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Elucidation of the hierarchical structure of natural eumelanins

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Abstract
Eumelanin is one of the most ubiquitous pigments in living organisms and plays an important role in coloration and UV protection. Because eumelanin is highly cross-linked and insoluble in solvents, the chemical structure is still not completely known. In this study, we used atomic force microscopy, X-ray photoelectron spectroscopy and solid-state nuclear magnetic resonance (NMR) to compare intact eumelanosomes (pigment granules mostly made of eumelanin) from four phylogentically distant species: cuttlefish (Sepia officinalis) inks, black fish crow (Corvus ossifragus) feathers, iridescent wild turkey (Melleagris gallopavo) feathers and black human hair. We found that eumelanosomes from all four species are composed of subunit nanoparticles with a length of 10-60 nm, consistent with earlier observations in eumelanosomes from the sepia ink and human hair. The solid-state NMR results indicate the presence of quinone methide tautomers in all four eumelanins. We also found clear differences in the UV absorbance, the ratio of 5,6-dihydroxyindole-2-carboxylic acid/5,6-dihydroxyindole and protonated aryl carbon ratios in sepia eumelanin relative to the other three. This comparison of natural eumelanin across a phylogenetically broad group of organisms provides insights into the change in the eumelanin structure over the evolutionary history and enables the production of synthetic eumelanin with properties that are similar to natural eumelanin.
Keywords
melanin, eumelanin, hierarchical structure, SOLID-STATE NMR, NUCLEAR-MAGNETIC-RESONANCE, HUMAN HAIR MELANIN, BUILDING-BLOCKS, SEPIA MELANIN, PHYSICAL-PROPERTIES, MOLECULAR-STRUCTURE, CHEMICAL-PROPERTIES, FREE ACID, POLYDOPAMINE

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Citation

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MLA
Xiao, Ming et al. “Elucidation of the Hierarchical Structure of Natural Eumelanins.” JOURNAL OF THE ROYAL SOCIETY INTERFACE 15.140 (2018): n. pag. Print.
APA
Xiao, M., Chen, W., Li, W., Zhao, J., Hong, Y., Nishiyama, Y., Miyoshi, T., et al. (2018). Elucidation of the hierarchical structure of natural eumelanins. JOURNAL OF THE ROYAL SOCIETY INTERFACE, 15(140).
Chicago author-date
Xiao, Ming, Wei Chen, Weiyao Li, Jiuzhou Zhao, You-lee Hong, Yusuke Nishiyama, Toshikazu Miyoshi, Matthew Shawkey, and Ali Dhinojwala. 2018. “Elucidation of the Hierarchical Structure of Natural Eumelanins.” Journal of the Royal Society Interface 15 (140).
Chicago author-date (all authors)
Xiao, Ming, Wei Chen, Weiyao Li, Jiuzhou Zhao, You-lee Hong, Yusuke Nishiyama, Toshikazu Miyoshi, Matthew Shawkey, and Ali Dhinojwala. 2018. “Elucidation of the Hierarchical Structure of Natural Eumelanins.” Journal of the Royal Society Interface 15 (140).
Vancouver
1.
Xiao M, Chen W, Li W, Zhao J, Hong Y, Nishiyama Y, et al. Elucidation of the hierarchical structure of natural eumelanins. JOURNAL OF THE ROYAL SOCIETY INTERFACE. 2018;15(140).
IEEE
[1]
M. Xiao et al., “Elucidation of the hierarchical structure of natural eumelanins,” JOURNAL OF THE ROYAL SOCIETY INTERFACE, vol. 15, no. 140, 2018.
@article{8560168,
  abstract     = {Eumelanin is one of the most ubiquitous pigments in living organisms and plays an important role in coloration and UV protection. Because eumelanin is highly cross-linked and insoluble in solvents, the chemical structure is still not completely known. In this study, we used atomic force microscopy, X-ray photoelectron spectroscopy and solid-state nuclear magnetic resonance (NMR) to compare intact eumelanosomes (pigment granules mostly made of eumelanin) from four phylogentically distant species: cuttlefish (Sepia officinalis) inks, black fish crow (Corvus ossifragus) feathers, iridescent wild turkey (Melleagris gallopavo) feathers and black human hair. We found that eumelanosomes from all four species are composed of subunit nanoparticles with a length of 10-60 nm, consistent with earlier observations in eumelanosomes from the sepia ink and human hair. The solid-state NMR results indicate the presence of quinone methide tautomers in all four eumelanins. We also found clear differences in the UV absorbance, the ratio of 5,6-dihydroxyindole-2-carboxylic acid/5,6-dihydroxyindole and protonated aryl carbon ratios in sepia eumelanin relative to the other three. This comparison of natural eumelanin across a phylogenetically broad group of organisms provides insights into the change in the eumelanin structure over the evolutionary history and enables the production of synthetic eumelanin with properties that are similar to natural eumelanin.},
  articleno    = {20180045},
  author       = {Xiao, Ming and Chen, Wei and Li, Weiyao and Zhao, Jiuzhou and Hong, You-lee and Nishiyama, Yusuke and Miyoshi, Toshikazu and Shawkey, Matthew and Dhinojwala, Ali},
  issn         = {1742-5689},
  journal      = {JOURNAL OF THE ROYAL SOCIETY INTERFACE},
  keywords     = {melanin,eumelanin,hierarchical structure,SOLID-STATE NMR,NUCLEAR-MAGNETIC-RESONANCE,HUMAN HAIR MELANIN,BUILDING-BLOCKS,SEPIA MELANIN,PHYSICAL-PROPERTIES,MOLECULAR-STRUCTURE,CHEMICAL-PROPERTIES,FREE ACID,POLYDOPAMINE},
  language     = {eng},
  number       = {140},
  pages        = {10},
  title        = {Elucidation of the hierarchical structure of natural eumelanins},
  url          = {http://dx.doi.org/10.1098/rsif.2018.0045},
  volume       = {15},
  year         = {2018},
}

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