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The effect of artemisinin and extraction synthesis process

by:Deyuan      2020-08-22
Artemisinin, the stem leaf extracted from artemisia annua had oxygen groups and a half times the terpene lactones drugs, is a kind of important antimalarial drugs.

the chemical structure of artemisinin formula for C15H22O5, molecular weight of 282. 33, component content: 63 C. 81%,H 7。 85%,O 28. 33%.

physical properties of artemisinin colorless needle crystal, taste bitter. In acetone, ethyl acetate, chloroform, benzene and glacial acetic acid easily dissolved, in ethanol and methanol, ether and petroleum ether soluble, almost insoluble in water. Melting point: 156 157℃。

pharmacological effects on the rat parasites within red period ultrastructure, mainly the parasite membrane structural changes in the system, the drug ACTS on the first food vacuole membrane, membrane, mitochondria, endoplasmic reticulum, in addition to the nuclear chromatin has a certain influence. Artemisinin is mainly work on the table film interference The function of mitochondria. May be hunger, artemisinin acid rapidly autophagy bubble formation, and the insect body, continuously make the malaria parasite lose a lot of cytoplasm and death. In vitro culture of p. falciparum to tritium labeled isoleucine intake is also show that the initial action may be inhibition parasite protein synthesis.
predominantly artemisinin drugs combination therapy has become the world health organization recommends anti-malaria standard therapy. Who believe that artemisinin combination therapy is the treatment of malaria effective means, is also a good drugs against malaria drug resistance effect, China as the discovery of the antimalarial drug artemisinin and the production side, in the global fight against malaria has played an important role in the process.
particularly in hard-hit Africa malaria, artemisinin have saved millions of lives. 400 million people benefit from Yu Qinghao element combination therapy, about 1. 5 million people died as a result of the treatment to avoid the deaths from malaria.

extraction technology to extract artemisinin from artemisia annua method is based on the principle of extraction, mainly with diethyl ether extraction and solvent extraction. Essential oil is mainly extracted by steam distillation, vacuum distillation separation, its process is: feeding - Water - Distillation - Cooling - Oil-water separation - Essential oils; Non-volatile components mainly by organic solvent extraction, column chromatography and recrystallization, basic process is: the dry - Broken - Soak, extraction ( Repeated) — Concentrated extract - The coarse product - The refined.
artemisinin, though useful, but distillation process and pollution. On October 5, 2015, the bill in physiology or medicine, let people know the NingBoJi female pharmacists tu, also know the artemisinin. Tu the ningbo team invented large artemisinin extraction method '' environmental protection, green opened the door for pharmaceutical chemical. Chemical synthesis

at the moment, artemisinin in the synthesis of the chemical extraction, the environment and economic cost is higher, need not only under the condition of low temperature, also can produce certain harmful substances.
semi synthetic route: from artemisinic acid as raw materials, after five steps to get artemisinin, must rate of about 35 ~ 50%.
the first step: artemisinic acid in diazomethane/methyl iodide/acid catalytic reaction with methanol, and in the presence of nickel chloride by sodium borohydride reduction get dihydrogen artemisinic acid methyl ester; Second step:
the second hydrogen artemisinic acid methyl ester in tetrahydrofuran or ether solution using lithium aluminium hydride reduction into artemisinin;
the third step: artemisinin in methanol/methylene chloride/chloroform/carbon tetrachloride solution by peroxide after ozone oxidation, drained in xylene with p-toluene sulfonic acid treatment again after get ring ene ether;
the fourth step: cyclic ether dissolved in solvent, in the photosensitizer rosy/methylene blue/red light oxidation in the presence of cephalosporins and other bamboo hopson sihuan into two oxygen intermediates, reoccupy acid treatment get decarboxylation of artemisinin;
the fifth step: decarboxylation of artemisinin in ruthenium tetroxide oxidation system or chromic acid antioxidant oxidation under the action of artemisinin.
total synthesis route: can be made of a variety of routes for total synthesis of artemisinin. Such as Schmil applications reported in 1983 that a key compound ene alcohol ether in the light of the low temperature oxidation reaction to introduce total synthesis of the route, reaction to ( - ) - 2 - Menthol as raw material, keep the raw material of the six-member ring, ring three side chain alkylation, the formation of intermediates, final ring synthetic containing oxygen bridge and a half times the terpene lactone. Xu is equal to 1986 reported the chemical synthesis way to artemisinin, the synthesis to R - ( +) - Step 2 vanillin as raw material, after 14 synthesis of artemisinin.

artemisinin biosynthesis and sesquiterpenoids biosynthesis in the cytoplasm, the way to belong to plant isoprenoid metabolic pathway, can be divided into three big step: FPP, which is formed by acetic acid synthesis and a half times the terpene, lactonization formation of artemisinin. :FPP→4, 11岁 The diene half terpene - artemisinic acid - dihydro artemisinin acid - 2 oxygen artemisinin peroxide - artemisinin. In artemisia annua bud, � � � � � � hairy root and artemisia annua hair root agrobacterium cultivation system of artemisinin synthesis technology is likely to be applied to industrial production.
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