Abstract:
:We investigated the antioxidant and radical scavenging activity of polyphenolic isochromans. To assess the relation between structure and scavenging properties the natural occurring 1-(3'-methoxy-4'-hydroxy)phenyl-6,7-dihydroxy-isochroman (ISO-3, three OH groups) was compared with three newly synthesized derivatives that differ in their degree of hydroxylation by substitution with methoxy-groups (ISO-4: four OH groups; ISO-2: two OH groups and ISO-0: fully methoxylated). We found that ISO-4 is a 2-fold better scavenger for the artificial radical 1,1-diphenyl-2-picrylhydrazyl (DPPH, 100 microM) with an EC50=10.3 microM compared to the natural ISO-3 (EC50=22.4 microM) and to ISO-2 (EC50=25.1 microM), while ISO-0 did not react with DPPH. The scavenging capacity for superoxide enzymatically generated in a hypoxanthin-xanthinoxidase reaction was the highest for ISO-4 (EC50=34.3 microM) compared to those of ISO-3 (EC50=84.0 microM) and ISO-2 (EC50=91.8 microM), while ISO-0 was inactive. In analogy, ISO-4 scavenged peroxynitrite (ONOO-, EC25=23.0 microM) more effective than ISO-3, ISO-2 and ISO-0. When C6 rat glioma cells loaded with the reactive oxygen/nitrogen (ROS/RNS)-sensitive fluorochrome 2,7-dichlorodihydrofluorescein, were exposed to hydrogen peroxide, the lowest stress level as indicated by the fluorescence signal was detected when the cells were pretreated with ISO-4 or ISO-2 but to a much lesser extent with ISO-3, while ISO-0 did not show any effect. All tested hydroxyisochromans superceded the scavenging effect of trolox.The excellent radical and ROS/RNS scavenging features of the hydroxy-1-aryl isochromans and their simple synthesis let these compounds appear to be interesting candidates for pharmaceutical interventions that protect against the deleterious action of ROS/RNS.
journal_name
Free Radic Resjournal_title
Free radical researchauthors
Lorenz P,Zeh M,Martens-Lobenhoffer J,Schmidt H,Wolf G,Horn TFdoi
10.1080/10715760500073733keywords:
subject
Has Abstractpub_date
2005-05-01 00:00:00pages
535-45issue
5eissn
1071-5762issn
1029-2470pii
M651L075605527GHjournal_volume
39pub_type
杂志文章abstract::Rabbits were fed a diet containing 1% cholesterol for 8 weeks and the levels of iron and oxidized lipids in liver analysed using atomic absorption spectroscopy and gas chromatography-mass spectrometry. A non-significant trend to an increase in iron level, but significant increases in the lipid peroxidation products, F...
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