The antioxidant activity of some curcuminoids and chalcones

Sökmen, Münevver; Khan, Muhammad Akram

doi:10.1007/s10787-016-0264-5

Cited by 81 publications

(47 citation statements)

References 22 publications

(25 reference statements)

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“…Chalcone, (E)-1,3-diphenyl-2-propene-1-one, has been reported as being a precursor in flavonoid synthesis [1]. Similar to flavonoids, chalcones have already been documented as exhibiting several biological activities, including antioxidant [2], anti-inflammatory [3], antibacterial and antifungal [4], antiprotozooal [5], immunomodulatory [6], and antiangiogenic [7,8] effects. Furthermore, antiproliferative/antitumor activities of chalcones have also been intensively studied [9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative Effect of Acridine Chalcone Is Mediated by Induction of Oxidative Stress

et al. 2020

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Chalcones are naturally occurring phytochemicals with diverse biological activities including antioxidant, antiproliferative, and anticancer effects. Some studies indicate that the antiproliferative effect of chalcones may be associated with their pro-oxidant effect. In the present study, we evaluated contribution of oxidative stress in the antiproliferative effect of acridine chalcone 1C ((2 E)-3-(acridin-9-yl)-1-(2,6-dimethoxyphenyl)prop-2-en-1-one) in human colorectal HCT116 cells. We demonstrated that chalcone 1C induced oxidative stress via increased reactive oxygen/nitrogen species (ROS/RNS) and superoxide production with a simultaneous weak adaptive activation of the cellular antioxidant defence mechanism. Furthermore, we also showed chalcone-induced mitochondrial dysfunction, DNA damage, and apoptosis induction. Moreover, activation of mitogen activated phosphokinase (MAPK) signalling pathway in 1C-treated cancer cells was also observed. On the other hand, co-treatment of cells with strong antioxidant, N-acetyl cysteine (NAC), significantly attenuated all of the above-mentioned effects of chalcone 1C, that is, decreased oxidant production, prevent mitochondrial dysfunction, DNA damage, and induction of apoptosis, as well as partially preventing the activation of MAPK signalling. Taken together, we documented the role of ROS in the antiproliferative/pro-apoptotic effects of acridine chalcone 1C. Moreover, these data suggest that this chalcone may be useful as a promising anti-cancer agent for treating colon cancer.

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Section: Introductionmentioning

confidence: 99%

Antiproliferative Effect of Acridine Chalcone Is Mediated by Induction of Oxidative Stress

et al. 2020

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“…Moreover mechanisms of action of bioactive compounds isolated from A. pindrow also needs to be further explored for clarity of pharmacological actions. There has been reports from various studies that chalcones behave as strong antioxidants [69,70] and antiproliferative activities [71,72]. Since chalcones have been isolated from the barks of A. pindrow, investigations on anticancer and antiproliferative activity also needs to be undertaken for development of anticancer drug.…”

Section: Conclusion and Future Prospectsmentioning

confidence: 99%

Ethnobotanical and Pharmacological Importance of Western Himalayan Fir Abies pindrow (Royle ex D. Don) Royle: A Review

Sinha¹

2019

JPRI

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Aims: Abies pindrow (Royle ex D. Don) Royle., colloquially known as the Western Himalayan fir, is a conifer that grows along the Himalayan mountains from Afghanistan to Nepal. The plant is extensively used by locals for the treatments of various ailments. Thus based on the available reports about its importance in traditional system of medicine, an attempt has been made to review this species in context of its medicinal and pharmaceutical importance. Study Design: The review article has been designed based on literature survey. The article is grossly divided into four broad phases consisting of compiled information of Abies pindrow: (1) Ethnobotanical information (2) Chemical Constituents (3) Pharmacological activities (4) Discussion mainly highlighting the mode of action of the bioactive compounds in relation to its pharmacological activity. Methodology: Extensive literature search have been performed in the web using PubMed, PubMed Central, google scholar as search platform. Efforts have also been taken to compile information from research papers and review articles not more than 10 years old. Information from old literatures were preferably avoided unless found to be very relevant to the subject. Results: The literature survey revealed that the plant has been used to treat cough and cold, diabetes, cataract and bladder diseases. The plant is also considered to be carminative, astringent, antispasmodic, diuretic, tonic and anti-inflammatory. The plant is also rich in terpenes and terpene alcohols. Testing for antidiabetic, neuroprotective, anticataract and antixiolytic activities have been promising and the bioactive constituents and efforts are made to interpret the possible mechanism of action of bioactive compounds in bringing about the pharmacological activities. Conclusion: It is concluded that the plant can be explored and bioprospected for an affordable source of drug and nutraceutical for better management of health related issues of people of Indian subcontinent.

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“…The curcuminoids include curcumin (the main bioactive component), demethoxycurcumin and bisdemethoxycurcumin [1,2,3]. The unique structure of curcumin, which has the phenolic hydroxyl groups, heptadiene chain and diketone moiety [4,5,6], is responsible for all the therapeutic activities of curcumin such as anti-inflammatory, antitumor, anticancer, anti-HIV, antibacterial, antidiabetic [7,8,9,10,11,12,13]. It is used as an antioxidant [9], a wound healing agent [14,15,16] and to prevent Alzheimer disease [17,18].…”

Section: Introductionmentioning

confidence: 99%

“…In basic medium, the degradation occurs by nucleophilic attack of basic -OH (hydroxyl) ion. Feruloylmethane (6) and ferulic acid (7) are formed by the alkaline hydrolysis of curcumin. The feruloylmethane further undergoes hydrolysis to form vanillin (8) and acetone (9) [35] (Figure 3).…”

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confidence: 99%

Structure activity relationship of tautomers of curcumin: a review

Rege¹,

Arya²,

Momin³

2019

Ukr. food j.

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Introduction. The aim of this review is to focus on the unique chemistry of curcumin to explain its dissimilar behaviour in different mediums. Materials and methods. The papers regarding structure-activity relationship studies of curcumin as antioxidant or pro-oxidant were examined. This review summarizes the achievements made in this field since 1980. Results and discussion. Curcumin is the principal curcuminoid found in turmeric and is generally considered as the most active constituent of turmeric compared to other curcuminoids. Enormous research has been carried out to explain the beneficial activities of curcumin. It has been the centre of attraction for potential treatment of an array of diseases such as cancer, Alzheimer, diabetes, allergies, arthritis and other chronic illnesses. It also possesses antioxidant activity at lower concentration. In contrast, the pro-oxidant effect has also been reported. The behaviour of curcumin to act as antioxidant or pro-oxidant depends on its structural form. Curcumin exists in two tautomeric forms, keto and enol. In keto form, curcumin exerts antioxidant activity. The enol form is prone to degradation. Hence, it is essential to maintain curcumin in keto form. In polar and acidic medium, curcumin exists in keto form whereas in non-polar and basic medium, it undergoes degradation. The mechanisms of degradation of curcumin under different mediums are discussed. Under basic conditions, nucleophilic attack of hydroxyl group is involved and under non-polar conditions, free radical mechanism is involved. Degradation under basic conditions leads to complete breaking of the molecule while under non-polar conditions, it proceeds via peroxide intermediate formation, clarifying the pro-oxidant effect of curcumin. In either of the cases, vanillin is the degradation product besides other degradation products. The discussion is further extended for the other two curcuminoids, viz. demethoxycurcumin and bisdemethoxycurcumin as well. The antioxidant activity of curcumin is the highest whereas bisdemethoxycurcumin exhibits least antioxidant activity amongst curcuminoids. However, the rate of degradation of curcumin is also maximum amongst curcuminoids followed by demethoxycurcumin and bisdemethoxycurcumin. This reveals that the electron donating methoxy group influences the activity of curcuminoids. Thus, structure of a constituent is responsible for its activity. Conclusion. The importance of a particular medium to achieve the beneficial activities of curcumin is confirmed.

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The antioxidant activity of some curcuminoids and chalcones

Cited by 81 publications

References 22 publications

Antiproliferative Effect of Acridine Chalcone Is Mediated by Induction of Oxidative Stress

Antiproliferative Effect of Acridine Chalcone Is Mediated by Induction of Oxidative Stress

Ethnobotanical and Pharmacological Importance of Western Himalayan Fir Abies pindrow (Royle ex D. Don) Royle: A Review

Structure activity relationship of tautomers of curcumin: a review

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