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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np9900122