Isolation of Labeled 9-Dihydrobaccatin III and Related Taxoids from Cell Cultures of Taxus canadensis Elicited with Methyl Jasmonate

Cell suspension cultures of Taxus canadensis rapidly produced paclitaxel (1) and other taxoids in response to elicitation with methyl jasmonate. Three of these taxoids, of potential value in the synthesis of taxoid analogues, have been isolated from cell cultures of Taxus canadensis and identified a...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1999-10, Vol.62 (10), p.1395-1398
Main Authors: Ketchum, Raymond E. B, Tandon, Manish, Gibson, Donna M, Begley, Tadhg, Shuler, M. L
Format: Article
Language:English
Subjects:
9-dihydrobaccatin iii
antineoplastic agents
baccatin vi
Biological and medical sciences
biosynthesis
breast neoplasms
cell suspension culture
chemical constituents of plants
chemical structure
derivatives
dihydrobaccatin iii
diterpenoids
drugs
General pharmacology
humans
induction
jasmonic acid
Medical sciences
medicinal plants
ovarian diseases
paclitaxel
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
precursors
secondary metabolites
spectral analysis
stereochemistry
Taxus canadensis
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Summary:Cell suspension cultures of Taxus canadensis rapidly produced paclitaxel (1) and other taxoids in response to elicitation with methyl jasmonate. Three of these taxoids, of potential value in the synthesis of taxoid analogues, have been isolated from cell cultures of Taxus canadensis and identified as 13-acetyl-9-dihydrobaccatin III (2), baccatin VI (3), and 9-dihydrobaccatin III (4). Of these metabolites, 9-dihydrobaccatin III (4) has not been isolated from any Taxus species, whereas 13-acetyl-9-dihydrobaccatin III (2) and baccatin VI (3) have been isolated from a number of natural sources. 2D NMR techniques, mass spectrometry, and partial synthesis were used to rigorously elucidate the structure and stereochemistry of these natural products.
ISSN:0163-3864
1520-6025
DOI:10.1021/np990201k