Phenolic glycosides and condensed tannins in Salix sericea, S. eriocephala and their F1 hybrids: not all hybrids are created equal

The performance of hybrids depends upon the inheritance and expression of resistance traits. Secondary chemicals are one such resistance trait. In this study, we measured the concentrations of phenolic glycosides and condensed tannins in parental and F1 hybrid willows to examine the sources of chemical variation among hybrids. S. sericea produces phenolic glycosides, salicortin and 2'-cinnamoylsalicortin, and low concentrations of condensed tannin in its leaves. In contrast, S. eriocephala produces no phenolic glycosides but high concentrations of condensed tannins in its leaves. These traits are inherited quantitatively in hybrids. On average, F1 hybrids are intermediate for condensed tannins, suggesting predominantly additive inheritance or balanced ambidirectional dominance of this defensive chemical from the parental species. In contrast, the concentration of phenolic glycosides is lower than the parental midpoint, indicating directional dominance. However, there is extensive variation among F1 hybrids. The concentration of tannin and phenolic glycosides in F1 hybrid families is either (1) lower than the midpoint, (2) higher than the midpoint, or (3) indistinguishable from the midpoint of the two parental taxa. It appears that the production of the phenolic glycosides, especially 2'-cinnamoylsalicortin, is controlled by one or more recessive alleles. We also observed a two-fold or greater difference in concentration between some hybrid families. We discuss how chemical variation may effect the relative susceptibility of hybrid willows to herbivores.     

Frequency of cyanogenesis in tropical rainforests of far north Queensland, Australia

BACKGROUND AND AIMS: Plant cyanogenesis is the release of toxic cyanide from endogenous cyanide-containing compounds, typically cyanogenic glycosides. Despite a large body of phytochemical, taxonomic and ecological work on cyanogenic species, little is known of their frequency in natural plant communities. This study aimed to investigate the frequency of cyanogenesis in Australian tropical rainforests. Secondary aims were to quantify the cyanogenic glycoside content of tissues, to investigate intra-plant and intra-population variation in cyanogenic glycoside concentration and to appraise the potential chemotaxonomic significance of any findings in relation to the distribution of cyanogenesis in related taxa. METHODS: All species in six 200 m(2) plots at each of five sites across lowland, upland and highland tropical rainforest were screened for cyanogenesis using Feigl-Anger indicator papers. The concentrations of cyanogenic glycosides were accurately determined for all cyanogenic individuals. KEY RESULTS: Over 400 species from 87 plant families were screened. Overall, 18 species (4.5 %) were cyanogenic, accounting for 7.3 % of total stem basal area. Cyanogenesis has not previously been reported for 17 of the 18 species, 13 of which are endemic to Australia. Several species belong to plant families or orders in which cyanogenesis has been little reported, if at all (e.g. Elaeocarpaceae, Myrsinaceae, Araliaceae and Lamiaceae). A number of species contained concentrations of cyanogenic glycosides among the highest ever reported for mature leaves-up to 5.2 mg CN g(-1) d. wt, for example, in leaves of Elaeocarpus sericopetalus. There was significant variation in cyanogenic glycoside concentration within individuals; young leaves and reproductive tissues typically had higher cyanogen content. In addition, there was substantial variation in cyanogenic glycoside content within populations of single species. CONCLUSIONS: This study expands the limited knowledge of the frequency of cyanogenesis in natural plant communities, includes novel reports of cyanogenesis among a range of taxa and characterizes patterns in intra-plant and intra-population variation of cyanogensis.     

COMPOUNDS FROM THE STIGMAS OF TEN SPECIES

Extracts of the intact stigmatic surface of 10 species from different families contained little or no free sugar. The principal components of the extracts consisted of phenolic (anthocyanins, flavonoids, cinnamic acids) and lipid compounds. The phenolic compounds occurred as glycosides or esters. Phenolic compounds could inhibit insects and diseases, stimulate or inhibit pollen germination, or provide specificity to the pollen selection-germination process of the stigma by interacting with growth-regulators or related compounds.     

Sea Cucumbers Triterpene Glycosides, the Recent Progress in Structural Elucidation and Chemotaxonomy

Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). Majority of the glycosides belong to holostane type (lanostane derivatives with 18(20)-lactone). Carbohydrate chains of these glycosides contain xylose, glucose, quinovose, 3-O-methylglucose and 3-O-methyl sylose. During the last 5 years, main investigations were focused on holothurians belonging to the order Dendrochirotida collected in the North Pacific, North Atlantic, Antarctic and in subtropical waters. The glycosides of holothurians belonging to the order Aspidochirotida have also been studied. The most uncommon structural features of carbohydrate chains of new glycosides were: (1) the presence of quinovose as fifth terminal monosaccharide unit and the presence of two quinovose residues; (2) the presence of glucose instead of common xylose as fifth terminal monosaccharide unit; (3) trisaccharide carbohydrate chain; (4) the presence of two 3-O-methylxylose terminal monosaccharide units; (5) the presence of sulfate group at C-3 of quinovose residue. New glycosides without lactone or with 18(16)-lactone and having shortened side chains have also been isolated. The presence of 17α and 12α-hydroxyls, which are characteristic for glycosides from holothurians belonging to the family Holothuriidae (Aspidochirotida) in glycosides of dendrochirotids confirms parallel and relatively independent character of evolution of glycosides. All three families belonging to the order Aspidochirotida: Holothuriidae, Stichopodidae and Synallactidae have similar and parallel trends in evolution of the glycosides carbohydrate chains, namely from non-sulfated hexaosides to sulfated tetraosides. Sets of aglycones in glycosides from holothurians belonging to the genus Cucumaria (Cucumariidae, Dendrochirotida) are specific for each species. The carbohydrate chains are similar in all representatives of the genus Cucumaria.     

Flavonoids of Astilbe and Rodgersia compared to Aruncus

The flavonoid profiles of Astilbe (four taxa studied) and Rodgersia (two taxa studied) are based on simple flavonol glycosides. Astilbe has 3-O-mono-, 3-O-di-, and 3-O-triglycosides of kaempferol, quercetin, and myricetin, while Rodgersia has only mono- and diglycosides of kaempferol and quercetin. Astilbe×arendsii was also shown to accumulate dihydrochalcone glycosides. The flavonoid profile of Rodgersia is the simplest recorded so far in the herbaceous Saxifragaceae. The flavonoids of two species of Aruncus were shown to be based upon kaempferol and quercetin 3-O-mono- and 3-O-diglycosides. One of the species also exhibited an eriodictyol glycoside. The triglycoside differences were not considered important, but the differences in myricetin occurrences were taken as evidence against derivation of Saxifragaceae from an Aruncus-like ancestor. Should such an event be proposed, however, serious consideration would have to be given to the current pattern of myricetin occurrence in the two families.     

Leaf flavonoids of Amborella trichopoda

The leaf flavonoids of Amborella trichopoda were examined and two kaempterol glycosides were detected. Procyanidin was also present. These results are similar to the flavonoid pattern in other families of the Laurales and it is suggested that simple flavonol glycosides are a primitive feature in the order.     

青藏高原东南部天然草地主要有毒植物调查研究

对青藏高原东南部的川西北天然草地主要有毒植物的种类、毒物成分和分布作了系统的调查与研究,首次报道了该区域天然草地有毒植物名录,统计出该区主要有毒植物226种,隶属于33科77属。有毒植物所含主要毒物成分可分为生物碱、苷类化合物、萜类化合物、苯酮类化合物、酚类及其衍生物和简单有机物等6大类。有毒植物在亚高山草甸草地中分布最多,有157种,其次是亚高山灌丛草地、高山草甸草地、高山灌丛草地和高寒沼泽化草甸草地。本调查研究为青藏高原东南部天然草地主要有毒植物的防除和开发利用奠定了基础。     

Iridoid and caffeoyl phenylethanoid glycosides of the endangered carnivorous plant Pinguicula lusitanica L. (Lentibulariaceae)

This work reports for the first time the identification of the major compounds of Pinguicula lusitanica, an endangered carnivorous plant species, using minimal amounts of plant material. A methanol extract was prepared from in vitro cultured plantlets and analyzed by HPLC–SPE–NMR/HPLC–MS. Three iridoid and five caffeoyl phenylethanoid glycosides were identified. These groups of natural compounds were previously reported in the Lentibulariaceae family and have been used as chemotaxonomic markers in related families.     

Light and Nutrient Dependent Responses in Secondary Metabolites of Plantago lanceolata Offspring Are Due to Phenotypic Plasticity in Experimental Grasslands

A few studies in the past have shown that plant diversity in terms of species richness and functional composition can modify plant defense chemistry. However, it is not yet clear to what extent genetic differentiation of plant chemotypes or phenotypic plasticity in response to diversity-induced variation in growth conditions or a combination of both is responsible for this pattern. We collected seed families of ribwort plantain (Plantago lanceolata) from six-year old experimental grasslands of varying plant diversity (Jena Experiment). The offspring of these seed families was grown under standardized conditions with two levels of light and nutrients. The iridoid glycosides, catalpol and aucubin, and verbascoside, a caffeoyl phenylethanoid glycoside, were measured in roots and shoots. Although offspring of different seed families differed in the tissue concentrations of defensive metabolites, plant diversity in the mothers'' environment did not explain the variation in the measured defensive metabolites of P. lanceolata offspring. However secondary metabolite levels in roots and shoots were strongly affected by light and nutrient availability. Highest concentrations of iridoid glycosides and verbascoside were found under high light conditions, and nutrient availability had positive effects on iridoid glycoside concentrations in plants grown under high light conditions. However, verbascoside concentrations decreased under high levels of nutrients irrespective of light. The data from our greenhouse study show that phenotypic plasticity in response to environmental variation rather than genetic differentiation in response to plant community diversity is responsible for variation in secondary metabolite concentrations of P. lanceolata in the six-year old communities of the grassland biodiversity experiment. Due to its large phenotypic plasticity P. lanceolata has the potential for a fast and efficient adjustment to varying environmental conditions in plant communities of different species richness and functional composition.     

The interplay between toxin-releasing β-glucosidase and plant iridoid glycosides impairs larval development in a generalist caterpillar, Grammia incorrupta (Arctiidae)

Herbivores with polyphagous feeding habits must cope with a diet that varies in quality. One of the most important sources of this variation in host plant suitability is plant secondary chemistry. We examined how feeding on plants containing one such group of compounds, the iridoid glycosides, might affect the growth and enzymatic activity in a polyphagous caterpillar that feeds on over 80 plant species in 50 different families. Larvae of the polyphagous arctiid, Grammia incorrupta, were reared exclusively on one of two plant species, one of which contains iridoid glycosides (Plantago lanceolata, Plantaginaceae) while the other does not (Taraxacum officinale, Asteraceae). Larval weight was measured on the two host plants, and midgut homogenates of last instar larvae were then assayed for activity and kinetic properties of β-glucosidases, using both a standard substrate, 4-nitrophenyl-β-D-glucose (NPβGlc), and the iridoid glycoside aucubin, one of the two main iridoid glycosides in P. lanceolata. Larvae feeding on P. lanceolata weighed significantly less and developed more slowly compared to larvae on T. officinale. While the larval midgut β-glucosidase activity determined with NPβGlc was significantly decreased when fed on P. lanceolata, aucubin was substantially hydrolyzed and the larval β-glucosidase activity towards both substrates correlated negatively with larval weight. Our results demonstrate that host plants containing high concentrations of iridoid glycosides have a negative impact on larval development of this generalist insect herbivore. This is most likely due to the hydrolysis of plant glycosides in the larval midgut which results in the release of toxic aglycones. Linking the reduced larval weight to the toxin-releasing action of an iridoid glycoside cleaving β-glucosidase, our results thus support the detoxification limitation hypothesis, suggesting fitness costs for the larvae feeding solely on P. lanceolata. Thus, in addition to the adaptive regulation of midgut β-glucosidase activity, host plant switching as a behavioral adaptation might be a prerequisite for generalist herbivores that allows them to circumvent the negative effects of plant secondary compounds.     

Selective sequestration of iridoid glycosides from their host plants in Longitarsus flea beetles

We investigated in eight species of the flea beetles genus Longitarsus (Coleoptera, Chrysomelidae) whether the beetles take up iridoid glycosides from their host plants of the Lamiaceae, Plantaginaceae, and Scrophulariaceae. Five of the beetle species, L. australis, L. lewisii, L. melanocephalus, L. nigrofasciatus, and L. tabidus, could be shown to sequester iridoid glycosides in concentrations between 0.40 and 1.55% of their dry weight. Eight different iridoid glycosides, acetylharpagide, ajugol, aucubin, catalpol, 8-epi-loganic acid, gardoside, geniposidic acid, and harpagide could be identified in the host plants, yet only aucubin and catalpol are sequestered by the beetles. No iridoid glycosides could be detected in the beetles if neither aucubin nor catalpol were present in the host plant, as in L. minusculus on Stachys recta (acetylharpagide only) and in L. salviae on Salvia pratensis (no iridoid glycosides). In one beetle species, L. luridus, we could not detect any iridoid glycosides although its field host, Plantago lanceolata, had considerable amounts of aucubin and catalpol plus two further iridoids. The five sequestering Longitarsus species differ in their capacity to store the compounds and in their affinity for catalpol relative to aucubin.     

Size class structure and tree dispersion patterns in old-growth cedar-hemlock forests of the northern Rocky Mountains (USA)

Summary The relationship between the food selection of four leaf beetle species (Phratora vitellinae, Plagiodera versicolora, Lochmaea capreae, Galerucella lineola) and the phenolic glycosides of willow (Salix spp.) leaves was tested in laboratory food choice experiments. Four willow species native to the study area (Eastern Finland) and four introduced, cultivated willows were tested.The willow species exhibited profound differences in their phenolic glycoside composition and total concentration. The food selection patterns of the leaf beetles followed closely the phenolic glycoside spectra of the willow species. Both the total amount and the composition of phenolic glycosides affected the feeding by the beetles. Phenolic glycosides apparently have both stimulatory and inhibitory influences on leaf beetle feeding depending on the degree of adaptation of a particular insect. Very rare glycosides or exceptional combination of several glycoside types seem to provide certain willow species with high level of resistance against most herbivorous insects. Analogously the average absolute amount of leaf beetle feeding was lower on the introduced willows than on the native species to which the local herbivores have a good opportunity to become adapted.     

Cyanogenic glycosides: a case study for evolution and application of cytochromes P450

Cyanogenic glycosides are ancient biomolecules found in more than 2,650 higher plant species as well as in a few arthropod species. Cyanogenic glycosides are amino acid-derived β-glycosides of α-hydroxynitriles. In analogy to cyanogenic plants, cyanogenic arthropods may use cyanogenic glycosides as defence compounds. Many of these arthropod species have been shown to de novo synthesize cyanogenic glycosides by biochemical pathways that involve identical intermediates to those known from plants, while the ability to sequester cyanogenic glycosides appears to be restricted to Lepidopteran species. In plants, two atypical multifunctional cytochromes P450 and a soluble family 1 glycosyltransferase form a metabolon to facilitate channelling of the otherwise toxic and reactive intermediates to the end product in the pathway, the cyanogenic glycoside. The glucosinolate pathway present in Brassicales and the pathway for cyanoalk(en)yl glucoside synthesis such as rhodiocyanosides A and D in Lotus japonicus exemplify how cytochromes P450 in the course of evolution may be recruited for novel pathways. The use of metabolic engineering using cytochromes P450 involved in biosynthesis of cyanogenic glycosides allows for the generation of acyanogenic cassava plants or cyanogenic Arabidopsis thaliana plants as well as L. japonicus and A. thaliana plants with altered cyanogenic, cyanoalkenyl or glucosinolate profiles.     

Veronica: Acylated flavone glycosides as chemosystematic markers

HPLC/DAD and LC–MS of an extract of Veronica spicata (subgenus Pseudolysimachium, Plantaginaceae) revealed the presence of six 6-hydroxyluteolin glycosides acylated with phenolic acids, three of which are new compounds and which we called spicosides. A flavonoid survey of seven more species belonging to V. subgenus Pseudolysimachium and eight species of V. subgenus Pentasepalae showed that all the Pseudolysimachium species and four of the Pentasepalae species produced 6-hydroxyflavone glycosides, whereas the remaining four Pentasepalae species contained acetylated 8-hydroxyflavone glycosides instead. Spicosides appeared to be common in subgenus Pseudolysimachium (detected in five out of eight species), but we did not find them in subgenus Pentasepalae. Previously, acetylated 8-hydroxyflavone glycosides have been isolated from or detected in eight species of V. subgenus Pentasepalae (in 13 species altogether including the new results) and seven species of V. subgenus Pocilla. However, 6-hydroxyflavone glycosides occur in some other species of these subgenera. The results are discussed in an evolutionary context.     

Chemosystematic studies in the chrysobalanaceae. I. Flavonoids in Parinari

A survey of flavonoids in 31 Asian, African and Neotropical species of Parinari showed a predominance of flavonol glycosides based on myricetin, quercertin, and kaemp-ferol. The African taxa split into two groups based on the presence or absence of myricetin glycosides. The Neotropical taxa, a complex of closely related species, are chemically very similar to each other and lack myre?etin, as does one group of African species. The Asian taxa are similar to the Neotropical ones in their flavonoid patterns and lack of myricetin glycosides. The presence of myricetin considered a primitive flavonoid character, suggest that te African species pro-ducing this flavonol represent a primitive nucleus eastward and westward ex-pansion to two myricetin-lacking phytogeographic lines. This hypothesis is in agreement with current proposals for geographic evolution in the Chrysobalanaceae.     

Evolutionary assembly of the milkweed fauna: cytochrome oxidase I and the age of Tetraopes beetles

The insects that feed on the related plant families Apocynaceae and Asclepiadaceae (here collectively termed "milkweeds") comprise a "component community" of highly specialized, distinctive lineages of species that frequently sequester toxic cardiac glycosides from their host plants for defense against predators and are thus often aposematic, advertising their consequent unpalatability. Such sets of specialized lineages provide opportunities for comparative studies of the rate of adaptation, diversification, and habitat-related effects on molecular evolution. The cerambycid genus Tetraopes is the most diverse of the new world milkweed herbivores and the species are generally host specific, being restricted to single, different species of Asclepias, more often so than most other milkweed insects. Previous work revealed correspondence between the phylogeny of these beetles and that of their hosts. The present study provides analyses of near-complete DNA sequences for Tetraopes and relatives that are used to establish a molecular clock and temporal framework for Tetraopes evolution with their milkweed hosts.     

4种蔷薇属植物叶片黄酮含量的季节性变化

采用ＨＰＬＣ法对刺梨（Ｒｏｓａ ｒｏｘｂｕｒｇｈｉｉ Ｔｒａｔｔ．）等４种蔷薇属植物在不同生长季节叶片的总黄酮甙含量和甙元配比进行了分析测定。结果表明,不同采摘期的华西蔷薇（Ｒ．ｍｏｙｅｓｉｉ Ｈｅｍｓｌ．ｅｔ Ｗｉｌｓ．）绣球蔷薇（Ｒ．ｇｉｏｍｅｒａｔａ Ｒｅｈｄ．ｅ Ｗｉｌｓ．）和峨嵋蔷薇（Ｒ．ｏｍｅｉｅｎｓｉｓ Ｒｏｌｆｅ）的叶片总黄酮甙含量有较大的差异,一般在展叶期黄酮含量较低,随后叶片黄     

Cyanogenic constituents in woody plants in natural lowland rain forest in Costa Rica

Screening of fresh leaves and other plant organs revealed the presence of cyanogenesis in 25 species in 16 families out of a total of 488 species in 79 families vouchered in natural lowland rain forest in Costa Rica. In a qualitative screening of a random sample based on seven one-hectare inventories of woody plants, we found cyanogenesis in 4.0% of all species; these represented 2.5% of all individuals present, and 3.0% of the total basal area of stems. The frequency of occurrence of cyanogenic compounds was higher in reproductive plant parts than in leaves, and highest in pericarps. Cyanogenesis was found in Annona amazonica, Annona pittieri, Cymbopetalum costaricense, Tabebuia chrysantha, Sloanea tuerckheimii, Sapium laurifolium, Lecointea amazonica, Carpotroche platyptera, Klayana odorata, Byrsonima crispa, Miconia splendens, Inga acuminata, Chaunochiton kappleri, Passiflora ambigua, P. pittieri, P. talamancensis, P. vitifolia, Panopsis costaricensis, Faramea pawibractea, Paullinia capreolata, Pouteria amygdalicarpa, P. campechiana, P. subrotata, P. torta and Rinorea guatemalensis. Some taxonomic implications are discussed. The identity of cyanogenic constituents found in dried material of these species is presented, as is the total cyanogenic potential (CNp) of 11 positive species. The CNp ranged from less than 5 to approx. 2000 mg kg^-1 f.w. Several species were cyanogenic only in some individuals. A total of 463 species gave no positive test for cyanogenic glycosides. Tests on leaves and seeds of Ampelocera macrocarpa indicated the content of a rare and unknown volatile constituent.     

FLORAL PIGMENTATION STUDIES IN THE GENUS GOSSYPIUM. I. SPECIES SPECIFIC PIGMENTATION PATTERNS

Previous work on cotton flower pigments is outlined. The major flavonoids are glycosides of gossypetin, quercetin, and kampferol. Twelve flavonol glycosides have been tentatively isolated and identified, while a number of minor components remain unidentified. The gossypetin glycosides are gossypin, gossypitrin and a C₇-linked glycoside of unknown sugar residue. The quercetin glycosides include isoquercitrin, rutin, a third C₃-linked glycoside with unknown sugar residue, quercimeritrin and a second C₇-linked glycoside with sugar residue unknown. The kampferol glycosides include trifolin, kampferol rutinoside and 2 other C₃-linked glycosides with unknown sugar residues. The major anthocyanin throughout the genus is cyanidin. Mutants which affect visible flower color were studied in 3 species (G. arboreum, G. hirsutum, and G. barbadense). The majority of these mutants act to decrease or prevent the synthesis of gossypetin glycosides. The only exceptions to this are the mutants at the Y_a locus in G. arboreum, which affect all of the C₇-linked glycosides in one case, and in the other reduce over-all flavonol production. In all instances, the species could be positively identified by the residual array of pigments not affected by the mutant alleles concerned; i.e., visual similarity of phenotypes did not obscure the basic pattern of pigmentation characteristic of the different species.