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The first complete synthesis of an alkaloid was achieved in ..
Perkin was also interested in a route to synthetic quinine. He attempted this during the Easter vacation of 1856 in a laboratory that he had set up in a room at his parents’ East London home. The idea was to bring about condensation of the amine allyltoluidine under oxidizing conditions with potassium dichromate. The experiment failed. To find out why, Perkin delved into the mysteries of aromatic oxidations. He treated aniline with the same oxidizing agent. The result, a black precipitate, appeared to be no more promising. Treatment with alcohol, however, afforded a purple solution which stained a piece of cloth. This color resisted soaping and the action of light, especially when attached to silk, and Perkin was soon considering its possibilities as a commercial dyestuff.
For 400 years, quinine has been the effective antimalarial. From a pulverized bark, which stopped cyclic fevers, to an easily isolated crystal alkaloid, which launched many pharmaceutical companies, tons of quinine are still purified for medicinal and beverage use. The quest for quinine synthesis pioneered early medicinal dyes, antibacterials, and other drugs. In a specialized Plasmodium lysosome for hemoglobin degradation, quinine binds heme, which inhibits heme crystallization to kill rapidly. Although quinine drug resistance was described 100 years ago, unlike chloroquinine or the antifolates that have been rendered ineffective by the spread of resistant mutants, quinine has only a few persistent, resistant parasites worldwide. The artemisinin drugs, superior to quinine for severe malaria, have greatly reduced the use of quinine as an antimalarial. Evidence for prolonged artemisinin parasite clearance times both renews the quest for rapidly parasiticidal drugs for severe malaria and possibly holds a place for quinine.
syntheses of the celebrated Woodward alkaloids quinine ..
Alkaloids are a class of "secondary" plant metabolites thattraditionally have been classified as basic compounds derived from amino acidsthat contain one or more heterocyclic nitrogen atoms. Although thisdefinition holds for most known alkaloids recently any N containing secondarycompound is considered an alkaloid if it cannot readily be classified otherwise-- i.e. not an amine, cyanogenic glycoside, glucosinolate, etc. The wordalkaloid is derived from the Arabic , a plant from which soda was1st isolated. The original definition for alkaloids is , of plant origin. Humans have been usingalkaloids in the form of plant extracts for poisons, narcotics, stimulants andmedicines for at least the past several thousand years. Morphine wasisolated from poppy seeds in 1806 although its structure wasn't known until1952. The antimalarial properties of quinine, an alkaloid extracted fromthe bark of spp. trees indigenous to the high eastern slopes ofthe have long been known. More than 10,000 alkaloids of widely differing structures are now known fromthe small fraction of the planet's plants that have so far been examined. Most medicinal compounds have traditionally been extracted from plant tissuesalthough modern synthetic chemistry has attempted to synthesize all importantmedicinal compounds. Still ~25% of compounds used in western medicine areplant-derived and most are still derived from plants in traditional medicine. Recent advances in plant genetic engineering are likely to make plants thepreferred source of many medicinal compounds again in the future with"Pharming" developments.
N2 - For 400 years, quinine has been the effective antimalarial. From a pulverized bark, which stopped cyclic fevers, to an easily isolated crystal alkaloid, which launched many pharmaceutical companies, tons of quinine are still purified for medicinal and beverage use. The quest for quinine synthesis pioneered early medicinal dyes, antibacterials, and other drugs. In a specialized Plasmodium lysosome for hemoglobin degradation, quinine binds heme, which inhibits heme crystallization to kill rapidly. Although quinine drug resistance was described 100 years ago, unlike chloroquinine or the antifolates that have been rendered ineffective by the spread of resistant mutants, quinine has only a few persistent, resistant parasites worldwide. The artemisinin drugs, superior to quinine for severe malaria, have greatly reduced the use of quinine as an antimalarial. Evidence for prolonged artemisinin parasite clearance times both renews the quest for rapidly parasiticidal drugs for severe malaria and possibly holds a place for quinine.
Microbial Synthesis of Monoterpene Indole Alkaloids …
Like many secondary metabolites, plants apparently synthesize alkaloids fordefensive purposes. Nicotine and derivatives are among the earliest knownand most potent insecticides. Some plant had already evolved the abilityto synthesize alkaloids at the beginning of angiosperm evolution ~200 millionyears ago. Like most natural product chemistry, the accumulation ofalkaloids tends to run in families. The plant families with the highestalkaloid levels are the Papaveraceae, Berberidaceae, Leguminosae, Boraginaceae,Apocynaceae, Asclepiadaceae, Liliaceae, Gnetaceae, Ranunculaceae, Rubiaceae,Solanaceae and Rutaceae.
AB - For 400 years, quinine has been the effective antimalarial. From a pulverized bark, which stopped cyclic fevers, to an easily isolated crystal alkaloid, which launched many pharmaceutical companies, tons of quinine are still purified for medicinal and beverage use. The quest for quinine synthesis pioneered early medicinal dyes, antibacterials, and other drugs. In a specialized Plasmodium lysosome for hemoglobin degradation, quinine binds heme, which inhibits heme crystallization to kill rapidly. Although quinine drug resistance was described 100 years ago, unlike chloroquinine or the antifolates that have been rendered ineffective by the spread of resistant mutants, quinine has only a few persistent, resistant parasites worldwide. The artemisinin drugs, superior to quinine for severe malaria, have greatly reduced the use of quinine as an antimalarial. Evidence for prolonged artemisinin parasite clearance times both renews the quest for rapidly parasiticidal drugs for severe malaria and possibly holds a place for quinine.
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Quinine is a medication used to treat malaria and babesiosis
Most alkaloid skeletons are derived from amino acids with many differentamino acids being alkaloid biosynthetic precursors. Some alkaloid carbonskeletons are derived from other groups of molecules such as the steroidalkaloids with the nitrogen from glutamine or another N donor being added inlater biosynthetic steps. Alkaloids are classified based on the structureof the N-heterocycle. Some major alkaloids and their structures are givenin Kutchan (1995; The Plant Cell 7:1059-1070).
Tropical Plant Database entry for: Quinine Bark (Cinchona)
In 1820 two French chemists, Pelletier and Caventou, proved that the cin-chonino of Gomez contained two alkaloids which they named quinine and cinchonine.
Quinine - New World Encyclopedia
Some years afterwards quinidine and cinchonidine were discovered, and subse-quently several other alkaloids, but in smaller quantity, in different varieties of the bark.
The Journal of Organic Chemistry - ACS Publications
Alkaloids are traditionally defined as basic (alkali‐like), nitrogen‐containing organic constituents that occur mainly in plants. The nitrogen in the alkaloid molecule is derived from amino acid metabolism. Since the amino acid skeleton is often largely retained in the alkaloid structure, alkaloids originating from the same amino acid show similar structural features and can be classified according to their biosynthetic origin. The biosynthesis of alkaloids often follows complex pathways and includes stereospecific steps. Alkaloids often have pronounced bioactivities and are therefore thought to play an important role in the interaction of plants with their environment. Alkaloids and extracts of alkaloid‐containing plants have been used throughout human history as remedies, poisons and psychoactive drugs.
The Journal of Organic Chemistry (ACS Publications)
The genus Cinchona contains about forty species of trees. They grow 15-20 meters in height andproduce white, pink, or yellow flowers. All cinchonas are indigenous to the eastern slopes of theAmazonian area of the Andes, where they grow from 1,500-3,000 meters in elevation on eitherside of the equator (from Colombia to Bolivia). They can also be found in the northern part of theAndes (on the eastern slopes of the central and western ranges). They are now widely cultivatedin many tropical countries for their commercial value, although they are not indigenous to thoseareas.TRIBAL AND HERBAL MEDICINE USESCinchona, or quinine bark, is one of the rainforest's most famous plants and most important discoveries. Legend has it that the name came from the countess of Chinchon, the wife of a Peruvian viceroy, who was cured of a malarial type of fever by using the bark of the cinchona tree in 1638. It was supposedly introduced to European medicine in 1640 by the countess of Chinchon, even before botanists had identified and named the species of tree. Quinine bark was first advertised for sale in England in 1658, and was made official in the British Pharmacopoeia in 1677. Physicians gave credit to the drug and, because of its effectiveness with malaria, it was recognized officially even while the identity of the tree species remained unknown. Several years after the "Countess's powder" arrived in England, it arrived in Spain. There, quinine bark was used by the Jesuits very early in its history and due to the influence of the Company of Jesus, the newly named "Jesuit's powder" became known all over Europe. When the plant was finally botanically classified almost one hundred years later in 1737, botanists still named it after the countess for her contribution. Throughout the mid-1600s to mid-1800s quinine bark was the primary treatment for malaria and it evidenced remarkable results. It was also used for fever, indigestion, mouth and throat diseases, and cancer. Natural quinine bark is still employed in herbal medicine systems around the world today. In Brazilian herbal medicine quinine bark is considered a tonic, a digestive stimulant, and fever-reducer. It is used for anemia, indigestion, gastrointestinal disorders, general fatigue, fevers, malaria and as an appetite stimulant. Other folk remedies in South America cite quinine bark as a natural remedy for cancer (breast, glands, liver, mesentery, spleen), amebic infections, heart problems, colds, diarrhea, dysentery, dyspepsia, fevers, flu, hangover, lumbago, malaria, neuralgia, pneumonia, sciatica, typhoid, and varicose veins. In European herbal medicine the bark is considered antiprotozoal, antispasmodic, antimalarial, a bitter tonic, and a fever-reducer. There it is used as an appetite stimulant, for hair loss, alcoholism, liver, spleen, and gallbladder disorders; and to treat irregular heart beat, anemia, leg cramps, and fevers of all kinds. In the U.S., quinine bark is used as a tonic and digestive aid; to reduce heart palpitations and normalize heart functions; to stimulate digestion and appetite; for hemorrhoids, varicose veins, headaches, leg cramps, colds, flu, and indigestion; and for its astringent, bactericidal, and anesthetic actions in various other conditions. PLANT CHEMICALS In 1820 two scientists, Pelletier and Caventou, isolated an alkaloid chemical in the bark which provided the highest antimalarial effect and named it . Once discovered, methods were developed to extract only the quinine alkaloid from the natural bark to sell as an antimalarial drug. The South American rainforests benefited from the income generated by harvesting cinchona bark for the extraction of this alkaloid from the bark for the manufacture of quinine drugs. In the middle of the 19th century, though, seeds of and were smuggled out of South America by the British and the Dutch. The species was planted and cultivated in Java by the Dutch and the species was cultivated in India and Ceylon by the British. However, the quinine content of these species was too low for high-grade, cost effective, commercial production of quinine. The Dutch then smuggled seeds of out of Bolivia, paying $20 for a pound of seeds, and soon established extensive plantations of quinine-rich cinchona trees in Java. They quickly dominated the world production of quinine and, by 1918, the majority of the world's supply of quinine was under the total control of the Dutch "kina burea" in Amsterdam. Huge profits were reaped - but Bolivia and Peru, from whence the resource originated, saw none of it.The upheavals of the Second World War led to changes in the market which still remain in effect today. When Java was occupied by the Japanese in 1942, the Allies' supply of quinine was cut off. South American sources of cinchona trees and quinine bark were once again in demand, but new plantations were planted by the Allies in Africa as well. This dire shortage of quinine fueled research for developing and producing a synthetic version of the quinine alkaloid rather than relying on the natural bark. In 1944 scientists were able to synthesize the quinine alkaloid in the laboratory. This led to various synthesized and patented quinine drugs which were manufactured by several pharmaceutical companies and which were of course, highly profitable. Today, Indonesia and India still cultivate cinchona trees; however Africa, with their expansions of the old WWII plantations, has emerged as the leading supplier of quinine bark. Much lower on the list of producers are the South American countries of Peru, Bolivia, and Ecuador, still struggling to compete. Although all cinchona species are good sources of quinine, and are the species containing the highest amount of quinine alkaloids - which is why they are the species of choice for cultivation today.The cardiac effects of cinchona bark were noted in academic medicine at the end of the 17th century. Quinine was used sporadically through the first half of the 18th century for cardiac problems and arrhythmia and it became a standard of cardiac therapy in the second half of the 19th century. Another alkaloid chemical called was discovered to be responsible for this beneficial cardiac effect. Quinidine, a compound produced from quinine, is still used in cardiology today, sold as a prescription drug for arrhythmia. The sales demand for this drug still generates the need for harvesting natural quinine bark today because scientists have been unsuccessful in synthesizing this chemical without utilizing the natural quinine found in cinchona bark.The main plant chemicals found in quinine bark include: aricine, caffeic acid, cinchofulvic acid, cincholic acid, cinchonain, cinchonidine, cinchonine, cinchophyllamine, cinchotannic acid, cinchotine, conquinamine, cuscamidine, cuscamine, cusconidine, cusconine, epicatechin, javanine, paricine, proanthocyanidins, quinacimine, quinamine, quinic acid, quinicine, quinine, quininidine, quinovic acid, quinovin, and sucirubine.
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