White, John Joseph; (1993) Studies on the secondary metabolism of some plant tissue cultures. Doctoral thesis (Ph.D), UCL (University College London).

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Abstract

In the first part of this work, tissue cultures of the herb Galium verum were established under a variety of light and hormone regimes. Cultures flourished under all regimes attempted. All culture lines produced pigments, with an inverse relationship between growth and pigment production being readily apparent. The acid-hydrolysed extracts of these cultures were examined by high performance liquid chromatography using an ultra-violet (diode-array) detector over the wavelength range 190-370nm. This detected over 80 different compounds, mostly of the same class. Comparison between these extracts with those similarly prepared from roots and flowers of the parent plant indicated a number of compounds to be present in both roots and cultures. Ten compounds were isolated from the acid-hydrolysed extracts of the cultures. Eight of these were characterised by mass spectrometry and NMR spectroscopy as anthraquinone pigments, some of these being unreported in the literature. In a concurrent study the metabolism of monoterpenoid epoxides in plants and cultures was investigated. 14C-labelled limonene-1,2-epoxide was synthesised in four steps from A-acetyl-l-methylcyclohex-l-ene. Following purification, this compound was fed to both the plant and to especially established tissue cultures of Pelargonium fragrans. In these preliminary studies very poor incorporations were noted and neither of the hoped-for products, namely, 14C-borneol and 14C-camphor were detected. Thus no evidence was obtained for epoxides as biosynthetic intermediates leading to cyclic monoterpenoids in either higher plants or their tissue cultures. The synthesis of 14C-linalool-6,7-epoxide, from 7-methyl-l,6- octadien-3-one was also attempted, although problems with the epoxidation of linalool could not be fully resolved. A synthetic route to the two furan isomers of 6,7-epoxylinalool was also developed.

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