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The sensitizing capacity of naturally occurring quinones experimental studies in guinea pigs

II. Benzoquinones

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Summary

Experimental studies on the sensitizing capacity of naturally occurring benzoquinones, isolated from plants and woods have been carried out in guinea pigs of the Pirbright white strain. Seven compounds were available: primin, three dalbergiones, mansonia quinone (mansonone A), 2,6-dimethoxybenzoquinone and rapanone. With five of these substances (primin, mansonone A, three dalbergiones) guinea pigs could be sensitized. Primin, the allergen of Primula obconica Hance (primrose) proved to be the most effective one of all quinones tested in this and the preceding studies. As a similar but weaker sensitizer R-3,4-dimethoxydalbergione from Machaerium scleroxylon Tul. (Pao ferro, Caviuna vermalha) could be identified.

The results obtained with mansonone A, a sesquiterpenoid quinone from Mansonia altissima A. Chev. demonstrate that even naturally occurring orthoquinones are capable of inducing contact allergy. Allergic cross reactions could be obtained between all chemically related mansonones A — F.

The results are in good accordance with the view that the sensitizing capacity of naturally occurring quinones depends on the fundametal quinoid structure and the length, position and configuration of the aliphatic side-chain.

Zusammenfassung

Experimentelle Untersuchungen über das Sensibilisierungsvermögen von natürlich vorkommenden Benzochinonen aus Pflanzen und Hölzern wurden an Meerschweichen des Pirbright-white-Stammes durchge-führt. Sieben Verbindungen standen zur Verfügung: Primin, drei Dalbergione, Mansonia Chinon (Mansonon A), 2,6-Dimethoxybenzochinon und Rapanon. Mit fünf von ihnen (Primin, Mansonon A, drei Dalbergionen) konnten die Tiere sensibilisiert werden.

Primin, das Allergen der Becherprimel Primula obconica Hance erwies sich als das stärkste aller in dieser und der vorherigen Studie untersuchten Chinone. Ein etwas schwächerer Sensibilisator war das R-3,4-dimethoxydalbergion aus Machaerium scleroxylon Tul. (Pao ferro, Caviuna vermelha).

Die Resultate mit Mansonon A, einem sesquiterpenoiden Chinon aus Mansonia altissima A. Chev. (Mansonia, Bété) zeigten, daß auch natürlich vorkommende Ortho-Chinone eine Kontaktallergie zu induzieren vermögen. Mit den chemisch verwandten Mansononen B — F konnten Kreuzreaktionen ausgelöst werden.

Die Untersuchungsergebnisse zeigten ernut, daß die Sensibilisierungsfähigkeit von natürlich vorkommenden Chinonen sowohl von der chinoiden Grundstruktur als auch von der Länge, Position und Konfiguration der aliphatischen Seitenkette abhängt.

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Authors and Affiliations

  1. Department of Dermatology, Division of Allergology and Occupational Dermatoses, University Hospital, Martinistr. 52, D-2000, Hamburg 20

    K. H. Schulz, I. Garbe & B. M. Hausen

  2. Institute of Wood Chemistry, University of Hamburg, Leuschnerstr. 91 b, D-2050, Hamburg 80, Federal Republic of Germany

    M. H. Simatupang

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  1. K. H. Schulz
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  2. I. Garbe
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  3. B. M. Hausen
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  4. M. H. Simatupang
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This study was supported by grant of Deutsche Forschungsgemeinschaft

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Schulz, K.H., Garbe, I., Hausen, B.M. et al. The sensitizing capacity of naturally occurring quinones experimental studies in guinea pigs. Arch Dermatol Res 264, 275–286 (1979). https://doi.org/10.1007/BF00412654

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