Monkeys, Myths, and Molecules: Separating Fact from Fiction in the Science of Everyday Life

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MONKEYS, MYTHS, AND

MOLECULES

SEPARATING FACT FROM FICTION IN THE SCIENCE OF EVERYDAY LIFE

DR. JOE SCHWARCZ

ecw press

INTRODUCTION

Why Monkeys, Myths and Molecules? Yes, there is a link. And it is meaningful. Let me start my rationale with a question one of my students recently asked. What is the most significant discovery in the history of chemistry? I was really stymied because our knowledge of chemistry is based on a long string of incremental advances and it is unrealistic to label any single discovery as the most significant. There have of course been many momentous discoveries.

We can think of the smelting of metals from their ores, the development of ink, the splitting of the atom and the discoveries of the electron, radioactivity, oxygen and plastics. Dalton’s theory that elements are made of atoms capable of combining in various ways to form compounds ranks up there, as does Wöhler’s demonstration that chemicals made by living organisms, urea for example, can be produced from non-living substances. Haber’s synthesis of ammonia led to the mass production of fertilizer that saved countless lives, as did the discovery of penicillin. But fundamental to the practice of chemistry is the understanding of the structure of molecules. So an argument can be made for August Kekulé’s unraveling of the mystery of molecular structure as ranking at, or near the top, of a list of chemical discoveries. And that discovery was supposedly inspired by a dream! A dream that would lead to some monkey business.

August Kekulé’s suggestion that the benzene molecule is composed of carbon atoms joined in a ring was a huge contribution to the development of chemistry. Chemists had long known that benzene consisted of six carbons and six hydrogens, but they had no idea how the atoms were arranged in space. Kekulé’s solution explained benzene’s behavior and provided the basis for planning other reactions that would lead to synthesizing novel dyes, drugs and plastics.

Kekulé was a dreamer, or at least he said he was. In 1890, at a meeting organized in his honor by the German Chemical Society, he recounted how two dreams had led to his being labeled the principal founder of the theory of molecular structure. The first one, in 1858, resulted in the formulation of the basic theory of how atoms can join together to form molecules. Carbon atoms were said to be tetravalent, meaning they had the ability to form four bonds, nitrogen formed three, oxygen two and hydrogen one. Most importantly, carbon atoms could link to each other, allowing for the possible formation of a huge variety of molecules. Kekulé claimed the idea came to him while riding a horse-drawn omnibus in London:

I fell into a reverie, and lo, the atoms were gamboling before my eyes.… I saw how, frequently, smaller atoms united to form a pair; how a larger one embraced the two smaller ones; how still larger ones kept hold of three or even four of the smaller; whilst the whole kept whirling in a giddy dance. I saw how the larger ones formed a chain, dragging the smaller ones after them but only at the ends of the chains.… The cry of the conductor: Clapham Road awakened me from my dreaming; but I spent part of the night in putting on paper at least sketches of these dream forms. This was the origin of the Structural Theory.

Kekulé then went on to describe the more famous incident that supposedly occurred in 1865 in which he realized that the benzene molecule had a ring structure:

I was sitting writing on my textbook but the work did not progress; my thoughts were elsewhere. I turned my chair to the fire and dozed. Again the atoms were gambolling before my eyes.… My mental eye, rendered more acute by the repeated visions of the kind, could now distinguish larger structures, of manifold confirmation; long rows, sometimes more closely fitted together; all twining and twisting in snakelike motion. But look! What was that? One of the snakes had seized hold of its own tail, and the form whirled mockingly before my eyes. As if by a flash of lightning I awoke; and this time also I spent the rest of the night in working out the rest of the hypothesis.

We will never know whether the dream stories are historically accurate or whether they represent a form of poetic license used by Kekulé to inspire scientists to think outside the proverbial box. Certainly Kekulé was not the first to whom the idea of a snake biting its tail occurred. The ouroboros, Greek for tail devourer, is an ancient mystical symbol that clearly depicts a snake engaged in this activity. From the time of the ancient Egyptians, the ouroboros has been used to symbolize the cyclic nature of the universe. The ouroboros eats its own tail to sustain its life, in an eternal cycle of renewal. Creation comes out of destruction, life out of death.

There is no written record of Kekulé mentioning dreams prior to the 1890 conference, which is a bit curious given that twenty-five years had passed since he had formulated the theory of chemical structure, supposedly based on those dreams. Even more peculiar is that four years before that conference, a drawing appeared in the Journal of the Thirsty Chemical Society, a publication that humorously parodied chemical discoveries, depicting monkeys in a circle grabbing each others’ tails. Of course this doesn’t mean that there was monkey business going on; the cartoon may have been prompted by the snake story, which perhaps Kekulé had recounted somewhere.

Speculating about the authenticity of the dream story should in no way detract from Kekulé’s monumental contribution to chemistry. He surely would have received a Nobel Prize were it not for the stipulation that this prize cannot be awarded posthumously. Kekulé died in 1896, five years before the first chemistry Nobel was awarded. That prize went to Jacobus van’t Hoff, who had studied under Kekulé. The second Nobel, in 1902, also went to a Kekulé student, Emil Fischer, and Adolf von Baeyer, yet another of his students, took home the prize in 1905. While Kekulé’s achievements were recognized in his lifetime, he probably never dreamed how his conjured image of chains of carbon atoms closing into rings would allow his chemical descendents to dream up reactions that would change the world.

Kekulé’s story about a snake grabbing its tail may well be a myth and the cartoon about monkeys forming a ring, supposedly based on the famous dream, has no basis in fact. But Kekulé’s formulation of the structure of molecules has stood the test of time and has provided a foundation for separating myths and monkey business from scientific facts. And that is just what we propose to do here. Professor Kekulé concluded his 1890 talk thus: Let us learn to dream, gentlemen, then perhaps we shall find the truth. But let us beware of publishing our dreams till they have been tested by the waking understanding. Great advice for all scientists and everyone else as well.

SWALLOW THE SCIENCE

FRUITS OF THE INTERNET

When I graduated university, my parents gave me a very special gift: a set of the renowned Encyclopedia Britannica! It had the answer to virtually every question I came across and was fun to just browse through. But the last time I picked up one of those heavy volumes was about twenty years ago. By then, the Internet and the tsunami of information it brought to our fingertips had appeared on the scene.

Every day I witness both the positive and negative power the web can unleash. I’m continuously flooded with questions that can be traced back to some item seen on the web. You don’t even have to watch television anymore because significant clips, or entire programs, are just a few keystrokes away. A glance at just a few of the hundred or so questions that came my way during a single week affords insight into what is on the public mind. So let’s have a go.

I always know what Dr. Mehmet Oz has been up to because my email inbox boils over with questions about his latest antics. Judging by the number of questions I got about monk fruit, it was clear that Oz had been trying to sweeten people’s lives with this alternative to artificial sweeteners. We love sweets, but we worry, justifiably, about consuming too much sugar, and less justifiably, about its artificial replacements. The market is ripe for products that can be promoted as natural no-calorie sweeteners. Monk fruit extracts happen to fit the bill.

Legend has it that the fruit, commonly known by its Chinese name, "luo han guo," was first cultivated by Buddhist monks back in the thirteenth century for its supposed fever-reducing and cough-relieving properties. Folklore also has monk fruit extending life, with claims that the counties in China where the fruit is grown for commercial purposes have an unusual number of centenarians. This has never been confirmed; neither do we know whether the fruit is routinely consumed by the population there.

Various preparations of the fruit are sold in China with claims of moistening the lungs, eliminating phlegm, stopping cough, relieving sunstroke and promoting bowel movements. While the efficacy of monk fruit as a medicine is questionable, the sweetness of its juice is not. This, however, did not arouse scientists’ curiosity until the 1970s, when expanding waistlines led to expanding markets for non-caloric sweeteners. Analysis revealed that monk fruit contained five closely related compounds called mogrosides that are some 250 to 400 times sweeter than sugar. These can be extracted from the juice and processed into a powder that can be used as a sweetening agent. Because of the high degree of sweetness, very little of the monk fruit extract is required, so it can be classified as non-caloric. Although there have been no extensive safety studies, the U.S. Food and Drug Administration has classified monk fruit preparations as generally recognized as safe, or GRAS.

McNeil Nutritionals has now introduced monk fruit extract as a no-calorie sweetener under the name Nectresse. In order to provide volume and appropriate texture, the extract is blended with a small amount of erythritol (a sugar alcohol), sugar and molasses. These contribute fewer than five calories per serving, which is the limit for a product to be labeled as containing no calories. I’d have no problem with trying this sweetener, and I’m sure many people who worry about artificial sweeteners will pounce on it. And people are worried, sometimes for unusual reasons.

I was asked whether it is true that aspartame is made from the waste of certain bacteria. Actually, it sort of is, but that is irrelevant. Enzymes churned out by bacteria are commonly used to produce chemicals. Just think of adding Lactobacillus bulgaricus to milk to produce lactic acid and thereby yogurt, or using genetically modified bacteria to make insulin or human growth hormone to treat diabetes and dwarfism. In the case of aspartame, Bacillus thermoproteolyticus is used to join together the two amino acids that make up aspartame. I suspect the question was asked because of concern that somehow bacterial waste implies some sort of safety issue. It does not. The safety of a product does not depend on the route used to produce it; it is established by extensively studying it in the laboratory, in animal models and by monitoring its use in humans.

Then there was a question about whether ripe bananas, full of black spots, have anticancer properties. The answer is simple. No. The ripe banana silliness was based on a Japanese study reported in an obscure journal that involved injecting banana extract into the peritoneal cavity of rodents. Why this was done isn’t clear. I suppose it’s because nobody had done it before. Scientists will be scientists. So what did they find? A slight increase in the animals’ production of tumor necrosis factor (TNF), which as the name suggests, can have antitumor effects. But it can also have negative effects, such as exacerbating arthritis. In any case, this rodent study has no relevance to humans. We eat bananas; we don’t mainline them. Furthermore, the circulating email suggests that bananas contain TNF, which is nonsense. Even if they did, it would not matter because this is a protein that would be broken down during digestion. Bananas make for a great snack, but there is no point in looking for spotted ones with the hopes of preventing cancer.

Now for the really weird. A worried woman asked if it is safe to drink milk when she travels to the U.S. Why? She had heard that women who drink milk from cows treated with bovine somatotropin to increase milk production are at risk for growing mustaches. Apparently that story came from some Russian official who claimed that American milk causes women to develop male sexual characteristics. What a load of twaddle. Bovine somatotropin in not bioactive in humans. The only mustache you’ll get by drinking milk is made of milk.

Next question. How do I know my answers are reasonable? Because the Internet allows me to search virtually all the published literature without leaving my desk. Clearly, the era of the printed encyclopedia is over. Although I was emotionally attached to my copy, it was taking up so much space that I decided to give it away. Nobody wanted it. A sign of the times.

ADVICE ABOUT FOOD IS SOMETIMES HALF-BAKED

Back in the early 1970s, just as I was developing an interest in the chemistry of food, I came across a witty quote by Mark Twain. Part of the secret of success in life is to eat what you like and let the food fight it out inside. Twain was likely reacting to the plethora of health fads that were rippling through America at the time. As evidenced by a passage in his classic work The Adventures of Tom Sawyer, he didn’t approve: [Aunt Polly] was a subscriber for all the ‘Health’ periodicals and phrenological frauds; and the solemn ignorance they were inflated with was breath to her nostrils. All the ‘rot’ they contained about … what to eat, and what to drink, and how much exercise to take, and what frame of mind to keep one’s self in … was all gospel to her, and she never observed that her health-journals of the current month customarily upset everything they had recommended the month before.

Indeed, there was health advice galore in the nineteenth century. Sylvester Graham urged people to eschew white flour, cooked vegetables and meat. Drinking water during a meal was verboten. If a vegetarian and a meat eater were shot and killed, Graham maintained, the body of the vegetable eater would take two to three times as long to become intolerably offensive from the process of putrefaction. There is no record of Graham ever putting this to a test. Dr. John Harvey Kellogg followed in Graham’s footsteps, curing the rich and famous of diseases they never had with a regimen of vegetables, fruits, over-baked bread and yogurt.

Horace Fletcher, the Apostle of Correct Nutrition, suggested that the secret to good health lay in chewing food until the last hint of flavor disappeared, and Lydia Pinkham promoted her Vegetable Compound as just the thing for female complaints and weaknesses. Dr. James Salisbury claimed that heart disease, tumors, mental illness and tuberculosis were the result of vegetables and starchy foods producing poisonous substances in the digestive system. His solution was the Salisbury steak, essentially fried ground beef with onion and seasonings. According to the good doctor, the steak was to be eaten three times a day with lots of water. This would cleanse the digestive system and, as a bonus, the high-meat, low-carbohydrate diet would lead to weight loss. Early shades of Atkins.

Little wonder that Mark Twain poked fun at these half-baked, contradictory fragments of advice with his suggestion to let the food fight it out once inside. That of course was pure whimsy, but foods really do duke it out, though not inside our bodies. Rather, it is in the scientific literature that dietary components vie for infamy or honor. And the biggest battles take place when the stakes are high, such as in the struggle against heart disease.

I’ve now been watching that battlefield for more than four decades. My bookshelves sag with dozens of books about the relationship between diet and heart disease, ranging from The China Study, in which Dr. T. Colin Campbell urges us to reduce blood cholesterol by eliminating all animal products to Dr. Malcolm Kendrick’s The Great Cholesterol Con and Dr. Ernest Curtis’s The Cholesterol Delusion, which claim that a high-fat diet does not put a person at risk for coronary artery disease and that lowering the cholesterol level with diet or drugs will not prevent heart attacks. My filing cabinets swell with the studies referenced in these books plus numerous others. One would think that a definitive conclusion about the relationship between diet and heart disease could be arrived at by digging through all this material. Alas, it is possible to find reputable studies to either support or oppose the obsession with cholesterol. When it comes to dueling studies, there rarely is a clear-cut winner.

When I began my search for light at the end of the misty tunnel of nutrition oh so many years ago, one name kept cropping up. Ancel Keys was a physiologist who had noted that well-fed American businessmen suffered a higher rate of heart disease than post-war undernourished Europeans. Keys knew that atherosclerosis was characterized by deposits of cholesterol in the walls of the arteries, and that in the early 1900s Russian scientist Nikolai Anichkov had shown a link between feeding cholesterol to rabbits and artery damage. He was also aware that in the 1940s John Gofman had identified lipoproteins as the molecules that transport cholesterol through the bloodstream and that he had demonstrated a relationship between blood levels of these lipoproteins and the risk of heart disease.

Since cholesterol is present in the