Antioxidant Activities of Polyphenols Extracted from Perilla frutescens Varieties

Meng, Linghua; Lozano, Yves; Gaydou, Émile M.; Li, Bin

doi:10.3390/molecules14010133

Cited by 122 publications

(87 citation statements)

References 16 publications

(26 reference statements)

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“…The presence of a catecholic moiety seems to be of great importance to the antioxidant activity of HCAs [101,103,[116][117][118][119]. In this regard, two critical factors have been pro-posed emphasizing the antiradical activity of HCAs contain-ing catechol moiety bond dissociation energy of O-H bond and ionization potential [52].…”

Section: Position Of Hydroxy Groupsmentioning

confidence: 99%

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

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Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxi-dant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the car-boxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activ-ity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimiza-tion of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be use-ful for management of oxidative stress-related diseases.Keywords: Antioxidant, hydroxycinnamic acids, in vitro, ROS, structure-activity relationships. OXIDATIVE STRESS AND ANTIOXIDANTSReactive oxygen species (ROS) are oxygen derived molecules that readily react with other compounds and macromolecules and oxidize them. Some representative exam-ples of these species include superoxide (O2•-), hydroxy (HO • ) and peroxy (ROO • ) radicals, hydrogen peroxide (H2O2) and singletROS are involved in important physiological processes such as immune response, gene expression, signal transduc-tion and growth regulation [5,6]; however if they are not kept under tight control by physiological antioxidant systems they will be able to oxidize and damage various biological molecules leading to a condition called oxidative stress [1,7,8]. In this regard, oxidative stress has been reported to be in-volved in the pathogenesis of diseases such as cancer [9], neurodegenerative diseases [10], stroke [11], and others [12,13].Since an important source of ROS comes from environment [14], with the industrial development and the change in life style, oxidative stress related diseases need a special attention [15].Antioxidants operate by preventing or slowing the progression of oxidative damage reactions [16,17]. An antioxidant has been defined as "any substance that delays, p...

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Section: Position Of Hydroxy Groupsmentioning

confidence: 99%

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

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“…Previous investigations have discovered that some polyphenols extracted from P. frutescens exhibit pharmacological activities such as anti-allergy, anti-inflammatory [1] and anti-oxidant [2]. Among these components, luteolin and apigenin, the common flavones which are contained in a wide range of beneficial or dietary plants including weld (Reseda luteola L.), carrot (Daucus carota subsp.…”

Section: Introductionmentioning

confidence: 99%

“…Generally substances were prepared with organic solvents such as ethanol, methanol, acetone and toluene. Whereas some researchers developed and applied sophisticated methods [2], simple maceration at a range of temperatures is broadly accepted and common practice [1,3]. Recently, supercritical carbon dioxide (SC-CO 2 ) extraction has provoked considerable interest as a separation technique in many fields [5][6][7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Extraction of Luteolin and Apigenin from Leaves of <i>Perilla frutescens</i> (L.) Britt. with Liquid Carbon Dioxide

Mishima

Kawakami

Yokota

et al. 2014

SERDJ

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The extraction of luteolin and apigenin from the leaves of Perilla frutescens (L.) Britt. by liquid carbon dioxide (CO 2 ) was carried out at 5, 20 and 25 ºC. The extraction pressure was from 8.5 to 14 MPa. The extraction yields were compared with yields obtained by other solvent extraction methods, such as supercritical CO 2 extraction and conventional aqueous alcohol extraction. We conducted qualitative and quantitative analyses for luteolin and apigenin in the extract by HPLC and analyzed the extraction behavior.The effect of two operating parameters, temperature and pressure of liquid CO 2 , on the extraction yield was investigated using the single-factor method. The yields of luteolin and apigenin in the extraction were significantly improved by the operating temperature, whereas a change in the selectivity of the extract was not observed.

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“…5C). 임자엽에는 루테올린 이외 플라본 유도체(flavone derivatives) 로 apigenin, scutellarein, 신남산 유도체(cinamic acid derivatives)로 rosmarinic acid, caffeic acid, 그 밖에 안 토시아닌(anthocyanins)을 활성성분으로 함유하고 있으며, 상대적인 함량은 rosmarinic acid, 루테올린, caffeic acid, apigenin 순서이다 27,28) . 루테올린의 경우 rosmarinic acid 보다 임자엽에 다소 낮게 함유되어 있지만, 베타아밀로이드를 생성하는 효소 β -secratase (BACE1)의 억제 활성에 있어 rosmarinic acid (21 µM)보다 저용량(0.5 µM)에서 효능을 나타내었으며 29) , in vivo 동물실험에서 다른 활성성분과 비교 하여 탁월한 항염 효능을 나타내었다 6) .…”

Section: ) 세포배양unclassified

Protective Effect of Luteolin against β-Amyloid-induced Cell Death and Damage in BV-2 Microglial Cells

Park

Jang

2013

The Korea Journal of Herbology

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Objectives : The purpose of this study is to investigate neuroprotective effects and molecular mechanisms of luteolin against β -amyloid (Aβ 25-35)-induced oxidative cell death in BV-2 cells. Methods : The protective effects of luteolin against Aβ25-35-induced cytotoxicity and apoptotic cell death were determined by MTT dye reduction assay and TUNEL staining, respectively. The apoptotic cell death was further analyzed by measuring mitochondrial transmembrane potential and expression of pro-and/or anti-apoptotic proteins. To elucidate the molecular mechanisms underlying the protective effects of luteolin, intracellular accumulation of reactive oxygen species, oxidative damages, and expression of antioxidant enzymes were examined. Results : Luteolin pretreatment effectively attenuated Aβ 25-35-induced apoptotic cell death indices such as DNA fragmentation, dissipation of mitochondrial transmembrane potential, increased Bax/Bcl-2 ratio, and activation of c-Jun N-terminal kinase and caspase-3 in BV-2 cells. Furthermore, Aβ 25-35-induced intracellular formation of reactive oxygen species and subsequent oxidative damages such as lipid peroxidation and depletion of endogenous antioxidant glutathione were suppressed by luteolin treatment. The neuroprotective effects of luteolin might be mediated by up-regulation of cellular antioxidant defense system via up-regulation of γ -glutamylcysteine ligase, a rate-limiting enzyme in the glutathione biosynthesis and superoxide dismutase, an enzyme involved in dismutation of superoxide anion into oxygen and hydrogen peroxide. Conclusions : These findings suggest that luteolin has a potential to protect against Aβ 25-35-induced neuronal cell death and damages thereby exhibiting therapeutic utilization for the prevention and/or treatment of Alzheimer's disease.

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Antioxidant Activities of Polyphenols Extracted from Perilla frutescens Varieties

Cited by 122 publications

References 16 publications

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Extraction of Luteolin and Apigenin from Leaves of <i>Perilla frutescens</i> (L.) Britt. with Liquid Carbon Dioxide

Protective Effect of Luteolin against β-Amyloid-induced Cell Death and Damage in BV-2 Microglial Cells

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