poplar, Lombardy See Populus nigra, var italica Poppy, California See Escholtzia californica Poppy, Corn See Papaver rhoeas Poppy, Field See Papaver dubium Poppy, Opium See Papaver somniferum Poppy, Oriental See Papaver orientale Poppy, Roemer See Roemeria refracta Poppy, Sea See Glaucium fimbrilligerum POPS See 1-Palmitoyl-2-oleoyl-sn-glycero-3phospho-L-serine (POPS) 658 INDEX Populus deltoides (Eastern Cottonwood), 18t, 42t, 392t ssp caudina, 413t Populus euroamericana (Carolina Poplar), 223t ssp gelrica, 223t Populus nigra (Black Poplar), 18t, 29t, 33t, 42t, 66t, 413t, 490–500 var italica (Lombardy Poplar), 223t Populus tremula (European Aspen), 42t, 413t Porphyra tenera (Nori), 432t Portulaca grandiflora (Rose Moss), 18t, 223t, 312t, 432t, 490–500 Portulaca oleracea (Purslane), 89t, 223t, 490–500 Posidonia oceanica (Mediterranean Tapeweed), 223t Potamogeton filiformis, 223t Potamogeton natans (Floating Leaf Pondweed), 223t Potamogeton perfoliatus (Perfoliate Pondweed), 223t Potamogeton zosteriformis (Flatstem Pondweed), 380t Potato See Solanum tuberosum Potato, Air See Dioscorea bulbifera Potato, Sweet See Ipomoea batatas Potato, Telingo See Amorphophallus campanulatus Potato, Wild See Solanum acaule; Solanum schreiteri Potentilla asiatica (Cinquefoil), 89t, 223t Poterium polygamum, 89t P(3t)PG See 1-Palmitoyl-2-trans-3hexadecenoyl-sn-glycero-3-phospho10 -sn-glycerol (P(3t)PG) PPi See Di-(or Pyro)phosphoric Acid (PPi) Premna odorata (Premna), 89t Prince’s Feather See Amaranthus hypochondriacus Pringlea antiscorbutica (Kerguelen Cabbage), 223t Prosopis africana, 89t Prosopis chilensis (Algarrobo), 89t Prosopis glandulosa (Honey Mesquite), 89t Prosopis velutina (Velvet Mesquite), 88, 89t Protea compacta, 89t Prunus armeniaca (Apricot), 18t, 37, 42t, 63t, 89t, 413t, 446t, 490–500 Prunus avium (Sweet Cherry), 89t, 223t, 490–500 Prunus bucharica, 89t Prunus cerasus (Morello Cherry), 223t, 413t Prunus domestica (Plum), 89t, 223t Prunus dulcis (Almond), 89t, 223t, 413t, 446t, 475–490 Prunus laurocerasus (Cherry Laurel), 89t Prunus mahaleb (Mahaleb Cherry), 89t Prunus mume (Japanese or Ume Apricot), 223t, 490–500 Prunus padus (Bird Cherry), 312t Prunus persica (Peach), 89t, 223t, 312t, 413t, 475–500 ssp nectarina (Nectarine), 312t Prunus petunnikowii, 89t Prunus sargentii (Sargent Cherry), 312t PS See Phosphatidylserine (PS) Pseudobryum cinclidioides, 223t Pseudosasa japonica (Arrow Bamboo), 446t Pseudotsuga menziesii (Douglas Fir), 446t Psidium guajava (Guava), 89t Psilotum triquetrum, 223t Psophocarpus tetragonolobus (Winged Bean), 89t, 223t, 475–490 Psoralea drupacea (Drupe Scurf Pea), 89t, 223t Pteridium aquilinum (Bracken Fern), 223t, 312t, 392t Pterocarpus mildbraedii (Mkpa), 89t Pterocarpus osun (African Padauk), 89t Pueraria hirsuta (Kudzu), 70t Pummelo See Citrus grandis Pumpkin See Cucurbita pepo Pumpkin, Fluted See Telfairia occidentalis Punica granatum (Pomegranate), 89t, 223t Purslane See Portulaca oleracea Purslane, Sea See Sesuvium portulacastrum Pyinkado, Burma See Xylia xylocarpa Pyridoxal 50 -Phosphate (PLP), 450–451, 452, 453, 454–455, 455t, 475–500 Pyridoxamine 50 -Phosphate (PMP), 450–451, 451f, 452, 453, 455t, 475–490 Index 659 Pyridoxine 50 -Phosphate (PNP), 451, 450–451, 451f, 452, 453, 455, 455t Pyrus communis (Pear), 18t, 33t, 42t, 66t, 223t, 312t, 413t, 446t, 490–500 Pyrus pyrifolia ssp culta (Nashi), 223t Pyrus serotina (Japanese Pear), 413t Q Quandong See Santalum acuminatum Queen Anne’s Lace See Daucus carota, ssp carota Quercus borealis (Red Oak), 34–35, 312t Quercus lusitanica (Portuguese Oak), 89t Quercus mongolica ssp grosseserrata, 312t Quercus palustris (Pin Oak), 223t Quercus petraea (Durmast Oak), 312t Quercus phellos (Willow Oak), 312t Quercus robur (English Oak), 89t, 223t, 312t Quercus rubra (Northern Red Oak), 18t, 33t, 42t Quercus spp (Oak), 89t Quince See Cydonia oblonga Quince, Japanese See Chaenomeles japonica Quinoa See Chenopodium quinoa R Radish See Raphanus sativus Radish, Japanese See Raphanus acanthiformis Ragi See Eleusine coracana Rain Tree See Samanea saman Rain Tree, Golden See Koelreuteria paniculata Ramonda nathaliae, 223t Ramonda serbica, 223t Ranunculus glacialis (Glacier Buttercup), 223t Ranunculus spp (Buttercup), 89t Rape See Brassica napus Rape, Oilseed See Brassica oleracea Rape, Turnip See Brassica campestris; Brassica rapa Rape, White Turnip See Brassica rapa, ssp rapa Rape, Winter See Brassica napus, ssp oleifera Raphanus acanthiformis (Japanese Radish), 200t, 312t Raphanus sativus (Radish), 18t, 33t, 42t, 70t, 89t, 178t, 189t, 200t, 223t, 312t, 380t, 413t, 432t, 446t, 475–500 ssp radicola (Radish), 223t Raphia farinifera (Raffia Palm), 223t Raphia hookeri (Ivory Coast Raffia Palm), 223t Raphia regalis, 223t Raphia sudanica, 223t Raphia vinifera (Wine Palm), 223t Rattleweed See Crotalaria retusa Ratu See Cassia sieberiana Rauvolfia serpentina (Indian Snakeroot), 178t, 189t, 208t, 223t Rauvolfia vomitoria (Swizzlestick), 89t Redwood, Dawn See Metasequoia glyptostroboides Reseda lutea (Yellow Mignonette), 413t RF See Riboflavin Rhamnose-1-Phosphate (Rha1P), 387–388 Rha1P See Rhamnose-1-Phosphate (Rha1P) Rhaponticum integrifolium, 89t, 223t Rhododendron ponticum (Common Rhododendron), 18t, 42t Rhododendron spp., 223t Rhodomyrtus tomentosa (Downy Myrtle), 89t Rhus hirta (Staghorn Sumac), 89t Ribes nigrum (Black Currant), 223t Ribes sinanense, 312t Riboflavin (RF), 405, 429–438, 430f, 432t, 439 Ribonucleic acid (RNA), 305–306, 307–308, 312t, 349, 350, 460, 472, 473t Ribose 5-Phosphate (R5P), 1, 4t, 6t, 10, 11, 14, 29–30, 30f, 31–32, 33t, 34–35, 63, 64–65, 354, 406–407, 490–500 Ribulose 1,5-Bisphosphate (Ru1,5P), 1, 4t, 6–7, 6f, 6t, 8–9, 9f, 10, 29–30, 30f, 31, 32, 33t, 34–35, 490–500 Ribulose 5-Phosphate (Ru5P), 1, 6t, 11, 29–30, 30f, 31, 32, 33t, 34–35, 36–37, 53, 430 Riccia fluitans (Crystalwort), 223t Rice See Oryza sativa Ricinus communis (Castor Bean), 18t, 42t, 68t, 89t, 200t, 223t, 312t, 392t, 413t, 462t, 475–500 Rimas See Artocarpus altilis RNA See Ribonucleic Acid 660 INDEX Robinia pseudoacacia (Black Locust), 66t, 223t, 312t, 380t, 413t, 432t, 490–500 Rocket Salad See Eruca sativa Rockrose See Cistus ladanifer Roemeria refracta (Roemer Poppy), 89t, 223t Ronji See Vigna auriculata Rorippa amphibia (Amphibious Marsh Cress), 223t Rosa canina (Dog Rose), 89t, 223t Rosa damascena (Damask Rose), 312t, 412, 413t Rosa rubiginosa (Sweetbrier Rose), 89t Rosa rugosa (Turkestan Rose), 223t Roselle See Hibiscus sabdariffa Rose Moss See Portulaca grandiflora Rowan See Sorbus aucuparia R5P See Ribose 5-Phosphate (R5P) Rubber Tree, Para´ See Hevea brasiliensis Rubia tinctorum (Madder), 89t Rubus spp (Blackberry), 89t, 223t Rue See Ruta graveolens Rue, African See Peganum harmala Rumex acetosa (Sorrel), 89t, 223t Rumex halaczii, 89t Rumex vesicarius (Chukai Shak), 89t Ru1,5P See Ribulose 1,5-Bisphosphate Ru5P See Ribulose 5-Phosphate Rush, Needlegrass See Juncus roemerianus Rutabaga See Brassica napobrassica Ruta graveolens (Rue), 223t Rye See Secale cereale Ryegrass, Italian See Lolium multiflorum Ryegrass, Perennial See Lolium perenne Ryegrass, Poison See Lolium cuneatum S Saccharum officinarum (Sugarcane), 4t, 18t, 42t, 223t, 312t, 392t, 413t, 469t Saccharum sinense, 18t Saccharum spp., 42t, 212t Safflower See Carthamus tinctorius Safflower, Wild See Carthamus oxycantha Sagargota See Caesalpinia bonducella Sage See Salvia macrosiphon Sage, Shrubby Jerusalem See Phlomis fruticosa Sage, Yellow See Lantana camara, ssp aculeata Sagittaria sagittifolia (Arrowhead), 223t, 446t Sagittaria trifolia (Chinese Arrowhead), 70t Salicornia arabica, 223t Salicornia europaea (Samphire), 223t Salix alba (White Willow), 312t, 413t Salix babylonica (Weeping Willow), 312t Salix cinerea (Large Gray Willow), 413t Salix daphnoides, 312t Salix fragilis (Crack Willow), 413t Salix herbacea (Dwarf Willow), 223t Salix matsudana ssp tortuosa (Dragon-Claw Willow), 312t Salix nigricans (Dark-Leaved Willow), 413t Salix reticulata (Netleaf Willow), 223t Salix retusa (Notchleaf Willow), 223t Salix triandra (Almond Willow), 18t, 42t, 312t, 392t, 469t Salix viminalis (Basket Willow), 312t, 413t Salsola gemmascens, 462t, 490–500 Salsola sclerantha, 462t, 490–500 Saltgrass, Coastal See Distichlis spicata Salvadora oleoides (Khakan), 223t Salvation Jane See Echium plantagineum Salvia macrosiphon (Sage), 89t Salvinia nutans, 223t Samanea saman (Rain Tree), 140, 143, 145, 152t, 212t Sambucus nigra (European Elder), 223t, 432t Sambucus sieboldiana ssp miquelii, 312t Samphire See Salicornia europaea Sandoricum koetjape (Santol), 89t Santalum acuminatum (Quandong), 89t Santol See Sandoricum koetjape Sapium sebiferum (Vegetable Tallow Tree), 223t Saponaria vaccaria (Cow Cockle), 223t, 312t Saposhnikovium spp., 89t Sarson, Yellow See Brassica campestris, ssp sarson Sauromatum guttatum (Voodoo Lily), 312t Saussuria depressa, 223t Saxegothaea conspicua (Prince Albert Yew), 223t Scallion See Allium ascalonicum Index 661 Scilla hispanica (Spanish Bluebell), 413t Scirpus holoschoemus (Roundhead Bulrush), 413t Scirpus subterminalis, 380t Scouring Bush, Dwarf See Equisetum scirpoides Seablite See Suaeda maritima Seablite, Annual See Suaeda maritima, var macrocarpa Sea Purse See Dioclea reflexa Seaweed, 432t, 455t Seaweed, Brown See Laminaria japonica Seawrack See Zostera marina Secale cereale (Rye), 33t, 42t, 70t, 89t, 152t, 178t, 189t, 200t, 208t, 223t, 312t, 380t, 413t, 432t, 455t, 458t, 462t, 475–500 Sedoheptulose 1,7-Bisphosphate (Se1,7P), 1, 6t, 10, 28, 62, 63, 64–65, 66t Sedoheptulose 7-Phosphate (Se7P), 1, 4t, 6t, 10, 11, 28, 29, 30, 54, 62, 63, 64–65, 66t, 473t, 490–500 Seepweed, Alkali See Suaeda fruticosa Selaginella denticulata (Toothleaved Clubmoss), 392t, 413t, 469t Selaginella kraussiana, 223t Selaginella pallescens (Moss Fern), 223t Selaginella selaginoides (Club Spikemoss), 223t Selaginella uncinata (Blue Spiemoss), 223t Selaginella willdenowii, 223t Senecio cruentus (Cineraria), 89t Senecio vulgaris (Groundsel), 223t Senna, Coffee See Cassia occidentalis Senna, Pig’s See Cassia absus Senna septentrionalis (Arsenic Bush), 223t Se1,7P See Sedoheptulose 1,7-Bisphosphate (Se1,7P) Se7P See Sedoheptulose 7-Phosphate (Se7P) Sequoiadendron giganteum (Giant Sequoia), 223t, 312t Serendipity Berry See Dioscoreophyllum cumminsii Sesamum alatum, 18t, 42t Sesamum indicum (Sesame), 42t, 89t, 223t, 413t, 462t, 475–500 Sesbania grandiflora (Scarlet Wistaria Tree, Agati), 89t Sesuvium portulacastrum (Sea Purslane), 89t Setaria glauca (Yellow Foxtail), 223t Setaria italica (Italian or Foxtail Millet), 89t, 223t Setaria verticillata (Bristly Foxtail), 223t, 413t Shallot See Allium ascalonicum Shameplant See Mimosa pudica Shea Butter Tree See Butyrospermum paradoxum She Oak, Black See Casuarina littoralis She Oak, Slaty See Casuarina muelleriana Shepherd’s Purse See Capsella bursapastoris Shield Fern See Dryopteris filix-mas SHPA See 1-Stearoyl-sn-glycero-3(dihydrogen phosphate) (SHPA) SHPC See 1-Stearoyl-sn-glycero-3phosphocholine (SHPC) SHPE See 1-Stearoyl-sn-glycero-3-phospho10 -ethanolamine (SHPE) SHPG See 1-Stearoyl-sn-glycero-3-phosphosn-glycerol (SHPG) SHPS See 1-Stearoyl-sn-glycero-3-phospho-Lserine (SHPS) Sicklepod See Cassia tora Sicyos angulatus (Bur Cucumber), 223t Simmondsia chinensis (Jojoba), 89t, 223t Sinapis alba (White Mustard), 89t, 312t, 380t, 392t, 413t, 469t, 475–490 Sisal See Agave sisalana Siseles See Alternanthera sessilis Sison amomum (Stone Parsley), 223t SLnPC See 1-Stearoyl-2-linolenoyl-sn-glycero3-phosphocholine (SLnPC) SLnPE See 1-Stearoyl-2-linolenoyl-sn-glycero3-phospho-10 -ethanolamine (SLnPE) SLnPG See 1-Stearoyl-2-linolenoyl-sn-glycero3-phospho-10 -sn-glycerol (SLnPG) SLnPI See 1-Stearoyl-2-linolenoyl-sn-glycero3-phospho-D-myo-Inositol (SLnPI) SLPA See 1-Stearoyl-2-linoleoyl-sn-glycero-3(dihydrogen phosphate) (SLPA) SLPC See 1-Stearoyl-2-linoleoyl-sn-glycero-3phosphocholine (SLPC) 662 INDEX SLPE See 1-Stearoyl-2-linoleoyl-sn-glycero-3phospho-10 -ethanolamine (SLPE) SLPG See 1-Stearoyl-2-linoleoyl-sn-glycero-3phospho-10 -sn-glycerol (SLPG) SLPI See 1-Stearoyl-2-linoleoyl-sn-glycero-3phospho-D-myo-Inositol (SLPI) SLPS See 1-Stearoyl-2-linoleoyl-sn-glycero-3phospho-L-serine (SLPS) Smartweed, Water See Polygonum amphibium Smilax spp (Greenbrier), 223t Snakeroot, Indian See Rauvolfia serpentina Snapdragon See Antirrhinum majus SODPG See 10 ,30 -bis(1-Stearoyl-2-oleoyl-snglycero-3-phospho)-10 -sn-glycerol (SODPG) Solanum acaule (Wild Potato), 223t, 490–500 ssp depexum, 223t ssp punae, 223t, 490–500 ssp schreiteri, 223t, 490–500 Solanum africanum, 89t Solanum argentinum, 223t Solanum commersonii (Commerson’s Nightshade), 223t Solanum demissum (Nightshade), 223t, 490–500 Solanum gnomalum, 89t Solanum maglia, 223t, 490–500 Solanum mauritianum (Earleaf Nightshade), 89t Solanum melongena (Eggplant, Brinjal), 89t, 212t, 223t, 312t Solanum nigrum (Black Nightshade), 89t Solanum pamitanae, 223t, 490–500 Solanum phureja (Nightshade), 70t Solanum rybinii, 223t, 490–500 Solanum sanctaerosae, 223t, 490–500 Solanum schreiteri (Wild Potato), 223t Solanum tuberosum (Potato), 2, 4–5, 18t, 33t, 451, 39, 41, 42t, 54, 58, 63t, 69, 70t, 81, 89t, 178t, 189t, 208t, 223t, 311, 312t, 380t, 392t, 406, 412, 413t, 429, 432t, 446t, 455t, 458t, 462t, 469t, 471, 472t, 475–500 Sonneratia alba, 380t So1P See Sorbitol 1-Phosphate (So1P) So6P See Sorbitol 6-Phosphate (So6P) SOPA See 1-Stearoyl-2-oleoyl-sn-glycero-3(dihydrogen phosphate) (SOPA) SOPC See 1-Stearoyl-2-oleoyl-sn-glycero-3phosphocholine (SOPC) SOPE See 1-Stearoyl-2-oleoyl-sn-glycero-3phospho-10 -ethanolamine (SOPE) SOPG See 1-Stearoyl-2-oleoyl-sn-glycero-3phospho-10 -sn-glycerol (SOPG) Sophora japonica (Japanese Pagoda Tree), 89t, 223t, 475–490 SOPI See 1-Stearoyl-2-oleoyl-sn-glycero-3phospho-D-myo-Inositol (SOPI) SOPS See 1-Stearoyl-2-oleoyl-sn-glycero-3phospho-L-serine (SOPS) Sorbitol 1-Phosphate (So1P), 1, 35, 36, 37, 38, 39, 41 Sorbitol 6-Phosphate (So6P), 1, 35, 36, 37, 39, 40, 41 Sorbus aucuparia (Rowan), 5, 223t, 346 Sorbus commixta (Mountain Ash), 312t Sorghum bicolor (Sorghum), 7t, 18t, 42t, 70t, 89t, 152t, 223t, 310–311, 312t, 392t, 413t, 462t, 472t, 475–500 var cernuum (White Durra), 223t Sorghum halepense (Johnson Grass), 89t Sorghum sudanense, 312t Sorrel See Rumex acetosa Soursop See Annona muricata Soybean See Glycine max; Glycine soja Spartina alterniflora (Smooth Cordgrass), 18t, 312t, 490–500 Spartina cynosuroides, 490–500 Spartina patens (Saltmeadow Cordgrass), 223t, 312t, 490–500 Spatterdock See Nuphar advena Spearmint See Mentha spicata Spelt See Triticum spelta S(3t)PG See 1-Stearoyl-2-trans-3hexadecenoyl-sn-glycero-3-phospho10 -sn-glycerol (S(3t)PG) Sphagnum nemorium, 223t Sphagnum palustre (Prairie Sphagnum), 223t Sphagnum squarrosum (Sphagnum), 223t Sphenostylis stenocarpa (African Yambean), 89t Index 663 Spiderlily, Red See Lycoris radiata Spider Plant See Chlorophytum comosum Spikemoss, Blue See Selaginella uncinata Spikemoss, Club See Selaginella selaginoides Spinach See Spinacia oleracea Spinach, New Zealand See Tetragonia expansa Spinach, Philippine See Talinum triangulare Spinacia oleracea (Spinach), 7t, 18t, 33t, 42t, 65, 66t, 68t, 89t, 161t, 178t, 223t, 312t, 392t, 413t, 432t, 446t, 469t, 472t Spinacia turkestanica, 89t Spindle Tree, European See Euonymus europaeus Spindle Tree, Japanese See Euonymus japonica Spirodela oligorrhiza (Duckweed), 18t, 42t, 59, 63t, 68t, 223t, 380t, 392t, 457, 462t, 469t, 472, 473t Spirodela polyrrhiza (Giant Duckweed), 89t, 140, 143, 145, 148, 150, 152t, 156, 158t, 212t, 215, 223t, 413t Spleenwort, Green See Asplenium viride Spondias mombin (Yellow Mombin), 89t Spondias purpurea (Red Mombin), 89t SPPG See 1-Stearoyl-2-palmitoyl-sn-glycero3-phospho-10 -sn-glycerol (SPPG) Spruce See Picea spp Spruce, Black See Picea mariana Spruce, Colorado See Picea pungens Spruce, Norway See Picea abies Spruce, White See Picea glauca Spurge, Caper See Euphorbia lathyris Squash See Cucurbita digitata; Cucurbita palmata Squash, Hubbard See Cucurbita maxima Squash, Warty See Cucurbita moschata Squash, Winter See Cucurbita andreana Squash, Zucchini See Cucurbita pepo, ssp melopepo Stachys officinalis (Common Hedgenettle), 413t Starapple, African See Chrysophyllum albidum Starch phosphate, 68–69 1-Stearoyl-2-linolenoyl-sn-glycero-3phosphocholine (SLnPC), 175, 177 1-Stearoyl-2-linolenoyl-sn-glycero-3phospho-D-myo-inositol (SLnPI), 211 1-Stearoyl-2-linolenoyl-sn-glycero-3phospho-10 -ethanolamine (SLnPE), 187, 192 1-Stearoyl-2-linolenoyl-sn-glycero-3phospho-10 -sn-glycerol (SLnPG), 200t 1-Stearoyl-2-linoleoyl-sn-glycero-3(dihydrogen phosphate) (SLPA), 221 1-Stearoyl-2-linoleoyl-sn-glycero-3phosphocholine (SLPC), 175, 177 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphoD-myo-inositol (SLPI), 210 1-Stearoyl-2-linoleoyl-sn-glycero-3-phospho10 -ethanolamine (SLPE), 187, 192 1-Stearoyl-2-linoleoyl-sn-glycero-3-phosphoL-serine (SLPS), 218 1-Stearoyl-2-linoleoyl-sn-glycero-3-phospho10 -sn-glycerol (SLPG), 200t 1-Stearoyl-2-oleoyl-sn-glycero-3-(dihydrogen phosphate) (SOPA), 207, 221 1-Stearoyl-2-oleoyl-sn-glycero-3phosphocholine (SOPC), 175, 177 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-Dmyo-inositol (SOPI), 210, 211–212 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-10 ethanolamine (SOPE), 187, 192 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-Lserine (SOPS), 217, 218 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-10 sn-glycerol (SOPG), 200t 1-Stearoyl-2-palmitoyl-sn-glycero-3-phospho10 -sn-glycerol (SPPG), 199 1-Stearoyl-sn-glycero-3-(dihydrogen phosphate) (SHPA), 185, 222 2-Stearoyl-sn-glycero-3-(dihydrogen phosphate) (HSPA), 222 1-Stearoyl-sn-glycero-3-phosphocholine (SHPC), 177, 183, 184, 185, 222 1-Stearoyl-sn-glycero-3-phospho-10 ethanolamine (SHPE), 193, 194 1-Stearoyl-sn-glycero-3-phospho-L-serine (SHPS), 219 1-Stearoyl-sn-glycero-3-phospho-sn-glycerol (SHPG), 205, 206 664 INDEX 1-Stearoyl-2-trans-3-hexadecenoyl-snglycero-3-phospho-10 -sn-glycerol (S(3t)PG), 199 Stellaria media (Chickweed), 413t, 432t Sterculia foetida (Indian Almond, Jangli Badam), 89t, 223t Stillingia spp (Toothleaf ), 89t Stizolobium aterrimum (Bengal Bean), 89t Strawberry See Fragaria spp Strawberry Tree See Arbutus unedo Strawberry, Woodland See Fragaria vesca Strelitzia reginae (Bird of Paradise), 89t Striga asiatica (Witchweed), 223t, 475–490 Striga aspera, 223t Striga hermonthica (Purple Witchweed), 223t Strophanthus hispidus, 413t Stylidium petiolare, 89t Suaeda fruticosa (Alkali Seepweed), 223t Suaeda maritima (Seablite) var macrocarpa (Annual Seablite), 223t Suaeda maritima (Seablite), 223t Sucrose 60 -Phosphate, 67–68, 68t Sudachi See Citrus sudachi Sugarcane See Saccharum officinarum Sugar nucleotides, 305, 387–404, 388f, 392t Sugar phosphates, 1–73, 80, 86, 308–309, 468, 471, 473t Sultana See Impatiens sultanii Sultan, Sweer See Centaurea moschata Sumac, Chinese See Ailanthus glandulosa Sumac, Staghorn See Rhus hirta Sunflower See Helianthus annuus Sunnhemp See Crotalaria juncea Sweetsop See Annona squamosa Swietenia mahogani (West Indian Maho-gany), 223t Swizzlestick See Rauvolfia vomitoria Sycamore, Eastern See Platanus occidentalis T Talinum triangulare (Philippine Spinach, Fameflower), 89t Tallow Tree, Vegetable See Sapium sebiferum Tamarack See Larix laricina Tamarind See Tamarindus indica Tamarind, Manila See Pithecellobium dulce Tamarindus indica (Tamarind, Tsamiya), 89t, 223t Tampala See Amaranthus tricolor Tangelo See Citrus paradisi x Citrus reticulata Tangerine See Citrus reticulata Tangor See Citrus nobilis Tannia See Xanthosoma sagittifolium Tapeweed, Mediterranean See Posidonia oceanica Tapinanthus dodoneifolius (African Mistle-toe), 223t Taramira See Eruca sativa Tara Vine See Actinidia arguta Taraxacum spp (Dandelion), 200t Taro See Colocasia esculenta Taro, Asian See Alocasia odora Taro, Egyptian See Colocasia antiquorum Taro, Giant See Alocasia macrorrhiza Tarwi See Lupinus mutabilis Tasselflower, Red See Emilia sonchifolia Taxus baccata (English Yew), 223t Taxus cuspidata (Japanese Yew), 223t TDP See Thiamine Diphosphate (TDP); Thymidine 50 -Diphosphate (TDP) TDPGalA See Thymidine 50 -Diphosphate Galacturonic Acid (TDPGalA) TDPGlc See Thymidine 50 -Diphosphate Glucose (TDPGlc) Tea See Camellia sinensis; Thea sinensis Tea, Assam See Camellia sinensis, ssp assamica Teasel See Dipsacus fullonum, var sylvestris Telfairia occidentalis (Fluted Pumpkin), 89t Tenweeks Stock See Matthiola incana Terminalia catappa (Indian Almond), 89t Tetracarpidium conophorum (Conophor), 89t Tetragonia expansa (New Zealand Spinach), 223t Tetrapleura tetraptera, 89t Tetrastigma harmandii (Ayo), 89t Tetrose Phosphates, 28–29, 28f, 29t Thalassia testudinum (Turtle Grass), 312t Thea sinensis (Tea), 413t Theobroma cacao (Cocoa), 89t, 152t, 223t Index 665 Thevetia neriifolia (Yellow Oleander, Pivala Kanher), 223t Thiamine Diphosphate (TDP), 440 Thiamine Monophosphate (TMP), 439, 440 Thiamine Triphosphate (TTP), 439, 441 Thistle, Black See Carduus acanthoides Thistle, Curly Plumeless See Carduus crispus Thistle, Scotch See Onopordon acanthium Thistle, Star See Centaurea calcitrapa Thistle, Yellow Star See Centaurea solstitialis Thorn Apple See Datura spp Thorn Apple, Downy See Datura inoxia Thorn, Box See Lycium chinense Thuidium tamariscinum (Tamarisk Thu-idium Moss), 223t Thymidine 50 -Diphosphate (TDP), 371 Thymidine 50 -Diphosphate Galacturonic Acid (TDPGalA), 392t Thymidine 50 -Diphosphate Glucose (TDPGlc), 387–388, 392t Thymidine 50 -Phosphate (TMP), 370 Thymidine 50 -Triphosphate (TTP), 371 50 -Thymidylic acid See Thymidine 50 Phosphate (TMP) Tilia platyphyllos (Large-Leaved Linden), 18t, 42t, 312t, 392t Tillandsia usneoides, 392t, 413t, 469t TMP See Thiamine Monophosphate (TMP); Thymidine 50 -Phosphate (TMP) Tobacco See Nicotiana tabacum Tobacco, Aztec See Nicotiana rustica Tobacco, Jasmine See Nicotiana alata Tobacco, Longflower See Nicotiana longiflora Tobacco, Woodland See Nicotiana sylvestris Tomatillo See Physalis ixocarpa Tomato See Lycopersicon esculentum Tomato, Cherry See Lycopersicon esculentum, ssp cerasiforme Tomato, Tree See Cyphomandra betacea Tomato, Wild See Lycopersicon hirsutum, ssp glabratum Tonguefern, Hart’s See Phyllitis scolopendrium Toothleaf See Stillingia spp Torch Tree See Ixora parviflora Torreya nucifera (Kaya Nut), 223t Tortula ruralis, 312t Tosa-Buntan See Citrus grandis Totara, Snow See Podocarpus nivalis TPN See Nicotine Adenine Dinucleotide Phosphate Trapa natans (Water Chestnut), 70t Treculia africana (African Breadfruit), 89t Trefoil, Birdsfoot See Lotus corniculatus Trichodesma incanum, 89t, 223t Trichopilia tortilis, 223t Trichosanthes anguina (Snake Gourd), 89t Trifolium alexandrinum (Berseem Clover), 223t Trifolium incarnatum (Crimson Clover), 312t, 475–490 Trifolium pratense (Red Clover), 42t, 89t, 200t, 223t, 413t, 458t, 490–500 Trifolium repens (White Clover, Ladino), 42t, 89t, 158t, 223t, 380t, 432t Trifolium spp (Hartshorn Clover), 89t, 223t Trifolium subterraneum (Sub Clover), 18t, 42t, 89t, 392t, 475–490 Trigonella corniculata, 223t Trigonella foenum-graecum (Fenugreek), 89t, 223t, 312t, 392t, 413t, 475–490 Triose Phosphates, 9–28, 9f, 18t, 58 Triticosecale Witt (Triticale), 42t, 70t, 89t, 312t, 392t, 475–490 Triticum aegilopoides (Wild Einkorn), 223t Triticum aestivum (Wheat), 18t, 33t, 42t, 66t, 70t, 78t, 89t, 139t, 152t, 158t, 161t, 178t, 189t, 196t, 200t, 223t, 312t, 380t, 392t, 413t, 432t, 446t, 455t, 458t, 462t, 469t, 475–500 Triticum boeoticum (Wild Einkorn), 413t Triticum compactum (Club Wheat), 89t, 223t, 312t, 392t, 413t Triticum dicoccoides (Wild Emmer), 223t, 413t Triticum dicoccum (Emmer), 223t, 413t Triticum durum (Durum Wheat), 33t, 89t, 223t, 312t, 413t, 458t, 462t, 475–490 Triticum macha (Macha Wheat), 223t Triticum monococcum (Einkorn), 89t, 223t, 413t Triticum spelta (Spelt), 89t, 223t, 413t, 475–490 666 INDEX Triticum turgidum (Poulard Wheat), 89t Tsamiya See Tamarindus indica Tsuga heterophylla (Western Hemlock), 312t TTP See Thiamine Triphosphate (TTP); Thymidine 50 -Triphosphate (TTP) Tulipa spp (Tulip), 223t Tulip Tree See Liriodendron tulipifera Tung, Chinese See Aleuritis montana Turmeric See Curcuma longa Turnip, White See Brassica rapa, ssp rapa Tussilago farfara (Coltsfoot), 223t Typha latifolia (Common Cattail), 223t U UDP See Uridine 50 -Diphosphate (UDP) UDPApi See Uridine 50 -Diphosphate Apiose (UDPApi) UDPAra See Uridine 50 -Diphosphate Arabinose (UDPAra) UDPFru See Uridine 50 -Diphosphate Fructose (UDPFru) UDPFuc See Uridine 50 -Diphosphate Fucose (UDPFuc) UDPG See Uridine 50 -Diphosphate Glucose (UDPG/ UDPGlc) UDPGal See Uridine 50 -Diphosphate Galactose (UDPGal) UDPGalA See Uridine 50 -Diphosphate Galacturonic Acid (UDPGalA) UDPGalNAc See Uridine 50 -Diphosphate NAcetylgalactosamine (UDPGalNAc) UDPGlcA See Uridine 50 -Diphosphate Glucuronic Acid (UDPGlcA) UDPGlcNAc See Uridine 50 -Diphosphate NAcetylglucosamine (UDPGlcNAc) UDPMan See Uridine 50 -Diphosphate Mannose (UDPMan) UDPRha See Uridine 50 -Diphosphate Rhamnose (UDPRha) UDPRib See Uridine 50 -Diphosphate Ribose (UDPRib) UDPX See Uridine 50 -Diphosphate Sugars (UDPX) UDPXyl See Uridine 50 -Diphosphate Xylose (UDPXyl) Ukpo See Mucuna sloanei Ulmus davidiana ssp japonica (Japanese Elm), 312t Ulmus glabra (Wych Elm), 312t UMP See Uridine 50 -Phosphate (UMP) Undaria pinnatifida (Wakame), 432t Uniola paniculata (Sea Oats), 475–490 Uridine 50 -Diphosphate (UDP), 59f, 305–307, 309t, 311–346, 312t, 347, 349, 360, 361, 362–363, 387–388, 389, 390, 391, 392t, 404, 413t, 473t, 475–500 Uridine 50 -Diphosphate Apiose (UDPApi), 392t Uridine 50 -Diphosphate Arabinose (UDPAra), 389, 392t Uridine 50 -Diphosphate Digitoxose (UDPDig), 392t Uridine 50 -Diphosphate Fructose (UDPFru), 392t, 475–490 Uridine 50 -Diphosphate Fucose (UDPFuc), 392t Uridine 50 -Diphosphate Galactose (UDPGal), 59, 311–346, 388f, 389, 390, 392t, 403, 475–500 Uridine 50 -Diphosphate Galacturonic Acid (UDPGalA), 388f, 390, 392t Uridine 50 -Diphosphate Glucose (UDPG/ UDPGlc), 36f, 41–53, 59, 67, 309t, 311–346, 312t, 347, 349, 390, 391, 403, 404, 412, 471, 472t, 473t, 475–500 Uridine 50 -Diphosphate Glucuronic Acid (UDPGlcA), 388f, 389, 390, 392t Uridine 50 -Diphosphate Mannose (UDPMan), 392t, 403 Uridine 50 -Diphosphate NAcetylgalactosamine (UDPGalNAc), 389, 392t Uridine 50 -Diphosphate N-Acetylglucosamine (UDPGlcNAc), 388f, 389, 390, 392t, 403, 475–500 Uridine 50 -Diphosphate Rhamnose (UDPRha), 392t Uridine 50 -Diphosphate Ribose (UDPRib), 392t Uridine 50 -Diphosphate Sugars (UDPX), 312t, 390, 392t, 403, 473t, 475–500 Index 667 Uridine 50 -Diphosphate Xylose (UDPXyl), 388f, 389, 392t Uridine 50 -Phosphate (UMP), 305–307, 309t, 311–346, 312t, 347, 349, 360, 361–363, 378, 391, 404, 413t, 473t, 475–500 Uridine 50 -Triphosphate (UTP), 59, 305–307, 309t, 311–346, 312t, 347, 349, 354, 360, 361, 362–363, 367, 372, 388f, 391, 403, 404, 472t, 473t, 475–500 50 -Uridylic acid See Uridine 50 -Phosphate Urtica dioica (Stinging Nettle), 42t, 223t Utasi See Marsdenia latifolium UTP See Uridine 50 -Triphosphate (UTP) Utricularia vulgaris (Bladderwort), 223t V Vaccaria segetalis (Cow Herb), 89t Vaccinium macrocarpon (Cranberry), 223t Vaccinium myrtillus (Whortleberry), 223t Vallisneria gigantea (Eelgrass), 223t Vallisneria spiralis, 223t Vallisneria spp (Eelgrass), 223t Vanda teres, 223t Varagu See Paspalum scrobiculatum Vegetable Fern See Athyrium esculentum Velvetleaf See Abutilon theophrasti Velvetplant, Hawksbead See Crassocephalum crepidioides Verbascum thapsus (Mullein), 413t Vernonia amygdalina (Bitter Leaf), 89t Vernonia galamensis (Ironweed), 89t Vetch See Vicia spp Vetch, Hairy See Vicia villosa Vetch, Spring See Vicia sativa Vicia faba (Broad, Faba, Horse or Winds or Bean), 18t, 33t, 42t, 64–65, 66t, 70t, 89t, 152t, 178t, 189t, 196t, 200t, 208t, 223t, 312t, 363t, 380t, 392t, 413t, 432t, 462t, 469t, 475–500 ssp minor (Small Horse Bean), 89t, 152t, 475–490 Vicia faba ssp minor, 89t, 152t, 223t Vicia sativa (Spring Vetch), 312t, 413t Vicia spp (Vetch), 70t Vicia villosa (Hairy Vetch), 223t Vigna aconitifolia (Moth Bean), 89t, 475–490 Vigna ambecensis, 89t Vigna angularis (Adzuki Bean), 89t, 178t, 189t, 196t, 200t, 208t, 223t, 312t, 413t, 432t, 475–490 Vigna auriculata (Ronji), 223t Vigna catjang (Catjang), 89t Vigna luteola (Hairypod Cowpea), 89t Vigna mungo (Black Gram), 18t, 29t, 33t, 34–35, 42t, 66t, 89t, 161t, 223t, 312t, 380t, 392t, 432t, 475–500 Vigna oblongifolia, 89t Vigna racemosa, 89t Vigna radiata (Mung Bean, Green Gram), 18t, 42t, 70t, 89t, 152t, 223t, 312t, 392t, 413t, 432t, 462t, 475–490 Vigna reticulata, 89t Vigna sesquipedalis (Yard-Long Bean), 89t, 413t, 475–490 Vigna subterranea (Bambara Groundnut), 89t Vigna umbellata (Rice Bean), 89t, 475–490 Vigna unguiculata (Cowpea), 89t, 152t, 178t, 200t, 223t, 413t, 432t, 462t, 475–500 ssp dekindtiana, 89t Vigna vexillata (Zombi Pea), 89t ssp macrosperma, 223t Vinca erecta (Periwinkle), 89t Vinca minor (Periwinkle), 223t, 490–500 Viola tricolor (Field Pansy), 312t Violet, Flame See Episcia reptans Viscum album (Mistletoe), 89t, 223t Vitamins, 439–456 Vitex doniana, 89t Vitis coignetiae (Crimson Glory Vine), 446t Vitis riparia (Riverbank Grape), 223t Vitis spp (Grape), 432t Vitis vinifera (Wine Grape), 18t, 42t, 89t, 223t, 312t, 490–500 Voandzeia poissonii (Dougoufoulo), 89t W Wakame See Undaria pinnatifida Wallflower, Gray See Erysimum diffusum Walnut, Black See Juglans nigra Walnut, English See Juglans regia 668 INDEX Washingtonia filifera (California Fan Palm), 89t Watercress See Nasturtium officinale Water Fern See Azolla africana Water Fern, Ray See Blechnum fluviatile Water Lily, Yellow See Nuphar luteum Water Meal See Wolffiella floridana Water Meal, Spotless See Wolffia arrhiza Watermelon See Citrullus lanatus; Citrullus vulgaris Water Moss See Fontinalis antipyretica Water Nymph See Najas flexilis Water Reed See Phragmites communis Water Sprite See Ceratopteris thalictroides Waterweed, Brazilian See Egeria densa Waterweed, Canadian See Elodea canadensis Waterweed, Western See Elodea nuttallii Wattle, Crowded-Leaf See Acacia conferta Wattle, Green See Acacia decurrens Wheat See Triticum aestivum Wheat, Club See Triticum compactum Wheat, Durum See Triticum durum Wheatgrass, Crested See Agropyron desertorum Wheat, Macha See Triticum macha Wheat, Poulard See Triticum turgidum Whortleberry See Vaccinium myrtillus Wild Bishop See Bifora radians Willow, Almond See Salix triandra Willow, Basket See Salix viminalis Willow, Crack See Salix fragilis Willow, Dark-Leaved See Salix nigricans Willow, Dragon-Claw See Salix matsudana Willow, Dwarf See Salix herbacea Willow, Large Gray See Salix cinerea Willow, Netleaf See Salix reticulata Willow, Notchleaf See Salix retusa Willow, Weeping See Salix babylonica Willow, White See Salix alba Wistaria Tree, Scarlet See Sesbania grandiflora Witchweed See Striga asiatica Witchweed, Purple See Striga hermonthica Withania somnifera (Winter Cherry, Aswa-gandh), 223t Wolffia arrhiza (Spotless Water Meal), 312t, 413t Wolffiella floridana (Water Meal), 89t, 490–500 Wormwood See Artemisia turanica X Xanthium orientale (Oriental Cocklebur), 223t Xanthium pennsylvanicum (Cocklebur), 312t, 475–490 Xanthium strumarium (Cocklebur), 18t, 33t, 42t, 223t, 446t Xanthosoma mafaffa (Lime Zinger), 89t Xanthosoma sagittifolium (Tannia), 89t Xanthosoma spp (Cocoyam), 89t Xylia xylocarpa (Burma Pyinkado), 89t Xylomelum angustifolium, 89t Xylopia aethiopica (Guinea Pepper), 89t Xylose 1-Phosphate (Xyl1P), 388f Xylulose 5-Phosphate (Xu5P), 1, 6t, 10, 11, 28, 29–30, 31, 32, 33t, 34–35, 53, 54, 63, 64, 65 Y Yam See Dioscorea versicolor Yambean See Pachyrhizus erosus Yambean, African See Sphenostylis stenocarpa Yam, Chinese See Dioscorea batatas; Dioscorea opposita Yam, Elephant See Amorphophallus campanulatus Yam, Korean See Dioscorea aimadoimo Yam, Lesser See Dioscorea esculenta Yam, White Guinea See Dioscorea rotundata Yam, Winged See Dioscorea alata Yam, Yellow Guinea See Dioscorea cayenensis Yassar See Moringa peregrina Yellowtops See Flaveria cronquistii; Flaveria pubescens Yellowtops, Brown’s See Flaveria brownii Yellowtops, Clustered See Flaveria trinervia Yellowwood See Cladrastis lutea Yew, English See Taxus baccata Yew, Japanese See Taxus cuspidata Yew, Prince Albert See Saxegothaea conspicua Yucca aloifolia (Aloe Yucca), 413t Yucca flaccida (Weak-Leaf Yucca), 18t, 42t, 312t, 392t, 469t Index 669 Yuko See Citrus yuko Yulan See Magnolia denudata Yuzu See Citrus junos Z Zantedeschia aethiopica (Arum Lily), 89t, 223t Zea mays (Corn, Maize), 7t, 18t, 33t, 42t, 59, 63t, 70t, 89t, 139t, 152t, 158t, 178t, 189t, 200t, 208t, 212t, 223t, 312t, 380t, 392t, 413t, 432t, 446t, 458t, 462t, 469t, 472t, 475–500 ssp indentata (Dent Corn), 223t, 490–500 ssp indurata (Flint Corn), 223t ssp saccharata (Sweet Corn), 178t, 189t, 208t, 223t Zingiber officinale (Ginger), 89t, 223t Ziziphus jujuba (Jujube), 223t, 380t Ziziphus vulgaris ssp inermis ssp spinosus, 380t Ziziphus vulgaris ssp inermis, 380t, 490–500 Zostera asiatica, 223t Zostera capricorni, 223t Zostera marina L (Seawrack), 223t, 312t Zostera nana, 223t Zygophyllum album (White Bean Caper), 223t ... combined index of the plants and phosphorus compounds The Phosphorus Compounds Nomenclature The naming of the phosphorus compounds in this book conforms to the recommendations of the Drake Committee... engaged in any aspect of plant research chemistry, biochemistry, or physiology—with primary focus on the chemistry of phosphorus- containing compounds that occur naturally in the plant kingdom and... “Effects of Sodium on Photosynthesis in Panicum coloratum”, Plant Cell Physiol 1992, 33(8), 1239–1242,7 reprinted by permission of Oxford University Press, © 1992 Chemistry of Plant Phosphorus Compounds