124151-33-3

Usage

Uses

Used in Pharmaceutical Industry:
Coniferin is used as a pharmaceutical intermediate for its potential therapeutic applications. It is involved in the biosynthesis of lignin, a complex organic polymer that provides structural support to plant cell walls. The study of coniferin and its role in lignification can lead to the development of novel drugs targeting plant-related diseases and conditions.
Used in Biochemical Research:
Coniferin is used as a research tool in the field of biochemistry, particularly in studying the lignification process and the role of Coniferin β-D-Glucosidase. Understanding the function and interactions of coniferin can contribute to the advancement of knowledge in plant biochemistry and the development of new strategies for improving plant growth and resistance to diseases.
Used in Plant Biotechnology:
Coniferin is used as a key compound in plant biotechnology, where it can be manipulated to enhance the lignification process in coniferous trees. This can lead to the development of plants with improved structural support, which can be beneficial for various applications such as forestry and agriculture.
Used in Wood and Paper Industry:
Coniferin, due to its role in lignification, can be used to improve the quality and properties of wood and paper products. By understanding and manipulating the lignification process, it is possible to develop wood with enhanced mechanical properties and paper with improved strength and durability.

Upstream product

• 62604-84-6 [4-(3-hydroxy-trans-propenyl)-2-methoxy-phenyl]-(tetra-O-acetyl-β-D-glucopyranoside) 
• 67-56-1 methanol 
• 131723-87-0 4-(3-acetoxy-1-propenyl)-2-methoxyphenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 458-35-5 coniferal alcohol 
• 952585-00-1 uridine-5'-diphosphoglucose 
• 51482-43-0 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)vanillin 
• 133-89-1 UDP-glucose 
• 458-35-5 coniferol 
• 23598-08-5 methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 62604-85-7 3-methoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde 
• 121-33-5 vanillin 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 132748-08-4 coniferyl aldehyde 4-O-β-D-glucopyranoside 
• 50-99-7 D-glucose 
• 458-35-5 coniferal alcohol 

Relevant academic research and scientific papers

Anti-inflammatory terpenes from Schefflera rubriflora C. J. Tseng & G. Hoo with their TNF-α and IL-6 inhibitory activities

The 95% ethanol extract and its EtOAc and n-BuOH fractions obtained from the leaves and twigs of Schefflera rubriflora C. J. Tseng & G. Hoo showed significant inhibitory activities (33.6%, 35.7% and 40.6%, respectively) against croton oil-induced ear inflammation in mice. Bioactivity-guided isolation and separation gave eight previously undescribed terpenes or terpene glycosides. Structural elucidation was based on UV, IR, and NMR spectroscopy, MS, experimental and calculated ECD data, and Mosher's method. To identify anti-inflammatory components from the extract, all the compounds were evaluated for tumor necrosis factor-α (TNF-α) and interleukine-6 (IL-6) inhibitory activities. Four undescribed compounds inhibited mRNA expression of TNF-α and IL-6 with IC50 values of 15.3–52.4 μM.

Oxidation of monolignols by members of the berberine bridge enzyme family suggests a role in plant cell wall metabolism

Plant genomes contain a large number of genes encoding for berberine bridge enzyme (BBE)-like enzymes. Despite the wide-spread occurrence and abundance of this protein family in the plant kingdom, the biochemical function remains largely unexplored. In this study, we have expressed two members of the BBE-like enzyme family from Arabidopsis thaliana in the host organism Komagataella pastoris. The two proteins, termed AtBBE-like 13 and AtBBE-like 15, were purified, and their catalytic properties were determined. In addition, AtBBE-like 15 was crystallized and structurally characterized by x-ray crystallography. Here, we show that the enzymes catalyze the oxidation of aromatic allylic alcohols, such as coumaryl, sinapyl, and coniferyl alcohol, to the corresponding aldehydes and that AtBBE-like 15 adopts the same fold as vanillyl alcohol oxidase as reported previously for berberine bridge enzyme and other FAD-dependent oxidoreductases. Further analysis of the substrate range identified coniferin, the glycosylated storage form of coniferyl alcohol, as a substrate of the enzymes, whereas other glycosylated monolignols were rather poor substrates. A detailed analysis of the motifs present in the active sites of the BBE-like enzymes in A. thaliana suggested that 14 out of 28 members of the family might catalyze similar reactions. Based on these findings, we propose a novel role of BBE-like enzymes in monolignol metabolism that was previously not recognized for this enzyme family.

Coniferyl alcohol metabolism in conifers - I. Glucosidic turnover of cinnamyl aldehydes by UDPG: Coniferyl alcohol glucosyltransferase from pine cambium

UDPG: coniferyl alcohol glucosyltransferase (CAGT; EC 2.4.1.111) isolated from cambial tissues of Pinus strobus was able to convert cinnamyl aldehydes as well as dihydroconiferyl alcohol into their corresponding 4-O-β-D-glucosides in vitro, Cinnamyl aldeh

Coniferin and derivatives: A fast and easy synthesis via the aldehyde series using phase-transfer catalysis

Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig- type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.

SYNTHESIS AND AGROBACTERIUM vir-INDUCING ACTIVITIES OF CONIFERYL ALCOHOL &β-GLYCOSIDES

Coniferyl alcohol β-glycosides were synthesized by coupling coniferyl alcohol sodium salt in aqueous acetone with peracetylated glycosyl halides of D-glucopyranose, D-galactopyranose and L-fucopyranose.After O-deacetylation by sodium methoxide, the glycosides were tested for their potential vir gene-inducing activities in Agrobacterium tumefaciens A348/psM358 and A348/psM243cd harbouring, respectively, vir E::lacZ and virB::lacZ fusion plasmids.In the large range of concentrations tested, these synthetic derivatives had vir-inducing activity on strain A348/psM358: D-Gal > D-Glc.The dose-response curves of these glycosylated compounds were completely different from those of free coniferyl alcohol; the β-galactopyranoside at 500 μM exhibited interestingly a greater activity than the free aglycone after 12 hr incubation period.The coniferyl alcohol β-glucopyranoside was a better inducer than the related β-galactopyranoside on strain A348/psM243cd.The β-L-fucopyranoside was inactive with both A. tumefaciens strains.The activities of these glycosylated inducers were correlated with the presence of intracellular glycosylhydrolases from the various A. tumefaciens strains studied.It is noteworthy that the vir-gene induction activity of the coniferyl alcohol β-galactopyranoside on strain A348/psM358 was due to a high basal level of expression of the virE::lacZ fusion gene.

Studies on the constituents of the bark of Kalopanax pictus Nakai

Five new compounds, kalopanaxsaponin G (2) and kalopanaxins A (6), B (8), C (11) and D (13), were isolated from the bark of Kalopanax pictus together with nine known compounds, kalopanaxsaponins A (1) and B (5), pericarpsaponin P(J3) (3), hederasaponin B (4), syringin (7), protocatechuic acid (9), coniferin (10), liriodendrin (=dl-syringaresinol di-O-glucopyranoside) (12), glucosyringic acid (14) and chlorogenic acid (15). The structures of the new compounds were characterized as hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D- glucopyranoside (2), ferulylaldehyde (=coniferylaldehyde) 4-O-β-D-glucopyranoside (6), coniferin 6'-O-(4-O-α-L-rhamnopyranosyl)-syringate (8), 2-methoxyhydroquinone 4-O-[6-O[(4-O-α-L-rhamnopyranosyl)-syringyl]-β-D-glucopyranoside (11) and coniferyl alcohol 4-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (=coniferin 2'-O-β-D-apiofuranoside) (13).