Isolation and Identification of Acylphloroglucinols in the Medicinal Plant, Melaleuca alternifolia (Australian Tea Tree)

Abstract

Melaleuca alternifolia (tea tree), family Myrtaceae, is endemic to the northern rivers of NSW, Australia. Since 1925, the volatile components of the hydro- and steam-distilled oils of the leaves have been studied in detail. However, the less-volatile compounds have not been investigated. Using an ethanolic extract of the seedling leaves, the non-volatile components were studied using gas chromatography-mass spectrometry (GC/MS) and liquid chromatography- mass spectrometry (LC/MS). Four of these less-volatile components were isolated by preparative-HPLC from young seedling leaves and identified as the acylphloroglucinols 1-(2,6-dihydroxy-4-methoxy-3-methylphenyl)-2-methylpropan-1-one, callisalignone A, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-methylbutan-1-one and pulverulentone B described here for the first time from M. alternifolia. These compounds change in concentration in the leaf sets as later seedling leaves mature on the seedling.