Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation.
Steroidal glycoalkaloids (SGA) are toxic secondary metabolites naturally occurring in the potato, as well as in certain other Solanaceous plant species, such as tomato, eggplant and pepper. To investigate the steroidal origin of SGA biosynthesis, cut potato shoots were fed cholesterol labelled with...
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| Format: | Article |
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Public Library of Science (PLoS)
2013-01-01
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| Series: | PLoS ONE |
| Online Access: | http://europepmc.org/articles/PMC3857313?pdf=render |
| _version_ | 1818286553176211456 |
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| author | Erik V Petersson Nurun Nahar Paul Dahlin Anders Broberg Rikard Tröger Paresh C Dutta Lisbeth Jonsson Folke Sitbon |
| author_facet | Erik V Petersson Nurun Nahar Paul Dahlin Anders Broberg Rikard Tröger Paresh C Dutta Lisbeth Jonsson Folke Sitbon |
| author_sort | Erik V Petersson |
| collection | DOAJ |
| description | Steroidal glycoalkaloids (SGA) are toxic secondary metabolites naturally occurring in the potato, as well as in certain other Solanaceous plant species, such as tomato, eggplant and pepper. To investigate the steroidal origin of SGA biosynthesis, cut potato shoots were fed cholesterol labelled with deuterium (D) in the sterol ring structure (D5- or D6-labelled), or side chain (D7-labelled), and analysed after three or five weeks. The labelled cholesterol and presence of D-labelled SGA were analysed by GC-MS and LC-MS/MS, respectively. When feeding D-labelled cholesterol solubilised in Tween-80, labelled cholesterol in free form became present in both leaves and stems, although the major part was recovered as steryl esters. Minor amounts of D-labelled SGA (α-solanine and α-chaconine) were identified in cholesterol-treated shoots, but not in blank controls, or in shoots fed D6-27-hydroxycholesterol. Solubilising the labelled cholesterol in methyl-β-cyclodextrin instead of Tween-80 increased the levels of labelled SGA up to 100-fold, and about 1 mole% of the labelled cholesterol was recovered as labelled SGA in potato leaves. Both side chain and ring structure D labels were retained in SGA, showing that the entire cholesterol molecule is converted to SGA. However, feeding side chain D7-labelled cholesterol resulted in D5-labelled SGA, indicating that two hydrogen atoms were released during formation of the SGA nitrogen-containing ring system. Feeding with D7-sitosterol did not produce any labelled SGA, indicating that cholesterol is a specific SGA precursor. In conclusion, we have demonstrated a superior performance of methyl-β-cyclodextrin for delivery of cholesterol in plant tissue feeding experiments, and given firm evidence for cholesterol as a specific sterol precursor of SGA in potato. |
| first_indexed | 2024-12-13T01:26:25Z |
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| id | doaj.art-7e746b306aab489dadd007f221126d40 |
| institution | Directory Open Access Journal |
| issn | 1932-6203 |
| language | English |
| last_indexed | 2024-12-13T01:26:25Z |
| publishDate | 2013-01-01 |
| publisher | Public Library of Science (PLoS) |
| record_format | Article |
| series | PLoS ONE |
| spelling | doaj.art-7e746b306aab489dadd007f221126d402022-12-22T00:04:07ZengPublic Library of Science (PLoS)PLoS ONE1932-62032013-01-01812e8295510.1371/journal.pone.0082955Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation.Erik V PeterssonNurun NaharPaul DahlinAnders BrobergRikard TrögerParesh C DuttaLisbeth JonssonFolke SitbonSteroidal glycoalkaloids (SGA) are toxic secondary metabolites naturally occurring in the potato, as well as in certain other Solanaceous plant species, such as tomato, eggplant and pepper. To investigate the steroidal origin of SGA biosynthesis, cut potato shoots were fed cholesterol labelled with deuterium (D) in the sterol ring structure (D5- or D6-labelled), or side chain (D7-labelled), and analysed after three or five weeks. The labelled cholesterol and presence of D-labelled SGA were analysed by GC-MS and LC-MS/MS, respectively. When feeding D-labelled cholesterol solubilised in Tween-80, labelled cholesterol in free form became present in both leaves and stems, although the major part was recovered as steryl esters. Minor amounts of D-labelled SGA (α-solanine and α-chaconine) were identified in cholesterol-treated shoots, but not in blank controls, or in shoots fed D6-27-hydroxycholesterol. Solubilising the labelled cholesterol in methyl-β-cyclodextrin instead of Tween-80 increased the levels of labelled SGA up to 100-fold, and about 1 mole% of the labelled cholesterol was recovered as labelled SGA in potato leaves. Both side chain and ring structure D labels were retained in SGA, showing that the entire cholesterol molecule is converted to SGA. However, feeding side chain D7-labelled cholesterol resulted in D5-labelled SGA, indicating that two hydrogen atoms were released during formation of the SGA nitrogen-containing ring system. Feeding with D7-sitosterol did not produce any labelled SGA, indicating that cholesterol is a specific SGA precursor. In conclusion, we have demonstrated a superior performance of methyl-β-cyclodextrin for delivery of cholesterol in plant tissue feeding experiments, and given firm evidence for cholesterol as a specific sterol precursor of SGA in potato.http://europepmc.org/articles/PMC3857313?pdf=render |
| spellingShingle | Erik V Petersson Nurun Nahar Paul Dahlin Anders Broberg Rikard Tröger Paresh C Dutta Lisbeth Jonsson Folke Sitbon Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation. PLoS ONE |
| title | Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation. |
| title_full | Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation. |
| title_fullStr | Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation. |
| title_full_unstemmed | Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation. |
| title_short | Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation. |
| title_sort | conversion of exogenous cholesterol into glycoalkaloids in potato shoots using two methods for sterol solubilisation |
| url | http://europepmc.org/articles/PMC3857313?pdf=render |
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