Antiradical and antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects

Bioorganic & Medicinal Chemistry
Lucia RackováMilan Stefek

Abstract

The antioxidant activities of three alkaloids isolated from Mahonia aquifolium--berberine, jatrorrhizine, and magnoflorine--were studied with respect to their structural aspects, particularly the presence and the position of -OH groups, steric conditions of unpaired electron delocalization and parameters of lipophilicity and hydration energy. The antiradical activities of the compounds tested were evaluated as the reactivities toward free stable alpha,alpha'-diphenyl-beta-picrylhydrazyl radical (DPPH). The antioxidant features of the alkaloids tested were investigated in heterogeneous membrane system of DOPC liposomes stressed by peroxidative damage induced by AAPH azoinitiator. Both alkaloids bearing free phenolic groups--jatrorrhizine and magnoflorine--showed better activities in both systems used than berberine not bearing any readily abstractable hydrogen on its skeleton. The former two showed antiperoxidative efficiency in DOPC liposomal membrane comparable to that of an effective scavenger of peroxyl radicals--stobadine-and higher than that of Trolox. We conclude that the favorable antioxidant features of the hydroxylated alkaloids are most probably ensured by the combination of reasonably high antiradical reactivity with...Continue Reading

References

Jan 1, 1992·Free Radical Biology & Medicine·L A MartínezM J Alcaraz
Feb 1, 1980·Journal of Medicinal Chemistry·G L BiagiP A Borea
Dec 1, 1996·Chemical Research in Toxicology·S A van AckerA Bast
Jan 1, 1997·Free Radical Biology & Medicine·J AntosiewiczL Greci
Jan 23, 1999·Free Radical Biology & Medicine·E J LienR Wang
Jun 15, 2000·Bioorganic & Medicinal Chemistry Letters·G DoreyP Casara
Jul 28, 2001·Journal of Natural Products·K IwasaW Wiegrebe
Aug 15, 2001·Folia Microbiologica·A VollekováR Sochorová
Nov 20, 2001·Chemical Research in Toxicology·J J InbarajC F Chignell
Apr 12, 2002·BMC Complementary and Alternative Medicine·Marta CernákováJán Drímal

❮ Previous
Next ❯

Citations

Oct 21, 2006·Analytical and Bioanalytical Chemistry·Renáta OvádekováJán Labuda
Nov 22, 2008·Archives of Pharmacal Research·Hyun Ah JungJae Sue Choi
Feb 3, 2009·Archives of Pharmacal Research·Jia-Hui ChenYong-Ping Yang
May 12, 2009·Journal of Asian Natural Products Research·Li-Jun WangXiao-Hua Niu
Aug 5, 2009·Biological & Pharmaceutical Bulletin·Hyun Ah JungJae Sue Choi
Feb 1, 2013·International Journal of Molecular Sciences·Jung ChaoHao-Yuan Cheng
Jan 1, 2014·International Journal of Food Science·Probir Kumar GhoshMousumi Poddar-Sarkar
Jun 1, 2011·Fitoterapia·Waranya ChatuphonprasertKanokwan Jarukamjorn
May 22, 2010·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Sriram Gopi, Oruganti H Setty
Feb 16, 2010·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·F-R ZhaoX-M Gao
Jul 7, 2009·Journal of Ethnopharmacology·Jung ChaoWen-Huang Peng
Aug 6, 2013·The British Journal of Dermatology·S DengC C L Xue
Feb 9, 2012·The Journal of Pharmacy and Pharmacology·Beibei ZhangDazheng Wu
Jun 6, 2009·Chemico-biological Interactions·Bing-Sang WongYih-Shou Hsieh
Aug 15, 2006·Journal of Photochemistry and Photobiology. B, Biology·Sona JantováJuraj Lábaj
Aug 30, 2005·Clinica Chimica Acta; International Journal of Clinical Chemistry·Martin KopániCsaba Biró
Nov 1, 2005·Environmental Toxicology and Pharmacology·K G Nevin, P L Vijayammal
Oct 29, 2015·Evidence-based Complementary and Alternative Medicine : ECAM·Bing PangXiao-Lin Tong
Jul 30, 2015·Neurochemistry International·Yu Pong NgNancy Y Ip
Jun 30, 2006·Redox Report : Communications in Free Radical Research·Viera JancinováDagmar Holománová
May 27, 2015·Indian Journal of Pharmaceutical Sciences·Z C LiS Z Zhao
Dec 26, 2012·Food Chemistry·Wirginia Kukula-KochEleftherios Kalpoutzakis
Apr 29, 2014·Journal of Ethnopharmacology·Camille DesgrouasEvelyne Ollivier
Dec 24, 2014·Pathology, Research and Practice·Eva KralovaTatiana Stankovicova
Apr 26, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rosaliana LibroEmanuela Mazzon
Mar 16, 2017·Drug Metabolism Reviews·Kun WangFeng Qiu

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.