Sesquiterpeenlactonen / Sesquiterpenoïden

In traditional medicine, alcoholic preparations from flowers of Arnica montana and Arnica chamissonis ssp.foliosa are applied externally to treat hematomas, contusions, sprains, rheumatic diseases, and superficial inflammations of the skin. The secondary metabolites that mediate the anti-inflammatory effects are sesquiterpene lactones of the 10α-methylpseudoguaianolide type like helenalin, 11α,13-dihydrohelenalin, chamissonolid, and their ester derivatives (1-3). Several studies have investigated how these natural compounds exert their anti-inflammatory effect. Sesquiterpene lactones have been shown to modulate many processes that influence inflammatory reactions, for example, oxidative phosphorylation, platelet aggregation, histamine and serotonin release (3, 4). These activities are mediated chemically by α,β-unsaturated carbonyl structures, such as an α-methylene-γ-lactone or an α,β-unsubstituted cyclopentenone. These structure elements react with nucleophiles, especially cysteine sulfhydryl groups, by a Michael-type addition (5, 6). Therefore, exposed thiol groups, such as cysteine residues in proteins, appear to be the primary targets of sesquiterpene lactones. Some sesquiterpene lactones, for example, helenalin, possess two alkylant structure elements which may be responsible for their remarkably high activity (5-8). However, other factors, such as lipophilicity, molecular geometry, and the chemical environment of the target sulfhydryl may also influence the activity of sesquiterpene lactones (6).

Sesquiterpene lactone-containing plants

Laurus nobilis

Chrysanthemum

Yellow star thistle

Ginkgo biloba

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.

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. edit

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

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.

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