Beer compounds could hold the key to better pharmacueticals
By Leon Gettler
January 31, 2013
A beer a day might not keep the doctor away but hops, one of the basic ingredients in beer brewing, could be good for you.
In a development that could lead to better drug treatments for diabetes and cancer, University of Washington research associate professor of chemistry, Werner Kaminsky, has determined the exact structure of humulones and their derivatives – the acids in hops that give beer its distinctive bitter taste.
There is already evidence to suggest that the bitter acids in beer (in small doses) can have a positive effect on certain cancers and diabetes, as well as inflammation and possibly even weight loss. It's hoped that by better understanding the chemical structure of these substances, new and more effective pharmaceuticals can be created.
Coauthors Jan Urban, Clinton Dahlberg and Brian Carroll from Seattle-based pharmaceutical company KinDex Therapeutics, which funded the research, recovered humulones from the brewing process. They then purified and converted them into salt crystals and sent them to Kaminsky who used a process called X-ray crystallography, a technique created a century ago, to figure out the exact configuration.
When beer is brewed, the humulone molecules have a unique structure. They are rearranged into a ring of five carbon atoms, not the six found in glucose. The process creates two side groups that can be configured in four ways – above, below or on opposite sides of the ring.
Kaminsky found that the structure of the molecule determines how effective it is in pharmaceuticals. This “handedness” results when a molecule can be arranged in two different ways with the same atoms. A certain “handedness” will see the molecules fitting together like a nut and bolt.
The findings overturned previous research which hadn’t identified handedness and which had assumed uniformity between the molecules.
Kaminsky found enormous variation. Some of the compounds could affect specific illnesses while some, with a slight difference in the arrangement of carbon atoms, were ineffective.
If the molecules don't fit together in the right way, it would be like the left hand going into right handed glove and the result, he says, can be disastrous for pharmaceuticals.
Kaminsky cites thalidomide as one example. The drug was designed originally to treat morning sickness in pregnant women in the late 1950s and early 1960s. Scientists at the time didn’t know the handedness of the molecule. As a result, one orientation caused birth defects while the other orientation did what the pill was created to do.
“We were able to get the correct handedness to the molecule so now basically the tool box is sorted and everybody knows what tool to use to fit to what kind of nut," Kaminsky says.
“Now that we have absolutely correctly assigned the handedness, people can study which of these molecules attach to a protein or taste receptor you have in your body. When that is known, you can then try to attach to it other features making standard molecules that have specific effects, from knowing how it works to developing a drug.
“The next step will be to explore the other humulones that have not yet been studied in detail for their health benefits and in particular, to study the difference between the left and right handed molecules. The left and right handed molecules may very well have very different side effects or actions. That’s important to limit the amount of problems later on."
The next stage of the research is to find out which form of the humulones could create new compounds that could be used in medicine.
But don't reach for that cold brew just yet. Kaminsky points out that beer itself has no health benefits. “The concentration in beer is very small, it’s not big enough to have a direct effect,’’ he says. “But you can isolate the humulones from beer, enrich them, put them into higher concentrations into a supplement. Then it is possible to achieve health benefits.
The findings are reported in the journal Angewandte Chemie International Edition.
Source: University of Washington