Chemistry:Rapanone

From HandWiki

Rapanone is an organic compound and natural product. It is a tridecyl side chain derivative of 2,5-dihydroxy-1,4-benzoquinone with the chemical formula C19H30O4.

Occurrence

It occurs in various plant species including Aconitum lamarckii, Aegiceras corniculatum, Embelia ribes, Heliotropium indicum, and several Ardisia species.[1][2] It also occurs in fungi including Irpex lacteus.[1]

Synthesis

Rapanone can be synthesized by the alkylation of 2,5-dihydroxy-1,4-benzoquinone with the peroxide of myristic acid.[3]

Pharmacology

Rapanone derivatives and related quinonoids are being researched for their potential anticancer properties, although their mechanism is unclear.[4][5][6][7] It is also classified as an antiparasitic agent.[8] Some studies claim iron chelating and free radical scavenging properties in rapanone and its derivatives.[9][10]

References

  1. ↑ 1.0 1.1 Cite error: Invalid <ref> tag; no text was provided for refs named PubChem
  2. ↑ Kobayashi, Hideka; de Mejía, Elvira (2005-01-15). "The genus Ardisia: a novel source of health-promoting compounds and phytopharmaceuticals". Journal of Ethnopharmacology 96 (3): 347–354. doi:10.1016/j.jep.2004.09.037. ISSN 0378-8741. Bibcode: 2005JEthn..96..347K. https://www.sciencedirect.com/science/article/pii/S0378874104004775. 
  3. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named Fieser
  4. ↑ Sarkar, Pritam; Ahnaf, Tasfiya Rufaidah; Rouf, Razina; Shilpi, Jamil Ahmad; Uddin, Shaikh Jamal (2024). "A Review on Bioactive Phytochemical Constituents and Pharmacological Activities of Aegiceras corniculatum: A Pharmaceutically Important Mangrove Plant" (in en). Journal of Chemistry 2024 (1). doi:10.1155/2024/9992568. ISSN 2090-9071. 
  5. ↑ Ying, Hua-Zhong; Yu, Chen-Huan; Chen, Hao-Kun; Zhang, Huan-Huan; Fang, Jie; Wu, Fang; Yu, Wen-Ying (2020). "Quinonoids: Therapeutic Potential for Lung Cancer Treatment" (in en). BioMed Research International 2020 (1). doi:10.1155/2020/2460565. ISSN 2314-6141. PMID 32337232. 
  6. ↑ Sarkar, Chandan; Mondal, Milon; Khanom, Bilkis; Hossain, Md. Monir; Hossain, Md. Solayman; Sureda, Antoni; Islam, Muhammad Torequl; Martorell, Miquel et al. (2021). "Heliotropium indicum L.: From Farm to a Source of Bioactive Compounds with Therapeutic Activity" (in en). Evidence-Based Complementary and Alternative Medicine 2021 (1). doi:10.1155/2021/9965481. ISSN 1741-4288. PMID 34158818. 
  7. ↑ Pardo Andreu, Gilberto L.; Reis, Felipe Zuccolotto Dos; González-Durruthy, Michael; Hernández, René Delgado; D'Vries, Richard F.; Vanden Berghe, Wim; Alberici, Luciane C. (2020-03-01). "Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death". Toxicology in Vitro 63. doi:10.1016/j.tiv.2019.104737. ISSN 0887-2333. PMID 31756542. Bibcode: 2020ToxVi..6304737P. https://www.sciencedirect.com/science/article/pii/S0887233319306812. 
  8. ↑ "Rapanone MeSH Supplementary Concept Data 2026". https://meshb.nlm.nih.gov/record/ui?ui=C054611. 
  9. ↑ de la Vega-Hernández, Karen; Antuch, Manuel; Cuesta-Rubio, Osmany; Núñez-Figueredo, Yanier; Pardo-Andreu, Gilberto L (2017-05-01). "Discerning the antioxidant mechanism of rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities". Journal of Inorganic Biochemistry 170: 134–147. doi:10.1016/j.jinorgbio.2017.02.019. ISSN 0162-0134. PMID 28237732. https://www.sciencedirect.com/science/article/pii/S016201341730106X. 
  10. ↑ Mariyappan, Vaithiyalingam; Munuswamy-Ramanujam, Ganesh; Ramasamy, Mohankumar (2024-02-21). "Synthesis of novel rapanone derivatives via organocatalytic reductive C-alkylation: biological evaluation of antioxidant properties, in vivo zebrafish embryo toxicity, and docking studies" (in en). RSC Medicinal Chemistry 15 (2): 623–635. doi:10.1039/D3MD00564J. ISSN 2632-8682. PMID 38389875. 



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