Chemosystematic implications of flavonoids in Aniba riparia

The trunk wood of Aniba riparia (Nees) Mez (Lauraceae) contains flavokawin-B, (2S)-pinostrombin, (2S)-5, 7-di-O-methylpinocembrin, (2R, 3R)-5, 7-di-O-methylpinobanksin, izalpinin and 3,5, 7-tri-O-methylgalangin. Structural comparison of these flavonoids with the pyrones and neolignans, which characterized all previously examined Aniba spp., leads to a chemical classification of the genus.     

Neolignans from the seeds of Prunus tomentosa (Rosaceae) and their chemotaxonomic interest

The role of neolignans in the chemotaxonomy of the genus Prunus has long been neglected. In this study, two new dihydrobenzofuran neolignans tomentosanans A (12) and B (14), together with 15 known neolignans, were isolated from the seeds of Prunus tomentosa. This is the first report on the occurrence of compounds 1–12, 14, 15 and 17 in the genus Prunus. The biosynthetic pathways of these neolignans are also summarized. Together, these neolignans represent a phytochemical fingerprint for P. tomentosa, which may be used for identification of Prunus species.     

Chemosystematic implications of benzyltetrahydroisoquinolines in Aniba

The presence of simple benzyltetrahydroisoquinolines in Aniba species, known for their varied phenylpropanoid chemistry, is reported. Since other genera in the Lauraceae contain, in contrast, quite elaborate alkaloidal types, a regulating mechanism may exist by which phenylalanine is channelled either into phenylpropanoids or into benzylisoquinolines. This mechanism is evoked in order to rationalize chemical evolution in the Magnoliidae.     

Eusiderins and other neolignans from an Aniba species

A previous report disclosed the presence of benzodioxan and bicyclo[3.2.1]octanoid neolignans in the benzene extract of the trunk wood of an Amazonian Aniba (Lauraceae) species. The chloroform extract of the same material contains additionally two new benzodioxan neolignans [rel-(7S,8R)-Δ^8′-7-hydroxy-3,4,5,5′-tetramethoxy-7.0.3′,8.0.4′-neolignan; rel-(7R,8R)-Δ^7′-3,4,5,5′-tetramethoxy-9′-oxo-7.0.3′,8.0.4′-neolignan], two new bicyclo[3.2.1]-octanoid neolignans [(7R,8S,1′S,2′S,3′S,4′R)-Δ^8′-2′,4′-dihydroxy-3,3′-dimethoxy-4,5-methylenedioxy-1′,2′,3′,4′,5′,6′-hexahydro-5′-oxo-7.3′,8.1′-neolignan; (7R,8S,1′R,2′S,3′S)-Δ^8′-2′-hydroxy-3,3′,5′-trimethoxy-4,5-methylenedioxy-1′,2′,3′,4′-tetrahydro-4′-oxo-7.3′,8.1′-neolignan] and a hydrobenzofuranoid neolignan [(7S,8R,1′S,5′S)-Δ^8′-3,3′,5′-tri-methoxy-4,5-methylenedioxy-1′,4′,5′,6′-tetrahydro-4′-oxo-7.0.2′,8.1-neolignan].     

Chemogeography ofAniba (Lauraceae)

A comparison between geographical distribution and secondary metabolites of 18 species ofAniba (Lauraceae) leads to a coherent picture of spatial and chemical evolution of these species. In chemical evolution, general mechanisms as blocking of reaction steps leading to primary metabolites and diversification of secondary metabolites within biogenetic groups are found to be operative. Sympatric distribution of closely related species seems to imply chemical diversity. The relation between size of distribution area and evolutionary status of individual species showsAniba to be an evolutionarily more recent, actively evolving genus.Part XIV in the series Plant Chemosystematics and Phylogeny. For Part XIII seeGottsberger & Gottlieb 1981).     

The sesquiterpenoids and their chemotaxonomic implications in Senecio L. (Asteraceae)

Sesquiterpenoids are important characteristic compounds in Asteraceae plants. These compounds have been proposed to be potential chemotaxonomic markers, but this application has not been comprehensively investigated. In this paper, sesquiterpenoids from 149 species of the genus Senecio were investigated to assess their taxonomic utility. The presence and absence were encoded as binary taxonomic characteristics and subsequently utilised in a clustering analysis. The previously biosynthesis pathway of sesquiterpenoids was taken into account to explore the relationship among these species contained different sesquiterpenoid types. In addition, the DNA phylogeny was also considered to explore the distribution and evolution of sesquiterpenoids in genus Senecio further. As a result, seven chemical major sections within the Senecio were recognised based on the chemical character. Although with several exceptions, the biosynthesis pathway, molecular phylogeny and the geographical origin of these sesquiterpenoid were found to be related to the chemical sections, which largely confirmed the validity of our chemo-classification for genus Senecio. In conclusion, we suggest that the sesquiterpenoid character in Senecio has some value for the genus taxonomy but should be analysed carefully and critically.     

Hexahydrobenzofuranoid neolignans from an Aniba species

The trunk wood of an Amazonian Aniba species contains three novel neolignans: (2R, 3R, 3aS, 5R)-3a-allyl-5-methoxy-2-(3,4,5-trimethoxyphenyl)-3-methyl-2,3,3a,4,5,6-hexahydro-6-oxobenzofuran (canellin-D), (2R,3R,3aS,5R)-3a-allyl-5,7-dimethoxy-2-(3-methoxy-4,5-methylenedioxyphenyl)-3-methyl-2,3,3a,4,5,6-hexahydro-6-oxobenzofuran (canellin-E) and (2S,3S,3aS,5R)-3a-allyl-5-methoxy-2-(3-methoxy-4,5-methylenedioxyphenyl)-3-methyl-2,3,3a,4,5,6-hexahydro-6-oxobenzofuran (armenin-C). The absolute stereochemistries of these and of all other known hexahydro-6-oxobenzofurans were determined by CD comparisons with model compounds.     

Three New Species of Deltoblastus Fay from the Permian of Timor

Deltoblastus is a genus of Permian blastoid comprised of 15 species, each differing based on subtle thecal morphology differences. Three new species are introduced here, based on characteristics present which distinguish individuals from established morphotypes. In order to guarantee a more complete understanding of the genus, a complex character matrix containing all 15 named and three new species was created, defining all species based on the presence or absence of 30 unique traits. Differences in character compositions give evidence for unique thecal morphologies, supporting the three new species which are proposed.     

A chemotaxonomic survey of the tribe psoraleeae in africa

A study of the leaf flavonoids, furanocoumarins and essential oils of 51 species (three genera) of the tribe Psoraleeae (Fabaceae) has provided chemical data to support the recent subdivision of the large worldwide genus Psoralea into a number of segregate genera. The flavonoid patterns in most species were very similar, consisting largely of proanthocyanidins and complex mixtures of flavone O- and C-glucosides. Psoralea repens, the only maritime species to be examined, is unique in containing only rutin. Three isoflavones (daidzein, formononetin and genistein) were of widespread occurrence. The genera Psoralea and Otholobium, which could not be separated on flavonoid data, were clearly demarcated by their essential oils. Furanocoumarin patterns were useful for the characterization of species.     

Neolignans from an Aniba species

The trunk wood of an Amazonian Aniba (Lauraceae) species contains, besides dillapiol and the benzodioxane-type neolignan eusiderin, four bicyclo(3.2.1)octanoid neolignans. These comprise representatives of the canellin-type: the known methoxycanellin-A and the novel compounds characterized as (1R, 3S, 4S, 5S, 6S, 7R)-1-allyl-4-hydroxy-3, 5-dimethoxy-7-methyl-6-(3′-methoxy-4′, 5′-methylenedioxyphenyl)-8-oxo-bicyclo(3.2.1)octane; (1R, 3S, 4S, 5S, 6S, 7R)-1-allyl-4-hydroxy-3, 5-dimethoxy-7-methyl-6-(3′, 4′, 5′-trimethoxyphenyl)-8-oxobicyclo(3.2.1)octane and (1R, 4R, 5R, 6S, 7R, 8S)-1-allyl-4, 8-dihydroxy-5-methoxy-7-methyl-6-(3′-methoxy-4′,5′-methylenedioxyphenyl)-3-oxobicyclo(3.2.1)octane.     

El género Ochrolechia A. Massai. (Pertusariaceae,liquenes) en Espana y Portugal

The genus Ochrolechia is widespread in Spain and Portugal and now includes 14 species, 1 form and 4 chemical races (11 species and 3 chemical races are epiphytes, 2 species, 1 form and 1 chemical race are saxicolous and one species is muscicolous). We propose a new combination: O. dalmatica (Erichsen) Boqueras. Eight species are excluded from the Spanish and Portuguese floras: O. aggregata (Bagl.) Verseghy, O. anomala Verseghy, O. glaucescens (Hue) Zahlbr., O.frigida (Sw.) Lynge, O. pseudotartarea (Vain.) Verseghy, O. rosella Müll. Arg., O. subpallescens Verseghy, O. tenuissima Verseghy, O. crozalsiana Clauzade et Vêzda is included in O. tartarea. The criteria for the identification of these species are: 1 ) the chemical substances (the presence/absence of gyrophoric acid in the thallus and/or in the apothecia determines the groups inside of the genus, the presence of alectoronic acid determines the chemical races); 2) thallus with or without soredia or isidia; 3) the presence of pruina on the disc; and 4) the substratum. A key for the identification to all mentioned species is included.     

Flavonoid patterns in the farina of goldenback and silverback ferns

Most species of the fern genus Pityrogramma show a farinose indument caused by a deposit of exuded flavonoid aglycones. Some 220 samples, comprising 14 species, have been studied for the chemical composition of their farinas. Flavones, flavonols and C-methylated flavonoid are rarely found. The presence of certain chalcones and dihydrochalcones, however, appears to be to some extent characteristic for the genus. In some cases the farina flavonoid pattern is species-specific; in one species also variety-specific patterns and even chemotypes are observed. In general, the flavonoid chemistry in Pityrogramma parallels frond morphology to a great extent. This supports the concept that around a core of generalized species a few variant species exist which are best treated as belonging to Pityrogramma.     

The oldest South American tuco-tuco (late Pliocene,northwestern Argentina) and the boundaries of the genus Ctenomys (Rodentia,Ctenomyidae)

A new species of Ctenomyidae from the late Pliocene of Uquía Formation (northwestern Argentina) is described. The new remains consist of a fragmentary rostrum, and a left mandible with partial lower dentition. Its phylogenetic affinity and morphological specializations for tooth-digging support its assignation to the South American rodent genus Ctenomys. In this context, we highlight the importance of unique morphological specializations for the delimitation of genera within an intrafamilial clade in which similar adaptive strategies could have evolved more than once. The new materials are the oldest fossils for the genus (ca. 3.5 Ma), and their finding in the central Andes agrees with previous hypotheses about the possible area of origin of Ctenomys. They precede by about one million years the presence of Ctenomys chapalmalensis in the Pliocene of the Pampean region of central Argentina, the oldest record previously known for the genus. Nevertheless, the new species does not contribute key information about ancestral character states for the genus beyond those already known through C. chapalmalensis. The phylogenetic, adaptive and even chronological information supplied by these new materials would be linked to the differentiation of the genus rather than to its origin.     

Benzofurans and methylated flavonoids of Geraea (Asteraceae)

Phytochemical analysis revealed the presence of several rare benzofurans and C-8 oxygenated flavonoids in Geraea canescens. Geraea viscida, the only other species in the genus, lacked benzofurans and yielded simple flavonols without extra oxygenation. The flavonoids of both species were found to be deposited on the leaf surface. The chemical data suggest a close affinity between Geraea canescens and the genus Enceliopsis and less closely with the genus Encelia. The systematic affinity of Geraea canescens to Geraea viscida, however, seems unclear judged from the divergent chemical data obtained.     

Lancea tibetica as the Tibetan herb: A review of its phytochemistry and pharmacology

This review, based on nearly 25 literary sources, discusses the chemical nature and biological effects of the whole plant of Lancea tibetica Hook. f. et Thoms (Scrophulariaceae). Several types of chemical constituents have been isolated from Lancea tibetica (LT) including 34 phenolpropanoids (16 lignans, 5 neolignans, 5 nonanones, 4 phenylpropanoid glycosides, and 4 propanediols), 9 flavones, 6 triterpenoids, and 11 amino acids. Various extracts and individual compounds derived from this species have been determined to possess a variety of pharmacological effects, such as anti-tumour and antioxidant functions. The results of data analysis on the chemical and pharmacological characteristics of LT support the view that this plant has many therapeutic properties, suggesting its potential as an effective herbal remedy. Finally, suggestions for further avenues of research on the chemical and pharmacological properties of LT and ways in which to further exploit LT are presented in this review.     

Paleobiochemistry of North American fossil Liriodendron sp.

Organic geochemical analyses are presented for a fossil Liriodendron sp. from the Miocene, Clarkia Flora of Northern Idaho. Flavonoid profiles determined for the fossil and two extent species of Liriodendron (L. chinense and L. tulipifera) confirm the generic status of the fossil material, but owing to a generic uniformity in flavonoid composition, fail to resolve taxonomic affinities at the species level. Steroid and other cycloalkane-alkene profiles indicate that the fossil taxon has a greater chemical similarity with L. chinense than L. tulipifera, despite the general leaf outline similarity between the fossil species and extent L. tulipifera. The morphologic and chemical data are interpreted as evidence for mosaic evolution within the genus, and the non-canalization of character states in some Miocene species.     

Phylogenetic Relationships of American Willows (Salix L., Salicaceae)

Salix L. is the largest genus in the family Salicaceae (450 species). Several classifications have been published, but taxonomic subdivision has been under continuous revision. Our goal is to establish the phylogenetic structure of the genus using molecular data on all American willows, using three DNA markers. This complete phylogeny of American willows allows us to propose a biogeographic framework for the evolution of the genus. Material was obtained for the 122 native and introduced willow species of America. Sequences were obtained from the ITS (ribosomal nuclear DNA) and two plastid regions, matK and rbcL. Phylogenetic analyses (parsimony, maximum likelihood, Bayesian inference) were performed on the data. Geographic distribution was mapped onto the tree. The species tree provides strong support for a division of the genus into two subgenera, Salix and Vetrix. Subgenus Salix comprises temperate species from the Americas and Asia, and their disjunction may result from Tertiary events. Subgenus Vetrix is composed of boreo-arctic species of the Northern Hemisphere and their radiation may coincide with the Quaternary glaciations. Sixteen species have ambiguous positions; genetic diversity is lower in subg. Vetrix. A molecular phylogeny of all species of American willows has been inferred. It needs to be tested and further resolved using other molecular data. Nonetheless, the genus clearly has two clades that have distinct biogeographic patterns.     

Flavonoids with chemotaxonomic significance from Cajanus scarabaeoides

Phytochemical investigation of Cajanus scarabaeoides (L.) Thouars (Fabaceae) led to the isolation of six compounds. The chemical structures of all compounds were determined by spectroscopic methods. All isolates were reported from this species for the first time. The presence of these compounds is consistent with the chemical classes reported from other members of the genus Cajanus. In summary, this study reported six compounds isolated from Cajanus scarabaeoides and discussed the plant chemotaxonomy of Cajanus genus.     

The Rhizosphere Selects for Particular Groups of Acidobacteria and Verrucomicrobia

There is a lack in our current understanding on the putative interactions of species of the phyla of Acidobacteria and Verrucomicrobia with plants. Moreover, progress in this area is seriously hampered by the recalcitrance of members of these phyla to grow as pure cultures. The purpose of this study was to investigate whether particular members of Acidobacteria and Verrucomicrobia are avid colonizers of the rhizosphere. Based on previous work, rhizosphere competence was demonstrated for the Verrucomicrobia subdivision 1 groups of Luteolibacter and Candidatus genus Rhizospheria and it was hypothesized that the rhizosphere is a common habitat for Acidobacteria subdivision 8 (class Holophagae). We assessed the population densities of Bacteria, Verrucomicrobia subdivision 1 groups Luteolibacter and Candidatus genus Rhizospheria and Acidobacteria subdivisions 1, 3, 4, 6 and Holophagae in bulk soil and in the rhizospheres of grass, potato and leek in the same field at different points in time using real-time quantitative PCR. Primers of all seven verrucomicrobial, acidobacterial and holophagal PCR systems were based on 16S rRNA gene sequences of cultivable representatives of the different groups. Luteolibacter, Candidatus genus Rhizospheria, subdivision 6 acidobacteria and Holophaga showed preferences for one or more rhizospheres. In particular, the Holophaga 16S rRNA gene number were more abundant in the leek rhizosphere than in bulk soil and the rhizospheres of grass and potato. Attraction to, and colonization of, leek roots by Holophagae strain CHC25 was further shown in an experimental microcosm set-up. In the light of this remarkable capacity, we propose to coin strain CHC25 Candidatus Porrumbacterium oxyphilus (class Holophagae, Phylum Acidobacteria), the first cultured representative with rhizosphere competence.     

Pan-genomics of Ochrobactrum species from clinical and environmental origins reveals distinct populations and possible links

Ochrobactrum genus is comprised of soil-dwelling Gram-negative bacteria mainly reported for bioremediation of toxic compounds. Since last few years, mainly two species of this genus, O. intermedium and O. anthropi were documented for causing infections mostly in the immunocompromised patients. Despite such ubiquitous presence, study of adaptation in various niches is still lacking. Thus, to gain insights into the niche adaptation strategies, pan-genome analysis was carried out by comparing 67 genome sequences belonging to Ochrobactrum species. Pan-genome analysis revealed it is an open pan-genome indicative of the continuously evolving nature of the genus. The presence/absence of gene clusters also illustrated the unique presence of antibiotic efflux transporter genes and type IV secretion system genes in the clinical strains while the genes of solvent resistance and exporter pumps in the environmental strains. A phylogenomic investigation based on 75 core genes depicted better and robust phylogenetic resolution and topology than the 16S rRNA gene. To support the pan-genome analysis, individual genomes were also investigated for the mobile genetic elements (MGE), antibiotic resistance genes (ARG), metal resistance genes (MRG) and virulence factors (VF). The analysis revealed the presence of MGE, ARG, and MRG in all the strains which play an important role in the species evolution which is in agreement with the pan-genome analysis. The average nucleotide identity (ANI) based on the genetic relatedness between the Ochrobactrum species indicated a distinction between individual species. Interestingly, the ANI tool was able to classify the Ochrobactrum genomes to the species level which were assigned till the genus level on the NCBI database.