4th EucheMs chemistry congress

Poster Session 2
s1170
chem. Listy 106, s257–s1425 (2012)
Poster session 2 - food chemistry
P - 0 6 1 6
CheMiCAL StruCture And MeMBrAne
interACtivity reLAtionShiP of
nutrACeutiCAL fLAvonoidS in foodS And
BeverAGeS: their AntiProLiferAtive effeCtS
ASSoCiAted with the ChArACterized
reLAtionShiP
h. tSuChiyA 1
1 Asahi University School of Dentistry, Dental Basic Education,
Mizuho, Japan
introduction: Flavonoids are referred to as nutraceuticals
which provide plant-derived foods and beverages with disease
preventive and therapeutic potentials. However, beneficial effects
are significantly influenced by their chemical structures. Apart
from acting on proteinous target enzymes and receptors,
flavonoids also mechanistically interact with lipid bilayer
membranes. We characterized the structure and membrane
interactivity relationship of nutraceutical flavonoids, and verified
their antiproliferative effects associated with the relationship.
Methods: Biomimetic membranes were prepared with
phospholipids and cholesterol, and they were reacted with
32 structurally-relating flavonoids (flavones, flavonols,
flavanones, flavanonols, anthocyanidins, flavanols and
isoflavones) of 0.1–10 μM. The membrane interactivities of
flavonoids were compared using the potencies to modify
membrane fluidity by measuring fluorescence polarization with
different probes. Their antiproliferative effects were determined
by assaying the growth inhibition of mouse myeloma cells.
results: Flavonoids structure-dependently acted on the
deeper hydrophobic regions of lipid bilayers to decrease
membrane fluidity. The characterized relationship between
structure and membrane interactivity indicated that
3-hydroxylation of the C ring, a double bond between 2-carbon
and 3-carbon of the C ring, 3',4'-dihydroxylation of or no
substituents on the B ring, and 5,7-dihydroxylation of the A ring
are important for flavonoids to show greater membrane
interactions. As the basic structure, flavonoids were far preferable
to isoflavonoids. Aglycones were much more effective in
rigidifying biomimetic membranes than glycosides. Quercetin,
galangin, cyanidin and (–)-epigallocatechin gallate, meeting these
structural requirements, inhibited the growth of tumor cells at
10–100 μM. These antiproliferative flavonoids decreased the
fluidity of tumor cell membranes with the potency correlating to
the relative cell growth-inhibitory activity.
Conclusion: Membrane-interacting anti-tumor flavonoids
are contributable to the medical health benefits of plant-derived
foods and beverages. However, attention should be paid to the
possibility that nutraceutical flavonoids may exert adverse effects
by interacting with membrane-active drugs in the combination
therapy.
Keywords: Structure-activity relationships; Membranes;
Lipids; Natural products; Antiproliferation;
4 th EucheMs chemistry congress
P - 0 6 1 7
deterMinAtion of StiLBeneS And
2,4,6-trihydroxyPhenAnthrene-2-o-
-GLuCoSide in GrAPevine LeAveS infeCted
By PLASMoPArA vitiCoLA
n. vrChotovA 1 , J. triSKA 1 , J. oLeJniCKovA 2 ,
r. JiLeK 1 , d. SeBeLA 2 , r. SotoLAr 3
1 Global Change Research Centre AS CR v.v.i., Division on
Impact Studies and Physiological Analyses, Ceske Budejovice,
Czech Republic
2 Global Change Research Centre AS CR v.v.i., Division on
Impact Studies and Physiological Analyses, Nove Hrady,
Czech Republic
3 Mendel University in Brno, Faculty of Horticulture, Lednice,
Czech Republic
Plasmopara viticola stimulates the synthesis of stilbenes and
2,4,6-trihydroxyphenanthrene-2- O-glucoside in grapevine leaves
(Tríska et al. 2012), where 2,4,6-trihydroxyphenanthrene-2-O-
-glucoside arises from cis-piceid by cyclization. Infected leaves
of Pinot blanc, Pinot gris and Cabernet sauvignon were
lyophilized, grounded and than extracted with 70% methanol.
Extracts were analysed by reverse phase liquid chromatography
using Hewlett Packard instrument and columnn Phenomenex
Luna C18 (2) in gradient acetonitril-water-phosphoric acid.
Compounds were detected by DAD and FLD detectors (Agilent).
Phenanthrene derivative was confirmed also LC/MS
measurements. LC/MS were carried out using the Thermo Accela,
LCQ Fleet ion trap LC-MS instrument and APCI ionization
technique in the positive mode.
Values of trans-resveratrol were in ranges of 7-17mg/kg,
trans-pterostilbene 0.3-1 mg/kg, cis-piceid 54-108 mg/kg and
2,4,6-trihydroxyphenanthrene-2- O-glucoside 34-60 mg/kg.
Acknowledgements: This study was funded by the Grant
Agency of the Czech Republic, grant number 525/09/0365, and
by CzechGlobe - Centre for Global Climate Change Impacts
Studies, Reg. No. CZ.1.05/1.1.00/02.0073.
references:
1. Tríska J., Vrchotová N., Olejnícková J., Jílek R., Sotolár
R.: Separation and identification of highly fluorescent
compounds derived from trans-resveratrol in the leaves of
Vitis vinifera infected by Plasmopara viticola. Molecules
(2012) 17(3) 2773-2783.
Keywords: Phytochemistry; UV/Vis spectroscopy; Mass
spectroscopy; Biological activity;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc