New compounds from the essential oil of <i>Vetiveria nigritana</i> roots from Mali

Champagnat, Pascal; Bessière, Jean‐Marie; Chezal, Jean‐Michel; Chalchat, Jean‐Claude; Carnat, A.

doi:10.1002/ffj.1828

Cited by 10 publications

(15 citation statements)

References 17 publications

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“…Compound 3 was isolated from F1 after several column chromatographies with ~70% overall purity only, but it provided both EI/MS and NMR data in all respects identical to those previously reported by Champagnat et al . for nigritene . However, the structure described by these authors for nigritene was found to correspond better to that we obtained for compound 2 rather than for compound 3 .…”

Section: Resultssupporting

confidence: 73%

“…Champagnat et al . previously suggested nigritene as being formed upon push–pull decarboxyaltion of a parent sesquiterpenic acid.…”

Section: Resultsmentioning

confidence: 99%

“…reported in this journal the isolation and characterization of two norsesquiterpenes from the essential oil of the so‐called ‘African’ vetiver ( Chrysopogon nigritanus Benth.) . These norsesquiterpenes were named nigritene and dehydronigritene after the formerly used taxonomy of the plant, Vetiveria nigritana .…”

Section: Introductionmentioning

confidence: 99%

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Norsesquiterpenes as markers of overheating in Indonesian vetiver oil

Filippi

2013

Flavour & Fragrance J

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Vetiver oil from Indonesia (Java type) is characterized by the occurrence of a relatively large series of norsesquiterpenes compared with vetiver oils of other origins. Three major norsesquiterpenes have been isolated from this essential oil and their structures have been elucidated by one‐dimensional and two‐dimensional nuclear magnetic resonance and mass spectrometry. Two of them were characterized for the first time, while the third has been reconsidered from the point of view of its relative configuration. Moreover, we clearly demonstrate that these compounds are generated upon thermic degradation of vetiver acids, making them potential markers of overheating during hydrodistillation. Copyright © 2013 John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 73%

“…Champagnat et al . previously suggested nigritene as being formed upon push–pull decarboxyaltion of a parent sesquiterpenic acid.…”

Section: Resultsmentioning

confidence: 99%

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Norsesquiterpenes as markers of overheating in Indonesian vetiver oil

Filippi

2013

Flavour & Fragrance J

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“…Stapf (Poaceae) or black vetivergrass is a robust perennial grass growing from Mauritania to Nigeria and through to north-eastern, eastern and southern tropical Africa [1]. V. nigritana is a grass with short rhizomes which form compact tufts with numerous upright leaves.…”

Section: Introductionmentioning

confidence: 99%

“…V. nigritana roots are also used in the treatment of stomach aches in Nigeria [3]. The chemical composition of the essential oil of Vetiveria nigritana roots from different localities has already been elucidated by some studies revealing a variability of the constituents of this essential oil [1,[4][5][6]. Few investigations have been found on the chemical composition and biological properties of V. nigritana from Burkina Faso.…”

Section: Introductionmentioning

confidence: 99%

Chemical composition, antioxidant and antimicrobial activities of the essential oil of Vetiveria nigritana (Benth.) Stapf roots from Burkina Faso

Semde¹,

Koudou²,

Zongo³

et al. 2017

J App Biol Biotech

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The main objective of this study was to determine the chemical composition, antioxidant and antimicrobial properties of the essential oil of Vetiveria nigritana (Benth.) Stapf roots growing in Burkina Faso. The composition of the essential oil was analyzed by GC and GC / MS. DPPH radical scavenging method and FRAP test were used to demonstrate the antioxidant activity of the essential oil. Antimicrobial activity of the essential oil was determined using disk diffusion method and broth microdilution method. The major components of the essential oil of V. nigritana were dehydronigritene, zizanoic acid, preziza-7-(15)-en-3-ol, khusian-2-ol, ziza-6(13)-en-3-beta-ol, prezizaan-15-al and khusimone. The essential oil demonstrated weak radical scavenging power with an IC50 of 28.35±0.58µl and a low reduction capacity. The essential oil showed a relative good inhibitory action against strains of Bacillus, Escherichia coli, Staphylococcus, Clostridium perfringens, Listeria monocytogenes, Micrococcus luteus, Enterococcus faecalis, Candida kefir and Saccharomyces cerevisiae with inhibition diameters ranging from 11.5±0.71 mm to 23.5±0.71 mm. Minimum inhibitory concentrations of the essential oil of V. nigritana ranged from 1% to 8%, minimum bactericidal concentrations from 2% to 4% with minimum fungicidal concentration of 4%. These results suggest that essential oil of V. nigritana roots could be subjected for pharmaceutical drug formulations.

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Highly Stereocontrolled Total Syntheses of Cedrane Sesquiterpenes via Cascade [5+2] Cycloaddition/Etherification

Zhang

Chi

et al. 2021

Chin. J. Chem.

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Cedrane sesquiterpenes possess common tricyclo [5.3.1.0 1,5 ]undecane core structure. The varied oxa-five-membered ring decorating their core structure to form 8-oxa-tetracyclo[7.2.2.0 1,5 .0 6,13]tridecane framework, containing six consecutive chiral centers (including two all-carbon quaternary centers and one oxygenated quaternary carbon center), has proven to be a synthetic challenge and a biosynthetic mystery to date. Herein, we reported a distinct and biomimetic strategy to these sesquiterpenes resulting in the concise asymmetric total syntheses of three cedrane sesquiterpenes from simple commercially available building blocks. Key feature is exploitation of a cascade oxidative dearomatization-induced [5+2] cycloaddition/etherification to highly stereocontrolled construct 8-oxa-tetracyclo[7.2.2.0 1,5 .0 6,13]tridecane framework with five contiguous chiral centers in one step. In addition, a metal-free I 2 -catalyzed and DMSO-mediated oxidative dehydroaromatization was applied to prepare curcuphenol and its derivatives from the highly functionalized cyclohexenones with minimal manipulations.

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New compounds from the essential oil of Vetiveria nigritana roots from Mali

Cited by 10 publications

References 17 publications

Norsesquiterpenes as markers of overheating in Indonesian vetiver oil

Norsesquiterpenes as markers of overheating in Indonesian vetiver oil

Chemical composition, antioxidant and antimicrobial activities of the essential oil of Vetiveria nigritana (Benth.) Stapf roots from Burkina Faso

Highly Stereocontrolled Total Syntheses of Cedrane Sesquiterpenes via Cascade [5+2] Cycloaddition/Etherification

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