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- Lindmark-Henriksson, Marica, et al.
(author)
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Transformation of alpha-pinene using Picea abies suspension culture
- 2003
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In: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 66:3, s. 337-343
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Journal article (peer-reviewed)abstract
- alpha-Pinene, both as the pure enantiomers and as the racemate, was transformed mainly to trans-verbenol by treatment with a Picea abies suspension cell culture. These reactions were followed by a slow transformation of the verbenol to verbenone, which was not transformed further. trans-Pinocarveol, myrtenol, cis-verbenol, and alpha-terpineol were byproducts of intermediate abundance. When subjected to the action of the suspension culture, cis-verbenol was not only transformed to verbenone but also isomerized to trans-verbenol. The transformation of alpha-pinene was fast, and the products were detected within one minute. The absolute configuration of the major products corresponded to that of the starting alpha-pinene enantiomer
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- Lindmark Henriksson, Marica, et al.
(author)
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Transformation of terpenes using a Picea abies suspension culture
- 2004
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In: Journal of Biotechnology. - : Elsevier BV. - 0168-1656 .- 1873-4863. ; 107:2, s. 173-184
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Journal article (peer-reviewed)abstract
- When subjected to a Picea abies suspension cell culture, beta-pinene, either one of the pure enantiomers or the racemate, was transformed mainly to trans-pinocarveol along with the minor products myrtenol, alpha-terpineol, pinocarvone, myrtenal and cis-pinocarveol. The absolute configuration of the major products corresponded to that of the starting beta-pinene enantiomer. Some of the primary transformation products, i.e. (1S)-cis- and (1S)-trans-pinocarveol, (1R)-myrtenol and (4S)-alpha-terpineol, were also tested as substrates of the P. abies suspension culture. They reacted more slowly than beta-pinene but, except for (4S)-alpha-terpineol, they were all transformed. Thus, (1R)-myrtenol was converted into both (1R)-myrtenal and (1R)-myrtanol, whereas (1S)-trans-pinocarveol was converted into (1S)-pinocarvone. (4R)-Limonene was slowly transformed by the suspension culture into limonene-(1,2)-epoxide as the major product, with carveol, perillyl alcohol and 1,8-cineole as minor products. Autoxidation of terpenes in cell-free nutrient medium was investigated in detail. alpha-Pinene and beta-pinene were both autoxidized to a certain extent, while limonene remained unaffected. The rate of the autoxidation was more than one order of magnitude slower than that of the biotransformation. Moreover, different products were formed by autoxidation than by biotransformation.
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