Pigments biliaires des lépidoptères: Identification de la phorcabiline I et de la sarpédobiline chez diverses espèces

Choussy, M.; Barbier, Michel

doi:10.1016/0305-1978(73)90013-6

Cited by 17 publications

(8 citation statements)

References 3 publications

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“…The position of the vinyl groups in the tetrapyrrole molecule is determining for photo-reactivity. The irradiation of biliverdin IX y (1, pterobilin), occurring in many Lepidopter species [17], leads to the formation of a complex mixture of new pigments, proceeding from reactions of the C(7')-vinyl group, the C(8)-vinyl group or both, the only products identified being neobiliverdin IX y (phorcabilin) and sarpedobilin [15] [18] [19]. These natural pigments have been isolated, as biliverdin IX y , (pterobilin) [17] from Lepidopter species.…”

Section: Discussionmentioning

confidence: 99%

Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IX_γ (pterobilin)

Bois‐Choussy

Barbier

1980

Helvetica Chimica Acta

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SummaryThe configurations of biliverdin-IXy and -1X6 dimethyl esters 1 and 2 in solutions, have been studied using Nuclear-Overhauser-Effect (NOE) experiments.Irradiation (500-700 nm) of biliverdin 1x6 gave syn-2-t anti-E isomerization of the central methine bridge and in aerated polar solutions, four new cyclized pigments were isolated for which structures 3, 4, 5 and 6 are proposed. Neobiliverdin 1x6 3 is also formed in degassed solution (~D=4.10-~) but pigments 4, 5 and 6 arise from photo-oxidation with 0 2 . Biliverdin 1 x 6 appears to be a good model for the study of photo-reactions occurring on the vinyl groups of the natural biliverdin IX y (pterobilin).Introduction. -Photo-excitation of bilirubin IXa in aerated solution leads to self-oxidation resulting in a variety of degradation products [l-61 such as maleimides, dipyrrole dialdehydes and propentdyopents. These reactions are self sensitized, involving triplet bilirubin (energy level 150 kJ mol-' [7]) and singlet oxygen [4] probably generated by energy transfer from triplet excited bilirubin. In oxygen-free medium, (Z, Z)-bilirubin IX a is isomerized to a mixture of (2, E)-, ( E , 2)-and (E, E)-isomers In preceding papers [ 151 [ 161 we compared the photo-reactivity of biliverdin-IX isomers; whereas biliverdin IXa and TXP are relatively photo-stable in aerated

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Section: Discussionmentioning

confidence: 99%

Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IX_γ (pterobilin)

Bois‐Choussy

Barbier

1980

Helvetica Chimica Acta

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“…Although the vast majority of bile pigments are derived by cleavage at the a methine carbon of heme, there are biological precedents for bile pigments cleaved at other methine carbons. Thus, the pigment pterobilin from Lepidoptera (28,(30)(31)(32) has been shown to be biliverdin IXy (33, 34); (36); and the 8, 1B, and y isomers have been reported in man, pig, dog, and rat bile (37). The above discussion assumes that the sequence of side chains in bactobilin corresponds to that found in uroporphyrin III.…”

Section: Methodsmentioning

confidence: 99%

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Brumm¹,

Fried²,

Friedmann³

1983

Proc. Natl. Acad. Sci. U.S.A.

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A blue bile pigment, possessing four acetic and four propionic acid side chains has been isolated from extracts of the anaerobic microorganism Clostridium tetanomorphum and in smaller amounts from Propionibacterium shermanii. The compound could be prepared in larger amounts by incubation of C. tetanomorphum enzyme extracts with added 8-aminolevulinic acid. The ultraviolet-visible, infrared, and proton magnetic resonance spectra of the pigment indicate a chromophore of the biliverdin type. Field-desorption mass spectrometry of the purified methyl ester showed a strong molecular ion at m/e = 962. This corresponds to the molecular weight expected for the octamethyl ester of a bilatriene type of bile pigment structurally derived from uroporphyrin 1m or I. Of the five possible structures, two could be eliminated by proton magnetic resonance spectroscopy. The name bactobilin is proposed for this previously unreported bile pigment.The open-chain tetrapyrrole compounds known as bile pigments are widely distributed. They are found free or bound to protein in mammals, birds, amphibians, reptiles, fish, molluscs, and insects and in algae and higher plants (for reviews, see refs. 1-9). As side chains or 1&carbon ring substituents, all bile pigments described thus far have four methyl groups, two propionic acid groups, and two vinyl groups, one or both of which can be isomerized to ethylidene (4, 10, 11) or reduced to ethyl (6,10,11). These substituents are arranged in the sequence found in protoporphyrin IX; in fact, all these bile pigments are formed from protoheme (8,(12)(13)(14), whose oxidative breakdown to biliverdin is catalyzed by the enzyme heme oxygenase (15-17). Bile pigments thus far have not been detected in prokaryotes. The present paper reports the isolation and in vitro formation of a bile pigment from the bacterium Clostridium tetanomorphum. This anaerobic organism makes uroporphyrinogen, the precursor of vitamin B-12, but not heme, protoporphyrinogen, or coproporphyrinogen. The isolated bile pigment is of interest not only because of its detection in a prokaryote, but also because its 13-carbon ring substituents, four acetic acid and four propionic acid groups, correspond to those of a uroporphyrin and not of protoporphyrin. MATERIALS AND METHODSSupplies. -Aminolevulinic acid was obtained from Sigma;biliverdin IXa dimethyl ester and the fully esterified methyl esters of uroporphyrin III, coproporphyrin III, protoporphyrin IX, and heptacarboxylporphyrin I, were from Porphyrin Products (Logan, UT). The n-hexane used for flash chromatography was "95 + %" (Aldrich), whereas the n-hexane for thin-layer chromatography was 99 mol % pure (Fisher). Other chemicals used were reagent grade or better. Silica gel for flash chromatography and a flash chromatography column, 3.4-cm diameter, were obtained from J. T. Baker. Whatman high-performance silica thin-layer chromatography plates with a preadsorbent spotting area (type LHP-K, 10 x 20 cm) and E. Merck precoated cellulose thin-layer chromatography plates were...

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“…Rare exceptions to this general rule are the bile pigments phorcabilin, pterobilin and sarpedobilin, which absorb prominently in the blue and red wavelength range, but not in between, thus yielding blue-green wing colours (Barbier, 1981;, which are found in the papilionids Papilio phorcas, Graphium sarpedon and a number of other Graphium species, and also in some nymphalids (Choussy and Barbier, 1973).…”

Section: Introductionmentioning

confidence: 99%

Papiliochrome II pigment reduces the angle dependency of structural wing colouration innireusgroup papilionids

Wilts

Trzeciak

Vukusic

et al. 2012

Journal of Experimental Biology

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SUMMARYThe wings of four papilionid butterfly species of the nireus group, Papilio bromius, P.epiphorbas, P.nireus and P.oribazus, are marked by blue-green coloured bands surrounded by black margins. The cover scales in the coloured bands contain a violetabsorbing, blue-fluorescing pigment. The fluorescence and absorbance spectra of the nireus group wings are very similar to those of the wings of the Japanese yellow swallowtail, Papilio xuthus, and thus the pigment is presumably papiliochromeII. The scale structures of P. xuthus are arranged irregularly, and both the fluorescence and light reflection are diffuse. In the nireus papilionids, the spatial fluorescence distribution of the scales is also diffuse, but the reflection is specular. The scales have a multilayered structure, consisting of two main laminae. We show that the papiliochromeII pigment in the upper lamina of the scales functions as a violet-blocking long-pass filter in front of the lower lamina, thus limiting the reflectance spectrum to the blue-green wavelength range. Optical modelling showed that the papiliochromeII filter effectively removes the angle dependency of the reflectance spectra -that is, it reduces the wing iridescence. The contribution of the fluorescence signal to the visual appearance is minor.

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Pigments biliaires des lépidoptères: Identification de la phorcabiline I et de la sarpédobiline chez diverses espèces

Cited by 17 publications

References 3 publications

Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IX_γ (pterobilin)

Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IX_γ (pterobilin)

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Papiliochrome II pigment reduces the angle dependency of structural wing colouration innireusgroup papilionids

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Pigments biliaires des lépidoptères: Identification de la phorcabiline I et de la sarpédobiline chez diverses espèces

Cited by 17 publications

References 3 publications

Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IXγ (pterobilin)

Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IXγ (pterobilin)

Bactobilin: blue bile pigment isolated from Clostridium tetanomorphum.

Papiliochrome II pigment reduces the angle dependency of structural wing colouration innireusgroup papilionids

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Product

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Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IX_γ (pterobilin)

Photochemistry of Biliverdin IX δ as a model for the study of the photoproducts from natural biliverdin IX_γ (pterobilin)