Chemistry and Biological Activities of Flavonoids: An Overview

There has been increasing interest in the research on flavonoids from plant sources because of their versatile health benefits reported in various epidemiological studies. Since flavonoids are directly associated with human dietary ingredients and health, there is need to evaluate structure and function relationship. The bioavailability, metabolism, and biological activity of flavonoids depend upon the configuration, total number of hydroxyl groups, and substitution of functional groups about their nuclear structure. Fruits and vegetables are the main dietary sources of flavonoids for humans, along with tea and wine. Most recent researches have focused on the health aspects of flavonoids for humans. Many flavonoids are shown to have antioxidative activity, free radical scavenging capacity, coronary heart disease prevention, hepatoprotective, anti-inflammatory, and anticancer activities, while some flavonoids exhibit potential antiviral activities. In plant systems, flavonoids help in combating oxidative stress and act as growth regulators. For pharmaceutical purposes cost-effective bulk production of different types of flavonoids has been made possible with the help of microbial biotechnology. This review highlights the structural features of flavonoids, their beneficial roles in human health, and significance in plants as well as their microbial production.

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Apigetrin Promotes Cell Autophagy by Activating the Endoplasmic Reticulum Stress in Human Cervical Cancer Hela Cells

Current Topics in Nutraceutical Research ◽

10.37290/ctnr2641-452x.20:56-63 ◽

2021 ◽

Vol 20 (1) ◽

pp. 56-63

Author(s):

Li Jiang ◽

Zhi-Cheng Yao ◽

Miao-Miao Liu ◽

Run-Hui Ma ◽

Kiran Thakur

Keyword(s):

Cervical Cancer ◽

Endoplasmic Reticulum ◽

Er Stress ◽

Hela Cells ◽

Fruits And Vegetables ◽

Radical Scavenging ◽

Anticancer Activities ◽

Treatment Results ◽

Metastasis Rate ◽

The Relationship

Cervical cancer has always been the top malignant cancer among female cancers in the world. Due to its recurrence, metastasis rate, and drug resistance, the treatment results of cervical cancer have been unsatisfactory. Apigetrin is present in a variety of fruits and vegetables and has been reported to have antioxidant, free radical scavenging, anti-inflammatory, and anticancer activities. Therefore, this study focuses on the effect of apigetrin on the autophagy of cervical cancer HeLa cells based on the previous research. The results showed that apigetrin can enhance the autophagy fluorescence of light chain 3B (LC3B), and further combined with quantitative real-time PCR (qPCR) and Western blotting found that the expression of autophagy-related genes and proteins p-mTOR, Beclin1, and LC3B increased, while the expression of AMPK, ULK1, and p62 decreased. In addition, apigetrin also promoted the release of Ca2+, the PERK/eIF2α/ATF4/chop, and IRE1α pathways activate endoplasmic reticulum (ER) stress. The addition of 4PBA proved that ER stress promoted autophagy in HeLa cells. Finally, the addition of the 3-MA indicates the relationship between autophagy and apoptosis in HeLa cells. Our results indicate that apigetrin has a certain anticancer potential and can be used as a drug adjuvant and food additive for the prevention and treatment of cervical cancer.

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Recent advances in chalcone-based anticancer heterocycles: A structural and molecular target perspective

Current Medicinal Chemistry ◽

10.2174/0929867328666210322102836 ◽

2021 ◽

Vol 28 ◽

Author(s):

Vishal Kumar ◽

Sanjeev Dhawan ◽

Pankaj Sanjay Girase ◽

Paul Awolade ◽

Suraj Raosaheb Shinde ◽

...

Keyword(s):

Histone Deacetylases ◽

Biological Activities ◽

Molecular Targets ◽

Cathepsin K ◽

Cost Effective ◽

Sirtuin 1 ◽

Anticancer Activities ◽

Structural Variations ◽

Research Attention ◽

Endothelial Growth Factor

: Chalcones are an interesting class of compounds endowed with a plethora of biological activities beneficial to human health. These chemo types have continued to attract increased research attention over the years; hence, numerous natural and synthetic chalcones have found with interesting anticancer activities through the inhibition of various molecular targets including ABCG2, BCRP, P-glycoprotein, 5α-reductase, Androgen receptor (AR), Histone deacetylases (HDAC), Sirtuin 1, proteasome, Vascular endothelial growth factor (VEGF), Cathepsin-K, tubulin, CDC25B phosphatase, Topoisomerase, EBV, NF-κB, mTOR, BRAF and Wnt/β-catenin. Moreover, the study of intrinsic mechanisms of action, particularly relating to specific cellular pathways and modes of engagement with molecular targets, may help medicinal chemists to develop a more effective, selective, and cost-effective chalcone-based anticancer drugs. This review, therefore, sheds light on the effect of structural variations on the anticancer potency of chalcone hybrids reported in 2018-2019 alongside their mechanism of action, molecular targets, and potential impacts on effective cancer chemotherapy.

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Biological Properties of 6-Gingerol: A Brief Review

Natural Product Communications ◽

10.1177/1934578x1400900736 ◽

2014 ◽

Vol 9 (7) ◽

pp. 1934578X1400900 ◽

Cited By ~ 10

Author(s):

Shaopeng Wang ◽

Caihua Zhang ◽

Guang Yang ◽

Yanzong Yang

Keyword(s):

Fruits And Vegetables ◽

Biological Activities ◽

Zingiber Officinale ◽

Biological Properties ◽

Anticancer Activities ◽

Inhibition Of Angiogenesis ◽

Underlying Mechanisms ◽

Pharmacologically Active

Numerous studies have revealed that regular consumption of certain fruits and vegetables can reduce the risk of many diseases. The rhizome of Zingiber officinale (ginger) is consumed worldwide as a spice and herbal medicine. It contains pungent phenolic substances collectively known as gingerols. 6-Gingerol is the major pharmacologically-active component of ginger. It is known to exhibit a variety of biological activities including anticancer, anti-inflammation, and anti-oxidation. 6-Gingerol has been found to possess anticancer activities via its effect on a variety of biological pathways involved in apoptosis, cell cycle regulation, cytotoxic activity, and inhibition of angiogenesis. Thus, due to its efficacy and regulation of multiple targets, as well as its safety for human use, 6-gingerol has received considerable interest as a potential therapeutic agent for the prevention and/or treatment of various diseases. Taken together, this review summarizes the various in vitro and in vivo pharmacological aspects of 6-gingerol and the underlying mechanisms.

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Antioxidant and Antidiabetic Effects of Flavonoids: A Structure-Activity Relationship Based Study

BioMed Research International ◽

10.1155/2017/8386065 ◽

2017 ◽

Vol 2017 ◽

pp. 1-14 ◽

Cited By ~ 55

Author(s):

Murni Nazira Sarian ◽

Qamar Uddin Ahmed ◽

Siti Zaiton Mat So’ad ◽

Alhassan Muhammad Alhassan ◽

Suganya Murugesu ◽

...

Keyword(s):

Radical Scavenging ◽

Structural Features ◽

Biochemical Properties ◽

Hydroxyl Groups ◽

Dpph Radical ◽

Dot Blot ◽

Antioxidant Power ◽

Dipeptidyl Peptidase 4 ◽

Ferric Reducing Antioxidant Power

The best described pharmacological property of flavonoids is their capacity to act as potent antioxidant that has been reported to play an important role in the alleviation of diabetes mellitus. Flavonoids biochemical properties are structure dependent; however, they are yet to be thoroughly understood. Hence, the main aim of this work was to investigate the antioxidant and antidiabetic properties of some structurally related flavonoids to identify key positions responsible, their correlation, and the effect of methylation and acetylation on the same properties. Antioxidant potential was evaluated through dot blot, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, ABTS+radical scavenging, ferric reducing antioxidant power (FRAP), and xanthine oxidase inhibitory (XOI) assays. Antidiabetic effect was investigated throughα-glucosidase and dipeptidyl peptidase-4 (DPP-4) assays. Results showed that the total number and the configuration of hydroxyl groups played an important role in regulating antioxidant and antidiabetic properties in scavenging DPPH radical, ABTS+radical, and FRAP assays and improved bothα-glucosidase and DPP-4 activities. Presence of C-2-C-3 double bond and C-4 ketonic group are two essential structural features in the bioactivity of flavonoids especially for antidiabetic property. Methylation and acetylation of hydroxyl groups were found to diminish thein vitroantioxidant and antidiabetic properties of the flavonoids.

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Nutritional and clinical relevance of lutein in human health

British Journal Of Nutrition ◽

10.1079/bjn2003927 ◽

2003 ◽

Vol 90 (3) ◽

pp. 487-502 ◽

Cited By ~ 198

Author(s):

F. Granado ◽

B. Olmedilla ◽

I. Blanco

Keyword(s):

Clinical Practice ◽

Human Health ◽

Visual Function ◽

Fruits And Vegetables ◽

Biological Activities ◽

Serum Levels ◽

Epidemiological Studies ◽

Age Related ◽

Beneficial Impact ◽

Based Medicine

Lutein is one of the most widely found carotenoids distributed in fruits and vegetables frequently consumed. Its presence in human tissues is entirely of dietary origin. Distribution of lutein among tissues is similar to other carotenoids but, along with zeaxanthin, they are found selectively at the centre of the retina, being usually referred to as macular pigments. Lutein has no provitamin A activity in man but it displays biological activities that have attracted great attention in relation to human health. Epidemiological studies have shown inconsistent associations between high intake or serum levels of lutein and lower risk for developing cardiovascular disease, several types of cancer, cataracts and age-related maculopathy. Also, lutein supplementation has provided both null and positive results on different biomarkers of oxidative stress although it is effective in increasing macular pigment concentration and in improving visual function in some, but not all, subjects with different eye pathologies. Overall, data suggest that whereas serum levels of lutein have, at present, no predictive, diagnostic or prognostic value in clinical practice, its determination may be very helpful in assessing compliance and efficacy of intervention as well as potential toxicity. In addition, available evidence suggests that a serum lutein concentration between 0·6 and 1·05 μmol/l seems to be a safe, dietary achievable and desirable target potentially associated with beneficial impact on visual function and, possibly, on the development of other chronic diseases. The use of lutein as a biomarker of exposure in clinical practice may provide some rationale for assessing its relationship with human health as well as its potential use within the context of evidence-based medicine.

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Flavonoids – World Healthiest Gift for the Benefit of Human Health

Journal of Commercial Biotechnology ◽

10.5912/jcb716 ◽

2015 ◽

Vol 21 (4) ◽

Author(s):

Abhishek Kumar Yadav

Keyword(s):

Antioxidative Activity ◽

Radical Scavenging ◽

Epidemiological Studies ◽

Anticancer Activities ◽

Radical Scavenging Capacity ◽

Scavenging Capacity ◽

Major Nutrient ◽

Antiviral Activities ◽

Fitness Benefits ◽

Plant Sources

Flavonoids are one of the major nutrient families recognized to scientists, and comprise over 6,000 already recognized family members. A number of the best - recognized flavonoids include quercetin, kaempferol, catechins, and anthocyanidins. It is well-known for its antioxidative activity, free radical scavenging capacity, coronary, hepatoprotective, anti-inflammatory and anticancer activities. Some flavonoids also exhibit potential antiviral activities. There has been rising attention in the research on flavonoids from plant sources because of their resourceful fitness benefits reported in a variety of epidemiological studies. Study on the health aspects of flavonoids for humans is growing speedily.

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Antibacterial, antioxidant, cytotoxic effects and GC-MS analysis of mangrove-derived Streptomyces achromogenes tch4 extract

Archives of Biological Sciences ◽

10.2298/abs210320017t ◽

2021 ◽

pp. 17-17

Author(s):

Janpen Tangjitjaroenkun ◽

Wanchai Pluempanupat ◽

Rungnapa Tangchitcharoenkhul ◽

Waraporn Yahayo ◽

Roongtawan Supabphol

Keyword(s):

Ethyl Acetate ◽

Ethyl Acetate Extract ◽

Biological Activities ◽

Radical Scavenging ◽

Bioactive Metabolites ◽

Total Phenolic ◽

Anticancer Activities ◽

Antioxidant Power ◽

Dry Extract

The in vitro biological activities of the ethyl acetate extract of the culture filtrate from Streptomyces achromogenes TCH4 (TCH4 extract) were evaluated. The ethyl acetate extract of TCH4 produced a bacteriostatic effect against Enterobacter cloacae, Staphylococcus aureus, Staphylococcus saprophyticus, Bacillus subtilis, methicillin-resistant S. aureus (MRSA) and Klebsiella pneumoniae. The extract had bactericidal activity against S. aureus, S. saprophyticus, S. aureus (MRSA) and K. pneumoniae with minimum bactericidal concentration (MBC) values in the range of 500-1000 ?g/mL. The total phenolic and flavonoid contents in TCH4 were 107.20?2.57 mg gallic acid equivalent (GAE)/g and 44.91?0.84 mg quercetin equivalent (QE)/g of dry extract. Antioxidant activity was determined by DPPH radical (IC50 299.64?6.83 ?g/mL) and ABTS radical scavenging (IC50 65.53?0.95 ?g/mL), and the ferric-reducing antioxidant power (FRAP) (822.76?9.12 mM FeSO4.7H2O/g dry extract) assays. TCH4 exhibited cytotoxic activity in the DU-145 cell line (IC50 9.36?0.37 ?g/mL). Analysis of extract constituents by GC-MS revealed pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl) (36.85%), benzeneacetamide (23.76%), and deferoxamine (12.85%) as the major compounds, which have been reported to possess pharmaceutical properties. S. achromogenes TCH4 could be a potential source of bioactive metabolites with antibacterial, antioxidant and anticancer activities for pharmaceutical applications.

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Antioxidant and Antisteatotic Activities of a New Fucoidan Extracted from Ferula hermonis Roots Harvested on Lebanese Mountains

Molecules ◽

10.3390/molecules26041161 ◽

2021 ◽

Vol 26 (4) ◽

pp. 1161

Author(s):

Zeinab El Rashed ◽

Giulio Lupidi ◽

Hussein Kanaan ◽

Elena Grasselli ◽

Laura Canesi ◽

...

Keyword(s):

Therapeutic Potential ◽

Biological Activities ◽

Radical Scavenging ◽

Bioactive Compound ◽

13C Nmr Spectroscopy ◽

Antioxidant Property ◽

Structural Features ◽

Water Soluble ◽

Cellular Models

Fucoidan is a fucose-rich sulfated polysaccharide with attractive therapeutic potential due to a variety of biological activities, including antioxidant action. Fucoidan is typically found in the cell wall of marine brown algae, but extra-algal sources have also been discovered. In the present work, for the first time we extracted a water soluble fucoidan fraction from the roots of the terrestrial shrub Ferula hermonis. This fucoidan fraction was termed FUFe, and contained fucose, glucose, sulfate, smaller amounts of monosaccharides such as galactose and mannose, and a minor quantity of proteins. FUFe structural features were investigated by FTIR, 1H NMR and 13C NMR spectroscopy. The antioxidant property of FUFe was measured by DPPH, ABTS and FRAP assays, which revealed a high radical scavenging capacity that was confirmed in in vitro cellular models. In hepatic and endothelial cells, 50 μg/mL FUFe could reduce ROS production induced by intracellular lipid accumulation. Moreover, in hepatic cells FUFe exhibited a significant antisteatotic action, being able to reduce intracellular triglyceride content and to regulate the expression of key genes of hepatic lipid metabolism. Altogether, our results candidate FUFe as a possible bioactive compound against fatty liver disease and related vascular damage.

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Acetylenic Aquatic Anticancer Agents and Related Compounds

Natural Product Communications ◽

10.1177/1934578x0600100914 ◽

2006 ◽

Vol 1 (9) ◽

pp. 1934578X0600100 ◽

Cited By ~ 1

Author(s):

Valery M Dembitsky ◽

Dmitri O Levitsky ◽

Tatyana A Gloriozova ◽

Vladimir V Poroikov

Keyword(s):

Anticancer Agents ◽

Biological Activities ◽

Aquatic Organisms ◽

Structural Features ◽

Biologically Active ◽

Terrestrial Plants ◽

Anticancer Activities ◽

Pharmaceutical Industries ◽

New Applications

Although acetylenes are common as components of terrestrial plants, it is only within the last 30 years that biologically active polyacetylenes having unusual structural features have been reported from aquatic organisms: cyanobacteria, algae, fungi, invertebrates, and other sources. Naturally occurring aquatic acetylenes are of particular interest since many of them display important biological activities and possess antitumor, antibacterial, antimicrobial, antifouling, antifungal, pesticidal, phototoxic, HIV inhibitory, and immuno-suppressive properties. There is no doubt that they are of great interest, especially for the medicinal and/or pharmaceutical industries. This review presents structures and describes cytotoxic and anticancer activities of more than 230 acetylenic metabolites isolated from aquatic organisms. With the computer program PASS some additional biological activities are also predicted, which point toward possible new applications of these compounds. This review emphasizes the role of aquatic acetylenic compounds as an important source of leads for drug discovery.

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Optimization of Ultrasound-Assisted Extraction of Flavonoids from Celastrus hindsii Leaves Using Response Surface Methodology and Evaluation of Their Antioxidant and Antitumor Activities

BioMed Research International ◽

10.1155/2020/3497107 ◽

2020 ◽

Vol 2020 ◽

pp. 1-9 ◽

Cited By ~ 1

Author(s):

Dinh-Chuong Pham ◽

Hoang-Chinh Nguyen ◽

Thanh-Hang Le Nguyen ◽

Hoang-Linh Ho ◽

Thien-Kim Trinh ◽

...

Keyword(s):

Response Surface Methodology ◽

Response Surface ◽

Biological Activities ◽

Radical Scavenging ◽

Ultrasonic Power ◽

Extraction Temperature ◽

Anticancer Activities ◽

Ultrasound Assisted Extraction ◽

Assisted Extraction ◽

Ultrasound Assisted

Celastrus hindsii is a potential source of flavonoids with biological activities. This study aimed to develop an ultrasound-assisted technique for extracting flavonoids from leaves of C. hindsii. Response surface methodology was employed to optimize the extraction conditions for maximizing the total flavonoid content (TFC). A maximum TFC of 23.6 mg QE/g was obtained under the extraction conditions of ultrasonic power of 130 W, extraction temperature of 40°C, extraction time of 29 min, and ethanol concentration of 65%. The flavonoid-rich extracts were then studied for their antioxidant and anticancer activities. The results showed that the C. hindsii leaf extract exhibited potent radical scavenging activities against DPPH (IC50 of 164.85 μg/mL) and ABTS (IC50 of 89.05 μg/mL). The extract also significantly inhibited the growth of 3 cancer cell lines MCF7, A549, and HeLa with the IC50 values of 88.1 μg/mL, 120.4 μg/mL, and 118.4 μg/mL, respectively. Notably, the extract had no cytotoxicity effect on HK2 normal kidney cell line. This study suggests that flavonoid-rich extract is a promising antioxidant and anticancer agent and that ultrasound-assisted extraction is an efficient method for extracting flavonoids from C. hindsii leaves.

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