Major Flower Pigments Originate Different Colour Signals to Pollinators

Flower colour is mainly due to the presence and type of pigments. Pollinator preferences impose selection on flower colour that ultimately acts on flower pigments. Knowing how pollinators perceive flowers with different pigments becomes crucial for a comprehensive understanding of plant-pollinator communication and flower colour evolution. Based on colour space models, we studied whether main groups of pollinators, specifically hymenopterans, dipterans, lepidopterans and birds, differentially perceive flower colours generated by major pigment groups. We obtain reflectance data and conspicuousness to pollinators of flowers containing one of the pigment groups more frequent in flowers: chlorophylls, carotenoids and flavonoids. Flavonoids were subsequently classified in UV-absorbing flavonoids, aurones-chalcones and the anthocyanins cyanidin, pelargonidin, delphinidin, and malvidin derivatives. We found that flower colour loci of chlorophylls, carotenoids, UV-absorbing flavonoids, aurones-chalcones, and anthocyanins occupied different regions of the colour space models of these pollinators. The four groups of anthocyanins produced a unique cluster of colour loci. Interestingly, differences in colour conspicuousness among the pigment groups were almost similar in the bee, fly, butterfly, and bird visual space models. Aurones-chalcones showed the highest chromatic contrast values, carotenoids displayed intermediate values, and chlorophylls, UV-absorbing flavonoids and anthocyanins presented the lowest values. In the visual model of bees, flowers with UV-absorbing flavonoids (i.e., white flowers) generated the highest achromatic contrasts. Ours findings suggest that in spite of the almost omnipresence of floral anthocyanins in angiosperms, carotenoids and aurones-chalcones generates higher colour conspicuousness for main functional groups of pollinators.

An Integrated—Omics/Chemistry Approach Unravels Enzymatic and Spontaneous Steps to Form Flavoalkaloidal Nudicaulin Pigments in Flowers of Papaver nudicaule L.

Flower colour is an important trait for plants to attract pollinators and ensure their reproductive success. Among yellow flower pigments, the nudicaulins in Papaver nudicaule L. (Iceland poppy) are unique due to their rarity and unparalleled flavoalkaloid structure. Nudicaulins are derived from pelargonidin glycoside and indole, products of the flavonoid and indole/tryptophan biosynthetic pathway, respectively. To gain insight into the molecular and chemical basis of nudicaulin biosynthesis, we combined transcriptome, differential gel electrophoresis (DIGE)-based proteome, and ultra-performance liquid chromatography–high resolution mass spectrometry (UPLC-HRMS)-based metabolome data of P. nudicaule petals with chemical investigations. We identified candidate genes and proteins for all biosynthetic steps as well as some key metabolites across five stages of petal development. Candidate genes of amino acid biosynthesis showed a relatively stable expression throughout petal development, whereas most candidate genes of flavonoid biosynthesis showed increasing expression during development followed by downregulation in the final stage. Notably, gene candidates of indole-3-glycerol-phosphate lyase (IGL), sharing characteristic sequence motifs with known plant IGL genes, were co-expressed with flavonoid biosynthesis genes, and are probably providing free indole. The fusion of indole with pelargonidin glycosides was retraced synthetically and promoted by high precursor concentrations, an excess of indole, and a specific glycosylation pattern of pelargonidin. Thus, nudicaulin biosynthesis combines the enzymatic steps of two different pathways with a spontaneous fusion of indole and pelargonidin glycoside under precisely tuned reaction conditions.

Colourful cones: how did flower colour first evolve?

Angiosperms that are biotically pollinated typically produce flowers with bright and contrasting colours that help to attract pollinators and hence contribute to the reproductive success of the species. This colourful array contrasts with the much less multicoloured reproductive structures of the four living gymnosperm lineages, which are mostly wind pollinated, though cycads and Gnetales are predominantly pollinated by insects that feed on surface fluids from the pollination drops. This review examines the possible evolutionary pathways and cryptic clues for flower colour in both living and fossil seed plants. It investigates how the ancestral flowering plants could have overcome the inevitable trade-off that exists between attracting pollinators and minimizing herbivory, and explores the possible evolutionary and biological inferences from the colours that occur in some living gymnosperms. The red colours present in the seed-cone bracts of some living conifers result from accumulation of anthocyanin pigments; their likely primary function is to help protect the growing plant tissues under particular environmental conditions. Thus, the visual cue provided by colour in flower petals could have first evolved as a secondary effect, probably post-dating the evolution of bee colour vision but occurring before the subsequent functional accumulation of a range of different flower pigments.

Formation of Nudicaulins In Vivo and In Vitro and the Biomimetic Synthesis and Bioactivity of O-Methylated Nudicaulin Derivatives

Nudicaulins are yellow flower pigments accounting for the color of the petals of Papaver nudicaule (Papaveraceae). These glucosidic compounds belong to the small group of indole/flavonoid hybrid alkaloids. Here we describe in vivo and in vitro experiments which substantiate the strongly pH-dependent conversion of pelargonidin glucosides to nudicaulins as the final biosynthetic step of these alkaloids. Furthermore, we report the first synthesis of nudicaulin aglycon derivatives, starting with quercetin and ending up at the biomimetic fusion of a permethylated anthocyanidin with indole. A small library of nudicaulin derivatives with differently substituted indole units was prepared, and the antimicrobial, antiproliferative and cell toxicity data of the new compounds were determined. The synthetic procedure is considered suitable for preparing nudicaulin derivatives which are structurally modified in the indole and/or the polyphenolic part of the molecule and may have optimized pharmacological activities.