Oligomeric Acylphloroglucinols from Myrtle (<i>Myrtus communis</i>)

Appendino, Giovanni; Bianchi, Federica; Minassi, Alberto; Sterner, Olov; Ballero, Mauro; Gibbons, Simon

doi:10.1021/np010441b

Cited by 94 publications

(97 citation statements)

References 14 publications

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“…MC and S-MC were isolated from myrtle leaves as described previously (Appendino et al, 2002). The IBP-C was synthesized from S-MC (G. Appendino, unpublished data).…”

Section: Methodsmentioning

confidence: 99%

“…Myrtle contains a great variety of compounds like bitter substances, ethereal oil, and tannic substances (elSissi and el-Ansary, 1967). In addition to these rather ubiquitous ingredients that are present in many plants, myrtle contains unique oligomeric, nonprenylated acylphloroglucinols such as myrtucommulone (MC) and semimyrtucommulone (S-MC) (Appendino et al, 2002), which are considered to be responsible for the antioxidative (Rosa et al, 2003) …”

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confidence: 99%

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Identification of Molecular Targets of the Oligomeric Nonprenylated Acylphloroglucinols fromMyrtus communisand Their Implication as Anti-Inflammatory Compounds

Feißt

Franke²,

Appendino³

et al. 2005

J Pharmacol Exp Ther

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Myrtucommulone (MC) and semimyrtucommulone (S-MC) are unique oligomeric, nonprenylated acylphloroglucinols contained in the leaves of myrtle (Myrtus communis). Although extracts of myrtle have been traditionally used in folk medicine for the treatment of various disorders, studies addressing select cellular or molecular pharmacological properties of these extracts or specific ingredients thereof are rare. Here, we show for the first time that MC and S-MC potently suppress the biosynthesis of eicosanoids by direct inhibiting cyclooxygenase-1 and 5-lipoxygenase in vitro and in vivo at IC 50 values in the range of 1.8 to 29 M. Moreover, we show that MC and S-MC prevent the mobilization of Ca 2ϩ in polymorphonuclear leukocytes, mediated by G protein signaling pathways at IC 50 values of 0.55 and 4.5 M, respectively, and suppress the formation of reactive oxygen species and the release of elastase at comparable concentrations. The isobutyrophenone core of MC as well as S-MC was much less potent or even not active at all. In addition, MC or S-MC only partially inhibited peroxide formation or failed to block Ca 2ϩ mobilization and elastase release when polymorphonuclear leukocytes were challenged with ionomycin that circumvents G protein signaling for cell activation. We conclude that, in view of their ability to suppress typical proinflammatory cellular responses, the unique acylphloroglucinols MC and S-MC from myrtle may possess an anti-inflammatory potential, suggesting their therapeutic use for the treatment of diseases related to inflammation and allergy.Myrtle (Myrtus communis, Myrtaceae) is a Mediterranean shrub used as a culinary spice and as a folk medicine, for example, in the treatment of diabetes mellitus and as an antiseptic agent. In fact, myrtle extracts have been reported to possess antihyperglycemic (Elfellah et al., 1984;Sepici et al., 2004;Onal et al., 2005), antibacterial (Al-Saimary et al., 2002;Bonjar, 2004), and analgesic (Levesque and Lafont, 2000) properties. Recent reports have described antioxidant activities of different extracts of myrtle and certain ingredients thereof (Rosa et al., 2003;Hayder et al., 2004;Romani et al., 2004), implying potential as medicine for the treatment of diseases related to oxidative stress, including inflammatory disorders. Myrtle contains a great variety of compounds like bitter substances, ethereal oil, and tannic substances (elSissi and el-Ansary, 1967). In addition to these rather ubiquitous ingredients that are present in many plants, myrtle contains unique oligomeric, nonprenylated acylphloroglucinols such as myrtucommulone (MC) and semimyrtucommulone (S-MC) (Appendino et al., 2002), which are considered to be responsible for the antioxidative (Rosa et al., 2003)

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“…MC and S-MC were isolated from myrtle leaves as described previously (Appendino et al, 2002). The IBP-C was synthesized from S-MC (G. Appendino, unpublished data).…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Identification of Molecular Targets of the Oligomeric Nonprenylated Acylphloroglucinols fromMyrtus communisand Their Implication as Anti-Inflammatory Compounds

Feißt

Franke²,

Appendino³

et al. 2005

J Pharmacol Exp Ther

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“…Each chemotype can be further divided into two subgroups, according to the relative ratio of α-pinene to myrtenyl acetate or α-pinene to cineole. Myrtle contains unique oligomeric, non-prenylated acylphloroglucinols such as myrtucommulone (MC) and semimyrtucommulone (S-MC) (8). MC contained in the leaves of M. communis has been reported to suppress the biosynthesis of eicosanoids by inhibition of 5-lipoxygenase and cyclooxygenase-1 in vitro and to inhibit the release of elastase and the formation of reactive oxygen species in activated polymorphonuclear leukocytes (6).…”

Section: Introductionmentioning

confidence: 99%

Chemical composition and antibacterial activitiy of the essential oils of AlgerianMyrtus communisL.

Hennia

Brada

Nemmiche

et al. 2015

Journal of Essential Oil Research

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Myrtus communis L. leaf essential oils from Algeria were analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). A total of thirty-four components were identified accounting for 95% of the oil. The main compounds were limonene (23.4%), linalool (15.4%), geranyl acetate (10.9%), α-pinene (10.7%), linalyl acetate (8.2%) and 1,8-cineole (6.6%).The antimicrobial evaluation showed that myrtle oil exhibited good antibacterial activity against Staphylococcus aureus, Proteus mirabilis and Kleibsiella pneumonia, but differed according to the strains. Conversely, it was not active against Pseudomonas aeruginosa.

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“…Myrtle (Myrtus communis L., Myrtaceae) is widely distributed in the Mediterranean area and is used as a culinary spice and an antiseptic and anti-inflammatory agent in folk medicine (Appendino et al, 2002). Nevertheless, only a small number of studies have investigated the pharmacological effects of the plant or its specific ingredients.…”

mentioning

confidence: 99%

“…Myrtucommulone (MC) and semimyrtucommulone are unique oligomeric, nonprenylated acylphloroglucinols contained in the leaves of myrtle. In particular, they are considered to be responsible for the antioxidative (Rosa et al, 2003) and the antibacterial (Rotstein et al, 1974;Appendino et al, 2002) activities of myrtle preparations. Moreover, MC potently suppresses the biosynthesis of eicosanoids by inhibition of 5-lipoxygenase and cyclooxygenase-1, and it inhibits the release of elastase and the formation of ROS, apparently by blocking receptor-coupled Ca 2ϩ mobilization (Feisst et al, 2005).…”

mentioning

confidence: 99%

Myrtucommulone from Myrtus communis Exhibits Potent Anti-Inflammatory Effectiveness in Vivo

Rossi

Paola²,

Mazzon

et al. 2008

J Pharmacol Exp Ther

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Myrtucommulone (MC), a nonprenylated acylphloroglucinol contained in the leaves of myrtle (Myrtus communis), has been reported to suppress the biosynthesis of eicosanoids by inhibition of 5-lipoxygenase and cyclooxygenase-1 in vitro and to inhibit the release of elastase and the formation of reactive oxygen species in activated polymorphonuclear leukocytes. Here, in view of the ability of MC to suppress typical proinflammatory cellular responses in vitro, we have investigated the effects of MC in in vivo models of inflammation. MC was administered to mice intraperitoneally, and paw edema and pleurisy were induced by the subplantar and intrapleural injection of carrageenan, respectively. MC (0.5, 1.5, and 4.5 mg/kg i.p.) reduced the development of mouse carrageenan-induced paw edema in a dose-dependent manner. Moreover, MC (4.5 mg/kg i.p. 30 min before and after carrageenan) exerted anti-inflammatory effects in the pleurisy model. In particular, 4 h after carrageenan injection in the pleurisy model, MC reduced: 1) the exudate volume and leukocyte numbers; 2) lung injury (histological analysis) and neutrophil infiltration (myeloperoxidase activity); 3) the lung intercellular adhesion molecule-1 and P-selectin immunohistochemical localization; 4) the cytokine levels (tumor necrosis factor-␣ and interleukin-1␤) in the pleural exudate and their immunohistochemical localization in the lung; 5) the leukotriene B 4 , but not prostaglandin E 2 , levels in the pleural exudates; and 6) lung peroxidation (thiobarbituric acid-reactant substance) and nitrotyrosine and poly (ADP-ribose) immunostaining. In conclusion, our results demonstrate that MC exerts potent anti-inflammatory effects in vivo and offer a novel therapeutic approach for the management of acute inflammation.

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Oligomeric Acylphloroglucinols from Myrtle (Myrtus communis)

Cited by 94 publications

References 14 publications

Identification of Molecular Targets of the Oligomeric Nonprenylated Acylphloroglucinols fromMyrtus communisand Their Implication as Anti-Inflammatory Compounds

Identification of Molecular Targets of the Oligomeric Nonprenylated Acylphloroglucinols fromMyrtus communisand Their Implication as Anti-Inflammatory Compounds

Chemical composition and antibacterial activitiy of the essential oils of AlgerianMyrtus communisL.

Myrtucommulone from Myrtus communis Exhibits Potent Anti-Inflammatory Effectiveness in Vivo

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