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 of the order Alcyonacea.

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

^ 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.
^ "Sesquiterpene Lactones and their toxicity to livestock". Cornell CALS. Cornell University. Retrieved December 29, 2018.
^ 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. hdl:20.500.12099/23170. PMID 17827734.
^ 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.
^ 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.
^ 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.
^ 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.

External links

Media related to Sesquiterpene lactones at Wikimedia Commons

[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.

[pmid17827734-3] 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. hdl:20.500.12099/23170. PMID 17827734.

[pmid874606-4] 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.

[pmid16880666-5] 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.

[pmid22925726-7] 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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