The production of taxuyunnanine C (Tc) (2α,5α,10β,14β-tetraacetoxytaxa-4(20),11(12)-diene) was significantly enhanced when Taxus chinensis cell cultures were treated with methyl jasmonate (MJA) or 2,3-dihydroxypropyl jasmonate (DHPJA), a newly synthesized jasmonate analog, in combination with in situabsorption. Along with the production of Tc, two intermediate taxoids were produced and purified. On the basis of liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectral data, the chemical structures of the two intermediate taxoids were found to be 2-hydroxy-5α,10β-diacetoxytaxadiene and 2-hydroxy-5α,10β,14β-triacetoxytaxadiene. This is the first study to report the production of these two taxoids using plant cell culture.
Key words: Taxus chinensis, taxuyunnanine C, methyl jasmonate, 2,3-dihydroxypropyl jasmonate, in situ absorption, 2-hydroxy-5α,10β-diacetoxytaxadiene, 2-hydroxy-5α,10β,14β-triacetoxytaxadiene.
Abbreviations: Tc, Taxuyunnanine C; MJA, methyl jasmonate; DHPJA, 2,3-dihydroxypropyl jasmonate; LC-MS, liquid chromatography-mass spectrometry;NMR, nuclear magnetic resonance; GGPP, geranylgeranyl diphosphate; IPP,isoprenyl diphosphate; DAPP, dimethylallyl diphosphate; GGPPS, geranylgeranyl pyrophosphate synthase; TASY, taxadiene synthase; T5αH, taxadiene 5α-hydroxylase; HPLC, high performance liquid chromatography; HR-ESI-MS, high resolution electrospray ionization mass spectra; 6-BA, 6-benzyladenine; Vc,ascorbic acid; NAA, naphthaleneacetic acid; 2,4-D, 2,4-dichlorophenoxy-acetic acid; PVDF, polyvinylidenedifluoride; TLC, thin layer chromatography; TDAT,taxadiene acetyltransferase.
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