Identification and characterization of JWH-122 used as new ingredient in "Spice-like" herbal incenses.

Recently, several cases across Germany were reported where teenagers were hospitalized showing severe side effects after consumption of a new "Spice-like" herbal incense called "Lava red". The active component of "Lava red", obtained from German internet shops, was isolated by silica gel column chromatography and the structure was elucidated by NMR methods. It is a known N-alkyl-3-(1-naphthoyl)indole (CAS No.

Pyrrolizidine alkaloids in pollen and pollen products.

Recently, 1,2-dehydropyrrolizidine alkaloid (PA) ester alkaloids, found predominantly as their N-oxides (PANOs, pyrrolizidine N-oxides), have been reported in both honey and in pollen obtained directly from PA plants and pollen loads collected by bees, raising the possibility of health risks for consumers of these products. We confirm these findings in regard to floral pollen, using pollen collected directly from flowers of the known PA plants Senecio jacobaea, S. vernalis, Echium vulgare and pollinia of Phalaenopsis hybrids, and we extend analyses of 1,2-unsaturated PAs and 1,2-unsaturated PANOs to include bee-pollen products currently being sold in supermarkets and on the Internet as food supplements.

Feeding deterrence and detrimental effects of pyrrolizidine alkaloids fed to honey bees (Apis mellifera).

Recent studies have shown the occurrence of plant derived pyrrolizidine alkaloids (PAs) in retail honeys and pollen loads, but little is known about how these compounds influence the fitness of foraging honey bees. In feeding experiments, we tested a mix of tertiary PAs and the corresponding N-oxides from Senecio vernalis, pure monocrotaline, and 1,2-dihydromonocrotaline in 50% (w/w) sucrose solutions. The bees were analyzed chemically to correlate the observed effects to the ingested amount of PAs.

Pyrrolizidine alkaloid biosynthesis in Phalaenopsis orchids: developmental expression of alkaloid-specific homospermidine synthase in root tips and young flower buds.

Pyrrolizidine alkaloids (PAs) are typical compounds of plant secondary metabolism and are believed to be part of the plant's chemical defense. Within the monocotyledonous plants, PAs have been described in only a few genera, mainly orchids, including Phalaenopsis. Because phylogenetic analyses suggest an independent origin of PA biosynthesis within the monocot lineage, we have analyzed the developmentally regulated expression of homospermidine synthase (HSS), the first pathway-specific enzyme of PA biosynthesis, at the cell level.

Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases.

The endemic Mexican genus Pittocaulon (subtribe Tussilagininae, tribe Senecioneae, Asteraceae) belongs to a monophyletic group of genera distributed in Mexico and North America. The five Pittocaulon species represent shrubs with broom-like succulent branches. All species were found to contain pyrrolizidine alkaloids (PAs).

Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids.

Arctiids which as larvae sequester pyrrolizidine alkaloids (PAs) from their food plants are known to synthesize insect-specific PAs by esterifying necine bases derived from plant PAs with necic acids of insect origin. There are two classes of insect PAs, the creatonotines and the callimorphines. The creatonotines contain as necic acids either 2-hydroxy-3-methylbutyric acid (creatonotine A) or 2-hydroxy-3-methylpentanoic acid (creatonotine B).

Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae).

Pyrrolizidine alkaloids (PAs) of the macrocyclic senecionine type are secondary metabolites characteristic for most species of the genus Senecio (Asteraceae). These PAs are deterrent and toxic to most vertebrates and insects and provide plants with a chemical defense against herbivores. We studied the PA composition of 24 out of 26 species of Senecio section Jacobaea using GC-MS.

Direct evidence for membrane transport of host-plant-derived pyrrolizidine alkaloid N-oxides in two leaf beetle genera.

The chrysomelid leaf beetles Longitarsus jacobaeae, Oreina cacaliae, and O. speciosissima sequester pyrrolizidine alkaloids from their asteracean host plants and store them as nontoxic N-oxides. Previous analyses showed that Longitarsus is able to N-oxidize protoxic tertiary PAs, but did not resolve in which form N-oxides are taken up.

Disentangling food quality from resistance against parasitoids: diet choice by a generalist caterpillar.

The relative importance of food quality and enemy-reduced space is a central but unresolved issue in the evolutionary ecology of host use by phytophagous insects. Indeed, a practical obstacle to experimentally disentangling the functional roles of these factors is the host specificity of insect herbivores, particularly toxic plant specialists. In this study, we employ a toxic plant generalist to uniquely disentangle these alternative explanations.

Sequestration and metabolism of protoxic pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults.

Several neotropical leaf-beetles of the genus Platyphora ingest and specifically metabolize plant acquired pyrrolizidine alkaloids (PAs) of the lycopsamine type (e.g., rinderine or intermedine) and enrich the processed alkaloids in their exocrine defensive secretions.

Effects of rust infection with Puccinia lagenophorae on pyrrolizidine alkaloids in Senecio vulgaris.

The pyrrolizidine alkaloid pattern of Senecio vulgaris, infected with the obligate fungal pathogen Puccinia lagenophorae was analysed quantitatively in comparison to noninfected controls. The fungal infection did not significantly affect the plant's total PA contents and concentrations. In comparison to the controls the fungal-infected plants showed significantly lower PA concentrations in the capitula and roots but not the shoots which contain 90% of total PAs.