Chemical Composition Of Lipophilic Extracts Research Articles

Characterization and Cytotoxicity Assessment of the Lipophilic Fractions of Different Morphological Parts of Acacia dealbata.

Acacia dealbata biomass, either from forest exploitation or from the management of invasive species, can be a strategic topic, namely as a source of high-value compounds. In this sense, the present study aimed at the detailed characterization of the lipophilic components of different morphological parts of A. dealbata and the evaluation of their cytotoxicity in cells representative of different mammals’ tissues. The chemical composition of lipophilic extracts from A. dealbata bark, wood and leaves was evaluated using gas chromatography-mass spectrometry (GC–MS). Terpenic compounds (representing 50.2%–68.4% of the total bark and leaves extracts, respectively) and sterols (60.5% of the total wood extract) were the main components of these extracts. Other constituents, such as fatty acids, long-chain aliphatic alcohols, monoglycerides, and aromatic compounds were also detected in the studied extracts. All the extracts showed low or no cytotoxicity in the different cells tested, demonstrating their safety profile and highlighting their potential to be used in nutraceutical or pharmaceutical applications. This study is therefore an important contribution to the valorization of A. dealbata, demonstrating the potential of this species as a source of high value lipophilic compounds.

Comparison of chemical composition of lipophilic extracts from Acacia mearnsii De Wild. wood of different ages

Acacia mearnsii De Wild. has been cultivated in Brazil mainly for the extraction of tannins from bark, but its wood has been used to complement the demand for hardwood in the pulp and paper industries. However, few studies have been carried out aiming to characterize the chemical composition of the wood lipophilic extracts from this species. Some compounds of these extract may generate sticky deposits in machinery in the paper and pulp mills, known as pitch. In general, woods with a higher content of lipophilic extracts generate more problems and damage caused by pitch deposits. So, this paper details the chemical composition of the lipophilic extracts of A. mearnsii woods of four ages (4, 7, 10 and 13-year-old) cultivated in Brazil. The wood from 7, 10 and 13-years-old trees showed similar amounts of lipophilic extracts ranging from 0.23 to 0.28 % (w/w). However, the 4-year-old wood presented more than twice that value i.e. 0.60 % (w/w). These lipophilic extracts were analyzed by GC–MS before and after alkaline hydrolysis, followed by derivatization. The main chemical classes found were fatty acids (27.1–95.0 mg kg−1), sterols (20.5–55.7 mg kg−1) and aromatic compounds (0.750–13.2 mg kg−1), followed by smaller amounts of long chain aliphatic alcohol (0.00–3.46 mg kg−1) and hydrocarbons (0.00–2.62 mg kg−1), before and after hydrolysis. The results showed that the wood extracts from 7, 10 and 13-year-old trees were similar from the quantitative and qualitative points of view, indicating that harvests over 7 years of age offer less propensity for pitch problems.

Characterizing the Chemical Composition of Lipophilic Extracts from Acacia mearnsii Wood

The chemical composition of Acacia mearnsii wood extract is described in this paper for the first time. This wood is cultivated in Brazil and has been used to complement the demand for hardwood in the pulp industry. In this study, we performed extractions with acetone (total extracts) and dichloromethane (lipophilic extracts responsible for the pitch formation), with the obtained percentages being 1.68 and 0.68%, respectively. The lipophilic extracts were derivatized and analyzed by Fourier transform infrared spectroscopy (FTIR) and gas chromatography-mass spectrometry (GC-MS) before and after alkaline hydrolysis. The results showed that 57 compounds were detected in the lipophilic extracts and these are mainly constituted by fatty acids ca. 32.8 mg kg-1 and sterols 26.9 mg kg-1. These chemical classes have always been present in pitch deposits in the pulp industry. Therefore, these results may be used by pulp mills to establish strategies for pitch control and represent an important advance in the knowledge of A. mearnsii.

Chemical composition of lipophilic extractives from six Eucalyptus barks

Barks show a large diversity in chemical composition and are generally characterized by a substantial content of extractives. Today, these components are viewed with a renewed interest as valuable source of chemicals and bioactive compounds. The barks of six eucalypt species, Eucalyptus botryoides, E. camaldulensis, E. maculata, E. rudis, E. sideroxylon and E. viminalis, were studied in relation to their lipophilic extractives that represented between 0.1% (E. rudis) and 1.8% (E. viminalis) of the oven-dry bark. It is the first time that a detailed chemical composition is given for the lipophilic extracts from the barks of these eucalypt species. They showed a high content in triterpenes (between 3623.1 and 13,616.5 mg/kg of bark), especially triterpenic acids such as betulinic, ursolic, oleanolic and arjunolic acids. Sterols were also identified in considerable amounts (174.0–1736.7 mg/kg of bark). β-Sitosterol was the major sterol, with 1350.1 mg/kg of bark in E. maculata. Fatty acids C16–C28 existed in smaller amounts. A saponification treatment (MeOH/KOH) showed that fatty acids, sterols and triterpenes existed in both esterified and non-esterified forms. The presence of triterpenes represents a potential added value for the valorization of bark residues by production of bioactive or high-value compounds.

Labdane-type diterpenoids from Juniperus communis needles

The chemical composition of lipophilic extractives from Juniperus communis used for cosmetic, medicinal and food additives was studied. Herein we report the extraction of labdane-type diterpenoids from the needles of the common juniper (Juniperus communis ssp. communis var. communis L.), and identification of them as the major class of compounds in this species. Furthermore, and to the best of our knowledge we provide the first-ever report some of these compounds (nor-16- imbricatolic, nor-16-acetylimbricatolic and acetylimbricatolic acids) as natural compounds. Imbricataloic and imbricatolic acids were the most abundant compounds, accounting for 65% of the total extract. We also found long-chain secondary alcohols (n-alkan-10-ols) and secondary/secondary alkanediols (4,10-, 5,10-, 6,10-, 7,10-), which we report here for the first time ever in the genus Juniperus. In total, we identified 127 compounds: of these, 48 (nonacosan-10- -tocopherols and lignans) are described here for the first time in Juniperus and 54 (including alkanols, phytol, sterols and flavonoids), for the first time in common juniper.

Chemical Composition of Lipophilic Extractives from Grey Alder (Alnus incana)

The chemical composition of the lipophilic extractives in the hexane extracts from grey alder bark, knotwood, and cones has been investigated by gas chromatography and gas chromatography-mass spectrometry. The efficiency of two extraction methods was compared. The highest amount of lipophilic extractives (about 9% of o.d. material) was observed in grey alder cone, while the lowest (about 3%) was found in knotwood. The three different morphological parts of alder showed significant differences not only in the content but also in composition of extractives, namely fatty acids, triglycerides, and triterpenes. The main identified compounds were triterpenoids (lupen-3-one, lupeol, betulone, betulinol, and betulinic acid) in bark, and triglycerides in cones. The major group in knotwood was free fatty acids (mainly linoleic acid, 18:2).

Chemical composition of lipophilic extractives from jute ( Corchorus capsularis) fibers used for manufacturing of high-quality paper pulps

The chemical composition of the lipophilic extractives from jute ( Corchorus capsularis) fibers, which are used for high-quality paper pulp manufacturing, was thoroughly studied. The extractives content was low (0.4%), and its composition was studied by gas chromatography–mass spectrometry. For a better characterization of the different homologous series and compounds present in minor amounts, the extract was also fractionated by solid-phase extraction. The most predominant lipophilic compounds present in jute fibers were high molecular weight ester waxes (24% of total extract), followed by free fatty acids (17%), free fatty alcohols (17%) and α-hydroxyfatty acids (14%). Additionally, significant amounts of alkanes (6%), ω-hydroxyfatty acids (6%), sterols (6%), steroid and triterpenoid ketones (3%) and steryl glycosides (1%) were also identified, together with minor amounts of mono- and diglycerides.

Chemical composition of lipophilic extractives from sisal ( Agave sisalana) fibers

The chemical composition of lipophilic extractives from sisal ( Agave sisalana) fibers, which are used for high-quality paper pulp production, was studied. The lipophilic extract, which accounted for 0.5% of total sisal fiber weight, was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS) using short- and medium-length high temperature capillary columns, respectively. For a more detailed characterization, the extract was fractionated by solid-phase extraction and the fractions obtained were analyzed by GC and GC/MS. The most predominant compounds identified were fatty acids (30% of total lipids) including α- and ω-hydroxyfatty acids, fatty alcohols (20%), free sterols (11%), alkanes (11%) and a series of ferulic acid esters of long chain alcohols and ω-hydroxyfatty acids (10%). Additionally, steroid hydrocarbons and ketones, monoglycerides, aldehydes, waxes, and sterol glycosides were also found together with minor amounts of diglycerides, and sterol esters.

Effect of storage time on the composition and content of wood extractives in Eucalyptus cultivated in Brazil

Lipophilic wood extractives commonly referred to as pitch, cause significant problems for the pulp and paper industries. The reduction of these extractives is an important aspect that concerns industries around the world. In the present work the change in the amount and chemical composition of lipophilic extractives from Eucalyptus spp. stored for 20, 40, 60, 100, 140 and 180 days after harvesting was investigated. The results showed a decrease in extractives content with storage time, with the most significant decrease occurring 60 days after harvesting. In addition, fatty acids and sterols were the main classes of compounds responsible for the significant decrease in extractive content. Data were analyzed by principal component analysis. PC1 explains approximately 99% of the total variance, and β-sitosterol was the major compound responsible for the differentiation. These studies demonstrate that in terms of economical aspects, quality of the pulp and paper and minimization of pitch formation, the best period of wood storage is 60 days.

Chemical characterization of the lipophilic fraction of giant reed ( Arundo donax) fibres used for pulp and paper manufacturing

The chemical composition of lipophilic extractives from Arundo donax stems (including nodes and internodes), used for pulp and papermaking, was studied. The lipid fraction was extracted with acetone and redissolved in chloroform, and then fractionated by solid-phase extraction (SPE) on aminopropyl-phase cartridges into four different fractions of increasing polarity. The total lipid extract and the resulting fractions were analysed by gas chromatography and gas chromatography/mass spectrometry, using short- and medium-length high-temperature capillary columns, respectively. The main compounds identified in the fibres included series of long-chain n-fatty acids, n-alkanes, n-aldehydes, n-alcohols, monoglycerides, free and esterified sterols and triterpenols, steryl glucosides, steroid hydrocarbons and steroid and triterpenoid ketones. Minor amounts of other compounds such as diglycerides, waxes and tocopherols were also identified among the lipids of A. donax.

Chemical composition of lipophilic extractives released during the hot water treatment of wheat straw.

Treatment of wheat straw with hot water at 80-95 degrees C for 0.5 h at pH 6.0-8.0 released 41.0-53.0% of the original lipophilic extractives. The chemical compositions of six lipophilic extractives were determined by GC on a medium-length high-temperature capillary column without derivatization, thus giving a method for direct determination of individual components of free fatty and resin acids, sterols, waxes, sterol esters, and triglycerides. The extracts contained 68.7-75.8% lipophilic substances, comprising mainly free fatty acids (25.8-48.4%), waxes (9.4-27.0%), sterols (4.1-8.0%), triglycerides (3.3-11.0%), and sterol esters (2.6-5.1%). Minor amounts of diglycerides (0.3-0.5%), resin acid (0.5-3.1%), and phenolic compounds (0.9-3.6%) were also quantitatively determined in the extractives.

Lipophilic extractives in process waters during manufacturing of totally chlorine free kraft pulp from eucalypt wood

The chemical composition of lipophilic extractives from process waters throughout a totally chlorine free (TCF) bleaching sequence after kraft pulping of eucalypt wood has been studied. These compounds are among the most problematic wood constituents for both TCF and zero liquid effluent (ZLE) processes, since they tend to accumulate in circuits resulting in the formation of the so-called pitch deposits causing serious problems in the pulp and paper industry. Pitch deposits collected at different parts of the pulp mill were also characterized and their composition compared with that of lipophilic compounds in process waters and Eucalyptus globulus wood. The identification of these compounds from process waters, wood and pitch deposits was performed by gas chromatography and gas chromatography–mass spectrometry using short- and medium-length high temperature capillary columns. Sterols, sterol esters, steroid ketones and steroid hydrocarbons were the main compounds identified. These chemical species arise from eucalypt wood extractives that survive the pulping and are released from pulp into the process waters during the bleaching process. Finally, they can deposit in pulp and on different parts of the mill or remain suspended in process waters being discharged in effluents.

Lipophilic Extractives from Eucalyptus globulus Pulp during Kraft Cooking Followed by TCF and ECF Bleaching

SummaryThe chemical composition of lipophilic extractives in paper pulps fromEucalyptus globuluswood during kraft cooking followed by TCF (“totally chlorine free”) and ECF (“elemental chlorine free”) bleaching sequences has been determined by gas chromatography and gas chromatography-mass spectrometry. The chemical analyses revealed that the composition of the lipophilic extractives in pulp after kraft cooking and TCF bleaching with hydrogen peroxide was similar to that ofE. globuluswood extractives, sitosterol and sitosterol esters being the predominant compounds. In contrast, the presence of these compounds was almost negligible in pulp after ECF bleaching with chlorine dioxide and only the saturated sterol stigmastanol, in both free and esterified forms, survived the bleaching.

Chemical Composition of Lipophilic Extractives from Eucalyptus globulus Labill. Wood

Summary The composition of lipophilic extractives in the chloroform soluble fraction of the acetone extract from Eucalyptus globulus wood has been examined. The lipid extract was fractionated by solid-phase extraction on aminopropyl-phase cartridges into four different fractions of increasing polarity. The total lipid extract and the resulting fractions were analyzed by gas chromatography and gas chromatography-mass spectrometry, using high temperature capillary columns. The main compounds identified included sterols, sterol esters, fatty acids, steroid ketones, hydrocarbons and triglycerides. Minor compounds such as fatty alcohols, mono- and diglycerides, waxes and tocopherols were also identified among the lipids from E. globulus wood.