Sesquiterpene lactone

Sesquiterpene lactones (SLs) are a class of sesquiterpenoids that contain a lactone ring. They are most often found in plants of the family Asteraceae (daisies, asters). Other plant families with SLs are Umbelliferae (celery, parsley, carrots) and Magnoliaceae (magnolias). A collection of colorless, lipophilic solids, SLs are a rich source of drugs.[1] They can be allergenic and toxic in grazing livestock[2] causing severe neurological problems in horses. Some are also found in corals such as Maasella edwardsi.

Types
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

Artemisinin, a new, highly-effective anti-malarial compound, is a sesquiterpene lactone found in Artemisia annua. 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.[3]

Sesquiterpene lactone-containing plants

Some plants containing these compounds include:

Quorum sensing inhibitors

Sesquiterpene lactones have been found to possess the ability to inhibit quorum sensing in bacteria.[7]

References
  1. Ghantous, Akram; Gali-Muhtasib, Hala; Vuorela, Heikki; Saliba, Najat A.; Darwiche, Nadine (2010). "What Made Sesquiterpene Lactones Reach Cancer Clinical Trials?". Drug Discovery Today. 15 (15–16): 668–678. doi:10.1016/0305-1978(86)90101-8. PMID 20541036.
  2. "Sesquiterpene Lactones and their toxicity to livestock". Cornell CALS. Cornell University. Retrieved December 29, 2018.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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. hdl:11336/77653. PMID 22925726.
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