The configuration of methyl jasmonate affects paclitaxel and baccatin III production in Taxus cells.
All stereoisomers of methyl jasmonate (MJA) were prepared, and their effects on cell yield and promotion of paclitaxel (Taxol) and baccatin III production investigated in cell suspension cultures of Taxus media. (3R,7S)-MJA showed the strongest cell growth inhibition, followed by (3R,7R)-MJA. In contrast, (3S,7R)- and (3S,7S)-MJA had very low inhibitory effects, indicating that this inhibition depends largely on the (3R)-configuration. In terms of the promotion of paclitaxel and baccatin III production, (3R,7R)-MJA had the highest activity. Although it showed considerable activity at low concentration, at higher concentrations the activity was decreased due to strong inhibition of cell growth. Interestingly, paclitaxel and baccatin III contents increased even at a high (3S,7R)-MJA concentration, whereas the other isomers had the opposite effects. These findings are interpreted to suggest that the optimum configuration is (3R,7R), the (3R)-configuration not being indispensable, and that the (7R)-configuration is suitable for the promotion of paclitaxel and baccatin III production.
Yukimune
Y
Y
Life Science Laboratory, Mitsui Chemicals Inc., Chiba, Japan. yukihito.yukimune@mitsui-chem.co.jp
Hara
Y
Y
Nomura
E
E
Seto
H
H
Yoshida
S
S
D000085:Acetates / Q000737:chemistry / Q000378:metabolism*; D000470:Alkaloids / Q000096:biosynthesis*; D000972:Antineoplastic Agents, Phytogenic / Q000096:biosynthesis*; D002455:Cell Division; D002478:Cells, Cultured; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D003517:Cyclopentanes / Q000737:chemistry / Q000378:metabolism*; D054883:Oxylipins; D017239:Paclitaxel / Q000096:biosynthesis*; D010946:Plants, Medicinal; D013237:Stereoisomerism; D043823:Taxoids; D020946:Taxus / Q000737:chemistry / Q000166:cytology / Q000378:metabolism*
D000085:Acetates; D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D003517:Cyclopentanes; D054883:Oxylipins; D043823:Taxoids; C073950:baccatin III; C072239:methyl jasmonate; D017239:Paclitaxel