Sesquiterpene lactone

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

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 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

Some plants containing these compounds include:

See also

References

  1. ↑ Sesquiterpene Lactones and their toxicity to livestock
  2. ↑ Munehiro Nakagawa, Takamasa Ohno, Rumi Maruyama, Munenori Okubo, Akito Nagatsu, Makoto Inoue, Hiroki Tanabe, Genzou Takemura, Shinya Minatoguchi and Hisayoshi Fujiwara (2007). "Sesquiterpene Lactone Suppresses Vascular Smooth Muscle Cell Proliferation and Migration via Inhibition of Cell Cycle Progression". Biol.Pharm. Bull. 30 (9): 1754–1757. doi:10.1248/bpb.30.1754. PMID 17827734.
  3. ↑ Herz, Werner; Kalyanaraman, Palaiyur S.; Ramakrishnan, Ganapathy; Blount, John F. (1977). "Sesquiterpene lactones of Eupatorium perfoliatum". The Journal of Organic Chemistry 42 (13): 2264–71. doi:10.1021/jo00433a017. PMID 874606.
  4. ↑ Dall'Acqua, S.; Viola, G.; Giorgetti, M.; Loi, M. C.; Innocenti, G. (2006). "Two new sesquiterpene lactones from the leaves of Laurus nobilis". Chemical & pharmaceutical bulletin 54 (8): 1187–1189. doi:10.1248/cpb.54.1187. PMID 16880666.
  5. ↑ J. K. Crellin, Jane Philpott, A. L. Tommie Bass, Contributor Jane Philpott, 1989, A Reference Guide to Medicinal Plants: Herbal Medicine Past and Present, Duke University Press, 560pp. ISBN 0-8223-1019-8, ISBN 978-0-8223-1019-8
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