Cytotoxic Phloroglucinols from the Leaves of <i>Myrtus communis</i>

Cottiglia, Filippo; Casu, Laura; Leonti, Marco; Caboni, Pierluigi; Floris, C.; Busonera, Bernardetta; Farci, P; Ouhtit, Aicha; Sanna, Giuseppina

doi:10.1021/np2009219

Cited by 58 publications

(47 citation statements)

References 18 publications

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“…Leaves have been used as a folk remedy to treat hypertension, hyperglycaemia, haemorrhoids, cold, diaorrhea, internal diseases, rheumatic pain, to pass kidney stones and wounds (Mine et al ., ), among others. In recent years this plant has received increasing attention for its biological properties, such as anti‐oxidant (Romani et al ., ; Aidi Wannes et al ., ), anti‐nociceptive, anti‐inflammatory (Hosseinzadeh et al ., ), cytotoxic and anti‐bacterial (Cottiglia et al ., ; Messaoud et al ., ) activities. The berries have also been studied for the characterisation of the phenolic composition (Barboni et al ., ), stability and anti‐oxidant activity (Montoro et al ., ).…”

Section: Introductionmentioning

confidence: 98%

UPLC–QTOF/MS for a Rapid Characterisation of Phenolic Compounds from Leaves of Myrtus communis L.

Taamalli

Iswaldi

Arráez‐Román

et al. 2013

Phytochemical Analysis

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Section: Introductionmentioning

confidence: 98%

UPLC–QTOF/MS for a Rapid Characterisation of Phenolic Compounds from Leaves of Myrtus communis L.

Taamalli

Iswaldi

Arráez‐Román

et al. 2013

Phytochemical Analysis

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“…These results were subsequently confirmed by other authors. [26,27] Several tannins (oenothein B, eugeniflorin D2, tellimagrandin I and II) [28] and phloroglucinols [29] are also reported to be present in myrtle leaves.…”

Section: Introductionmentioning

confidence: 99%

A Two‐Year Bio‐Agronomic and Chemotaxonomic Evaluation of Wild Sicilian Myrtle (Myrtus communis L.) Berries and Leaves

Siracusa

Napoli

Tuttolomondo

et al. 2019

Chemistry & Biodiversity

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A collection of nine Myrtus communis samples from different localities of Sicily was evaluated. Morphological traits and production characteristics have been chosen as parameters to arrange the samples into homogeneous groups and to identify the best biotypes for possible future agro‐industrial exploitation. The plant material has been subjected to taxonomic characterization from biometric and phytochemical perspectives. Myrtle berries and leaves have been analyzed for their content in metabolites, applying a cascade extraction protocol for M. communis leaves and a single hydroalcoholic extraction for berries, whereas hydrodistillation procedures have been applied to obtain the essential oils from berries and leaves. The analyses of non‐volatile components were carried out by LC‐UV‐DAD‐ESI‐MS. All the extracts were characterized by the presence of numerous polyphenols, namely highly hydroxylated flavonols such as quercetin and myricetin; and ellagic acid detected in all samples. In addition, myrtle berries contained nine different anthocyanins, namely delphinidin, petunidin, cyanidin and malvidin derivatives. The essential oils (EOs) were analyzed by a combination of GC‐FID and GC/MS. A total of 33 and 34 components were fully characterized with the predominance of α‐pinene, myrtenyl acetate, linalool, 1,8‐cineole and linalyl acetate. All phytochemical profiles were subjected to cluster analyses, which allowed subdividing the myrtle samples in different chemical groups.

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“…This explains why pharmacological activities of the synthesized compounds 13 are similar to those of the isolated natural products. This poses the question of whether the other myrtucommulones 5,7,8 are enantiomerically pure and, if so, how these compounds are biosynthesized. In view of the results of Nicoletti et al, 9 it seems that myrtle and its endophytic fungus both produce MC A and other myrtucommulones.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Stereoisomeric Composition of Natural Myrtucommulone A

et al. 2015

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Myrtucommulone A (MC A) (1), isolated from Myrtus communis (myrtle), shows the same pharmacological activity for inhibition of inflammation and induction of apoptosis as synthetic MC A, which consists of three stereoisomers, i.e., two enantiomers and one meso form. This led to the question of whether the natural MC A is a pure stereoisomer or a mixture of stereoisomers. The specific rotation and electronic circular dichroism (ECD) data of natural MC A (1) as well as of a pentacyclic derivative 4 revealed that naturally occurring MC A (1) consists of the racemate and the meso form in a 1:1 ratio. A probable precursor of MC A (1), nor-semimyrtucommulone (5), was also isolated from myrtle as a racemate. The absolute configurations of the enantiomers of 1 and 5 were determined using a combination of experimental and quantum-chemical calculated ECD spectra.

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Cytotoxic Phloroglucinols from the Leaves of Myrtus communis

Cited by 58 publications

References 18 publications

UPLC–QTOF/MS for a Rapid Characterisation of Phenolic Compounds from Leaves of Myrtus communis L.

UPLC–QTOF/MS for a Rapid Characterisation of Phenolic Compounds from Leaves of Myrtus communis L.

A Two‐Year Bio‐Agronomic and Chemotaxonomic Evaluation of Wild Sicilian Myrtle (Myrtus communis L.) Berries and Leaves

Stereoisomeric Composition of Natural Myrtucommulone A

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