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 -