Identification of New Hydroxy Fatty Acids and Ferulic Acid Esters in the Wood of Eucalyptus globulus

Holzforschung ◽  
2002 ◽  
Vol 56 (2) ◽  
pp. 143-149 ◽  
Author(s):  
C. S. R. Freire ◽  
A. J.D. Silvestre ◽  
C. Pascoal Neto
Keyword(s):  
Fatty Acids ◽  
Chemical Composition ◽  
Ferulic Acid ◽  
Eucalyptus Globulus ◽  
Fatty Alcohols ◽  
Hydroxy Fatty Acids ◽  
Gas Chromatography Mass Spectrometry ◽  
Published Data ◽  
First Time ◽  
Acid Esters

Summary The chemical composition of the dichloromethane extract of Eucalyptus globulus wood cultivated in Portugal was studied by gas chromatography-mass spectrometry, prior to and after alkaline hydrolysis. In addition to previously identified lipophilic extractives, 22 free or esterified compounds (14 fatty acids, 2 fatty alcohols and 6 aromatic compounds) were identified for the first time in E. globulus wood. One of these, ferulic acid, was esterified with three different fatty alcohols and with two α-hydroxyfatty acids. Some of the newly identified compounds, particularly the a-hydroxy-fatty acids are responsible for recently reported pitch problems during pulp production in a Portuguese mill. The differences found in the E. globulus chemical composition, when compared with published data, are expected to be related to variations in the location of growth and genetic factors.

Lipophilic Extractives of the Inner and Outer Barks of Eucalyptus globulus

Holzforschung ◽  
2002 ◽  
Vol 56 (4) ◽  
pp. 372-379 ◽  
Author(s):  
C. S. R. Freire ◽  
A. J. D. Silvestre ◽  
C. Pascoal Neto ◽  
J.A.S. Cavaleiro
Keyword(s):  
Mass Spectrometry ◽  
Eucalyptus Globulus ◽  
Gas Chromatography Mass Spectrometry ◽  
Bark Extract ◽  
Chemical Compositions ◽  
Outer Bark ◽  
Inner Bark ◽  
Triterpenic Acids ◽  
First Time ◽  
Acid Esters

Summary The chemical compositions of the dichloromethane extracts of inner and outer barks of E. globulus were studied by gas chromatography-mass spectrometry. The two fractions show very different chemical compositions: triterpenic acids, such as betulinic, ursolic and oleanolic acids, were the major components of the outer bark extract, whereas β-sitosterol and β-amirin along with palmitic, linoleic and oleic acids predominate in the inner bark extract. Several α-and β-hydroxy fatty acids, recently reported for the first time as E. globulus wood components, were also identified in the outer and inner barks. In the outer bark extract, minor amounts of ferulic acid esters, also previously reported to occur in E. globulus wood were identified. In general, the inner bark lipophilic extractives resemble more closely that of E. globulus wood.

scholarly journals Soil and Leaf Nutrients Drivers on the Chemical Composition of the Essential Oil of Siparuna muricata (Ruiz & Pav.) A. DC. from Ecuador

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2949
Author(s):  
Juan I. Burneo ◽  
Ángel Benítez ◽  
James Calva ◽  
Pablo Velastegui ◽  
Vladimir Morocho
Keyword(s):  
Gas Chromatography ◽  
Chemical Composition ◽  
Secondary Metabolites ◽  
Essential Oil ◽  
Chemical Elements ◽  
Climatic Conditions ◽  
Gas Chromatography Mass Spectrometry ◽  
Chemical Compositions ◽  
Leaf Nutrients ◽  
First Time

Chemical compositions of plants are affected by the initial nutrient contents in the soil and climatic conditions; thus, we analyzed for the first time the effects of soil and leaf nutrients on the compositions of the essential oils (EOs) of Siparuna muricata in four different localities in Ecuador. EOs were obtained by hydrodistillation and analyzed by gas chromatography/mass spectrometry (GC/MS) and a gas chromatography/flame ionization detector (GC/FID). Enantiomeric distribution by GC/MS was determined, modifying the enantiomeric separation of β-pinene, limonene, δ-elemene, β-bourbonene, cis-cadina-1 (6), 4-diene and atractylone. A total of 44 compounds were identified. The most representative for L1 were guaiol, atractylone and 4-diene; for L2, cis-cadina-1(6),4-diene and myrcene; for L3, atractylone, myrcene and germacrene B; and finally, L4 germacrene B, myrcene and cis-cadina-1(6),4-diene. Correlations between soil- leaf chemical elements such as Al, Ca, Fe, Mg, Mn, N and Si in the different localities were significant with chemical composition of the essential oil of Siparuna muricata; however, correlations between soil and leaf K, P, and Na were not significant. Cluster and NMDS analysis showed high dissimilarity values of secondary metabolites between four localities related with changes in soil- leaf nutrients. Thus, the SIMPER routine revealed that not all secondary metabolites contribute equally to establishing the differences in the four localities, and the largest contributions are due to differences in guaiol, cis-cadina-1(6),4-diene, atractylone and germacrene. Our investigation showed for the first time the influences of altitude and soil- leaf chemical elements in the chemical composition of the EOs of S. muricata.

scholarly journals Cuticular and Internal Chemical Composition of Biting Midges Culicoides spp. (Diptera: Ceratopogonidae), Potential Vectors of Viral Diseases

2014 ◽  
Vol 9 (8) ◽  
pp. 1934578X1400900
Author(s):  
Mikel González ◽  
Sergio López ◽  
Gloria Rosell ◽  
Arturo Goldarazena ◽  
Angel Guerrero
Keyword(s):  
Chemical Composition ◽  
Gas Chromatography Mass Spectrometry ◽  
Viral Diseases ◽  
Chemical Profile ◽  
Biting Midges ◽  
Biting Midge ◽  
Branched Hydrocarbons ◽  
Hexane Extracts ◽  
Major Chemical ◽  
First Time

The chemical profile of the cuticle and internal tissues of four species of Culicoides have been studied for the first time by gas chromatography-mass spectrometry. The chemical composition of females of C. obsoletus s.l. and C. lupicaris, vectors of diverse viral diseases, have been compared with that of other biting midges, such as C. kibunensis and C. fascipennis, and the non-biting midge Forcipomyia bipunctata. A total of 61 compounds belonging to 8 major chemical classes were identified in cuticular and internal tissues in n-hexane extracts. The compounds include carboxylic acids (CAs) (C6-C20), with C16:0, C16:1 and C18:1 being dominant, branched hydrocarbons (C29 to C38 mono/di/trimethylalkanes), linear hydrocarbons (C15 to C33, mainly odd chain carbons), terpenes (geranylacetone, geranylgeraniol acetate, squalene, terpenic alcohol), steroids (cholesterol), aldehydes (C9-C10 and even chain C20 to C30), and esters. The chemical profile depends on the species and whether the extracts are external (cuticle) or internal. The contents of linear and branched hydrocarbons and aldehydes was high in cuticular extracts but practically absent in internal tissues, which were, in contrast, rich in CAs, terpenes and steroids. The results are discussed and compared with other Culicoides midges and mosquito-related species.

scholarly journals Impact of Selected Cosmetic Ingredients on Common Microorganisms of Healthy Human Skin

Cosmetics ◽  
2019 ◽  
Vol 6 (3) ◽  
pp. 45 ◽  
Author(s):  
Dorota Dobler ◽  
Thomas Schmidts ◽  
Sören Wildenhain ◽  
Ilona Seewald ◽  
Michael Merzhäuser ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Human Skin ◽  
Chain Length ◽  
Skin Diseases ◽  
Free Acid ◽  
Fatty Alcohols ◽  
Fatty Acid Esters ◽  
Bacterial Strains ◽  
Acid Esters

Human skin is a complex ecosystem and is host to a large number of microorganisms. When the bacterial ecosystem is balanced and differentiated, skin remains healthy. However, the use of cosmetics can change this balance and promote the appearance of skin diseases. The skin’s microorganisms can utilize some cosmetic components, which either promote their growth, or produce metabolites that influence the skin environment. In this study, we tested the ability of the Malassezia species and some bacterial strains to assimilate substances frequently used in dermal formulations. The growth capability of microorganisms was determined and their lipase activity was analyzed. The growth of all Malassezia spp. in the presence of free acids, free acid esters, and fatty alcohols with a fatty chain length above 12 carbon atoms was observed. No growth was observed in the presence of fatty alcohol ethers, secondary fatty alcohols, paraffin- and silicon-based substances, polymers, polyethylene glycols, quaternary ammonium salts, hydroxy fatty acid esters, or fatty acids and fatty acid esters with a fatty chain length shorter than 12 carbon atoms. The hydrolysis of esters by Malassezia lipases was detected using High Performance Thin Layer Chromatography (HPTLC). The production of free fatty acids as well as fatty alcohols was observed. The growth promotion or inhibition of bacterial strains was only found in the presence of a few ingredients. Based on these results, formulations containing microbiome inert ingredients were developed.

scholarly journals Sequestration of 9-Hydroxystearic Acid in FAHFA (Fatty Acid Esters of Hydroxy Fatty Acids) as a Protective Mechanism for Colon Carcinoma Cells to Avoid Apoptotic Cell Death

Cancers ◽  
2019 ◽  
Vol 11 (4) ◽  
pp. 524 ◽  
Author(s):  
Juan P. Rodríguez ◽  
Carlos Guijas ◽  
Alma M. Astudillo ◽  
Julio M. Rubio ◽  
María A. Balboa ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Cell Lines ◽  
Hydroxy Fatty Acids ◽  
Fatty Acid Esters ◽  
Protective Mechanism ◽  
Hydroxystearic Acid ◽  
Colorectal Tumors ◽  
Wide Range ◽  
Acid Esters

Hydroxy fatty acids are known to cause cell cycle arrest and apoptosis. The best studied of them, 9-hydroxystearic acid (9-HSA), induces apoptosis in cell lines by acting through mechanisms involving different targets. Using mass spectrometry-based lipidomic approaches, we show in this study that 9-HSA levels in human colorectal tumors are diminished when compared with normal adjacent tissue. Since this decrease could be compatible with an escape mechanism of tumors from 9-HSA-induced apoptosis, we investigated different features of the utilization of this hydroxyfatty acid in colon. We show that in colorectal tumors and related cell lines such as HT-29 and HCT-116, 9-HSA is the only hydroxyfatty acid constituent of branched fatty acid esters of hydroxyfatty acids (FAHFA), a novel family of lipids with anti-inflammatory properties. Importantly, FAHFA levels in tumors are elevated compared with normal tissue and, unlike 9-HSA, they do not induce apoptosis of colorectal cell lines over a wide range of concentrations. Further, the addition of 9-HSA to colon cancer cell lines augments the synthesis of different FAHFA before the cells commit to apoptosis, suggesting that FAHFA formation may function as a buffer system that sequesters the hydroxyacid into an inactive form, thereby restricting apoptosis.

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