Spinochrome E (also called 2,3,5,6,7,8-hexahydroxy-1,4-naphthalenedione or hexahydroxynaphthoquinone) is a polyhydroxylated 1,4-naphthoquinone pigment found in sea urchin

shell Shell may refer to: Architecture and design * Shell (structure), a thin structure ** Concrete shell, a thin shell of concrete, usually with no interior columns or exterior buttresses Science Biology * Seashell, a hard outer layer of a marine ani ...

("test"),

spine Spine or spinal may refer to: Science Biology * Spinal column, also known as the backbone * Dendritic spine, a small membranous protrusion from a neuron's dendrite * Thorns, spines, and prickles, needle-like structures in plants * Spine (zoology), ...

, gonads, coelomic fluid, and eggs, of

sea urchin Sea urchins or urchins () are echinoderms in the class (biology), class Echinoidea. About 950 species live on the seabed, inhabiting all oceans and depth zones from the intertidal zone to deep seas of . They typically have a globular body cove ...

commonly known as spinochromes. These natural phenolic compounds are quinones with potential pharmacological properties. The several hydroxyl groups are appropriate for free-radical scavenging, which diminishes ROS and prevents redox imbalance. Mechanisms are described such as scavenging of

reactive oxygen species In chemistry and biology, reactive oxygen species (ROS) are highly Reactivity (chemistry), reactive chemicals formed from diatomic oxygen (), water, and hydrogen peroxide. Some prominent ROS are hydroperoxide (H2O2), superoxide (O2−), hydroxyl ...

(ROS), interaction with lipid peroxide radicals, chelation of metal ions, inhibition of lipid peroxidation and regulation of the cell redox potential. The chemical formula of spinochrome E, , indicates that it has one extra hydroxyl group relative to echinochrome A and it is formally derived from

naphthoquinone Naphthoquinones constitute a class of organic compounds structurally related to naphthalene. Two isomers are common for the parent naphthoquinones: * 1,2-Naphthoquinone * 1,4-Naphthoquinone Natural products * Alkannin * Hexahydroxy-1,4-nap ...

(1,4-naphtalenedione) through replacement of all six

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

atoms by

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

(OH) groups. The numerical prefixes "2,3,5,6,7,8" are superfluous, since there is no other hexahydroxy derivative of 1,4-naphthoquinone. Spinochrome from sea urchins, in oriental culture, are known for putative health benefits. The sea urchin appears in the "Materia medica" of the Ming Dynasty author by Li Zhongli in 1647 and the benefits cited are for the heart, bones, blood and also it counteracts impotence. Today it is known the benefits for the health of these compounds. The compound can be produced by condensation of 3,4,5,6-tetramethoxyphthalaldehyde with

glyoxal Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...

References

* H. A. Anderson and R. H. Thomson (1966), ''Naturally Occurring Quinones. Part VIP Synthesis of Spinochrome E''. J. Chem. Soc. series C (Organic), pages 426-428. * T. W. Goodwin, E. Lederer and L. Musajo (1951), ''The nomenclature of the spinochromes of sea urchins''. Cellular and Molecular Life Sciences, Volume 7, Number 10, pages 375-376. * Shikov, A.N.; Pozharitskaya, O.N.; Krishtopina, A.S.; Makarov, V.G. Naphthoquinone pigments from sea urchins: Chemistry and pharmacology. Phytochem. Rev. 2018, 17, 509–534. * Brasseur, L.; Hennebert, E.; Fievez, L.; Caulier, G.; Bureau, F.; Tafforeau, L.; Flammang, P.; Gerbaux, P.; Eeckhaut, I. The Roles of Spinochromes in Four Shallow Water Tropical Sea Urchins and Their Potential as Bioactive Pharmacological Agents. Mar. Drugs 2017, 15, 179. Diversity of Polyhydroxynaphthoquinone Pigments in North Pacific Sea Urchins. Chem. Biodivers. 2017, 14, e1700182. * Nishibori, K. Isolation of Echinochrome A from the Spines of the Sea Urchin, Diadema setosum (Leske). Nature 1959, 184, 1234. * Martínez, M.J.A.; Benito, P.B. Biological Activity of Quinones. In Studies in Natural Products Chemistry; Elsevier BV: Amsterdam, the Netherlands, 2005; Volume 30, pp. 303–366. * Zhou, D.-Y.; Qin, L.; Zhu, B.-W.; Wang, X.-D.; Tan, H.; Yang, J.-F.; Li, D.-M.; Dong, X.-P.; Wu, H.-T.; Sun, L.-M.; et al. Extraction and antioxidant property of polyhydroxylated naphthoquinone pigments from spines of purple sea urchin Strongylocentrotus nudus. Food Chem. 2011, 129, 1591–1597. * Hou, Y., Vasileva, E. A., Carne, A., McConnell, M., Bekhit, A. E. D. A., & Mishchenko, N. P. (2018). Naphthoquinones of the spinochrome class: Occurrence, isolation, biosynthesis and biomedical applications. RSC advances, 8(57), 32637-32650. * Rubilar, T., Barbieri, E. S., Gazquez, A., & Avaro, M. (2021). Sea Urchin Pigments: Echinochrome A and Its Potential Implication in the Cytokine Storm Syndrome. Marine Drugs, 19(5), 267. * Kim, H.K., Vasileva, E.A., Mishchenko, N.P., Fedoreyev, S.E. and Han, J. (2021) Multifaceted Clinical Effects of Echinochrome. Marine Drugs, 19, 412. {{doi, 10.3390/md19080412, doi-access=free 1,4-Naphthoquinones Hydroxynaphthoquinones

See also

References