Erythropterin
(Synonyms: 红喋呤) 目录号 : GC36005Erythropterin 是一种蝶呤衍生物 (Pterin derivative)。蝶呤衍生物是经常在生物系统中发现的杂环化合物,它负责一些异翅目昆虫和其他昆虫的特征警告着色,表明有害或不适应,并用于阻止潜在的捕食者攻击。
Cas No.:7449-03-8
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Erythropterin is a Pterin derivative that belongs in a group of heterocyclic compounds that are frequently found in biological systems. Pterin derivatives are responsible for the characteristic warning coloration of some Heteroptera and other insects, signaling noxiousness or unpalatability and are used to discourage potential predators from attacking[1].
[1]. KrajÍ?ek J, et al. Capillary electrophoresis of pterin derivatives responsible for the warning coloration of Heteroptera. J Chromatogr A. 2014 Apr 4;1336:94-100.
Cas No. | 7449-03-8 | SDF | |
别名 | 红喋呤 | ||
Canonical SMILES | O=C(O)C(/C=C1C(NC2=C(N=C(N)NC2=O)N\1)=O)=O | ||
分子式 | C9H7N5O5 | 分子量 | 265.18 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mM | 3.771 mL | 18.8551 mL | 37.7102 mL |
5 mM | 0.7542 mL | 3.771 mL | 7.542 mL |
10 mM | 0.3771 mL | 1.8855 mL | 3.771 mL |
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Mechanisms of color production in a highly variable shield-back stinkbug, Tectocoris diophthalmus [corrected] (Heteroptera: Scutelleridae), and why it matters
PLoS One 2013 May 7;8(5):e64082.PMID:23675520DOI:10.1371/journal.pone.0064082.
Theory suggests that aposematism, specifically the learned avoidance of unprofitable prey via memorable color patterns, should result in selection for pattern uniformity. However, many examples to the contrary are seen in nature. Conversely, honest sexual signals are likely to exhibit greater variation because they reflect underlying variation in mate quality. Here we aim to characterize and quantify the mechanistic causes of color in Tectocoris diophthalmus [corrected] to shed light on the costs of color production, and thus the potential information content of its color signals. We use Tectocoris diophthalmus [corrected] because it is a weakly-defended stinkbug, and presents elements that have classically been studied in the context of aposematism (red coloring), and sexual selection (sexual dichromatism and iridescent coloring). Pigment analysis reveals that variation in orange coloration is due to the amount of Erythropterin pigment, stored in intracellular granules. This pigment is common in Heteroptera, and as an endogenously produced excretory byproduct is unlikely to reflect mate quality or variation in unprofitability of the bug. Electron microscopy reveals the iridescent patches are caused by an epicuticular multilayer reflector, and the hue and patch size are directly related to the layer widths and extent of coverage of this layering. Furthermore, we identified melanin as an essential component of the multilayer reflector system; therefore, the quality of the iridescent patches may be affected by aspects of rearing environment and immunocompetence. We posit that T. diophthalmus [corrected] has co-opted the melanic patches of a 'typical' red and black aposematic signal, transforming it into a complex and variable iridescent signal that may enhance its capacity to display individual quality.
Presence of pterin pigments in wings of libytheidae butterflies
J Chem Ecol 1987 Aug;13(8):1843-7.PMID:24302393DOI:10.1007/BF01013233.
A few pterin pigments were discovered in the wings of six of eight libytheid species tested, using thin-layer chromatography with 1 % HC1 in butanol as a solvent. A 10X sample ofLibytheana bachmanii larvata (Strecker) produced xanthopterin, isoxanthopterin, Erythropterin, and leucopterin. Leucopterin was absent in the other libytheids tested. Morphology and pterin pigment data from wings suggest a Pieridae ancestry for the Libytheidae from the region of the northern Neotropical realm (including the Greater Antilles).
Hydrophilic interaction liquid chromatography with tandem mass spectrometric detection applied for analysis of pteridines in two Graphosoma species (Insecta: Heteroptera)
J Chromatogr B Analyt Technol Biomed Life Sci 2013 Jul 1;930:82-9.PMID:23727871DOI:10.1016/j.jchromb.2013.05.004.
A new separation method involving hydrophilic interaction chromatography with tandem mass spectrometric detection has been developed for the analysis of pteridines, namely biopterin, isoxanthopterin, leucopterin, neopterin, xanthopterin and Erythropterin in the cuticle of heteropteran insect species. Two columns, Atlantis HILIC Silica and ZIC(®)-HILIC were tested for the separation of these pteridines. The effect of organic modifier content, buffer type, concentration and pH in mobile phase on retention and separation behavior of the selected pteridines was studied and the separation mechanism was also investigated. The optimized conditions for the separation of pteridines consisted of ZIC(®)-HILIC column, mobile phase composed of acetonitrile/5mM ammonium acetate, pH 6.80, 85/15 (v/v), flow rate 0.5mL/min and column temperature 30°C. Detection was performed by tandem mass spectrometry operating in electrospray ionization with Agilent Jet Stream technology using the selected reaction monitoring mode. The optimized method provided a linearity range from 0.3 to 5000ng/mL (r>0.9975) and repeatability with relative standard deviation<8.09% for all the studied pteridines. The method was applied to the analysis of pteridines in the cuticle of larvae and three adult color forms of Graphosoma lineatum and one form of Graphosoma semipunctatum (Insecta: Hemiptera: Heteroptera: Pentatomidae). The analysis shows that different forms of Graphosoma species can be characterized by different distribution of individual pteridines, which affects the coloration of various forms. Only isoxanthopterin was found in all the five forms tested.
Polymorphism of Colias croceus from the Azores caused by differential pterin expression in the wing scales
J Insect Physiol 2020 Nov-Dec;127:104114.PMID:32905790DOI:10.1016/j.jinsphys.2020.104114.
The pierid butterfly Colias croceus (Geoffroy in Fourcroy, 1785), established in the Azores archipelago, is polymorphic with six forms, C. croceus f. croceus ♂ and ♀, C. c. f. cremonae ♂ and ♀, C. c. f. helice ♀, and C. c. f. cremonaehelice ♀. We investigated the optical mechanisms underlying the wing colouration of the butterflies by performing spectrophotometry and imaging scatterometry of the variously coloured wing areas and scales. The scale colouration is primarily due to wavelength-selective absorption of incident light by pterins expressed in granular beads in the wing scales, but thin film reflections of the scales' lower lamina and scale stacking also contribute. Three forms (croceus ♂ and ♀ and helice ♀) are consistent with the patterns of the well-known 'alba' polymorphism. We postulate the coexistence of a second polymorphism, 'cremonae', to understand the three other forms (cremonae ♂ and ♀, and cremonaehelice ♀), which are characterized by the absence of red pigment, presumably due to the differential blocking of Erythropterin expression.
Capillary electrophoresis of pterin derivatives responsible for the warning coloration of Heteroptera
J Chromatogr A 2014 Apr 4;1336:94-100.PMID:24602308DOI:10.1016/j.chroma.2014.02.019.
A new capillary electrophoretic (CE) method has been developed for analysis of 10 selected derivatives of pterin that can occur in the integument (cuticle) of true bugs (Insecta: Hemiptera: Heteroptera), specifically L-sepiapterin, 7,8-dihydroxanthopterin, 6-biopterin, D-neopterin, pterin, isoxanthopterin, leucopterin, xanthopterin, Erythropterin and pterin-6-carboxylic acid. Pterin derivatives are responsible for the characteristic warning coloration of some Heteroptera and other insects, signaling noxiousness or unpalatability and are used to discourage potential predators from attacking. Regression analysis defining the parameters significantly affecting CE separation was used to optimize the system (the background electrolyte (BGE) composition, pH value and applied voltage). The optimized separation conditions were as follows: BGE with composition 2 mmol L(-1) the disodium salt of ethylendiamintetraacetic acid, 100 mmol L(-1) tris(hydroxymethyl)aminomethane and 100 mmol L(-1) boric acid, pH 9.0, applied voltage 20 kV and UV detection at 250 nm. Under these conditions, all the 10 studied derivatives of pterin were baseline separated within 22 min. The optimized method was validated from the viewpoint of linearity (R(2)≥0.9980), accuracy (relative error ≤7.90%), precision (for repeatability RSD≤6.65%), detection limit (LOD in the range 0.04-0.99 μg mL(-1)) and limit of quantitation (LOQ in the range 0.13-3.30 μg mL(-1)). The developed method was used for identification and determination of the contents of pterin derivatives in adults of four species of Heteroptera (Eurydema ornata cream color morph, Scantius aegyptius, Pyrrhocoris apterus and Corizus hyoscyami) and their distribution in the individual species was determined.