4263-87-0

Usage

Definition

ChEBI: A guaiacyl lignin obtained by cyclodimerisation of coniferol.

InChI:InChI=1/C20H22O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-6,8-10,15,19,21-23H,7,11H2,1-2H3/b4-3+

Upstream product

• 458-35-5 coniferol 
• 458-35-5 coniferal alcohol 
• 74257-25-3 ethyl caffeate 
• 33050-60-1 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one 
• 2309-07-1 Methyl ferulate 
• 118799-80-7 (E)-methyl 3-<(2RS,3SR)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methoxycarbonyl-1-benzofuran-5-yl>-1-propenoate 

Downstream Products

• 14049-57-1 2α,3β-7-O-methylcedrusin 
• 5234-70-8 tetrahydrodehydrodiconiferyl alcohol 
• 118916-57-7 (E)-3-[2-(4-Hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-2,3-dihydrobenzo[b]furan-5-yl]-2-propenal 
• 168751-78-8 dihydrodehydrodiconiferyl alcohol triacetate 

Relevant academic research and scientific papers

(±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis

Leishmaniasis, a neglected tropical disease caused by parasites of the genus Leishmania, causes a serious burden of disease around the world, represents a threat to the life of millions of people, and therefore is a major public health problem. More effective and non-toxic new treatments are required, especially for visceral leishmaniasis, the most severe form of the disease. On the backdrop that dihydrobenzofurans have previously shown antileishmanial activity, we present here the synthesis of a set of seventy trans-2-phenyl-2,3-dihydrobenzofurans and evaluation of their in vitro activity against Leishmania donovani as well as a discussion of structure-activity relationships. Compounds 8m-o and 8r displayed the highest potency (IC50 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico ADME-like properties and ligand efficiency metrics by a simple scoring function estimating druglikeness highlighted compounds 16c, 18 and 23 as promising candidates for further development. Overall, the potential of trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents was confirmed.

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.

Low molecular weight lignin suppresses activation of NF-κB and HIV-1 promoter

Human immunodeficiency virus type 1 (HIV-1) is a cytopathic retrovirus and the primary etiological agent of acquired immunodeficiency syndrome (AIDS) and related disorders. In cells chronically infected with HIV-1, nuclear factor-κB (NF-κB) activation by external stimuli such as tumor necrosis factor α (TNFα) augments replication of HIV-1. NF-κB involves in many diseases such as inflammation, cancer, and Crohn's disease. In this paper, we exhibit that (i) HIV-1gene expression was inhibited by lignin, (ii) fraction of small molecular mass in HBS lignin (less than 0.5 kDa) had stronger inhibitory effects than large molecular mass (more than 1.3 kDa), (iii) lignin also inhibited activation of NF-κB induced by TNFα, (iv) among six lignin dimer-like compounds, compound 6 containing β-5 bond has more potent inhibitory activity than compounds 1, 2, 3, 4 and 5, which contain β-1, β-O-4, 5-5, or β-β structural units. These results suggested that small molecules of lignin inhibit HIV-1 replication through suppression of HIV-1 transcription from LTR including activation via NF-κB. Low molecular lignin may be a beneficial material or drug leads as a new class for AIDS and NF-κB-related diseases.

Synthesis and structural elucidation of xanthonolignoids: Trans-(±)- kielcorin B and trans-(±)-isokielcorin B

This paper reports the synthesis and characterization of two isomeric xanthonolignoids - trans-(±)-kielcorin B and trans-(±)isokielcorin B. The synthetic approach is based on the oxidative coupling of 2,3-dihydroxy-4- methoxyxanthone with coniferyl alcohol in the presence of silver carbonate. The structural elucidation of these compounds was achieved by extensive NMR studies: 1H and 13C NMR spectra, homonuclear correlation spectroscopy (COSY, COSYLR), heteronuclear correlation spectroscopy (HETCOR), nuclear Overhauser effect (NOE) and one-dimensional selective INEPT. The NMR spectroscopic techniques used in this study led to an unambiguous characterisation of trans-(±)-kielcorin B and trans-(±)-isokielcorin B, which includes the assignment of all proton and carbon resonances and the establishment of the substituents orientation and protons configurational relationship on their 1,4-dioxane ring.

LIGNANS IN CELL CULTURES OF PICEA GLEHNII

A suspension culture derived from the seedling leaves of Picea glehnii accumulated two lignans, pinoresinol and trans-dihydrodehydrodiconiferyl alcohol.The enantiomeric compositions of pinoresinol and dihydrodehydrodiconifery

Regio- and Diastereo-selective Synthesis of Dimeric Lignans Using Oxidative Coupling

The oxidative dimerization of monolignols such as (E)-isoeugenol (1), (E)-methyl ferulate (2) and (E)-coniferyl alcohol (3) has been performed using two catalytic systems: horseradish peroxidase (HRP)-H2O2 and tetraphenylporphyrinatomanganese(III) acetate

Regioselective Synthesis of 2- and 3-Aryl-1,4-benzodioxanes

3-Aryl- and 2-aryl-1,4-benzodioxane derivatives of type 4d and 5d are excellent starting compounds for the synthesis of natural flavano- and neolignans.The syntheses of 4d and 5d were achieved with high regioselectivity by oxidative coupling of caffeic ac

The Relative Configuration of Grossamide and Hordatines

The phenyl group at C-7 of grossamide (1) was determined by PMR spectra to be situated in a trans relationship to the carbonyl group at C-8.It was elucidated that the hordatines (3a, 4a) also have a trans configuration.