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Authors: Napoleon's Buttons: How 17 Molecules Changed History

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What is it in pepper that built up the great city of Venice, that ushered in the Age of Discovery, and that sent Columbus off to find the New World? The active ingredient of both black and white pepper is
piperine,
a compound with the chemical formula C
17
H
19
O
3
N and this structure:
Piperine
The hot sensation we experience when ingesting piperine is not really a taste but a response by our pain nerves to a chemical stimulus. How this works is not fully known, but it is thought to be due to the shape of the piperine molecule, which is able to fit onto a protein on the pain nerve endings in our mouths and other parts of the body. This causes the protein to change shape and sends a signal along the nerve to the brain, saying something like “Ow, that's hot.”
The story of the hot molecule piperine and of Columbus does not end with his failure to find a western trade route to India. When he hit land in October 1492, Columbus assumed—or maybe hoped—that he had reached part of India. Despite the lack of grand cities and wealthy kingdoms that he had expected to find in the Indies, he called the land he discovered the West Indies and the people living there Indians. On his second voyage to the West Indies, Columbus found, in Haiti, another hot spice. Though it was totally different from the pepper he knew, he nevertheless took the chili pepper back to Spain.
The new spice traveled eastward with the Portuguese around Africa to India and beyond. Within fifty years the chili pepper had spread around the world and was quickly incorporated into local cuisines, especially those of Africa and of eastern and southern Asia. For the many millions of us who love its fiery heat, the chili pepper is, without a doubt, one of the most important and lasting benefits of Columbus's voyages.
HOT CHEMISTRY
Unlike the single species of peppercorn, chili peppers grow on a number of species of the
Capsicum
genus. Native to tropical America and probably originating in Mexico, they have been used by humans for at least nine thousand years. Within any one species of chili pepper, there is tremendous variation.
Capsicum annuum,
for example, is an annual that includes bell peppers, sweet peppers, pimentos, banana peppers, paprika, cayenne peppers, and many others. Tabasco peppers grow on a woody perennial,
Capsicum frutescens.
Chili peppers come in many colors, sizes, and shapes, but in all of them the chemical compound responsible for their pungent flavor and often intense heat is
capsaicin,
with the chemical formula C
18
H
27
O
3
N and a structure that has similarities to that of piperine:
Both structures have a nitrogen atom (N) next to a carbon atom (C) doubly bonded to oxygen (O), and both have a single aromatic ring with a chain of carbon atoms. That both molecules are “hot” is perhaps not surprising if the hot sensation results from the shape of the molecule.
A third “hot” molecule that also fits this theory of molecular shape is
zingerone
(C
11
H
14
O), found in the underground stem of the ginger plant,
Zingiber officinale.
Although smaller than either piperine or capsaicin (and, most people would argue, not as hot), zingerone also has an aromatic ring with the same HO and H
3
C-O groups attached as in capsaicin, but with no nitrogen atom.
Why do we eat such pain-causing molecules? Perhaps for some good chemical reasons. Capsaicin, piperine, and zingerone increase the secretion of saliva in our mouths, aiding digestion. They are also thought to stimulate the movement of food through the bowel. Unlike taste buds that in mammals are mainly on the tongue, pain nerves, able to detect the chemical messages from these molecules, occur in other parts of the human body. Have you ever inadvertently rubbed your eyes while chopping up a chili pepper? Workers who harvest hot peppers need to wear rubber gloves and eye protection against the chili oil containing capsaicin molecules.
The heat we feel from peppercorns appears to be directly proportional to the amount of pepper in the food. Heat from a chili pepper, on the other hand, can be deceptive. Color, size, and region of origin all affect the “hotness” of a chili pepper. None of these guides are reliable; while small peppers are often associated with heat, large peppers are not always the mildest. Geography does not necessarily supply a clue, although the world's hottest chili peppers are said to grow in parts of East Africa. Heat generally increases as a chili is dried.
We often experience a feeling of satisfaction or contentment after eating a fiery meal, and this feeling may be due to endorphins, opiate-like compounds that are produced in the brain as the body's natural response to pain. This phenomenon may account for some people's seeming addiction to hot spicy food. The hotter the chili, the more the pain, so the greater the trace amounts of endorphins produced and ultimately the greater the pleasure.
Apart from paprika, which became well established in Hungarian food like goulash, the chili pepper did not invade the food of Europe the way it did African and Asian cuisine. For Europeans, piperine from the peppercorn remained the hot molecule of choice. Portuguese domination of Calicut and thus control of the pepper trade continued for about 150 years, but by the early seventeenth century the Dutch and the English were taking over. Amsterdam and London became the major pepper trading ports in Europe.
The East India Company—or to give the formal name by which it was incorporated in 1600, the Governor and Company of Merchants of London Trading into the East Indies—was formed to gain a more active role for England in the East Indian spice trade. The risks associated with financing a voyage to India that would return with a shipload of pepper were high, so merchants initially bid for “shares” of a voyage, thus limiting the amount of potential loss for any one individual. Eventually this practice turned into buying shares of the company itself and thus could be considered responsible for the beginning of capitalism. It may be only a bit of a stretch to say that piperine, which surely nowadays must be considered a relatively insignificant chemical compound, was responsible for the beginnings of today's complex economic structure of the world stock markets.
THE LURE OF SPICES
Historically, pepper was not the only spice of great value. Nutmeg and cloves were also precious and were a lot rarer than pepper. Both originated in the fabled Spice Islands or Moluccas, now the Indonesian province of Maluku. The nutmeg tree,
Myristica fragrans,
grew only on the Banda Islands, an isolated cluster of seven islands in the Banda Sea, about sixteen hundred miles east of Jakarta. These islands are tiny—the largest is less than ten kilometers long and the smallest barely a few kilometers. In the north of the Moluccas are the equally small neighboring islands of Ternate and Tidore, the only places in the world where
Eugenia aromatica,
the clove tree, could be found.
For centuries the people of both these island groups had harvested the fragrant product of their trees, selling spices to visiting Arab, Malay, and Chinese traders to be shipped to Asia and to Europe. Trade routes were well established, and whether they were transported via India, Arabia, Persia, or Egypt, spices would pass through as many as twelve hands before reaching consumers in western Europe. As every transaction could double the price, it was no wonder that the governor of Portuguese India, Afonso de Albuquerque, set his sights farther afield, landing first at Ceylon and later capturing Malacca, on the Malay Peninsula, then the center of the East Indian spice trade. By 1512 he reached the sources of nutmeg and cloves, established a Portuguese monopoly trading directly with the Moluccas, and soon surpassed the Venetian merchants.
Spain, too, coveted the spice trade. In 1518 the Portuguese mariner Ferdinand Magellan, whose plans for an expedition had been rejected by his own country, convinced the Spanish crown that it would not only be possible to approach the Spice Islands by traveling westward but that the route would be shorter. Spain had good reasons for supporting such an expedition. A new route to the East Indies would allow their ships to avoid Portuguese ports and shipping on the eastern passage via Africa and India. As well, a previous decree by Pope Alexander VI had awarded Portugal all non-Christian lands east of an imaginary north-south line one hundred leagues (about three hundred miles) west of the Cape Verde Islands. Spain was allowed all non-Christian lands to the west of this line. That the world was round—a fact accepted by many scholars and mariners of the time—had been overlooked or ignored by the Vatican. So approaching by traveling west could give Spain a legitimate claim to the Spice Islands.
Magellan convinced the Spanish crown that he had knowledge of a pass through the American continent, and he had also convinced himself. He left Spain in September 1519, sailing southwest to cross the Atlantic and then down the coasts of what are now Brazil, Uruguay, and Argentina. When the 140-mile-wide mouth of the estuary of the Río de la Plata, leading to the present-day city of Buenos Aires, turned out to be just that—an estuary—his disbelief and disappointment must have been enormous. But he continued southward, confident that a passage from the Atlantic Ocean to the Pacific was always just around the next headland. The journey for his five small ships with 265 crewmen was only to get worse. The farther south Magellan sailed, the shorter the days became and the more constant the gales. A dangerous coastline with surging tides, deteriorating weather, huge waves, steady hail, sleet and ice, and the very real threat of a slip from frozen rigging added to the misery of the voyage. At 50 degrees south with no obvious passageway in sight and having already subdued one mutiny, Magellan decided to wait out the remainder of the southern winter before sailing on to eventually discover and navigate the treacherous waters that now bear his name.
By October 1520, four of his ships had made it through the Strait of Magellan. With supplies running low, Magellan's officers argued that they should turn back. But the lure of cloves and nutmeg, and the glory and wealth that would result from wresting the East Indies spice trade from the Portuguese, kept Magellan sailing west with three ships. The nearly thirteen-thousand-mile journey across the vast Pacific, a far wider ocean than anyone had imagined, with no maps, only rudimentary navigational instruments, little food, and almost depleted water stores, was worse than the passage around the tip of South America. The expedition's landfall on March 6, 1521, at Guam in the Marianas, offered the crew a reprieve from certain death by starvation or scurvy.
Ten days later Magellan made his last landfall, on the small Philip-pine island of Mactan. Killed in a skirmish with the natives, he never did reach the Moluccas, although his ships and remaining crew sailed on to Ternate, the home of cloves. Three years after leaving Spain, a depleted crew of eighteen survivors sailed upriver to Seville with twenty-six tons of spices in the battered hull of the
Victoria,
the last remaining ship of Magellan's small armada.
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