<?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%">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></authors></contributors><titles><title><style face="normal" font="default" size="100%">Diplofuranones A and B , two further new 4-monosubstituted 2 ( 3H ) -dihydrofuranones produced by Diplodia corticola , a fungus pathogen of cork oak</style></title><secondary-title><style face="normal" font="default" size="100%">ARKIVOC</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">canker disease</style></keyword><keyword><style  face="normal" font="default" size="100%">Cork oak</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplodia corticola</style></keyword><keyword><style  face="normal" font="default" size="100%">phytotoxic metabolites</style></keyword><keyword><style  face="normal" font="default" size="100%">Quercus suber L.</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2007</style></year><pub-dates><date><style  face="normal" font="default" size="100%">2007///</style></date></pub-dates></dates><volume><style face="normal" font="default" size="100%">2007</style></volume><pages><style face="normal" font="default" size="100%">318 - 328</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Two new 4-monosubstituted 2(3H)-dihydrofuranones, named diplofuranones A and B, were isolated from liquid cultures of Diplodia corticola, a plant pathogenic fungus causing a canker disease of cork oak (Quercus suber L.). The same fungus also produces several metabolites such as the diplopyrone, the (3S,4R)-trans- and the (3R,4R)-cis-4-hydroxymellein, the sapinofuranone B and its (S,S)-enantiomer, the well known sphaeropsidins A-C, and the diplobifuranylones A and B. The diplofuranones A and B were characterised, using spectroscopic (essentially NMR and MS techniques) methods, as the 4-[(1E,3E)-5-hydroxyhexadienyl]butan-4-olide and its corresponding 3,4-dihydro side chain derivative. The stereochemistry of the stereogenic secondary hydroxylated carbon of the side chain of diplofuranone A was determined by application of Mosher’s method and proved to be R. Diplofuranone A tested at 0.2 mg mL-1 on non-host plant did not show phytotoxic activity.</style></abstract><issue><style face="normal" font="default" size="100%">vii</style></issue></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></authors></contributors><titles><title><style face="normal" font="default" size="100%">Diplofuranones A and B , two further new 4-monosubstituted 2 ( 3H ) -dihydrofuranones produced by Diplodia corticola , a fungus pathogen of cork oak</style></title><secondary-title><style face="normal" font="default" size="100%">ARKIVOC</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">canker disease</style></keyword><keyword><style  face="normal" font="default" size="100%">Cork oak</style></keyword><keyword><style  face="normal" font="default" size="100%">Diplodia corticola</style></keyword><keyword><style  face="normal" font="default" size="100%">phytotoxic metabolites</style></keyword><keyword><style  face="normal" font="default" size="100%">Quercus suber L.</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2007</style></year></dates><volume><style face="normal" font="default" size="100%">2007</style></volume><pages><style face="normal" font="default" size="100%">318-328</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Two new 4-monosubstituted 2(3H)-dihydrofuranones, named diplofuranones A and B, were isolated from liquid cultures of Diplodia corticola, a plant pathogenic fungus causing a canker disease of cork oak (Quercus suber L.). The same fungus also produces several metabolites such as the diplopyrone, the (3S,4R)-trans- and the (3R,4R)-cis-4-hydroxymellein, the sapinofuranone B and its (S,S)-enantiomer, the well known sphaeropsidins A-C, and the diplobifuranylones A and B. The diplofuranones A and B were characterised, using spectroscopic (essentially NMR and MS techniques) methods, as the 4-[(1E,3E)-5-hydroxyhexadienyl]butan-4-olide and its corresponding 3,4-dihydro side chain derivative. The stereochemistry of the stereogenic secondary hydroxylated carbon of the side chain of diplofuranone A was determined by application of Mosher’s method and proved to be R. Diplofuranone A tested at 0.2 mg mL-1 on non-host plant did not show phytotoxic activity.</style></abstract></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%">Giorgio, Egidio</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%">Evidente, Antonio</style></author><author><style face="normal" font="default" size="100%">Rosini, Carlo</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">Assignment of the Absolute Configuration of (+)-Diplopyrone, the Main Phytotoxin Produced by Diplodia mutila, the Pathogen of the Cork Oak Decline, by a Nonempirical Analysis of Its Chiroptical Properties†</style></title><secondary-title><style face="normal" font="default" size="100%">The Journal of Organic Chemistry</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">absolute configuration</style></keyword><keyword><style  face="normal" font="default" size="100%">Circular dichroism</style></keyword><keyword><style  face="normal" font="default" size="100%">DeVoe method</style></keyword><keyword><style  face="normal" font="default" size="100%">diplopyrone (voyant)</style></keyword><keyword><style  face="normal" font="default" size="100%">Mitosporic Fungi</style></keyword><keyword><style  face="normal" font="default" size="100%">Mitosporic Fungi: pathogenicity</style></keyword><keyword><style  face="normal" font="default" size="100%">Models</style></keyword><keyword><style  face="normal" font="default" size="100%">Molecular</style></keyword><keyword><style  face="normal" font="default" size="100%">Molecular Structure</style></keyword><keyword><style  face="normal" font="default" size="100%">mycotoxins</style></keyword><keyword><style  face="normal" font="default" size="100%">Mycotoxins: chemistry</style></keyword><keyword><style  face="normal" font="default" size="100%">Optical rotation</style></keyword><keyword><style  face="normal" font="default" size="100%">Plant Diseases</style></keyword><keyword><style  face="normal" font="default" size="100%">Plant Diseases: microbiology</style></keyword><keyword><style  face="normal" font="default" size="100%">Pyrones</style></keyword><keyword><style  face="normal" font="default" size="100%">Pyrones: chemistry</style></keyword><keyword><style  face="normal" font="default" size="100%">Stereoisomerism</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2004</style></year></dates><publisher><style face="normal" font="default" size="100%">American Chemical Society</style></publisher><volume><style face="normal" font="default" size="100%">70</style></volume><pages><style face="normal" font="default" size="100%">7-13</style></pages><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">The nonempirical assignment of the absolute configuration of (+)-diplopyrone, the main phytotoxin of Diplodia mutila, i.e., an endophytic fungus, widespread in Sardinian oak forests, and considered one of the main causes of cork oak decline, has been approached by two different methods:? (a) the exciton analysis of the circular dichroism (CD) spectrum and (b) the ab initio calculation of the optical rotatory power. Both methods indicate that (+)-diplopyrone is 6-[(1S)-1-hydroxyethyl]-2,4a(S),6(R),8a(S)-tetrahydropyrano[3,2-b]pyran-2-one, so the stereostructure of this important biomolecule is safely determined for the first time. A comparison of advantages and limitations of the two methods of analysis is also presented.</style></abstract><accession-num><style face="normal" font="default" size="100%">15624901</style></accession-num><notes><style face="normal" font="default" size="100%">From Duplicate 2 (Assignment of the Absolute Configuration of (+)-Diplopyrone, the Main Phytotoxin Produced by Diplodia mutila, the Pathogen of the Cork Oak Decline, by a Nonempirical Analysis of Its Chiroptical Properties† - Giorgio, Egidio; Maddau, Lucia; Spanu, Emanuela; Evidente, Antonio; Rosini, Carlo)</style></notes><research-notes><style face="normal" font="default" size="100%">From Duplicate 2 (Assignment of the Absolute Configuration of (+)-Diplopyrone, the Main Phytotoxin Produced by Diplodia mutila, the Pathogen of the Cork Oak Decline, by a Nonempirical Analysis of Its Chiroptical Properties† - Giorgio, Egidio; Maddau, Lucia; Spanu, Emanuela; Evidente, Antonio; Rosini, Carlo)</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%">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>