Effect of Demethoxycurcumin and Bisdemethoxycurcumin on Antioxidant Activity of Curcumin in Refined Sunflower Oil

Rege, Sameera A.; Momin, Shamim A.; Wadekar, Sushant; Pratap, Amit P.; Bhowmick, D. N.

doi:10.1111/j.1745-4549.2012.00777.x

Cited by 15 publications

(10 citation statements)

References 24 publications

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“…[13] The antioxidant activity of curcumin was studied in refined sunflower oil (RSFO). [73] Antifibrotic Effect Punithavathi and coworkers [74] observed that oral administration of curcumin suppressed bleomycin-induced pulmonary fibrosis in rats.…”

Section: Subjectsmentioning

confidence: 99%

Curcumin and its protective and therapeutic uses

Agrawal¹,

Goel²

2016

Natl J Physiol Pharm Pharmacol

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Curcumin is a yellow orange powder, which is extracted from the turmeric plant (Curcuma longa). Curcumin is the principal curcuminoid of the turmeric (C. longa). Curcumin was first isolated in 1815 and its chemical structure was determined by Roughley and Whiting in 1973. It has been identified as 1,6-heptadiene-3,5-dione-1,7-bis (4-hydroxy-3-methoxyphenyl)-(1e,6e) or diferuloylmethane. Turmeric has been listed as ''generally recognized as safe'' (GRAS) as a coloring and flavoring agent in food by the US Food and Drug Administration (FDA). As per WHO, as an additive the daily acceptable dose of curcumin for humans has been defined as 0-3 mg/kg body weight. Curcumin can be administered by different routes as topical, oral, and inhalational. Curcumin inserts deep into the cell membrane in a manner similar to cholesterol. Curcumin has a high lipophilic character, and body fat has a high percentage of bound curcumin. The systemic bioavailability of orally administered curcumin is low in humans and only traces of it have been found in the liver and portal circulation. Piperine has been reported to increase the bioavailability of curcumin. Recently, it has been reported that newly developed nanoparticulate curcumin has better bioavailability. There is a growing list of disease conditions that can be treated by curcumin. Curcumin has been found to have therapeutic effects in wound healing and in various types of arthritis, cardiovascular diseases, diabetes, pulmonary diseases, Parkinson's disease, and in Alzheimer's disease. Curcumin has been reported to have potential role in the treatment of atherosclerosis, arthritis, chronic anterior uveitis, colon cancer, familial adenomatous polyposis, hypercholesteremia, inflammatory bowel disease, pancreatic cancer, pancreatitis, psoriasis, ulcerative colitis, and even HIV.

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Section: Subjectsmentioning

confidence: 99%

Curcumin and its protective and therapeutic uses

Agrawal¹,

Goel²

2016

Natl J Physiol Pharm Pharmacol

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“…Also, since they possess electron donating hydroxyl group in the aromatic ring and electron withdrawing carbonyl group in heptadienone moiety, structures (3) and (4) can be drawn respectively. The existence of structures (3) and (4) has already been proven by NMR data [14]. Structures 3 and 4 resemble the enol tautomer ( Figure 1).…”

Section: Proportion Of Keto and Enol Tautomers Of Curcuminoidsmentioning

confidence: 53%

Mini review on Keto-Enol ratio of curcuminoids

Rege¹,

Arya²,

Momin³

2019

UJFS

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Introduction. Curcumin, demethoxycurcumin and bisdemethoxycurcumin collectively constitute curcuminoids, exhibit different rates of degradation as well as therapeutic properties. Their remarkable dissimilar behaviour is affiliated to their tendency to undergo keto-enol tautomerism whereas their rates of degrading and imparting therapeutic properties depend on the ratio of keto and enol tautomers of individual curcuminoid. Materials and Methods. The aim of the current review is to focus on the ratio of keto and enol tautomers and to explain how the ratio of the two tautomers affects the rate of activities of the curcuminoids. The papers regarding variations in the rate of activities of curcuminoids were scrutinized. The factors affecting the ratio of keto-enol tautomerism were studied. Results and discussion. Structurally, curcuminoids are the compounds possessing β-diketone moiety. The characteristic property of compounds containing β-diketone moiety is to exhibit keto-enol tautomerism. Hence, each curcuminoid is a mixture of keto and enol tautomers. The keto tautomer of curcumioids is responsible for their therapeutic activities. On the other hand, enol tautomer of curcuminods has tendency to undergo degradation. Hence, the ratio of keto and enol tautomer needs to be considered while studying the activities of curcuminoids. Nevertheless, the ratio of keto and enol tautomer depends on the existence of other functional groups. Because of the presence of electron donating hydroxyl group, the proportion of enol tautomer predominates in curcuminoids. Further, due to the presence of two more electron donating methoxy groups in curcumin, the ratio of the enol tautomer is higher and hence, the susceptibility to undergo degradation is greater than demethoxycurcumin, which contains only one methoxy group. The ratio of the enol tautomer is minimum in bisdemethoxycurcumin amongst all the curcuminoids, which is devoid of methoxy group. Consequently, bisdemethoxycurcumin has the least rate of degradation amongst curcuminoids. Methoxy group enhances the activity of the functional sites in curcuminoids in keto form. Therefore, curcumin shows maximum beneficial activities in keto form amongst all the curcuminoids, followed by demethoxycurcumin and bisdemthoxycurcumin. Thus, the rate of the activities displayed by curcuminoids is governed by their keto and enol proportion. Conclusion. It can be concluded from this review article that besides β-diketone moiety, responsible for keto-enol tautomerism, other groups also play an important role in determining the ratio of keto and enol tautomers.

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“…Curcumin has higher pharmacological activity than bisde methoxycurcumin and demethoxycurcumin (Sandur et al 2007;Jayaprakasha et al 2006). However, the mixture of three curcuminoids has better activity compared only curcumin (Rege et al 2014).…”

Section: Introductionmentioning

confidence: 92%

Quantitative Analysis of Multi-components in Curcuma xanthorrhiza by Single Marker

Hakim

Soloviov²,

Nirwati

et al. 2020

Indonesian J. Pharm.

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A new simple and effective routine analytical method for quantification of curcuminoids in Curcuma xanthorrhiza was developed by highperformance liquid chromatography. This method based on chromatographic fingerprint combined with a quantitative analysis of multi-components by single marker (QAMS). Curcumin was selected as an internal marker for the determination of two other similar compounds, i.e. bisdemethoxycurcumin and demethoxycurcumin, by using the relative coefficient factor (RCF). Excellent linearity was obtained for each component (r 2 >0.9998), and the recovery of extraction methods were within 100.23-103.95%. The precision of the method was good at inter-day and intra-day analysis (RSD<4.0%). The stability of RCFs was good under various chromatographic conditions with RSD < 1%, and the ratio of retention time was used to locate each compound. The quantification of curcuminoids between QAMS and external standard method (ESM) proved the consistency and similarity of the two method (RSD <2%). This study demonstrated that QAMS could be used as a routine method for quality control of curcuminoids in C. xanthorrhiza. This method successfully proved accurate, stable, more effective and simple than external standard method.

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Effect of Demethoxycurcumin and Bisdemethoxycurcumin on Antioxidant Activity of Curcumin in Refined Sunflower Oil

Cited by 15 publications

References 24 publications

Curcumin and its protective and therapeutic uses

Curcumin and its protective and therapeutic uses

Mini review on Keto-Enol ratio of curcuminoids

Quantitative Analysis of Multi-components in Curcuma xanthorrhiza by Single Marker

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