Globularia Species Research Articles

Globularia alypum L. and Related Species: LC-MS Profiles and Antidiabetic, Antioxidant, Anti-Inflammatory, Antibacterial and Anticancer Potential.

Species from the genus Globularia L. have been used as healing agents for various ailments, with utilization of Globularia alypum L. being most frequently reported. The aim of this study was to evaluate the antidiabetic, antioxidant, anti-inflammatory, antibacterial and anticancer potential of G. alypum and three related species, G. punctata Lapeyr., G. cordifolia L. and G. meridionalis (Podp.) O.Schwarz, in relation to their phytochemical compositions. Globularin and verbascoside were identified using LC-PDA-ESI-MSn as the major metabolites of G. alypum with known biological activities. G. alypum demonstrated the greatest α-glucosidase inhibitory activity and DPPH radical scavenging activity (IC50 = 17.25 μg/mL), while its anti-inflammatory activity was not significantly different from those of related species. All investigated species showed considerable antibacterial activity against methicillin-resistant Staphylococcus aureus in the broth microdilution method (MIC = 1.42–3.79 mg/mL). G. punctata also showed antibacterial activities against Escherichia coli (MIC = 1.42 mg/mL), Bacillus subtilis (MIC = 1.89 mg/mL), B. cereus (MIC = 2.84 mg/mL) and Enterococcus faecalis (MBC = 5.68 mg/mL). G. punctata, G. cordifolia and G. meridionalis showed greater anticancer potential than G. alypum. Obtained results indicate investigated Globularia species could serve as sources of diverse bioactive molecules, with G. punctata having the greatest antibacterial potential.

Explaining Intricate Morphometric Variability with Environmental Predictors: The Case of Globularia cordifolia Species Complex.

Globularia is a genus of small evergreen and perennial shrubs that are widespread in Europe. Globularia section Empetron includes a group of three species, G. cordifolia, G. meridionalis, and G. neapolitana, that have been taxonomically disputed for more than 150 years. Many morphological features have been proposed to discriminate these species. Nevertheless, evidence from both past and recent literature suggest that these differences among species are not consistent. In order to shed new light in this long-disputed group, we investigated 10 populations of the G. cordifolia species complex with both classical and geometric morphometrics and used environmental predictors in multivariate regression to explain patterns of variation. Our results showed that bract area and calyx teeth length are correlated with solar radiation and annual precipitation, whereas leaf dry mass per unit area can be explained by temperature seasonality. Leaf shape can be explained by temperature seasonality as well, although with a lower amount of explanatory and predictive power. Despite a comparatively low sample size in terms of populations, our results were based on a large number of individuals and were supported by a robust statistical approach. We can conclude that differences among the three species of Globularia could be related to the combined effects of several ecological variables and might not have taxonomical value. Our novel approach provided an ecological interpretation on a species complex that makes up a continuum of forms within the environmental framework of the Mediterranean basin.

Actualities in the phytochemical research on selected terpenes.

A short review of our recent research on the essential oil phytochemical composition of Petasites albus (L.) Gaertn. and Petasites hybridus (L.) G. Gaertn., B. Mey. & Scherb. (Asteraceae) as well as on the oils of Globularia cordifolia L., Globularia meridionalis (Podp.) O. Schwarz and Globularia punctata Lapeyr. (Plantaginaceae) is presented. All essential oils contained a variety of oxygenated sesquiterpenes among their major constituents, including a bakkane type sesquiterpene fukinanolid (bakkenolide A). The paper is focused on: i) a short overview of the abundance of major terpenes in the essential oils of Petasites and Globularia species from Croatia; ii) possible biosynthetic pathways of major identified sesquiterpenes; and iii) biological activities (literature data) of major sesquiterpenes from Petasites and Globularia species.

Chemical fingerprint and bioactivity evaluation of Globularia orientalis L. and Globularia trichosantha Fisch. & C. A. Mey. using non-targeted HPLC-ESI-QTOF-MS approach.

In the quest for new sources of biologically-active compounds, the chemical, and biological profiles of two Globularia species (G. trichosantha Fisch. & C. A. Mey and G. orientalis L.) were investigated. Chemical profiles were evaluated by high-performance liquid chromatography coupled to electrospray ionisation and quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS), as well as by their total phenolic, flavonoids, and phenolic acids contents. The antioxidant abilities of the investigated extracts were done using different assays including free radical scavenging [1,1-diphenyl-2-picryl-hydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS)], reducing power (cupric reducing antioxidant capacity and ferric reducing antioxidant power), phosphomolybdenum, and metal chelating. Inhibitory potential against key enzymes involved in neurodegenerative diseases (cholinesterases; AChE, and BChE), diabetes (α-glucosidase and α-amylase), hyperpigmentation (tyrosinase) and obesity (pancreatic lipase) were evaluated. Globularia trichosantha and G. orientalis extracts showed remarkable antioxidant properties, with the water extracts being a better source of antioxidant compounds. Both species showed remarkable inhibitory effects against the target enzymes. However, for both species, only the acetyl acetate and methanolic extracts were potent against cholinesterases and lipase. HPLC-ESI-QTOF-MS analysis revealed the presence of 107 compounds from G. trichosantha and G. orientalis, among which, 43 compounds have been preliminarily characterised for the first time from the Globulariaceae family. To date, this study can be considered as the most comprehensive research focused on the characterisation of G. trichosantha and G. orientalis. Results amassed from this study tend to show that these plants represent a rich source of biologically active compounds which can be further explored and validated for their therapeutic potential.

LC‐PDA‐ESI‐MSn analysis of phenolic and iridoid compounds from Globularia spp.

Plants produce a great number of metabolites with potentially useful biological activities. Species from the genus Globularia (Plantaginaceae) are known as sources of different phenolic and iridoid compounds. Globularia alypum L. is a medicinal plant used as a healing agent in many Mediterranean countries. Similarities in phytochemical composition are often observed for related species. For Globularia spp., such findings were mostly based on identification of several isolated compounds from distinct species. To our knowledge, this is the first study that enables simultaneous comparison of phytochemical profiles from several members of the genus Globularia. Liquid chromatography-photodiode array detection-electrospray ionization-tandem mass spectrometry was used for the analysis of methanolic extracts of aerial parts obtained from four Globularia species (G. alypum, G. punctata, G. cordifolia and G. meridionalis). In total, 85 compounds were identified or tentatively identified based on comparison of their retention time, UV and MSn (up to MS4 ) spectra to those of standard compounds and/or to literature data. Among these, high relative amounts of bioactive molecules such as globularin, globularifolin, asperuloside and verbascoside (acteoside) were found. Apart from providing new insights into the phytochemistry and chemotaxonomy of selected Globularia species, results of this study complement existing MS/MS spectral data and could enable easier mass spectrometric profiling of certain bioactive compounds such as iridoids and phenylethanoids in related plant species, genera and families. Copyright © 2016 John Wiley & Sons, Ltd.

Essential Oil Composition of Three Globularia Species.

The chemical composition of the essential oils obtained by hydrodistillation from the aerial parts of Globularia cordifolia L., G. meridionalis (Podp.) O.Schwarz, and G. punctata Lapeyr. was characterized by GC-FID and GC/MS analyses. Among the 33 identified compounds, the most abundant present in all investigated samples were oct-1-en-3-ol (2.9-47.0%), 6-(1,5-dimethylhex-4-enyl)-3-methylcyclohex-2-enone (8.2-40.9%), and fukinanolid (7.4-31.6%). Multivariate statistical analyses (PCA and HCA) of the hitherto studied Globularia volatile compounds confirmed to some extent the assumed phylogenetic relationships of the Globularia species studied, including the close relationship between the morphologically similar species G. cordifolia and G. meridionalis, but also evidenced several discrepancies in the current classification of Globularia species.

Analysis of aucubin and catalpol content in different plant parts of four Globularia species

Iridoids are plant secondary metabolites that are gaining more scientific interest due to the wide range of their observed biological activities such as neuroprotective, anti-inflammatory, immunomodulatory, hepatoprotective and cardioprotective. The presence and content of aucubin and catalpol, two iridoid glucosides frequently present in iridoid-containing plants, was studied in methanolic extracts of leaves, flowers, woody stems and underground parts of four Globularia L. species, including the medicinal plant Globularia alypum L., using a specific and reliable HPLC-DAD-ESI/MS method. Aucubin was found in all four species, while catalpol was found only in G. alypum and G. punctata . Flowers contained the highest amounts of investigated iridoids, with catalpol content reaching 1.6% in G. punctata flowers. Comparing to the medicinal plant G. alypum , related species contained higher amounts of investigated iridoids, which makes them interesting candidates for further biological activity investigations. The online version of this article (doi: 10.5073/JABFQ.2015.088.030) contains supplementary files .

Iridoid and bisiridoid glycosides from Globularia meridionalis (Podp.) O. Schwarz aerial and underground parts

1. Subject and sourceThegenusGlobularia,recentlyincludedinPlantaginaceaeonmolecularsystematicsgrounds(APG,1998;APGII,2003;APGIII, 2009), has its centre of distribution in the Mediterranean region and southern Europe with a considerable number oflocallyendemic species in theCape Verde andCanaryIslands, Atlas, Baleares,Italy, Greece andTurkey(Elbetieha et al., 2000).Some members of this genus are well known for their biological properties. Globularia alypum L. is used for a variety ofpurposes such as hypoglycaemic agent, laxative, cholagogue, stomachic, purgative, sudorific and also in the treatment ofcardio-vascular and renal diseases (Bellakhdar et al., 1991). G. arabica Jaub. & Spach is used in Jordan traditional medicine(Oran and Al-Eisawi, 1998). Both Globularia species are also known for their antimicrobial and antitumorigenic activities(Elbetieha et al., 2000). Globularia trichosantha Fisch. & C.A. Mey. is utilized for the treatment of haemorrhoids (Sezik et al.,1991).TheBalkan-ApennineGlobulariameridionalis(Podp.)O.SchwarzisoneoftheeightspeciesgrowinginItaly,togetherwith:G. alypum, Globularia bisnagarica L., Globularia cordifolia L., Globularia incanescens Viv., Globularia neapolitana O. Schwarz,Globularia nudicaulis L. and Globularia repens Lam. (Pignatti, 1982; Conti et al., 2005). Aerial and underground parts of G.meridionalis were collected in Pollino Massif, Calabria (Italy). Voucher specimen has been retained at the Herbarium ofUniversity of Calabria (CLU) under the reference no 12492.

Secondary Metabolites from Globularia alypum

The genus Globularia (Globulariaceae) includes two species in Algeria. One of them is endemic, Globularia eriocephala (Pomel); the other Globularia alypum L., widespread in the Mediterranean region [1], is used in folk medicine. Its leaves are traditionally used as a hypoglycemic agent, laxative [2], cholagogue, stomachic, purgative, and sudorific [3]. In the present paper we report on the qualitative and quantitative analysis of secondary metabolites extracted from the medicinal plant G. alypum, which has been the subject of several chemical and pharmacological investigations [4–10]. Aerial parts of Globularia alypum L. were collected during the flowering season in eastern Algeria (April 2004). A voucher specimen for this material (VAREN/ SB BF Rv /04/04) was deposited at the Herbarium of the Faculty of Sciences, University MentouriConstantine. Air-dried and powdered aerial parts (1280 g) of G. alypum were macerated in an ethanolic solution (70%); the residue was filtered, concentrated, then successively extracted with petroleum ether, trichloromethane, ethyl acetate, and n-butanol. The AcOEt extract (10 g) was applied to a column of silica gel 60 and eluted with a gradient of CHCl3–CH3COCH3 with increasing polarity. Preparative TLC on silica gel 60 F254 using CHCl3–acetone–acetic acid (4:0.25:0.25) led to luteolin, para-coumaric acid, and cinnamic acid, while using CHCl3–acetic acid (4:0.25) led to apigenin. The para-coumaric acid and cinnamic acid have already been isolated from this plant [4, 5]. Flavonic compounds were identified using UV and 1H NMR spectra, chemical transformations, and comparison with authentic samples [11, 12]. Flavonoids 1, 2 have been isolated previously from another species of Globularia [13], but from G. alypum L. this was the first time. Apigenin, C15H10O5, mp 348–350°C, UV (λmax, MeOH, nm): 268, 335; +NaOH: 274, 324, 392; +AlCl3: 274, 300, 348, 382; AlCl3/HCl: 274, 300, 334, 380; NaOAc: 276, 306, 380. 1H NMR (250 MHz, CD3COCD3, δ, ppm, J/Hz ): 7.90 (2H, d, J = 8.7, H-2′, H-6′); 7.02 (2H, d, J = 8.7, H-3′, H-5′); 6.65 (1H, s, H-3); 6.55 (1H, d, J = 2.2, H-8); 6.26 (1H, d, J = 2.2, H-6). Luteolin, C15H10O6, mp 329–331°C, UV (λmax, MeOH, nm): 264, 350; +NaOH: 267, 329, 402; +AlCl3: 273, 303, 422; AlCl3/HCl: 274, 297, 358, 385; NaOAc: 254, 269, 352. 1H NMR (250 MHz, CD3COCD3, δ, ppm, J/Hz): 7.52 (1H, d, J = 2, H-2′); 7.49 (1H, dd, J = 8.4; 2, H-6′); 7.02 (1H, d, J = 8.4, H-5′); 6.62 (1H, s, H-3); 6.55 (1H, d, J = 2, H-8); 6.26 (1H, d, J = 2, H-8).

Secondary metabolites of Globularia species from the Flora of Turkey

Secondary metabolites of Globularia species from the Flora of Turkey

A new species ofGlobularia (Globulariaceae)from the Talassemtane National Park, N Morocco

Mateos, M. A. & Valdés, B.: A new species of Globularia (Globulariaceae) from the Talassemtane National Park, N Morocco. — Willdenowia 36 (Special Issue): 409–412. — ISSN 0511-9618; © 2006 BGBM Berlin-Dahlem. doi:10.3372/wi.36.36137 (available via http//dx.doi.org/)Globularia greuteri is described as a species new to science and illustrated. It is endemic to the Talassemtane National Park in the Western Rif Mts in N Morocco. The morphological differences between the new species and its closest relative, G. liouvillei from the Moroccan High Atlas, are pointed out.

A new species of Globularia L. (Globulariaceae) from South Anatolia

A new species of Globularia L G. hedgei H. Duman sp. nov., is described and illustrated. The species is restricted to the south of Sütçüler (Isparta) and grows on calcareous rocky cliffs. It is suggested that its IUCN category is Critically Endangered (CR). Diagnostic morphological characters for a detailed discrimination from the most closely similar taxa are discussed.

A new species of Globularia L. (Globulariaceae) from South Anatolia

A new species of Globularia L G. hedgei H. Duman sp. nov., is described and illustrated. The species is restricted to the south of Sutculer (Isparta) and grows on calcareous rocky cliffs. It is suggested that its IUCN category is Critically Endangered (CR). Diagnostic morphological characters for a detailed discrimination from the most closely similar taxa are discussed.

Morphologie, Biologie und ökogeographische Differenzierung von Globularia : I. Progessionen in der Wuchsform, Infloreszenz, Blattnervatur und Verbreitung

The species of Globularia are investigated with respect to their growth form, leaf structure, leaf venation, and inflorescences. An attempt is made to interprete the character progressions in connection with the ecogeographical differentiation which followed the alpidic orogenesis and the development of the Mediterranean climate during the late Tertiary. All Globularia species have woody stems or stem bases (the structure of wood not being “pedomorphous”), all are evergreen or semi-evergreen. Some may produce buds on the hypocotyle ( G. salicina ) or on the roots ( G. punctata ). The primary root dominates the root system in most species during the whole life of the plant (exception: the G. cordifolia-group ). On the Canary Islands, rather high laurophyllous shrubs (“feather-duster form”) with undifferentiated dolichoblasts and without bud scales have deloped. In the semiarid parts of the Mediterranean, dwarfed sclerophyllous shrubs with clearly differentiated dolicho- and brachyblasts and open shoot buds grow in dry garrigues on rocky sites. In the most arid parts of the Globularia range, the growth form is transformed to dwarf shrubs whith very short yearly increment. In the high mountains of the Mediterranean, espalier shrubs with long twigs hang from rocky faces, and espalier dwarf shrubs cover the horizontal rocks collecting their own humus layers. In dry rocks of the high mountains of southwestern Turkey, hemisphaerical cushion shrubs occur, reminiscent a growth form broadly distributed in the mountains of the middle East. In the temperate mountains, eleiocormous rosette plants have developed, growing today also on hilly relict sites in limestone rocks in Germany, Öland, Gotland, and eastern Russia. The leaf duration is only slightly reduced from over two years to semi-summergreen. The leaf structure changes from laurophyllous and subsucculent to sclerophyllous and even spiny. With increasing aridity, the number ofleafnerves, free nervillae, and areolae increases, and the anatomy of the leaves changes from bifacial ( G. salicina, G. nudicaulis ) to aequifacial amphistomatic (e.g., G. alypum, G. arabica ). The development of nervation types procedes from brochidodromous to camptodromous and craspedodromous. The inflorescences are compared with those of the related genus Poskea. In contrast to earlier descriptions, their arrangement is primarily terminal. The axillary position in the sect. Lytanthus is interpreted by the authors as a derived character state (proliferating synflorescence). Another derived state is the reduction to a single terminal head.

A chemosystematic study of Veronica: Iridoid glucosides

Caffeoyl-catalpol, isoferuloyl-catalpol, protocatechuoyl-catalpol, benzoyl-catalpol, p-hydroxybenzoyl catalpol (catalposide), vanilloyl-catalpol and cinnamoyl-aucubin have been isolated from several Veronica species (Scrophulariaceae) in a more or less pure state. The first four compounds have never been recorded in plants before. A PC survey of forty-three species of the genus sensu lato has shown a general presence of aucubin and catalpol. They are accompanied in many of the species by a complex mixture of esters, especially esters of catalpol with aromatic acids. In only one species have aucubin esters been found. Loganin has been identified in five species, this being the first time that this compound has been found in the Scrophulariaceae. Loganin is accompanied by unidentified loganin esters in the same five species. From the systematic point of view the complex mixtures of esters of catalpol in Veronica seem to be noteworthy. Species of Globularia, Erinus, Scrophularia Verbascum, Wulfenia, Catalpa and Plantago investigated either totally lacked ester glucosides in leaves or contained mainly different types of esters. The possible systematic meaning of these results is briefly discussed.