Retrochalcone

A retrochalcone is a chalcone-like compound in which the normally present hydroxy groups at the 2' and 6' positions are missing. The retrochalcone structure has a propenal bridge connected to two benzene rings at each end. The ring closest to the oxygen, is labelled with primed numbers, normally with a hydroxy group at the 4' position. This is the A ring. The ring closest to the double bond is numbered with simple digits starting from 1 at the bridge connection. This is the B ring. There is usually a hydroxy group at the 4 position. The retrochalcones are found naturally where they are derivatives of flavones.[1] Retrochalcones can be classed as minor flavonoids.[2]

One example derivative is echinatin.[1] It has systematic name (E)-1-(4-hydroxyphenol)-3-(3-methoxy-4-hydroxyphenol)-2-propen-1-one, or derived name 4',4-dihydroxy-2-methoxychalcone and was found in Glycyrrhiza echinata.

List
  • Licochalcone A (E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one[3]
  • Licochalcone B[3]
  • Licochalcone C[3]
  • Licochalcone D[3]
  • Licochalcone E (E)-3-[4-hydroxy-2-methoxy-5-[(2S)-3-methylbut-3-en-2-yl]phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one[4]
  • tepanone ((2E)-1-phenyl-3-(2´-hydroxy-3´,4´,6´-trimethoxyphenyl)prop-2-enone[5]

References
  1. Cazarolli, Luisa Helena; Kappel, Virginia Demarchi; Zanatta, Ana Paula; Suzuki, Daniela Ota Hisayasu; Yunes, Rosendo Augusto; Nunes, Ricardo José; Pizzolatti, Moacir Geraldo; Silva, Fátima Regina Mena Barreto (2013). Studies in Natural Products Chemistry: Chapter 2. Natural and Synthetic Chalcones: Tools for the Study of Targets of Action—Insulin Secretagogue or Insulin Mimetic?. Elsevier Inc. Chapters. ISBN 9780128084823.
  2. Marais, J.P.J.; Deavours, B.; Dixon, R.A; Ferreira, D. (2006). Grotewold, Erich (ed.). The Science of Flavonoids (PDF). Springer. p. 4. ISBN 0-387-28821-X.
  3. Bidlack, Wayne R.; Omaye, Stanley T.; Meskin, Mark S.; Topham, Debra K. W. (2000). Phytochemicals as Bioactive Agents. CRC Press. p. 115. ISBN 9781566767880.
  4. Zhou, T; Deng, X; Qiu, J (June 2012). "Antimicrobial activity of licochalcone E against Staphylococcus aureus and its impact on the production of staphylococcal alpha-toxin". Journal of Microbiology and Biotechnology. 22 (6): 800–5. doi:10.4014/jmb.1112.12020. PMID 22573157.
  5. Hasliza, Yusof; Din, Laily B.; Yaacob, Wan A.; Ibrahim, Nazlina; Yamin, Bohari Mohd; Latiff, A. (August 2015). "The chemical constituents of Ellipeia cuneifolia and their antibacterial activity". Sains Malaysiana. 44 (8): 1125–1128. doi:10.17576/jsm-2015-4408-07.
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