Lignin Monomers: Oxidation and Degradation

Abstract

The lignin polymer is synthesized via oxidative coupling of three basic monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. These three monomers each possess a phenol group that stabilizes the radical intermediate generated during the oxidation reaction. Although some literature exists showing the ESR spectra of these short-lived radical intermediates, we have revisited these intermediates using a combination of experimental techniques [HPLC and immobilized enzyme-ESR technique (IE-ESR)] and computational approaches [B3YLP/ESR-II and WINSIM]. Two radicals dimerize together to create lignan, which is biologically active and currently being tested for pharmacological properties. HPLC was used to study the oxidation of coniferyl alcohol, the monomeric lignan, and validate the formation of dimers. The mechanisms of this dimer formation were also studied to better understand the oxidative coupling of the lignin monomers.

Introduction

COMING SOON

Lignan

Lignan is formed from the oxidative coupling of two lignin monomers. The dimers are often linked between the beta-carbons on the side chain of each monomer. Many of the dimers stated often in literature possess this linking structure. These dimers have biological activity, whereas the larger structure of lignin does not. This allows them to have potential healths benefits associated with them. Some of these benefits are anti-mubial, anti-inflammatory, and antioxidant. The relationship between allergies and lignan has also been studied. It might be related to having an anti-histamine effect on allergy symptoms.

Research is currently being done to study the relationship between cancer and lignan. Breast cancer has been studied the most, but other cancers such as prostate and ovarian are being researched. Currently there are no conclusions regarding those cancers, as the research is in beginning stages. Many studies are centered around whether consumption of flax seeds correlates to a reduction in the risk of breast cancer, as well as the mortality. The reason flax seeds are being researched is because they have the highest concentration of lignans. With breast cancer, it was found flax seed consumption did decrease the risk of breast cancer, as well as the mortality of breast cancer, in post-menopausal women. This is believed to be because the lignan acts as a competitive inhibitor to estrogen. Some lignans, such as matairesinol and lariciresinol, have structures similar to estrogen. This allows them to bind to the estrogen receptor on the cancer cell, therefore blocking estrogen from binding. This prevents further growth of the cancer.