ABSTRACT
Lepidozenal and isobicyclogermacrenal were isolated from the leaves of Eucalyptus dawsonii and a complete assignment of their 1H and 13C NMR spectra was carried out using 2D NMR methods.
Subject(s)
Aldehydes/chemistry , Eucalyptus/chemistry , Magnetic Resonance Spectroscopy/methods , Magnetic Resonance Spectroscopy/standards , Sesquiterpenes/chemistry , Aldehydes/isolation & purification , Carbon Isotopes , Chromatography, Gas/methods , Mass Spectrometry/methods , Models, Molecular , Molecular Conformation , Plant Leaves/chemistry , Protons , Reference Standards , Sensitivity and Specificity , Sesquiterpenes/isolation & purification , StereoisomerismABSTRACT
An analytical method for determining the quality and hence the chemical variety status of tea tree transplants is described. The key to the procedure was found to be the leaf age of the test material. Investigation at very early development stages was seen to give misleading results due to the sequential onset of different monoterpenoid biogenetic pathways. For example, in the first few leaves, the high concentration of terpinolene in the terpinen-4-ol variety suggests that the terpinolene variety is under investigation. However, 1,8-cineole percent concentrations in plantation tree leaf were approximately 1.6 times lower than those measured for seedlings prior to transplant. Consequently, the use of a plantation cineole indicator is proposed for estimating plantation cineole from seedling leaf analyses. Although recent investigations enable the chemotype status to be predicted with some certainty, it is now proposed that analysis of leaf set 10 at the age of 6 weeks (seedling age approximately 17 weeks) provides an unambiguous analysis and correlates seedling quality with mature plantation quality. In addition, the oil yield of mature tea tree leaf was found, by steam distillation, to be approximately 5 times higher than that of seedling leaf.
Subject(s)
Melaleuca/growth & development , Monoterpenes , Seedlings/growth & development , Tea Tree Oil/analysis , Cyclohexanols/analysis , Eucalyptol , Melaleuca/chemistry , Plant Leaves/chemistry , Seedlings/chemistry , Terpenes/analysisABSTRACT
In order to compare the metabolism of 1,8-cineole in the pyrgo beetle, Paropsisterna tigrina, three other herbivorous insect species, Faex nigroconspersa, Chrysophtharta bimaculata, and Oxyops vitiosa, were fed 1,8-cineole leaf diets. F. nigroconspersa adults excreted predominantly 9-hydroxy-1,8-cineole (36.2% of the volatile constituents) with some 2alpha-hydroxy-1,8-cineole (11.4%). In contrast, larvae excreted predominantly 2alpha-hydroxy-1,8-cineole (27.4%) and smaller proportions of 9-hydroxy-1,8-cineole (5.2%) and 3alpha-hydroxy-1,8-cineole (4.3%). C. bimaculata adults excreted predominantly 3alpha-hydroxy-1,8-cineole (16.5%). Oxyops vitiosa adults, on a lower 1,8-cineole diet, excreted predominantly 2alpha,9-dihydroxy-1,8-cineole (4.2%) and 2alpha-hydroxy-1,8-cineole (3.5%), with smaller proportions of 3alpha-hydroxy-1,8-cineole (1.1%) and 9-hydroxy-1,8-cineole (0.5%). This is the first reported occurrence of a dihydroxycineole as an insect metabolite. Gas chromatographic and mass spectral data for hydroxycineoles are recorded and interspecific metabolite variation discussed.
Subject(s)
Coleoptera/physiology , Cyclohexanols/metabolism , Diptera/physiology , Grasshoppers/physiology , Monoterpenes , Solvents/metabolism , Terpenes/metabolism , Animals , Eucalyptol , Eucalyptus , Gas Chromatography-Mass Spectrometry , Larva/physiologyABSTRACT
Individual leaves of the three most common chemotypes of Melaleuca alternifolia were examined both quantitatively and qualitatively for volatile constituents from the emergence of the first true leaves, through to 6-week-old tenth leaf set material. The 1,8-cineole and terpinolene chemotypes were investigated and compared with the recently reported commercial terpinen-4-ol chemotype. The 1,8-cineole chemotype was found to accumulate 1,8-cineole and associated p-menthanes limonene, terpinen-4-ol and alpha-terpineol gradually with increasing leaf set number. As with the terpinen-4-ol variety, higher than expected concentrations of the pinenes and terpinolene were found only in the early leaf sets. The terpinolene variety showed two stages of terpinolene accumulation, the first at leaf sets 2-3 similar to the unexpected biosynthesis of terpinolene in the terpinen-4-ol chemotype and the second at leaf sets 8-9 which is characteristic of the terpinolene variety.
Subject(s)
Melaleuca/metabolism , Monoterpenes/metabolism , Tea Tree Oil/metabolism , Terpenes/metabolism , Cyclohexane Monoterpenes , Cyclohexanols/chemistry , Cyclohexanols/isolation & purification , Cyclohexanols/metabolism , Eucalyptol , Melaleuca/chemistry , Plant Leaves/anatomy & histology , Plant Leaves/chemistry , Plant Leaves/growth & development , Plant Leaves/metabolism , Seedlings/chemistry , Seedlings/metabolism , Tea Tree Oil/chemistry , Terpenes/chemistry , Terpenes/isolation & purificationABSTRACT
Oil quantity and quality were measured for the cotyledon leaves of the commercial terpinen-4-ol chemical variety of Melaleuca alternifolia. Oil yield obtained by ethanolic extraction was 3.8 micrograms per leaf or 2.6% (dry weight basis). The major components of the oil were alpha-pinene (7.4%), beta-pinene (12.0%) and terpinolene (27.3%). The non-commercial terpinolene chemical variety was found to be rich in 1,8-cineole (12.5%) and terpinolene (25.4%). The non-commercial 1,8-cineole chemical variety was rich in 1,8-cineole (37%) with significant quantities of alpha-pinene (15.5%), beta-pinene (23.3%) and terpinolene (10.9%). The cotyledon leaf composition, when compared with that of mature leaf from the same chemical variety, was found to be biased toward pinene and terpinolene biogenetic pathway constituents and hence not a good indicator of mature tree quality especially for the commercial terpinen-4-ol chemical variety. The implications of these analyses for the determination of M. alternifolia plantation quality and the understanding of oil formation, are discussed.
