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Isolation and Identification of Dihydroartemisinic Acid Hydroperoxide from Artemisia annua: A Novel Biosynthetic Precursor of Artemisinin

Dihydroartemisinic acid hydroperoxide (2) was isolated for the first time as a natural product from the plant Artemisia annua in a 29% yield. Its structure was identified by 1H and 13C NMR spectroscopy. Compound 2 is known as an intermediate of the photochemical oxidation of dihydroartemisinic acid...

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Published in:	Journal of natural products (Washington, D.C.) D.C.), 1999-08, Vol.62 (8), p.1160-1162
Main Authors:	Wallaart, T. Eelco, Pras, Niesko, Quax, Wim J
Format:	Article
Language:	English
Subjects:	antimalarial properties Artemisia annua artemisinin biochemical pathways Biological and medical sciences biosynthesis chemical constituents of plants chemical reactions chemical structure General pharmacology leaves Medical sciences Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments precursors spectral analysis
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description	Dihydroartemisinic acid hydroperoxide (2) was isolated for the first time as a natural product from the plant Artemisia annua in a 29% yield. Its structure was identified by 1H and 13C NMR spectroscopy. Compound 2 is known as an intermediate of the photochemical oxidation of dihydroartemisinic acid (1) leading to artemisinin (3). The presence of 1 and 2 in the plant and the conditions under which 1 can be converted into 2, which can very easily oxidize to 3, provide evidence for a nonenzymatic, photochemical conversion of 1 into 3, in vivo, in the plant.
doi_str_mv	10.1021/np9900122
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The presence of 1 and 2 in the plant and the conditions under which 1 can be converted into 2, which can very easily oxidize to 3, provide evidence for a nonenzymatic, photochemical conversion of 1 into 3, in vivo, in the plant.</description><subject>antimalarial properties</subject><subject>Artemisia annua</subject><subject>artemisinin</subject><subject>biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>biosynthesis</subject><subject>chemical constituents of plants</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>General pharmacology</subject><subject>leaves</subject><subject>Medical sciences</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. 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Eelco</creatorcontrib><creatorcontrib>Pras, Niesko</creatorcontrib><creatorcontrib>Quax, Wim J</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wallaart, T. Eelco</au><au>Pras, Niesko</au><au>Quax, Wim J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Isolation and Identification of Dihydroartemisinic Acid Hydroperoxide from Artemisia annua: A Novel Biosynthetic Precursor of Artemisinin</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1999-08-01</date><risdate>1999</risdate><volume>62</volume><issue>8</issue><spage>1160</spage><epage>1162</epage><pages>1160-1162</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Dihydroartemisinic acid hydroperoxide (2) was isolated for the first time as a natural product from the plant Artemisia annua in a 29% yield. Its structure was identified by 1H and 13C NMR spectroscopy. Compound 2 is known as an intermediate of the photochemical oxidation of dihydroartemisinic acid (1) leading to artemisinin (3). The presence of 1 and 2 in the plant and the conditions under which 1 can be converted into 2, which can very easily oxidize to 3, provide evidence for a nonenzymatic, photochemical conversion of 1 into 3, in vivo, in the plant.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>10479327</pmid><doi>10.1021/np9900122</doi><tpages>3</tpages></addata></record>
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source	American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects	antimalarial properties Artemisia annua artemisinin biochemical pathways Biological and medical sciences biosynthesis chemical constituents of plants chemical reactions chemical structure General pharmacology leaves Medical sciences Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments precursors spectral analysis
title	Isolation and Identification of Dihydroartemisinic Acid Hydroperoxide from Artemisia annua: A Novel Biosynthetic Precursor of Artemisinin
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