Ardisiaquinone Explained

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]}

Notes and References

1. 10.1016/S0040-4039(01)98959-2 . The structures of ardisiaquinones A, B and C, bis(benzoquinonyl)-olefine derivatives from miquel . 1968 . Ogawa . H. . Sakaki . S. . Yoshihira . K. . Natori . S. . Tetrahedron Letters . 9 . 11 . 1387–1392 .
2. 10.1248/cpb.43.1391 . Naturally Occurring 5-Lipoxygenase Inhibitors. VI. Structures of Ardisiaquinones D, e, and F from Ardisia sieboldii . 1995 . Fukuyama . Yoshiyasu . Kiriyama . Yuuko . Kodama . Mitsuaki . Iwaki . Hideyuki . Hosozawa . Shigeki . Aki . Shinji . Matsui . Kuniaki . Chemical and Pharmaceutical Bulletin . 43 . 8 . 1391–1394 . 7553985 . free .
3. 10.1016/s0031-9422(01)00317-x . Ardisiaquinones from Ardisia teysmanniana . 2001 . Yang . Lay-Kien . Khoo-Beattie . Corinne . Goh . Kay-Lin . Chng . Bee-Lee . Yoganathan . K. . Lai . Yee-Hing . Butler . Mark S. . Phytochemistry . 58 . 8 . 1235–1238 . 11738414 .
4. Book: 10.1016/B978-0-12-819483-6.00008-4 . Natural products as antiinflammatory agents . Bioactive Natural Products . Studies in Natural Products Chemistry . 2020 . Narayanaswamy . Radhakrishnan . Veeraragavan . Vijayakumar . 67 . 269–306 . 9780128194836 . 224940163 .
5. 10.1055/s-2005-871252 . Protective Effect of the 5-Lipoxygenase Inhibitor Ardisiaquinone a on Hepatic Ischemia-Reperfusion Injury in Rats . 2005 . Matsui . Nobuaki . Fukuishi . Nobuyuki . Fukuyama . Yoshiyasu . Yasui . Yumiko . Akagi . Masaaki . Planta Medica . 71 . 8 . 717–720 . 16142634 .
6. 10.1078/s0944-7113(04)70065-3 . Antiallergic effect of ardisiaquinone A, a potent 5-lipoxygenase inhibitor . 2001 . Fukuishi . N. . Takada . T. . Fukuyama . Y. . Akagi . M. . Phytomedicine . 8 . 6 . 460–464 . 11824521 .
7. 10.3109/13880209.2013.837076 . Antiproliferative and antimicrobial activities of alkylbenzoquinone derivatives from Ardisia kivuensis . 2014 . Paul . Dzoyem J. . Laure . Ndontsa B. . Guru . Santosh K. . Khan . Inshad A. . Ajit . Saxena K. . Vishwakarma . Ram A. . Pierre . Tane . Pharmaceutical Biology . 52 . 3 . 392–397 . 24192208 . 35830795 .
8. 10.1248/cpb.42.2211 . Total Synthesis of Ardisiaquinone A, a Potent 5-Lipoxygenase Inhibitor, Isolated from Ardisia sieboldii, and Degree of 5-Lipoxygenase Inhibitory Activity of Its Derivatives . 1994 . Fukuyama . Yoshiyasu . Kiriyama . Yuuko . Kodama . Mitsuaki . Iwaki . Hideyuki . Hosozawa . Shigeki . Aki . Shinji . Matsui . Kuniaki . Chemical and Pharmaceutical Bulletin . 42 . 10 . 2211–2213 . 7805143 . free .
9. 10.1248/cpb.41.561 . 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 . 1993 . Fukuyama . Yoshiyasu . Kiriyama . Yuuko . Okino . Junko . Kodama . Mitsuaki . Iwaki . Hideyuki . Hosozawa . Sigeki . Matsui . Kuniaki . Chemical and Pharmaceutical Bulletin . 41 . 3 . 561–565 . 8477510 . free .