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PubMed2003

Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occurring in aging red wines.

Three newly formed pigments were detected and isolated from a 2-year-old Port wine through TSK Toyopearl HW-40(S) gel column chromatography and characterized by UV-visible spectrophotometry, NMR, and mass spectrometry (ESI/MS). (1)H NMR and (13)C NMR data for these pigments obtained using 1D and 2D NMR techniques (COSY, NOESY, gHSQC, and gHMBC) are reported for the first time. The structure of the pigments was found to correspond to the vinyl cycloadducts of malvidin 3-coumaroylglucoside bearing either a procyanidin dimer or a flavanol monomer ((+)-catechin or (-)-epicatechin). Additionally, conformational analysis was performed for one of these newly formed pigment using computer-assisted model building and molecular mechanics. A chemical nomenclature is proposed to unambiguously name this new family of anthocyanin-derived pigments.

Acylation↗
PubMed2002

Optimizing conditions for the extraction of pigments in cochineals (Dactylopius coccus Costa) using response surface methodology.

A simple method was developed for the extraction and determination of color pigments in cochineals (Dactylopius coccus Costa). The procedure was based on the solvent extraction of pigments in insect samples using methanol:water (65:35, v:v) as extractant. Two-level factorial design was used in order to optimize the solvent extraction parameters: temperature, time, methanol concentration in the extractant mixture, and the number of extractions. The results suggest that the number of extractions is statistically the most significant factor. The separation and determination of the pigments was carried out by high-performance liquid chromatography with UV-visible detection. Because the absorption spectra of different pigments are different in the visible region, it is convenient to use a diode array detector to obtain chromatographic profiles that allow for the characterization of the extracted pigments.

Animals↗
PubMed2005

Enhanced photostability of monascus pigments derived with various amino acids via fermentation.

The photostability of 18 amino acid derivatives from monascus pigment was tested under various physical and chemical conditions. Under sunlight, the half-life of derivatives was increased to 1.45-5.58 h, corresponding to a 6-25-fold improvement over a control red pigment (0.22 h). The degradation of pigment derivatives followed a first-order reaction, and the pigment stability increased with an increasing concentration while it decreased with both an increase and decrease in pH from 7. The stabilities of derivatives decreased in descending order in hexane, ethanol, propanol, methanol, ethyl ether, distilled water, chloroform, and acetonitrile. Pigment stability under UV light (365 nm) showed a pattern similar to stability after exposure to sunlight. After 30 days of incubation at 30 degrees C, more than 80% of the initial derivative contents remained while only 29% of the control red remained. The differences in degradation patterns that control red gradually changed to brown whereas the phenylalanine derivative remained a weak red were confirmed by HPLC analysis.

Amino Acids↗
PubMed2006

Pigments in avocado tissue and oil.

Pigments are important contributors to the appearance and healthful properties of both avocado fruits and the oils extracted from these fruits. This study determined carotenoid and chlorophyll pigment concentrations in the skin and three sections of the flesh (outer dark green, middle pale green, and inner yellow flesh-nearest the seed) and anthocyanin concentrations in the skin of Hass avocado during ripening at 20 degrees C. Pigments were extracted from frozen tissue with acetone and measured using high-performance liquid chromatography. Pigments were also measured in the oil extracted from freeze-dried tissue sections by an accelerated solvent extraction system using hexane. Carotenoids and chlorophylls identified in the skin, flesh, and oil were lutein, alpha-carotene, beta-carotene, neoxanthin, violaxanthin, zeaxanthin, antheraxanthin, chlorophylls a and b, and pheophytins a and b with the highest concentrations of all pigments in the skin. Chlorophyllides a and b were identified in the skin and flesh tissues only. As the fruit ripened and softened, the skin changed from green to purple/black, corresponding to changes in skin hue angle, and a concomitant increase in cyanidin 3-O-glucoside and the loss of chlorophyllide a. In flesh tissue, chroma and lightness values decreased with ripening, with no changes in hue angle. The levels of carotenoids and chlorophylls did not change significantly during ripening. As fruit ripened, the total chlorophyll level in the oil from the flesh sections remained constant but declined in the oil extracted from the skin.

Anthocyanins↗
PubMed2000

Sub-cellular localisation of the white/scarlet ABC transporter to pigment granule membranes within the compound eye of Drosophila melanogaster.

The white, scarlet, and brown genes of Drosophila melanogaster encode ABC transporters involved with the uptake and storage of metabolic precursors to the red and brown eye colour pigments. It has generally been assumed that these proteins are localised in the plasma membrane and transport precursor molecules from the heamolymph into the eye pigment cells. However, the immuno-electron microscopy experiments in this study reveal that the White and Scarlet proteins are located in the membranes of pigment granules within pigment cells and retinula cells of the compound eye. No evidence of their presence in the plasma membrane was observed. This result suggests that, rather than tranporting tryptophan into the cell across the plasma membrane, the White/Scarlet complex transports a metabolic intermediate (such as 3-hydroxy kynurenine) from the cytoplasm into the pigment granules. Other functional implications of this new finding are discussed.

ATP-Binding Cassette Transporters↗
PubMed2004

Comparison of mercury levels in various tissues of albino and pigmented mice treated with two different brands of mercury skin-lightening creams.

The use of mercury containing skin-lightening creams are becoming increasingly popular among dark-skinned women. The long-term use of certain brands may cause serious health effects over the years. In the present study, we investigated the dermal absorption of mercury and its accumulation in the tissues of albino and pigmented mice treated with two brands of mercury containing skin-lightening creams for a period of one months at different intervals. The mean +/- SD of mercury in the selected brands were: (1) Fair & Lovely (0.304 +/- 0.316 microg/g); and (2) Rose (77513.0 +/- 71063.0 microg/g). Mercury levels were measured in a total of 133 and 144 liver, kidney and brain tissue samples of albino and pigmented mice respectively by the Atomic Absorption Spectrophotometer coupled to Vapour Generator Accessory. In both strains, we found that the mercury concentration in the tissues of mice treated with Rose skin-lightening cream samples was significantly higher than those treated with Fair & Lovely skin lightening cream. Looking at the mercury concentration in the tissue samples with respect to the application of skin lightening creams at different intervals, the highest mercury concentrations were found in the tissues of albino and pigmented mice treated three times a day. On the other hand, the lowest mercury concentrations were found in the tissues of mice treated once a week. Despite the brand of skin-lightening cream that was applied, the study indicated that mercury was readily absorbed through the skin of both albino and pigmented mice as evidenced with its accumulation in the brain, kidney and liver tissues where the kidney had the highest mercury content and brain had the lowest (it P < 0.0001). Significant differences in the mercury levels were observed between the albino and pigmented mice. This emphasizes the protective role of melanin against mercury toxicity. Results of this study stresses the potential harm of these mercury containing skin-lightening creams regardless of their mercury contents especially for women who apply these creams frequently or for extended periods. Permanent nephrological or/and neurological deficits may occur if the damage is severe and diagnosis and treatment are delayed.

Albinism↗
PubMed2003

Indocyanine green angiography in pigmented paravenous retinochoroidal atrophy.

PURPOSE: To report long-term follow-up of patients with pigmented paravenous retinochoroidal atrophy (PPRCA) and to assess the involvement of the choroid and retinal pigment epithelium (RPE) in PPRCA. METHODS: Clinical features of PPRCA were studied retrospectively in four patients followed for 6-26 years. Retinal pigment epithelium and choroidal changes were analysed with fluorescein and indocyanine green (ICG) angiography. RESULTS: The two younger patients, aged 16 and 28 years and followed for 6 and 18 years, respectively, showed stationary RPE atrophy and pigmentation. Indocyanine green angiography visualized slight to modest atrophy of the choriocapillaris. The two older patients, aged 69 and 70 years and each followed for 26 years, showed slow progression of disease during follow-up. Indocyanine green angiography revealed choriocapillaris atrophy partly extending into the areas shown as hyperfluorescent in fluorescein angiography. CONCLUSION: Pigmented paravenous retinochoroidal atrophy is probably a slowly progressive disease, particularly in older patients. The choriocapillaris atrophy in this disease is more properly evaluated by ICG angiography and can be underestimated by fluorescein anigiography.

Adult↗
PubMed2002

Comparing quantitative measures of erythema, pigmentation and skin response using reflectometry.

We measured a number of pigmentation and skin response phenotypes in a sample of volunteers (n=397) living in State College, PA. The majority of this sample was composed of four groups based on stated ancestry: African-American, European-American, Hispanic and East Asian. Several measures of melanin concentration (L*, melanin index and adjusted melanin index) were estimated by diffuse reflectance spectroscopy and compared. The efficacy of these measures for assessing constitutive pigmentation and melanogenic dose-response was evaluated. Similarly, several measures of erythema (a*, erythema index and adjusted erythema index) were compared and evaluated in their efficacy in measuring erythema and erythemal dose-response. We show a high correspondence among all of the measures for the assessment of constitutive pigmentation and baseline erythema. However, our results demonstrate that evaluating melanogenic dose-response is highly dependent on the summary statistic used: while L* is a valid measure of constitutive pigmentation it is not an effective measure of melanogenic dose-response. Our results also confirm the use of a*, as it is shown to be highly correlated with the adjusted erythema index, a more advanced measure of erythema based on the apparent absorbance. Diffuse reflectance spectroscopy can be used to quantify the constitutive pigmentation, melanogenic dose-response at 7 d and erythemal dose-response at both 24 h and 7 d postexposure.

Adolescent↗
PubMed2003

1,4-benzothiazines as key intermediates in the biosynthesis of red hair pigment pheomelanins.

Following the discovery of cysteinyldopas as the early intermediates in the biogenesis of pheomelanins, the typical red hair pigments, the reactivity of the biosynthetic precursors under biomimetic conditions was extensively investigated. As a result, the early stages of pheomelanogenesis were envisaged as involving oxidative cyclization of cysteinyldopas, mainly the 5-S-isomer, to 1,4-benzothiazine (BTZ) intermediates which undergo oxidative polymerization leading eventually to the pigments. In the last decade, several aspects of the chemistry and biosynthesis of pheomelanins were re-examined. In particular, (i) transient BTZ intermediates were identified by pulse radiolytic techniques and NMR analysis; (ii) the effect of reaction conditions and additives on the rearrangement vs. redox exchange reaction paths of such intermediates were investigated in detail; (iii) the mechanism of the oxidative polymerization of BTZs was characterized by the first isolation of oligomer species, and (iv) the pigment eventually resulting from oxidation of 5-S-cysteinyldopa (CD) was directly analyzed by spectroscopic and chemical methodologies in comparison with pheomelanins isolated from human hair. These advances led eventually to an integrated picture of the biogenetic route highlighting the intervention of various chemical and enzymatic factors which affect the kinetics of the different steps and the nature of the key benzothiazine precursors. A likely biogenetic route was also postulated for the delta2,2'-bi(2H-1,4-benzothiazine) pigments, termed trichochromes, whose origin had remained an open issue since their first isolation from red human hair and avian feathers. Finally, a more detailed description of the structure of pheomelanin pigments in terms of the monomer units, their mode of linking, and postsynthetic modifications was gained.

Animals↗
PubMed1990

Tumour-associated retinal pigment epitheliopathy.

Choroidal tumours are associated with several degenerative changes in the overlying tissues, which can be called 'Tumour-Associated Retinal Pigment Epitheliopathy (TARPE)'. These changes include (i) proliferation, detachment, atrophy, and metaplasia of the retinal pigment epithelium, (ii) the accumulation of hard and soft drusen and basal laminar deposits in Bruch's membrane, (iii) disorganisation of the choriocapillaris, (iv) atrophy, cystic degeneration and detachment of the retina. The changes at the chorio-retinal interface are clinically relevant because they can exacerbate visual loss. In addition, they can be misinterpreted on ophthalmoscopy and fluorescein angiography. An amelanotic choroidal tumour may appear to be pigmented on ophthalmoscopy because of lipofuscin and melanin accumulation overlying the tumour. The hyperfluorescence associated with pigmented choroidal melanomas is more likely to be related to degenerative changes in the retinal pigment epithelium than to dye leakage from abnormal tumour vessels.

Choroid↗
PubMed2006

Evolution of danio pigment pattern development.

Pigment patterns of danio fishes are emerging as a useful system for studying the evolution of developmental mechanisms underlying adult form. Different closely related species within the genera Danio and Devario exhibit a range of pigment patterns including horizontal stripes, vertical bars, and others. In this review, I summarize recent work identifying the genetic and cellular bases for adult pigment pattern formation in the zebrafish Danio rerio, as well as studies of how these mechanisms have evolved in other danios. Together, these analyses highlight the importance of latent precursors at post-embrynoic stages, as well as interactions within and among pigment cell classes, for both pigment pattern development and evolution.

Animals↗
PubMed2001

Anka and anka pigment production.

This study was conducted to determine the time-dependent changes of solid-state fermentation of rice with Monascus purpureus to produce anka and anka pigments. Growth of the fungus occurred prior to the synthesis of anka pigments. A steady increase in the yield of pigments occurred between the 5th and 15th days. After 15 days, growth of the fungus on rice substrate ceased and the yield of yellow anka pigments remained constant; however, orange anka pigments were reduced with a decreasing rate of 3.6 mg/g anka/day.

Ascomycota↗
PubMed2006

The nature and role of pigments of marine invertebrates.

Marine animals, especially those from tropical waters, are often brilliantly coloured, and bright colouration is widespread in both sessile and non-sessile invertebrates. These spectacular natural colours are common in species inhabiting shallow waters, and appear not only in animals exposed to bright light, but also in those living in dark areas where colours are visible only with artificial illumination. Marine organisms also show variation in colour with depth and geographical location, and display great variety in colour patterning. These colour characteristics are the result of several different processes, and serve various purposes - the distribution and function of pigments seems to vary between invertebrate groups. In addition to playing an important role in how marine organisms interact, pigments may be involved in physiological processes. Although nitrogenous pigments predominate, marine organisms contain pigments belonging to all the major structural classes of natural products, as well as some that are unique to the marine environment. This review discusses the nature and significance of such pigments, the chemical and biological processes involved, the factors responsible for and affecting bright colourations, as well as their evolution and speculation as to their function.

Animals↗
PubMed2006

Modeling pigment contributions to spectral reflection of apple fruit.

A simple approach for spectral reconstruction of spectral reflection by whole apple fruit is described. It is shown that an approximation to the reflection spectrum can be obtained by making a simple assumption on the shape of the featureless scattering and using known spectral properties of the following pigment pools: (i) thylakoid-bound chlorophylls and carotenoids, (ii) cuticular/vacuolar phenolics, (iii) extrathylakoid chloroplasts/chromoplasts carotenoids, and (iv) vacuolar anthocyanins. The in vivo spectra of individual pigment pools estimated in bleaching experiments or as a difference between fruit with high and low pigment content are presented. In most cases simulations based on a linear combination of spectra proved to be effective, but fruit with high chlorophyll content necessitated the use of a non-linear model. The models succeeded in simulating reflection spectra of fruit widely differing in pigment content and composition with relative error lower than +/-4% over the visible range. The estimated relative contributions by the pigment pools into total reflection were found to be sensitive indicators of apple fruit ripening and could be useful in evaluating the light screening efficacy by flavonoids and carotenoids under stress conditions.

Fruit↗
PubMed1971

Isotopic studies of the conversion of oxophlorins and their ferrihaems into bile pigments in the rat.

1. Tritiated oxymesoporphyrins and their ferrihaems were tested as possible intermediates in the catabolism of haemoglobin. The tritiated compounds were injected into rats with biliary fistulae and the incorporation of the isotope into bile, bile pigment, urine, faeces, liver, kidney and spleen was measured. 2. alpha-Oxymesoferrihaem was extensively converted into bile pigment and specifically to the expected mesobilirubin. 3. beta-Oxymesoferrihaem was poorly converted into bile pigment and was not converted into mesobiliverdin IXbeta. The latter was independently shown to be excreted rapidly in bile. 4. The free oxyporphyrins were also poor precursors of bile pigment, and alpha-oxymesoporphyrin competed with bilirubin for excretion by the liver. 5. By analogy with the results obtained with alpha-oxymesoferrihaem it is concluded that alpha-oxyprotoferrihaem is an intermediate in the catabolism of haemoglobin, undergoing further oxidation to bile pigment under the catalysis of an enzyme of definite specificity.

Animals↗
PubMed1980

Metabolism of hepatic haem and 'green pigments' in rats given 2-allyl-2-isopropylacetamide and ferric citrate. A new model for hepatic haem turnover.

We have studied effects of single doses of 2-allyl-2-isopropylacetamide and ferric citrate on hepatic haem turnover in rats. Haem was pre-labelled by intraperitoneal administration of 5-amino-[4-(14)C]laevulinate 4h before other treatments. Computer-assisted analysis of the haem decay curve showed that at least two exponential components were involved implying two haem pools. In control rats the size of the rapidly-turning-over pool was 38% of the total. Treatment with 2-allyl-2-isopropylacetamide alone resulted in a 2.3-fold increase in the fractional size of this pool. Treatment with ferric citrate alone increased the size of this pool 1.8-fold; treatment with both agents together had no measurable effect beyond that produced by 2-allyl-2-isopropylacetamide. The apparent rate constant for disappearance of labelled haem from the first pool was not affected by treatment with 2-allyl-2-isopropylacetamide or ferric citrate, indicating that these treatments affect hepatic haem turnover primarily by altering the distribution of haem synthesized in the liver. The increased haem degradation after treatment with 2-allyl-2-isopropylacetamide alone was associated with the accumulation of ;green pigments' in the liver. These pigments were detectable 1.5h after drug treatment; their total amount increased steadily for 28h and then declined. Despite this increase in amount, radioactivity of the ;green pigment' fraction fell rapidly in a biphasic fashion. Some of the radioactivity that initially was found in the ;green pigment' fraction was later found in an aqueous fraction, not extractable by acidic ethyl acetate. Rats given ferric citrate together with 2-allyl-2-isopropylacetamide accumulated less ;green pigments'.

Acetamides↗
PubMed2002

Pigmented neuroendocrine tumor of the lung, showing neuromelanin.

A pigmented neuroendocrine tumor was discovered incidentally in a 62-year-old woman through examination by chest computed tomography. The tumor was located in the left lower lobe, S6, of the lung and was 8 mm in diameter. The preoperative percutaneous needle biopsy was interpreted as a tumor suggestive of small cell carcinoma. Histological examination of the operated lobectomy material revealed that the nodule was a neuroendocrine tumor consisting of mainly spindle-shaped cells and several pigmented cells. Electron microscopy showed several dense-core neurosecretory-type granules in tumor cells, as well as abundant, pleomorphic electron-dense granules in pigmented cells much larger in size and most consistent with lipofuscin or neuromelanin. No melanosomes or premelanosomes were identified. Considering the result of ultrastructural and histochemical studies, the pigment was considered most likely neuromelanin. Neuromelanin is found in neurons of substantia nigra and locus ceruleus, and sympathetic ganglion cells. It is rarely found in neuroendocrine tumors and we review the available reports regarding pigmented carcinoid tumor.

Biomarkers, Tumor↗
PubMed2001

Transforming growth factor-beta1 induces alpha-smooth muscle actin expression and fibronectin synthesis in cultured human retinal pigment epithelial cells.

BACKGROUND: Proliferative vitreoretinopathy is a serious complication of retinal detachment, yet its pathogenesis is not fully understood. Retinal pigment epithelial cells and glial cells are found in the fibrous membranes in proliferative vitreoretinopathy. Many cytokines are involved in the pathology. Transforming growth factor (TGF)-beta, a cytokine found in serum, has been shown to be an important factor regulating the synthesis of fibrous extracellular matrix in proliferative vitreoretinopathy. METHODS: Cultured human retinal pigment epithelial cells were used in the experiments. The effects of TGF-beta1 on phenotype and function in retinal pigment epithelial cells were recorded as changes in the expression of alpha-smooth muscle actin and fibronectin synthesis using immunohistochemistry and enzyme-linked immunosorbent assay, respectively. RESULTS: TGF-beta1 induced the expression of alpha-smooth muscle actin (P < 0.0001, n = 3), and significantly increased the synthesis of fibronectin by cultured human retinal pigment epithelial cells (P < 0.01, n = 4). CONCLUSIONS: Elevated levels of TGF-beta1 in proliferative vitreoretinopathy may contribute to phenotype changes in retinal pigment epithelial cells leading to matrix deposition and contraction. Since the elevated levels of TGF-beta1 may emanate from a number of diverse sources in proliferative vitreoretinopathy, developing an antagonist to TGF-beta1 may offer an approach to the treatment of proliferative vitreoretinopathy.

Actins↗