Chemical constituents and medicinal properties of Allium species

Allium species, belonging to Alliaceae family, are among the oldest cultivated vegetables used as food. Garlic, onions, leeks and chives, which belong to this family, have been reported to have medicinal properties. The Allium species constituents have been shown to have antibacterial and antioxidant activities, and, in addition, other biological properties. These activities are related to their rich organosulfur compounds. These organosulfur compounds are believed to prevent the development of cancer, cardiovascular, neurological, diabetes, liver diseases as well as allergy and arthritis. There have also been reports on toxicities of these compounds. The major active compounds of Allium species includes, diallyl disulfide, diallyl trisulfide, diallyl sulfide, dipropyl disulfide, dipropyl trisulfide, 1-propenylpropyl disulfide, allyl methyl disulfide and dimethyl disulfide. The aim of this review is to focus on a variety of experimental and clinical reports on the effectiveness, toxicities and possible mechanisms of actions of the active compounds of garlic, onions, leek and chives.

     

Aspects of interspecific hybridization within edible <Emphasis Type="Italic">Alliaceae</Emphasis>

Crossing experiments within the genus Allium have been carried out for many years. Usually, with the aim of widening genetic variation, edible Alliaceae such as bulb onion, Japanese bunching onion, leek, garlic and shallot have been crossed with each other or with distant vegetable Allium crops. Interspecific hybridization, especially with wild relatives is considered as the best way of introgression desirable traits to the crops. By using sexual or somatic hybridization, many important characters, such as: disease and pest resistance, important metabolites and cytoplasmic male sterility have been transferred to other Allium crops. This review summarises some aspects of the directions of interspecific hybridization in edible Alliaceae and the significance and perspectives of using these hybrids in breeding programmes.     

Quercetin-4′-glucoside: a physiological inhibitor of the activities of dominant glutathione <Emphasis Type="Italic">S</Emphasis>-transferases in onion (<Emphasis Type="Italic">Allium cepa</Emphasis> L.) bulb

The onion (Allium cepa L.) bulb has a high level of glutathione S-transferase (GST) activity, and it is a rich source of sulfur compounds as well as flavonoids. To investigate interactions between onion bulb GSTs and metabolites, we separated onion bulb GSTs (GSTa and GSTb as minor GSTs and GSTc, GSTd and GSTe as dominant GSTs) by DEAE-cellulose chromatography. In Western blot analysis with anti-CmGSTF1 antiserum, GSTc and GSTd fractions showed a thick band. A cDNA (AcGSTF1) corresponding to GSTc was immunoscreened with the same antiserum from an onion bulb cDNA library and its bacterial expression product was also subjected to investigation. Among the sulfur compounds, nonphysiological compounds, S-hexyl glutathione (GSH) and S-butyl GSH, showed strong inhibitory effects on 1-chloro-2,4-dinitrobenezene (CDNB)-conjugating activities of GSTa, GSTb and GSTe. However, physiological sulfur compounds, S-methyl GSH, S-propyl GSH, S-lactoyl GSH and S-ethyl-l-cysteine sulfoxide, had small or almost no inhibitory effects. Therefore, onion sulfur compounds might have the least possibility to be substantial inhibitors of onion GSTs. On the other hand, the activities of GSTc, GSTd and AcGSTF1 were strongly inhibited by flavonoids, quercetin, luteolin, apigenin and kaempferol. Ethylacetate (EtOAc) extract of onion bulb contained quercetin-4′-glucoside as a major inhibitory substance. The strong inhibitory effects of quercetin-4′-glucoside on GSTc and GSTd as well as on AcGSTF1 (50% inhibitory concentration (IC₅₀): 9.5, 7.5 and 11.2 μM, respectively) along with its high concentration (226 μM) in the onion bulb indicates that quercetin-4′-glucoside is a physiological inhibitor of dominant GSTs in the onion bulb.     

Phylogenetic relationships among cultivated Allium species from restriction enzyme analysis of the chloroplast genome

Summary The genus Allium contains many economically important species, including the bulb onion, chive, garlic, Japanese bunching onion, and leek. Phylogenetic relationships among the cultivated alliums are not well understood, and taxonomic classifications are based on relatively few morphological characters. Chloroplast DNA is highly conserved and useful in determining phylogenetic relationships. The size of the chloroplast genome of Allium cepa was estimated at 140 kb and restriction enzyme sites were mapped for KpnI, PstI, PvuII, SalI, XbaI, and XhoI. Variability at restriction enzyme sites in the chloroplast DNA was studied for at least three accessions of each of six cultivated, old-world Allium species. Of 189 restriction enzyme sites detected with 12 enzymes, 15 mutations were identified and used to estimate phylogenetic relationships. Cladistic analysis based on Wagner and Dollo parsimony resulted in a single, most-parsimonious tree of 16 steps and supported division of the species into sections. Allium species in section Porrum were distinguished from species in sections Cepa and Phyllodolon. Two species in section Rhiziridium, A. schoenoprasum and A. tuberosum, differed by five mutations and were placed in separate lineages. Allium cepa and A. fistulosum shared the loss of a restriction enzyme site and were phylogenetically closer to each other than to A. schoenoprasum. This study demonstrates the usefulness of restriction enzyme site analysis of the chloroplast genome in the elucidation of phylogenetic relationships in Allium.     

Comparative study of antioxidant capacity in organs of different Allium species

Cultivated and wild Allium species were investigated in order to compare the antioxidant capacity of their leaves and bulbs. Leaf and bulb anti-oxidative enzymes and scavenger activities, along with quantities of non-enzymic antioxidants, malonyl-dialdehyde and OH radicals were determined. Results obtained suggest that leaves possess higher anti-oxidant and scavenging activities than bulbs in the majority of cultivated and wild Allium species examined. Cultivation of some wild species such as A. flavum L., A. schoenoprasum L. and A. ursinum L. could be conducted in the future in order to produce Allium species with high antioxidant capacity in leaves and bulbs.     

Bulb tunic anatomy and its taxonomic implication in Allium L. (Amaryllidaceae: Allioideae)

Abstract

Allium is taxonomically a difficult genus with blurred taxonomic borders at all taxonomic ranks. In this research, anatomy and morphology of bulb tunics in 42 species of the genus representing its 16 currently recognized sections and 6 subgenera (Allium, Cepa, Reticulatobulbosa, Amerallium, Polyprason and Melanocrommyum) were investigated. Our results indicated the following characters to be most informative at sectional and subgeneric levels: features of calcium oxalate crystals and subepidermal cell layer of the outermost bulb tunic, type of tracheids, and bulbils presence. Three main types of crystals, i.e. prismatic, sand and druses, were fairly common among the investigated species except for the members of A. sect. Acanthoprason (A. subg. Melanocrommyum) that often lack crystals. The subepidermal layers of outer tunics were mostly composed of hexagonal, rectangular, or elongated cells but A. paradoxum (A. subg. Amerallium, sect. Briseis) showed the pentagonal type and A. longisepalum (A. subg. Amerallium, sect. Molium) the elliptic type of subepidermal cells. The members of A. sub. Melanocrommyum showed various types of tunic cells and crystals.     

LATICIFERS IN THE BULB SCALES OF ALLIUM

The structure and distribution of laticifers has been studied in the bulb scales of 52 species and varieties of Allium. Differences in laticifer position, shape, and pitting in the cross wall of the observed specimens support Traub's separation of the subgenera Amerallium and Allium within the genus Allium. If the species examined are representative, anatomical evidence also justifies the distinction of the section Melanocrommyum and the subsection Cepa.     

Pollen morphology and phylogenetic analysis of Eperua Aublet (Detarieae: Caesalpinioideae: Leguminosae)

The diverse pollen morphology of fourteen species of the genus Eperua is described and illustrated using light, scanning electron and transmission electron microscopy. Six pollen types are described and a key for their identification is provided. A cladistic analysis was carried out using macromorphological and palynological characters to form a hypothesis of relationships between taxa. The pollen morphology is discussed with regard to systematic relationships, function and phylogenetic significance of certain pollen morphological structures within the genus.     

Astragalus raphaelis (Fabaceae), a critical species from Sicily and taxonomic remarks on A. sect. Sesamei

The taxonomic position of Astragalus raphaelis, a rare and misappreciated species endemic to Sicily, has been examined. In addition, its geographical distribution, ecology and conservation status, diagnostic morphological characters, pod and seed micro‐morphology and relationship with A. stella are provided. Phenetic and phylogenetic trees (based on morphological data) for A. sect Sesamei shows that A. raphaelis is a taxonomically quite isolated species, with some relationships to A. sesamoides.     

Taxonomic revision of the genus Heliotropium (Boraginaceae s.l.) in south Yemen

The flora and fauna of Arabia, particularly southern Yemen, has recently attracted the interest of many authors. In this study, the genus Heliotropium L. (Boraginaceae) is taxonomically revised in southern Yemen. Ten species are recognized. Nomenclature, typification, representative specimens and a diagnostic key to all species are provided, along with their distribution in southern Yemen. The taxonomically most valuable characters in the genus are those of flowers (calyx, corolla, androecium and gynoecium) and nutlets, and those characters are thoroughly investigated and discussed. Both light and scanning microscopy are used in the investigation. Papillate anther apices (brush‐like) were recognized in some species. Connate anthers and deep or shallow ventral circular depressions on the nutlets were found to be useful in distinguishing members of H. sect. Orthostachys (viz. H. strigosum, H. rariflorum and H. ovalifolium), while winged nutlets were found only in H. pterocarpum. The length and hairiness of the style and stigma also proved to be taxonomically useful.     

Seed testa micromorphology of thirty‐eight species of Allium (Amaryllidaceae) from central Asia,and its taxonomic implications

Micromorphological characteristics of the seed testa of 38 species belonging to 19 sections and seven subgenera of Allium from central Asia have been evaluated with a scanning electron microscope (SEM). Several taxonomically significant characters were found. The results showed that the epidermis consists of polygonal cells with different dimensions, that the cellular arrangement is tight or loose with or without reticulate tissue, and that the arrangement of cells is regular or irregular. The main variation was found in the anticlinal walls, of which the outline could be straight, straight to arched, arched or undulating like an S or U. Convex and (or) concave verrucate periclinal walls occurred in all species investigated. Based on the characteristics of the anticlinal and periclinal walls of the 38 species, six groups of Allium were distinguished, and a dichotomous key for them is presented. The cellular arrangement and periclinal and anticlinal wall traits of the 38 species of Allium were found stable and distinct within a species, but showed great differences among species. We conclude that seed epidermal characteristics provide useful and important information for distinguishing species of Allium, and thus they have taxonomic significance.     

Artemisinin-indole and artemisinin-imidazole hybrids: Synthesis,cytotoxic evaluation and reversal effects on multidrug resistance in MCF-7/ADR cells

A series of artemisinin derivatives with MDR reversal activity were designed and synthesized. All hybrids were screened to anticancer activities against four human cancer cell lines (A549, MCF-7, HepG-2, MDA-MB-231) and normal human hepatic cell (L02) in vitro. Most of the new compounds showed higher anticancer activities than artemisinin, among which compounds 11a and 11c displayed superior potency with IC₅₀ 6.78?μM and 5.25?μM against MCF-7, respectively. The further research indicated that the most potent 11c induced cell cycle arrest at G2 phase in MCF-7. Additionally, compound 11c showed remarkable MDR reversal activity which reversed adriamycin against MCF-7/ADR cells with IC₅₀ 0.76?μM.     

蒲公英抗肿瘤活性部位的GC-MS分析研究

目的：考察蒲公英提取物对MCF-7增殖作用的影响,研究蒲公英抗肿瘤活性部位的化学成分。方法：采用MTT法比较蒲公英水提物、醇提物和不同极性提取物对MCF-7增殖的影响;以气相色谱．质谱（GC-MS）联用技术对具有抑制MCF-7人乳腺癌细胞增殖的部位进行分离和鉴定。结果：蒲公英水提物和醇提物对MCF-7细胞均有抑制作用,体外最大抑制率分别达到92．95％、93．59％,蒲公英不同极性溶剂提取物中,氯仿部位抑制MCF-7的增殖,且抑制作用高于醇提和水提物,乙酸乙酯和石油醚部位促进MCF-7的增殖。从蒲公英氯仿提取物中鉴定出80种化合物,占其总量的98．07％。结论：蒲公英氯仿部位具有抗肿瘤活性,为蒲公英抗肿瘤活性成分的研究提供了依据,拓展了筛选中药活性成分的方法。     

Discrimination amongst Alliums using an electronic nose

Pyruvic acid content determination and, to lesser extents, thiosulphinates determination and organoleptic tests are used for assessing the eating characteristics of onions and other Allium spp. Each of these methods has inherent limitations, especially when large numbers of samples are to be evaluated. With a view to developing a more convenient quality evaluation method, an electronic nose was used to discriminate flavour and aroma characteristics amongst garlic, leek, shallot, bulb onion and spring onion. Differences in relative sensor response to headspace volatiles over macerated samples of these five different Allium types were recorded. Principal Component Analysis (PCA) showed some separation among the five types. PCA and Mahalanobis' D² statistic suggested similarities in headspace volatiles for shallot, spring and bulb onions and differences for leek and, especially, garlic. Multiple linear regression analyses (Y =α+β₁X₁+β₁X₂; N_{(x, Y)}=5) of the first two principal component values (PCA 1 [X₁] and PCA 2 [X₂]) accounted for not less than 90% of the total variation in pyruvic acid concentration (Y1), total soluble solids content (Y2) and percentage dry matter content (Y3) of the Allium types. These relationships suggest that electronic nose discrimination was on the basis of quality characteristics that relate to Allium flavour. This work has shown that the electronic nose has potential for flavour characteristic‐based discrimination amongst Allium types. Future work will explore this potential within a single Allium spp.     

Synthesis,anticancer and antioxidant activities of some novel N-(benzo[d]oxazol-2-yl)-2-(7- or 5-substituted-2-oxoindolin-3-ylidene) hydrazinecarboxamide derivatives

A series of N-(benzo[d]oxazol-2-yl)-2-(7- or 5-substituted-2-oxoindolin-3-ylidene) hydrazinecarboxamide derivatives were synthesized by treating N-(benzoxazol-2-yl)hydrazinecarboxamide with different isatin derivatives. The newly synthesized compounds were characterized on the basis of spectral analyses. All the synthesized derivatives (Va-l) were screened for anticancer and antioxidant activities. The results showed the anticancer activity of test compounds against HeLa, IMR-32 and MCF-7 cancer cell lines using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. All the synthetic compounds produced a dose-dependant inhibition of growth of the cells. The IC₅₀ values of some compounds were comparable with standard anticancer agent, cisplatin. All the title compounds effectively scavenged the free radical, α,α-diphenyl-β-picryl hydrazyl. The test compounds having substitution with different halides (electron withdrawing groups) at C5 position showed more potent anticancer and antioxidant activities than those at C7 position. These results indicate that C5-substituted derivatives may be useful for developing antioxidant agents that play a protective role in many pathological conditions such as cancer, diabetes and so on.     

Antiproliferative activity of some 1,4-dimethylcarbazoles on cells that express estrogen receptors: part I

Several 9H-carbazole derivatives are used for various pharmacological applications. Many of these compounds demonstrated cytotoxic and anticancer activities. In this work, we have investigated the cytotoxic activity of some substituted carbazoles against cancer cell lines (MCF-7, and ISK). The derivative 2a showed the highest inhibitory activity against both cell lines.     

The micromorphologies of seed coats and petal trichomes of the taxa of Viola subsect. Boreali-Americanae (Violaceae) and their utility in discerning orthospecies from hybrids

Viola subsect.Boreali-Americanae, confined to North America including northern México, has long been considered one of the most taxonomically difficult temperate groups of the angiosperms. Hybridization, followed in some localities by introgression, has made it difficult for systematists to discern the “core” species by using only standard macromorphological characters. Analyses that employed scanning electron microscopy (SEM) of seed coats and petal trichomes generated new characters. SEM of the surface of seeds of each of the orthospecies revealed a suite of primary and secondary sculpture characters unique to each species that are correlated with a suite of macromorphological characters. In a number of species, SEM of petal trichomes provided additional unique characters. SEM of the surface of seed coats enabled, also, the identification of instances of hybridization by revealing blends of structures of the primary and secondary sculpture typical of different orthospecies and instances of putative introgression by revealing deviations in surface structures from those typical of orthospecies. A procedure based on iterative examinations of macromorphology and micromorphology, which was developed in this research, enable the discernment of hybrids and putative introgressants. Combining the micromorphological and macromorphological data with ecological and phytogeographical data enabled the delimitation of sixteen orthospecies.     

Bioactive Saponins from Allium and Aster Plants

Plants belonging to the genera Allium and Aster are widely distributed in nature and have been used as food and/or medicine. Their wide use was mainly due to the medicinal properties attributed to these plants since ancient times, recently supported by epidemiological and laboratory studies. Saponin compounds, responsible for many pharmacological activities, are quite abundant in these plants. Thus, a deep knowledge about the saponin composition of these vegetables appears to be essential and could promote the discovery of new potential leads. As part of our continuing research aimed at the identification of bioactive metabolites, we have addressed our attention to several Allium and Aster species. The study resulted in the isolation of over fifty saponins of furostane, spirostane, cholestane, and oleane-type structures. Some of the isolated compounds exhibited promising antiproliferative, antifungal, and antispasmodic activities. Their structure, distribution and bioactivity will be reported here together with a brief overview of the literature on Allium and Aster saponins.     

Steroidal saponins from the genus <Emphasis Type="Italic">Allium</Emphasis>

Steroidal saponins are widely distributed among monocots, including the Amaryllidaceae family to which the Allium genus is currently classified. Apart from sulfur compounds, these are important biologically active molecules that are considered to be responsible for the observed activity of Allium species, including antifungal, cytotoxic, enzyme-inhibitory, and other. In this paper, literature data concerning chemistry and biological activity of steroidal saponins from the Allium genus has been reviewed.