Determination and separation of diarylheptanoids from alder growing in Latvia
The composition of diarylhepatnoids fraction isolated from bark of two alder species (grey alder and black alder) was studied. The efficiency of three extraction methods used for isolation of diarylhepatnoids from alder bark was compared. Two diarylhepatnoids: 1,7-bis-(3,4-dihydroxyphenyl)-heptan- 3-one-5-O-β-D-xylopyronoside (oregonin) and 1,7-bis-(3,4-dihydroxyphenyl)-3-hydroxyheptane-5-O-β-D- xylopyranoside were isolated from the bark of grey alder. The phenolic components of the extracts were analyzed by high-performance liquid chromatography (HPLC). Quantitative determination of oregonin was performed using an internal standard method. The results obtained show that alder barks are ric…
Elucidation of antioxidant properties of wood bark derived saturated diarylheptanoids: a comprehensive (DFT-supported) understanding.
A series of diarylheptanoids, namely 1,7-bis-(3,4-dihydroxyphenyl)-heptan-3-one-5-O-D-xylopyranoside (oregonin), 1,7-bis-(3,4-dihydroxyphenyl)-3-hydroxyheptane-5-O-β-D-xylopyranoside and 1,7-bis-(4-hydroxyphenyl)-heptane-3-one-5-O-β-D-glucopyranoside (platyphylloside), were isolated from the bark of alder family trees, a species widely spread over in Europe. As antioxidants, these natural polyphenols have a promising potential in various fields of application, but their redox reactivity is insufficiently characterized. In this work, their antioxidant activity is described using assays based on DPPH and ABTS(+) radical scavenging, oxygen anion radicals (O2(-)) quenching. The standardized ORA…
Design of siliceous lignins – Novel organic/inorganic hybrid sorbent materials
Novel nanoporous lignin(lignocellulose)/SiO2 hybrid materials were designed using the sol–gel process. X-ray photoelectronic spectroscopy, Fourier transform infrared spectroscopy and 29Si and 13C nuclear magnetic resonance spectroscopy were applied to characterize the hybrids’ surface and bulk structure. Nitrogen and water vapor sorption were used for assessment of porous structure parameters and hydrophobization of matrices, respectively. The efficiency of the hybrid materials obtained was proved by adsorption tests with potential inorganic (Cu2+) and organic (2,4-dichlorophenoxyacetic acid) pollutants.
Characterization of softwood and hardwood lignoboost kraft lignins with emphasis on their antioxidant activity
Fractionation of softwood and hardwood LignoBoost kraft lignins, using sequential extraction with organic solvents of increasing hydrogen-bonding ability (dichloromethane, n-propanol, and methanol), was carried out. Using SEC, analytical pyrolysis, FTIR and UV/VIS spectroscopy, and chemical analytical methods, four fractions were obtained and characterized in terms of their yield, composition, functionality, lignin structural features, and antioxidant properties. In tests with free radicals (ABTS●+, DPPH●, O2●-) and the ORAC (oxygen radical absorbance capacity) assay, the high radical scavenging capacity of the lignin’s soluble fractions was demonstrated. The antioxidant activity of the fra…
Elaboration and characterization of organic/inorganic hybrid nanoporous material incorporating Keggin-type Mo-Si polyanions
A novel nanoporous (pore size of 11 nm in average, BET surface area of 30 m2/g, pore volume of 300 mm3/g) hybrid inorganic-organic material was synthesized using the solid-phase interaction at room temperature of plant-originated phenylpropanoid polymer lignin and a Keggin-type heteropolyanion [SiMo12O40]4-. The partly reduction of Mo(VI) to Mo(V) and complexes formation between lignin and polyanion have been established by EPR, FT-IR and Raman spectroscopy. The XRD pattern and FT-IR spectrum of the hybrid material and indicates that [SiMo12O40]4- anion maintains the Keggin structure.
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, betu…
Role of paramagnetic polyconjugated clusters in lignin antioxidant activity(in vitro)
Using physico-chemical methods (EPR, SEC, Py-GC/MS and UV/VIS spectroscopy) and wet chemical analysis, the characteristics of 6 hardwood lignins in terms of functionality, molecular weight and composition of lignin substructures were determined and considered together with the results of DPPH•, ABTS•+ and O2•− antioxidant assays with the aim to understand the relationships governing antioxidant properties of lignin. The strong positive linear correlation between lignin antioxidant capacity in the three assays used and the extent of conjugation of paramagnetic polyconjugated clusters in lignin macromolecules was found. The biological activity of the most active alkaline lignins was assessed …
Evaluation of Ligno Boost™ softwood kraft lignin epoxidation as an approach for its application in cured epoxy resins
Abstract In this study, modification of LignoBoost™ softwood kraft lignin with epichlorhydrin in water-organic solvents media was realized. Lignin-based epoxy resins were obtained by two ways: acetone extraction of glycidylated lignin or glycidylation of the acetone soluble lignin fraction. The effect of glycidylation regimes on the yields of acetone soluble fractions, their functional composition and physical-chemical characteristics was investigated using wet chemistry methods, FTIR spectroscopy, size exclusion chromatography (SEC) and differential scanning calorimetry (DSC). The positive effect of the biphasic phase transfer catalytic system – KOH/quaternary ammonium salt – on glycidylat…