Quinonoid constituents as contact sensitisers in Australian blackwood (Acacia melanoxylon RBR).
Australian blackwood (Acacia melanoxylon RBR) is a valuable commercial timber that since 1925 has been incriminated as being injurious to health. In addition to toxic effects numerous cases of allergic contact dermatitis and bronchial asthma have been observed in woodworkers. Several constituents have been identified in recent years, but none of them could be considered as aetiological factors. Sensitizing experiments performed with blackwood heartwood extracts corroborated the described sensitising properties. Chemical studies showed the occurrence of two or possibly three quinones that produced positive skin responses in the sensitised guinea pigs. The main contact allergens were isolated and identified by x-ray analysis. The first, a yellow quinone, was identified as 2,6-dimethoxy-1,4-benzoquinone while the second, a red quinone, has the structure of 6-methoxy-2-methyl-3,5-dihydrobenzofurano-4,7-dion and was named acamelin. Whereas 2, 6-dimethoxy-p-benzoquinone is already known from natural sources, acamelin is new and  belongs to the rate group of naturally occurring furanoquinones. Though the obtained sensitising capacity of A melanoxylon RBR in respect of its quinones is not high, it should be considered as a possible source of allergic contact dermatitis, especially as greater amounts of Australian blackwood may enter European countries in the near future.
D000045:Acacia / Q000032:analysis*; D000485:Allergens / Q000032:analysis*; D000818:Animals; D001572:Benzofurans / Q000032:analysis*; D016227:Benzoquinones; D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D003877:Dermatitis, Contact / Q000209:etiology; D005260:Female; D006168:Guinea Pigs; D011809:Quinones / Q000032:analysis*; D012882:Skin Tests
D000485:Allergens; D001572:Benzofurans; D016227:Benzoquinones; D011809:Quinones; C030511:2,6-dimethoxy-1,4-benzoquinone; C030510:acamelin