Biosynthesis of Steroidal Alkaloids Are Coordinately Regulated and Differ Among Tomatoes in the Red-Fruited Clade

Background/rationale: We quantitatively profiled and genotyped two tomato populations representing diversity in the red-fruited clade to address the lack of knowledge regarding the chemical diversity, concentration, and genetic architecture controlling tomato steroidal alkaloids. Methods: We grew 107 genetically diverse fresh market, processing, land-race, and wild tomatoes in multiple environments. Nine steroidal alkaloids were quantified using ultra-high performance liquid chromatography tandem mass spectrometry. The diversity panel and a biparental population segregating for high alpha-tomatine, were genotyped to identify and validate quantitative trait loci (QTL) associated with steroidal alkaloids. Results: Land-races and wild material exhibited higher alkaloid concentrations and more chemical diversity. Average total content of steroidal alkaloids, often dominated by lycoperoside F/G/esculeoside A, ranged from 1.9 to 23.3 mg/100 g fresh weight across accessions. Land-race and wild cherry accessions distinctly clustered based on elevated early or late steroidal alkaloid concentrations. Significant correlations were observed among early and late steroidal alkaloids in a species-dependent manner. A QTL controlling multiple, early steroidal alkaloid pathway intermediates on chromosome 3 was identified by genome wide association (GWAS) and validated in a backcross population. Conclusions: Tomato steroidal alkaloids are diverse in the red-fruited tomato clade and their biosynthesis is regulated in a coordinated manner.

Neurotoxic alkaloid in pollen and nectar excludes generalist bees from foraging at death-camas, Toxicoscordion paniculatum (Melanthiaceae)

Many plants produce broadly active toxins to which specialist herbivores—typically insects—have evolved counter-adaptations, sometimes spawning co-evolutionary arms races. Many non-social bee species are likewise taxonomic host specialists, but the specialists’ pollen hosts frequently attract diverse floral generalists as well, even to flowers of plants that are otherwise chemically defended. In this study of foothills death-camas, Toxicoscordion paniculatum (Nutt.) Rydberg (formerly Zigadenus), we show that its pollen and nectar both contain zygacine, the steroidal alkaloid responsible for this plant’s notorious mammalian toxicity. Hungry naïve adults of a generalist solitary bee, Osmia lignaria Say (Megachilidae), would briefly drink death-camas nectar or biologically relevant doses of zygacine in syrup, followed by prolonged bouts of irritable tongue grooming; many became paralyzed and some even died. Larvae fed dosed provision masses likewise often ceased feeding and sometimes died. Prolonged irritation and subsequent deterrence of foraging O. lignaria likely illustrates why it and 50+ other vernal bee species were absent from death-camas flowers in a five-state survey. The sole visiting bee, Andrena astragali, foraged exclusively at death-camas flowers for pollen and nectar. Thus, a toxic alkaloid found in death-camas pollen and nectar deters generalist bees from flowers of this pollinator-dependent monocot, restricting visitation to a single specialist bee that tolerates death-camas toxins and is its likely pollinator.

Synthetic approaches towards cortistatins: evolution and progress through its ages

With an exhaustive coverage of all the synthetic approaches towards cortistatins, this review serves to assemble most of the avenues which have been employed to conquer this complex steroidal alkaloid architecture.