High-speed countercurrent chromatography as a tool to isolate nerolidol from the<i>Baccharis dracunculifolia</i>volatile oil

Queiroga, Carmen Lucia; Cavalcante, M.Q.; Ferraz, Paola; Coser, R.N.; Sartoratto, Adilson; Magalhães, Pedro Melillo de

doi:10.1080/10412905.2014.922511

Cited by 6 publications

(5 citation statements)

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“…The major compounds of B. dracunculifolia leaf and flower essential oils in our study were mainly nerolidol and spathulenol, corroborating the literature on this plant (Massignani et al, 2009;Queiroga et al, 2014). In addition, Lage et al (2015) reported that the essential oil from B. dracunculifolia fresh aerial parts (leaves) from Viçosa, Brazil, had nerolidol…”

Section: Discussionsupporting

confidence: 90%

Baccharis dracunculifolia DC (Asteraceae) leaf and flower essential oils to control Rhipicephalus microplus Canestrini (Arachnida: Ixodidae) in the free-living stage

Cazella

Oliveira

Bortolucci

et al. 2020

RSD

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Baccharis dracunculifolia, native to Brazil and the main source of “green propolis”, has been reported with several biological activities, and may be a source of bovine tick control substituting synthetic acaricides. Objective: to evaluate the in vitro and ex situ acaricidal activity of B. dracunculifolia leaf and flower essential oils against Rhipicephalus microplus. Methodology: the essential oils were extracted by hydrodistillation and analyzed by a gas chromatography coupled to mass spectrometry; the acaricidal activity of the essential oil was evaluated in vitro against adult females and against the egg hatchability; moreover, the acaricidal activity against tick larvae was evaluated in vitro and ex situ. Results: the major class of the essential oils was oxygenated sesquiterpene (55.1% leaves 50.4% flowers) and the main compounds were (21.5% leaves; 20.6% flowers) and spathulenol (21.8% leaves; 20.3% flowers). The essential oil at 500 mg/mL was effective to control egg hatchability with a reduction of egg laying capacity and decrease of number of adult ticks and larvae. The larvicidal activity of the essential oil had LC99.9 from 35 to 37 mg/mL by probit analysis, and the essential oil from 11 to 14 mg/mL presented 85 to 95% of treatment efficiency in the ex situ test. Conclusion: B. dracunculifolia leaf and flower essential oils are stable and have application potential to control bovine ticks.

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Section: Discussionsupporting

confidence: 90%

Baccharis dracunculifolia DC (Asteraceae) leaf and flower essential oils to control Rhipicephalus microplus Canestrini (Arachnida: Ixodidae) in the free-living stage

Cazella

Oliveira

Bortolucci

et al. 2020

RSD

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“…The system would be run in the normal phase (NP) elution mode (with an organic non-polar phase as the mobile phase), with waxes eluting with the solvent front. Several solvent systems ( Table 1 ) obtained from the literature [ 21 , 22 , 23 ], as well as a standard approach used by the authors, were tested. A short HPLC–UV method modified from the authors’ earlier UPLC–MS method [ 19 ] was developed for a rapid screening of CCC fractions and was used to establish that the peak of 14.418 min could be used as a KD = 1 marker for method development ( Figure S1, Supplementary Material ).…”

Section: Resultsmentioning

confidence: 99%

“…This result can be explained by the presence of ethyl acetate, which makes HEMWat 23 more polar. The HMWat 2 (5:4:1 v / v / v ) solvent system was previously used to isolate a metabolite from the essential oil of one of the plant sources of Brazilian green propolis [ 23 ], but obtaining the essential oil is a purification step which was not performed in this study, and green propolis is chemically different from red propolis.…”

Section: Resultsmentioning

confidence: 99%

“…A similar approach was employed for the separation of 711 mg of floral resins from a hexane extract of Clusia fluminensis flowers, producing the prenylated benzophenone, clusianone, using an n-hexane–acetonitrile–methanol (2:1.25:0.5 v / v / v ) solvent system, within 2 h on a 125 mL column [ 22 ]. CCC was also used to isolate nerolidol from 500 mg of the essential oil of Baccharis dracunculifolia leaves, using a hexane–methanol–water (5:4:1 v / v / v ) system, within 40 min, on a 118 mL column [ 23 ]. These results suggest that CCC can be used to fractionate Brazilian red propolis extracts at a preparative scale.…”

Section: Introductionmentioning

confidence: 99%

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Preparative Fractionation of Brazilian Red Propolis Extract Using Step-Gradient Counter-Current Chromatography

Lopez,

Marcucci,

Rocco

et al. 2024

Molecules

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Propolis is a resinous bee product with a very complex composition, which is dependent upon the plant sources that bees visit. Due to the promising antimicrobial activities of red Brazilian propolis, it is paramount to identify the compounds responsible for it, which, in most of the cases, are not commercially available. The aim of this study was to develop a quick and clean preparative-scale methodology for preparing fractions of red propolis directly from a complex crude ethanol extract by combining the extractive capacity of counter-current chromatography (CCC) with preparative HPLC. The CCC method development included step gradient elution for the removal of waxes (which can bind to and block HPLC columns), sample injection in a single solvent to improve stationary phase stability, and a change in the mobile phase flow pattern, resulting in the loading of 2.5 g of the Brazilian red propolis crude extract on a 912.5 mL Midi CCC column. Three compounds were subsequently isolated from the concentrated fractions by preparative HPLC and identified by NMR and high-resolution MS: red pigment, retusapurpurin A; the isoflavan 3(R)-7-O-methylvestitol; and the prenylated benzophenone isomers xanthochymol/isoxanthochymol. These compounds are markers of red propolis that contribute to its therapeutic properties, and the amount isolated allows for further biological activities testing and for their use as chromatographic standards.

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“…As shown in Table 2, HPLC and GC are commonly used as offline detectors for the initial identification and purity assessments of separated products [67]. They are often equipped with ultraviolet (UV) detectors and diode array detectors (DAD) for scanning and screening the separated fractions, thereby reducing sample loss during detection and enhancing product identification efficiency [31]. In addition, an evaporative light scattering detector (ELSD) serves as an alternative to UV and DAD for products that lack or exhibit weak UV absorption properties.…”

Section: Common Hsccc Detectors For Eo Separationmentioning

confidence: 99%

Research Progress in the Separation of Chemical Components from Essential Oils by High-Speed Countercurrent Chromatography

He,

Zhong,

Zhang

et al. 2024

Separations

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Essential oils (EOs) are vital secondary metabolites in plants. They have garnered substantial attention owing to their distinct flavors and desirable attributes, including potent antioxidant, antibacterial, and antitumor properties. Nevertheless, the active constituents of EOs exhibit intricate chemical structures, and conventional separation techniques are inadequate for purifying the individual chemical components from EOs. High-speed countercurrent chromatography, based on the principles of a hydrodynamic equilibrium system, has emerged as a liquid–liquid chromatographic separation method renowned for its ability to handle substantial single injection volumes and the absence of irreversible adsorption. Consequently, in recent years, this technique has been widely employed in the isolation and refinement of natural products. In this review, a comprehensive analysis is conducted, contrasting the merits and demerits of high-speed countercurrent chromatography with conventional separation methods. The solvent systems, elution modes, commonly employed detectors, and practical applications are reviewed in the context of high-speed countercurrent chromatography for essential oil separation and purification. Furthermore, this review offers a glimpse into the potential prospects of applying this technique, with the intention of serving as a valuable reference for the use of high-speed countercurrent chromatography in the purification of EOs.

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High-speed countercurrent chromatography as a tool to isolate nerolidol from theBaccharis dracunculifoliavolatile oil

Cited by 6 publications

References 8 publications

Baccharis dracunculifolia DC (Asteraceae) leaf and flower essential oils to control Rhipicephalus microplus Canestrini (Arachnida: Ixodidae) in the free-living stage

Baccharis dracunculifolia DC (Asteraceae) leaf and flower essential oils to control Rhipicephalus microplus Canestrini (Arachnida: Ixodidae) in the free-living stage

Preparative Fractionation of Brazilian Red Propolis Extract Using Step-Gradient Counter-Current Chromatography

Research Progress in the Separation of Chemical Components from Essential Oils by High-Speed Countercurrent Chromatography

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