<?xml version="1.0" encoding="UTF-8"?><xml><records><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Evidente, Antonio</style></author><author><style face="normal" font="default" size="100%">Masi, Marco</style></author><author><style face="normal" font="default" size="100%">Linaldeddu, Benedetto T.</style></author><author><style face="normal" font="default" size="100%">Franceschini, Antonio</style></author><author><style face="normal" font="default" size="100%">Scanu, Bruno</style></author><author><style face="normal" font="default" size="100%">Cimmino, Alessio</style></author><author><style face="normal" font="default" size="100%">Andolfi, Anna</style></author><author><style face="normal" font="default" size="100%">Motta, Andrea</style></author><author><style face="normal" font="default" size="100%">Maddau, Lucia</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">Afritoxinones A and B, dihydrofuropyran-2-ones produced by Diplodia africana the causal agent of branch dieback on Juniperus phoenicea</style></title><secondary-title><style face="normal" font="default" size="100%">PHYTOCHEMISTRY</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">Afritoxinones A and B</style></keyword><keyword><style  face="normal" font="default" size="100%">Botryosphaeriaceae</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplodia africana</style></keyword><keyword><style  face="normal" font="default" size="100%">Juniperus phoenicea</style></keyword><keyword><style  face="normal" font="default" size="100%">Phytotoxins</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2012</style></year><pub-dates><date><style  face="normal" font="default" size="100%">2012///</style></date></pub-dates></dates><volume><style face="normal" font="default" size="100%">77</style></volume><pages><style face="normal" font="default" size="100%">245 - 250</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Two phytotoxic dihydrofuropyran-2-ones, named afritoxinones A and B. were isolated from liquid culture of Diplodia africana. a fungal pathogen responsible for branch dieback of Phoenicean juniper in Italy. Additionally, six others known metabolites were isolated and characterized: oxysporone, sphaeropsidin A, epi-sphaeropsidone, R-(-)-mellein, (3R,4R)-4-hydroxymellein and (3R,4S)-4-hydroxymellein. The structures of afritoxinones A and B were established by spectroscopic and optical methods and determined to be as (3aS{*},6R{*}-,7aS)-6-methoxy-3a,7a-dihydro-3H,6H-furo\{[\}2,3-b]pyran-2-o ne and (3aR{*},6R{*},7aS)-6-methoxy-3a,7a-dihydro-3H,6H-furo\{[\}2,3-b]pyran-2-on e, respectively. The phytotoxic activity of afritoxinones A and B and oxysporone was evaluated on host (Phoenicean juniper) and non-host plant (holm oak, cork oak and tomato) by cutting and leaf puncture assay. Oxysporone proved to be the most phytotoxic compound. This study represents the first report of secondary metabolites produced by D. africana. In addition, the taxonomic implications of secondary metabolites in Botryosphaeriaceae family studies are discussed. (C) 2012 Elsevier Ltd. All rights reserved.</style></abstract><notes><style face="normal" font="default" size="100%">The following values have no corresponding Zotero field:&lt;br/&gt;pub-location: THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND&lt;br/&gt;publisher: PERGAMON-ELSEVIER SCIENCE LTD</style></notes></record><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Evidente, Antonio</style></author><author><style face="normal" font="default" size="100%">Maddau, Lucia</style></author><author><style face="normal" font="default" size="100%">Scanu, Bruno</style></author><author><style face="normal" font="default" size="100%">Andolfi, Anna</style></author><author><style face="normal" font="default" size="100%">Masi, Marco</style></author><author><style face="normal" font="default" size="100%">Motta, Andrea</style></author><author><style face="normal" font="default" size="100%">Tuzi, Angela</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">Sphaeropsidones, Phytotoxic Dimedone Methyl Ethers Produced by Diplodia cupressi: A Structure−Activity Relationship Study</style></title><secondary-title><style face="normal" font="default" size="100%">Journal of Natural Products</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">antifungal activity (voyant)</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplodia cupressi</style></keyword><keyword><style  face="normal" font="default" size="100%">Phytotoxicity</style></keyword><keyword><style  face="normal" font="default" size="100%">Sphaeropsidones</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2011</style></year><pub-dates><date><style  face="normal" font="default" size="100%">2011///</style></date></pub-dates></dates><urls><web-urls><url><style face="normal" font="default" size="100%">http://dx.doi.org/10.1021/np100837r</style></url></web-urls></urls><volume><style face="normal" font="default" size="100%">74</style></volume><pages><style face="normal" font="default" size="100%">757 - 763</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Sphaeropsidone and episphaeropsidone are two phytotoxic dimedone methyl ethers produced by Diplodia cupressi, the causal agent of a canker disease of cypress in the Mediterranean area. In this study, eight derivatives obtained by chemical modifications and two natural analogues were assayed for phytotoxic and antifungal activities, and a structure?activity relationship was examined. Each compound was tested on nonhost plants and on five fungal pathogenic species belonging to the genus Phytophthora. The results provide insights into structure?activity relationships within these compounds. It was found that the hydroxy group at C-5, the absolute C-5 configuration, the epoxy group, and the C-2 carbonyl group appear to be structural features important in conferring biological activity. The conversion of sphaeropsidone into the corresponding 1,4-dione derivative led to a compound showing greater antifungal activity than its precursor. This finding could be useful in devising new natural fungicides for practical application in agriculture.</style></abstract><issue><style face="normal" font="default" size="100%">4</style></issue><notes><style face="normal" font="default" size="100%">doi: 10.1021/np100837rdoi: 10.1021/np100837rThe following values have no corresponding Zotero field:&lt;br/&gt;publisher: American Chemical Society</style></notes></record><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Evidente, Antonio</style></author><author><style face="normal" font="default" size="100%">Andolfi, Anna</style></author><author><style face="normal" font="default" size="100%">Fiore, Michele</style></author><author><style face="normal" font="default" size="100%">Spanu, Emanuela</style></author><author><style face="normal" font="default" size="100%">Maddau, Lucia</style></author><author><style face="normal" font="default" size="100%">Franceschini, Antonio</style></author><author><style face="normal" font="default" size="100%">Marras, Francesco</style></author><author><style face="normal" font="default" size="100%">Motta, Andrea</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">Diplobifuranylones A and B, 5‘-Monosubstituted Tetrahydro-2H-bifuranyl-5-ones Produced by Diplodia corticola, a Fungus Pathogen of Cork Oak</style></title><secondary-title><style face="normal" font="default" size="100%">Journal of Natural Products</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">Chemical characterization</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplobifuranylones</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplodia corticola</style></keyword><keyword><style  face="normal" font="default" size="100%">metabolites</style></keyword><keyword><style  face="normal" font="default" size="100%">Phytotoxicity (voyant)</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2006</style></year></dates><publisher><style face="normal" font="default" size="100%">American Chemical Society</style></publisher><volume><style face="normal" font="default" size="100%">69</style></volume><pages><style face="normal" font="default" size="100%">671-674</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Two new 5?-monosubstituted tetrahydro-2H-bifuranyl-5-ones, named diplobifuranylones A and B (1 and 2), were isolated from the culture filtrates of Diplodia corticola, the causal agent of a canker of cork oak (Quercus suber). The same fungus also produced eight known metabolites, namely, the diplopyrone, (3S,4R)-trans- and (3R,4R)-cis-4-hydroxymellein, sapinofuranone B and its (S,S)-enantiomer, and sphaeropsidins A?C. Diplobifuranylones A and B (1 and 2) were characterized, using spectroscopic and chemical methods, as two diastereomeric 5?-(1-hydroxyethyl)-3,4,2?,5?-tetrahydro-2H-[2,2?]bifuranyl-5-ones. While the relative stereochemistry of the two metabolites (1 and 2) was deduced by NOESY and ROESY experiments, the absolute stereochemistry of the chiral carbon of the hydroxyethyl side chain at C-5?, determined by application of Mosher's method, proved to be S and R in 1 and 2, respectively. Assayed on a nonhost plant, diplobifuranylones A and B did not show phytotoxic activity. In an Artemia salina larvae lethality bioassay neither 1 nor 2 was toxic at the highest concentration tested (300 ?g/mL).</style></abstract><notes><style face="normal" font="default" size="100%">doi: 10.1021/np050393l</style></notes><research-notes><style face="normal" font="default" size="100%">doi: 10.1021/np050393l</style></research-notes></record><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Evidente, Antonio</style></author><author><style face="normal" font="default" size="100%">Andolfi, Anna</style></author><author><style face="normal" font="default" size="100%">Fiore, Michele</style></author><author><style face="normal" font="default" size="100%">Spanu, Emanuela</style></author><author><style face="normal" font="default" size="100%">Maddau, Lucia</style></author><author><style face="normal" font="default" size="100%">Franceschini, Antonio</style></author><author><style face="normal" font="default" size="100%">Marras, Francesco</style></author><author><style face="normal" font="default" size="100%">Motta, Andrea</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">Diplobifuranylones A and B, 5‘-Monosubstituted Tetrahydro-2H-bifuranyl-5-ones Produced by Diplodia corticola, a Fungus Pathogen of Cork Oak</style></title><secondary-title><style face="normal" font="default" size="100%">Journal of Natural Products</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">Chemical characterization</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplobifuranylones</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplodia corticola</style></keyword><keyword><style  face="normal" font="default" size="100%">metabolites</style></keyword><keyword><style  face="normal" font="default" size="100%">Phytotoxicity (voyant)</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2006</style></year><pub-dates><date><style  face="normal" font="default" size="100%">2006///</style></date></pub-dates></dates><urls><web-urls><url><style face="normal" font="default" size="100%">http://dx.doi.org/10.1021/np050393l</style></url></web-urls></urls><volume><style face="normal" font="default" size="100%">69</style></volume><pages><style face="normal" font="default" size="100%">671 - 674</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Two new 5?-monosubstituted tetrahydro-2H-bifuranyl-5-ones, named diplobifuranylones A and B (1 and 2), were isolated from the culture filtrates of Diplodia corticola, the causal agent of a canker of cork oak (Quercus suber). The same fungus also produced eight known metabolites, namely, the diplopyrone, (3S,4R)-trans- and (3R,4R)-cis-4-hydroxymellein, sapinofuranone B and its (S,S)-enantiomer, and sphaeropsidins A?C. Diplobifuranylones A and B (1 and 2) were characterized, using spectroscopic and chemical methods, as two diastereomeric 5?-(1-hydroxyethyl)-3,4,2?,5?-tetrahydro-2H-[2,2?]bifuranyl-5-ones. While the relative stereochemistry of the two metabolites (1 and 2) was deduced by NOESY and ROESY experiments, the absolute stereochemistry of the chiral carbon of the hydroxyethyl side chain at C-5?, determined by application of Mosher's method, proved to be S and R in 1 and 2, respectively. Assayed on a nonhost plant, diplobifuranylones A and B did not show phytotoxic activity. In an Artemia salina larvae lethality bioassay neither 1 nor 2 was toxic at the highest concentration tested (300 ?g/mL).</style></abstract><issue><style face="normal" font="default" size="100%">4</style></issue><notes><style face="normal" font="default" size="100%">doi: 10.1021/np050393ldoi: 10.1021/np050393lThe following values have no corresponding Zotero field:&lt;br/&gt;publisher: American Chemical Society</style></notes></record><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Evidente, Antonio</style></author><author><style face="normal" font="default" size="100%">Maddau, Lucia</style></author><author><style face="normal" font="default" size="100%">Spanu, Emanuela</style></author><author><style face="normal" font="default" size="100%">Franceschini, Antonio</style></author><author><style face="normal" font="default" size="100%">Lazzaroni, Silvia</style></author><author><style face="normal" font="default" size="100%">Motta, Andrea</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">Diplopyrone, a New Phytotoxic Tetrahydropyranpyran-2-one Produced by Diplodia mutila, a Fungus Pathogen of Cork Oak</style></title><secondary-title><style face="normal" font="default" size="100%">Journal of Natural Products</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">Phytopathogenic fungi</style></keyword><keyword><style  face="normal" font="default" size="100%">Phytotoxins</style></keyword><keyword><style  face="normal" font="default" size="100%">relative and/or absolute configuration</style></keyword><keyword><style  face="normal" font="default" size="100%">structure–activity relationships</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2003</style></year></dates><publisher><style face="normal" font="default" size="100%">American Chemical Society</style></publisher><volume><style face="normal" font="default" size="100%">66</style></volume><pages><style face="normal" font="default" size="100%">313-315</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">A new phytotoxic monosubstituted tetrahydropyranpyran-2-one, named diplopyrone (1), was isolated from the liquid culture filtrates of Diplodia mutila, a plant pathogenic fungus causing a form of canker disease of cork oak (Quercus suber). Diplopyrone was characterized, using spectroscopic and chemical methods, as 6-[(1S)-1-hydroxyethyl]-2,4a,6,8a-tetrahydropyran[3,2-b]pyran-2-one. The absolute stereochemistry of the chiral secondary hydroxylated carbon (C-9), determined by application of Mosher's method, proved to be S. Diplopyrone assayed at a 0.01?0.1 mg/mL concentration range caused necrosis and wilting on cork oak cuttings. On a nonhost plant, tomato, diplopyrone caused brown discoloration or stewing on the stem.</style></abstract><accession-num><style face="normal" font="default" size="100%">12608876</style></accession-num></record><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Evidente, Antonio</style></author><author><style face="normal" font="default" size="100%">Maddau, Lucia</style></author><author><style face="normal" font="default" size="100%">Spanu, Emanuela</style></author><author><style face="normal" font="default" size="100%">Franceschini, Antonio</style></author><author><style face="normal" font="default" size="100%">Lazzaroni, Silvia</style></author><author><style face="normal" font="default" size="100%">Motta, Andrea</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">Diplopyrone, a New Phytotoxic Tetrahydropyranpyran-2-one Produced by Diplodia mutila, a Fungus Pathogen of Cork Oak</style></title><secondary-title><style face="normal" font="default" size="100%">Journal of Natural Products</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">Phytopathogenic fungi</style></keyword><keyword><style  face="normal" font="default" size="100%">Phytotoxins</style></keyword><keyword><style  face="normal" font="default" size="100%">relative and/or absolute configuration</style></keyword><keyword><style  face="normal" font="default" size="100%">structure–activity relationships</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2003</style></year><pub-dates><date><style  face="normal" font="default" size="100%">2003///</style></date></pub-dates></dates><urls><web-urls><url><style face="normal" font="default" size="100%">http://www.ncbi.nlm.nih.gov/pubmed/12608876http://dx.doi.org/10.1021/np020367c</style></url></web-urls></urls><volume><style face="normal" font="default" size="100%">66</style></volume><pages><style face="normal" font="default" size="100%">313 - 315</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">A new phytotoxic monosubstituted tetrahydropyranpyran-2-one, named diplopyrone (1), was isolated from the liquid culture filtrates of Diplodia mutila, a plant pathogenic fungus causing a form of canker disease of cork oak (Quercus suber). Diplopyrone was characterized, using spectroscopic and chemical methods, as 6-[(1S)-1-hydroxyethyl]-2,4a,6,8a-tetrahydropyran[3,2-b]pyran-2-one. The absolute stereochemistry of the chiral secondary hydroxylated carbon (C-9), determined by application of Mosher's method, proved to be S. Diplopyrone assayed at a 0.01?0.1 mg/mL concentration range caused necrosis and wilting on cork oak cuttings. On a nonhost plant, tomato, diplopyrone caused brown discoloration or stewing on the stem.</style></abstract><issue><style face="normal" font="default" size="100%">2</style></issue><notes><style face="normal" font="default" size="100%">The following values have no corresponding Zotero field:&lt;br/&gt;publisher: American Chemical Society&lt;br/&gt;accession-num: 12608876</style></notes></record></records></xml>