Phloroglucinols from Myrtaceae: attractive targets for structural characterization, biological properties and synthetic
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Phloroglucinols from Myrtaceae: attractive targets for structural characterization, biological properties and synthetic procedures Odeta Celaj . Alexandra G. Dura´n . Pasqualina Cennamo . Monica Scognamiglio . Antonio Fiorentino . Assunta Esposito . Brigida D’Abrosca
Received: 31 January 2020 / Accepted: 5 June 2020 Ó Springer Nature B.V. 2020
Abstract Myrtaceae Juss. is a very large family of flowering plants, that are a valuable source of bioactive compounds. From the phytochemical point of view, apart from ubiquitous tannins, flavonoid derivatives and volatile oils, Myrtaceae plants are very rich in phloroglucinol derivatives, divided in two principal subclasses: oligomeric acylphloroglucinols and phloroglucinol-terpene adducts. Despite this large structural variability, many studies on phloroglucinols from the Myrtaceae have focused on unique bioactive acylphloroglucinol compounds, named
The last two authors (Assunta Esposito and Brigida D’Abrosca) contributed equally to this work. O. Celaj P. Cennamo M. Scognamiglio A. Fiorentino A. Esposito B. D’Abrosca (&) Dipartimento di Scienze e Tecnologie Ambientali Biologiche e Farmaceutiche –DiSTABiF, Universita` degli Studi della Campania ‘‘Luigi Vanvitelli’’, Via Vivaldi 43, 81100 Caserta, Italy e-mail: [email protected] A. G. Dura´n Allelopathy Group, Department of Organic Chemistry, Institute of Biomolecules (INBIO), Campus de Excelencia Internacional (ceiA3), School of Science, University of Cadiz, C/Repu´blica Saharaui n8 7, 11510 Puerto Real, Cadiz, Spain A. Fiorentino B. D’Abrosca Dipartimento di Biotecnologia Marina, Stazione Zoologica Anton Dohrn, Villa Comunale, 80121 Naples, Italy
myrtucommulones. Nevertheless, many studies also reported other interesting phloroglucinol derivatives. Therefore, in this review, a comprehensive description of the chemical features of acylphloroglucinols and meroterpenoid-acylphloroglucinols from the Myrtaceae family is presented along with their biological activities. Moreover, since myrtucommulones and their derivatives have become attractive targets for organic chemists, thanks to their structural features and biological activities, relevant approaches and synthetic procedures are herewith discussed. Keywords Antimicrobial-activity Myrtaceae Phloroglucinols Terpene-adduct Myrtucommulones
Introduction Plants belonging to the Myrtaceae family have been used in traditional medicine and as food or spices since ancient times. They are indeed an invaluable source of bioactive metabolites, including ubiquitous tannins, flavonoid derivatives, volatile oils, etc. However, Myrtaceae plants are also a very rich source of phloroglucinol derivatives. Phloroglucinols are a major class of natural compounds widely occurring in biological systems: they are synthesized and accumulated by plants from different families, as well as by microorganisms and
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marine organisms (Singh and Bharate 2006). The simple phloroglucinol unit (1,3,5-trihy
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