Floral scent chemistry of mangrove plants

The flowers of mangrove plants are pollinated by a variety of pollinators including birds, bats, and insects. This study analyzed the floral scent chemistry of mangroves on Iriomote Island (located near Taiwan) including Bruguiera gymnorrhiza (L.) Lamk. (Rhizophoraceae), Kandelia candel (L.) Druce (Rhizophoraceae), Rhizophora stylosa Griff. (Rhizophoraceae), Sonneratia alba J. Smith (Sonneratiaceae), Nypa fruticans (Thunb.) Wurmb. (Palmae), Lumnitzera racemosa Willd. (Combretaceae), Avicennia marina (Forsk.) Vierh. (Avicenniaceae or Verbenaceae), and Pemphis acidula Forst. (Lythraceae). A total of 61 chemicals (fatty acid derivatives, terpenoids, carotenoid derivatives, benzenoids, nitrogen-containing compounds, 13 unknown chemicals) were detected in the floral scents of the various species. The species displayed a distinct chemical profile ranging from only two chemicals in the floral scent of Kandelia candel to more than 25 chemicals in the floral scent of Nypa fruticans. All of the identified chemicals have been found in the floral scents of other angiosperms. The chemical profile of some species can be correlated with their floral morphology and pollinators.     

Plant volatiles as method of communication

Plants emit volatile compounds that can act as a communication method to insects, neighboring plants and pathogens. Plants respond to leaf and root damage by herbivores and pathogens by emitting these compounds. The volatile compounds can deter the herbivores or pathogens directly or indirectly by attracting their natural enemies to kill them. The simultaneous damage of plants by herbivores and pathogens can influence plant defense. The induced plant volatiles can also make neighboring plants ready for defense or induce defense in parts distant from the damaged area of the same plant. Belowground root herbivory can alter the defense response to aboveground leaf herbivory. In addition, most plants normally emit volatile compounds from their flowers that directly attract foraging mutualistic insects for nectar, which in turn perform the very important function of pollination for subsequent reproduction. The volatile compounds emitted from the floral and vegetative parts of plants belong to three main classes of compounds: terpenoids, phenylpropanoids/benzenoids, and C6-aldehydes (green-leaf volatiles). The volatile phytohormones methyl salicylate and methyl jasmonate serve as important signaling molecules for communication purposes, and interact with each other to optimize the plant defense response. Here we discuss and integrate the current knowledge on all types of communication between plants and insects, neighboring plants and pathogens that are mediated through plant volatiles.     

虫害诱导挥发物的生态调控功能

虫害诱导挥发物（herbivore-induced plant volatiles, HIPVs）是植物受害虫胁迫后释放的挥发性物质,是植物与周围环境进行信息交流的媒介。环境中的天敌、害虫和植物通过感知HIPVs所携带的信息,对各自的行为或生理生化反应做出相应的调整。介绍了挥发物的种类及主要的生物合成途径,概括了影响天敌依据HIPVs搜寻寄主和猎物的主要因素。综述了这类挥发性物质对植食性昆虫寄主选择或产卵行为的影响,介绍了植物地上部分和地下部分受害后对彼此间接防御的影响,讨论了多种害虫加害同种植物后对天敌搜寻猎物或寄主行为的影响。另外,作为损伤信号,HIPVs还能诱导同株植物未受害部位和邻近植株的防御反应。最后,对HIPVs在害虫防治中的应用现状及前景作了介绍和讨论。     

Floral scent chemistry of mangrove plants

The flowers of mangrove plants are pollinated by a variety of pollinators including birds, bats, and insects. This study analyzed the floral scent chemistry of mangroves on Iriomote Island (located near Taiwan) including Bruguiera gymnorrhiza (L.) Lamk. (Rhizophoraceae), Kandelia candel (L.) Druce (Rhizophoraceae), Rhizophora stylosa Griff. (Rhizophoraceae), Sonneratia alba J. Smith (Sonneratiaceae), Nypa fruticans (Thunb.) Wurmb. (Palmae), Lumnitzera racemosa Willd. (Combretaceae), Avicennia marina (Forsk.) Vierh. (Avicenniaceae or Verbenaceae), and Pemphis acidula Forst. (Lythraceae). A total of 61 chemicals (fatty acid derivatives, terpenoids, carotenoid derivatives, benzenoids, nitrogen-containing compounds, 13 unknown chemicals) were detected in the floral scents of the various species. The species displayed a distinct chemical profile ranging from only two chemicals in the floral scent of Kandelia candel to more than 25 chemicals in the floral scent of Nypa fruticans. All of the identified chemicals have been found in the floral scents of other angiosperms. The chemical profile of some species can be correlated with their floral morphology and pollinators. Received: August 18, 2001 / Accepted: October 9, 2001     

Seasonal and diel variations in scent composition of ephemeral Murraya paniculata (Linn.) Jack flowers are contributed by separate volatile components

Scent profile of the ephemeral nocturnal floral species Murraya paniculata was characterized to assess diel and seasonal variability. The floral fragrance was found to constitute a characteristic set of 15 major volatile organic compounds (VOCs) dominated by benzenoids, terpenoids and phenylethanoids. Strong diel variability was detected due to dominantly endogenous regulation of 2-phenylethanol and (E)-β-ocimene emission levels, along with temperature-correlated emission rates of 2-phenylethanal, methyl benzoate, methyl anthranilate and germacrene D, resulting in high diurnal contents of the former two VOCs and high nocturnal contents of the latter four VOCs in the fragrance. Significant seasonal variation was contributed by a separate suite of VOCs including linalool, nonanal, decanal, methyl salicylate and methyl palmitate. Higher abundances of these components in certain seasons were found to add subtle variations in the strong diurnal/nocturnal division in the scent profile. Emission rate of linalool is endogenously regulated on a seasonal scale, but that of (E,E)-α-farnesene was maintained at consistent proportions even if correlated to temperature variations. It was concluded that the two sub-sets of major scent compounds, each comprising six VOCs, are adaptive responses such that the strong day/night component of variation in maintained along with necessary physiological adjustments to changing seasons. The varying effects of climatic factors on the 15 major VOCs indicated different regulating mechanisms comprising environmental and endogenous mechanisms in different degrees.     

Positioning Bacillus subtilis as terpenoid cell factory

Increasing demands for bioactive compounds have motivated researchers to employ micro-organisms to produce complex natural products. Currently, Bacillus subtilis has been attracting lots of attention to be developed into terpenoids cell factories due to its generally recognized safe status and high isoprene precursor biosynthesis capacity by endogenous methylerythritol phosphate (MEP) pathway. In this review, we describe the up-to-date knowledge of each enzyme in MEP pathway and the subsequent steps of isomerization and condensation of C5 isoprene precursors. In addition, several representative terpene synthases expressed in B. subtilis and the engineering steps to improve corresponding terpenoids production are systematically discussed. Furthermore, the current available genetic tools are mentioned as along with promising strategies to improve terpenoids in B. subtilis, hoping to inspire future directions in metabolic engineering of B. subtilis for further terpenoid cell factory development.     

Emitted and endogenous floral scent compounds of Prunus mume and hybrids

Prunus mume is the only species of Prunus known to produce a strong floral fragrance. Most interspecific hybrids between P. mume and other species of Prunus lack the fragrance. The analysis of variations in emitted and endogenous compounds among genetically close cultivars is a powerful approach for revealing the mechanisms underlying floral scent emission. Compounds emitted by flowers from five cultivars were collected using the static headspace method, and endogenous compounds in the flowers were extracted with ethyl acetate. Samples were analysed quantitatively and qualitatively using gas chromatography-mass spectrometry. The result showed that benzenoids were the dominant compounds, of which benzyl acetate was the principal component contributing to the floral scent of P. mume. A clustering analysis of the floral volatiles from the different cultivars suggested that the scent traits of hybrids are related to the taxonomic relationship between their parents. The correlations between the amount of the endogenous and emitted compounds revealed that benzyl acetate had a stronger tendency to be volatile than the other compounds and the volatilisation rate of volatile compounds varied greatly among different cultivars. The importance of the biosynthetic pathway and the function of benzaldehyde are discussed.     

Volatile Emission in Bracken Fern Is Induced by Jasmonates but Not by Spodoptera littoralis or Strongylogaster multifasciata Herbivory

Jasmonate-mediated regulation of VOC emission has been extensively investigated in higher plants, however, only little is known about VOC production and its regulation in ferns. Here, we investigate whether the emission of VOCs from bracken fern Pteridium aquilinum is triggered by herbivory and if so - whether it is regulated by the octadecanoid signaling pathway. Interestingly, feeding of both generalist (Spodoptera littoralis) and specialist (Strongylogaster multifasciata) herbivores as well as application of singular and continuous mechanical wounding of fronds induced only very low levels of VOC emission. In contrast, treatment with jasmonic acid (JA) led to the emission of a blend of VOCs that was mainly comprised of terpenoids. Likewise, treatment with the JA precursor 12-oxo-phytodienoic acid (OPDA) and α-linolenic acid also induced VOC emission, albeit to a lower intesity than the JA treatment. Accumulation of endogenous JA was low in mechanically wounded fronds and these levels were unaffected by the application of oral secretions from both generalist or specialist herbivores. The emission of terpenoids upon JA treatment could be blocked with fosmidomycin and mevinolin, which are inhibitors of the MEP- and MVA pathways, respectively. These results indicate that similar to higher plants, terpenoid VOCs are produced via these pathways in bracken fern and that these pathways are JA-responsive. However, the very low amounts of terpenoids released after herbivory or mechanical damage are in stark contrast to what is known from higher plants. We speculate that S. multifasciata and S. littoralis feeding apparently did not induce the threshold levels of JA required for activating the MEP and MVA pathways and the subsequent volatile emission in bracken fern.     

Fig volatile compounds--a first comparative study

We analysed the compounds of volatile blends released by receptive figs of twenty Ficus species to attract their specific pollinating wasps. In all, 99 different compounds were identified. The compounds are mainly terpenoids, aliphatic compounds and products from the shikimic acid pathway. In each species blend, there are few major compounds, which are generally common among floral fragrances. Most species blends also include rare compounds, but generally their proportion in the blend is low. A possible basis for species-specificity of Ficus-wasp interactions is discussed in relation to the patterns of volatiles found in this interspecies comparison.     

<Emphasis Type="Italic">In silico</Emphasis> analysis and experimental improvement of taxadiene heterologous biosynthesis in <Emphasis Type="Italic">Escherichia coli</Emphasis>

The biosynthesis of terpenoids in heterologous hosts has become increasingly popular. Isopentenyl diphosphate (IPP) is the central precursor of all isoprenoids, and the synthesis can proceed via two separate pathways in different organisms: The 1-deoxylulose 5-phosphate (DXP) pathway and the mevalonate (MVA) pathway. In this study, an in silico comparison was made between the maximum theoretical IPP yields and the thermodynamic properties of the DXP and MVA pathways using different hosts and carbon sources. We found that Escherichia coli and its DXP pathway have the most potential for IPP production. Consequently, codon usage redesign, and combinations of chromosomal engineering and various strains were considered for optimizing taxadiene biosynthesis through the endogenic DXP pathway. A high production strain yielding 876 ± 60 mg/L taxadiene, with an overall volumetric productivity of 8.9 mg/(L × h), was successfully obtained by combining the chromosomal engineered upstream DXP pathway and the downstream taxadiene biosynthesis pathway. This is the highest yield thus far reported for taxadiene production in a heterologous host. These results indicate that genetic manipulation of the DXP pathway has great potential to be used for production of terpenoids, and that chromosomal engineering is a powerful tool for heterologous biosynthesis of natural products.     

Comparison of floral properties and breeding system in dimorphic Buddleja delavayi (Scrophulariaceae)

In this study, floral color, scent composition and emission rate, nectar property, pollinators, and breeding system of dimorphic Buddleja delavayi Gagnep. were investigated. Flower color of B. delavayi was determined using a standard color chart and spectrophotometer, and two distinct color polymorphisms were observed having purple or white flowers. Floral scents of B. delavayi were collected using dynamic headspace adsorption and identified with coupled gas chromatography and mass spectrometry. In total, 28 compounds were identified from the flowers of B. delavayi. The identified scents were divided into three chemical classes based on their biosynthetic origin: terpenes, fatty acid derivatives, and benzenoids. The scent profiles in all individuals were dominated by a few components, such as lilac aldehyde and alcohol, 4-oxoisophorone, benaldehyde, and oxoisophorone oxide. Floral scent composition (benzenoids and terpenes) showed a significant difference between white and purple flower morphs. Flower color–flower scent associations in B. delavayi were identified with two distinct scent profiles in the two color phenotypes. The studies of other floral characteristics (nectar, floral visitors, breeding system, and fruit set) indicated that floral scent emission rate, nectar volume, visitor visitation frequency, and natural fruit set were not significantly different between the two flower color morphs. Bagging experiments revealed that seed production of B. delavayi is dependent mainly on honeybee Apis cerana. Lastly, this study implies that dimorphic floral color in B. delavayi may have been maintained by floral visitors and nectar guide color.     

RNAi suppression of CYP82D P450 hydroxylase,an enzyme involved in gossypol biosynthesis,enhances resistance to Fusarium wilt in cotton

Cotton plants produce two classes of terpenoid defence compounds against pathogens and other pests. Both classes are derived from a common sesquiterpenoid precursor, δ-cadinen-2-one, which enters either the gossypol pathway or the lacinilene pathway. Blocking the gossypol pathway by RNAi suppression of the early pathway biosynthetic enzyme CYP82D hydroxylase resulted in enhanced resistance to the Fusarium wilt pathogen. Analyses of root terpenoids revealed no overall increases in the products of the gossypol pathway in the roots infected by the wilt pathogen. However, the lacinilene pathway was elicited by the pathogen and the lacinilene levels were 19-fold higher in the RNAi plants than in wild-type plants. In the pathogen inoculated RNAi 73R plants, the concentrations of DHC and HMC were 231 μg and 886 μg/g dry roots, respectively, which may have contributed to the inhibition of fungal invasion. In comparison, the concentrations of DHC and HMC in the pathogen inoculated control wild-type 73W plants were only 0.7 μg and 58 μg/g dry roots, respectively. Fungitoxicity testing showed that DHC at 100 μg/ml inhibited growth of the Fusarium wilt pathogen by >93%. Treatment with the phytohormone jasmonic acid failed to elicit production of lacinilene pathway terpenoids in roots of either RNAi plants or their wild-type sibling lines, but increased production of gossypol pathway terpenoids with concentrations in RNAi plants 80%–97% less than those in wild-type plants. This indicates that induction of the lacinilene pathway is not directly mediated by jasmonic acid signalling and requires other signalling to activate the pathway. These results illustrate possible mechanisms of wilt disease resistance in cotton and provide a new approach to increase host resistance by manipulating these two major cotton chemical defence pathways.