Struktur der Sesquiterpene von Petasites hybridus (L.) G. M.et SCH.: Petasol‐ und Isopetasol‐Abkömmlinge

Abstract

Structure of the Sesquiterpenes of Petmifes hybridus (L.) G. M. et SCH.: Petasol and Isopetasol Derivatives SummaryThe structure of 11 compounds of the sesquiterpene fraction of petasites hybridus has been determined by combination of spectroscopic methods, especially by analysis of the 360-MHz-'H-NMR. spectra. Most natural products are esters of two isomeric sesquiterpene alcohols, characterized by an eremophilan skeleton, namely of petasol as well as of isopetasol. The structure of one key product has been confirmed by X-ray analysis. 1.Einleitung. -Obwohl die gemeine Pestwurz (petusites hybridus) im Mittelalter gelegentlich als Naturheilmittel verwendet wurde und sich bis in die Neuzeit in der Homoopathie gehalten hat, war uber die Inhaltstoffe von Petasites hybridus lange Zeit recht wenig bekannt. Erst die Beobachtung von Bucher [4], dass die

Four New Sesquiterpenes from Petasites formosanus

“…Further separation of these fractions by MPLC and HPLC on Si gel column led to the isolation of four new eremophilanes, petasone A (1), petasone B ( 2), (S)-petasitin (3), and petasinol (4), together with three known compounds, (S)-petasin (5), 2 (S)-isopetasin (6), 10 and petasitin (7). 11 Petasone A (1) was obtained as a colorless oil, which was shown to have a molecular formula C 19 H 26 O 4 S by HRMS and 13 C NMR spectrum. The IR spectrum showed the presence of R,β-unsaturated carbonyl (1660 cm -1 ), sulfoxide (1050 cm -1 ), and R,β-unsaturated ester (1710 and 1210 cm -1 ) groups.…”

6β-Angeloyloxy-3β,8β-dihydroxyeremophil-7(11)-en-12,8α-olide

“…For general background, see: Agosti et al (2006); Bodensieck et al (2007); Cremer & Pople (1975); Fiebich et al (2005); Gray et al (2004); Jackson et al (2004); Lipton et al (2004); ; Neuenschwander, Neuenschwander, Steinegger & Engel (1979); Saritas et al (2002); Siegenthaler & Neuenschwander (1997); Sugama et al (1985); Thomet & Simon (2002); Thomet et al (2001); Yaoita & Kikuchi (1994); Yaoita et al (1992).…”

“…Its extracts were proved to have activities of anti-migraine (Lipton et al, 2004;Agosti et al, 2006), anti-allergy (Thomet & Simon, 2002;Gray et al, 2004;Jackson et al, 2004) and anti-inflammatory (Thomet et al, 2001;Fiebich et al, 2005). Many sesquiterpenes of the eremophilanolide type have been obtained from P. Hybridus (L.) Neuenschwander, Neuenschwander, Steinegger & Engel, 1979;Siegenthaler & Neuenschwander, 1997;Saritas et al, 2002;Bodensieck et al, 2007). Our investigation on the roots of this plant for bioactive components resulted in the isolation of the title compound (I), which was previously obtained from another plant P. Japonicus mixed together with its isomer, 6β-angeloyloxy-3β,8α-dihydroxyeremophil-7(11)en-12,8β-olide (Sugama et al, 1985).…”

Low-Molecular-Weight Organosulfur Compounds in Nature: The Search for New Pesticides

“…These examples would include diethyl tetrasulfide, (C2H 5 SS)2, and related polysulfides and hydrosulfides from the fruit of the durian, Durio zibethinus (a much cherished south-east Asian fruit) (18), germacradienolide thiol 8 from Eupatorium mikanioides (19), sesquiterpene lactone su If one g from the roots of Eelenium autvamale (20), vinyl sulfides 10 and 11 (S-petasin) from Petasites japonicus and Petasites nybridus^ respectively (21,22), thiosulfonate 12, from the mushroom Lentinus edodes, and S-methylthiomethyl 2-methylbutanethioate, C2H 5 CH(CH 3 )C(0)SCH 2 SCH 3 , from the essential oil of hops (23). (See Figure 3.) Animal Sources.…”