Chemistry:Ardisiaquinone

From HandWiki
Ardisiaquinones
Identifiers
3D model (JSmol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Ardisiaquinones are a group of closely related chemical compounds found in plants in the genus Ardisia. The first examples, ardisiaquinones A-C, were isolated in 1968 from Ardisia sieboldii.[1] In 1995, ardisiaquinones D, E, and F were discovered, also from Ardisia sieboldii.[2] In 2001, ardisiaquinones G, H and I were isolated from Ardisia teysmanniana.[3]

Chemically, the ardisiaquinones consist of two variably-substituted 1,4-benzoquinone units connected by a long alkyl or alkenyl chain.[1]

Research

Ardisiaquinones are of research interest because they possess 5-lipoxygenase (5-LOX) inhibitor activity and 5-LOX has clinical relevance in inflammation.[4] For example, ardisiaquinone A protects against liver injury in an animal model of ischemia-reperfusion injury.[5] Likewise, ardisiaquinone G has also shown 5-LOX inhibition.[4] Ardisiaquinone A has also been shown to have an antiallergic effect in an animal model.[6] Other ardisiaquinones have shown antiproliferative and antimicrobial effects in vitro.[7]

Laboratory syntheses of ardisiaquinones A and B have been reported.[8][9]

Chemical structures

  • Ardisiaquinone A

  • Ardisiaquinone B

  • Ardisiaquinone C

  • Ardisiaquinone D

  • Ardisiaquinone E

  • Ardisiaquinone F

  • Ardisiaquinone G

References

  1. ↑ 1.0 1.1 Ogawa, H.; Sakaki, S.; Yoshihira, K.; Natori, S. (1968). "The structures of ardisiaquinones A, B and C, bis(benzoquinonyl)-olefine derivatives from miquel". Tetrahedron Letters 9 (11): 1387–1392. doi:10.1016/S0040-4039(01)98959-2. 
  2. ↑ Fukuyama, Yoshiyasu; Kiriyama, Yuuko; Kodama, Mitsuaki; Iwaki, Hideyuki; Hosozawa, Shigeki; Aki, Shinji; Matsui, Kuniaki (1995). "Naturally Occurring 5-Lipoxygenase Inhibitors. VI. Structures of Ardisiaquinones D, e, and F from Ardisia sieboldii". Chemical and Pharmaceutical Bulletin 43 (8): 1391–1394. doi:10.1248/cpb.43.1391. PMID 7553985. 
  3. ↑ Yang, Lay-Kien; Khoo-Beattie, Corinne; Goh, Kay-Lin; Chng, Bee-Lee; Yoganathan, K.; Lai, Yee-Hing; Butler, Mark S. (2001). "Ardisiaquinones from Ardisia teysmanniana". Phytochemistry 58 (8): 1235–1238. doi:10.1016/s0031-9422(01)00317-x. PMID 11738414. 
  4. ↑ 4.0 4.1 Narayanaswamy, Radhakrishnan; Veeraragavan, Vijayakumar (2020). "Natural products as antiinflammatory agents". Bioactive Natural Products. Studies in Natural Products Chemistry. 67. pp. 269–306. doi:10.1016/B978-0-12-819483-6.00008-4. ISBN 9780128194836. 
  5. ↑ Matsui, Nobuaki; Fukuishi, Nobuyuki; Fukuyama, Yoshiyasu; Yasui, Yumiko; Akagi, Masaaki (2005). "Protective Effect of the 5-Lipoxygenase Inhibitor Ardisiaquinone a on Hepatic Ischemia-Reperfusion Injury in Rats". Planta Medica 71 (8): 717–720. doi:10.1055/s-2005-871252. PMID 16142634. 
  6. ↑ Fukuishi, N.; Takada, T.; Fukuyama, Y.; Akagi, M. (2001). "Antiallergic effect of ardisiaquinone A, a potent 5-lipoxygenase inhibitor". Phytomedicine 8 (6): 460–464. doi:10.1078/s0944-7113(04)70065-3. PMID 11824521. 
  7. ↑ Paul, Dzoyem J.; Laure, Ndontsa B.; Guru, Santosh K.; Khan, Inshad A.; Ajit, Saxena K.; Vishwakarma, Ram A.; Pierre, Tane (2014). "Antiproliferative and antimicrobial activities of alkylbenzoquinone derivatives from Ardisia kivuensis". Pharmaceutical Biology 52 (3): 392–397. doi:10.3109/13880209.2013.837076. PMID 24192208. 
  8. ↑ Fukuyama, Yoshiyasu; Kiriyama, Yuuko; Kodama, Mitsuaki; Iwaki, Hideyuki; Hosozawa, Shigeki; Aki, Shinji; Matsui, Kuniaki (1994). "Total Synthesis of Ardisiaquinone A, a Potent 5-Lipoxygenase Inhibitor, Isolated from Ardisia sieboldii, and Degree of 5-Lipoxygenase Inhibitory Activity of Its Derivatives". Chemical and Pharmaceutical Bulletin 42 (10): 2211–2213. doi:10.1248/cpb.42.2211. PMID 7805143. 
  9. ↑ Fukuyama, Yoshiyasu; Kiriyama, Yuuko; Okino, Junko; Kodama, Mitsuaki; Iwaki, Hideyuki; Hosozawa, Sigeki; Matsui, Kuniaki (1993). "Naturally Occurring 5-Lipoxygenase Inhibitor. II. Structures and Syntheses of Ardisianones a and B, and Maesanin, Alkenyl-1,4-benzoquinones from the Rhizome of Ardisia japonica". Chemical and Pharmaceutical Bulletin 41 (3): 561–565. doi:10.1248/cpb.41.561. PMID 8477510. 




Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Ardisiaquinone&oldid=3423001"