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Aus dem Ether-Extrakt der Blutenkopfchen der Schafgarbe (Achillea millefolium L.) wurden zwei Guaianolide (1,2) mit einer Peroxid-Brucke im Cyclopentan-Ring und einer α-Methylen-γ-butyrolacton-Struktur isoliert. Es werden die Bezeichnungen α-Peroxyachifolid (1) und β-Peroxyisoachifolid (2) vorgeschlagen. 1 ist u.a. verantwortlich fur die Schafgarbendermatitis. Peroxides as Plant Constituents, VIII1) Guaianolide-peroxides from Yarrow, Achillea millefolium L., Causing Allergic Contact Dermatitis From the ether extract of the blossoms of yarrow, Achillea millefolium L., two guaianolides (1, 2) with a peroxide bridged cyclopentane ring and an α-methylene-γ-butyrolactone structure have been isolated. For these compounds the names α-peroxyachifolid (1) and β-peroxyisoachifolid (2) are proposed. 1 is responsible for the allergic contact dermatitis caused by yarrow.

A new C 50 -hydroperoxide (1) with a hitherto unknown constitution, containing cadinane hydroperoxide and hyperforin (2) as partial structures, was isolated from the stems and leaves of St. John's wort (Hypericum perforatum L., Hypericaceae). The structure was elucidated by high-resolution NMR techniques (1D and 2D NMR experiments).

Aus Achillea filipendulina LAM. (Asteraceae) wurden zwei bisher nicht bekannte diastereomere, irregulare acyclische Monoterpenperoxide 5, 6 vom Typ des Santolinatriens isoliert (4α- bzw. 4β-Peroxyachipendol). Die Konstitution von 5 wurde durch Rontgenstrukturanalyse gesichert. 5 und 6 bilden durch Reduktion die in der Lit. beschriebenen Alkohole 8, 9, deren Struktur aufgrund dieser Ergebnisse korrigiert werden mus. Zusatzlich wurden in A. filipendulina Ascaridol (1), trans-Pinocarveylhydroperoxid (2) und Isolyratylhydroperoxid A (3) und B (4) nachgewiesen. Peroxides as Constituents of Plants, XV: Irregular Monoterpene Peroxides from Achillea filipendulina LAM. From Achillea filipendulina LAM. (Asteraceae) two hitherto unknown diastereomeric, irregular acyclic monoterpene peroxides 5, 6 of santolina triene type have been isolated (4α- and 4β-peroxyachipendole). The constitution of 5 was confirmed by X-ray analysis. Reduction of 5 and 6 results in the formation of the alcohols 8 and 9, respectively. Constitutions of 8 and 9, reported in lit., have to be corrected. In addition, ascaridole (1), trans-pinocarveylhydroperoxide (2) and isolyratylhydroperoxide A (3) and B (4) have been found.

1,4-Epidioxy-bisabola-2,12-diene (3) and aromatic hydroperoxides (4, 5) were prepared by photoxidation of gamma-curcumene (1). Reduction and esterification of 6 and 7 afforded compounds 9 to 10. All compounds were tested in vitro for antimalarial activity. The activity could not be increased significantly, compared with 3. The most active compounds, 3 and 9, did not show in vivo antimalarial activity in mice.

From the ether extract of the blossoms of yarrow, Achillea millefolium L., two guaianolides (1, 2) with a peroxide bridged cyclopentane ring and an alpha-methylene-gamma-butyrolactone structure have been isolated. For these compounds the names alpha-peroxyachifolid (1) and beta-peroxyisoachifolid (2) are proposed. 1 is responsible for the allergic contact dermatitis caused by yarrow.

Aus den oberirdischen Teilen von Artemisia maritima L. ssp. maritima (Asteraceae) wurde neben dem bekannten Sesquiterpenhydroperoxid Arteinculton (1) em neues cyclisches funfgliedriges Sesquiterpen-Peroxyhalbketal (2) isoliert. Die Struktur wurde durch spektroskopische Methoden aufgeklart.