Dissimilar numerical responses of macroinvertebrates to disturbance from drying and predatory sunfish

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A Comparison of Foraging Behavior in Two “Percher” Dragonflies, Pachydiplax longipennis and Erythemis simplicicollis (Odonata: Libellulidae)

Feeding behaviors of two adult libellulid percher dragonflies, Pachydiplax longipennis and Erythemis simplicicollis, were compared. All results pertain to feeding from natural perches located some distance away from reproductive rendezvous sites. Compared to P. longipennis, E. simplicicollis chose broader and less structurally discrete perches, moved more frequently and over a larger area, and took, on average, much larger prey, although diet overlapped broadly in the two species. Erythemis made more frequent feeding flights but with a much lower success rate than Pachydiplax; consequently the prey capture rate was similar in the two species. Gut contents of mature, but not of immature, E. simplicicollis comprised a significantly greater proportion of body mass than in P. longipennis, apparently confirming the importance of larger prey in the diet of the former.     

Prey pursuit and interception in dragonflies

Perching dragonflies (Libellulidae; Odonata) are sit-and-wait predators, which take off and pursue small flying insects. To investigate their prey pursuit strategy, we videotaped 36 prey-capture flights of male dragonflies, Erythemis simplicicollis and Leucorrhinia intacta, for frame-by-frame analysis. We found that dragonflies fly directly toward the point of prey interception by steering to minimize the movement of the prey's image on the retina. This behavior could be guided by target-selective descending interneurons which show directionally selective visual responses to small-object movement. We investigated how dragonflies discriminate distance of potential prey. We found a peak in angular velocity of the prey shortly before take-off which might cue the dragonfly to nearby flying targets. Parallax information from head movements was not required for successful prey pursuit. Accepted: 11 November 1999     

Adipokinetic hormones provide inference for the phylogeny of odonata

Adipokinetic neuropeptides from the corpora cardiaca of 17 species of Odonata encompassing mainly the families Corduliidae and Libellulidae were isolated and structurally elucidated using liquid chromatography coupled with ion trap electrospray ionization mass spectrometry. It became evident that all species of the family Corduliidae studied express the peptide code-named Libau-AKH (pGlu-Val-Asn-Phe-Thr-Pro-Ser-Trp amide), which is also present in all but one libellulid species, Erythemis simplicicollis which expresses Erysi-AKH (pGlu-Leu-Asn-Phe-Thr-Pro-Ser-Trp amide). This divergence from all other Libellulids is due to a nonsynonymous missense single nucleotide polymorphism (SNP) in the nucleotide coding sequence (CDS) of prepro-AKH CDS and supports the polyphyletic nature of Sympetrinae and other subfamilies of libellulids. Despite this exception, these findings then support the hypothesis that Corduliidae and Libellulidae are closely related as stated in most phylogenies. The presence of Anaim-AKH (pGlu-Val-Asn-Phe-Ser-Pro-Ser-Trp amide) in Macromiidae likely distinguishes species in this family from Corduliidae. Current molecular genetic phylogenies and our AKH findings suggest that Syncordulia gracilis, which expresses Anaim-AKH, does not belong in Corduliidae. Evolution of AKHs in anisopteran Odonata are likely due to nucleotide substitution involving nonsynonymous missense SNPs in the CDS of prepro-AKH.     

Identification of the adipokinetic hormone of the large milkweed bug Oncopeltus fasciatus

Abstract The adipokinetic hormone (AKH) of the large milkweed bug Oncopeltus fasciatus is isolated from an acidified methanolic extract of 200 corpora cardiaca, purified by single step reversed phase high‐performance liquid chromatography (HPLC) and N‐terminally deblocked using pyroglutamate aminopeptidase. The sequence is identified by Edman degradation and matrix assisted laser desorption/ionization‐time of flight mass spectroscopy as pGlu‐Leu‐Asn‐Phe‐Ser‐Pro‐Asn‐Trp amide. This structure is confirmed by chemical synthesis and coelution of native and synthetic peptide on HPLC. The AKH of O. fasciatus is identical to Tenmo‐HrTH, a member of the adipokinetic/red pigment‐concentrating hormone peptide family that had been isolated earlier from several tenebrionid beetles. Tenmo‐HrTH causes a significant rise in the concentration of haemolymph lipids when injected into adult male and female O. fasciatus, but displays no hyperglycaemic activity. There is no indication of the presence of other AKHs in O. fasciatus. The large milkweed bug represents the first member of the seed bugs (Lygaeidae) for which the endogenous AKH has been identified.     

Factors influencing age related dispersal of the nymphal OdonatesIschnura barberi (Currie),Pachydiplax longipennis (Burm.) andErythemis simplicicollis (Say)

Size related spatial patterns were observed in naiads of the three dominant odonate taxa in a man-made marsh. These patterns were correlated with various physical and chemical parameters, the vegetation gradient, and prey availability using linear and curvilinear regressions.Ischnura barberi andPachydiplax longipennis naiads increased linearly in head capsule widths from the marsh center to the marsh edge. Increasing naiad size correlated with changes in vegetation. Additionally, the spatial patterning ofPachydiplax longipennis was correlated with decreasing submerged plant surface area as naiad size increased. The head capsule width ofErythemis simplicicollis increased from the marsh center to the marsh edge and then continued to increase towards the marsh center. This complex dispersal pattern did not correlate with any of the measured physical or chemical parameters or the vegetation gradient. However, the dispersal pattern ofErythemis simplicicollis correlated with increased in consumable prey densities along the migratory path. No correlation existed between consumable prey and the dispersal pattern ofIschnura barberi orPachydiplax longipennis.     

Eye movements and target fixation during dragonfly prey-interception flights

The capture of flying insects by foraging dragonflies is a highly accurate, visually guided behavior. Rather than simply aiming at the prey’s position, the dragonfly aims at a point in front of the prey, so that the prey is intercepted with a relatively straight flight trajectory. To better understand the neural mechanisms underlying this behavior, we used high-speed video to quantify the head and body orientation of dragonflies (female Erythemis simplicicollis flying in an outdoor flight cage) relative to an artificial prey object before and during pursuit. The results of our frame-by-frame analysis showed that during prey pursuit, the dragonfly adjusts its head orientation to maintain the image of the prey centered on the “crosshairs” formed by the visual midline and the dorsal fovea, a high acuity streak that crosses midline at right angles about 60° above the horizon. The visual response latencies to drifting of the prey image are remarkably short, ca. 25 ms for the head and 30 ms for the wing responses. Our results imply that the control of the prey-interception flight must include a neural pathway that takes head position into account.     

The adipokinetic hormones of African water bugs of the Heteropteran families Nepidae and Belostomatidae

Four African species of true water bugs (Nepomorpha: Hemiptera: Heteroptera) are studied by mass spectrometry and biological assays to gain information on the presence, structure and function of peptides from the adipokinetic hormone (AKH) family, which are produced in the corpora cardiaca (CC). The water scorpion Laccotrephes fabricii Stål (Nepidae) has the peptide code‐named Peram‐CAH‐I with the sequence pGlu‐Val‐Asn‐Phe‐Ser‐Pro‐Asn‐Trp amide, whereas Appasus grassei Poisson (Belostomatidae) produces Anaim‐AKH, which is a Ser⁷ analogue of Peram‐CAH‐I (pGlu‐Val‐Asn‐Phe‐Ser‐Pro‐Ser‐Trp amide). The giant water bug Hydrocyrius columbiae Spinola (Belostomatidae) has two adipokinetic hormone family members: Anaim‐AKH and Letin‐AKH, which again differ only at position 7 (Ser⁷ versus Tyr⁷). When the sequence data are compared with current molecular phylogenetic analyses of Nepomorpha, they are essentially in agreement with the newest ideas on phylogenetic relationships among the families. Functional investigation of these peptides reveals a mainly lipid‐based energy metabolism in these insects, as demonstrated by a hyperlipaemic response after injecting crude CC extract or the appropriate peptide into the respective species. The carbohydrate concentration in the haemolymph is not affected by such injections, and the carbohydrate level in most cases is lower than that of the circulating lipids. During physical exercise, such as swimming for 1 h, carbohydrates may contribute to some extent to the provision of energy; the substantial increase in the concentration of lipids in the haemolymph, however, is a strong indicator that the peptides are released from the CC and act primarily as true adipokinetic hormones during this period of intense muscular activity.     

Structure and function of adipokinetic hormones of the large white butterfly Pieris brassicae

The large white butterfly Pieris brassicae L. (also called cabbage white) is very common in Europe, Asia and the northern region of Africa, and has also been found in South Africa during approximately the last 20 years. The species is considered a pest insect, with larvae attacking brassicaceous crops. The adult is a strong migratory flyer and new territory can be infested this way. As a first step to investigate methods for combating this pest species, the present study aims to determine the complement of adipokinetic peptides, here generically referred to as adipokinetic hormones (AKHs), which are required to regulate the mobilization of fuels for insect flight. Biological assays, as well as mass spectrometry, reveal information about the presence, structure and function of AKHs in P. brassicae: a methanolic extract of the corpora cardiaca has hypertrehalosaemic activity in cockroaches, does not cause hyperlipaemia in locusts, and has adipokinetic activity in P. brassicae itself. Liquid‐chromatography electrospray ion trap mass spectrometry reveals three peptides that can be associated with the AKH family: the non‐amidated undecapeptide Vanca‐AKH (pELTFTSSWGGK‐OH), the nonapeptide Manse‐AKH (pELTFTSSWG amide) and the novel octapeptide Piebr‐AKH (pELTFSSGW amide). Sequence confirmation of all three assigned structures is obtained from matching mass spectrometry spectra from synthetic and native peptides. Moreover, the synthetic peptides Manse‐AKH and Piebr‐AKH have significant hyperlipaemic (=adipokinetic) activity when injected into newly‐emerged adult cabbage white butterflies. The non‐amidated Vanca‐AKH is, apparently, incompletely processed Manse‐AKH without hormonal activity. Simulated dispersal flight is able to release AKHs, as indicated by the higher concentration of lipids in the haemolymph of adult P. brassicae after activity and rest periods.     

Identification of a hypertrehalosemic factor in Spodoptera exigua

Trehalose is a major blood sugar in insects with a range of physiological functions, including an energy source and a cryoprotectant. Hemolymph trehalose concentrations are tightly regulated according to physiological conditions. An insulin‐like peptide, SeILP1, downregulates hemolymph trehalose concentrations in Spodoptera exigua. Here, we identified a factor that upregulates hemolymph trehalose concentration in S. exigua. Hemolymph trehalose concentrations were significantly increased after immune challenge or under starvation in a time‐dependent manner. To determine endocrine factors responsible for the upregulation, stress‐associated mediators, such as octopamine, serotonin, or eicosanoids were injected, but they did not upregulate hemolymph trehalose. On the other hand, injection with Schistocerca gregaria adipokinetic hormone (AKH) significantly increased hemolymph trehalose concentration in S. exigua. During upregulation of hemolymph trehalose by AKH injection, trehalose degradation appeared to be inhibited because expression of trehalase and SeILP1 were significantly suppressed while that of trehalose phosphate synthase was not significantly changed. Interrogation of a Spodoptera genome database identified an S. exigua AKH‐like gene and its expression was confirmed. During starvation, its expression concentrations were increased, although RNA interference specific to the AKH‐like hypertrehalosemic factor (SeHTF) gene significantly prevented the upregulation of hemolymph trehalose concentrations during starvation. A synthetic peptide of SeHTF was prepared and injected into S. exigua larvae. At nanomolar concentration, the synthetic SeHTF peptide effectively upregulated hemolymph trehalose concentrations. Here we report a novel hypertrehalosemic factor in S. exigua (SeHTF).     

The putative ancestral peptide of the adipokinetic/red-pigment-concentrating hormone family isolated and sequenced from a dragonfly

A neuropeptide with adipokinetic activity in Locusta migratoria and hypertrehalosaemic activity in Periplaneta americana was purified by reversed-phase high performance liquid chromatography from the corpus cardiacum of the dragonfly, Libellula auripennis. After brief enzymatic digestion by 5-oxoprolyl-peptidase the primary structure of the peptide was determined by pulsed-liquid phase sequencing employing Edman degradation. As the peptide was not cleaved by carboxypeptidase the C-terminus was blocked, too. The peptide was assigned as a blocked uncharged octapeptide: Glu-Val-Asn-Phe-Thr-Pro-Ser-TrpNH2. The synthetic peptide was chromatographically indistinguishable from the natural compound and, upon injection in low quantities into dragonflies, elicited mainly haemolymph lipids. Therefore it is called dragonfly adipokinetic hormone (Lia-AKH). It is a new member of the large AKH/RPCH family of peptides. Because of its structural features and its origin from a very primitive insect order it is assumed to represent the putative ancestral peptide of this family. Synthesis was shown to occur in the corpus cardiacum by in vitro incorporation of tritium-labelled Trp into Lia-AKH.     

Sperm precedence in the dragonfly Erythemis simplicicollis

Females of the dragonfly Erythemis simplicicollis (Say) (Odonata, Libellulidae) store enough sperm to fertilize 6–13 clutches of eggs laid on consecutive days. Nonetheless, they usually mate one or more times per day. Males wait for females at ponds containing surface vegetation on which the females lay eggs. Some males defend vegetation while other act as satellites. After mating, both types of males attempt to guard females against takeover by other males. Sperm precedence by male E. simplicicollis was studied using sterility produced by gamma irradiation to label sperm. After a dose-response analysis, males receiving a dose of 25 kiloroentgens (>99.9% sterile) were returned to their home pond as territory residents and satellites. Both types of males fertilized an average of 99.5% (range 97.3–100%) of the female's remaining clutch. After mating with a sterile male, females were isolated in a large cage, and eggs collected for several consecutive days. These clutches revealed that sperm mixing in the bursa of the females is essentially complete after 24 to 48 h and that the last male to mate had replaced an average of more than 57–75% of the sperm stored by female from previous matings. Thus, the last sperm in is the first sperm out fertilizing essentially all of the eggs laid soon (5–6 min) after the mating. Sperm from the most recent mating competes for fertilizations with sperm stored from previous matings only if the female oviposits on the following day without remating.     

The adipokinetic hormone of the coleopteran suborder Adephaga: Structure,function, and comparison of distribution in other insects

The aim of the current study is to identify the adipokinetic hormone(s) (AKHs) of a basal suborder of the species‐rich Coleoptera, the Adephaga, and possibly learn more about the ancestral AKH of beetles. Moreover, we wanted to compare the ancestral AKH with AKHs of more advanced beetles, of which a number are pest insects. This would allow us to assess whether AKH mimetics would be suitable as insecticides, that is, be harmful to the pest species but not to the beneficial species. Nine species of the Adephaga were investigated and all synthesize only one octapeptide in the corpus cardiacum, as revealed by Edman degradation sequencing techniques or by mass spectrometry. The amino acid sequence pGlu‐Leu‐Asn‐Phe‐Ser‐Thr‐Gly‐Trp corresponds to Schgr‐AKH‐II that was first identified in the desert locust. It is assumed that Schgr‐AKH‐II—the peptide of a basal beetle clade—is the ancestral AKH for beetles. Some other beetle families, as well as some Hymenoptera (including honey bees) also contain this peptide, whereas most of the pest beetle species have different AKHs. This argues that those peptides and their receptors should be explored for developing mimetics with insecticidal properties. A scenario where Schgr‐AKH‐II (the only AKH of Adephaga) is used as basic molecular structure to derive almost all other known beetle AKHs via single step mutations is very likely, and supports the interpretation that Schgr‐AKH‐II is the ancestral AKH of Coleoptera.     

The adipokinetic neuropeptide of Mantodea. Sequence elucidation and evolutionary relationships

A neuropeptide with adipokinetic activity in Locusta migratoria and the mantid Empusa pennata, and hypertrehalosaemic activity in Periplaneta americana, was isolated by reversed-phase high performance liquid chromatography from corpora cardiaca of the mantids E. pennata and Sphodromantis sp. After brief enzymatic digestion by 5-oxoprolylpeptidase the primary structure of the peptide of each species was determined by pulsed-liquid phase sequencing employing Edman degradation. The C-terminus of both peptides was blocked, as indicated by the lack of digestion with carboxypeptidase A. The peptides of both species were identical: a blocked, uncharged octapeptide with the sequence L-Glu-Val-Asn-Phe-Thr-Pro-Asn-Trp-NH2. The peptide is now called mantid adipokinetic hormone (Emp-AKH). The synthetic peptide was chromatographically indistinguishable from the natural compound and increased blood lipids in locusts and blood carbohydrates in cockroaches when administered in low doses. The structural features clearly define the peptide as a novel member of the large AKH/RPCH-family of peptides. Seven amino-acid residues are at identical positions in Emp-AKH when compared with the adipokinetic hormone of a dragonfly (Lia-AKH) and the hypertrehalosaemic hormone I from the American cockroach (Pea-CAH-I). Evolutionary relationships to other insect orders are discussed.     

Identification and bioactivity evaluation of a novel bradykinin inhibitory peptide from the skin secretion of Chinese large odorous frog,Odorrana livida

A novel peptide was isolated from the skin secretion of Chinese large odorous frog, Odorrana livida, and was named as Rana‐BI. The cDNA sequencing was obtained by ‘shotgun’ cloning. The amino acid sequence of the mature peptide was identified as Gly‐Leu‐Leu‐Ser‐Gly‐Lys‐Ser‐Val‐Lys‐Gly‐Ser‐Ile‐OH by automated Edman degradation, and the molecular weight of the peptide was confirmed to be 1144.68 Da by MALDI‐TOF and liquid chromatography/MS. Subsequently, the bioactivity of synthetic peptide was evaluated by smooth muscle assay using isolated rat bladder preparation. It was demonstrated that Rana‐BI inhibited the contraction of rat bladder induced by bradykinin. Comparing with other peptides by searching from database, the primary structure of Rana‐BI showed high similarity with that of an antimicrobial peptide of Rana family (12/12 residues). These data revealed a novel biological function of this peptide. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.     

An invertebrate [hydroxyproline]-modified neuropeptide: further evidence for a close evolutionary relationship between insect adipokinetic hormone and mammalian gonadotropin hormone family

An octapeptide of the adipokinetic hormone (AKH) peptide family is identified in the corpora cardiaca of the stink bug, Nezara viridula, by ESI-MS^N (electrospray ionization multistage MS). This is the second AKH in N. viridula and it has a hydroxyproline residue at position 6, whereas the major AKH (known as Panbo-RPCH) has Pro as the sixth amino acid residue. The correct sequence assignment of [Hyp⁶]-Panbo-RPCH is confirmed by retention time and MS spectra of the synthetic peptide. Various extraction procedures were followed to ascertain whether the hydroxylation is an artefact of extraction, or whether it is due to a true post-translational modification at the prohormone level. The proline hydroxylation is unique for invertebrate neuropeptides, while it has been described in the vertebrate gonadotropin-releasing hormone (GnRH). The current finding is another piece of evidence that AKH and GnRH form a peptide superfamily and are closely related evolutionarily. Biologically, [Hyp⁶]-Panbo-RPCH is active in vivo as an AKH, causing hyperlipaemia in the stink bug at low doses, indicating again that it is an endogenous, mature and functional hormone in this insect species.     

Purification,characterization and application of a novel antimicrobial peptide from Andrias davidianus blood

The Andrias davidianus has been known as a traditional Chinese medicine for a long time. Its blood is considered as a waste or by‐product of the meat production industry. Although there are reports on isolation of the antimicrobial peptides from different resources, there are no reports of their isolation from A. davidianus blood. In this work, an antimicrobial peptide, andricin B, was isolated from the blood of A. davidianus by an innovative method in which the magnetic liposome adsorption was combined with reversed‐phase high‐performance liquid chromatography. The structure, antimicrobial activity and safety of andricin B were further investigated. Amino acid sequence was determined by N‐terminal sequencing and found to be Gly‐Leu‐Thr‐Arg‐Leu‐Phe‐Ser‐Val‐Ile‐Lys. Circular dichroism (CD) spectra and prediction of three‐dimensional structure by bioinformatics software suggested the presence of a well‐defined random coil conformation. Andricin B was found to be active against all bacteria tested in this study as well as some fungi. The minimum inhibitory concentrations (MICs) were in the range 8–64 μg ml^?1. Moreover, the haemolytic testing also suggested that andricin B could be considered safe at the MICs. Finally, andricin B was shown to inhibit the growth of Staphylococcus aureus in the cooked meat of A. davidianus. This study shows that andricin B is a promising novel antimicrobial peptide that may provide further insights towards the development of new drugs.

Significance and Impact of the Study

This is the pioneer study on screening and isolation of antimicrobial peptide from the blood of Andrias davidianus. Here, we have developed a novel method by combining magnetic liposomes adsorption with reversed‐phase high‐performance liquid chromatography to purify and screen the antimicrobial peptides. From this screen, we identified a novel antimicrobial peptide which we name as andricin B. Andricin B is unique as it checks the growth of both Gram‐positive and Gram‐negative bacteria as well as few fungal species.     

Adipokinetic hormone counteracts oxidative stress elicited in insects by hydrogen peroxide: in vivo and in vitro study

The role of adipokinetic hormone (AKH) in counteracting oxidative stress elicited in the insect body is studied in response to exogenously applied hydrogen peroxide, an important metabolite of oxidative processes. In vivo experiments reveal that the injection of hydrogen peroxide (8 µmol) into the haemocoel of the firebug, Pyrrhocoris apterus L. (Heteroptera: Pyrrhocoridae) increases the level of AKH by 2.8‐fold in the central nervous system (CNS) and by 3.8‐fold in the haemolymph. The injection of hydrogen peroxide also increases the mortality of experimental insects, whereas co‐injection of hydrogen peroxide with Pyrap‐AKH (40 pmol) reduces mortality to almost control levels. Importantly, an increase in haemolymph protein carbonyl levels (i.e. an oxidative stress biomarker) elicited by hydrogen peroxide is decreased by 3.6‐fold to control levels when hydrogen peroxide is co‐injected with Pyrap‐AKH. Similar results are obtained using in vitro experiments. Oxidative stress biomarkers such as malondialdehyde and protein carbonyls are significantly enhanced upon exposure of the isolated CNS to hydrogen peroxide in vitro, whereas co‐treatment of the CNS with hydrogen peroxide and Pyrap‐AKH reduces levels significantly. Moreover, a marked decrease in catalase activity compared with controls is recorded when the CNS is incubated with hydrogen peroxide. Incubation of the CNS with hydrogen peroxide and Pyrap‐AKH together curbs the negative effect on catalase activity. Taken together, the results of the present study provide strong support for the recently published data on the feedback regulation between oxidative stressors and AKH action, and implicate AKH in counteracting oxidative stress. The in vitro experiments should facilitate research on the mode of action of AKH in relation to oxidative stress, and could help clarify the key pathways involved in this process.     

The adipokinetic hormones of Heteroptera: a comparative study

The adipokinetic hormones (AKHs) from 15 species of heteropteran Hemiptera (encompassing eight families, six superfamilies and three infraorders) have been isolated and structurally identified using liquid chromatography coupled with mass spectrometry. None of the structures are novel and all are octapeptides. These peptide sequence data are used, together with the previously available AKH sequence data on Heteroptera, to create a larger dataset for comparative analyses. This results, in total, in AKH sequences from 30 species (spanning 13 families), which are used in a matrix confronted with the current hypotheses on the phylogeny of Heteroptera. The expanded dataset shows that all heteropterans have octapeptide AKHs; three species have two AKHs, whereas the overwhelming majority have only one AKH. From a total of 11 different AKH peptides known from Heteroptera to date, three AKHs occur frequently: Panbo‐red pigment‐concentrating hormone (RPCH) (×10), Schgr‐AKH‐II (×6) and Anaim‐AKH (×4). The heteropteran database also suggests that particular AKH variants are family‐specific. The AKHs of Heteroptera: Pentatomomorpha (all terrestrial) are not present in Nepomorpha (aquatic) and Gerromorpha: Gerridae (semiaquatic); AKHs with a Val in position 2 are absent in the Pentatomomorpha (only AKHs with Leu² are present), whereas Val² predominates in the nonterrestrial species. An unexpected diversity of AKH sequences is found in Nepomorpha, Nepoidea, Nepidae and Nepinae, whereas Panbo‐RPCH (which has been identified in all infraorders of decapod crustaceans) is present in all analysed species of Pentatomidae and also in the only species of Tessaratomidae investigated. The molecular evolution of Heteroptera with respect to other insect groups and to crustaceans is discussed     

Effect of one D‐Leu residue on right‐handed helical ‐L‐Leu‐Aib‐ peptides in the crystal state

Four diastereomeric‐Leu‐Leu‐Aib‐Leu‐Leu‐Aib‐peptides, Boc‐D ‐Leu‐L ‐Leu‐Aib‐L ‐Leu‐L ‐Leu‐Aib‐OMe (1), Boc‐L ‐Leu‐D ‐Leu‐Aib‐L ‐Leu‐L ‐Leu‐Aib‐OMe (2), Boc‐L ‐Leu‐L ‐Leu‐Aib‐D ‐Leu‐L ‐Leu‐Aib‐OMe (3), and Boc‐L ‐Leu‐L ‐Leu‐Aib‐L ‐Leu‐D ‐Leu‐Aib‐OMe (4), were synthesized. The crystals of the four hexapeptides were characterized by X‐ray crystallographic analysis. Two diastereomeric hexapeptides 1 and 2 having D ‐Leu(1) or D ‐Leu(2) were folded into right‐handed (P) 3 ₁₀ ‐helical structures, while peptide 3 having D ‐Leu(4) was folded into a turn structure nucleated by type III′ and I$' \bf{\beta}$ ‐turns, and peptide 4 having D ‐Leu(5) was folded into a left‐handed (M) 3 ₁₀ ‐helical structure. Copyright © 2011 European Peptide Society and John Wiley & Sons, Ltd.