| 11. |
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| 12. |
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| 13. |
- Lindmark-Henriksson, Marica, et al.
(författare)
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Transformation of alpha-pinene using Picea abies suspension culture
- 2003
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 66:3, s. 337-343
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Tidskriftsartikel (refereegranskat)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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| 14. |
- Lindmark Henriksson, Marica, et al.
(författare)
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Transformation of terpenes using a Picea abies suspension culture
- 2004
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Ingår i: Journal of Biotechnology. - : Elsevier BV. - 0168-1656 .- 1873-4863. ; 107:2, s. 173-184
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Tidskriftsartikel (refereegranskat)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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| 15. |
- Schlyter, F, et al.
(författare)
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Carvone and less volatile analogues as repellent and deterrent antifeedants against the pine weevil, Hylobius abietis
- 2004
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Ingår i: Journal of applied entomology. - : Wiley. - 0931-2048 .- 1439-0418. ; 128:9-10, s. 610-619
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Tidskriftsartikel (refereegranskat)abstract
- The monoterpenoid carvone (1) has been shown to have strong antifeedant effects on Hylobius spp. However, because of the high volatility of carvone, long-time protection of conifer seedlings in the field using this compound has not been possible. We demonstrate, in several bioassay steps, that less-volatile, heavier analogues retain their pre-ingestive feeding inhibition activity in the large pine weevil, Hylobius abietis (L.) for a longer time. The first step in the evaluation of the biological activity of 12 carvone analogues was a micro-assay, a choice test lasting 4 h. Compounds active at 100 nmol/cm(2) were further dose-response tested to give the effective dose needed to inhibit feeding by 50% (ED50). Of the 14 compounds tested, including both carvone enantiomers, seven heavier analogues were active at low doses (had low ED50 values). As expected from their lower vapour pressure compared with carvone, the heavier analogues proved more resistant to evaporation before testing. Thus, whereas the effect of 8-hydroxy-p-menth-en-6-one 4 declined after 2 days, some of the compounds with high molar masses, such as the alkylhydroxymenthenones 6 and 8, retained a stable activity for 4 days. The retained activity at 4 days was strongly correlated to molecular mass and boiling point. When tested on natural material (host Pinus sylvestris L. twig sections for 48 h), the heavier analogues showed a rather low activity. Probably, the activity of the more volatile compound carvone (1) is due to a repellent effect (olfactory mode) rather than the deterrent effects (gustatory mode) of the heavier compounds. In agreement with the relatively low activity on twigs in the laboratory, the hydroxymenthenone 4 was not active in the field when tested for 2 months as a 1 : 9 mixture with a polar wax.
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