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Summary• Since the 1970s it has been known that the nursery pollinator Hadena bicruris is attracted to the flowers of its most important host plant, Silene latifolia , by their scent. Here we identified important compounds for attraction of this noctuid moth.• Gas chromatographic and electroantennographic methods were used to detect compounds eliciting signals in the antennae of the moth. Electrophysiologically active compounds were tested in wind-tunnel bioassays to foraging naïve moths, and the attractivity of these compounds was compared with that to the natural scent of whole S. latifolia flowers.• The antennae of moths detected substances of several classes. Phenylacetaldehyde elicited the strongest signals in the antennae, but lilac aldehydes were the most attractive compounds in wind-tunnel bioassays and attracted 90% of the moths tested, as did the scent of single flowers.• Our results show that the most common and abundant floral scent compounds in S. latifolia , lilac aldehydes, attracted most of the moths tested, indicating a specific adaptation of H. bicruris to its host plant.

Summary• By emitting strong fetid scents, sapromyiophilous flowers mimic brood and food sites of flies to attract them as pollinators. To date, intensive comparative scent analyses have been restricted to sapromyiophilous Araceae. Here, we analysed flower volatiles of fetid stapeliads to improve our understanding of the floral biology of fly pollinated species, and to learn whether mimicry types comparable to those found in Araceae exist.• Floral volatiles of 15 species out of 11 genera within the AsclepiadoideaeCeropegieae-Stapeliinae were collected via headspace adsorption and thermal desorption and analysed by gas chromatography-mass spectometry (GC-MS). Data were analysed using CNESS-NMDS statistics.• Sapromyiophilous stapeliads are highly diverse in their scent composition, in which sulphur compounds, benzenoids, fatty acid derivatives or nitrogen-containing compounds dominate. Four groups are evident: species with high p-cresol content but low amounts of polysulphides (herbivore faeces mimicry); species with mainly polysulphides and low amounts of p-cresol (carnivore/omnivore faeces or carcass mimicry); species with high amounts of heptanal and octanal (carnivore/omnivore faeces or carcass mimicry); and species with hexanoic acid (urine mimicry).• Considering the findings in the unrelated Araceae, our results support the universality of different mimicry types that are obviously subsumed under the sapromyiophilous syndrome.

Coevolution is thought to be a major factor in shaping plant-pollinator interactions. Alternatively, plants may have evolved traits that fitted pre-existing preferences or morphologies in the pollinators. Here, we test these two scenarios in the plant family of

Chemical communication is ubiquitous. The identification of conserved structural elements in visual and acoustic communication is well established, but comparable information on chemical communication displays (CCDs) is lacking. We assessed the phenotypic integration of CCDs in a meta-analysis to characterize patterns of covariation in CCDs and identified functional or biosynthetically constrained modules. Poorly integrated plant CCDs (i.e. low covariation between scent compounds) support the notion that plants often utilize one or few key compounds to repel antagonists or to attract pollinators and enemies of herbivores. Animal CCDs (mostly insect pheromones) were usually more integrated than those of plants (i.e. stronger covariation), suggesting that animals communicate via fixed proportions among compounds. Both plant and animal CCDs were composed of modules, which are groups of strongly covarying compounds. Biosynthetic similarity of compounds revealed biosynthetic constraints in the covariation patterns of plant CCDs. We provide a novel perspective on chemical communication and a basis for future investigations on structural properties of CCDs. This will facilitate identifying modules and biosynthetic constraints that may affect the outcome of selection and thus provide a predictive framework for evolutionary trajectories of CCDs in plants and animals.

Summary1. Bees use floral cues, such as odour, colour, size and shape, to discriminate and recognize flowers. The interplay between visual and olfactory cues in social as well as in solitary bee species is poorly understood. 2. In this study we tested the host finding and recognition behaviour in a specialized (oligolectic) bee species, Hoplitis adunca (Megachilidae), which collects pollen exclusively on flowers of Echium (Boraginaceae) species. We determined the importance of visual (especially floral colour) and olfactory cues of Echium vulgare flowers in host-plant finding and recognition, as well as in the discrimination of non-host plants (Anchusa officinalis), by foraging-naı¨ve and -experienced H. adunca females. 3. Our investigations showed that the interplay between visual and olfactory cues of E. vulgare flowers is essential for host-plant finding and recognition by H. adunca females. The finding suggests that the blue colour of the flowers attracts the bees, while the olfactory cues, which are Echium-specific, are used by the bees to recognize their host plant and discriminate it from non-host plants. 4. Our results show that different modalities of floral cues need to be studied in a combined approach in order to understand the communication in bee-flower interactions and the cues used by bees to find and recognize their host-plants.

Four to six percent of plants, distributed over different angiosperm families, entice pollinators by deception [1]. In these systems, chemical mimicry is often used as an efficient way to exploit the olfactory preferences of animals for the purpose of attracting them as pollinators [2,3]. Here, we report a very specific type of chemical mimicry of a food source. Ceropegia sandersonii (Apocynaceae), a deceptive South African plant with pitfall flowers, mimics attacked honeybees. We identified kleptoparasitic Desmometopa flies (Milichiidae) as the main pollinators of C. sandersonii. These flies are well known to feed on honeybees that are eaten by spiders, which we thus predicted as the model chemically mimicked by the plant. Indeed, we found that the floral scent of C. sandersonii is comparable to volatiles released from honeybees when under simulated attack. Moreover, many of these shared compounds elicited physiological responses in antennae of pollinating Desmometopa flies. A mixture of four compounds-geraniol, 2-heptanone, 2-nonanol, and (E)-2-octen-1-yl acetate-was highly attractive to the flies. We conclude that C. sandersonii is specialized on kleptoparasitic fly pollinators by deploying volatiles linked to the flies' food source, i.e., attacked and/or freshly killed honeybees. The blend of compounds emitted by C. sandersonii is unusual among flowering plants and lures kleptoparasitic flies into the trap flowers. This study describes a new example of how a plant can achieve pollination through chemical mimicry of the food sources of adult carnivorous animals.

Many bees are oligolectic and collect pollen for their larvae only from one particular plant family or genus. Here, we identified flower scent compounds of two Salix species important for the attraction of the oligolectic bee Andrena vaga, which collects pollen only from Salix. Flower scent was collected by using dynamic-headspace methods from Salix caprea and S. atrocinerea, and the samples were subsequently analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) to detect possible attractants of A. vaga. EAD active compounds were identified by gas chromatography coupled to mass spectrometry. Both Salix species had relatively similar scent profiles, and the antennae of male and female bees responded to at least 16 compounds, among them different benzenoids as well as oxygenated monoterpenoids and sesquiterpenoids. The strongest antennal responses were triggered by 1,4-dimethoxybenzene, and in field bioassays, this benzenoid attracted females of A. vaga at the beginning of its flight period, but not at the end.