Alkaloids ofHaplophyllum foliosum

The alkaloids skimmianine, dubinidine, foliosidine, graveoline, and compounds (I) and (II) have been isolated from the epigeal part of the plantHaplophyllum foliosum Vved. (family Rutaceae). On the basis of the spectral characteristics of (I) and its 0-isopropylidene derivative it has been established that the compound is the alkaloid edulinine. Substance (II) was identified as ferulic acid by direct comparison with an authentic sample. This is the first time that edulinine and ferulic acid have been detected in plants of the genusHaplophyllum.     

Microprobe sampling—Photo ionization-time-of-flight mass spectrometry for in situ chemical analysis of pyrolysis and combustion gases: Examination of the thermo-chemical processes within a burning cigarette

A microprobe sampling device (μ-probe) has been developed for in situ on-line photo ionization mass spectrometric analysis of volatile chemical species formed within objects consisting of organic matter during thermal processing. With this approach the chemical signature occurring during heating, pyrolysis, combustion, roasting and charring of organic material within burning objects such as burning fuel particles (e.g., biomass or coal pieces), lit cigarettes or thermally processed food products (e.g., roasting of coffee beans) can be investigated. Due to its dynamic changes between combustion and pyrolysis phases the cigarette smoking process is particularly interesting and has been chosen as first application. For this investigation the tip of the μ-probe is inserted directly into the tobacco rod and volatile organic compounds from inside the burning cigarette are extracted and real-time analyzed as the glowing front (or coal) approaches and passes the μ-probe sampling position. The combination of micro-sampling with photo ionization time-of-flight mass spectrometry (PI-TOFMS) allows on-line intrapuff-resolved analysis of species formation inside a burning cigarette. Monitoring volatile smoke compounds during cigarette puffing and smoldering cycles in this way provides unparalleled insights into formation mechanisms and their time-dependent change. Using this technique the changes from pyrolysis conditions to combustion conditions inside the coal of a cigarette could be observed directly. A comparative analysis of species formation within a burning Kentucky 2R4F reference cigarette with μ-probe analysis reveals different patterns and behaviors for nicotine, and a range of semi-volatile aromatic and aliphatic species.     

Coelectroosmotic capillary electrophoresis of phenolic acids and derivatized amino acids using N,N-dimethylacrylamide-ethylpyrrolidine methacrylate physically coated capillaries

Two different families of compounds, i.e., phenolic and amino acids have been separated by capillary electrophoresis using a physically adsorbed polymer as capillary coating. The polymer used was N,N-dimethylacrylamide-ethylpyrrolidine methacrylate (DMA-EpyM) and it provided an stable coating by only flushing the capillary with a DMA-EpyM aqueous solution for 2 min between runs. The usefulness of this procedure has been demonstrated through the fast analysis of different families of solutes. Two different detection systems, diode-array detector and laser-induced fluorescence, have been used to determine phenolic acids and derivatized amino acids with fluorescein isothiocyanate, respectively. The main factors affecting reversal of electroosmotic flow (EOF) such as pH, type and concentration of buffer, and concentration and influence of organic solvents, as well as all the instrumental conditions were studied and optimized for both families of compounds.     

Toxicity testing of chemicals without use of animals

A series of publications on the studies of phytotoxicity of chemicals (pollutants, ecotoxicants), carried out by the author and his research group, have been reviewed. Tests (bioassays) based on experiments with many higher plant species, both terrestrial and aquatic ones (macrophytes), were used in these studies. Among the chemicals tested there were various organic (synthetic detergents, surfactants, and pesticides) and some inorganic (e.g., metal oxide nanoparticles) compounds. New methods for bioassay using plant species never used before have been developed by the author. New facts of phytotoxicity of a synthetic detergent have been discovered and reported. Specifically, an aqueous solution of liquid detergent Frosch (Werner & Mertz, FRG) at a concentration of 0.25 mL/L (and higher concentrations) inhibited the elongation rate of seedlings of Lens culinaris higher plant species. Also, phytotoxicity of synthetic cationic surfactant dodecyltrimethylammonium bromide has been reported for the first time. This surfactant at a concentration of 4 mg/L inhibited the elongation of Lens culinaris plant seedlings. The phytotesting methods contribute to the development of alternative approaches to studying the toxicity of chemicals through non-animal testing.     

One decade of research on ion-selective electrodes in Iran (1996–2006)

This review presents a general overview about the development of ion-selective electrodes in Iran during the past decade (1996–2006). All of the reported ion-selective sensors (for cations, anions and organic species) are cited in this review. Sensors for 39 cations, 12 anions, and 23 organic compounds and drugs have been reported in this reivew. Some of the main group cations (e.g. beryllium) as well as most of the lanthanide ion (i.e., presidium, erbium, lutetium, cerium, neodymium, europium, gadolinium, terbium, dysprosium, holmium, ytterbium, and thulium) sensors have been reported for the first time. It is noticable that the best reported sensors for HPO₄ ^2?, SO₄ ^2?, Cl^?, ClO₄ ^?, Br^?, and I₃ ^? have been designed and constructed by the Iranian researchers.     

Uncommon Terpenoids from Salvia Species: Chemistry,Biosynthesis and Biological Activities

The search for new bioactive compounds from plant sources has been and continues to be one of the most important fields of research in drug discovery. However, Natural Products research has continuously evolved, and more and more has gained a multidisciplinary character. Despite new developments of methodologies and concepts, one intriguing aspect still persists, i.e., different species belonging to the same genus can produce different secondary metabolites, whereas taxonomically different genera can produce the same compounds. The genus Salvia L. (Family Lamiaceae) comprises myriad distinct medicinal herbs used in traditional medicine worldwide that show different pharmacological activities due to the presence of a variety of interesting specialized metabolites, including mono-, sesqui-, di-, sester-, tri-, tetra-, and higher terpenoids as well as phenylpropanoids, phenolic acid derivatives, lignans, flavonoids, and alkaloids. We herein summarize the research progress on some uncommon terpenoids, isolated from members of the genus Salvia, which are well recognized for their potential pharmacological activities. This review also provides a current knowledge on the biosynthesis and occurrence of some interesting phytochemicals from Salvia species, viz. C₂₃-terpenoids, sesterterpenoids (C₂₅), dammarane triterpenoids (C₃₀), and uncommon triterpenoids (C₂₀+C₁₀). The study was carried out by searching various scientific databases, including Elsevier, ACS publications, Taylor and Francis, Wiley Online Library, MDPI, Springer, Thieme, and ProQuest. Therefore, 106 uncommon terpenoids were identified and summarized. Some of these compounds possessed a variety of pharmacological properties, such as antibacterial, antiviral, antiparasitic, cytotoxic and tubulin tyrosine ligase inhibitory activities. Due to the lack of pharmacological information for the presented compounds gathered from previous studies, biological investigation of these compounds should be reinvestigated.     

A simple accurate model for prediction of deflagration temperature of energetic compounds

A novel general method is introduced to predict deflagration temperature of organic energetic compounds containing at least –NNO₂, –ONO₂, or –CNO₂ groups. Deflagration temperature is an important safety parameter in working with dangerous energetic compounds and their environmental problems. It is shown that the contribution of some molecular structure parameters can be used to interpret thermal decomposition of an energetic compound. For 86 energetic materials (corresponding to 102 measured values) with different molecular structures, the new correlation has the root mean square (rms) and the average deviations of 23.8 and 19.0 K, respectively. The new method is also tested for some energetic compounds with complex molecular structures, e.g., two new organic energetic molecules N,N′-bis(1,2,4-triazol-3yl)-4,4′-diamino-2,2′,3,3′,5,5′,6,6′-octanitroazobenzene (BTDAONAB) and 2,4,6-trinitrophloroglucinol.     

Diversity of Volatile Compounds in Ten Varieties of Zingiberaceae

Zingiberaceae plants are distributed in the tropical and subtropical regions of the world, being used in many famous medicinal materials. Meanwhile, some Zingiberaceae plants are important horticultural flowers because they are green all year round and have special aromas. To conduct an extensive investigation of the resources of Zingiberaceae plants, the volatile compounds of ten species of Zingiberaceae were extracted and analyzed by GC–MS, including Costus comosus var. bakeri (K.Schum.) Maas, Curcuma rubescens Roxb., Curcuma aeruginosa Roxb., Curcuma attenuata Wall., Hongfengshou, Hedychium coronarium Koeng, Zingiber zerumbet (L.) Smith, Hedychium brevicaule D. Fang, Alpinia oxyphylla Miq., and Alpinia pumila Hook.F. A total of 162 compounds were identified, and most of those identified were monoterpenes and sesquiterpenes. (E)-labda-8(17),12-diene-15,16-dial, n-hexadecanoic acid, 4-methoxy-6-phenethyl-2H-pyran-2-one, and L-β-pinene were found in high concentrations among the plants. These ten species of Zingiberaceae contained some of the same volatiles, but their contents were different. Pharmacological effects may be associated with the diversity of volatiles in these ten plants.     

Indirect radiotracer study of the adsorption of organic compounds at platinized platinum electrodes

The possibility of the use of an indirect radiotracer method for the study of the adsorption of organic species has been discussed. It has been shown that by study of the adsorption of Cl-36 labelled chloride ions in the presence of organic species such as maleic, benzoic and m-nitrobenzoic acids there is a possibility of obtaining information concerning the adsorption of the latter compounds. Change in the adsorption behaviour of organic species connected with their electroreduction were detected and followed by indirect tracer measurements. In the light of the experimental results, some mechanistic aspects of the reduction of aromatic nitro compounds are discussed.     

Alkaloids ofHaplophyllum foliosum. II.

In addition to the alkaloids known previously from this plant, haplofoline and folifine, from the epigeal part ofHaplophyllum foliosum we have isolated norgraveoline with mp 288–289°C (decomp. from acetone), and myrtopsine with mp 201–202°C (from chloroform), [α]_D-5° (c 0.05; methanol), which were first obtained fromHaplophyllum dubium andMyrtopsis sellingii, respectively. We have confirmed by the PMR-spectroscopic method the positions of the substituents in the dihydrofuran ring of myrtopsine suggested previously on the basis of biogenetic considerations. In addition, it has been established that the substituents are present in the trans form. This is the first time that myrtopsine has been detected in plants of the genusHaplophyllum.     

Dechlorane Plus and related compounds in aquatic and terrestrial biota: a review

Dechlorane Plus, dechlorane 602, dechlorane 603 and dechlorane 604 are flame retardants that have been used for a long time as a substitute for mirex, but they have not been noticed as environmental contaminants until recently (2006). Regardless of their large molecular size and very high lipophilicity (log K _OW?>?9), Dechlorane Plus and related compounds have been detected in different aquatic and terrestrial species, supporting their bioaccumulation and biomagnification. Moreover, some studies showed different behaviour of the syn-Dechlorane Plus and anti-Dechlorane Plus isomers in the environment and different biomagnification factors in biota. This review describes the different analytical approaches applied to the determination of Dechlorane Plus and related compounds. Moreover, a summary of their levels in aquatic and terrestrial biota, as well as in humans, is presented, showing also current research results on their bioaccumulation and biomagnification potential. Finally, isomer-specific bioaccumulation of Dechlorane Plus is also discussed.     

Comparative phytotoxicity of methylated and inorganic arsenic- and antimony species to Lemna minor, Wolffia arrhiza and Selenastrum capricornutum

The alkylation of metalloids through the transfer of methyl groups is an important factor in the biogeochemical cycling of elements like arsenic and antimony. In the environment, many different organic and inorganic forms of these elements can therefore be found in soils, sediments or organisms. Studies that compare the ecotoxicity of these different chemical species however are rare. Therefore, this study aimed to generate toxicity data on two scarcely studied organic compounds of arsenic and antimony, as well as to compare their toxicity to the inorganic species, which are studied so far to a higher extent, in order to improve the environmental effect assessment of these elements. To this purpose, bioassays were performed in which three different aquatic organisms (the floating water plants Lemna minor and Wolffia arrhiza and the green alga Selenastrum capricornutum) were exposed to a concentration series of 3 different arsenic species (sodium arsenite — As(III), sodium arsenate — As(V), and monomethylarsonous diiodide — MMAs(III)) and three different antimony species (antimony potassium tartrate hydrate — Sb(III), potassium hexahydroxoantimonate — Sb(V), trimethylantimony(V) bromide — TMSb(V). The observed effect concentrations demonstrated that the inorganic (III)- and (V)-valent species of arsenic were clearly more toxic than the corresponding antimony species. The highest overall toxicity has been shown by MMAs(III) followed by the inorganic As(III). The highest toxicity of the three tested antimony species has been observed for TMSb(V). The observed differences in effect levels stress the importance once more that speciation must not be ignored in toxicity studies.     

Ruta Essential Oils: Composition and Bioactivities

Ruta L. is a typical genus of the citrus family, Rutaceae Juss. and comprises ca. 40 different species, mainly distributed in the Mediterranean region. Ruta species have long been used in traditional medicines as an abortifacient and emmenagogue and for the treatment of lung diseases and microbial infections. The genus Ruta is rich in essential oils, which predominantly contain aliphatic ketones, e.g., 2-undecanone and 2-nonanone, but lack any significant amounts of terpenes. Three Ruta species, Ruta chalepensis L., Ruta graveolens L., and Ruta montana L., have been extensively studied for the composition of their essential oils and several bioactivities, revealing their potential medicinal and agrochemical applications. This review provides a systematic evaluation and critical appraisal of publications available in the literature on the composition and bioactivities of the essential oils obtained from Ruta species and includes a brief outlook of the potential applications of nanotechnology and chitosan-based products of Ruta essential oils.     

Antioxidant Metabolites in Primitive,Wild, and Cultivated Citrus and Their Role in Stress Tolerance

The genus Citrus contains a vast range of antioxidant metabolites, dietary metabolites, and antioxidant polyphenols that protect plants from unfavorable environmental conditions, enhance their tolerance to abiotic and biotic stresses, and possess multiple health-promoting effects in humans. This review summarizes various antioxidant metabolites such as organic acids, amino acids, alkaloids, fatty acids, carotenoids, ascorbic acid, tocopherols, terpenoids, hydroxycinnamic acids, flavonoids, and anthocyanins that are distributed in different citrus species. Among these antioxidant metabolites, flavonoids are abundantly present in primitive, wild, and cultivated citrus species and possess the highest antioxidant activity. We demonstrate that the primitive and wild citrus species (e.g., Atalantia buxifolia and C. latipes) have a high level of antioxidant metabolites and are tolerant to various abiotic and biotic stresses compared with cultivated citrus species (e.g., C. sinensis and C. reticulata). Additionally, we highlight the potential usage of citrus wastes (rag, seeds, fruit peels, etc.) and the health-promoting properties of citrus metabolites. Furthermore, we summarize the genes that are involved in the biosynthesis of antioxidant metabolites in different citrus species. We speculate that the genome-engineering technologies should be used to confirm the functions of candidate genes that are responsible for the accumulation of antioxidant metabolites, which will serve as an alternative tool to breed citrus cultivars with increased antioxidant metabolites.     

Exploring the Volatiles Released from Roots of Wild and Domesticated Tomato Plants under Insect Attack

Plants produce volatile organic compounds that are important in communication and defense. While studies have largely focused on volatiles emitted from aboveground plant parts upon exposure to biotic or abiotic stresses, volatile emissions from roots upon aboveground stress are less studied. Here, we investigated if tomato plants under insect herbivore attack exhibited a different root volatilome than non-stressed plants, and whether this was influenced by the plant’s genetic background. To this end, we analyzed one domesticated and one wild tomato species, i.e., Solanum lycopersicum cv Moneymaker and Solanum pimpinellifolium, respectively, exposed to leaf herbivory by the insect Spodoptera exigua. Root volatiles were trapped with two sorbent materials, HiSorb and PDMS, at 24 h after exposure to insect stress. Our results revealed that differences in root volatilome were species-, stress-, and material-dependent. Upon leaf herbivory, the domesticated and wild tomato species showed different root volatile profiles. The wild species presented the largest change in root volatile compounds with an overall reduction in monoterpene emission under stress. Similarly, the domesticated species presented a slight reduction in monoterpene emission and an increased production of fatty-acid-derived volatiles under stress. Volatile profiles differed between the two sorbent materials, and both were required to obtain a more comprehensive characterization of the root volatilome. Collectively, these results provide a strong basis to further unravel the impact of herbivory stress on systemic volatile emissions.     

Fermentation condition outweighed truffle species in affecting volatile organic compounds analyzed by chromatographic fingerprint system

The influences of fermentation conditions and truffle species (i.e., Tuber melanosporum, Tuber sinense, Tuber indicum, and Tuber aestivum) on the volatile organic compounds (VOCs) originated from truffle fermentation mycelia were studied by using chromatographic fingerprint system for the first time. Gas chromatography combined with statistical methods including similarity analysis and hierarchical cluster analysis was applied to develop chromatographic fingerprint system for truffle VOCs evaluation. Fermentation conditions affected the VOCs from truffle fermentation mycelia much more significantly than truffle species. This indicated that it is possible to adjust the aroma of truffle fermentation mycelia similar with the natural fruiting-body through the control of fermentation process.     

Determination of polyphenolic compounds by liquid chromatography–mass spectrometry in Thymus species

Polyphenolic compounds represent a wide group of phytochemicals, including well-known subgroups of phenolic acids, flavonoids, natural dyes, lignans etc., which are produced by plants. These natural bioactive compounds possess a variety of beneficial effects including antioxidant and anticarcinogenic activities, protection against coronary diseases as well as antimicrobial properties. Thymus species have already been reported as sources of different phenolic acids and flavonoids. Moreover, the composition and content of flavonoids in Thymus species play important role as taxonomic markers providing distinction of species. High-performance liquid chromatography (HPLC) coupled with diode array detector (DAD) and on-line mass spectrometry (ESI-MS) method was used for analysis. The method was evaluated for a number of validation characteristics (repeatability and intermediate precision, LOD, LOQ, calibration range, and recovery). The polyphenolic pattern of five native Hungarian Thymus species (T. glabrescens Willd., T. pannonicus All., T. praecox Opiz, T. pulegioides L., and T. serpyllum L.) was characterized. The dominant compound was rosmarinic acid, which ranged between 83.49 μg g⁻¹ and 1.436 mg g⁻¹. Other phenolic acids (ferulic acid, caffeic acid and its other derivatives, chlorogenic acid and p-coumaric acids) were present in every examined Thymus species, as well as flavanones: naringenin, eriodictyol and dihydroquercetin; flavones: apigenin and apigenin-7-glucoside, flavonols: quercetin and rutin. The polyphenolic pattern was found to be a useful additional chemotaxonomic tool for classification purposes and determination of the locality of origin.     

Secondary Formation of Aromatic Nitroderivatives of Environmental Concern: Photonitration Processes Triggered by the Photolysis of Nitrate and Nitrite Ions in Aqueous Solution

Aromatic nitroderivatives are compounds of considerable environmental concern, because some of them are phytotoxic (especially the nitrophenols, and particularly 2,4-dinitrophenol), others are mutagenic and potentially carcinogenic (e.g., the nitroderivatives of polycyclic aromatic hydrocarbons, such as 1-nitropyrene), and all of them absorb sunlight as components of the brown carbon. The latter has the potential to affect the climatic feedback of atmospheric aerosols. Most nitroderivatives are secondarily formed in the environment and, among their possible formation processes, photonitration upon irradiation of nitrate or nitrite is an important pathway that has periodically gained considerable attention. However, photonitration triggered by nitrate and nitrite is a very complex process, because the two ionic species under irradiation produce a wide range of nitrating agents (such as ^•NO₂, HNO₂, HOONO, and H₂OONO⁺), which are affected by pH and the presence of organic compounds and, in turn, deeply affect the nitration of aromatic precursors. Moreover, aromatic substrates can highly differ in their reactivity towards the various photogenerated species, thereby providing different behaviours towards photonitration. Despite the high complexity, it is possible to rationalise the different photonitration pathways in a coherent framework. In this context, this review paper has the goal of providing the reader with a guide on what to expect from the photonitration process under different conditions, how to study it, and how to determine which pathway(s) are prevailing in the formation of the observed nitroderivatives.     

Neuroprotective Activities of Crossyne flava Bulbs and Amaryllidaceae Alkaloids: Implications for Parkinson’s Disease

Parkinson’s disease (PD) is one of the most common neurodegenerative diseases and affects approximately 6.3 million people worldwide. To date, the treatment of PD remains a challenge, as available treatment options are known to be associated with serious side effects; hence, the search for new treatment strategies is critical. Extracts from the Amaryllidaceae plant family as well as their alkaloids have been reported to have neuroprotective potentials. This study, therefore, investigated the biological activities of Crossyne flava and its isolated alkaloids in an in vitro MPP⁺ (1-methyl-4-phenylpyridinium) PD model using SH-SY5Y cells. The effects of the total extract as well as the four compounds isolated from Crossyne flava (i.e., pancratinine B (1), bufanidrine (2), buphanisine (3), and epibuphanisine (4)) were evaluated for cell viability, neuroprotection, levels of reactive oxygen species (ROS), adenosine triphosphate activity (ATP), and caspase 3/7 activity in SH-SY5Y cells. The results obtained showed that pre-treatment with both the extract and the isolated compounds was effective in protecting the SH-SY5Y cells from MPP⁺-induced neurotoxicity and inhibited ROS generation, ATP depletion as well as apoptosis induction in the SH-SY5Y cells. The results of this study show that the Amaryllidaceae plant family may be a source of novel compounds for the treatment of neurodegenerative diseases, which validates the reported traditional uses.     

Chemical and Bioactive Characterization of the Essential Oils Obtained from Three Mediterranean Plants

Cupressus sempervirens L., Juniperus communis L. and Cistus ladanifer L. are Mediterranean arboreal and shrub species that possess essential oils (EO) in their leaves and branches. This study aimed at characterizing the EOs obtained by steam distillation from the three species collected in different locations from Spain (Almazán, Andévalo, Barriomartín, Cerezal, Ermitas and Huéscar). For this purpose, volatiles composition was determined by GC-MS, and different bioactivities were evaluated. The highest content in terpenes was observed in C. sempervirens (Huéscar origin) followed by J. communis (Almazán origin), corresponding to 92% and 91.9% of total compounds, respectively. With exception of C. ladanifer from Cerezal that presented viridiflorol as the most abundant compound, all the three species presented in common the α-pinene as the major compound. The EOs from C. ladanifer showed high antibacterial potential, presenting MIC values from 0.3 to 1.25 mg/mL. Concerning other bioactivities, C. ladanifer EO revealed an oxidation inhibition of 83%, while J. communis showed cytotoxicity in the MCF-7 cell line, and C. sempervirens and C. ladanifer EOs exhibited the highest potential on NCI-H460 cell lines. Nevertheless, some EOs revealed toxicity against non-tumoral cells but generally presented a GI₅₀ value higher than that of the tumor cell lines.