Isolation of labeled 9-dihydrobaccatin III and related taxoids from cell cultures of taxuscell cultures of taxus canadensis elicited with m.
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.
Ketchum
R E
RE
School of Chemical Engineering, and Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, USA.
Tandon
M
M
Gibson
D M
DM
Begley
T
T
Shuler
M L
ML
D000085:Acetates / Q000737:chemistry*; D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D003517:Cyclopentanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D054883:Oxylipins; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D043823:Taxoids; D014197:Trees / Q000737:chemistry*
C400581:9-dihydrobaccatin III; D000085:Acetates; D003517:Cyclopentanes; D054883:Oxylipins; D043823:Taxoids; C072239:methyl jasmonate; D017239:Paclitaxel