4-Methyl-1-phenylpentane-1,3-dione and 2-isopropylchromone from the essential oil of Lophomyrtus bullata

Briggs, Lindsay H.; White, G. W.

doi:10.1039/j39710003077

Cited by 14 publications

(2 citation statements)

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“…PTLC of the early fractions (hexane-Et 2 O, 9 : 1 v/v) followed by GCMS and NMR resulted in the identification of the minor constituents as 1-hydroxy-4-methyl-1-phenyl-1-penten-3-one 2, 11 benzyl salicylate 13 33 and phyllocladene 14 (enantiomer not determined, 1 H NMR spectrum identical to an authentic sample 34 ). Bullatenone 1 11 and 5-hydroxyflavone 12 35 were similarly isolated from the later fractions and identified by NMR, MS and melting points. From the centre-cut fractions crystals slowly separated.…”

Section: Isolationmentioning

confidence: 99%

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A cytotoxic triketone–phloroglucinol–bullatenone hybrid from Lophomyrtus bullata

et al. 2005

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Cytotoxic activity against the P388 cell line was seen in a crude extract of the New Zealand shrub Lophomyrtus bullata(Myrtaceae). Bioactivity-guided isolation led to a compound with NMR spectra complicated by the presence of two isomers. These crystallised together and an X-ray structure showed them to be stereoisomeric hybrids of triketone, phloroglucinol and bullatenone units. NMR measurements on the mixed isomers, as well as a cyclic ether produced from them by acid catalysed dehydration, were consistent with these structures. The natural products, named bullataketals A and B, have cytotoxic activity against the P388 cell line (IC(50) 1 microg ml(-1)), and antimicrobial activity against Bacillus subtilis.

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Section: Isolationmentioning

confidence: 99%

“…10 Subsequent studies of the essential oil identified as additional constituents a-and bpinene, (−)-alloaromadendrene, 1-hydroxy-4-methyl-1-phenyl-1-penten-3-one 2 and 2-isopropylchromone. 11 We now report the compounds responsible for the cytotoxic and antimicrobial properties of the plant extracts.…”

Section: Introductionmentioning

confidence: 99%