The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> Metabolites
9-Hydroxynerolidol, 9-oxonerolidol, and chiliadenol B are three farnesane-type sesquiterpenoids isolated from <i>Chiliadenus lopadusanus</i> that have shown an interesting activity against human pathogens as Gram+ and Gram− bacteria resistant to antibiotics. However, the absolute configu...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-12-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/11/12/1902 |
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| author | Giuseppe Mazzeo Alessio Cimmino Giovanna Longhi Marco Masi Antonio Evidente Sergio Abbate |
| author_facet | Giuseppe Mazzeo Alessio Cimmino Giovanna Longhi Marco Masi Antonio Evidente Sergio Abbate |
| author_sort | Giuseppe Mazzeo |
| collection | DOAJ |
| description | 9-Hydroxynerolidol, 9-oxonerolidol, and chiliadenol B are three farnesane-type sesquiterpenoids isolated from <i>Chiliadenus lopadusanus</i> that have shown an interesting activity against human pathogens as Gram+ and Gram− bacteria resistant to antibiotics. However, the absolute configuration (AC) of these interesting sesquiterpenes has not been assigned so far. Vibrational and electronic circular dichroism spectra have been recorded and correlations are pointed out for the three compounds. Density functional theory (DFT) calculations are used in conjunction with Mosher’s method of investigation to assign AC. Statistical analysis is considered to quantitatively define the choice of AC from VCD spectra. |
| first_indexed | 2024-03-10T04:32:52Z |
| format | Article |
| id | doaj.art-87213d86517e4acd8c72e7d92518b59c |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-03-10T04:32:52Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-87213d86517e4acd8c72e7d92518b59c2023-11-23T04:01:01ZengMDPI AGBiomolecules2218-273X2021-12-011112190210.3390/biom11121902The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> MetabolitesGiuseppe Mazzeo0Alessio Cimmino1Giovanna Longhi2Marco Masi3Antonio Evidente4Sergio Abbate5Dipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123 Brescia, ItalyDipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte Sant’Angelo, 80126 Napoli, ItalyDipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123 Brescia, ItalyDipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte Sant’Angelo, 80126 Napoli, ItalyDipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte Sant’Angelo, 80126 Napoli, ItalyDipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123 Brescia, Italy9-Hydroxynerolidol, 9-oxonerolidol, and chiliadenol B are three farnesane-type sesquiterpenoids isolated from <i>Chiliadenus lopadusanus</i> that have shown an interesting activity against human pathogens as Gram+ and Gram− bacteria resistant to antibiotics. However, the absolute configuration (AC) of these interesting sesquiterpenes has not been assigned so far. Vibrational and electronic circular dichroism spectra have been recorded and correlations are pointed out for the three compounds. Density functional theory (DFT) calculations are used in conjunction with Mosher’s method of investigation to assign AC. Statistical analysis is considered to quantitatively define the choice of AC from VCD spectra.https://www.mdpi.com/2218-273X/11/12/1902<i>Chiliadenus lopadusanus</i>farnesane-type sesquiterpenes9-hydroxynerolidol9-oxonerolidol and chiliadenol BVCDECD |
| spellingShingle | Giuseppe Mazzeo Alessio Cimmino Giovanna Longhi Marco Masi Antonio Evidente Sergio Abbate The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> Metabolites Biomolecules <i>Chiliadenus lopadusanus</i> farnesane-type sesquiterpenes 9-hydroxynerolidol 9-oxonerolidol and chiliadenol B VCD ECD |
| title | The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> Metabolites |
| title_full | The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> Metabolites |
| title_fullStr | The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> Metabolites |
| title_full_unstemmed | The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> Metabolites |
| title_short | The Assignment of the Absolute Configuration of Non-Cyclic Sesquiterpenes by Vibrational and Electronic Circular Dichroism: The Example of <i>Chiliadenus lopadusanus</i> Metabolites |
| title_sort | assignment of the absolute configuration of non cyclic sesquiterpenes by vibrational and electronic circular dichroism the example of i chiliadenus lopadusanus i metabolites |
| topic | <i>Chiliadenus lopadusanus</i> farnesane-type sesquiterpenes 9-hydroxynerolidol 9-oxonerolidol and chiliadenol B VCD ECD |
| url | https://www.mdpi.com/2218-273X/11/12/1902 |
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