Phytochemical analysis and biological activities of the aerial parts of Odontites vulgaris Moench.

In this work, the first specific phytochemical analysis on Odontites vulgaris Moench collected in Central Italy was performed. The aerial parts ethanolic extract was studied and eight compounds were identified: pheophytin a (1), aucubin (2), catalpol (3), shanzhiside methyl ester (4), melampyroside (5), 8-epi-loganin (6), caryoptoside (7) and quinic acid (8). To the best of our knowledge, in this study, compounds (7-8) resulted to be isolated from the genus for the first time. The chemophenetic markers of the family and order were evidenced and several important ecological conclusions could be drawn. The ethanolic extract was also tested for several biological activities showing high effects in the antioxidant, cytoprotective and aflatoxin B1 production inhibitory assays. A brief explanation on these activities under the phytochemical standpoint was also included.

Phytochemical analysis on the aerial parts of Teucrium capitatum L. with aspects of chemosystematics and ethnobotany.

The phytochemical analysis on the aerial parts of Teucrium capitatum L. collected from a new population in Central Italy, led to the identification of eight compounds, i.e. pheophytin a (1), poliumoside (2), apigenin (3), luteolin (4), cirsimaritin (5), cirsiliol (6), 8-O-acetyl-harpagide (7) and teucardoside (8) belonging to four different classes of secondary metabolites. Pheophytin a (1) represents a newly identified compound in the genus whereas compounds (7-8) are newly identified compound in the species. The chemotaxonomic and ethnobotanical aspects relative to the presence of these compounds were widely discussed suggesting important conclusions for both.

Leucosceptosides A and B: Two Phenyl-Ethanoid Glycosides with Important Occurrence and Biological Activities.

In this review paper, the occurrence in the plant kingdom, the chemophenetic value and the biological activities associated with two specific phenyl-ethanoid glycosides, i.e., leucosceptoside A and leucosceptoside B, were reported. This is the first work ever conducted on such a subject. Analysis of the literature data clearly led to three important conclusions: leucosceptoside A is much more common in plants than leucosceptoside B; leucosceptoside A exerts more biological activities than leucosceptoside B even if nothing can be generally concluded about which one is actually the most potent; neither of these compounds can be used as a chemophenetic marker. These three aspects and more are discussed in more depth in this work.

A novel pentacyclic triterpene acid from the stem barks of Combretum fragrans F. Hoffm (Combretaceae).

A phytochemical study was carried out on stem bark of Combretum fragrans F. Hoffm., a medicinal plant belonging to the Combretaceae family and used traditionally in the treatment of various ailments. Column chromatography separation on silica gel of the crude methanol extract from stem barks of C. fragrans led to the isolation of a new pentacyclic triterpene acid, with a 3,6-epoxide bridge and trivially named as fragransinic acid (1), along with four known compounds: betulin (2), betulinic acid (3), bellericagenin B (4) and a mixture of ß-sitosterol (5) and stigmasterol (6). Structures were elucidated by extensive spectroscopic analyses including 1D and 2D NMR, mass spectrometry as well as by comparison with literature data. The above compounds were isolated for the first time from C. adenogonium. Implications for chemosystematics and traditional medicine were briefly discussed.

The Pharmacological Activities of Crocus sativus L.: A Review Based on the Mechanisms and Therapeutic Opportunities of its Phytoconstituents.

Crocus species are mainly distributed in North Africa, Southern and Central Europe, and Western Asia, used in gardens and parks as ornamental plants, while Crocus sativus L. (saffron) is the only species that is cultivated for edible purpose. The use of saffron is very ancient; besides the use as a spice, saffron has long been known also for its medical and coloring qualities. Due to its distinctive flavor and color, it is used as a spice, which imparts food preservative activity owing to its antimicrobial and antioxidant activity. This updated review discusses the biological properties of Crocus sativus L. and its phytoconstituents, their pharmacological activities, signaling pathways, and molecular targets, therefore highlighting it as a potential herbal medicine. Clinical studies regarding its pharmacologic potential in clinical therapeutics and toxicity studies were also reviewed. For this updated review, a search was performed in the PubMed, Science, and Google Scholar databases using keywords related to Crocus sativus L. and the biological properties of its phytoconstituents. From this search, only the relevant works were selected. The phytochemistry of the most important bioactive compounds in Crocus sativus L. such as crocin, crocetin, picrocrocin, and safranal and also dozens of other compounds was studied and identified by various physicochemical methods. Isolated compounds and various extracts have proven their pharmacological efficacy at the molecular level and signaling pathways both in vitro and in vivo. In addition, toxicity studies and clinical trials were analyzed. The research results highlighted the various pharmacological potentials such as antimicrobial, antioxidant, cytotoxic, cardioprotective, neuroprotective, antidepressant, hypolipidemic, and antihyperglycemic properties and protector of retinal lesions. Due to its antioxidant and antimicrobial properties, saffron has proven effective as a natural food preservative. Starting from the traditional uses for the treatment of several diseases, the bioactive compounds of Crocus sativus L. have proven their effectiveness in modern pharmacological research. However, pharmacological studies are needed in the future to identify new mechanisms of action, pharmacokinetic studies, new pharmaceutical formulations for target transport, and possible interaction with allopathic drugs.

A review of the phytochemistry, ethnopharmacology and biological activities of Teucrium genus (Germander).

Teucrium L (Lamiaceae) is mainly distributed in the Mediterranean area. A comprehensive survey in the electronic databases (during 2000-2020 years) with keywords of 'Teucrium' and 'Germander' showed that chemical analyses are available for 27 species, with sesquiterpenoids, iridoids, di and triterpenoids, and phenolic compounds as identified structures. The neo-clerodane diterpenoids as potential chemotaxonomic markers were the main compounds of this genus. As a result, Italy and Turkey have good attempts at phytochemical analysis. The pharmacological activities of different species including antioxidant, cytotoxic activity, antidiabetic, antimicrobial, anti-inflammatory and anti-insect have been summarized. Teucrium polium and Teucrium chamaedrys mainly have been used in digestive problems and diabetes in traditional medicine. Evidence-based clinical trials are needed to confirm the therapeutic properties of this genus. As well to the popularity of Asian and Anatolian species as ingredients in contemporary medicines and products, further research is required in comparison to European species.

Antimicrobial and α-glucosidase inhibitory activities of chemical constituents from Gardenia aqualla (Rubiaceae).

An aliphatic alkene namely pentapentacontene (4) was isolated for the first time from a natural source, Gardenia aqualla, along with fourteen other compounds including nonacosanol (1), tetratriacontanol (2), octatriacontanol (3), ß-sitosterol (5) and stigmasterol (6), daucosanol (7), ursolic acid (8), uvaol (9), 3ß,19α,23ß,24α-tetrahydroxyurs-12-en-28-oic acid (10), lupenone (11), oleanolic acid (12), vanillin (13), vanillic acid (14) and D-mannitol (15). α-glucosidase inhibitory assay revealed that MeOH and EtOAc extracts of leaves had the best activity with IC50 of 9.65 and 20.03 µg/ml respectively. All the tested compounds showed dose dependent inhibition of α-glucosidase and some of them were found to be comparable to acarbose. Compound 10 was the most potent with IC50 = 1.72 µM. It also showed the most interesting antibacterial activity, against the isolate strain of S. typhi and P. aeruginosa and also exhibited the most significant antifungal activities against all the tested yeasts.

An overview of the genus Aloysia Paláu (Verbenaceae): Essential oil composition, ethnobotany and biological activities.

Aloysia Paláu is an important herbal genus from the Verbenaceae family and possesses numerous remedial properties in the folk medicine of Asian, European, and, in particular, South American countries. Only a few reports have discussed some phytochemical characteristics associated with Aloysia species. Right the lack of an exhaustive report prompted us to organize this review article. Accordingly, besides the ethnobotanical knowledge of Aloysia species, their essential oil profiles, phytochemistry of the polar isolated fractions, and the relevant biological activities are discussed in detail.[Formula: see text].

Profiling of the essential oil compositions from the flowers and leaves of Tanacetum fisherae Aitch. & Hemsl., an endemic plant in Kerman province, Iran.

Tanacetum fisherae Aitch. & Hemsl. is an endemic plant growing wild in some brackish regions of Iran. Since there are not enough reports concerning the quantitative and qualitative analyses of its essential oil, it was decided to characterise the respective water-distilled oils obtained from the flowers and leaves of this medicinal plant. Characterisation of the corresponding essential oil profiles revealed that in both of the analysed oils, oxygenated monoterpenes constituted most of the chemical profiles. In this sense, the most prevailing natural compounds in the flower oils were cis-p-2-menthen-1-ol (11.2%), trans-p-2-menthen-1-ol (10.7%), trans-piperitol (7.8%), 1,8-cineole (6.1%), cis-piperitol (3.8%), α-terpineol (3.7%) and terpinene-4-ol (2.1%), whereas the main constituent components of the leaves oils were, respectively, 1,8-cineole (16.7%), cis-p-2-menthen-1-ol (14.6%), trans-p-2-menthen-1-ol (10.4%), trans-piperitol (12.8%), α-terpineol (5.4%), cis-piperitol (2.9%), borneol (2.7%), and terpinene-4-ol (2.1%). In addition, the second rank of natural compound constituting groups was due to oxygenated sesquiterpenes, as well.[Formula: see text].

A Systematic Review on Phytochemistry, Ethnobotany and Biological Activities of the Genus Bunium L.

The aim of this review article is to present, for the first time, an appraisal of the phytochemical, ethnobotanical and pharmacological data on Bunium species. The literature search was conducted using the Scopus, Google Scholar and PubMed databases. The genus Bunium has been found to produce both essential oil (EO), mainly comprising monoterpenes and sesquiterpenes, and non-volatile components mainly coumarins and flavonoids. There are several pharmacological activities associated with the Bunium species, especially antioxidant, antibacterial and antifungal properties. The chemotaxonomic appraisal of the phytochemical pattern of the genus is in sink with the current classification of the family. Moreover, this review confirms the significant ethnobotanical and pharmacological potential of different Bunium species.

The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities-A Review.

Herein, a comprehensive review is given focusing on the chemical profiles of the essential oils (EOs), non-volatile compounds, ethnobotany, and biological activities of different Haplophyllum (Rutaceae family) species. To gather the relevant data, all the scientific databases, including Scopus, ISI-WOS (Institute of Scientific Information-Web of Science), and PubMed and highly esteemed publishers such as Elsevier, Springer, Taylor and Francis, etc., were systematically retrieved and reviewed. A wide array of valuable groups of natural compounds, e.g., terpenoids, coumarins, alkaloids, lignans, flavonoids, and organic acids have been isolated and subsequently characterized in different organic extracts of a number of Haplophyllum species. In addition, some remarkable antimicrobial, antifungal, anti-inflammatory, anticancer, cytotoxic, antileishmanial, and antialgal effects as well as promising remedial therapeutic properties have been well-documented for some species of the genus Haplophyllum.

Phytochemical Analysis and Biological Activities of the Ethanolic Extract of Daphne sericea Vahl Flowering Aerial Parts Collected in Central Italy.

In this paper, the first phytochemical analysis of the ethanolic extract of Daphne sericea Vahl flowering aerial parts collected in Italy and its biological activities were reported. Eleven compounds were identified i.e., α-linolenic acid (1), tri-linoleoyl-sn-glycerol (2), pheophorbide a ethyl ester (3), pilloin (4), sinensetin (5), yuanhuanin (6), rutamontine (7), syringin (8), p-coumaric acid (9), p-anisic acid (10) and caffeic acid (11). To the best of our knowledge, compounds (1-4, 7-8 and 10) were isolated from D. sericea for the first time during this work, whereas sinensetin (5) represents a newly identified component of the entire Thymelaeaceae family. The extract was found to possess radical scavenging against both DPPH• and 2,2'-azino-bis(3-thylbenzothiazoline-6-sulfonic acid (ABTS•+) radicals, with at least a 40-fold higher potency against the latter. Moreover, chelating abilities against both ferrous and ferric ions have been highlighted, thus suggesting a possible indirect antioxidant power of the extract. Although the precise bioactive compounds remain to be discovered, the polyphenolic constituents, including phenolic acids, tannins and flavonoids, seem to contribute to the antioxidant power of the phytocomplex. In addition, the extract produced cytotoxic effects in MDA-MB-231 and U87-MG cancer cell lines, especially at the concentration of 625 µg/mL and after 48-72 h. Further studies are required to clarify the contribution of the identified compounds in the bioactivities of the extract and to support possible future applications.

Curcumin nanoformulations for antimicrobial and wound healing purposes.

The development and spread of resistance to antimicrobial drugs is hampering the management of microbial infectious and wound healing processes. Curcumin is the most active and effective constituent of Curcuma longa L., also known as turmeric, and has a very long and strong history of medicinal value for human health and skincare. Curcumin has been proposed as strong antimicrobial potentialities and many attempts have been made to determine its ability to conjointly control bacterial growth and promote wound healing. However, low aqueous solubility, poor tissue absorption and short plasma half-life due its rapid metabolism needs to be solved for made curcumin formulations as suitable treatment for wound healing. New curcumin nanoformulations have been designed to solve the low bioavailability problem of curcumin. Thus, in the present review, the therapeutic applications of curcumin nanoformulations for antimicrobial and wound healing purposes is described.

Phytochemical profile of fennel essential oils and possible applications for natural antioxidant and controlling Convolvulus arvensis L.

The natural compounds such as essential oils are getting more attention due to their potential usage in pharmaceuticals and possibly as natural herbicides. This study was conducted to identify the chemical compositions of essential oils from Foeniculum vulgare Mill. populations collected from different regions of Iran, Turkey, and Germany, and their antioxidant (DPPH·, ABTS·+ and reducing power methods) and phytotoxic activity (against Convolvulus arvensis L.). The results exhibited a significant variation in essential oils content (1.74-2.97%). The main compounds in essential oils were trans-anethole (15.23%-90.11%), estragole (4.00-63.72%), fenchone (0.03-12.62%) and limonene (1.05-13.04%). The results revealed that the essential oils have considerable antioxidant (IC50 values in the range of 11.83-36.90 mg mL-1 in DPPH, 7.65-20.13 mg mL-1 in ABTS·+ and EC50 values in the range of 3.65-15.24 mg mL-1 in reducing power assay) and phytotoxic activity. The results of this study can help in the development of natural antioxidants and herbicides.

Plants adapted to arid areas: specialized metabolites.

Drought stress affects growth, morphological and biochemical properties in plants. To develop resistance and adapt to drought, plants need metabolic changes. Adaptations to stress involve changes to gene expression that activate metabolic processes that promote drought resistance and that may include biosynthesis and accumulation of specialized metabolites. Such adaptations in specialized metabolism may be important mechanisms leading to plant stress resistance and involve production of phenolics, flavonoids, terpenoid and nitrogen containing compounds that are species and genotype specific. Most plants having special metabolites to adapt to drought stress belong to different botanical families. C3, C4 and CAM plants, apply both morphological and metabolic mechanisms to adapt to drought as well as to accumulate specialized metabolites. Generally, medicinal plants increase their functional metabolites content, when exposed to drought stress. During drought stress, transcription factors and related pathways for biosynthesis of phenolics, flavonoids, anthocyanins as well as for stress jasmonate and abscisic acid stress hormones are activated.

Composition and biological activities of the essential oil from a Sicilian accession of Prangos ferulacea (L.) Lindl.

Prangos ferulacea (L.) Lindl. (Fam. Apiaceae), is an orophilous species of eastern Mediterranean and western Asia which possesses several biological properties, which are worthy of exploitation in different fields. With the aim to provide new insights into the phytochemistry and pharmacology of this species, a local accession growing in Sicily (South Italy) was investigated as well. Notably, the P. ferulacea essential oil chemical composition and the antioxidant, anti-acetylcholinesterase (AChE) and cytotoxic activities have been studied. This analysis allowed to identify a new chemotype and to report good biological results for this oil.

Bioguided fractionation of hypoglycaemic component in methanol extract of Vernonia amygdalina: an in vivo study.

Nine components (C1-C9) were isolated from chloroform fraction of fractionated methanol extracts of Vernonia amygdalina leaves (FMEVA) by column chromatography. All the components C1 to C9 were purified and screened for hypoglycaemic activities in type-2 diabetic rats. The most potent hypoglycaemic component was elucidated on the basis of extensive spectroscopic (1D-, 2D-NMR, GC-MS, FTIR) data analysis. The Component C5 was found to be the most potent hypoglycaemic in reducing blood glucose by 12.55 ± 3.55% at 4 h post-oral administration, when compared to the positive (18.07 ± 1.20%) and negative (-1.99 ± 0.43%) controls. The spectroscopic data analysis reveals that the isolated compound has a structure consistent with 11ß,13-dihydrovernolide. The isolated compound is part of the hypoglycaemic components present in V. amygdalina leaves that is responsible for the anti-diabetic activities. Further research is needed in the development of this compound or its derivatives for pharmaceutical use.

Phytochemistry, Chemotaxonomy, and Biological Activities of the Araucariaceae Family-A Review.

In this review article, the phytochemistry of the species belonging to the Araucariaceae family is explored. Among these, in particular, it is given a wide overview on the phytochemical profile of Wollemia genus, for the first time. In addition to this, the ethnopharmacology and the general biological activities associated to the Araucariaceae species are singularly described. Lastly, the chemotaxonomy at the genus and family levels is described and detailed.

Phytochemical Analysis and Trypanocidal Activity of Marrubium incanum Desr.

The rationale inspiring the discovery of lead compounds for the treatment of human parasitic protozoan diseases from natural sources is the well-established use of medicinal plants in various systems of traditional medicine. On this basis, we decided to select an overlooked medicinal plant growing in central Italy, Marrubium incanum Desr. (Lamiaceae), which has been used as a traditional remedy against protozoan diseases, and to investigate its potential against Human African trypanosomiasis (HAT). For this purpose, we assayed three extracts of different polarities obtained from the aerial parts of M. incanum-namely, water (MarrInc-H2O), ethanol (MarrInc-EtOH) and dichloromethane (MarrInc-CH2Cl2)-against Trypanosoma brucei (TC221), with the aim to discover lead compounds for the development of antitrypanosomal drugs. Their selectivity index (SI) was determined on mammalian cells (BALB/3T3 mouse fibroblasts) as a counter-screen for toxicity. The preliminary screening selected the MarrInc-CH2Cl2 extract as the most promising candidate against HAT, showing an IC50 value of 28 µg/mL. On this basis, column chromatography coupled with the NMR spectroscopy of a MarrInc-CH2Cl2 extract led to the isolation and identification of five compounds i.e. 1-α-linolenoyl-2-palmitoyl-3-stearoyl-sn- glycerol (1), 1-linoleoyl-2-palmitoyl-3-stearoyl-sn-glycerol (2), stigmasterol (3), palmitic acid (4), and salvigenin (5). Notably, compounds 3 and 5 were tested on T. brucei, with the latter being five-fold more active than the MarrInc-CH2Cl2 extract (IC50 = 5.41 ± 0.85 and 28 ± 1.4 µg/mL, respectively). Furthermore, the SI for salvigenin was >18.5, showing a preferential effect on target cells compared with the dichloromethane extract (>3.6). Conversely, stigmasterol was found to be inactive. To complete the work, also the more polar MarrInc-EtOH extract was analyzed, giving evidence for the presence of 2″-O-allopyranosyl-cosmosiin (6), verbascoside (7), and samioside (8). Our findings shed light on the phytochemistry of this overlooked species and its antiprotozoal potential, providing evidence for the promising role of flavonoids such as salvigenin for the treatment of protozoal diseases.

Secondary metabolites of Tilia tomentosa Moench inflorescences collected in Central Italy: chemotaxonomy relevance and phytochemical rationale of traditional use.

In this paper, the phytochemical analysis on the inflorescences (flowers and bracts) of a sample of Tilia tomentosa collected from an isolated population in Central Italy, was reported for the first time. Thirteen compounds (oleanolic acid, maslinic acid, apigenin, luteolin, kaempferol, quercetin, kaempferol-3-O-glucoside, quercetin-3-O-glucoside, rutin, tiliroside, ellagic acid, shikimic acid and quinic acid), belonging to several different classes of natural products, were identified on the basis of spectroscopic and spectrometric analysis. This sample was found to be mainly composed by flavonoids, followed by organic acids and pentacyclic triterpenes. The chemosystematic aspects of the identified components were also discussed, together with their pharmacologic relevance with respect to the traditional medicinal uses of this plant material.