<!DOCTYPE html PUBLIC "-//W3C//DTD XHTML 1.0 Transitional//EN" "http://www.w3.org/TR/xhtml1/DTD/xhtml1-transitional.dtd"> <html> <head> <title>UTas ePrints - Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatrography-electrospray ionisation mass spectrometry</title> <script type="text/javascript" src="http://eprints.utas.edu.au/javascript/auto.js"><!-- padder --></script> <style type="text/css" media="screen">@import url(http://eprints.utas.edu.au/style/auto.css);</style> <style type="text/css" media="print">@import url(http://eprints.utas.edu.au/style/print.css);</style> <link rel="icon" href="/images/eprints/favicon.ico" type="image/x-icon" /> <link rel="shortcut icon" href="/images/eprints/favicon.ico" type="image/x-icon" /> <link rel="Top" href="http://eprints.utas.edu.au/" /> <link rel="Search" href="http://eprints.utas.edu.au/cgi/search" /> <meta content="Barry, K.M." name="eprints.creators_name" /> <meta content="Davies, N.W." name="eprints.creators_name" /> <meta content="Mohammed, C.L." name="eprints.creators_name" /> <meta content="Karen.Barry@utas.edu.au" name="eprints.creators_id" /> <meta content="" name="eprints.creators_id" /> <meta content="" name="eprints.creators_id" /> <meta content="article" name="eprints.type" /> <meta content="2007-10-11 04:41:06" name="eprints.datestamp" /> <meta content="2008-01-08 15:30:00" name="eprints.lastmod" /> <meta content="show" name="eprints.metadata_visibility" /> <meta content="Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatrography-electrospray ionisation mass spectrometry" name="eprints.title" /> <meta content="pub" name="eprints.ispublished" /> <meta content="300603" name="eprints.subjects" /> <meta content="250302" name="eprints.subjects" /> <meta content="restricted" name="eprints.full_text_status" /> <meta content="HPLC; electrospray MS; tannin; ellagitannin; gallotannin; antimicrobial; Eucalyptus sp. " name="eprints.keywords" /> <meta content="Copyright 2001 Wiley InterScience. Definitive version available online at http://www.interscience.wiley.com/" name="eprints.note" /> <meta content="The first detailed analysis of the phenolic constituents of the reaction zones (tissue of antimicrobial defence) from the sapwood of a Eucalyptus spp. is presented. Plantation-grown Eucalyptus nitens trees with stem decay resulting from pruning wounds were sampled and extracts were prepared from healthy sapwood and from reaction zone tissue. Analysis by HPLC with ESI-MS revealed that a diverse range of hydrolysable tannins are present in both healthy sapwood and in reaction zone extracts, including over 30 gallotannins, ellagitannins and phenols. Eight tannins were unequivocally identified, including the gallotannins tri-O-galloyl-β-D-glucose, tetra-O-galloyl-β-D-glucose and penta-O-galloyl-β-D-glucose, and the ellagitannins pedunculagin, tellimagrandin I, casuarinin, casuarictin and tellimagrandin II. The phenols gallic acid, ellagic acid and catechin were also identified. The ellagitannins (particularly pedunculagin) are considerably more abundant in the reaction zone than in the healthy sapwood and may contribute to the effectiveness of the reaction zone as an antimicrobial barrier." name="eprints.abstract" /> <meta content="2001-03-16" name="eprints.date" /> <meta content="published" name="eprints.date_type" /> <meta content="Phytochemical Analysis" name="eprints.publication" /> <meta content="12" name="eprints.volume" /> <meta content="2" name="eprints.number" /> <meta content="120-127" name="eprints.pagerange" /> <meta content="10.1002/pca.548" name="eprints.id_number" /> <meta content="TRUE" name="eprints.refereed" /> <meta content="http://dx.doi.org/10.1002/pca.548" name="eprints.official_url" /> <meta content="Barry KM, Pearce RB, Mohammed CL. 2000. Properties of reaction zones associated with decay from pruning wounds in plantation-grown Eucalyptus nitens. Eur J Pathol 30: 233-245. Boddy L, Rayner ADM. 1983. Origins of decay in living deciduous trees: the role of moisture content and a reappraisal of the expanded concept of tree decay. New Phytol 94: 623-641. Cadahia E, Conde E, Garcia-Vallejo MC, Fernandez de Simon B. 1997. Tannin composition of Eucalyptus camaldulensis, E. globulus and E. rudis I. Wood. Holzforschung 51: 119-124. Conde E, Cadahia E, Garcia-Vallejo MC, Tomas-Barberan F. 1995. Low molecular weight polyphenols in wood and bark of Eucalyptus globulus. Wood Fiber Sci 27: 379-383. Field JA, Lettinga G. 1992. Toxicity of tannic compounds to microorganisms. In Plant Polyphenols, Hemingway RW, Laks PE (eds). Plenum Press: New York; 673-692. Hagerman AE, Riedl KM, Jones A, Sovik KN, Ritchard NT, Hartzfeld PW, Riechel TL. 1998. High molecular weight plant polyphenolics (tannins) as biological antioxidants. J Agric Food Chem 46: 1887-1892. Hart JH, Hillis WE. 1972. Inhibition of wood-rotting fungi by ellagitannins in the heartwood of Quercus alba. Phytopathology 62: 620-626. Hart JH, Hillis WE. 1974. Inhibition of wood-rotting fungi by stilbenes and other polyphenols in Eucalyptus sideroxylon. Phytopathology 64: 939-948. Haslam E. 1989. Plant Polyphenols, Vegetable Tannins Revisited. Cambridge University Press: Cambridge. Hatano T, Kira R, Yoshizaki M and Okuda T. 1986. Seasonal changes in the tannins of Liquidambar formasana re¯ecting their biogenesis. Phytochemistry 25: 2787- 2789. Hatano T, Yoshida T and Okuda T. 1988. Chromatography of tannins III. Multiple peaks in high-performance liquid chromatography of some hydrolyzable tannins. J Chromatogr 435: 285-295. Hillis WE. 1987. Heartwood and Tree Exudates. Springer: Berlin. Hillis WE, Yazaki Y. 1973. Wood polyphenols of Eucalyptus polyanthemos. Phytochemistry 12: 2969-2977. Kawamoto H, Mizutani K, Nakatsubo F. 1997. Binding nature and denaturation of protein during interaction with galloylglucose. Phytochemistry 46: 473-478. Mila I, Scalbert A, Expert D. 1996. Iron withholding by plant pathogens and resistance to pathogens and rots. Phytochemistry 42: 1551-1555. Nawwar MAM, Marzouk MS, Nigge W, Linscheid M. 1997. High performance liquid chromatographic / electrospray ionisation mass spectrometric screening for polyphenolic compounds of Epilbium hirsutum Ð the structure of the unique ellagitannin epilobamide-A. J Mass Spectrom 32: 645-654. Okamura H, Mimura A, Yakou Y, Niwano M, Takahra Y. 1993. Antioxidant activity of tannins and ¯avonoids in Eucalyptus rostrata. Phytochemistry 33: 557-561. Okuda T, Yoshida T, Hatano T. 1995. Hydrolysable tannins and related polyphenols. Prog Chem Org Nat Prod 66: 1- 117. Pearce RB. 1996. Anti-microbial defences in the wood of living trees. New Phytol 132: 203-233. Puech J-L, Mertz C, Michon V, Guerneve CL, Doco T, du Penhoat CH. 1999. Evolution of castalagin and vescalagin in ethanol solutions. Identi®cation of new derivatives. J Agric Food Chem 47: 2060-2066. Scalbert A. 1992. Tannins in woods and their contribution to microbial decay prevention. In Plant Polyphenols, Hemingway RW, Laks PE (eds). Plenum Press: New York; 935- 952. Scalbert A, Monties B, Favre J. 1988. Polyphenols of Quercus robur: adult tree and in vitro grown callus and shoots. Phytochemistry 27: 3483-3488. Seikel MK, Hillis WE. 1970. Hydrolysable tannins of Eucalyptus delegatensis wood. Phytochemistry 9: 1115-1128. Shain L. 1979. Dynamic responses of differentiated sapwood to injury and infection. Phytopathology 69: 1143-1147. Yamada T, Tamura H, Mineo K. 1988. The responses of sugi (Cryptomeria japonica D. Don) sapwood to fungal invasion following attack by the sugi bark borer. Physiol Mol Plant Pathol 33: 429-442. Yazaki Y, Collins PJ, Iwashina T. 1993. Extractives from blackbutt (Eucalyptus pilularis) wood which affects gluebond quality of phenolic resins. Holzforschung 47: 412-418. Zucker WV. 1983. Tannins: Does structure determine function? An ecological perspective. Am Naturalist 121: 335- 365. ANALYSIS OF HYDROLYSABLE TANNINS IN EUCALYPTUS WOOD 127 Copyright # 2001 John Wiley & Sons, Ltd. Phytochem. Anal. 12: 120–127 (2001)" name="eprints.referencetext" /> <meta content="Barry, K.M. and Davies, N.W. and Mohammed, C.L. (2001) Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatrography-electrospray ionisation mass spectrometry. Phytochemical Analysis, 12 (2). pp. 120-127." name="eprints.citation" /> <meta content="http://eprints.utas.edu.au/2088/1/fulltext_Barry2001PCA.pdf" name="eprints.document_url" /> <link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /> <meta content="Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatrography-electrospray ionisation mass spectrometry" name="DC.title" /> <meta content="Barry, K.M." name="DC.creator" /> <meta content="Davies, N.W." name="DC.creator" /> <meta content="Mohammed, C.L." name="DC.creator" /> <meta content="300603 Pests, Health and Diseases" name="DC.subject" /> <meta content="250302 Biological and Medical Chemistry" name="DC.subject" /> <meta content="The first detailed analysis of the phenolic constituents of the reaction zones (tissue of antimicrobial defence) from the sapwood of a Eucalyptus spp. is presented. Plantation-grown Eucalyptus nitens trees with stem decay resulting from pruning wounds were sampled and extracts were prepared from healthy sapwood and from reaction zone tissue. Analysis by HPLC with ESI-MS revealed that a diverse range of hydrolysable tannins are present in both healthy sapwood and in reaction zone extracts, including over 30 gallotannins, ellagitannins and phenols. Eight tannins were unequivocally identified, including the gallotannins tri-O-galloyl-β-D-glucose, tetra-O-galloyl-β-D-glucose and penta-O-galloyl-β-D-glucose, and the ellagitannins pedunculagin, tellimagrandin I, casuarinin, casuarictin and tellimagrandin II. The phenols gallic acid, ellagic acid and catechin were also identified. The ellagitannins (particularly pedunculagin) are considerably more abundant in the reaction zone than in the healthy sapwood and may contribute to the effectiveness of the reaction zone as an antimicrobial barrier." name="DC.description" /> <meta content="2001-03-16" name="DC.date" /> <meta content="Article" name="DC.type" /> <meta content="PeerReviewed" name="DC.type" /> <meta content="application/pdf" name="DC.format" /> <meta content="http://eprints.utas.edu.au/2088/1/fulltext_Barry2001PCA.pdf" name="DC.identifier" /> <meta content="http://dx.doi.org/10.1002/pca.548" name="DC.relation" /> <meta content="Barry, K.M. and Davies, N.W. and Mohammed, C.L. (2001) Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatrography-electrospray ionisation mass spectrometry. 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border: solid 1px #ccc; padding: 3px"><tr> <td align="left"><a href="http://eprints.utas.edu.au/cgi/users/home">Login</a> | <a href="http://eprints.utas.edu.au/cgi/register">Create Account</a></td> <td align="right" style="white-space: nowrap"> <form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/search" style="display:inline"> <input class="ep_tm_searchbarbox" size="20" type="text" name="q" /> <input class="ep_tm_searchbarbutton" value="Search" type="submit" name="_action_search" /> <input type="hidden" name="_order" value="bytitle" /> <input type="hidden" name="basic_srchtype" value="ALL" /> <input type="hidden" name="_satisfyall" value="ALL" /> </form> </td> </tr></table></td></tr> <tr> <td class="toplinks"><!-- InstanceBeginEditable name="content" --> <div align="center"> <table width="720" class="ep_tm_main"><tr><td align="left"> <h1 class="ep_tm_pagetitle">Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatrography-electrospray ionisation mass spectrometry</h1> <p style="margin-bottom: 1em" class="not_ep_block"><span class="person_name">Barry, K.M.</span> and <span class="person_name">Davies, N.W.</span> and <span class="person_name">Mohammed, C.L.</span> (2001) <xhtml:em>Identification of hydrolysable tannins in the reaction zone of Eucalyptus nitens wood by high performance liquid chromatrography-electrospray ionisation mass spectrometry.</xhtml:em> Phytochemical Analysis, 12 (2). pp. 120-127.</p><p style="margin-bottom: 1em" class="not_ep_block"></p><table style="margin-bottom: 1em" class="not_ep_block"><tr><td valign="top" style="text-align:center"><a href="http://eprints.utas.edu.au/2088/1/fulltext_Barry2001PCA.pdf"><img alt="[img]" src="http://eprints.utas.edu.au/style/images/fileicons/application_pdf.png" class="ep_doc_icon" border="0" /></a></td><td valign="top"><a href="http://eprints.utas.edu.au/2088/1/fulltext_Barry2001PCA.pdf"><span class="ep_document_citation">PDF</span></a> - Full text restricted - Requires a PDF viewer<br />141Kb</td><td><form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/request_doc"><input accept-charset="utf-8" value="2625" name="docid" type="hidden" /><div class=""><input value="Request a copy" name="_action_null" class="ep_form_action_button" onclick="return EPJS_button_pushed( '_action_null' )" type="submit" /> </div></form></td></tr></table><p style="margin-bottom: 1em" class="not_ep_block">Official URL: <a href="http://dx.doi.org/10.1002/pca.548">http://dx.doi.org/10.1002/pca.548</a></p><div class="not_ep_block"><h2>Abstract</h2><p style="padding-bottom: 16px; text-align: left; margin: 1em auto 0em auto">The first detailed analysis of the phenolic constituents of the reaction zones (tissue of antimicrobial defence) from the sapwood of a Eucalyptus spp. is presented. Plantation-grown Eucalyptus nitens trees with stem decay resulting from pruning wounds were sampled and extracts were prepared from healthy sapwood and from reaction zone tissue. Analysis by HPLC with ESI-MS revealed that a diverse range of hydrolysable tannins are present in both healthy sapwood and in reaction zone extracts, including over 30 gallotannins, ellagitannins and phenols. Eight tannins were unequivocally identified, including the gallotannins tri-O-galloyl-β-D-glucose, tetra-O-galloyl-β-D-glucose and penta-O-galloyl-β-D-glucose, and the ellagitannins pedunculagin, tellimagrandin I, casuarinin, casuarictin and tellimagrandin II. The phenols gallic acid, ellagic acid and catechin were also identified. The ellagitannins (particularly pedunculagin) are considerably more abundant in the reaction zone than in the healthy sapwood and may contribute to the effectiveness of the reaction zone as an antimicrobial barrier.</p></div><table style="margin-bottom: 1em" cellpadding="3" class="not_ep_block" border="0"><tr><th valign="top" class="ep_row">Item Type:</th><td valign="top" class="ep_row">Article</td></tr><tr><th valign="top" class="ep_row">Additional Information:</th><td valign="top" class="ep_row">Copyright 2001 Wiley InterScience. Definitive version available online at http://www.interscience.wiley.com/</td></tr><tr><th valign="top" class="ep_row">Keywords:</th><td valign="top" class="ep_row">HPLC; electrospray MS; tannin; ellagitannin; gallotannin; antimicrobial; Eucalyptus sp. </td></tr><tr><th valign="top" class="ep_row">Subjects:</th><td valign="top" class="ep_row"><a href="http://eprints.utas.edu.au/view/subjects/300603.html">300000 Agricultural, Veterinary and Environmental Sciences > 300600 Forestry Sciences > 300603 Pests, Health and Diseases</a><br /><a href="http://eprints.utas.edu.au/view/subjects/250302.html">250000 Chemical Sciences > 250300 Organic Chemistry > 250302 Biological and Medical Chemistry</a></td></tr><tr><th valign="top" class="ep_row">ID Code:</th><td valign="top" class="ep_row">2088</td></tr><tr><th valign="top" class="ep_row">Deposited By:</th><td valign="top" class="ep_row"><span class="ep_name_citation"><span class="person_name">Dr Karen Barry</span></span></td></tr><tr><th valign="top" class="ep_row">Deposited On:</th><td valign="top" class="ep_row">11 Oct 2007 15:41</td></tr><tr><th valign="top" class="ep_row">Last Modified:</th><td valign="top" class="ep_row">09 Jan 2008 02:30</td></tr><tr><th valign="top" class="ep_row">ePrint Statistics:</th><td valign="top" class="ep_row"><a target="ePrintStats" href="/es/index.php?action=show_detail_eprint;id=2088;">View statistics for this ePrint</a></td></tr></table><p align="right">Repository Staff Only: <a href="http://eprints.utas.edu.au/cgi/users/home?screen=EPrint::View&eprintid=2088">item control page</a></p> </td></tr></table> </div> <!-- InstanceEndEditable --></td> </tr> <tr> <td><!-- #BeginLibraryItem "/Library/footer_eprints.lbi" --> <table width="795" border="0" align="left" cellpadding="0" class="footer"> <tr valign="top"> <td colspan="2"><div align="center"><a href="http://www.utas.edu.au">UTAS home</a> | <a href="http://www.utas.edu.au/library/">Library home</a> | <a href="/">ePrints home</a> | <a href="/contact.html">contact</a> | <a href="/information.html">about</a> | <a href="/view/">browse</a> | <a href="/perl/search/simple">search</a> | <a href="/perl/register">register</a> | <a href="/perl/users/home">user area</a> | <a href="/help/">help</a></div><br /></td> </tr> <tr><td colspan="2"><p><img src="/images/eprints/footerline.gif" width="100%" height="4" /></p></td></tr> <tr valign="top"> <td width="68%" class="footer">Authorised by the University Librarian<br /> © University of Tasmania ABN 30 764 374 782<br /> <a href="http://www.utas.edu.au/cricos/">CRICOS Provider Code 00586B</a> | <a href="http://www.utas.edu.au/copyright/copyright_disclaimers.html">Copyright & Disclaimers</a> | <a href="http://www.utas.edu.au/accessibility/index.html">Accessibility</a> | <a href="http://eprints.utas.edu.au/feedback/">Site Feedback</a> </td> <td width="32%"><div align="right"> <p align="right" class="NoPrint"><a href="http://www.utas.edu.au/"><img src="http://www.utas.edu.au/shared/logos/unioftasstrip.gif" alt="University of Tasmania Home Page" width="260" height="16" border="0" align="right" /></a></p> <p align="right" class="NoPrint"><a href="http://www.utas.edu.au/"><br /> </a></p> </div></td> </tr> <tr valign="top"> <td><p> </p></td> <td><div align="right"><span class="NoPrint"><a href="http://www.eprints.org/software/"><img src="/images/eprintslogo.gif" alt="ePrints logo" width="77" height="29" border="0" align="bottom" /></a></span></div></td> </tr> </table> <!-- #EndLibraryItem --> <div align="center"></div></td> </tr> </table> </body> </html>