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Antimicrobial Phenolics and Unusual Glycerides from Helichrysum italicum subsp. microphyllum

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† Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, Via Montesano 49, 80131 Napoli, Italy
‡ Dipartimento di Scienze Farmaceutiche, Università del Piemonte Orientale, Via Bovio 6, 28100, Novara, Italy
§ Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, 29-39 Brunswick Square, London WC1N 1AX, U.K.
⊥ Dipartimento di Scienze Botaniche and Consorzio per lo Studio dei Metaboliti Secondari (COSMESE), Università di Cagliari, Viale S. Ignazio 13, 09123 Cagliari, Italy
*Tel: + 39 081 678509 (O.T.-S.); +39 0321 373744 (G.A.). Fax: + 39 081 678552 (O.T.-S.); +39 0321 0.375621 (G.A.). E-mail: [email protected] (O.T.-S.); [email protected] (G.A.).
Cite this: J. Nat. Prod. 2013, 76, 3, 346–353
Publication Date (Web):December 24, 2012
https://doi.org/10.1021/np3007149
Copyright © 2012 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    During a large-scale isolation campaign for the heterodimeric phloroglucinyl pyrone arzanol (1a) from Helichrysum italicum subsp. microphyllum, several new phenolics as well as an unusual class of lipids named santinols (5a–c, 6–8) have been characterized. Santinols are angeloylated glycerides characterized by the presence of branched acyl- or keto-acyl chains and represent a hitherto unreported class of plant lipids. The antibacterial activity of arzanol and of a selection of Helichrysum phenolics that includes coumarates, benzofurans, pyrones, and heterodimeric phloroglucinols was evaluated, showing that only the heterodimers showed potent antibacterial action against multidrug-resistant Staphylococcus aureus isolates. These observations validate the topical use of Helichrysum extracts to prevent wound infections, a practice firmly established in the traditional medicine of the Mediterranean area.

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