Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> Species

Myrtaceae family is a continuous source of antimicrobial agents. In the search for novel antimicrobial agents against <i>Staphylococcus</i> species, bioactive fractions of <i>Myrtus communis</i> L., growing in the Sardinia island (Italy) have been investigated. Their phytoche...

Full description

Bibliographic Details
Main Authors: Francesca Guzzo, Alexandra G. Durán, Cinzia Sanna, Rosangela Marasco, Nicola Molfetta, Elisabetta Buommino, Antonio Fiorentino, Brigida D’Abrosca
Format: Article
Language:English
Published: MDPI AG 2022-10-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/27/20/7109
_version_ 1827648639202230272
author Francesca Guzzo
Alexandra G. Durán
Cinzia Sanna
Rosangela Marasco
Nicola Molfetta
Elisabetta Buommino
Antonio Fiorentino
Brigida D’Abrosca
author_facet Francesca Guzzo
Alexandra G. Durán
Cinzia Sanna
Rosangela Marasco
Nicola Molfetta
Elisabetta Buommino
Antonio Fiorentino
Brigida D’Abrosca
author_sort Francesca Guzzo
collection DOAJ
description Myrtaceae family is a continuous source of antimicrobial agents. In the search for novel antimicrobial agents against <i>Staphylococcus</i> species, bioactive fractions of <i>Myrtus communis</i> L., growing in the Sardinia island (Italy) have been investigated. Their phytochemical analysis led us to isolate and characterize four alkylphloroglucinol glycosides (<b>1</b>–<b>4</b>), three of them gallomyrtucommulones G–H (<b>1</b>,<b>2</b>), and myrtucommulonoside (<b>4</b>) isolated and characterized for the first time. The structures of the new and known compounds, endopreroxide G3 (<b>5</b>), myricetin-3-<i>O</i>-glycosides (<b>6</b>,<b>7</b>) were determined based on the spectroscopic evidence including 1D-/2D-NMR and HR-MS spectrometry. Enriched fractions as well as pure compounds were tested for their antimicrobial activity by broth micro-dilution assay against <i>Staphylococcus epidermidis</i> and <i>S. aureus.</i> Results reported herein demonstrated that gallomyrtucommulone G (<b>1</b>) showed a selective antimicrobial activity against both <i>S. aureus</i> strains (ATCC 29213 and 43300) until 16 μg/mL while gallomyrtucommulone D (<b>3</b>) showed the best growth inhibition value at 64 μg/mL.
first_indexed 2024-03-09T19:41:59Z
format Article
id doaj.art-fd6459cb080741f0b07782c7a661760d
institution Directory Open Access Journal
issn 1420-3049
language English
last_indexed 2024-03-09T19:41:59Z
publishDate 2022-10-01
publisher MDPI AG
record_format Article
series Molecules
spelling doaj.art-fd6459cb080741f0b07782c7a661760d2023-11-24T01:37:34ZengMDPI AGMolecules1420-30492022-10-012720710910.3390/molecules27207109Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> SpeciesFrancesca Guzzo0Alexandra G. Durán1Cinzia Sanna2Rosangela Marasco3Nicola Molfetta4Elisabetta Buommino5Antonio Fiorentino6Brigida D’Abrosca7Dipartimento di Scienze e Tecnologie Ambientali Biologiche e Farmaceutiche–DiSTABiF, Università degli Studi della Campania “Luigi Vanvitelli”, Via Vivaldi 43, 81100 Caserta, ItalyAllelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), School of Science, University of Cadiz, Campus de Excelencia Internacional (ceiA3), C/ República Saharaui n° 7, 11510 Puerto Real, SpainDepartment of Life and Environmental Sciences, University of Cagliari, Via Sant’Ignazio da Laconi 13, 09123 Cagliari, ItalyDipartimento di Scienze e Tecnologie Ambientali Biologiche e Farmaceutiche–DiSTABiF, Università degli Studi della Campania “Luigi Vanvitelli”, Via Vivaldi 43, 81100 Caserta, ItalyDipartimento di Farmacia, Università degli Studi di Napoli “Federico II”, Via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli “Federico II”, Via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Scienze e Tecnologie Ambientali Biologiche e Farmaceutiche–DiSTABiF, Università degli Studi della Campania “Luigi Vanvitelli”, Via Vivaldi 43, 81100 Caserta, ItalyDipartimento di Scienze e Tecnologie Ambientali Biologiche e Farmaceutiche–DiSTABiF, Università degli Studi della Campania “Luigi Vanvitelli”, Via Vivaldi 43, 81100 Caserta, ItalyMyrtaceae family is a continuous source of antimicrobial agents. In the search for novel antimicrobial agents against <i>Staphylococcus</i> species, bioactive fractions of <i>Myrtus communis</i> L., growing in the Sardinia island (Italy) have been investigated. Their phytochemical analysis led us to isolate and characterize four alkylphloroglucinol glycosides (<b>1</b>–<b>4</b>), three of them gallomyrtucommulones G–H (<b>1</b>,<b>2</b>), and myrtucommulonoside (<b>4</b>) isolated and characterized for the first time. The structures of the new and known compounds, endopreroxide G3 (<b>5</b>), myricetin-3-<i>O</i>-glycosides (<b>6</b>,<b>7</b>) were determined based on the spectroscopic evidence including 1D-/2D-NMR and HR-MS spectrometry. Enriched fractions as well as pure compounds were tested for their antimicrobial activity by broth micro-dilution assay against <i>Staphylococcus epidermidis</i> and <i>S. aureus.</i> Results reported herein demonstrated that gallomyrtucommulone G (<b>1</b>) showed a selective antimicrobial activity against both <i>S. aureus</i> strains (ATCC 29213 and 43300) until 16 μg/mL while gallomyrtucommulone D (<b>3</b>) showed the best growth inhibition value at 64 μg/mL.https://www.mdpi.com/1420-3049/27/20/7109<i>Myrtus communis</i>gallomyrtucommulonestructural elucidationNMR analysisantimicrobial assay<i>Staphylococcus epidermidis</i>
spellingShingle Francesca Guzzo
Alexandra G. Durán
Cinzia Sanna
Rosangela Marasco
Nicola Molfetta
Elisabetta Buommino
Antonio Fiorentino
Brigida D’Abrosca
Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> Species
Molecules
<i>Myrtus communis</i>
gallomyrtucommulone
structural elucidation
NMR analysis
antimicrobial assay
<i>Staphylococcus epidermidis</i>
title Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> Species
title_full Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> Species
title_fullStr Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> Species
title_full_unstemmed Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> Species
title_short Gallomyrtucommulones G and H, New Phloroglucinol Glycosides, from Bioactive Fractions of <i>Myrtus communis</i> against <i>Staphylococcus</i> Species
title_sort gallomyrtucommulones g and h new phloroglucinol glycosides from bioactive fractions of i myrtus communis i against i staphylococcus i species
topic <i>Myrtus communis</i>
gallomyrtucommulone
structural elucidation
NMR analysis
antimicrobial assay
<i>Staphylococcus epidermidis</i>
url https://www.mdpi.com/1420-3049/27/20/7109
work_keys_str_mv AT francescaguzzo gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies
AT alexandragduran gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies
AT cinziasanna gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies
AT rosangelamarasco gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies
AT nicolamolfetta gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies
AT elisabettabuommino gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies
AT antoniofiorentino gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies
AT brigidadabrosca gallomyrtucommulonesgandhnewphloroglucinolglycosidesfrombioactivefractionsofimyrtuscommunisiagainstistaphylococcusispecies