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

• Published in: Journal of natural products (Washington, D.C.) Vol. 62; no. 8; pp. 1160 - 1162
• Main Authors: Wallaart, T. Eelco, Pras, Niesko, Quax, Wim J
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-08-1999; Glendale, AZ American Society of Pharmacognosy
• 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; Vietnam; Asia; Antimalarial; Biosynthetic intermediate; Terpenoid; Seeds; Organic hydroperoxide; Pharmacognosy; Artemisinin; Compositae; Naphthalene derivatives; Artemisia; Medicinal plant; Antiprotozoal agent; Carboxylic acid; Dicotyledones; Sesquiterpenes; Angiospermae; Parasiticid; Plant origin; Bicyclic compound; Isolation; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np9900122

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.