Defensive potential of components of the larval osmeterial secretion of papilionid butterflies against ants

ABSTRACT. Toxicity and repellency of components of larval osmeterial secretions of the Papilionidae to the ants Lasius niger and Crematogaster matsumurai were evaluated in the laboratory and in the field. The test chemicals comprised five aliphatic acids, five esters, three monoterpene hydrocarbons and four sesquiterpenes.
The majority of aliphatic acids and esters exhibited weak to potent toxicity, but exposure to acetic, isobutyric, 2-methylbutyric and isovaleric acids, ethyl 2-methylbutyrate and methyl 3-hydroxy- n -butyrate proved fatal to both ant species. Monoterpene hydrocarbons also had considerable toxicity, whereas sesquiterpenes were only slightly or not toxic. Of the terpenic compounds tested, α-pinene was found to be the most toxic. L. niger ejected formic acid in response to d -limonene.
Field experiments revealed that all the compounds examined except 3-hydroxy- n -butyric acid were significantly repellent to worker ants of both species. Acetic, isobutyric and 2-methylbutyric acids especially showed pronounced repellency, while the esters were less deterrent.
Among terpenic compounds, the repellency of caryophyllene oxide was noticeable. d -Limonene elicited no particular response, other than rapid evasion, by L. niger.     

Studies on the synthesis of safflomin-A, a yellow pigment in safflower petals: oxidation of 3-C-beta-d-glucopyranosyl-5-methylphloroacetophenone

The direct C-glycosylation of methylphloroacetophenone 8 with d-glucose gave C-beta-d-glucopyranosylmethylphloroacetophenone (7) in 65% yield, which, on oxidation in the presence of small amount of pyridine under an oxygen atmosphere afforded the quinone 9, oxidized at the methylated position of the benzene ring as a pair of diastereomers in 27% yield. A detailed NMR analysis and a comparison of the UV-vis and CD spectra of their acetates indicated that the structure and stereochemistry of 9 was (1R,1'S,2R,3S,3aS,5R and 1R,1'S,2R,3S,3aS,5S)-7-acetyl-2-(1',2'-dihydroxyethyl)-5-methyl-3,5,6-trihydroxy-8-oxofuro[3,2-d]benzo[b]furan.     

Beak marks on the wings of butterflies and predation pressure in the field

Beak marks on butterfly wings have been used as an indicator of predation pressure. The relationship between butterflies and their predators in the field was examined to evaluate the beak mark rate as an indicator of predation pressure. Transect censuses were conducted to measure the beak mark rate on butterflies from May to November, 2010, in Shiga Prefecture, Japan. A total of 1216 butterflies of 42 species from five families were observed during the study period. The beak mark rate in the Papilionidae was significantly higher than those of all other families. Analysis of the monthly fluctuations in the beak mark rate and relative abundance of predators revealed that the higher beak mark rates observed for two butterfly families (Papilionidae and Nymphalidae) were significantly and positively related to predation pressure, while no significant relationship was found for other families (Lycaenidae, Pieridae and Hesperiidae). Beak marks in larger butterflies (Papilionidae and Nymphalidae) can be used as an indicator to evaluate the relative intensity of predation pressure in the field.     

Variation in UV light reflected from the wings of Favonius and Quercusia butterflies

The wing colors of eight lycaenid species of the genera Favonius and Quercusia were examined with a spectrophotometer. Four (F. orientalis, F. taxila, F. jezoensis and F. ultramarinus) of five green to blue‐green Favonius species had a double‐peaked pattern, reflecting UV light (345–355 nm) and green light (515–525 nm), whereas F. cognatus reflected only visible green light (539 nm). Thus, the species considered most closely related, F. ultramarinus and F. cognatus, had quite different wing colors in terms of insect vision. Two bluish species had utterly different reflection patterns: F. saphrinus had a single peak in the UV range and Q. fujisana had two peaks, one each in the UV and visible light ranges. The black F. yuasai did not have any peak in the examined range of wavelengths (300–700 nm).     

Enzymic peptide synthesis in microaqueous, solvent-free systems

Thermolysin-catalyzed (EC 3.4.24.4) and chymotrypsin-catalyzed (EC 3.4.21.1) peptide synthesis reactions were accomplished without any organic solvent in the presence of low amounts of water under sonication and fluidization. The systems used are considered to be microaqueous solvent-free ones. The influence of several reaction parameters, such as time, the amount of enzyme, the amount of water in free form or bound as hydration water, and the N/C component ratio, on the vield of the thermolysin-catalyzed synthesis of Z-Phe-Leu-NH(2) (up to 87% yield) was investigated in a sonicated system. Besides Z-Phe-Leu-NH(2), the tripeptide derivatives Ac-Xaa-Trp-Leu-NH(2), (Xaa = Gly, Ala) were also obtained in good yields of 79 and 71% respectively. In the latter case, no hydrolytic side reactions were observed. Using a fluidized-bed reactor, chymotrypsin- and thermolysin-catalyzed syntheses of N-protected di- and tripeptide amides could be perfromed with yields in the range of 10 to 40%. (c) 1995 John Wiley & Sons, Inc.     

The pigment system of the photoreceptor 7 yellow in the fly,a complex photoreceptor

Summary The 7y photoreceptor in the fly (Musca, Calliphora) retina harbours an unusually complex pigment system consisting of a bistable visual pigment (xanthopsin, X and metaxanthopsin, M), a blue-absorbing C₄₀-carotenoid (zeaxanthin and/or lutein) and a uv sensitizing pigment (3-OH retinol).The difference spectrum and photoequilibrium spectrum in single 7y rhabdomeres were determined microspectrophotometrically (Fig. 2).The extinction spectrum of the C₄₀-carotenoid has a pronounced vibrational structure, with peaks at 430, 450 and 480 nm (Fig. 3). The off-axis spectral sensitivity, determined electrophysiologically with 1 nm resolution shows no trace of this fine structure thus excluding the possibility that the C₄₀-carotenoid is a second sensitizing pigment (Fig. 4).The absorption spectra of X and M are derived by fitting nomogram spectra (based on fly R1–6 xanthopsin) to the difference spectrum. max for X is 425 nm, and for M 510 nm (Fig. 5). It is shown that the photoequilibrium spectrum and the difference spectrum can be used to derive the relative photosensitivity spectra of X and M using the analytical method developed by Stavenga (1975). The result (Fig. 6) shows a pronounced uv sensitivity for both, X and M, indicating that the uv sensitizing pigment transfers energy to both X and M. A value of 0.7 for, the relative efficiency of photoconversion for X and M, is obtained by fitting the analytically derived relative photosensitivity spectra to the absorption spectra at wavelengths beyond 420 nm.     

Enzymic synthesis of floridean starch in a red alga, Serraticardia maxima

ADP-glucose: -l,4-glucan -4-glucosyltransferase was obtainedfrom a marine red alga Serraticardia maxima in a form boundwith floridean starch granules. The enzyme catalyzed the transferof glucosyl residue from ADP-glucose, UDP-glucose and GDP-glucoseto floridean starch added as a primer. ADP-glucose was the mostefficient glucosyl donor in the reaction. Maltose was producedby ß-amylolysis of the glucan synthesized by the algalenzyme. The optimum pH for enzyme activity was at 8.4. The enzymewas not obtained in a soluble form from either the chloroplastextract or the whole algal cell extract. Electron micrographsof algal cells revealed that floridean starch granules are localizedexclusively outside chloroplasts. Hence, it appears that mostof the synthetase is present outside chloroplasts. ¹ Contribution from the Shimoda Marine Biological Station, TokyoKyoiku University, No. 202. This work was supported by a Grant-in-Aidfor Cooperative Research from the Ministry of Education, Japan. ² Present address: Department of Biology, Faculty of Science,Science University of Tokyo, Kagurazaka, Tokyo 162, Japan. ³ Present address: Laboratory of Biology, Faculty of Science,Toho University, Narashino, Chiba 275, Japan. (Received May 25, 1970; )     

Enzymic synthesis of lacto-N-triose II and its positional analogues

N-acetylhexosaminidase fromNocardia orientalis catalysed the synthesis of lacto-N-triose II glycoside (-d-GlcNAc-(1-3)--d-Gal-(1-4)--d-Glc-OMe,3) with its isomers -d-GlcNAc-(1-6)--d-Gal-(1-4)--d-Glc-OMe (4) and -d-Gal-(1-4)-[-d-GlcNAc-(1-6)]--d-Glc-OMe (5) throughN-acetylglucosaminyl transfer fromN,N-diacetylchitobiose (GlcNAc₂) to methyl -lactoside. The enzyme formed the mixture of trisac-charides3, 4 and5 in 17% overall yield based on GlcNAc₂, in a ratio of 20:21:59. Withp-nitrophenyl -lactoside as an acceptor, the enzyme also producedp-nitrophenyl -lacto-N-trioside II (-d-GlcNAc-(1-3)--d-Gal-(1-4)--d-Glc-OC₆H₄NO₂-p,6) with its isomers -d-GlcNAc-(1-6)--d-Gal-(1-4)--d-Glc-OC₆H₄NO₂-p (7) and -d-Gal-(1-4)-[-d-GlcNAc-(1-6)]--d-Glc-OC₆H₄NO₂-p (8). In this case, when an inclusion complex ofp-nitrophenyl lactoside acceptor with -cyclodextrin was used, the regioselectivity of glycosidase-catalysed formation of trisaccharide glycoside was substantially changed. It resulted not only in a significant increase of the overall yield of transfer products, but also in the proportion of the desired compound6.Abbreviations GlcNAc₂ 2-acetamido-2-deoxy--d-glucopyranosyl-(1-4)-2-acetamido-2-deoxy-d-glucose - NAHase N-acetylhexosaminidase - -CD -cyclodextrin     

Patterns of Amazonian area relationships based on raw distributions of papilionid butterflies (Lepidoptera: Papilioninae)

Diversifications within a biota are due to several factors. Although some of these are untestable with current analytical methods, hierarchical congruence obtained with different cladistic methods and based on independent taxa are undoubtedly important. In the recent past, most hypotheses of historical biogeography (e.g. refugial, riverine, disturbance, vicariance) were tested on the Amazonian biota, selecting a number of diverse organisms such as plants, anurans, lizards, butterflies, birds and monkeys. In this study we used parsimony analysis of endemicity to infer historical relationships among 16 interfluvial areas in the Amazonian lowlands based on raw distributions of 114 Papilioninae (Lepidoptera). The analysis yielded two most parsimonious trees of area relationships. One tree was characterized by two main clusters of areas which showed a separation of Guyanan + south-east Amazonian interfluvial areas from western Amazonian interfluvial areas. The second tree showed the Guyanan interfluvial areas basal to a cluster which included all the other interfluvial areas. This latter cluster was subdivided into two main groups of areas separating the south-east Amazonian and the western Amazonian interfluvial areas. This result is discussed in the light of previous hypotheses obtained with the same method using some vertebrate taxa in the Amazonian lowlands. Likewise, comparisons with other hypotheses on lineages of birds, mammals and butterflies obtained applying cladistic biogeographical methods are made. The two alternative vicariant patterns presented for papilionid butterflies are strictly congruent with those for birds.  © 2004 The Linnean Society of London, Biological Journal of the Linnean Society , 2004, 82 , 345–357.     

Microsatellite markers associated with genes expressed in developing wings of Bicyclus anynana butterflies

Deriving useful microsatellite markers in lepidopterans has been challenging when relying on scans of genomic DNA libraries, presumably due to repetitiveness in their genomes. We assayed 96 of 320 microsatellites identified in silico from a collection of Bicyclus anynana ESTs, in 11 independent individuals from a laboratory population. From the 68 successful assays, we identified 40 polymorphic markers including 22 with BLAST-based annotation. Nine of 12 selected polymorphic markers tested in a panel of 24 wild-caught individuals converted to successful assays and were all polymorphic. We discuss how microsatellite discovery in ESTs is an efficient strategy with important attendant advantages.