Azulenes, Costols and Γ-Lactones from Cypress-Pines (<i>Callitris columellaris, C. glaucophylla</i>and<i>C. intratropica</i>) Distilled Oils and Methanol Extracts

Doimo, Luigino

doi:10.1080/10412905.2001.9699594

Cited by 23 publications

(10 citation statements)

References 5 publications

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“…-lactones [19] are also present and aid termite resistance [20]. Guaiol and azulenes have higher relative abundances in the essential oils, while costols and 3 of 16 ers of Callitris predominantly consist of guaiol [17], along with other es [18], which are responsible for the blue colour of material referred il (guaiazulene, chamazulene). Costols [18] and ƴ-lactones [19] are also ance [20].…”

Section: Chemistry Of South African Widdringtoniamentioning

confidence: 99%

“…The overwhelmingly higher representation of ut consistent across all specimens and species not isolated in the earlier studies that focused on cted to branching parts and sesquiterpenes are inantly consist of guaiol [17], along with other onsible for the blue colour of material referred zulene). Costols [18] and ƴ-lactones [19] are also zulenes have higher relative abundances in the strongly represented in solvent extracts [20] due ris spp. also reported diterpene acids using mass ential oils from Callitris and Widdringtonia are monoterpenes predominating in leaf oils and er oils.…”

Section: Chemistry Of South African Widdringtoniamentioning

confidence: 99%

“…Essential oils from leaves of the two species of Callitris sampled in the current study (C. endlicheri and C. columellaris) have been previously characterised [16,27]. Furthermore, timber essential oils and solvent extracts have also been studied [18]. Thus, in the current study, an examination of solvent extracted (non-volatile) components from the leaves was undertaken to gratify this neglected area of research in order to make a comparison to Widdringtonia.…”

Section: Chemistry Of Callitrismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Essential oils from timbers of Callitris predominantly consist of guaiol [17], along with other sesquiterpenes such as azulenes [18], which are responsible for the blue colour of material referred to as C. intratropica essential oil (guaiazulene, chamazulene). Costols [18] and ƴ-lactones [19] are also present and aid termite resistance [20]. Guaiol and azulenes have higher relative abundances in the essential oils, while costols and ƴ-lactones are more strongly represented in solvent extracts [20] due to their higher boiling points.…”

Section: Introductionmentioning

confidence: 99%

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New Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae)

et al. 2020

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In spite of the evidence for antimicrobial and acaricidal effects in ethnobotanical reports of Callitris and Widdringtonia, the diterpene acids from Widdringtonia have never been described and no comparison to the Australian clade sister genus Callitris has been made. The critically endangered South African Clanwilliam cedar, Widdringtonia wallichii (syn. W. cedarbergensis), of the Cederberg Mountains was once prized for its enduring fragrant timbers and an essential oil that gives an aroma comparable to better known Mediterranean cedars, predominantly comprised by widdrol, cedrol, and thujopsene. In South Africa, two other ‘cedars’ are known, which are called W. nodiflora and W. schwarzii, but, until now, their chemical similarity to W. wallichii has not been investigated. Much like Widdringtonia, Callitris was once prized for its termite resistant timbers and an ‘earthy’ essential oil, but predominantly guaiol. The current study demonstrates that the essential oils were similar across all three species of Widdringtonia and two known non-volatile diterpene acids were identified in leaves: the pimaradiene sandaracopimaric acid (1) and the labdane Z-communic acid (2) with a lower yield of the E-isomer (3). Additionally, in the leaves of the three species, the structures of five new antimicrobial labdanes were assigned: 12-hydroxy-8R,17-epoxy-isocommunic acid (4), 8S-formyl-isocommunic acid (5), 8R,17-epoxy-isocommunic acid (6), 8R-17R-epoxy-E-communic acid (7), and 8R-17-epoxy-E-communic acid (8). Australian Callitris columellaris (syn. C. glaucophylla) also produced 1 and its isomer isopimaric acid, pisiferal (9), and pisiferic acid (10) from its leaves. Callitris endlicheri (Parl.) F.M.Bailey yielded isoozic acid (11) as the only major diterpene. Diterpenes 4–6, pisiferic acid (10), spathulenol, and guaiol (12) demonstrated antimicrobial and acaricidal activity.

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Section: Chemistry Of South African Widdringtoniamentioning

confidence: 99%

Section: Chemistry Of South African Widdringtoniamentioning

confidence: 99%

Section: Chemistry Of Callitrismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae)

et al. 2020

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Classical Techniques for Extracting Essential Oils from Plants

2023

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Antifungal Activity of the Essential Oils of Callitris neocaledonica and C. sulcata Heartwood (Cupressaceae)

Waikedre¹,

Vitturo

Molina

et al. 2012

Chemistry & Biodiversity

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Mortality due to fungal infections has increased substantially, becoming a worldwide problem in public health. As a contribution to the discovery of new antifungal agents, the properties of the heartwood essential oils of two trees growing in New Caledonia, Callitris neocaledonica and C. sulcata (Cupressaceae) were investigated. The essential oils extracted by hydrodistillation were characterized by GC-FID and GC/MS analyses. From C. neocaledonica oil, 31 constituents were identified, representing 97.0% of the total oil composition, which was mainly constituted by oxygenated sesquiterpenes (88%). Among them, guaiol (1; 30.2%), bulnesol (2; 12.5%), α-eudesmol (3; 10.5%), β-eudesmol (4; 10.5%), γ-eudesmol (10.2%), and elemol (4.9%) predominated. The chemical composition of C. sulcata oil, from which 39 constituents were identified (96.8% of the total oil composition), showed some similarities with that of C. neocaledonica oil. The major constituents were also oxygenated sesquiterpenes, accounting for 78.5% of the oil, amongst them, mainly compounds 1 (16.1%), 3 and 4 (9.7% each), as well as 2 (7.4%). The antifungal activity of the oils against clinical isolates of four dermatophytic fungi (Trichophyton mentagrophytes, T. rubrum, Microsporum canis, and M. gypseum) and six yeasts (Candida albicans, C. parapsilosis, C. glabrata, C. krusei, Cryptococcus neoformans, and Cryptococcus gattii) was tested by determining minimum inhibitory concentrations (MICs) using the microdilution method. The best antifungal activities of the C. neocaledonica and C. sulcata oils were obtained against C. krusei (MICs of 3.9 and 0.975 μg/ml, resp.). These MIC values were similar to those of the reference drugs itraconazole and fluconazole (1.0 and 0.5 mg/ml, resp.). The oils were also subjected to a screening for their possible DPPH(.) (2,2-diphenyl-1-picrylhydrazyl) radical-scavenging activity. C. neocaledonica essential oil was more active than C. sulcata oil (93.3 vs. 32.2% DPPH(.) scavenged at 250 μg/ml).

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Azulenes, Costols and Γ-Lactones from Cypress-Pines (Callitris columellaris, C. glaucophyllaandC. intratropica) Distilled Oils and Methanol Extracts

Cited by 23 publications

References 5 publications

New Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae)

New Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae)

Classical Techniques for Extracting Essential Oils from Plants

Antifungal Activity of the Essential Oils of Callitris neocaledonica and C. sulcata Heartwood (Cupressaceae)

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