Influence of the Active Compounds of Perilla frutescens Leaves on Lipid Membranes
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Influence of the Active Compounds of Perilla frutescens Leaves on Lipid Membranes. / Duelund, Lars; Amiot, Arnaud; Fillon, Alexandra; Mouritsen, Ole G.
In: Journal of Natural Products, Vol. 75, No. 2, 2012, p. 160-166.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Influence of the Active Compounds of Perilla frutescens Leaves on Lipid Membranes
AU - Duelund, Lars
AU - Amiot, Arnaud
AU - Fillon, Alexandra
AU - Mouritsen, Ole G.
PY - 2012
Y1 - 2012
N2 - The leaves of the annual plant Perilla frutescens are used widely as a spice and a preservative in Asian food as well as in traditional medicine. The active compounds in the leaves are the cyclic monoterpene limonene (1) and its bio-oxidation products, perillaldehyde (2), perillyl alcohol (3), and perillic acid (4). These compounds are known to be biologically active and exhibit antimicrobial, anticancer, and anti-inflammatory effects that could all be membrane mediated. In order to assess the possible biophysical effects of these compounds on membranes quantitatively, the influence of limonene and its bio-oxidation products has been investigated on a membrane model composed of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) using differential scanning calorimetry (DSC), isothermal titration calorimetry (ITC), and electron paramagnetic resonance spectroscopy (EPR). It was found that limonene (1), perillyl alcohol (2), and perillaldehyde (3) partitioned into the DMPC membrane, whereas perillic acid (4) did not. The DSC results demonstrated that all the partitioning compounds strongly perturbed the phase transition of DMPC, whereas no perturbation of the local membrane order was detected by EPR spectroscopy. The results of the study showed that limonene (1) and its bio-oxidation products affect membranes in rather subtle ways.
AB - The leaves of the annual plant Perilla frutescens are used widely as a spice and a preservative in Asian food as well as in traditional medicine. The active compounds in the leaves are the cyclic monoterpene limonene (1) and its bio-oxidation products, perillaldehyde (2), perillyl alcohol (3), and perillic acid (4). These compounds are known to be biologically active and exhibit antimicrobial, anticancer, and anti-inflammatory effects that could all be membrane mediated. In order to assess the possible biophysical effects of these compounds on membranes quantitatively, the influence of limonene and its bio-oxidation products has been investigated on a membrane model composed of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) using differential scanning calorimetry (DSC), isothermal titration calorimetry (ITC), and electron paramagnetic resonance spectroscopy (EPR). It was found that limonene (1), perillyl alcohol (2), and perillaldehyde (3) partitioned into the DMPC membrane, whereas perillic acid (4) did not. The DSC results demonstrated that all the partitioning compounds strongly perturbed the phase transition of DMPC, whereas no perturbation of the local membrane order was detected by EPR spectroscopy. The results of the study showed that limonene (1) and its bio-oxidation products affect membranes in rather subtle ways.
U2 - 10.1021/np200713q
DO - 10.1021/np200713q
M3 - Journal article
C2 - 22272932
AN - SCOPUS:84857600571
VL - 75
SP - 160
EP - 166
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 2
ER -
ID: 230975309