The first phytochemical analysis on the total non-volatile specialized metabolites of Cupressus torulosa identified nine compounds. Three of these are newly reported in the organs of this species whereas five of these are newly reported in the species as widely demonstrated by the chemophenetic evaluation.

The phytochemical profile of an Italian accession of Carlina acaulis subsp. caulescens f. typica Cianfaglione is here reported for the first time. Nine secondary metabolites were identified from the aerial parts including one degradation product of chlorophylls, two pentacyclic triterpenoids, one flavonoid, four quinic acid derivatives and one simple organic acid. Their structures were elucidated through NMR and MS analyses. The chemophenetic evaluation revealed the occurrence of two compounds reported for the first time in the genus and three compounds newly identified for the species. However, due to their widespread distribution among plant taxa, these metabolites cannot be considered reliable chemophenetic markers. These phytochemical results have also been compared with those obtained from a recently described new form of the species, finding a few similarities. These results surely demand further in-depth studies on both forms.

In this paper, the volatile phytochemical pattern of the resins of five Commiphora Jacq. species collected in Socotra Island was reported. Different populations were studied, some of which for the first time, by using head space-solid phase microextraction (HS-SPME) sampling technique to collect the volatiles emitted from these species. All the captured volatile compounds in the accessions were identified and quantified by means of GasChromatography/Mass Spectrometry (GC/MS). The obtained results highlighted the presence of terpene compounds, mainly monoterpenes and sesquiterpenes, which followed a different trend among the studied species in accordance with the ecology of the collection areas of the species. Sesquiterpenes were predominant in C. kua and, in part, in C. ornifolia; monoterpenes were predominant in C. planifrons and C. parvifolia, whereas oxygenated monoterpenes were predominant in C. socotrana. A high number of the so-called other volatile components were found in C. planifrons. The dominant compounds were gamma-cadinene in both accessions of C. kua, J3-eudesmol in the first accession of C. ornifolia and S-cadinene in its second accession, limonene in both accessions of both C. planifrons and C. parvifolia, terpinen-4-ol in both accessions of C. socotrana. The meaning of the data was considered under the chemophenetic, ecological and ethnobotanical aspects.

In this work, the first complete phytochemical analysis ever performed on a European population of Phlomis fruticosa L., led to the identification of twelve metabolites from its leaf ethanolic extract: pheophytin a (1), verbascoside (2), leucosceptoside A (3), apigenin (4), kaempferol (5), 5-hydroxy-8-epi-loganin (6), lamiide (7), penstemoside (8), 5-deoxy-pulchelloside I (9), quinic acid (10), vanillic acid (11) and glycerol (12). Their chemophenetic value was evaluated individuating and even suggesting chemophenetic markers at various levels.

The continuation of the phytochemical analysis to determine the alkaloid content of Vinca difformis subsp. sardoa Stearn, led to the isolation of the further compound vincamajine (1) which was reported from the species for the first time during this study. Its structure was established by means of extensive NMR, IR and MS analyses which are completely reported in this paper for the first time. In addition, the first chemophenetic evaluation about this compound was also carried out evidencing some important results which were fully described and discussed in this paper.

In this paper, the first phytochemical analysis on Teucrium chamaedrys subsp. gracile was reported. The dried aerial parts collected in Algeria were studied, and the analysis was conducted using different techniques: gas chromatography/mass spectrometry (GC/MS) for the fatty acid content, headspace solid-phase microextraction-GC-MS for the volatile composition, column chromatography along with nuclear magnetic resonance spectroscopy, and MS for non-volatile pattern characterization. Saturated fatty acids were found to be prevalent, with palmitic acid as the major compound. In the volatile fraction, β-caryophyllene and humulene, comprised in the class of sesquiterpenes, were the major components. Indeed, five non-volatile compounds were observed, namely teucrioside (1), cirsiliol (2), harpagide (3), and chlorogenic acid (4). The employed analytical techniques have proven to be suitable for producing reliable and reproducible results in the description of the phytochemical profile of the matrix.

The purpose of this study was to determine the phytochemical composition of different organs of Stachys alpina L. collected in Poland, in light of the significant lack of data available in the literature. In particular, roots, stems, leaves and flowers of this species were collected around the town of Szczytna and extracted by alcoholic maceration. Four molecules-namely verbascoside (1), harpagide (2), melittoside (3) and chlorogenic acid (4)-were identified from these extracts by comparing their spectroscopic data with those reported in the literature. Some of these were found in common but none of them was reported in all the studied organs. In addition, during this study, for the first time, verbascoside (1) was identified in the species whereas harpagide (2) in the roots of this species. The chemophenetic significance of these findings is discussed in detail.

In this review paper, the occurrence in plants, structural variability, possible chemophenetic value and pharmacological activities of tris- and tetrakis-iridoids were reported altogether for the first time. In particular, the exact number of these compounds discovered so far was presented, listing their names and detailing the plant species of their recovery with their organs and belonging family as well as the methodologies adopted for their extraction, separation and identification. The structural characteristics of tris- and tetrakis-iridoids were displayed with a particular focus on their specific peculiarities. A chemophenetic evaluation to individuate possible chemophenetic markers among tris- and tetrakis-iridoids was performed on the base of their occurrence at the species, genus and family levels along with a parallel discussion on the regularity of their distribution in the different plant organs. The pharmacological studies on tris- and tetrakis-iridoids were shown after a complete survey of literature data. All these data were widely compared with respect to simple iridoids and bis-iridoids when possible, too. This review paper clearly demonstrates that the research on tris- and tetrakis-iridoids is far from being exhaustive under several aspects and may indeed represent a starting point for future works.

In this work, a preliminary screening of the bioactivities of an ethanolic extract obtained from the leaves of Wollemia nobilis W.G.Jones, K.D.Hill & J.M.Allen was carried out to explore its potential pharmaceutical applications. In particular, the radical scavenging, chelating, reducing antiglycative, antimicrobial and antifungal activities as well as the inhibitory effects on the production of aflatoxin B1 in Aspergillus flavus Link were evaluated. The extract demonstrated promising biological activities, although generally with lower potency compared to the positive control. To identify the metabolites potentially responsible for these effects, the extract was subjected to phytochemical analysis evidencing the presence of eight known compounds. Among them, 15-agathic acid methyl ester (1) and ladanein (5) were reported for the first time in this species. Furthermore methyl-(E)-communate (2), 7,4′,7″,4‴-tetra-O-methyl-robustaflavone (6), agathisflavone (7) and quinic acid (8) were detected for the first time in the leaf tissue of W. nobilis. Their presence and the presence of isocupressic acid (3) and acetyl-isocupressic acid (4) in this species highlights the taxonomic correlations within the Araucariaceae family and suggests a possible contribution of these compounds in the bioactivities of the extract. However, further studies are required to confirm these contributions and to elucidate their mechanisms of action.

In this work, the first review paper about bis-iridoids was presented. In particular, their detailed occurrence, chemophenetic evaluation and biological activities were reported. To the best of our knowledge, two hundred and eighty-eight bis-iridoids have been evidenced so far, bearing different structural features, with the link between two seco-iridoids sub-units as the major one. Different types of base structures have been found, with catalpol, loganin, paederosidic acid, olesoide methyl ester, secoxyloganin and loganetin as the major ones. Even bis-irdioids with non-conventional structures like intra-cyclized and non-alkene six rings have been reported. Some of these compounds have been individuated as chemophenetic markers at different levels, such as cantleyoside, laciniatosides, sylvestrosides, GI-3, GI-5, oleonuezhenide, (Z)-aldosecologanin and centauroside. Only one hundred and fifty-nine bis-iridoids have been tested for their biological effects, including enzymatic, antioxidant, antimicrobial, antitumoral and anti-inflammatory. Sylvestroside I was the compound with the highest number of biological tests, whereas cantleyoside was the compound with the highest number of specific biological tests. Bis-iridoids have not always shown activity, and when active, their effectiveness values have been both higher and lower than the positive controls, if present. All these aspects have been deeply discussed in this paper, which also shows some critical issues and even suggests possible arguments for future research, since there is still a lot unknown about bis-iridoids.

In this paper, the first complete review on the seco-iridoids from the genus Jasminum L. was presented. In particular, their occurrence in the genus was detailed together with their biological activities. The literature survey has clearly pointed out that only a few Jasminum species have been studied for their seco-iridoid content evidencing oleoside derivatives as main compounds. In addition, the biological studies performed on them are very scarce focusing mainly on antioxidant and anti-inflammatory assays with modest effectiveness. All these results greatly underline the need for further in-depth analyses on these compounds under both the aspects.

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.

In this work, the first phytochemical analysis ever performed on a whole cone of Araucaria bidwillii Hook. is presented. This was carried out by means of column chromatography, NMR spectroscopy and MS spectrometry on the female cone, evidencing the presence of forty metabolites, thirty-three of which are primary whilst the remaining are non-volatile secondary. A chemophenetic evaluation was also performed reporting seven new compounds for the species i.e. β-sitosterol (5), 15-agathic acid methyl ester (6), methyl (E)-communate (7), shikimic acid (8), gallic acid (9), p-hydroxy-benzoic acid (10) and quinic acid (11). Throughout this evaluation some important qualitative phytochemical differences among this female cone, its seeds and the few other studied cones of the species comprised in the family, were evidenced. These whole results provide more information on the phytochemistry of this organ and of the species, in general, but also underline the need to perform more studies.

In this work, phytochemical analysis on different extracts of Roccella tinctoria DC. was reported using different techniques with respect to the past. Twenty volatile and three non-volatile compounds were identified, some of which were found in this species for the first time. The methanolic extracts and their non-volatile components were then evaluated for their antitumor effects in cancerous A549 and Mz-ChA-1 cells and for their tolerability in non-cancerous BEAS-2B and H69 cells, showing IC50 values from 94.6 µg/mL to 416.4 µg/mL, in general. The same extracts and compounds were also tested for their antifungal effects in Candida albicans, with only compound 2 being active, with an MIC50 value of 87 µg/mL. In addition, they were tested for their anti-Candida adhesion activity, anti-Candida biofilm formation, and anti-Candida mature biofilm inhibition, with efficacy percentages generally above 50% but not for all of them. Lastly, the DF3 extract and compounds 1–2 were tested in vivo according to the Galleria mellonella survival assay, showing positive mortality rates above 50% at different concentrations. All these biological assays were conducted on this species for the first time. Comparisons with other lichens and compounds were also presented and discussed.

In this paper, the first complete phytochemical analysis of an Italian specimen of Araucaria cunninghamii Mudie led to the identification of six secondary metabolites, one of which was identified in the species for the first time. The chemophenetic and ethnobotanical evaluations of this specimen are widely discussed.

Vinca sardoa (Stearn) Pignatti, known as Sardinian periwinkle, is widely diffused in Sardinia (Italy). This species contains indole alkaloids, which are known to have a great variety of biological activities. This study investigated the antileukemic activity against a B lymphoblast cell line (SUP-B15) of V. sardoa alkaloid-rich extracts obtained from plants grown in Italy, in Iglesias (Sardinia) and Rome (Latium). All the extracts showed a good capacity to induce reductions in cell proliferation of up to 50% at the tested concentrations (1–15 µg/mL). Moreover, none of the extracts showed cytotoxicity on normal cells at all the studied concentrations.

Pecan nuts (Carya illinoinensis (Wangenh.) K. Koch) contain the highest number of phytochemicals of all nuts, are a natural source of unsaturated fatty acids and other nutrients and can be considered an important addition to the Mediterranean diet al.though several studies have been carried out on pecans, employing several analytical techniques, no systematic study of the metabolic profile is available in literature. In this study, the metabolic profile of pecan nuts of three different cultivars was analysed by Nuclear Magnetic Resonance Spectroscopy. The cultivars compared were Wichita, Stuart, and Sioux, all grown in Italy in the same pedoclimatic conditions. 31 metabolites were identified and 28 were quantified and the three species were differentiated based on multivariate PCA analysis. The differences among them, and the levels of scutellarein and GABA, in particular, were attributed to the adaptation of the plants to the climate in their original areas.

This review article reports for the first time phytochemistry, ethnobotanical uses and pharmacological activities of all Cupressus L. species other than Cupressus sempervirens L. Indeed, the literature survey showed how many other Cupressus species are rich of important phytochemical compounds, widely used in the ethnobotanical field for several purposes and endowed with interesting biological activities, even if they are somehow neglected by the scientific community. This review aims to continue the study of these other Cupressus species and promote more research on them.