The structure of squamulosone, a new sesquiterpene ketone from Phebalium squamulosum

Batey, I. L.; Hellyer, RO; Pinhey, JT

doi:10.1071/ch9712173

Cited by 18 publications

(9 citation statements)

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“…We found an additional oxidation product of ledene (92), the aromadendren-9-one 135, which was isolated in 1971 from the shrub Phebalium squamulosum by Batey et al 43 and named`squamulosone'. Its enantiomer, called`millecrone B', was found recently in an extract of the nudibranch Leminda millecra.…”

Section: Aromadendrane Derivativesmentioning

confidence: 95%

Constituents of commercial Labdanum oil

et al. 1998

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Commercial Labdanum oil contains more than 300 constituents. 186 compounds (154 from the neutral part, 32 from the acidic part), representing about 95% of the oil, were identi®ed mainly by their NMR spectra. Typical for the Labdanum oil in the C 15 to C 20 region are aromadendrane (23%), cadinane (9%) and labdane (7%) derivatives, mostly oxidized. The main constituents in this region are ledene (92, 9.3%), allo-

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Section: Aromadendrane Derivativesmentioning

confidence: 95%

Constituents of commercial Labdanum oil

et al. 1998

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“…Hence, to the best of our knowledge, the purest natural source of dihydrotagetone is the essential oil of these two subspecies of P. glandulosum. [4] and Brophy et al [3a] did not yield squamulosone, a sesquiterpenoid ketone first reported by Batey et al [8] from P. squamulosum collected from Narrabeen, New South Wales. This Sydney Basin population belongs in the type subspecies, P. squamulosum subsp.…”

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confidence: 99%

Dihydrotagetone, an Unusual Fruity Ketone, is Found in Enantiopure and Enantioenriched Forms in Additional Australian Native Taxa of Phebalium (Rutaceae: Boronieae)

Sadgrove

Telford

Greatrex

et al. 2013

Natural Product Communications

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Here we report for the first time hydrodistillation of leaf essential oils from Phebalium squamulosum subsp. verrucosum, P. glandulosum subsp. eglandulosum, P. glandulosum subsp. nitidum and P. glandulosum subsp. angustifolium (Rutaceae: Boronieae). Essential oils were analysed using gas-chromatography/mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy (NMR). With the exception of P. glandulosum subsp. angustifolium, all taxa yielded essential oils in relatively high amounts (1-3%, w/w) made up predominantly of 2,6-dimethyloct-7-en-4-one (dihydrotagetone). The essential oil from P. squamulosum subsp. verrucosum contains either (+)-dihydrotagetone (ee 94-100%) or (-)-dihydrotagetone (ee 17-18%). Taxonomically, these results support the proposal that P. squamulosum subsp. verrucosum may be specifically misplaced, phytochemically resembling the P. glandulosum complex. Similarly, P. glandulosum subsp. angustifolium phytochemically resembles P. distans or P. longifolium and also appears to be assigned incorrectly to the P. glandulosum group.

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“…In the current study, squamulosone was detected at low concentration in the hydrodistilled EO but not at all in the DCM extracts most likely due to at a concentration lower than our minimum peak area used in quantification. Squamulosone, a sesquiterpene ketone, shares the same structural skeleton to the alcohol ledol [16,17]. Squamulosone has previously only been identified in extracts and essential oils from Phebalium squamulosum (Rutaceae), where it was first described [17,18].…”

Section: Gc-ms Analysismentioning

confidence: 99%

“…Squamulosone, a sesquiterpene ketone, shares the same structural skeleton to the alcohol ledol [16,17]. Squamulosone has previously only been identified in extracts and essential oils from Phebalium squamulosum (Rutaceae), where it was first described [17,18].…”

Section: Gc-ms Analysismentioning

confidence: 99%

Volatiles from the Rare Australian Desert Plant Prostanthera centralis B.J.Conn (Lamiaceae): Chemical Composition and Antimicrobial Activity

2014

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Hydrodistilled essential oils and dichloromethane (DCM) extracted volatiles were taken from cultivated specimens of Prostanthera centralis, endemic to central Australia. All volatiles were chemically characterised by Gas Chromatography-Mass Spectroscopy (GC-MS) with the use of authentic standards, followed by Nuclear Magnetic Resonance (NMR) Spectroscopy. The antimicrobial activity of the essential oils was measured against a range of Gram-negative and Gram-positive bacterial species using a micro-titre plate broth dilution assay. Twenty-two compounds were identified as components of the sweet smelling aromatic essential oil and DCM extracts, both showing a relatively high abundance of prostantherol. The volatiles extracted using DCM, differed only in the relative abundance of the major components and the lack of ledol and squamulosone. This study constitutes the first time ledol and squamulosone have been identified in a Prostanthera species. Antimicrobial assays showed moderate to high inhibitory activity against some Gram-positive bacteria and the yeast Candida albicans. OPEN ACCESSAgriculture 2014, 4 309

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The structure of squamulosone, a new sesquiterpene ketone from Phebalium squamulosum

Abstract: Squamulosone, C15H22O, a new sesquiterpene ketone occurring in Phebalium squamulosum, has been shown to have the structure (1) on chemical and spectroscopic evidence.

Cited by 18 publications

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Constituents of commercial Labdanum oil

Constituents of commercial Labdanum oil

Dihydrotagetone, an Unusual Fruity Ketone, is Found in Enantiopure and Enantioenriched Forms in Additional Australian Native Taxa of Phebalium (Rutaceae: Boronieae)

Volatiles from the Rare Australian Desert Plant Prostanthera centralis B.J.Conn (Lamiaceae): Chemical Composition and Antimicrobial Activity

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