Echinochrome A

Last updated
Echinochrome A
Skeletal formula Echinochrome A.svg
Skeletal formula
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
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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
  • CCC1=C(C2=C(C(=C1O)O)C(=O)C(=C(C2=O)O)O)O
Properties
C12H10O7
Molar mass 266.205 g·mol−1
AppearanceDark red crystalline powder
Melting point −219 to 221.5 °C (−362.2 to 430.7 °F; 54.1 to 494.6 K)
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).

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 types 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 [4] 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. [5] [6] [7]

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 ophthalmologic, 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. [7] [8] 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. [9]

References

  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. ↑ Mishchenko, Natalia P; Fedoreyev, Sergey A; Bagirova, V L: "Histochrome: a New Original Domestic Drug" in Pharmaceutical Chemistry Journal 37(1):48-52, January 2003. doi:10.1023/A:1023659331010
  5. ↑ 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.
  6. ↑ 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.
  7. 1 2 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.
  8. ↑ 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.
  9. ↑ 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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