Sesquiterpene lactone

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Sesquiterpene lactones are a class of chemical compounds; they are sesquiterpenoids (built from three isoprene units) and contain a lactone ring, hence the name. They are found in many plants and can cause allergic reactions and toxicity if overdosed, particularly in grazing livestock.[1] Some are also found in corals such as Maasella edwardsi.

Types[edit]

Structures of some sesquiterpene lactones:
A: Germacranolides, B: Heliangolides, C+D: Guaianolides, E: Pseudoguaianolides, F: Hypocretenolides, G: Eudesmanolides.

Sesquiterpene lactones can be divided into several main classes including germacranolides, heliangolides, guaianolides, pseudoguaianolides, hypocretenolides, and eudesmanolides.

Examples[edit]

Artemisinin, a new, highly-effective anti-malarial compound, is a sesquiterpene lactone found in Chinese wormwood. Lactucin, desoxylactucin, lactucopicrin, lactucin-15-oxalate, lactucopicrin-15-oxalate are some of the most prominent found in lettuce and spinach, giving most of the bitter taste to these crops.

One eudesmanolide, 3-oxo-5αH,8βH-eudesma-1,4(15),7(11)-trien-8,12-olide, can work with vernolic acid and other compounds in plants to reduce inflammation.[2]

Sesquiterpene lactone-containing plants[edit]

Some plants containing these compounds include:

Quorum sensing inhibitors

Sesquiterpene lactones have been found to possess the ability to inhibit quorum sensing in bacteria.[6]

See also[edit]

References[edit]

  1. ^ "Sesquiterpene Lactones and their toxicity to livestock". Cornell CALS. Cornell University. Retrieved December 29, 2018.
  2. ^ Nakagawa M, Ohno T, Maruyama R, Okubo M, Nagatsu A, Inoue M, Tanabe H, Takemura G, Minatoguchi S, Fujiwara H (September 2007). "Sesquiterpene lactone suppresses vascular smooth muscle cell proliferation and migration via inhibition of cell cycle progression". Biol. Pharm. Bull. 30 (9): 1754–7. doi:10.1248/bpb.30.1754. PMID 17827734.
  3. ^ Herz W, Kalyanaraman PS, Ramakrishnan G (June 1977). "Sesquiterpene lactones of Eupatorium perfoliatum". J. Org. Chem. 42 (13): 2264–71. doi:10.1021/jo00433a017. PMID 874606.
  4. ^ Dall'Acqua S, Viola G, Giorgetti M, Loi MC, Innocenti G (August 2006). "Two new sesquiterpene lactones from the leaves of Laurus nobilis". Chem. Pharm. Bull. 54 (8): 1187–9. doi:10.1248/cpb.54.1187. PMID 16880666.
  5. ^ Crellin JK, Philpott J, Tommie Bass AL (1990). Herbal Medicine Past and Present: A reference guide to medicinal plants. Duke University Press. pp. 265–. ISBN 0-8223-1019-8.
  6. ^ Amaya S, Pereira JA, Borkosky SA, Valdez JC, Bardón A, Arena ME (October 2012). "Inhibition of quorum sensing in Pseudomonas aeruginosa by sesquiterpene lactones". Phytomedicine. 19 (13): 1173–7. doi:10.1016/j.phymed.2012.07.003. PMID 22925726.