An investigation of the lignins of healthy and wilt-affected cotton plants of variety Tashkent-1 according to the vegetation periods

Summary 1. The dioxane lignins of healthy and wilt-affected cotton plants of variety Tashkent-1 have been isolated and have been studied comparatively in relation to the vegetation period. On the basis of elementary and functional analysis, semiempirical formulas of the dioxane lignins isolated (DLCT-I to -VII) have been determined and it has been established that the dioxane lignins isolated from the wilt-affected plants contain more OCH₃ groups per phenyl-propane structural unit than the lignins of healthy plants.2. The molecular-weight distributions of the dioxane lignins have been studied and it has been shown that all the dioxane lignins isolated are polydisperse, those of the affected plants to a greater degree.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 260–264, March–April, 1978.     

A study of the structure of lignins of healthy and wilt-affected cotton plants of the variety Tashkent-1

Continuing a study of the dioxiane lignins of healthy and wilt-affected cotton plants of variety Tashkent-1 (DLCT) according to vegetation period, we have performed nitrobenzene oxidation and cleavage with sodium in liquid ammonia of the natural and isolated dioxane lignins. It has been established that in the wilt-affected samples of cotton-plant stems the amount of guaiacyl and syringyl structural units increases.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 392–396, May–June, 1979.     

Study of the lignin of cotton plants of the variety AN Bayaut-2. I

The dioxane lignin has been isolated from ripe stems of a cotton plant of the variety AN Bayaut-2. Its developed empirical formula has been derived, its UV, IR, and PMR spectra have been recorded, and its molecular weight has been determined. It has been shown that the dioxane lignins of the stems of cotton plants of different varieties differ in chemical structure.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 101–104, January–February, 1986.     

Change in the structural elements of cotton-plant lignins in the various vegetation periods

Summary 1. The dioxane lignins of the cottonplant of various vegetation periods have been studied, and it has been shown that the lignin changes in the course of the development of the plant: the amount of methoxy groups increases and the amount of phenolic hydroxy groups decreases.2. Gel chromatography of the lignins has shown that they are all polydisperse with a predominance of the high-molecular-weight fraction.3. The 3,4-diethoxybenzaldehyde detected in the products of the alkaline nitrobenzene oxidation of dioxane lignin of the early vegetation period after its ethylation with diethyl sulfate is a direct proof of the presence of catechol structural units in cotton-plant lignin.4. A quantitative determination of the catechol structures in the lignins of the cottonplant has shown that their amount decreases as the plant develops.5. By decomposing the lignins with sodium and liquid ammonia, the presence in them of guaiacyl, syringyl, and p-coumaryl structural units has been confirmed and it has been shown that the lignin becomes less condensed as the plant grows, which is apparently connected with an increase in the degree of its methoxylation.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 100–107, January–February, 1977.     

Quantitative1H and13C NMR spectroscopies of cottonplant dioxane lignin

A comparative analysis has been made of the dioxane lignins of the stems, seedling shoots, and seed coats of the cotton plant. The ratio of p-hydroxyaromatic, guaiacyl, and syringyl units in the macromolecules of the lignins has been determined, and so have the amounts of functional groups and bonds. It has been established that the main difference between the dioxane lignins from seedling shoots and seed coats of the cotton plant, on the one hand, and the lignin from the woody stems, on the other hand is a lower content of syringyl and guaiacyl units in the former.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 798–808, November–December, 1994.     

A study of the structure of the dioxiane lignins of the cotton plant of variety 108-F by proton magnetic resonance

Analysis of the PMR spectra of acetylated dioxane lignins of the cotton plant collected in various vegetation periods have shown that the DLAs have different degrees of substitution of the C₃ side chain and different degrees of condensation through the aromatic nuclei. With an increase in the time of extraction of the dioxane lignins from the plant, condensation of the lignins isolated takes place. It has been shown that in the DLAs studied the amounts of -alcoholic hydroxyls are different.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 388–392, May–June, 1979.     

PMR spectra of the lignins ofCystoseira barbata at different ages

The PMR spectra of the dioxane lignins from the brown algaCystoseira have been studied. It has been established that the lignins isolated from specimens ofCystoseira of different ages have different degrees of substitution of the C₃ side chain and differ in their degree of condensation. The most highly condensed is the dioxane lignin of young specimens ofCystoseira (age up to one year) and the least condensed the Björkman lignin ofCystoseira aged more than three years. All the PMR spectra of preparations of the lignin of the alga under investigation contain the signals of protons present in coumaran structures, their amount being the greatest in the lignins of the youngest samples and decreasing with increasing age of the alga.Odessa Institute of Structural Engineering. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 91–94, January–February, 1983.     

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.     

Cotton plant lignins

This paper generalizes the results of studies on lignins isolated from the stems, bolls, and seed hulls of cotton plants of a number of varieties as functions of the vegetation periods of the plants. The UV, IR and¹H and¹³C NMR spectra of the lignins have been studied. The dioxane lignin (DLA) and the natural lignins have been subjected to nitrobenzene oxidation and to cleavage with sodium in liquid nitrogen. A structure of the lignin macromolecules consisting of 18 phenylpropane structural units has been done up. Information is given on the use of lignins in agriculture, the food industry, and the paint and varnish industry. The anticorrosion and sorption properties of hydrolysis and modified hydrolysis lignins have been studied.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 40 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 465–496, July–August, 1997.     

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.     

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.Institute of the Chemistry of Plant Substances of the Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 738–742, September–October, 1987.     

PMR spectra of the dioxane lignins of some plants of the family Malvaceae

Analysis of PMR spectra of the dioxane lignins of three species ofAthea, of kenaf, and of the cotton plant has shown that the number of free aromatic protons does not correlate with the number of OCH₃ groups, which indicates different degrees of condensation of the dioxane lignins studied. In all the preparations a very small amount of coumarane structures were found. The aliphatic OH groups have been distinguished as primary (-OH) and secondary (-OH) and their quantitative estimation has been carried out from the PMR spectra.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 560–563, July–August, 1980.     

Aminomethylation of dioxane lignins of healthy and wilt-diseased cotton plants of the variety Tashkent-1

The products of the aminomethylation of dioxane lignins of healthy and wilt-diseased plants of variety Tashkent-1 according to the vegetation periods (ADLKhT-1-VII) have been studied. It has been established that the dioxane lignins of the wilt-diseased cotton-plant stems are less condensed. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 704–706, September–October, 1980.     

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.     

The lignin of the sea island cotton plant of variety S-6030 affected by fusarial wilt. I

A comparative study of the dioxane lignins isolated from healthy and wilt-affected cotton plant stems has shown thatFusarium fungi demethylate lignin and make it more oxidized than the lignin from healthy stems.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 825–827, November–December, 1985.     

Hydrogenolysis of rice husk lignins

The hydrogenolysis of the protolignin, the hydrolysis lignin, and the dioxane lignin of rice husks in the presence of demethylated lignin as catalyst has been studied. The breakdown of the lignins into low-molecular-mass compounds took place with yields comparable with those obtained by hydrogenolysis using other catalysts.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 611–613, July–August, 1995. Original article submitted November 21, 1994.     

An investigation of the fractional composition of dioxane lignin of the cotton plant by the PMR method

Analysis of the PMR spectra of six fractions of the dioxane lignins of the cotton plant differing considerably in molecular weight has confirmed their chemical nonidentity. It has been established that the low-molecular-weight fractions are less condensed than the high-molecular-weight fractions. It has been found that aliphatic OH groups are approximately evenly distributed between the - and -C atoms of the lignin side chain.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 116–120, January–February, 1980.     

Lignin of the fine-fibered cotton plant of variety S-6030 affected by fusarial wilt. II

A comparative study of the products of cleavage by sodium in liquid ammonia of the dioxane lignins (DLAs) from healthy and fusarial-wilt-affected stems of the fine-fibered cotton plant of variety S-6030 and a study of the PMR spectra of both lignins has shown that the DLA from the healthy stems is more highly condensed than the DLA of the stems affected by wilt. The main structures of DNA wilt are of the guaiacyl type. In the DLA from the affected stems, the amount of p-coumaryl structures had increased, which confirms the demethylating action of fusarial wilt on cotton-plant lignin.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 364–366, May–June, 1986.     

A comparative study of the dioxane lignins ofAlthea

Summary 1. The dioxane lignins have been extracted from three species ofAlthea for the first time. On the basis of elementary and functional analyses, the semiempirical formulas of the phenylpropane structural units have been calculated.2. The molecular weight distributions have shown that the DLAs of these species ofAlthea are polydisperse, and in the case of the DLAs of the wild-growing species —A. rhyticarpa andA. nudiflora — the high-molecular weight fraction is predominant, while for the DLA ofA. rosea the low-molecular-weight fraction is predominant.3. In a study of the products of nitrobenzene oxidation it has been established that the DLA of all three species ofAlthea includes p-coumaryl, guaiacyl, and syringyl structural units.4. In the products of decomposition with metallic sodium in liquid ammonia 18 phenols have been identified the structures of which show the presence in the initial lignins of guaiacyl- and syringylpropane units with free OH groups in the side chains in the - and -positions to the aromatic nucleus.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 93–100, January–February, 1977.     

A study of the dioxane lignin of the stems of the cotton plant of variety S-4880

The dioxane lignin (DLA) has been isolated from the ripe stems of a cotton plant of the variety S-4880 B by a modification of Pepper's method. The yield was 16.9% on the Komarov lignin. The semiempirical formula of a phenylpropane structural unit has been calculated on the basis of elementary and functional analyses. It has been established that the amount of the main functional groups in the DLA and in the lignins isolated from the varieties of 108-F and Tashkent-2 basically coincide, but the DLA investigated was appreciably more highly methoxylated. The IR, UV, and PMR spectra of the DLA have been taken. The molecular-weight distribution of the DLA has been investigated and it has been shown that is is poly-disperse and has a weight-average molecular weight of 7400. Nitrobenzene oxidation and cleavage with sodium and liquid ammonia of the isolated DLA has shown that guaiacyl structural units predominate in it.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 430–434, May–June, 1987.