Fragrance volatiles of developing and senescing carnation flowers

Thirteen major volatiles of the carnation flower fragrance signature have been identified by GC/MS. Of these, ten, hexanal, (2E)-hexenal, 1-hexanol, 2-hexanol, 3-hexen-1-ol, nonanal, benzaldehyde, benzyl alcohol, benzyl benzoate and caryophyllene, were quantified. The steady-state levels of these ten volatiles change independently as the flowers develop and senesce, suggesting that their synthesis is developmentally regulated. In addition, the chemical composition of the fragrance signature in naturally senesced flowers proved to be very different from that for flowers that had been induced to senesce prematurely by treatment with ethylene. Thus, senescence-related changes in carnation floral scent appear not to be directly regulated by ethylene. From cellular fractionation studies, it is evident that all of the volatiles, except 2-hexanol, are present in both membranous and cytosolic compartments, suggesting that their synthesis is membrane-associated and that they subsequently partition into the cytosol in accordance with partition coefficients.     

柚花头香化学成分的研究(一)

本文首次报道柚花的香气成分。作者利用憎水性树脂XAD-4吸附柚鲜花的头香,并以毛细管气相色谱和毛细管气相色谱-质谱-计算机联用方法研究头香的化学组分,分离鉴定了17个已知化学成分。它们是芳樟醇、β-蒎烯、β-水芹烯、橙花叔醇等。     

云南含笑鲜花头香的化学成分初步研究

云南含笑鲜花的香气,用一般提取方法所得的精油或浸膏的香气与其鲜花自然散发的香气差异较大;我们利用一种新的方法——树脂吸附法,把云南含笑花从初开至凋谢整个过程所释放的香气吸附于一种憎水性树脂表面,然后通过洗脱、浓缩所得到的精油。其香气与鲜花花香气较为相似。通过GC.GC/MS/DS分析。共鉴定出29个已知化合物。     

Flower color change accelerated by bee pollination in Tibouchina (Melastomataceae)

Floral color changes are common among Melastomataceae and have been interpreted as a warning mechanism for bees to avoid old flowers, albeit increasing long-distance flower display. Here the reproductive systems of Tibouchina pulchra and T. sellowiana were investigated by controlled pollinations. Their pollinators were identified, and experiments on floral color and fragrance changes were conduced to verify if those changes affect the floral visitation. Both Tibouchina species are self compatible. The flowers lasted three days or more, and the floral color changed from white in the 1st day to pink in the following days. Pollen deposition on stigma induced floral color change. The effectiveness of the pollination is dependent on bees’ size; only large bees were regarded as effective pollinators. In experimental tests, the bees in T. pulchra preferred the natural white flowers while the visitors of T. sellowiana were attracted by both natural and mimetic 1st-day flowers (2nd-day flowers with experimentally attached 1st-day flower petals). During the experiments on floral fragrance, the bees visited both natural and mimetic 1st-day flowers (2nd-day flowers with 1st-day flower scents). In both experiments, the bees avoided natural 2nd-day flowers, but seldom visited modified 2nd-day flowers. The attractiveness of T. pulchra and T. sellowiana flowers cannot be attributed exclusively to the color or the fragrance separately, both factors seemingly act together.     

Leaf herbivory increases floral fragrance in male but not female Cucurbita pepo subsp. texana (Cucurbitaceae) flowers

Mutualisms are key interactions that affect population dynamics and structure communities, but the extent to which mutualists can attract potential partners may depend on community context. Many studies have shown that leaf herbivory reduces pollinator visitation and have focused on reduced floral visual display and rewards as potential mechanisms. However, olfactory display plays a critical role in mediating interactions between plants, herbivores, and pollinators. We simulated leaf damage in Cucurbita pepo subsp. texana and measured fragrance emission and other floral characters of both male and female flowers. Contrary to our expectations, damage increased fragrance production, but only in male flowers. Female flowers, which were bigger and produced more fragrance than males, were unaffected by leaf damage. The greatest increase in floral fragrance compounds was in the terpenoids, which we hypothesize could be byproducts of defensively induced cucurbitacins, or they may function defensively themselves. In summary, this study is the first to demonstrate changes in floral fragrance due to leaf damage. Such changes in floral fragrance following herbivory may be a critical and overlooked mechanism mediating interactions between plants, herbivores, and pollinators.     

Floral characteristics affect susceptibility of hybrid tea roses, Rosa x hybrida, to Japanese beetles (Coleoptera: Scarabaeidae)

The Japanese beetle, Popillia japonica Newman, feeds on the flowers and foliage of roses. Rosa x hybrida. Beetles attracted to roses land almost exclusively on the flowers. This study evaluated characteristics of rose flowers including color, size, petal count and fragrance, as well as height of plants and blooms within plant as factors in attractiveness to Japanese beetles. Artificial flowers that had been painted to match the spectral reflectance of real blooms were attached to potted nonflowering rose plants in the field and the number of beetles that landed on each model was recorded. More beetles landed on the yellow- and white-colored flower models than on the five other bloom colors that were tested. Large (15 cm diameter) yellow flower models attracted more beetles than did smaller (8 cm diameter) yellow models. There was no difference in beetle response to yellow flower models of the same size that differed in bloom complexity (i.e., number of petals). Experiments in which blooming rose plants were elevated above controls, or in which flower models were placed at different heights within plant canopies, failed to support the hypothesis that height per se accounts for beetles' attraction to flowers over leaves. Attractiveness of selected rose cultivars that varied in fragrance and flower color also was evaluated in the field. Yellow-flowered cultivars were more susceptible than those with red flowers, regardless of fragrance intensity as rated by breeders. Growing cultivars of roses that have relatively dark and small-sized blooms may have some benefit in reducing Japanese beetles' attraction to roses.     

Specialized pollination by spider-hunting wasps in the African orchid Disa sankeyi

Disa sankeyi Rolfe was found to be pollinated almost exclusively by Hemipepsis wasps (Pompilidae) at sites across its range in the Drakensberg mountains of South Africa. Wasps of both sexes appear to locate the cryptic yellow-green flowers primarily by using scent cues, as they show a classic zigzag flight pattern when approaching inflorescences. The sweet-spicy fragrance emitted by the flowers is strong enough to be discernable by a human from several metres away and consists of a blend of at least 65 volatile compounds, with (E)- cinnamic aldehyde and eugenol as the major constituents. On settling, wasps lick the exposed droplet of nectar that is secreted from the mouth of the reduced floral spur on each flower. Pollinaria become attached to the front feet of the wasps as they grasp flowers adjacent to those on which they are feeding. Pollen transfer to stigmas similarly takes place on flowers adjacent to those that are used as a nectar source. Almost 100% of flowers in the study populations were found to have been pollinated. Specialized pollination by pompilid wasps appears to be a rare phenomenon that has been reported only in southern African plant species. It appears to be associated with cryptic green-yellow flowers and highly accessible nectar. Behavioural assays are required to determine whether the basis of the specialization in this pollination system lies in a particular chemical composition of the floral fragrance.     

Spatial fragrance patterns in flowers of Silene latifolia: Lilac compounds as olfactory nectar guides?

Floral odour can differ qualitatively and quantitatively between different parts of the flowers, and these spatial fragrance patterns within the flowers can be used by pollinators for orientation on flowers. Here we present results of spatial fragrance patterns within flowers of the dioecious Silene latifolia (Caryophyllaceae). Volatiles were collected and analysed using a highly sensitive dynamic headspace method, which allows dramatically reducing the sample time. From all flower parts, especially the petals and the anthophore emitted the typical flower volatiles of S. latifolia. However, compounds emitted from the petals differed from compounds emitted by the anthophore. The anthophore emitted the monoterpenoids lilac aldehydes and alcohols, whereas, all other typical scent compounds (e.g. benzoids, other monoterpenoids) were emitted by the petals. Lilac aldehydes are known to be behaviourally very attractive for noctuid moths, and they may serve as nectar guides in S. latifolia.     

Olfactory versus visual cues in a floral mimicry system

 We used arrays of artificial flowers with and without fragrance to determine the importance of olfactory and visual cues in attracting insects to a floral mimic. The mimic is a fungus, Puccinia monoica Arth., which causes its crucifer hosts (here, Arabis drummondii Gray) to form pseudoflowers that mimic co-occurring flowers such as the buttercup, Ranunculus inamoenus Greene. Although pseudoflowers are visually similar to buttercups, their sweet fragrance is distinct. To determine whether visitors to pseudoflowers were responding to fragrance we performed an experiment in which we removed the visual cues, but allowed fragrance to still be perceived. In this experiment we found that pseudoflower fragrance can attract visitors by itself. In other experiments we found that the relative importance of olfactory and visual cues depended on the species of visitor. Halictid bees (Dialictus sp.) had a somewhat greater visual than olfactory response, whereas flies (muscids and anthomyiids) were more dependent on olfactory cues. We also used bioassays to determine which of the many compounds present in the natural fragrance were responsible for attraction. We found that halictid bees were equally attracted to pseudoflowers and to a blend containing phenylacetaldehyde, 2-phenylethanol, benzaldehyde and methylbenzoate in the same relative concentrations as in pseudoflowers. Flies, on the other hand, only responded to pseudoflower scent, indicating that we have not yet identified the compound(s) present in pseudoflowers that are attracting them. The ability of insects to differentiate pseudoflowers from true flowers by their fragrance may be important in the evolution of the mimicry system. Different fragrances may facilitate proper transfer of both fungal spermatia and pollen, and thus make it possible for the visual mimicry to evolve. Received: 3 January 1996 / Accepted: 13 August 1996     

Chemical components of male and female flowers of Schisandra chinensis

Schisandra chinensis (Turcz.) Baill. is one of the important traditional medicinal plants in East Asia. It is a dioecious plant with aromatic flowers. The female and male flowers of S. chinensis possess slightly different fragrance characteristics. The overall scent of S. chinensis flowers is quite similar to that of Syringa dilatata (Korean lilac) flowers. Hence, this study aimed to understand the aromatic profile of the hexane extract from female and male flowers of S. chinensis and to compare their profile with the hexane extract of Korean lilac flowers. The chemical composition of hexane extract was determined by gas chromatography and mass spectrometry (GC-MS) analysis. In total, 67 different components were detected in the hexane extract of female (48) and male flowers (51) of S. chinensis; 32 of which were common to both female and male flowers. In regards to gender difference, 16 components were found only in female flowers, and 19 components were found only in male flowers. The results revealed that the most abundant components in the hexane extract of both female and male flowers were lilac alcohol C (9.53 and 7.00%), lilac alcohol A (6.55 and 5.71%), n-hexadecanoic acid (6.21 and 6.96%), linoleic acid (5.14 and 7.61%), β-elemene (5.12 and 1.99), and lilac aldehyde D (4.13 and 4.97%). The data suggest that the major compounds in the hexane extract of S. chinensis flowers were generally similar, but they varied quantitatively according to gender. The presence of 10 components in both S. chinensis and Korean lilac flowers may be responsible for their similar fragrance characteristics. It could be concluded that the different fragrance characteristics of these flowers may be due to the presence of several gender-specific aromatic compounds in minor percentages.     

'Floral' scent production by Puccinia rust fungi that mimic flowers

Crucifers (Brassicaceae) in 11 genera are often infected by rust fungi in the Puccinia monoica complex. Infection causes a 'pseudoflower' to form that is important for attracting insect visitors that sexually outcross the fungus. 'Pollinator' attraction is accomplished through visual floral mimicry, the presence of a nectar reward and floral fragrances. Here we used gas chromatography and mass spectrometry to identify and quantify fragrance production by these rust fungi on several Arabis hosts, and by co-occurring true flowers that share insect visitors. Fungal pseudoflowers produced distinctive floral fragrances composed primarily of aromatic alcohols, aldehydes and esters. Pseudoflower fragrances were chemically similar to noctuid-moth-pollinated flowers, such as Cestrum nocturnum and Abelia grandiflora , but were very different from host flowers, host vegetation and the flowers of coblooming, nonhost angiosperms. There was variation in the quantity and composition of fragrance profiles from different fungal species as well as within and among hosts. The evolution of scent chemistry is relatively conservative in these fungi and can be most parsimoniously explained in three steps by combining chemical data with a previously determined rDNA ITS sequence-based phylogeny. Pseudoflower scent does not appear to represent a simple modification of host floral or vegetative emissions, nor does it mimic the scent of coblooming flowers. Instead, we suspect that the unique fragrances, beyond their function as pollinator attractants, may be important in reducing gamete loss by reinforcing constancy among foraging insects.     

Further observations on rhythmic emission of fragrance in flowers

Observations regarding floral fragrance and the rhythmicity of its emission in four plant species are reported. In the case of flowers of Hoya carnosa R. Br. which are characterized by circadian rhythmicity of scentedness (R. Altenburger and P. Matile, 1988, Planta 174, 248–252), temperature compensation of the free-running period as well as persistence of oscillations in permanent darkness have been demonstrated. A hitherto unidentified component of fragrance turned out to be identical to an unusual sesquiterpene recently discovered in cardamom oil (B. Maurer et al., 1986, Tetrahedron Lett. 27, 2111–2112). In Stephanotis floribunda Brongs. the rhythmic emission of fragrance is circadian in nature, but in a constant environment the oscillations of individual components are increasingly asynchronous. In excised flowers of Odontoglossum constrictum Lindl. the diurnal oscillations observed in a natural photoperiod are abolished under constant environmental conditions. They are resumed upon the return to a 1212-h photoperiod. The absence of circadian control could also be demonstrated in excised flowers of Citrus medica L. In this species, too, the daily maxima of scent emission reappear upon the transfer of flowers to a 1212-h light/ dark cycle. Results obtained upon the comparative analysis of volatiles in the headspace above the flowers and in petal extract indicate that the relative abundance of an individual compound in the floral fragrance is not a function of differential volatility.Abbreviations DL 1212 h photoperiod - DD continuous darkness - GLC gas-liquid chromatography - LL continuous illumination The authors are indebted to R. Kaiser, Givaudon Corp.for kindly carrying out the identifikation of volatiles by gas-liquid chromalography/mass spectrometry.     

Solid-phase microextraction of volatile compounds from flowers of two Brunfelsia species

Two plant species belonging to the genus Brunfelsia, commonly known as “Yesterday-Today-and-Tomorrow”, are closely related, however, differ by their flower fragrance. Flowers of Brunfelsia australis present a pleasant fragrance, whereas flowers of Brunfelsia pauciflora are scentless. SPME/GC/MS analysis on flower samples of both species of Brunfelsia indicated that flowers of B. australis emitted a fresh flowery fragrance, essentially comprising two monoterpenic compounds (linalool and (E)-ocimene). B. pauciflora, on the other hand, produced only a few sesquiterpenoids. These results are considered in an ecological and evolutionary context.     

Linalool and linalool oxide production in transgenic carnation flowers expressing the Clarkia breweri linalool synthase gene

Most modern cut-flower cultivars, including those of carnation(Dianthus caryophyllus), lack distinct fragrance.Carnationcv. Eilat flowers produce and emit various fragrance compounds, includingbenzoic acid derivatives and sesquiterpenes, but not monoterpenes. Based onGC-MS analysis, benzoic acid, benzyl benzoate, phenylethyl benzoate, methylbenzoate, cis-3-hexenyl benzoate and -caryophylleneare the major fragrance compounds, representing ca. 60% of the total volatilesgenerated by these flowers. The level of these compounds increases dramaticallyduring petal development. To evaluate the possibility of producing monoterpenesin carnation cv. Eilat, we generated transgenic plants expressing the linaloolsynthase gene from Clarkia breweri under the regulation ofthe CaMV 35S constitutive promoter. The product of this gene catalyzes theproduction of the monoterpene linalool from geranyl diphosphate. HeadspaceGC-MSanalysis revealed that leaves and flowers of transgenic, but not controlplants,emit linalool and its derivatives, cis- andtrans-linalool oxide. GC-MS analysis of petal extractrevealed the accumulation of trans-linalool oxide but notlinalool. The emission of linalool by the transgenic flowers did not lead todetectable changes in flower scent for human olfaction.     

Biosynthesis of α- and β-ionone, prominent scent compounds, in flowers of Osmanthus fragrans

Carotenoid derived volatiles are important fragrance compounds, which contribute to the scents of flowers from diverse taxa. A famous example is represented by the flowers of Osmanthus fragrans where apocarotenoids account for more than 20% of all volatiles. In the recent years, bio-degradation of carotenoids has been shown to be an important route for apocarotenoids formation. Here, we report on the contribution the O. fragrans carotenoid cleavage dioxygenase 1 to the synthesis of the two predominant C(13)-apocarotenoids, α- and β-ionone, derived from α-and β-carotene, respectively.     

Fragrance analyses,an aid to taxonomic relationships of the genusCoryanthes (Orchidaceae)

All members of the investigated genusCoryanthes (subtribeStanhopeinae) are pollinated by male euglossine bees. The different fragrance profiles are the primary reproductive isolating mechanisms, because the flowers are interfertile. The fragrance patterns of 17 species ofCoryanthes were analyzed by gas chromatography as a means to improve the classification of this genus. A first amine (2-N-methylaminobenzaldehyde) was found to be the main fragrance compound of an as yet unclassifiedCoryanthes species.     

腐生植物无叶美冠兰食源性欺骗传粉研究

无叶美冠兰是一种典型的腐生兰科植物,为揭示该物种的自然传粉机制,拓展对兰科植物生殖特性的认识,在广西雅长兰科植物国家级自然保护区对其开展了传粉生态学观测研究。结果表明:无叶美冠兰花朵具备高度自交亲和能力,但不存在自动自花授粉机制,必须依赖外部传粉媒介把花粉送到柱头,实现有效传粉;绿彩带蜂是无叶美冠兰唯一有效传粉昆虫;传粉昆虫与花朵在与传粉功能相关的关键性状在形态上良好拟合;绿彩带蜂的访花活动主要发生在3个阶段:8.6%发生在9:00~11:30,80.2%发生在11:30~14:00,11.2%发生在14:00~15:30;花朵在中午强烈的阳光直射下挥发出香甜的气味。无叶美冠兰花朵主要通过挥发极具诱惑力的香甜气味和唇瓣上黄色的蜜导来诱导绿彩带蜂进入花朵中觅食,传粉昆虫与花朵在与传粉功能相关的关键性状在形态上良好拟合促成有效传粉,绿彩带蜂在整个传粉过程没有获得报酬,是食源性欺骗传粉机制。     

Flowers as sensory billboards: progress towards an integrated understanding of floral advertisement

This paper explores the landscape of integrated sensory signals that are produced by flowers, and the contextual information that modulates pollinator responses to such signals. Chiloglottis orchids are pollinated by mimicking the pheromone and posture of female thynnine wasps, but floral height provides the context within which male wasps respond to these signals. The odor and appearance of carrion attract blowflies to Helicodiceros inflorescences, but flies are more likely to enter the floral chamber when heat is present as a contextual cue. Finally, fragrance, UV-visual cues and echo fingerprints are redundant signals that Glossophaga bats can use to find flowers, depending on prior experience and the photic environment.     

Circadian rhythmicity of fragrance emission in flowers of Hoya carnosa R. Br.

In flowers of Hoya carnosa R. Br. the nocturnal emission of fragrance occurs according to an endogenous circadian rhythmicity. This was demonstrated by the continuation of rhythmical emission for two to three cycles under conditions of permanent illumination. The free-running period was approx. 29 h under these conditions. The inversion of light/dark cycles caused the entrainment of the next peak of emission by approx. 12 h whether the inversion was started with a light period or a with dark period prolonged for 12 h. When only the flower used for fragrance analysis was subjected to an inverted photoperiod, the rest of the plant remaining under the original light/dark cycle, the synchronization of fragrance emission occurred according to the Zeitgeber perceived by the individual flower.