Echinochrome A

Echinochrome A
Names
	Preferred IUPAC name 6-ethyl-2,3,5,7,8-pentahydroxynaphthalene-1,4-dione
	Other names 7-ethyl-2,3,5,6,8-pentahydroxy-1,4-nafphtoquinone; 6-Ethyl-2,7-trihydroxynaphthazarin; 6-ethyl-2,3,5,7,8-pentahydroxy-2-Ethyl-3,5,6,7,8-pentahydroxy-[1,4]naphthoquinone
Identifiers
CAS Number	517-82-8;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL155722;
ChemSpider	13474075;
PubChem CID	135457951;
UNII	J4L83T8MZ5;
CompTox Dashboard (EPA)	DTXSID801031488 ;
	InChI InChI=1S/C12H10O7/c1-2-3-6(13)4-5(8(15)7(3)14)10(17)12(19)11(18)9(4)16/h13-15,18-19H,2H2,1H3 Key: DNRFNICCPHGYAX-UHFFFAOYSA-N;
	SMILES CCC1=C(C2=C(C(=C1O)O)C(=O)C(=C(C2=O)O)O)O;
Properties
Chemical formula	C12H10O7
Molar mass	266.205 g·mol−1
Appearance	Dark red crystalline powder
Melting point	−219 to 221.5 °C (−362.2 to 430.7 °F; 54.1 to 494.6 K)
Solubility in water	Practically insoluble
Solubility	Moderately soluble in ethanol; very slightly soluble in chloroform
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Echinochrome A (7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone) is a polyhydroxylated 1,4-naphthoquinone,^[1] a type of pigments commonly found in sea urchin shell ("test"), spine, gonads, coelomic fluid, and eggs, of sea urchin.^[2] These type of pigments are commonly known as spinochromes and are natural marine phenolic compounds with potential pharmacological effects and modes of action.^[3]

First extracted from the sea urchin Scaphechinus mirabilis, it is the active substance of histochrome and Echino-A. Histochrome is used for ophthalmic diseases and ischemic heart disease.^{[medical citation needed]} Echino-A has been used in nutraceutical form to diminish glucose levels, cholesterol and tryglicerides.^{[medical citation needed]} The properties and the absence of adverse effects of echinochrome A as an antioxidant has made it the subject of scientific and clinical studies for more than 30 years.^[4]^[5]^[6]

The several hydroxyl groups have the ability to diminish reactive oxygen species (ROS) in cells, preventing redox imbalance. Echinochrome A has been found to target ophtalmologic, cardiovascular, cerebrovascular, inflammatory and metabolic diseases through its biological functions by targeting specific molecular signals. The regulation effects produced by echinochrome A in the cells makes this molecule a candidate to improve health.^[6]^[7] Sea urchins are known for their putative health properties for centuries, for example in the Materia medica of the Ming Dynasty authored by Li Zhongli in 1647.^[8]

References

^ CID 135457951 from PubChem Retrieved April 13, 2022
^ Anderson, H.A.; Mathieson, J.W.; Thomson, R.H. (January 1969). "Distribution of spinochrome pigments in echinoids". Comparative Biochemistry and Physiology. 28 (1): 333–345. doi:10.1016/0010-406X(69)91347-4. PMID 5777380.
^ Jeong, Seung; Kim, Hyoung; Song, In-Sung; Lee, Seon; Ko, Kyung; Rhee, Byoung; Kim, Nari; Mishchenko, Natalia; Fedoryev, Sergey; Stonik, Valentin; Han, Jin (13 May 2014). "Echinochrome A Protects Mitochondrial Function in Cardiomyocytes against Cardiotoxic Drugs". Marine Drugs. 12 (5): 2922–2936. doi:10.3390/md12052922. PMC 4052324. PMID 24828295.
^ Hou, Yakun; Vasileva, Elena A.; Carne, Alan; McConnell, Michelle; El-Din A. Bekhit, Alaa; Mishchenko, Natalia P. (2018). "Naphthoquinones of the spinochrome class: occurrence, isolation, biosynthesis and biomedical applications". RSC Advances. 8 (57): 32637–32650. Bibcode:2018RSCAd...832637H. doi:10.1039/C8RA04777D. PMC 9086473. PMID 35547692. S2CID 105576241.
^ Rubilar, Tamara; Barbieri, Elena S.; Gazquez, Ayelén; Avaro, Marisa (May 2021). "Sea Urchin Pigments: Echinochrome A and Its Potential Implication in the Cytokine Storm Syndrome". Marine Drugs. 19 (5): 267. doi:10.3390/md19050267. PMC 8151293. PMID 34064550.
^ ^a ^b Kim, Hyoung Kyu; Vasileva, Elena A.; Mishchenko, Natalia P.; Fedoreyev, Sergey A.; Han, Jin (August 2021). "Multifaceted Clinical Effects of Echinochrome". Marine Drugs. 19 (8): 412. doi:10.3390/md19080412. PMC 8400489. PMID 34436251.
^ Artyukov, Aleksandr A.; Zelepuga, Elena A.; Bogdanovich, Larisa N.; Lupach, Natalia M.; Novikov, Vyacheslav L.; Rutckova, Tatyana A.; Kozlovskaya, Emma P. (May 2020). "Marine Polyhydroxynaphthoquinone, Echinochrome A: Prevention of Atherosclerotic Inflammation and Probable Molecular Targets". Journal of Clinical Medicine. 9 (5): 1494. doi:10.3390/jcm9051494. PMC 7291202. PMID 32429179.
^ Barbieri, Elena Susana; Rubilar, Tamara; Gázquez, Ayelén; Avaro, Marisa; Seiler, Erina Noé; Vera-Piombo, Mercedes; Gittardi, Agustín; Chaar, Florencia; Fernandez, Jimena Pía; Sepulveda, Lucas (29 June 2020). "Sea Urchin Pigments as Potential Therapeutic Agents Against the Spike Protein of SARS-CoV-2 Based on in Silico Analysis". doi:10.26434/chemrxiv.12568595.v1. hdl:11336/109300. S2CID 225845754. {{cite journal}}: Cite journal requires |journal= (help) This content is a preprint and has not been peer-reviewed

[1] CID 135457951 from PubChem Retrieved April 13, 2022

[2] Anderson, H.A.; Mathieson, J.W.; Thomson, R.H. (January 1969). "Distribution of spinochrome pigments in echinoids". Comparative Biochemistry and Physiology. 28 (1): 333–345. doi:10.1016/0010-406X(69)91347-4. PMID 5777380.

[3] Jeong, Seung; Kim, Hyoung; Song, In-Sung; Lee, Seon; Ko, Kyung; Rhee, Byoung; Kim, Nari; Mishchenko, Natalia; Fedoryev, Sergey; Stonik, Valentin; Han, Jin (13 May 2014). "Echinochrome A Protects Mitochondrial Function in Cardiomyocytes against Cardiotoxic Drugs". Marine Drugs. 12 (5): 2922–2936. doi:10.3390/md12052922. PMC 4052324. PMID 24828295.

[4] Hou, Yakun; Vasileva, Elena A.; Carne, Alan; McConnell, Michelle; El-Din A. Bekhit, Alaa; Mishchenko, Natalia P. (2018). "Naphthoquinones of the spinochrome class: occurrence, isolation, biosynthesis and biomedical applications". RSC Advances. 8 (57): 32637–32650. Bibcode:2018RSCAd...832637H. doi:10.1039/C8RA04777D. PMC 9086473. PMID 35547692. S2CID 105576241.

[5] Rubilar, Tamara; Barbieri, Elena S.; Gazquez, Ayelén; Avaro, Marisa (May 2021). "Sea Urchin Pigments: Echinochrome A and Its Potential Implication in the Cytokine Storm Syndrome". Marine Drugs. 19 (5): 267. doi:10.3390/md19050267. PMC 8151293. PMID 34064550.

[kim-6] Kim, Hyoung Kyu; Vasileva, Elena A.; Mishchenko, Natalia P.; Fedoreyev, Sergey A.; Han, Jin (August 2021). "Multifaceted Clinical Effects of Echinochrome". Marine Drugs. 19 (8): 412. doi:10.3390/md19080412. PMC 8400489. PMID 34436251.

[7] Artyukov, Aleksandr A.; Zelepuga, Elena A.; Bogdanovich, Larisa N.; Lupach, Natalia M.; Novikov, Vyacheslav L.; Rutckova, Tatyana A.; Kozlovskaya, Emma P. (May 2020). "Marine Polyhydroxynaphthoquinone, Echinochrome A: Prevention of Atherosclerotic Inflammation and Probable Molecular Targets". Journal of Clinical Medicine. 9 (5): 1494. doi:10.3390/jcm9051494. PMC 7291202. PMID 32429179.

[8] Barbieri, Elena Susana; Rubilar, Tamara; Gázquez, Ayelén; Avaro, Marisa; Seiler, Erina Noé; Vera-Piombo, Mercedes; Gittardi, Agustín; Chaar, Florencia; Fernandez, Jimena Pía; Sepulveda, Lucas (29 June 2020). "Sea Urchin Pigments as Potential Therapeutic Agents Against the Spike Protein of SARS-CoV-2 Based on in Silico Analysis". doi:10.26434/chemrxiv.12568595.v1. hdl:11336/109300. S2CID 225845754. {{cite journal}}: Cite journal requires |journal= (help) This content is a preprint and has not been peer-reviewed

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