Cleavage by sodium in liquid ammonia of kenaf lignins and the biological activity of the cleavage products

The natural lignin of kenaf stems and fractions of the dioxane lignin of kenaf stems isolated previously were cleaved by sodium in liquid ammonia in order to study their structure. It was established that the kenaf lignins consist of three types of structural units: p-coumaryl, guaiacyl, and syringyl, with a predominance of the guaiacyl types. An antioxidation activity of the monomeric products of the degradation of the kenaf lignins has been found.     

Reductive cleavage by metallic sodium in liquid ammonia of cotton lignin

Twofold cleavage with sodium in liquid ammonia of the dioxane lignin and fourfold cleavage of the native lignin from cotton stems have shown that the uncleaved parts of lignin have molecular masses 2–4 times lower than the initial lignins and consist of 15–17 phenylpropane structural units.Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 412–416, May–June, 1989.     

Reductive cleavage by sodium in liquid ammonia of the lignin of cotton-plant stems

Summary 1. The reductive degradation by metallic sodium and liquid ammonia of the lignin of green cotton-plant stems has confirmed the presence in them of three types of structural units: syringyl, guaiacyl, and p-hydroxycoumaryl.2. The preliminary sonication of the plant with ultrasound leads to a decrease in the amount of products containing methoxy groups in the aromatic nucleus, particularly syringyl structures.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 643–646, September–October, 1976.     

Dioxane lignins of kenaf bast and tow

Summary 1. Dioxane lignins have been isolated from the outer (bast) and inner (tow) parts of kenaf of the variety Uzbekskii 15–74, and the semiempirical formulas of the phenylpropane structural units of these dioxanes have been calculated on the basis of elementary and functional analyses.2. It has been shown by measurements of molecular-weight distribution that the DLAKK was more polydisperse than the DLALK.3. A study of the products of alkaline nitrobenzene oxidation and of decomposition by metallic sodium in liquid ammonia has shown that the DLAKK and DLALK were constructed of p-coumaryl, guaiacyl, and syringyl structural units, with the latter predominating.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 74–82, January–February, 1979.     

Establishment of an ester bond in kenaf lignins

Summary Four dioxane lignins from kenaf have been subjected to alkaline hydrolysis, and the presence of esterified p-coumaric and p-hydroxybenzoic acids in them has been shown.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 216–218, March–April, 1979.     

A study of the structure of kenaf lignins by alkaline nitrobenzene oxidation

Summary 1. The nitrobenzene oxidation of the natural lignins of kenaf stems and of DLA fractions has been performed. A study of the oxidation products by gas-liquid chromatography has shown that the kenaf lignins are constructed of three types of structural units: p-coumaryl, guaiacyl, and syringyl, with the latter predominating.2. Among the products of the nitrobenzene oxidation of fractions of kenaf dioxane lignin paper chromatography has shown the presence of dihydrodivanillin, which is a representative of structures with a biphenyl bond.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 641–645, September–October, 1978.     

Rupture of sulfides of the thiophene series by sodium in liquid ammonia

Summary By tne action of sodium in liquid ammonia, alkylthienyl sulfides are readily dealkylated with formation of the corresponding mercaptans of the thiophene series.     

Deoxygenation of sugar trifluoromethanesulfonates by sodium metal in liquid ammonia and by photolysis

Several trifluoromethanesulfonyl(TFMS) derivatives of sugars were prepared and treated with sodium in liquid ammonia or subjected to ultraviolet irradiation. Three 3-$\text{O}$-TFMS derivatives gave the corresponding 3-deoxy compounds, but a 2-$\text{O}$-TFMS derivative gave a branched-chain sugar.     

Cleavage of the natural lignin and the dioxane lignin of kenaf by thioacetic acid

The dioxane lignin and the natural lignin of kenaf undergo 37.62% and 94.6% cleavage, respectively. The combined monomeric degradation products have been studied by the GLC method. The presence of substances relating to three types of structural units has been established: p-coumaryl, gualacyl, and syringyl. It has been shown by chromatography on Sephadex LH-20 (with ethanol-water (9:1) as solvent and eluent) that the phenolic products of degradation extracted by ethyl acetate at pH 2 consist of five fractions: oligomers, tetramers, trimers, dimers, and monomers.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 234–235, March–April, 1986.