Antiangiogenic Activity of Synthetic Dihydrobenzofuran Lignans

Abstract

A series of synthetic dihydrobenzofuran lignans, obtained by biomimetic oxidative dimerization of caffeic or ferulic acid methyl ester followed by derivatization reactions, was tested for its antiangiogenic activity in the CAM (chorioallantoic membrane) assay. The dimerization product of caffeic acid methyl ester (2a) (methyl (E)-3-[2-(3,4-dihydroxyphenyl)-7-hydroxy-3-methoxycarbonyl-2,3-dihydro-1-benzofuran-5-yl]prop-2-enoate) showed a pronounced antiangiogenic activity, especially the 2R,3R-enantiomer.

Novel Derivative of Benzofuran Induces Cell Death Mostly by G2/M Cell Cycle Arrest through p53-dependent Pathway but Partially by Inhibition of NF-κB

“…Some of the derivatives of benzofuran lignan were found to act against tumor proliferation (19,31). We provided evidence that a novel synthetic benzofuran lignan (known as Benfur) induced cell death by G2/M phase arrest in p53 ϩ/ϩ cells at low concentration.…”

Biomimetic Synthesis of Natural and “Unnatural” Lignans by Oxidative Coupling of Caffeic Esters

“…According to IUPAC recommendations, [2] "neolignans" are dimers that originate from coupling other than 8-8Ј coupling, although the term "lignan" is frequently employed in a broader sense (including neolignan), as in the title of this article. Lignans, neolignans and other related compounds are accumulated in vascular plants as a chemical defence system, [3] and this may explain their diverse biological activities, including cytotoxic, [4] antimitotic, antileishmanial, [5] antiangiogenic, [6] cardiovascular [7] and antiviral activity. [8] The biological activities and structural variety of lignans and related compounds make them an attractive target for chemical synthesis or modification.…”

Evaluation of Antiangiogenic Effect of the Leaves of Justicia gendarussa (Burm. f ) (Acanthaceae) by Chrio Allontoic Membrane Method

“…Justicia found to contain lignans, naturally occurring phenolic dimers [6] and triterpenoids [7] Lignans have been used as lead compounds for the development of antirheumatic agents [8] . Among the known angiogenic inhibitors triterpenoids play a prominent role [1] . Its medicinal properties for the treatment of arthritis and the presence of lignans, triterpenoids inspired us to take up this study.…”

“…It plays a critical role in normal physiological process such as wound healing but also in a number of pathological processes for instance diabetic retinopathy, arthritis and the growth of solid tumors [1] . Any imbalance in this process may promote numerous angiogenesis.…”