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A syn-ent-labdadiene derivative with a rare spiro-β-lactone function from the male cones of Wollemia nobilis.

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Title: A syn-ent-labdadiene derivative with a rare spiro-β-lactone function from the male cones of Wollemia nobilis.
Authors: Venditti, Alessandro1 alessandro.venditti@uniroma1.italessandro.venditti@gmail.com, Frezza, Claudio2, Vincenti, Flaminia1, Brodella, Antonia1, Sciubba, Fabio1, Montesano, Camilla1, Franceschin, Marco1, Sergi, Manuel3, Foddai, Sebastiano2, Di Cocco, Maria Enrica1, Curini, Roberta1, Delfini, Maurizio1, Bianco, Armandodoriano1, Serafini, Mauro2
Source: Phytochemistry. Feb2019, Vol. 158, p91-95. 5p.
Subjects: Wollemia nobilis, Diterpenes, Ethanol, Plant species, Phytochemicals, High performance liquid chromatography
Abstract: Abstract An undescribed labdane-like diterpene with a rare spiro-β-lactone function was identified from the ethanol extract of the male cones of the coniferous tree Wollemia nobilis. This spirolabdadienolide (IUPAC name: syn - ent -8(17),13-labdadien-19,18-olid-15-oic acid methyl ester; trivial name: wollemolide), was isolated by means of traditional and high performance chromatography techniques and structurally elucidated through NMR and MS. In addition, six further known metabolites were evidenced in the extract. Wollemolide, which may be considered an additional chemotaxonomic marker, and 4′- O -methyl-scutellarein, a simple flavonoid, had not been isolated in our previous phytochemical study on the same plant organ. This demonstrates how the molecular pattern of a plant species is in continuous movement and changes with the passing of time according to the climate of the year. Graphical abstract Image 1 Highlights • A reassessment of Wollemia nobilis male cones was carried out. • An undescribed syn - ent -labdadiene derivative was isolated. • A seasonal variability of metabolites was observed. • This is the first report on the presence of simple flavonoids in W. nobilis. • The chemosystematic relevance of isolated compounds was discussed. [ABSTRACT FROM AUTHOR]
Copyright of Phytochemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 134049001
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  Data: A syn-ent-labdadiene derivative with a rare spiro-β-lactone function from the male cones of Wollemia nobilis.
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  Data: <searchLink fieldCode="AR" term="%22Venditti%2C+Alessandro%22">Venditti, Alessandro</searchLink><relatesTo>1</relatesTo><i> alessandro.venditti@uniroma1.italessandro.venditti@gmail.com</i><br /><searchLink fieldCode="AR" term="%22Frezza%2C+Claudio%22">Frezza, Claudio</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Vincenti%2C+Flaminia%22">Vincenti, Flaminia</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Brodella%2C+Antonia%22">Brodella, Antonia</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Sciubba%2C+Fabio%22">Sciubba, Fabio</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Montesano%2C+Camilla%22">Montesano, Camilla</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Franceschin%2C+Marco%22">Franceschin, Marco</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Sergi%2C+Manuel%22">Sergi, Manuel</searchLink><relatesTo>3</relatesTo><br /><searchLink fieldCode="AR" term="%22Foddai%2C+Sebastiano%22">Foddai, Sebastiano</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Di+Cocco%2C+Maria+Enrica%22">Di Cocco, Maria Enrica</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Curini%2C+Roberta%22">Curini, Roberta</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Delfini%2C+Maurizio%22">Delfini, Maurizio</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Bianco%2C+Armandodoriano%22">Bianco, Armandodoriano</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Serafini%2C+Mauro%22">Serafini, Mauro</searchLink><relatesTo>2</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Phytochemistry%22">Phytochemistry</searchLink>. Feb2019, Vol. 158, p91-95. 5p.
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  Data: <searchLink fieldCode="DE" term="%22Wollemia+nobilis%22">Wollemia nobilis</searchLink><br /><searchLink fieldCode="DE" term="%22Diterpenes%22">Diterpenes</searchLink><br /><searchLink fieldCode="DE" term="%22Ethanol%22">Ethanol</searchLink><br /><searchLink fieldCode="DE" term="%22Plant+species%22">Plant species</searchLink><br /><searchLink fieldCode="DE" term="%22Phytochemicals%22">Phytochemicals</searchLink><br /><searchLink fieldCode="DE" term="%22High+performance+liquid+chromatography%22">High performance liquid chromatography</searchLink>
– Name: Abstract
  Label: Abstract
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  Data: Abstract An undescribed labdane-like diterpene with a rare spiro-β-lactone function was identified from the ethanol extract of the male cones of the coniferous tree Wollemia nobilis. This spirolabdadienolide (IUPAC name: syn - ent -8(17),13-labdadien-19,18-olid-15-oic acid methyl ester; trivial name: wollemolide), was isolated by means of traditional and high performance chromatography techniques and structurally elucidated through NMR and MS. In addition, six further known metabolites were evidenced in the extract. Wollemolide, which may be considered an additional chemotaxonomic marker, and 4′- O -methyl-scutellarein, a simple flavonoid, had not been isolated in our previous phytochemical study on the same plant organ. This demonstrates how the molecular pattern of a plant species is in continuous movement and changes with the passing of time according to the climate of the year. Graphical abstract Image 1 Highlights • A reassessment of Wollemia nobilis male cones was carried out. • An undescribed syn - ent -labdadiene derivative was isolated. • A seasonal variability of metabolites was observed. • This is the first report on the presence of simple flavonoids in W. nobilis. • The chemosystematic relevance of isolated compounds was discussed. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Phytochemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.phytochem.2018.11.012
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      – Code: eng
        Text: English
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      – SubjectFull: Wollemia nobilis
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      – SubjectFull: Diterpenes
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      – SubjectFull: Ethanol
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      – SubjectFull: Plant species
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      – SubjectFull: Phytochemicals
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      – SubjectFull: High performance liquid chromatography
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              Text: Feb2019
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