Details
| Original language | English |
|---|---|
| Pages (from-to) | 194-199 |
| Number of pages | 6 |
| Journal | Phytochemistry |
| Volume | 157 |
| Early online date | 12 Nov 2018 |
| Publication status | Published - Jan 2019 |
Abstract
Inspired by the recently discovered phenomenon of “horizontal natural product transfer” we investigated the putative uptake of phenolic specialized metabolites. Umbelliferone was chosen for this case study, since this coumarin as well as its derivatives can easily be determined by HPLC analyses. Barley (Hordeum vulgare L.), radish (Raphanus sativus L.), pea (Pisum sativum L.), flax (Linum usitatissimum L.), and garden cress (Lepidium sativum L.) were cultivated in hydroponic media, to which the coumarin was applied. Uptake of umbelliferone was verified by corresponding HPLC analyses of extracts obtained from the aerial parts of the seedlings. In all cases, a tremendous uptake of umbelliferone was observed. In plants that genuinely contain coumarins, the umbelliferone taken up was modified: in garden cress, it was hydroxylated and glucosylated to yield esculin, while in barley seedlings, the imported umbelliferone was modified by methoxylation to yield scopoletin. Corresponding reactions are known from modifications of xenobiotics to be catalyzed by cytochrome P450 enzymes. Accordingly, in an additional approach, umbelliferone was applied together with naproxen, which is reported to reduce enzyme activity of P450 enzymes. As predicted, the conversion of umbelliferone to scopoletin in barley as well as the modification to esculin in garden cress was strongly reduced by the addition of naproxen. These data for the first time demonstrate that – in addition to alkaloids – also phenolic compounds are taken up by various acceptor plants. Apart from the leaching of rotting plants, coumarins are known to be exuded by many plants. Accordingly, these compounds are frequently present in soils and will be taken up. These coherences imply that the horizontal natural product transfer might represent a more general phenomenon in plant ecology. Moreover, this study outlines that – in analogy to the modification of xenobiotics – also natural products taken up are modified in the acceptor plants.
Keywords
- Biotransformation, Coumarins, Esculin, Glucosylation, Hordeum vulgare L., Horizontal transfer, Hydroxylation, Lepidium sativum L., Linum usitatissimum L., Pisum sativum L., Raphanus sativus L., Scopoletin, Umbelliferone
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Biology
- Agricultural and Biological Sciences(all)
- Plant Science
- Agricultural and Biological Sciences(all)
- Horticulture
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In: Phytochemistry, Vol. 157, 01.2019, p. 194-199.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Uptake and modification of umbelliferone by various seedlings
AU - Hijazin, Tahani
AU - Radwan, Alzahraa
AU - Abouzeid, Sara
AU - Dräger, Gerald
AU - Selmar, Dirk
N1 - Funding information: The fellowship of Tahani Hijazin provided by the Mutah University (Jordan) is greatly acknowledged. The authors thank Dr. Hans-Peter Mock (IPK Gatersleben, Germany) for the provision of the barley seeds of the variety SL 101.
PY - 2019/1
Y1 - 2019/1
N2 - Inspired by the recently discovered phenomenon of “horizontal natural product transfer” we investigated the putative uptake of phenolic specialized metabolites. Umbelliferone was chosen for this case study, since this coumarin as well as its derivatives can easily be determined by HPLC analyses. Barley (Hordeum vulgare L.), radish (Raphanus sativus L.), pea (Pisum sativum L.), flax (Linum usitatissimum L.), and garden cress (Lepidium sativum L.) were cultivated in hydroponic media, to which the coumarin was applied. Uptake of umbelliferone was verified by corresponding HPLC analyses of extracts obtained from the aerial parts of the seedlings. In all cases, a tremendous uptake of umbelliferone was observed. In plants that genuinely contain coumarins, the umbelliferone taken up was modified: in garden cress, it was hydroxylated and glucosylated to yield esculin, while in barley seedlings, the imported umbelliferone was modified by methoxylation to yield scopoletin. Corresponding reactions are known from modifications of xenobiotics to be catalyzed by cytochrome P450 enzymes. Accordingly, in an additional approach, umbelliferone was applied together with naproxen, which is reported to reduce enzyme activity of P450 enzymes. As predicted, the conversion of umbelliferone to scopoletin in barley as well as the modification to esculin in garden cress was strongly reduced by the addition of naproxen. These data for the first time demonstrate that – in addition to alkaloids – also phenolic compounds are taken up by various acceptor plants. Apart from the leaching of rotting plants, coumarins are known to be exuded by many plants. Accordingly, these compounds are frequently present in soils and will be taken up. These coherences imply that the horizontal natural product transfer might represent a more general phenomenon in plant ecology. Moreover, this study outlines that – in analogy to the modification of xenobiotics – also natural products taken up are modified in the acceptor plants.
AB - Inspired by the recently discovered phenomenon of “horizontal natural product transfer” we investigated the putative uptake of phenolic specialized metabolites. Umbelliferone was chosen for this case study, since this coumarin as well as its derivatives can easily be determined by HPLC analyses. Barley (Hordeum vulgare L.), radish (Raphanus sativus L.), pea (Pisum sativum L.), flax (Linum usitatissimum L.), and garden cress (Lepidium sativum L.) were cultivated in hydroponic media, to which the coumarin was applied. Uptake of umbelliferone was verified by corresponding HPLC analyses of extracts obtained from the aerial parts of the seedlings. In all cases, a tremendous uptake of umbelliferone was observed. In plants that genuinely contain coumarins, the umbelliferone taken up was modified: in garden cress, it was hydroxylated and glucosylated to yield esculin, while in barley seedlings, the imported umbelliferone was modified by methoxylation to yield scopoletin. Corresponding reactions are known from modifications of xenobiotics to be catalyzed by cytochrome P450 enzymes. Accordingly, in an additional approach, umbelliferone was applied together with naproxen, which is reported to reduce enzyme activity of P450 enzymes. As predicted, the conversion of umbelliferone to scopoletin in barley as well as the modification to esculin in garden cress was strongly reduced by the addition of naproxen. These data for the first time demonstrate that – in addition to alkaloids – also phenolic compounds are taken up by various acceptor plants. Apart from the leaching of rotting plants, coumarins are known to be exuded by many plants. Accordingly, these compounds are frequently present in soils and will be taken up. These coherences imply that the horizontal natural product transfer might represent a more general phenomenon in plant ecology. Moreover, this study outlines that – in analogy to the modification of xenobiotics – also natural products taken up are modified in the acceptor plants.
KW - Biotransformation
KW - Coumarins
KW - Esculin
KW - Glucosylation
KW - Hordeum vulgare L.
KW - Horizontal transfer
KW - Hydroxylation
KW - Lepidium sativum L.
KW - Linum usitatissimum L.
KW - Pisum sativum L.
KW - Raphanus sativus L.
KW - Scopoletin
KW - Umbelliferone
UR - http://www.scopus.com/inward/record.url?scp=85057167007&partnerID=8YFLogxK
U2 - 10.1016/j.phytochem.2018.10.032
DO - 10.1016/j.phytochem.2018.10.032
M3 - Article
C2 - 30439620
AN - SCOPUS:85057167007
VL - 157
SP - 194
EP - 199
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
ER -