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Chemistry of the ENZOGENOL Pine Bark Extract

This section explains the basic chemistry of ENZOGENOL. The following topics are covered:
Composition

Enzogenol is a complex mixture of plant phenolic compounds including many different flavonoids and phenolic acids that occur naturally in the pine bark. Phenolic constituents include proanthocyanidins - these are oligo- or polymers of catechins. The proanthocyanidins (often referred to as OPCs = oligomeric proanthocyanidins) are the most abundent group of phenolics in Enzogenol with more than 80% by weight. Further, a diverse range of other flavonoids and related phenolics present in Enzogenol include the monomeric catechins, quercetin, dihydroquercetin, myricetin, some stilbenes, hydroxylstilbenes, and phenolic acids. More detailed information on proanthocyanidins and other flavonoids is presented below.


Flavonoid structureFlavonoid general structure
Flavonoids are polyphenolic compounds from plants that consist of 15 carbon atoms arranged in a three ring structure (as shown on left). There are several thousand flavonoids and related phenolic compounds that have been identified in plants. Different flavonoids have different chemical properties, but share the ability to function as antioxidants. However, the strength of this antioxidant activity varies widely between the different flavonoid types and depends on the structure of the side residues that are attached to the basic three ring structure.

Proanthocyanidin general structure
proanthocyanidin formulaThe most abundant flavonoids in Enzogenol are proanthocyanidins - dimers, trimers,... up to oligo- and polymers of four slightly different catechins: catechin, epicatechin, gallocatechin, and epigallocatechin. The general structure of proanthocyanidins is shown here on the right.

Below are the chemical structures for the monomeric catechins that are the building blocks of the proanthocyanidins.

catechin epicatechin
catechin epicatechin





gallocatechinepigallocatechin
gallocatechin epigallocatechinMonomeric catechins but in particular the oligo- and polymeric proanthocyanidins have a very high antioxidant activity that contributes to the many health beneficial effects of Enzogenol.



Antioxidant Activity

Enzogenol has been shown to be a very powerful antioxidant in various antioxidant activity tests. A study by Wood et al. (Food Chemistry 77, 2002, p155) has compared the antioxidant activity of Enzogenol with that of other natural extracts, vitamin C and catechin. The results shown in the graph below demonstrate that Enzogenol was the most powerful antioxidant tested in this study and that Enzogenol is dramatically more powerful than for example vitamin C.

Enzogenol as an AntioxidantPresent data is graphed from Table 1. of Wood et al. The antioxidant activity was analysed as the ability to scavenge superoxide radicals in a hypoxanthin oxidase system using the NBT assay. Numbers from the table have been transformed for better graphical representation to shown the % protection at 0.5 ug/ml antioxidant concentration averaging the activity of the three tests done at different pH values.


Chemical Analysis Methods

The composition of Enzogenol has been investigated in several study projects to which a number of independent research institutes from New Zealand and overseas have contributed. Important initial research was carried out at the Department for Chemical and Process Engineering of Canterbury University, New Zealand. Present ongoing research on chemical elucidation is carried out by the Institute for Environmental Science and Research (ESR), Wellington, New Zealand.

Methods used in the analyses of Enzogenol's molecular composition were ultrafiltration, gel permeation chromatography (GPC), thin layer chromatography (TLC), and high performance liquid chromatography (HPLC). Some of the compound structures within Enzogenol were further investigated using nuclear magnetic resonance spectroscopy (NMR).

The method most extensively used is a Reverse Phase HPLC using a C18 matrix that was adopted from Peng ZK et al. (Journal of Agricultural and Food Chemistry 2001, vol. 49, p26-31) for the qualitative and quantitative analysis of Enzogenol. This method is useful in the analysis of phenolic composition, quantification of phenolic components of Enzogenol such as catechin, and proanthocyanidins, stability studies and product identification of Enzogenol. The below chromatogram shows an example of a C18 Reverse Phase HPLC of Enzogenol with detection at 280nm.

Enzogenol HPLC


































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