Potential anti-cancer agents found in red wine

PHILIP BALL

Acutissimin A may form in red wine as it ages in oak barrels. © alamy.com

In a further boost to its image as a healthy elixir, red wine has been identified as a potential source of new anti-cancer agents.

A group of French chemists has found that red wine contains a chemical compound called acutissimin A. The molecule has previously shown promise as an anti-cancer drug.

"It would be quite inappropriate to infer that red wine possesses anti-tumour properties," warn Stéphane Quideau, of the European Institute of Chemistry and Biology in Pessac, and his colleagues. But, they point out, it could be worth mining red wine for compounds related to acutissimin A.

Acutissimin A was discovered 16 years ago in the bark of the sawtooth oak. It blocks the action of an important enzyme, and in so doing might prevent the growth of cancerous cells. In preliminary tests, it has proved 250 times more potent than the clinical anti-cancer drug VP-16.

Class act

Acutissimin A belongs to a broad class of chemicals called the polyphenols, which are present in fruits, vegetables and drinks made from them. Polyphenols in red wine, green tea and chocolate are known to be antioxidants, which might reduce the risk of heart disease and atherosclerosis. Polyphenols also react with components of saliva to produce the astringency that gives red wine its distinctive taste.

More precisely, acutissimin A sits in a subclass of polyphenols called the ellagitannins; other members of this set are the active constituents of plant extracts used in traditional medicines. "The potential of ellagitannin-based drugs has so far remained untapped," says Quideau's group.

The researchers think that acutissimin A and closely related compounds form in red wine as it ages in oak barrels. In the lab the team made acutissimin A by reacting a substance called vescalagin, extracted from oak wood, with a flavanoid from grapes called catechin¹.

The precise mixture of these compounds in red wine changes as it ages. This not only affects its taste, but also alters the potential pharmacopeia that it harbours.

1. Quideau, S. et al. DNA topoisomerase inhibitor acutissimin A and other flavano-ellagitannins in red wine. Angewandte Chemie International Edition, 42, 6012 - 6014, doi:10.1002/anie.200352089 (2003). |Article|