Ardisiaquinone

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]

Ardisiaquinones
Identifiers
3D model (JSmol)
  • A: InChI=1S/C30H40O8/c1-37-25-19-23(31)27(33)21(29(25)35)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-22-28(34)24(32)20-26(38-2)30(22)36/h3-4,19-20,33-34H,5-18H2,1-2H3/b4-3-
    Key: RSYDDJMZYDRCOF-ARJAWSKDSA-N
  • B: InChI=1S/C30H40O8/c1-20-25(32)29(36)22(30(37)26(20)33)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-21-27(34)23(31)19-24(38-2)28(21)35/h3-4,19,32,34,37H,5-18H2,1-2H3/b4-3-
    Key: KRSLVFPYJNSDEQ-ARJAWSKDSA-N
  • D: InChI=1S/C31H42O8/c1-21-26(33)29(36)23(30(37)31(21)39-3)19-17-15-13-11-9-7-5-4-6-8-10-12-14-16-18-22-27(34)24(32)20-25(38-2)28(22)35/h4-5,20,34,36H,6-19H2,1-3H3/b5-4-
    Key: CEYKFDJEGPDJSH-PLNGDYQASA-N
  • E: InChI=1S/C29H40O6/c1-35-27-21-26(32)28(33)25(29(27)34)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-22-18-23(30)20-24(31)19-22/h2-3,18-21,30-31,33H,4-17H2,1H3/b3-2-
    Key: UAVAYCHSCHCWEM-IHWYPQMZSA-N
  • F: InChI=1S/C30H42O6/c1-22-25(31)19-23(20-26(22)32)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-24-29(34)27(33)21-28(36-2)30(24)35/h3-4,19-21,31-32,34H,5-18H2,1-2H3/b4-3-
    Key: VHRGRLJMZWTPMP-ARJAWSKDSA-N
  • G: InChI=1S/C31H40O10/c1-18-24(34)28(38)23(31(26(18)36)41-21(4)33)17-15-13-11-9-7-5-6-8-10-12-14-16-22-27(37)25(35)19(2)30(29(22)39)40-20(3)32/h34,37H,5-17H2,1-4H3
    Key: AVPDKIQZUGDDMG-UHFFFAOYSA-N
  • A: COC1=CC(=O)C(=C(C1=O)CCCCCCC/C=C\CCCCCCCC2=C(C(=O)C=C(C2=O)OC)O)O
  • B: CC1=C(C(=O)C(=C(C1=O)O)CCCCCCC/C=C\CCCCCCCC2=C(C(=O)C=C(C2=O)OC)O)O
  • D: CC1=C(C(=O)C(=C(C1=O)O)CCCCCCC/C=C\CCCCCCCC2=C(C(=O)C=C(C2=O)OC)O)OC
  • E: COC1=CC(=O)C(=C(C1=O)CCCCCCC/C=C\CCCCCCCC2=CC(=CC(=C2)O)O)O
  • F: CC1=C(C=C(C=C1O)CCCCCCC/C=C\CCCCCCCC2=C(C(=O)C=C(C2=O)OC)O)O
  • G: CC1=C(C(=O)C(=C(C1=O)OC(=O)C)CCCCCCCCCCCCCC2=C(C(=O)C(=C(C2=O)OC(=O)C)C)O)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 A
  • Ardisiaquinone B
    Ardisiaquinone B
  • Ardisiaquinone C
    Ardisiaquinone C
  • Ardisiaquinone D
    Ardisiaquinone D
  • Ardisiaquinone E
    Ardisiaquinone E
  • Ardisiaquinone F
    Ardisiaquinone F
  • Ardisiaquinone G
    Ardisiaquinone G

References
  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. Narayanaswamy, Radhakrishnan; Veeraragavan, Vijayakumar (2020). "Natural products as antiinflammatory agents". Bioactive Natural Products. Studies in Natural Products Chemistry. Vol. 67. pp. 269–306. doi:10.1016/B978-0-12-819483-6.00008-4. ISBN 9780128194836. S2CID 224940163.
  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. S2CID 35830795.
  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.
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