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Concept: Helichrysum italicum

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Helichrysum italicum (Roth) G. Don fil. (family Asteraceae) has been used for its medicinal properties for a long time and, even nowadays, continues to play an important role in the traditional medicine of Mediterranean countries. Based on this traditional knowledge, its different pharmacological activities have been the focus of active research.

Concepts: Alternative medicine, Scientific method, Ayurveda, Helichrysum, Data, Medicine, Asteraceae, Helichrysum italicum

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Six medicinal plants Helichrysum italicum (Roth) G. Don, Angelica archangelica L., Lavandula officinalis L., Salvia officinalis L., Melilotus officinalis L., and Ruta graveolens L. were used. The aim of the study was to compare their extracts obtained by Soxhlet (hexane) extraction, maceration with ethanol (EtOH), and supercritical CO₂ extraction (SC-CO₂) targeted on coumarin content (by high performance liquid chromatography with ultraviolet detection, HPLC-UV), 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging capacity, and total phenols (TPs) content (by Folin-Ciocalteu assay). The highest extraction yields were obtained by EtOH, followed by hexane and SC-CO₂. The highest coumarin content (316.37 mg/100 g) was found in M. officinalis EtOH extracts, but its SC-CO₂ extraction yield was very low for further investigation. Coumarin was also found in SC-CO₂ extracts of S. officinalis, R. graveolens, A. archangelica, and L. officinalis. EtOH extracts of all plants exhibited the highest DPPH scavenging capacity. SC-CO₂ extracts exhibited antiradical capacity similar to hexane extracts, while S. officinalis SC-CO₂ extracts were the most potent (95.7%). EtOH extracts contained the most TPs (up to 132.1 mg gallic acid equivalents (GAE)/g from H. italicum) in comparison to hexane or SC-CO₂ extracts. TPs content was highly correlated to the DPPH scavenging capacity of the extracts. The results indicate that for comprehensive screening of different medicinal plants, various extraction techniques should be used in order to get a better insight into their components content or antiradical capacity.

Concepts: Salvia officinalis, Garden Angelica, Helichrysum italicum, Herbs, Lavender, High performance liquid chromatography, Gallic acid, Medicinal plants

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Three unusual amino-phloroglucinols, named helichrytalicines A-C, along with seventeen known compounds including acetophenones, tremetrone derivatives, low-molecular weight phenols, flavonol glucosides, have been isolated from the medium-polar extract of Helichrysum italicum (Roth) G. Don, a medicinal plant typical of the Mediterranean vegetation. The structures of the compounds have been elucidated based on extensive 2D-NMR spectroscopic analyses, including COSY, TOCSY, HSQC, CIGAR-HMBC, H2BC and HSQC-TOCSY, along with Q-TOF HRMS(2) analysis. Stereostructure of the new compounds has been elucidated by Mosher’s method and NOESY experiment. Antimicrobial properties against Staphylococcus epidermidis of selected compounds have been evaluated.

Concepts: Nuclear magnetic resonance, Biome, Exclusive correlation spectroscopy, Staphylococcus epidermidis, Helichrysum italicum, Correlation spectroscopy, Spectroscopy, Two dimensional correlation analysis

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The species of Helichrysum sect. Stoechadina (Asteraceae) are well-known for their secondary metabolite content and the characteristic aromatic bouquets. In the wild, populations exhibit a wide phenotypic plasticity which makes critical the circumscription of species and infraspecific ranks. Previous investigations on Helichrysum italicum complex focused on a possible phytochemical typification based on hydrodistilled essential oils. Aims of this paper are three-fold: (i) characterizing the volatile profiles of different populations, testing (ii) how these profiles vary across populations and (iii) how the phytochemical diversity may contribute in solving taxonomic problems. Nine selected Helichrysum populations, included within the H. italicum complex, Helichrysum litoreum and Helichrysum stoechas, were investigated. H. stoechas was chosen as outgroup for validating the method. After collection in the wild, plants were cultivated in standard growing conditions for over one year. Annual leafy shoots were screened in the post-blooming period for the emissions of volatile organic compounds (VOCs) by means of headspace solid phase microextraction coupled with gas-chromatography and mass spectrometry (HS-SPME-GC/MS). The VOC composition analysis revealed the production of overall 386 different compounds, with terpenes being the most represented compound class. Statistical data processing allowed the identification of the indicator compounds that differentiate the single populations, revealing the influence of the geographical provenance area in determining the volatile profiles. These results suggested the potential use of VOCs as valuable diacritical characters in discriminating the Helichrysum populations. In addition, the cross-validation analysis hinted the potentiality of this volatolomic study in the discrimination of the Helichrysum species and subspecies, highlighting a general congruence with the current taxonomic treatment of the genus. The consistency between this phytochemical approach and the traditional morphometrical analysis in studying the Helichrysum populations supports the validity of the VOC profile in solving taxonomic problems.

Concepts: Subspecies, Organic compounds, Taxonomic rank, Volatile, Helichrysum italicum, Species, Helichrysum, Volatile organic compound

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The increasing popularity of immortelle (Helichrysum italicum (Roth) G. Don) and its products, particularly in the cosmetic industry, is evident nowadays. This plant is a source of coumarins, especially scopoletin, which are highly soluble in supercritical CO2 .

Concepts: Supercritical carbon dioxide, Helichrysum italicum

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The chemical composition and antioxidant properties of the essential oil and EtOH extract of immortelle (Helichrysum italicum (Roth) G.Don subsp. italicum, Asteraceae) collected in Montenegro were evaluated. The essential oil was characterized by GC/MS analysis, and the content of total phenolics and flavonoids in the EtOH extract was determined using the FolinCiocalteu reagent. The free-radical-scavenging capacity (RSC) of both the essential oil and the EtOH extract was assessed with the 2,2-diphenyl-1-pycrylhydrazyl (DPPH) method. Moreover, the inhibition of hydroxyl radical ((.) OH) generation by the EtOH extract of immortelle was evaluated for the first time here. Neryl acetate (28.2%) and γ-curcumene (18.8%) were the main compounds in the essential oil, followed by neryl propionate (9.1%) and ar-curcumene (8.3%). The chemical composition of the oils of the examined and additional 16 selected Helichrysum italicum taxa described in literature were compared using principal component (PCA) and cluster (CA) analyses. The results of the statistical analyses implied the occurrence of at least four different main and three subchemotypes of essential oils. Considering the antioxidant properties, the EtOH extract of immortelle exhibited similar potential as propyl gallate and quercetin, while the essential oil exhibited relatively weak DPPH(.) -scavenging capacity.

Concepts: Ethanol, Helichrysum, Helichrysum italicum, Oils, Propyl gallate, Oil, Antioxidant, Essential oil

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Helichrysum italicum (Roth) G. Don is a flowering plant of the family Asteraceae. It is rich in oil that is used for different medicinal purposes and in fragrance industry. Volatile profile of four populations of H. italicum, collected from natural habitat in Dalmatia (Croatia), was analysed by capillary GC-MS. Sample from BraČ Island had α-trans-bergamotene (10.2%) and β-acoradiene (10.1%) as the majors, whereas sample collected on Biokovo Mt. was rich in neryl acetate (8.1%). β-Acoradiene was also the main constituent of sample collected near Tijarica, whereas rosifoliol (8.5%) was the most abundant constituent in sample collected near Makarska. Presented results show the influence of environmental conditions on chemical differentiation of the volatiles of H. italicum from Croatia.

Concepts: Volatile, Flowering plant, Habitat, Flower, Helichrysum, Helichrysum italicum, Dalmatia, Asteraceae

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Helichrysum microphyllum Cambess. subsp. tyrrhenicum Bacch., Brullo e Giusso (Asteraceae), previously known as Helichrysum italicum ssp. microphyllum (Willd.) Nyman, is one of the many endemic species growing in Sardinia, Corsica and Balearic Islands. In the present work the composition of the essential oil obtained from a population of H. microphyllum ssp. thyrrenicum growing in a littoral location of La Maddalena Archipelago was investigated by GC-FID and CG-MS. The major compounds of the oil were the monoterpene ester neryl acetate (18.2%), the oxygenated sesquiterpene 5-eudesmen-11-ol (rosifoliol, 11.3%), the sequiterpene hydrocarbons δ-cadinene (8.4%) and γ-cadinene (6.7%), showing a peculiar composition in comparison with other Sardinian populations. The oil was tested for cytotoxicity on three human tumor cell lines (MDA-MB 231, HCT116 and A375) by MTT assay showing a strong inhibitory activity on human malignant melanoma cells A375 (IC50 of 16 µg/ml). In addition the oil was assessed for antioxidant activity by DPPH and ABTS assay.

Concepts: MTT assay, Melanoma, Helichrysum italicum, Mediterranean Sea, Cytotoxicity, Maddalena archipelago, La Maddalena, Sardinia

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A new acetophenone derivative named gnaphaliol 9-O-propanoate (1) was isolated from the chloroform fraction of EtOH extract of Helichrysum italicum ssp. italicum flowers along with the five known acetophenones 12-acetoxytremetone (2), 13-(2-methylpropanoyloxy)toxol (3), 2,3-dihydro-2-[1-(hydroxymethyl)ethenyl]-5-benzofuranyl]-ethanone (4), 1-[2-[1-[(acetyloxy)methyl]ethenyl]-2,3-dihydro-3-hydroxy-5-benzofuranyl]-ethanone (5) and gnaphaliol (6). The structures of compounds 1-6 were elucidated by extensive spectroscopic methods including 1D- ((1)H and (13)C) and 2D-NMR (DQF-COSY, HSQC, HMBC, TOCSY and ROESY) experiments as well as ESIMS analysis. The isolated compounds were investigated for their cytotoxicity, anti-inflammatory and antioxidant properties. Biological assays on human colonic epithelial cells showed that compound 2 possessed antioxidant effects reducing reactive oxygen species (ROS) production.

Concepts: Mitochondrion, Hydrogen peroxide, Helichrysum italicum, Epithelium, Oxidative phosphorylation, Oxygen, Reactive oxygen species, Antioxidant

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Helichrysum italicum is widely used in traditional medicine, in cosmetic, in food and pharmaceutical field. In spite of this, very little is known about the chemical composition of its polar extracts. Therefore this study was addressed to the determination of the metabolite profile of the methanol extract of H. italicum flowers, by using LC-ESI(IT)MSMS. This approach oriented the isolation of 14 compounds, whose structures were unambiguously elucidated by NMR as belonging to flavonoid, phenylpropanoid and acylbenzofuran classes. In addition, one novel drimane sesquiterpene was identified. The quantitative determination of the main compounds occurring in the methanol extract of H. italicum flowers was carried out and their content was compared with that of three selected commercial food supplements based on H. italicum, by using LC-ESI(QqQ)MS. In conclusion the wide occurrence, in high amounts, of quinic acid derivatives in all the analyzed samples was highlighted, showing these compounds as chemical markers of the species for standardization procedures.

Concepts: Medicine, Chemical compound, Identification, Helichrysum, Quinic acid, Extract, Helichrysum italicum