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Nortriketones: Antimicrobial Trimethylated Acylphloroglucinols from Ma̅nuka (Leptospermum scoparium)

Author:
Killeen, Daniel P., Larsen, Lesley, Dayan, Franck E., Gordon, Keith C., Perry, Nigel B., van Klink, John W.
Source:
Journal of natural products 2016 v.79 no.3 pp. 564-569
ISSN:
1520-6025
Subject:
4-hydroxyphenylpyruvate dioxygenase, Gram-positive bacteria, Leptospermum scoparium, Myrica gale, Myrtus communis, Raman spectroscopy, antibacterial properties, herbicides, ketones, leaves
Abstract:
Four trimethylated acylphloroglucinols (5–8) have been isolated from ma̅nuka (Leptospermum scoparium) foliage. Apart from myrigalone A (8), which has previously been isolated from European bog myrtle (Myrica gale), these compounds have not been characterized before. The nortriketones are structurally similar to the bioactive tetramethylated β-triketones from ma̅nuka, but have one less ring methyl group. Two oxidized trimethylated compounds, 9 and 10, were also isolated, but these are likely isolation artifacts. When evaluated for antibacterial activity against Gram-positive bacteria, myrigalone A (8) was slightly less potent (MIC 64 μg/mL) than the corresponding tetramethylated compound, grandiflorone (4) (MIC 16–32 μg/mL). Unlike their tetramethylated analogues, the nortriketones were inactive against the herbicide target enzyme p-hydroxyphenylpyruvate dioxygenase. The Raman spectra of leaf oil glands in different ma̅nuka varieties can be used to distinguish plants that contain nortriketones from those that accumulate triketones.
Agid:
5498419