The sensitizing capacity of naturally occurring quinones.—Experimental studies in guinea pigs

SummaryExperimental studies on the sensitization capacity of naturally occurring naphthoquinones derived from plants and woods have been carried out with 6 compounds. With 4 of these substances (desoxylapachol, menadione, lapachenole and macassar quinone) guinea pigs could be sensitized. Desoxylapachol, sensitizer from teak wood, and lapachenole, sensitizer from peroba wood proved to be the most effective ones. Experiments with macassar quinone (oxidation product of a naphthalene constituent of macassar ebony) still demonstrate that even ortho-naphthoquinones are capable to induce contact allergy. Allergic cross reactions could be obtained with 9 out of 14 different napthoquinones. In animals sensitized with desoxylapachol menadione and lapachol showed the strongest eliciting effect.Furthermore the study demonstrated that the sensitizing effect of naphthoquinones depends on the length and position of the side chain attached to the quinoid ring as well as on the substitution of the carbon atom adjacent to the side chain bearing C-atom. With compounds substituted at this C-atom (e.g. position 3 of lapachol or didimethylallylnaphthoquinone) sensitization could not be obtained.ZusammenfassungExperimentelle Untersuchungen über das Sensibilisierungsvermögen von natürlich vorkommenden Naphthochinonen und ihren Derivaten aus Pflanzen und Hölzern wurden mit 6 Verbindungen vorgenommen. Mit 4 von ihnen (Desoxylapachol, Vitamin K3, Lapachonon und Makassarchinon) konnten Meerschweinchen sensibilisiert und kontaktallergische Reaktionen ausgelöst werden. Als besonders starke Sensibilisatoren erwiesen sich Desoxylapachol (kurz DOL) (Allergen aus Teakholz) und Lapachonon (Allergen aus Peroba-Holz). Mit einem schwächeren Sensibilisator (dem Makassarchinon, einem Oxidationsprodukt eines Naphthalinderivats aus Makassar-Holz) konnte gezeigt werden, daß auch ortho-Naphthochinone eine Kontaktallergie zu induzieren vermögen.Kreuzreaktionsversuche mit 14 zum größten Teil aus der Natur stammenden Naphthochinonderivaten an den mit den oben genannten Naphthochinonen sensibilisierten Tieren ergaben in 9 Fällen ein positives Ergebnis. Mit 6 Verbindungen ließen sich Kreuzreaktionen an DOL-sensibilisierten Meerschweinchen auslösen. Am stärksten auslösend wirksam waren Vitamin K3 und Lapachol. Weiterhin zeigten die Untersuchungen, daß die Sensibilisierungsfähigkeit von Naphthochinonen sowohl von der Länge und Position der Seitenkette am chinoiden Ring als auch von der Substitution des danebenliegenden C-Atoms abhängig ist. Mit Verbindungen, bei denen das C-Atom neben der Seitenkette substituiert ist (z.B. 3. C-Atom bei Lapachol oder Didimethylallylnaphthochinon) konnte keine Sensibilisierung erzielt werden.

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