Diterpenes related to grindelic acid and further constituents from Grindelia species

The aerial parts of Grindelia stricta afforded in addition to known compounds 21 diterpenes, all closely related to grindelic acid. The aerial part     

Non-polar and polar chemical profiling of six Casearia species (Salicaceae)

Six species of Casearia (C. decandra, C. grandiflora, C. javitensis, C. arborea, C. lasiophylla and C. ulmifolia) were chemically investigated in their non-polar and polar constituents. To this purpose, leaf extracts were analyzed by Gas- (GC) and Liquid-Chromatography (LC) coupled with Mass Spectrometry (MS). Twenty compounds, mainly identified as terpenes, fatty acids and hydrocarbons, and differentially expressed in the six species, were detected in the non-polar extracts. Fourteen compounds, among which glycosylated flavonoids and clerodane-type diterpenes, were tentatively identified by LC-MS/MS analysis in the leaf ethanol extracts.     

Ellagitannins of the casuarinaceae,stachyuraceae and myrtaceae

Eight ellagitannins and related polyphenols, found in Casuarina stricta and Stachyurus praecox, were detected in the leaf of Psidium species. Five of them and a new polyphenol, named isostrictinin, were isolated from Psidium guajava. Most of these compounds were detected in several species of Myrtaceae, and 2, 3-hexahydroxydiphenoylglucose and 4, 6-hexahydroxydiphenoylglucose were found in some.     

Flavonoid dimers from the aerial parts of Conyza stricta

A new flavonoid dimer, strictatin (10), was identified from the aerial part of Conyza stricta, in addition to eleven known compounds. The structure of compound 10 was determined by spectral analyses, including 1D, 2D NMR and HR-ESI-MS experiments. All compounds were identified from Conyza stricta for the first time and flavonoid dimers were firstly reported from the family Asteraceae. The chemotaxonomic significance of the identified metabolites was discussed.     

Coniochaeta polymorpha, a new species from endotracheal aspirate of a preterm neonate, and transfer of Lecythophora species to Coniochaeta

A new species of Coniochaeta from endotracheal secretion of a preterm neonate, Coniochaeta polymorpha, is described. This anamorphic species is characterized by development of dark brown colonies after 1 week of incubation on culture medium, formation of abundant yeast-like cells and sclerotium-like structures producing discrete, brown, nearly globose phialidic conidiogenous cells and absence of chlamydospores. A combined sequence dataset of the ITS region, partial LSU rDNA, actin and β-tubulin genes sufficiently resolved the unique phylogenetic status of this species. In response to recent changes in the nomenclature for pleomorphic fungi, we transfer the Lecythophora species to Coniochaeta, and propose the following new combinations: Coniochaeta canina, Coniochaeta cateniformis, Coniochaeta decumbens, Coniochaeta fasciculata, Coniochaeta hoffmannii, Coniochaeta lignicola, Coniochaeta luteorubra, Coniochaeta luteoviridis and Coniochaeta mutabilis.     

Direct demonstration of duvatrienediol biosynthesis in glandular heads of tobacco trichomes

Biosynthesis of the diterpenes, α and β 4,8,13-duvatriene-1,3-diol, has been observed in detached, intact glandular heads from trichomes of Nicotiana tabacum, Tobacco Introduction 1068. This result shows directly that the glandular head portion of the trichome is capable of duvatrienediol biosynthesis. In additional experiments, all of the [¹⁴C] duvatrienediol formed from sodium [2-¹⁴C]acetate by leaf midrib sections was recovered with trichome exudate and surface washes. None was found in trichome stalk, epidermal or subepidermal tissue extracts. Also, removal of glandular heads and exudate from midrib sections reduced or eliminated duvatrienediol biosynthetic capacity. Together these results strongly suggest that glandular heads are the primary, and perhaps the only, site of duvatrienediol biosynthesis in this plant.

Incubation of detached, intact glandular heads with sodium [¹⁴C]acetate in the dark or incubation in the light in the presence of DCMU reduced incorporation into duvatrienediols by 97%. These results suggest that chloroplasts which are abundant in glandular heads are involved in the biogenesis of these compounds.

     

Temperature requirements for dormancy break and seed germination vary greatly among 14 wetland Carex species

We evaluated dormancy loss in seeds of 14 Carex species (C. atherodes, C. brevior, C. comosa, C. cristatella, C. cryptolepis, C. granularis, C. hystericina, C. lacustris, C. pellita, C. scoparia, C. stipata, C. stricta, C. utriculata, C. vulpinoidea) under growing season and stratification conditions and determined the temperature requirements for germination. Seeds were germinated for 1 year at a diel temperature regime (5/1 °C, 14/1 °C, 22/8 °C, or 27/15 °C) or a seasonal regime (seeds moved among the four diel regimes to mimic seasonal temperatures). All species had conditionally dormant seeds at maturity. The optimal temperature for germination of most species was 27/15 °C. The 14 species were grouped by their seed viability, dormancy, and germination with a Seed Regeneration Index (SRI; range 0–1) using the results of this study and a previously published paper on stratification effects on Carex seed dormancy and germination. The eight species that had an SRI value >0.5 (C. brevior, C. comosa, C. cristatella, C. cryptolepis, C. hystericina, C. scoparia, C. stipata, C. vulpinoidea) had high seed viability (>60%) and required little to no stratification to germinate readily over a broad range of temperatures. The six species with an SRI value <0.5 (C. atherodes, C. granularis, C. lacustris, C. pellita, C. stricta, C. utriculata) generally had low seed viability (<50% and often <1%) and required stratification or particular temperatures (35/30 °C or 5/1 °C for C. stricta; 35/30 °C for C. utriculata; 27/15 °C for C. atherodes, C. lacustris, C. pellita; 5/1 °C for C. granularis) for germination ≥50%. These six species will require more attention from restoration practitioners to ensure that there are sufficient viable seeds to meet revegetation goals, that dormancy break is achieved, and that seeds are sown when temperatures are optimal for germination. The different seed germination syndromes that we found for these Carex species likely contribute to variable seed bank formation and emergence patterns, and species coexistence.     

Differential metabolism of diastereoisomeric diterpenes by Preussia minima,found as endophytic fungus in Cupressus lusitanica

The plant diastereoisomeric diterpenes ent-pimara-8(14)-15-dien-19-oic acid, obtained from Viguiera arenaria, and isopimara-8(14)-15-dien-18-oic acid, isolated from Cupressus lusitanica, were distinctly functionalized by the enzymes produced in whole cell cultures of the fungus Preussia minima, isolated from surface sterilized stems of C. lusitanica. The ent-pimaradienoic acid was transformed into the known 7β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid, and into the novel diterpenes 7-oxo-8 β-hydroxy-ent-pimara-8(14)-15-dien-19-oic and 7-oxo-9β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acids. Isopimara-8(14)-15-dien-18-oic acid was converted into novel diterpenes 11α-hydroxyisopimara-8(14)-15-dien-18-oic acid, 7β,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, and 1β,11α-dihydroxyisopimara-8(14)-15-dien-18-oic acid, along with the known 7β-hydroxyisopimara-8(14)-15-dien-18-oic acid. All compounds were isolated and fully characterized by 1D and 2D NMR, especially ¹³C NMR. The diterpene bioproduct 7-oxo-9β-hydroxy-ent-pimara-8(14)-15-dien-19-oic acid is an isomer of sphaeropsidin C, a phytotoxin that affects cypress trees produced by Shaeropsis sapinea, one of the main phytopathogen of Cupressus. The differential metabolism of the diterpene isomers used as substrates for biotransformation was interpreted with the help of computational molecular docking calculations, considering as target enzymes those of cytochrome P450 group.     

Phytochemistry and bioactivity of aromatic and medicinal plants from the genus Agastache (Lamiaceae)

Agastache is a small genus of Lamiaceae, comprising 22 species of perennial aromatic medicinal herbs. In this article, we review recent advances in phytochemical, pharmacological, biotechnological and molecular research on Agastache. The phytochemical profile of all Agastache species studied to date is generally similar, consisted of two main metabolic classes—phenylpropanoids and terpenoids. In the relatively variable essential oils, most populations of different Agastache species contain over 50 % of a phenylallyl compound—estragole. Also, other volatile compounds (methyleugenol, pulegone, menthone, isomenthone and spathulenol) were reported in various proportions. Major non-volatile metabolites belong to phenolic compounds, such as caffeic acid derivatives, especially rosmarinic acid as well as several flavones and flavone glycosides like acacetin, tilianin, agastachoside, and a rare dimeric malonyl flavone (agastachin). Two unique lignans—agastenol and agastinol—were also isolated. Terpenoids include triterpenoids of oleanane-type (maslinic acid, oleanolic acid and β-amyrin), ursane-type (ursolic acid, corosolic acid and α-amyrin), and typical plant sterols, as well as abietane-type oxidized diterpenes (e.g., agastaquinone, agastol, and others). The bioactivity of various extracts or individual compounds in vitro and in vivo include antimicrobial, antiviral and anti-mutagenic activity, cytotoxic activity to cancer cell lines, and anti-nociceptive, anti-inflammatory, anti-atherogenic, antioxidant as well as biocidal activity to several foodstuff pests. Biotechnological and molecular studies have focused on in vitro propagation and enhancing the biosynthesis of bioactive metabolites in cell or organ cultures, as well as on the expression of genes involved in phenolic biosynthesis.     

Phytochemical and taxonomic evaluation of Rhazya stricta in Saudi Arabia

Rhazya stricta Decne is an important medicinal species used in indigenous medicinal herbal drugs to cure various diseases in South Asia (Pakistan, India and Afghanistan) and in the Middle East (e.g. Saudi Arabia, Qatar, United Arab Emirates (UAE), Iran and Iraq). Some of its alkaloids have been reported to have anticancerous properties. The aim of our study is to examine the morphological and taxonomical parameters for R. stricta in the Saudi Arabia; concentrations and distributions of some secondary metabolites; and also to determine the antioxidant and free radical scavenging activity. The results of present study showed that there was no influence of environment on the structure of stomata and trichomes as studying species with R. stricta. In conclusion our study shows no trichomes on leaf of R. stricta it is glabrous, whereas, variations between many secondary metabolites such as flavonoids and phenolic compounds occurred in response to changing climatic conditions.     

Structural diversity and geographical distribution of halogenated secondary metabolites in red algae,Laurencia nangii Masuda (Rhodomelaceae,Ceramiales), in the coastal waters of North Borneo Island

The red algae genus Laurencia (Rhodomelaceae, Ceramiales) is known as a prolific producer of halogenated secondary metabolites with a high level of species diversity and geographical distribution. In North Borneo Island, Malaysia, there are four main Laurencia species: Laurencia snackeyi, Laurencia majuscula, Laurencia similis and L. nangii. Although the chemistry of Laurencia is well studied, the diversity of compounds in L. nangii has not been thoroughly investigated. Therefore, we studied the chemical constituents of seven populations of L. nangii from Tunku Abdul Rahman Marine Park (two populations), Dinawan Island (one population), Tun Mustapha Marine Park (two populations) and Tun Sakaran Marine Park (two populations). Halogenated compounds were isolated and the structures determined via spectroscopic methods. A total of 20 metabolites belonging to the classes of sesquiterpenes, acetylenes, bromoallenes, diterpenes and triterpenes were identified. Populations from Tunku Abdul Rahman Marine Park and Dinawan Island contained non-chamigrane-type sesquiterpenes, acetylenes and diterpenes. Populations from Tun Mustapha Marine Park contained chamigrane-type sesquiterpenes, acetylenes and diterpenes. However, the chemical compositions of populations from Tun Sakaran Marine Park were found to differ significantly, containing chamigrane-type and non-chamigrane-type sesquiterpenes, bromoallenes and triterpenes. This investigation has revealed the presence of interesting chemotaxonomical markers in populations of L. nangii and the existence of chemical races in this species.     

Labdane diterpenes from Marrubium thessalum

From the aerial parts of Marrubium thessalum, four labdane diterpenes, 13S-preperegrinine, 3α-hydroxymarrubiin, 9α,13R-15,16-bisepoxy-15β-methoxy-3-oxo-labdan-6β,19-olide and 15-methoxyvelutine C, have been isolated together with four known diterpenes and one methoxylated flavone, ladanein. The structures of the isolated compounds were established by means of NMR (COSY, HSQC, HMBC, NOESY, and ROESY) and MS spectral analyses. Complete NMR assignments are reported for 13R-preperegrinine. Characteristic compounds of the plant were peregrinine and ladanein.     

Phytotoxic Allelochemicals From Roots and Root Exudates of Leafy Spurge (Euphorbia esula L.)

Invasive plants are a widespread problem but the mechanisms used by these plants to become invasive are often unknown. The production of phytotoxic natural products by invasive weeds is one mechanism by which these species may become successful competitors. Here we conducted a bioactivity-driven fractionation of root extracts and exudates from the invasive plant leafy spurge (Euphorbia esula L.), and structurally characterized jatrophane diterpenes and ellagic acid derivatives. Ellagic acid derivatives and one of the jatrophane diterpenes, esulone A, have been previously reported from leafy spurge, but another of the jatrophane diterpenes, kasuinine B, has not. We show that these compounds are phytotoxic but affect plants in different ways, either inducing overall plant necrosis or reducing root branching and elongation.Key Words: phytotoxicity, allelochemicals, roots, root exudates, jatrophane diterpenes, kansuinine B, ellagic acid derivatives, leafy spurge, Euphorbia esula, Arabidopsis thaliana     

Multilocus Patterns of Nucleotide Diversity, Population Structure and Linkage Disequilibrium in Boechera stricta, a Wild Relative of Arabidopsis

Information about polymorphism, population structure, and linkage disequilibrium (LD) is crucial for association studies of complex trait variation. However, most genomewide studies have focused on model systems, with very few analyses of undisturbed natural populations. Here, we sequenced 86 mapped nuclear loci for a sample of 46 genotypes of Boechera stricta and two individuals of B. holboellii, both wild relatives of Arabidopsis. Isolation by distance was significant across the species range of B. stricta, and three geographic groups were identified by structure analysis, principal coordinates analysis, and distance-based phylogeny analyses. The allele frequency spectrum indicated a genomewide deviation from an equilibrium neutral model, with silent nucleotide diversity averaging 0.004. LD decayed rapidly, declining to background levels in ~10 kb or less. For tightly linked SNPs separated by <1 kb, LD was dependent on the reference population. LD was lower in the specieswide sample than within populations, suggesting that low levels of LD found in inbreeding species such as B. stricta, Arabidopsis thaliana, and barley may result from broad geographic sampling that spans heterogeneous genetic groups. Finally, analyses also showed that inbreeding B. stricta and A. thaliana have ~45% higher recombination per kilobase than outcrossing A. lyrata.     

Biology of Oxyeleotris heterodon and its major prey,Ophieleotris aporos,two floodplain sleepers (Pisces: Eleotrididae) of the Sepik River fishery,northern Papua New Guinea

Synopsis Oxyeleotris heterodon attains 483 mm standard length (1.83 kg) and Ophieleotris aporos 245 mm (0.171 kg). Both species feature significantly in the local fishery in lowlands. Ophieleotris aporos is approximately one hundred times more abundant than Ox. heterodon in catches and landings which were influenced by river flood conditions in both species. Oxyeleotris heterodon is predominantly piscivorous but also eats Macrobrachium spp. prawns; fish prey consumed are almost exclusively Op. aporos. Ophieleotris aporos is omnivorous and feeds mainly on aquatic insects. Condition, fat deposition, feeding and reproduction in Op. aporos were related to the flood cycle with increases in the flood season; in Ox. heterodon variations in these factors related more to the availability of Op. aporos, seasonal changes being less marked. Ophieleotris aporos matures at a small size, has large gonads, small eggs and is highly fecund; Ox. heterodon exhibited opposite trends in these life-history characteristics by comparison. Reproductive styles adopted by the two species are interpreted in relation to the different predation pressures they experience. Oxyeleotris heterodon may not be adapted to high adult mortality and the fisheries implications of this are discussed.     

Wood essential oils of two endemic trees from New Caledonia: Callitris sulcata (Parl.) Schltr. and Callitris neocaledonica Dummer

The essential oils obtained by hydrodistillation of pieces of dead trunks of Callitris sulcata (Parlatore) Schlechter and Callitris neocaledonica Dummer were investigated by gas chromatography, mass spectrometry and NMR spectroscopy. Analyses evidenced the presence of rare natural compounds: both essential oils are exclusively sesquiterpenic with nevertheless remarkable difference: C. sulcata essential oil was dominated by β-barbatene and thujopsene while C. neocaledonica was characterized by high levels of guaiane- and eudesmane-type structures (eudesmols, guaiol and related components). The biochemical correlations between the major components of each species are discussed and the relationship between the two species is commented.     

Germacranolides,a guaianolide with a β-lactone ring and further constituents from Grazielia species

An investigation of three Grazielia species afforded, in addition to known compounds, several new sesquiterpene lactones, eight germacranolides, two melampolides and one guaianolide as well as three diterpenes, two geranylgeraniol derivatives and a labda-diene. Three of the sesquiterpene lactones had an additional β-lactone ring, one an acid function, and two others unusual ester functions. The structures were elucidated by spectroscopic methods and some chemical transformations. The chemotaxonomic situation is discussed briefly.     

Screening the dermatological potential of Plectranthus species components: antioxidant and inhibitory capacities over elastase,collagenase and tyrosinase

A series of Plectranthus spp. plant extracts (aqueous, acetonic, methanolic and ethyl acetic) obtained from eight different species, and previously isolated compounds (ranging from polyphenols, diterpenes and triterpenes), were assayed for in vitro inhibition of the skin-related enzymes tyrosinase, collagenase and elastase, and for studying their antioxidant properties. The ethyl acetic extracts of P. grandidentatus and P. ecklonii registered the highest antioxidant activity, whereas acetonic, methanolic and ethyl acetic extracts of P. ecklonii, P. grandidentatus, P. madagascariensis and P. saccatus concerning the enzymatic inhibition assays revealed high anti-tyrosinase and anti-collagenase activities. From the isolated compounds tested, abietane diterpenes and triterpenes were highly active against tyrosinase and elastase activity. Overall, the experimental results showed the powerful antioxidant and inhibitory action on skin-related enzymes tyrosinase, collagenase and elastase of Plectranthus spp. extracts and/or isolated compounds, supporting their further research as bioactive metabolites against skin sagging and hyperpigmentation in cosmetic and pharmaceutical formulations.     

Tetraploid European Salicornia species are best interpreted as ecotypes of multiple origin

Salicornia procumbens and S. stricta are two tetraploid European salt marsh species of locally adjacent but ecologically differentiated distribution. Whereas S. procumbens grows in the lowest part of the salt marsh, it is replaced by S. stricta in the middle part (and diploid Salicornias in the upper part). Using AFLPs and a reciprocal transplantation experiment, we investigated whether the two species represent distinct evolutionary lineages. The analysis of AFLP variation clearly showed that both species are not monophyletic. Also, accessions do not cluster according to geographical origin. The transplantation experiment revealed that S. procumbens shows significantly reduced fitness when transplanted into the habitat of S. stricta. Reduction of fitness of S. stricta in the habitat of S. procumbens is less obvious. In both habitats S. procumbens performs better than S. stricta in terms of seed production and dry weight. On the background of these results, it is hypothesized that S. procumbens and S. stricta represent intraspecific ecotypes which originated repeatedly in adaptation to their specific environments and which dispersed widely. We hypothesize that the ecologically vicariant distribution of S. procumbens and S. stricta along the inundation gradient in the saltmarsh in spite of their good performance in the respective non-native habitats results from strong selection during seed germination and seedling establishment. Reproductive isolation between locally adjacent or even intermingled ecotypes is suggested to be achieved by high levels of selfing.     

Two novel species representing a new clade and cluster of Phytophthora

Phytophthora stricta sp. nov. and Phytophthora macilentosa sp. nov. are described based on morphological, physiological and molecular characters in this study. Phytophthora stricta represents a previously unknown clade in the rRNA internal transcribed spacer (ITS)-based phylogeny. Phytophthora macilentosa, along with nine other species, consistently forms a high temperature-tolerant cluster within ITS clade 9. These observations are supported by the sequence analysis of the mitochondrial cytochrome c oxidase 1 gene. Both species are heterothallic and all examined isolates are A1 mating type. Phytophthora stricta produces nonpapillate and slightly caducous sporangia. This species is named after its characteristic constrictions on sporangiophores. Phytophthora macilentosa produces nonpapillate and noncaducous sporangia, which are mostly elongated obpyriform with a high length to breadth ratio. Both species were recovered from irrigation water of an ornamental plant nursery in Mississippi, USA and P. stricta was also recovered from stream water in Virginia, USA.