A galloylated cyanogenic glycoside from the Australian endemic rainforest tree Elaeocarpus sericopetalus (Elaeocarpaceae)

A cyanogenic glycoside - 6'-O-galloylsambunigrin - has been isolated from the foliage of the Australian tropical rainforest tree species Elaeocarpus sericopetalus F. Muell. (Elaeocarpaceae). This is the first formal characterisation of a cyanogenic constituent in the Elaeocarpaceae family, and only the second in the order Malvales. 6'-O-galloylsambunigrin was identified as the principal glycoside, accounting for 91% of total cyanogen in a leaf methanol extract. Preliminary analyses indicated that the remaining cyanogen content may comprise small quantities of sambunigrin, as well as di- and tri-gallates of sambunigrin. E. sericopetalus was found to have foliar concentrations of cyanogenic glycosides among the highest reported for tree leaves, up to 5.2 mg CN g(-1) dry wt.     

Variation of cyanogenesis in some plant species of the midwestern United States

The frequency of cyanogenesis of 48 species of vascular plants was examined by testing 30 individuals from five populations of each species for release of cyanide. The rate at which cyanide was released and the amount of cyanide released varied widely among individuals of a population and among populations of a species. For many taxa, the frequency of cyanogenesis was highly variable among populations. Of the species examined, 20 have not been reported previously as being cyanogenic.     

Ontogenetic and temporal trajectories of chemical defence in a cyanogenic eucalypt

Many studies have shown that similarly aged plants within a species or population can vary markedly in the concentration of defence compounds they deploy to protect themselves from herbivores. Some studies have also shown that the concentration of these compounds can change with development, but no empirical research has mapped such an ontogenetic trajectory in detail. To do this, we grew cyanogenic Eucalyptus yarraensis seedlings from three half-sibling families under constant glasshouse conditions, and followed their foliar cyanogenic glycoside (prunasin) concentration over time for 338 days after sowing (DAS). Plants in all families followed a similar temporal pattern. Plants increased in foliar prunasin concentration from a very low level (10 μg cyanide (CN) equivalents g⁻¹) in their first leaves, to a maximum of, on average, 1.2 mg CN g⁻¹ at about 240 DAS. From 240 to 338 DAS, prunasin concentration gradually decreased to around 0.7 mg CN g⁻¹. Significant differences between families in maximum prunasin concentration were detected, but none were detected in the time at which this maximum occurred. In parallel with these changes in prunasin concentration, we detected an approximately linear increase in leaf mass per unit leaf area (LMA) with time, which reflected a change from juvenile to adult-like leaf anatomy. When ontogenetic trajectories of prunasin against LMA were constructed, we failed to detect a significant difference between families in the LMA at which maximum prunasin concentration occurred. This remarkable similarity in the temporal and ontogenetic trajectories between individuals, even from geographically remote families, is discussed in relation to a theoretical model for ontogenetic changes in plant defence. Our results show that ontogeny can constrain the expression of plant chemical defense and that chemical defense changes in a nonlinear fashion with ontogeny.     

Hydrogen cyanide release during feeding of generalist and specialist lepidopteran larvae on a cyanogenic plant, Passiflora capsularis

Abstract.  The hydrogen cyanide-based interaction of a strongly cyanogenic plant, Passiflora capsularis , and larvae of two insect herbivores, a generalist ( Spodoptera frugiperda ) and a specialist ( Heliconius erato ), is examined in terms of the combined kinetics of the feeding process and the simultaneous hydrogen cyanide (HCN) liberation, as compared with the natural kinetics of hydrogen cyanide evolution by plant-leaf tissue. There are marked differences in acceptance of P. capsularis by third-instar larvae of specialist and generalist species. The former, H. erato , display a parsimonious ingestion rate of 0.74 ± 0.15 mg (fresh weight) min⁻¹ comprising 18% active feeding time, whereas S. frugiperda larvae show a more erratic and restrained feeding involving 4% of the time at 0.45 ± 0.14 mg min⁻¹. These S. frugiperda larvae ingest 124.4 ± 8.3 mg (fw) of the non-cyanogeneic Spinacia oleracea leaves in 24 h compared with only 74.7 ± 20.1 mg of P. capsularis in the same period. The total hydrogen cyanide released naturally from wild specimens of P. capsularis plants is in the range 326–3901 μg g⁻¹. Hydrogen cyanide evolution from macerated P. capsularis leaves takes place along a hyperbolic function with time and initial velocities of cyanide evolution are a linear function of total hydrogen cyanide. When feeding on P. capsularis leaves, H. erato releases only a minor fraction relative to total hydrogen cyanide (0.09%) and to the anticipated cyanide from the initial velocity (7%). By contrast, S. frugiperda evokes 5.8-fold more than the anticipated hydrogen cyanide release from the plant. The findings are interpreted as diverging strategies by generalist and specialist insects in the utilization of hydrogen cyanide in cyanogenic plants.     

Variation in defence strategies in two species of the genus Beilschmiedia under differing soil nutrient and rainfall conditions

The relationships between various leaf functional traits that are important in plant growth (e.g., specific leaf area) have been investigated in recent studies; however, research in this context on plants that are highly protected by chemical defences, particularly resource-demanding nitrogen-based defence, is lacking. We collected leaves from cyanogenic (N-defended) Beilschmiedia collina B. Hyland and acyanogenic (C-defended) Beilschmiedia tooram (F. M. Bailey) B. Hyland at high- and low-soil nutrient sites in two consecutive years that varied significantly in rainfall. We then measured the relationships between chemical defence and morphological and functional leaf traits under the different environmental conditions. We found that the two species differed significantly in their resource allocation to defence as well as leaf morphology and function. The N defended species had a higher leaf nitrogen concentration, whereas the C-defended species had higher amounts of C-based chemical defences (i.e., total phenolics and condensed tannins). The C-defended species also tended to have higher force to fracture and increased leaf toughness. In B. collina, cyanogenic glycoside concentration was higher with higher rainfall, but not with higher soil nutrients. Total phenolic concentration was higher at the high soil nutrient site in B. tooram, but lower in B. collina; however, with higher rainfall an increase was found in B. tooram, while phenolics decreased in B. collina. Condensed tannin concentration decreased in both species with rainfall and nutrient availability. We conclude that chemical defence is correlated with leaf functional traits and that variation in environmental resources affects this correlation.     

Gynocardin from Baileyoxylon lanceolatum and a revision of cyanogenic glycosides in Achariaceae

The cyclopentenone cyanhydrin glycoside gynocardin was the only cyanogen isolated from foliage of monotypic Australian rainforest tree, Baileyoxylon lanceolatum (Achariaceae). The presence of cyanogenic compounds in plants can have considerable taxonomic utility. A review of previous reports of cyanogenesis in the recently revised Achariaceae revealed distinct taxonomic patterns as well as inconsistencies in the reporting of cyanogenic compounds. This variation appears to be due to tissue level localisation of cyanogenic compounds as well as discrepancies in results obtained from different detection methods. Recommendations are made for future investigations.     

Linamarase and other β-glucosidases are present in the cell walls of Trifolium repens L. leaves

Linamarase (EC 3.2.1.21) is a specialized -glucosidase that hydrolyses the cyanogenic glucoside linamarin. Two clones of Trifolium repens L. derived from natural populations, of which one clone exhibited linamarase activity, were used in a comparative study to try to establish the localization of linamarase and other -glucosidases. Two methods were used: the first one was vacuum infiltration of intact leaf cells, followed by centrifugation. A significant amount of linamarase and -glucosidase activity could be extracted from intact tissue by a 0.25 M NaCl solution, indicating that these activities are localized in the apoplast. The second method, immuno-cytofluorescense of microtome sections, confirmed this. It was found that linamarase and other -glucosidases are present in the cell walls, especially those of the epidermal cells, and in the cuticle. However their presence in the cell walls of other tissues i.e. walls of the vessels, could not be excluded. No difference in distribution could be detected between linamarase and other -glucosidases.     

Molecular cloning of the cDNA coding for the (R)-(+)-mandelonitrile lyase of Prunus amygdalus: temporal and spatial expression patterns in flowers and mature seeds

A gene highly expressed in the floral organs of almond (Prunus amygdalus Batsch), and coding for the cyanogenic enzyme (R)-(+)-mandelonitrile lyase (EC 4.1.2.10), has been identified and the full-length cDNA sequenced. The temporal expression pattern in maturing seeds and during floral development was analyzed by RNA blot, and the highest mRNA levels were detected in floral tissues. The spatial mRNA accumulation pattern in almond flower buds was also analyzed by in-situ hybridization. The mRNA levels were compared during seed maturation and floral development in fruit and floral samples from cultivars classified as homozygous or heterozygous for the sweet-almond trait or homozygous for the bitter trait. No correlation was found between these characteristics and levels of mandelonitrile lyase mRNA, suggesting that the presence of this protein is not the limiting factor in the production of hydrogen cyanide. Received: 3 December 1997 / Accepted: 18 April 1998     

Cyanogenic glucosides and plant-insect interactions

Cyanogenic glucosides are phytoanticipins known to be present in more than 2500 plant species. They are considered to have an important role in plant defense against herbivores due to bitter taste and release of toxic hydrogen cyanide upon tissue disruption. Some specialized herbivores, especially insects, preferentially feed on cyanogenic plants. Such herbivores have acquired the ability to metabolize cyanogenic glucosides or to sequester them for use in their predator defense. A few species of Arthropoda (within Diplopoda, Chilopoda, Insecta) are able to de novo synthesize cyanogenic glucosides and, in addition, some of these species are able to sequester cyanogenic glucosides from their host plant (Zygaenidae). Evolutionary aspects of these unique plant-insect interactions with focus on the enzyme systems involved in synthesis and degradation of cyanogenic glucosides are discussed.     

Competition between cyanogenic and acyanogenic morphs of Trifolium repens

Summary To investigate the cost of the dimorphic cyanogenic system in Trifolium repens L., genotypes of the cyanogenic (T_c) and acyanogenic (T_a) morphs were grown in mixtures over a range of ratios and in pure stands at two levels of total density (low in a first experiment, high in a second experiment). The principles of the competition analysis employed were those related to the inverse linear model response. The morphs were compared using two interaction indices, the substitution rate and the relative resource total (RRT). The relative fitness of the two morphs, i.e. biomass and number of flowers per plant, suggests that the T_a morph has a competitive advantage over the T_c morph.