Syringylpropane

Insecticidal and alpha-glucosidase inhibitory activities of chemical constituents from Viburnum fordiae Hance.[Pubmed:29703100]

Nat Prod Res. 2018 Apr 27:1-6.

The ethanolic extract of the stems of Viburnum fordiae Hance showed insecticidal and alpha-glucosidase inhibitory activities and then was fractionated by bioactivity-guided fractionation to obtain a rare C13-norisoprenoid (1), together with a new phenolic glycoside (2), and seven known compounds, alangionoside C (3), pisumionoside (4), koaburaside (5), 3,5-dimethoxy-benzyl alcohol 4-O-beta-d-glucopyranoside (6), 3,4,5-trimethoxybenzyl-beta-d-glucopyranoside (7), arbutin (8), and salidroside (9). The previously undescribed compounds were elucidated as (3R,9R)-3-hydroxy-7,8-didehydro-beta-ionyl 9-O-alpha-d-arabinopyranosyl-(1-->6)-beta-d-glucopyranoside (1) and 2-(4-O-beta-d-glucopyranosyl)Syringylpropane-1,3-diol (2) by spectroscopic data ((1)H and (13)C NMR, HSQC, HMBC, (1)H-(1)H COSY, HSQC-TOCSY, HRESIMS, IR and ORD) and chemical methods. Compound 1 showed potent insecticidal effect against Mythimna separata with LD50 value of 140 mug g(-1). Compounds 2, 5, 6, 8 and 9 showed varying alpha-glucosidase inhibitory activity with IC50 values ranging from 148.2 to 230.9 muM.

Lignin structural variation in hardwood species.[Pubmed:22533315]

J Agric Food Chem. 2012 May 16;60(19):4923-30.

A comprehensive lignin structure analysis of ten industrially relevant hardwood species is presented. Milled wood lignin (MWL) was isolated from each species using a modified protocol and all milled wood lignin preparations were analyzed through quantitative (13)C NMR spectroscopy, elemental analysis, methoxyl analysis, sugar analysis, and nitrobenzene oxidation. Nitrobenzene oxidation and ozonation were carried out on extractive-free wood, alkali-extracted wood, milled wood lignin, and alkali-extracted lignin. Milled wood lignin isolated by the modified protocol was found to be representative of the total lignin in alkali-extracted wood. Significant variations in lignin structures, such as Syringylpropane/guaiacylpropane ratio (S/G ratio), arylglycerol-beta-aryl ether (beta-O-4), degree of condensation, and elemental and methoxyl contents, were found among the hardwood species studied. These structural variations among species appear to be correlated to a single factor, the syringyl/guaiacyl ratio. A new method to predict the S/G ratio of total lignin in wood was developed, using a calibration line established by the syringaldehyde/vanillin (S/V) ratio (nitrobenzene oxidation) and the S/G ratio ((13)C NMR) of milled wood lignin (MWL).

Chemical composition and structural features of the macromolecular components of plantation Acacia mangium wood.[Pubmed:16190642]

J Agric Food Chem. 2005 Oct 5;53(20):7856-62.

The wood of Acacia mangium, a prominent fast-growing plantation species used in the pulp-and-paper industry and, so far, poorly investigated for its chemical structure, was submitted to a detailed characterization of its main macromolecular components. Lignin (28% wood weight) isolated by mild acidolysis and characterized by permanganate oxidation, 1H and 13C NMR, and GPC, showed a very low content of Syringylpropane-derived units (S:G:H of 48:49:3), a high degree of condensation, a low content of beta-O-4 ( approximately 0.40-0.43 per C6) structures, and a Mw of 2230. Glucuronoxylan (14% wood weight) isolated by alkaline (KOH) or by dimethyl sulfoxide extraction was characterized by methylation analysis, 1H NMR, and GPC. About 10% of the xylopyranose (Xylp) units constituting the linear backbone were substituted at O-2 with 4-O-methylglucuronic acid residues. Almost half of the Xylp units (45%) were O-2 (18%), O-3 (24%) or O-2,3 (3%) acetylated. X-ray diffraction analysis of cellulose (46% wood weight), isolated according to the Kurschner-Hoffer method, showed a degree of crystallinity of 67.6%.

A polyclonal antibody directed against syringylpropane epitopes of native lignins.[Pubmed:15587072]

C R Biol. 2004 Sep-Oct;327(9-10):809-15.

With a view to visualizing the ultrastructural distribution of syringyl lignins in secondary plant cell walls, a polyclonal antibody raised from a synthetic DHP polymer consisting only of syringyl propane units was prepared. To test the reactivity of the antiserum, a mini-dot-blot immunoassay reducing the amounts of substrates and antiserum was developed. A characteristic attribute of the S-antiserum appears to be its specific recognition of sequences of three or more consecutive syringyl units. On ultra-thin sections of model plants of Arabidopsis thaliana, Populus and tobacco, the antiserum allowed us to demonstrate a higher concentration of syringyl epitopes in fibres than in vessels. Variations in the distribution pattern of these epitopes between the three plants examined suggest that the synthesis of syringyl lignins in angiosperms depends on the species.

Lignin monomer composition is determined by the expression of a cytochrome P450-dependent monooxygenase in Arabidopsis.[Pubmed:9618461]

Proc Natl Acad Sci U S A. 1998 Jun 9;95(12):6619-23.

The phenylpropanoid pathway provides precursors for the biosynthesis of soluble secondary metabolites and lignin in plants. Ferulate-5-hydroxylase (F5H) catalyzes an irreversible hydroxylation step in this pathway that diverts ferulic acid away from guaiacyl lignin biosynthesis and toward sinapic acid and syringyl lignin. This fact led us to postulate that F5H was a potential regulatory step in the determination of lignin monomer composition. To test this hypothesis, we have used Arabidopsis to examine the impact of F5H overexpression. Arabidopsis is a useful model system in which to study lignification because in wild-type plants, guaiacyl and syringyl lignins are deposited in a tissue-specific fashion, while the F5H-deficient fah1 mutant accumulates only guaiacyl lignin. Here we show that ectopic overexpression of F5H in Arabidopsis abolishes tissue-specific lignin monomer accumulation. Surprisingly, overexpression of F5H under the control of the lignification-associated cinnamate-4-hydroxylase promoter, but not the commonly employed cauliflower mosaic virus 35S promoter, generates a lignin that is almost entirely comprised of Syringylpropane units. These experiments demonstrate that modification of F5H expression may enable engineering of lignin monomer composition in agronomically important plant species.

Analysis of Lignin-Polysaccharide Complexes Formed during Grass Lignin Degradation by Cultures of Pleurotus Species.[Pubmed:16535332]

Appl Environ Microbiol. 1996 Jun;62(6):1928-34.

A brown material, precipitable with ethanol, was formed during wheat straw and lignin degradation by liquid cultures of different species of Pleurotus. Fourier transform infrared spectroscopy and cross-polarization and magic-angle-spinning (sup13)C nuclear magnetic resonance spectroscopy showed that most of the precipitable material was formed from exopolysaccharide secreted by the fungus but it also contained an aromatic fraction. The results of acid hydrolysis, methylation analysis, and Smith degradation indicated that the major exopolysaccharide produced by these fungi is a (1(symbl)3)-(beta)-glucan branched at C-6 every two or three residues along the main chain. The presence of lignin or straw in the culture medium had little effect on the composition and structure of the extracellular polysaccharide. Cross-polarization and magic-angle-spinning (sup13)C nuclear magnetic resonance spectroscopy provided an estimation of the aromatic content of the lignin-polysaccharide complexes, assigning 20% of the total (sup13)C signal in the material recovered from cultures of Pleurotus eryngii in lignin medium to aromatic carbon. Analytical pyrolysis indicated that the aromatic fractions of the lignin-polysaccharide complexes were derived from lignin, since products characteristic of pyrolytic breakdown of H (p-hydroxyphenylpropane), G (guaiacylpropane), and S (Syringylpropane) lignin units were identified. These complexes cannot be fractionated by treatment with polyvinylpyrrolidone or extraction with lignin solvents, suggesting that the two polymers were chemically linked. Moreover, differences in composition with respect to the original lignin indicated that this macromolecule was modified by the fungi during the process of formation of the lignin-polysaccharide complexes.