Re-evaluation of the antioxidant prenylated flavonoids from the roots of Sophora flavescens.
The objective of this research was to re-evaluate the antioxidant effects of the prenylated flavonoids from Sophora flavescens via in vitro 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), peroxynitrite (ONOO(-)), and total reactive oxygen species (ROS) assays. In addition, a further examination of kuraridinol, kurarinol, and kurarinone, also isolated from S. flavescens, was carried out by the inhibition of tert-butylhydroperoxide (t-BHP)-induced intracellular ROS generation and t-BHP-induced activation of nuclear factor-kappaB (NF-kappaB). Upon re-examination of the ethyl acetate (EtOAc) soluble fraction of S. flavescens, two major prenylated chalcones, including kuraridin and kuraridinol, along with a minor prenylated flavonol, kushenol C, were isolated as good DPPH scavengers. This was in contrast to the prenylated flavanones, sophoraflavanone G and kurarinone, which were isolated from the methylene chloride (CH(2)Cl(2)) fraction of the same source. Five flavanones consisting of kushenol E, leachianone G, kurarinol, sophoraflavanone G, and kurarinone exhibited significant antioxidant potentials in the ABTS, ONOO(-), and total ROS assays; however, the prenylated chalcones and prenylated flavonol showed more potent scavenging/inhibitory activities than the prenylated flavanones. Therefore, the prenylated chalcones and prenylated flavonol, rather than the prenylated flavanones, may make important contributions toward the marked antioxidant capacities of S. flavescens. Furthermore, kuraridinol, kurarinol, and kurarinone showed significant inhibitory activities against intracellular ROS levels as well as NF-kappaB activation by t-BHP. Overall, the results indicate that S. flavescens and its prenylated flavonoids may possess good anti-inflammatory activity, which is implicated in their significant antioxidant activity.
Jung
Hyun Ah
HA
Division of Food Science and Biotechnology, Pukyong National University, .Busan 608-737, Korea.
Jeong
Da-Mi
DM
Chung
Hae Young
HY
Lim
Hyun Ae
HA
Kim
Ji Young
JY
Yoon
Na Young
NY
Choi
Jae Sue
JS
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000494:pharmacology; D000975:Antioxidants / Q000494:pharmacology*; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002460:Cell Line; D002839:Chromans / Q000737:chemistry; D005419:Flavonoids / Q000494:pharmacology*; D017930:Genes, Reporter / Q000187:drug effects; D006801:Humans; D008156:Luciferases / Q000096:biosynthesis / Q000235:genetics; D009682:Magnetic Resonance Spectroscopy; D016328:NF-kappa B / Q000378:metabolism; D030421:Peroxynitrous Acid / Q000378:metabolism; D010851:Picrates / Q000494:pharmacology; D010936:Plant Extracts / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D054876:Prenylation; D051381:Rats; D017382:Reactive Oxygen Species / Q000378:metabolism; D029909:Sophora / Q000737:chemistry*; D013451:Sulfonic Acids / Q000378:metabolism; D013844:Thiazoles / Q000378:metabolism; D020122:tert-Butylhydroperoxide / Q000494:pharmacology
D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D002839:Chromans; D005419:Flavonoids; D016328:NF-kappa B; D010851:Picrates; D010936:Plant Extracts; D017382:Reactive Oxygen Species; D013451:Sulfonic Acids; D013844:Thiazoles; D030421:Peroxynitrous Acid; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D020122:tert-Butylhydroperoxide; C004931:1,1-diphenyl-2-picrylhydrazyl; D008156:Luciferases; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid