Biodiversity of Convolvulaceous species that contain ergot alkaloids,indole diterpene alkaloids,and swainsonine

Convolvulaceous species have been reported to contain several bioactive principles thought to be toxic to livestock including the calystegines, swainsonine, ergot alkaloids, and indole diterpene alkaloids. Swainsonine, ergot alkaloids, and indole diterpene alkaloids are produced by seed transmitted fungal symbionts associated with their respective plant host, while the calystegines are produced by the plant. To date, Ipomoea asarifolia and Ipomoea muelleri represent the only Ipomoea species and members of the Convolvulaceae known to contain indole diterpene alkaloids, however several other Convolvulaceous species are reported to contain ergot alkaloids. To further explore the biodiversity of species that may contain indole diterpenes, we analyzed several Convolvulaceous species (n = 30) for indole diterpene alkaloids, representing four genera, Argyreia, Ipomoea, Stictocardia, and Turbina, that had been previously reported to contain ergot alkaloids. These species were also verified to contain ergot alkaloids and subsequently analyzed for swainsonine. Ergot alkaloids were detected in 18 species representing all four genera screened, indole diterpenes were detected in two Argyreia species and eight Ipomoea species of the 18 that contained ergot alkaloids, and swainsonine was detected in two Ipomoea species. The data suggest a strong association exists between the relationship of the Periglandula species associated with each host and the occurrence of the ergot alkaloids and/or the indole diterpenes reported here. Likewise there appears to be an association between the occurrence of the respective bioactive principle and the genetic relatedness of the respective host plant species.     

Chemotaxonomy and Resource Utilization of the Tribe Chelidonieae (Papaveraceae)

The tribe Chelidonieae of Papaveraceae, consists of 8 genera and 23 species in the world. Most species belonging to this taxon contain dominantly biologically active substances and are widely used as medicinal plants. A chemotaxonomic study in this tribe reveals that Chelidonieae is linked to the other tribes in the presence of protopine-type alkaloids, and the ubiquitous occurrence of dehydrogenated benzophenanthridine-type alkaloids (ex. chelerythrine and sanguinarine) can be served as a chemical character of Chelidonieae. Furthermore, our results indicate that Chelidonieae can obviously be divided into two groups:the first group, including genera Sanguinaria, Eomecon, Macleaya and Bocconia, is characterized by the absence of TLC detected aporphine-, tetrahydroberberine- and reduced benzophenanthridi netype alkaloids, and their undulatedly or palmately incised leaves, as well as short capsules. The second group, comprising Stylophorum, Hylomecon, Dicranostigma and Chelidonium, yields predominately tetrahydroberberine- and reduced benzophenanthridinetype alkaloids, with usually deeply pinnatifid leaves, and long and slender capsules. As regards the medical importance and the resource utilization of Chelidonieae much attention should be paid to the following alkaloids and the taxa: chelidonine (Chelidonium majus ) , isocorydine ( Dicranostigma ) , tetrahydrocoptisine ( Stylophorum ) , chelerythrine (whole tribe particularly the genus Macleaya) and sanguinarine (whole tribe, particularly Macleaya).     

Calystegines in wild and cultivated Erythroxylum species

Calystegines were identified in the genus Erythroxylum for the first time. Erythroxylum novogranatense var. novogranatense, a species cultivated for cocaine production, contained 0.2% total calystegines in dry leaves. Forty six Erythroxylum herbarium species consisting mostly of leaf tissue were analysed for calystegines, and 38 were found positive. Calystegines were compared qualitatively and quantitatively between individual Erythroxylum species. Calystegines A(3) and B(2) were the major calystegines in most species. Total calystegine content reached up to 0.32% dry mass. The simultaneous occurrence of calystegines, cocaine, other alkaloids of a 3alpha-hydroxy- or 3beta-hydroxytropane structure together with nicotine supports the concept of common biosynthetic steps of these alkaloids in Erythroxylum. The present results are the basis for further investigations of the phylogenetic origin of tropane alkaloid biosynthesis in the taxonomically remote families Solanaceae and Erythroxylaceae.     

Occurrence and specialization of vessels in Xyridales

The occurrence and variation among vessels in available parts of 41 species in 16 genera of Rapateaceae and of 20 species in the four genera of Xyridaceae were determined. The vessels in Xyridaceae are more specialized in all organs of the plant than they are in Rapateaceae. Simple and scalariform perforation plates occur in the inflorescence axes and leaves of nearly all species of Xyridaceae but only scalariform plates occur in these organs of Rapateaceae – infrequently vessels are lacking in stems and leaves, at least in early metaxylem. Vessels in roots and stems of Mono–tremeae are most specialized (simple and scalariform plates) among tribes of Rapateaceae, with those in Rapateeae intermediate, and those in Schoenocephalieae and Saxofridericieae most primitive (only scalariform perforation plates). Brief comments are made about vessels as possible indicators of relationships with other families.     

Brassicaceae contain nortropane alkaloids

The report of cochlearine, the 3-hydroxybenzoate ester of tropine found in Cochlearia officinalis, Brassicaceae, initiated a screening for tropane alkaloids in Cochlearia species and for calystegines in further Brassicaceae. All ten Cochlearia species investigated contained cochlearine, tropine, and pseudotropine. Calystegines, nortropane alkaloids deriving from pseudotropine, were also identified in all Cochlearia species and accumulated up to 0.5% dry mass in leaves. Brassicaceae species of all major lineages of the family were analysed for calystegines. Of the 43 species included in the study, 18 accumulated calystegines of various structures. This is the first screening of Brassicaceae for products of the tropane alkaloid pathway, which is known as characteristic for plants of Solanaceae family. The identification of calystegines in all branches of the Brassicaceae family including Aethionema, a species at the basis of the family, suggests tropane alkaloids as secondary compound typical for Brassicaceae.     

Ipangulines and minalobines, chemotaxonomic markers of the infrageneric Ipomoea taxon subgenus Quamoclit, section Mina

A comprehensive GC-MS analysis of 8 Ipomoea species belonging to the subgenus Quamoclit, section Mina revealed that the members of this taxon form combinations of two necine bases with rare necic acids resulting in unique pyrrolizidine alkaloids. The occurrence and diversity of these metabolites show remarkable variations: Some species, especially Ipomoea hederifolia and Ipomoea lobata, are able to synthesize a large number of alkaloids whereas others, especially Ipomoea coccinea and Ipomoea quamoclit, are poor synthesizers with only a few compounds. However, these metabolites are apparently chemotaxonomic markers of this infrageneric taxon in general. They represent either esters of (-)-platynecine (altogether 48 ipangulines and 4 further esters including results of a previous study) or esters of (-)-trachelanthamidine, an additional novel structural type called minalobines (altogether 21 alkaloids). Both types are characterized by section-specific rare necic acids, e.g., ipangulinic/isoipangulinic acid, phenylacetic acid. The alkaloids of Ipomoea cholulensis, I. coccinea, I. hederifolia, Ipomoea neei, and Ipomoea quamoclit were mono and diesters of platynecine. Minalobines turned out to be metabolites of I. lobata (Cerv.) Thell. (syn.: Mina lobata Cerv.) lacking ipangulines. The major alkaloid of this species, minalobine R, has been isolated and identified as 9-O-(threo-2-hydroxy-2-methyl-3-phenylacetoxy-butyryl)-(-)-trachelanthamidine on the basis of spectral data. Apparently only two of the species included in this study, Ipomoea cristulata and Ipomoea sloteri, are able to synthesize both, ipangulines as well as minalobines. Minalobine O could be isolated as a major alkaloid of I. cristulata, its structure has been established as 9-O-(erythro-2-hydroxy-2-methyl-3-tigloyloxy-butyryl)-(-)-trachelanthamidine on the basis of spectral data.     

Midges of the subfamily Tanypodinae (Diptera,Chironomidae) of Russia: Tribes Coelotanypodini Kieffer, 1913 and Tanypodini Meigen, 1803

It is established that in the territory of Russia the subfamily Tanypodinae (Diptera, Chironomidae) includes 80 species belonging to 10 subgenera of 8 genera and 5 tribes; 4 species are recorded for the first time in the Palaearctic Region, and 16 species, in Russia. In the present study, larvae, pupae, and male adults from different areas of Russia, belonging to 9 species of 2 subgenera, 2 genera, and 2 tribes, are examined. Keys to larvae, pupae, and male adults of these species is provided.     

ANATOMY AS AN AID TO CLASSIFYING THE CYPERACEAE

During a period of about 10 years the systematic anatomy of the vegetative organs of more than 280 species belonging to 90 genera of the taxonomically complex family Cyperaceae have been examined, some of them for the first time. Abstracts of about 250 published articles relating to the anatomy of the Cyperaceae have also been prepared. The combined results of this investigation and literature survey are to appear as Vol. 5 of a reference book entitled Anatomy of the Monocotyledons. In the present article particulars are given of the anatomical characters which have proved to be among the most important as an aid in classifying the tribes and genera within the family. Special attention has been devoted to silica-bodies in surface-view preparations of the leaf epidermis. In transverse sections of the lamina, the relationship between genera and species in which there are dorsiventral, isobilateral, pseudodorsiventral, and cylindrical leaves, respectively, appears to be of special interest. Selected conclusions concerning the affinities between tribes and between certain genera and the tribes to which they belong within the Cyperaceae are presented. The relationship of the Cyperaceae to other families is briefly discussed.     

Physical mapping of rDNA genes in the ground beetle Carabus and related genera (Carabidae: Coleoptera)

The major ribosomal DNA (rDNA) loci were localized on meiotic and mitotic chromosomes and in interphase nuclei of 18 ground-beetle species belonging to three tribes of the supertribe Carabitae by fluorescence in situ hybridization (FISH), using a PCR-amplified 18S rDNA as a probe. Meiotic observations indicate that the 18S rDNA sequences are located on the largest autosomal bivalent in 12 species of Carabus , two species of Calosoma (both genera belonging to the tribe Carabini), and three sibling species of Ceroglossus chilensis (tribe Ceroglossini). The data suggest the occurrence of a conservative pattern in these three genera despite the chromosomal rearrangements that have led to karyotypes with higher chromosome numbers in Ceroglossus . A different result is found in Cychrus caraboides (tribe Cychrini), where ribosomal cistrons are located in two medium-sized autosomal pairs. Further species of Cychrini should be studied for corroborating the occurrence of molecular and karyotypical apomorphies in Cychrus with regard to the genera Carabus, Calosoma and Ceroglossus .     

A survey of alkaloids in the genera Harpalyce and Brongniartia (Fabaceae—Brongniartieae)

The presence of alkaloids in six species of Brongniartia and three species of Harpalyce is reported. This survey revealed remarkable qualitative differences in the alkaloid profiles of these two genera. B. discolor, B. lupinoides, B. sousae and B. intermedia showed a typical -pyridone pattern, with cytisine, anagyrine and baptifoline as major alkaloids. In leaves of the first three species ormosanine-type alkaloids occurred additionally. B. flava and B. vazquezii are devoid of -pyridones, but accumulate lupanine, hydroxylated lupanines and ester alkaloids. All three species of Harpalyce were similar in accumulating -pyridones, but H. formosa differed from H. brasiliana and H. pringlei in the presence of epilupinine. In general the alkaloid profiles of Brongniartia and Harpalyce show similarities to those of the Australian genera Hovea, Lamprolobium, Plagiocarpus and Templetonia and support therefore the actual concept of the enlarged tribe Brongniartieae.     

Hemlock alkaloids from Socrates to poison aloes

Hemlock (Conium maculatum L. Umbelliferae) has long been known as a poisonous plant. Toxicity is due to a group of piperidine alkaloids of which the representative members are coniine and gamma-coniceine. The latter is the more toxic and is the first formed biosynthetically. Its levels in relation to coniine vary widely according to environmental conditions and to provenance of the plants. Surprisingly, these piperidine alkaloids have turned up in quite unrelated species in the monocotyledons as well as the dicotyledons. Aloes, for instance, important medicinal plants, are not regarded as poisonous although some species are very bitter. Nevertheless a small number of mostly local species contain the alkaloids, especially gamma-coniceine and there have been records of human poisoning. The compounds are recognized by their characteristic mousy smell. Both acute and chronic symptoms have been described. The compounds are neurotoxins and death results from respiratory failure, recalling the effects of curare. Chronic non-lethal ingestion by pregnant livestock leads to foetal malformation. Both acute and chronic toxicity are seen with stock in damp meadows and have been recorded as problems especially in North America. The alkaloids derive biosynthetically from acetate units via the polyketide pathway in contrast to other piperidine alkaloids which derive from lysine.     

Evidence for general occurrence of homospermidine in plants and its supposed origin as by-product of deoxyhypusine synthase

Deoxyhypusine synthase (DHS) is involved in the post-translational activation of the eukaryotic initiation factor 5A (eIF5A) and, as a side-reaction, catalyzes the formation of homospermidine if its substrate, the eIF5A precursor protein, is replaced by putrescine. Plant homospermidine synthase is assumed to be phylogenetically derived from DHS; it represents a DHS having lost its intrinsic activity. The enzyme is expressed in plants producing pyrrolizidine alkaloids where it catalyzes the formation of homospermidine the unique precursor of pyrrolizidine alkaloids. Here we show that 29 species randomly selected from 18 angiosperm families as well as a few other terrestrial plant species, all were able to produce small amounts of homospermidine. Basing on these results and in the context of literature on the occurrence of homospermidine in the organismic kingdoms, a universal occurrence of homospermidine is assumed and ubiquitous DHS is suggested to be responsible for its formation. The synthesis of homospermidine as an enzymatic by-product of an essential enzyme is discussed in respect to the evolutionary origin of homospermidine synthase and the biosynthetic pathway of pyrrolizidine alkaloids.     

Contribution to the genome size knowledge of New World species from the Heliantheae alliance (Asteraceae)

This article contributes first genome size assessments by flow cytometry for 16 species, 12 genera, and 3 tribes from family Asteraceae, mostly belonging to the Heliantheae alliance, an assembly of 13 tribes from subfamily Asteroideae with a large majority of its species in the New World. Most genome sizes are accompanied by their own chromosome counts, confirming in most cases, although not all, previous counts for the species, and revealing possible cases of unknown dysploidy or polyploidy for certain taxa. The data contribute to the pool of knowledge on genome size and chromosome numbers in the family Asteraceae and will further allow deeper studies and a better understanding on the role of dysploidy in the evolution of the Heliantheae alliance. However, we still lack data for tribes Chaenactideae, Neurolaeneae, Polymnieae, and Feddeeae (the latter, monospecific) to complete the alliance representation.     

Pyrrolo- and pyridoazepine alkaloids as chemical markers in Stemona species

Broad-based phytochemical investigations on 31 Stemona species and geographical provenances led to an overview concerning characteristic accumulation trends and the distribution of different Stemona alkaloids. Two major metabolic differences suggested a taxonomic segregation of the complex Stemona tuberosa group from the other species, and was supported by morphological characters. Whereas most of the Stemona species were characterised by protostemonine type alkaloids, the S. tuberosa group clearly deviated by accumulation trends towards tuberostemonine or croomine derived alkaloids belonging to two different skeletal types. Also of chemotaxonomic relevance was the structural divergence of protostemonine type alkaloids into pyrrolo- or pyridoazepine derivatives represented by stemofoline or oxystemokerrine, respectively, as major constituents. Their common occurrence in different provenances of S. curtisii, also deviating from the other species by various chromosome numbers, deserves special taxonomic attention. Species specific chemical markers were given by the unique accumulation of didehydrostemofoline (=asparagamine A) in S. collinsae and stemokerrine in S. kerrii. In contrast to previous reports, no bisdehydro derivatives with an aromatic pyrrole ring were detected supporting the hypothesis that these alkaloids are artifacts. A new stereoisomer of tuberostemonine was isolated and identified by spectroscopic methods.     

用matK序列分析探讨木兰属植物的系统发育关系

用木兰科Magnoliaceae 57种植物的matK基因序列构建了该科的系统发育分支图。结果表明: (1)木兰属Magnolia L.是一个因为性状的趋同演化而建立的多系类群; (2)木兰亚属subgen. Magnolia和玉兰亚属subgen. Yulania (Spach) Reichenb.亲缘关系较远, 支持将后者从该属中分出建立玉兰属Yulania Spach, 木兰亚属作为木兰属保留; (3)木兰亚属的sect. Splendentes Dandy ex Vazquez组与皱种组sect. Rytidospermum Spach的两个美洲种M. macrophylla Michaux和M. dealbata Zucc.亲缘关系较近, 荷花玉兰组sect. Theorhodon Spach与常绿组sect. Gwillimia DC.的亲缘关系较近; (4)盖裂木属Talauma Juss.可以成立, 而其分布于亚洲的Blumiana Blume组可归入木兰属; (5)拟单性木兰属Parakmeria Hu &; Cheng、华盖木属Manglietiastrum Law以及单性木兰属Kmeria (Pierre) Dandy形成一个单系群, 与玉兰亚属和含笑属Michelia L.的亲缘关系较近。花的着生位置不足以作为木兰科的分族依据, 含笑族Michelieae和木兰族Magnolieae的特征及其界定应做修改。将玉兰亚属从木兰属分出后, 木兰属与含笑属无性状交叉,成为两个区别明显的属。     

Evolution of the inflated calyx syndrome in Solanaceae

Species that express the inflated calyx syndrome (ICS) are found in several genera of the Solanaceae. The MADS-box protein MPF2, together with the plant hormones cytokinin and gibberellin, has been shown to be responsible for this trait in Physalis floridana. We have used sequence data from 114 species belonging to 35 genera to construct a molecular phylogeny of Solanaceae. Apart from the 2 Witheringia species analyzed, species within a given genus cluster together on the resulting cladogram. Witheringia solanacea is embedded within the Physalinae, but Witheringia coccoloboides is placed basal to the Iochrominae. The ICS trait seems to be of multiple origins both within the Solanaceae and the Physaleae. Surprisingly, expression of MPF2-like genes in floral organs appears to be plesiomorphic in both the Physaleae and the Capsiceae. Some species in these tribes that show neither ICS nor calyx accrescence fail to express the MPF2-like gene in floral organs. Among those that do express this gene in the calyx are the species Capsicum baccatum, Lycianthes biflora, Tubocapsicum anomalum, W. solanacea, and Vassobia breviflora, all of which form small calyces that do not respond to externally applied hormones. The plesiomorphic nature of MPF2-like gene expression in the calyx of the Physaleae and Capsiceae raises the possibility that originally ICS also was actually a plesiomorphic character in these 2 groups. However, this trait might have undergone changes in a number of species due to secondary loss of components in ICS formation, like hormone response of calyx development. These findings are discussed in an evolutionary context of a molecular pathway leading to ICS.     

Morphology and ultrastructure of orbicules in the subfamily Ixoroideae (Rubiaceae)

Orbicules were studied in 43 species belonging to 32 genera of the five tribes of the Ixoroideae (Rubiaceae). The orbicules were investigated with scanning electron microscopy (SEM), light microscopy (LM), and transmission electron microscopy (TEM). Orbicules are present in all species investigated of the tribes Pavetteae, Octotropideae and Coffeeae. In the tribes Gardenieae and Aulacocalyceae orbicules were found in some species, while they were absent in others. 15 species out of 11 genera lack orbicules. Three orbicule types (III, V, and VI) could be distinguished, mainly on the basis of general morphological and ultrastructural variations. Orbicules that belong to type III (0.50-1.29μm) have perforations in their wall, a regular or irregular shape and two or three electron transparent cores. This orbicule type, exclusively found in all Pavetteae species investigated, can be divided into two subtypes. Orbicules of subtype IIIa are present in all genera related to Ixora, and orbicules of subtype IIIb in those genera related to Tarenna. Orbicules of type V (0.97-1.86μm) are present in Himalrandia tetrasperma (Aulacocalyceae), and in all Octotropideae genera investigated, except Feretia. Complexes of more than three individual orbicules characterize this type. They are irregularly shaped and have many perforations as well as sporopollenin granules on the orbicule wall. In all species investigated of tribe Coffeeae, type VI orbicules (0.56-1.60μm) are present. These orbicules are characterized by their embedded position towards the tapetal membrane, their aggregated form and by the presence of perforations as well as sporopollenin granules on their orbicule wall. In the tribe Gardenieae different types of orbicule were found (V, VI and orbicules that cannot be classified in our typology). Our results suggest that orbicule characters in the Ixoroideae may be systematically useful on tribal level.     

Flowering phenology of co-occurring Asteraceae: a matter of climate,ecological interactions,plant attributes or of evolutionary relationships among species?

We analyzed the flowering phenodynamics of 43 Asteraceae species co-occurring in natural populations of Chaco Serrano forests in central Argentina. We explored the potential influence of factors such as photoperiod and climate (variations in temperature, rainfall, and frost), animal-plant interactions (richness of floral visitors, frequency of visits), some plant attributes (plant growth form, seed dispersal mechanism), and evolutionary relationships among species on flowering phenodynamics. Cluster Analysis (CA) and Principal Component Analysis (PCA) were the multivariate statistical methods used to analyze emerging patterns associated with these co-occurring species. Null-model analyses were used to evaluate whether flowering times are aggregated, segregated, or random. Results showed that flowering phenology was significantly correlated with the seasonal variation in temperature, photoperiod, rainfall, and frost. The multivariate statistical methods separated all the species in three groups: 1) species with short flowering time, large plant floral display, high frequency of visits by a large number of species of floral visitors, anemochorous fruits, and shrubby growth form, with a tendency to a segregated flowering pattern; 2) species with long flowering time, small plant floral display, low frequency of visits by few insect species, anemochorous fruits, and herbaceous growth form; and 3) species with long flowering time, small plant floral display, intermediate values for frequency of visits and number of species of floral visitors, seed dispersal mechanisms other than anemochory, and herbaceous growth form. In addition, all but one species belonging to early-branching tribes (tribes phylogenetically close to the root of the Asteraceae tree) were grouped together and clustered in the same region of the two-dimensional PCA ordination. All species belonging to the late-branching tribes (Asteroideae subfamily tribes) included in group 1 were separated from the other Asteroideae species in the PCA. In conclusion, it seems that climatic factors restrict the phenological period of most species, and that plant attributes and taxonomic membership are strongly related to flowering phenodynamics in this group of Asteraceae studied.     

Suitability of cuticular pores and sensilla for harpacticoid copepod species delineation and phylogenetic reconstruction

Cuticular organs have not been described systematically in harpacticoids until recently, and they have never been used as characters for reconstructing phylogenetic relationships in any crustacean group. We survey cuticular pores and sensilla on somites in ten Miraciidae species, belonging to six genera, from Korea, Australia, and Russia. Nine species belong to the subfamily Stenheliinae, while the outgroup belongs to the subfamily Diosaccinae. We aim to compare phylogenetic trees reconstructed for these harpactioids based on: 1) cuticular organs (with 76 characters scored, 71% of them phylogenetically informative); 2) traditionally used macro-morphological characters (66 scored, 77% of them informative); and 3) mtCOI DNA data. All analyses suggest that cuticular organs are useful characters for harpacticoid species delineation, although not as sensitive as some fast-evolving molecular markers. Reconstructed cladograms based on all three datasets show very high bootstrap values for clades representing distinct genera, suggesting that cuticular organs are suitable characters for studying phylogenetic relationships. Bootstrap values for the more basal nodes differ among the different cladograms, as do the sister-group relationships they suggest, indicating that cuticular organs probably have different evolutionary constraints from macro-morphological characters. Cuticular organs could be quite useful in the study of old museum specimens and fossil crustaceans.     

Actinomycetous root nodules in angiosperms of Pakistan

Summary In a survey, out of the nineteen genera of non-leguminous angiosperms that are already reported to bear actinomycete-induced nitrogen-fixing root nodules from various parts of the world, the species of seven genera (Alnus, Elaeagnus, Hippophaë, Coriaria, Datisca, Rubus and Casuarina) have been located in Pakistan and checked for nodulation. All the investigated species of the these genera, except those of Rubus and some of the introduced species of Casuarina, were found to bear nodules. In all 12 species belonging to six genera of five families have been recorded to bear actinorhizal nodules in Pakistan.