Natural Product Research

Formerly Natural Product Letters

ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20

Comparison of antioxidant, anticholinesterase,

and antidiabetic activities of three curcuminoids
isolated from Curcuma longa L.

Zeynep Kalaycıoğlu, Işıl Gazioğlu & F. Bedia Erim

To cite this article: Zeynep Kalaycıoğlu, Işıl Gazioğlu & F. Bedia Erim (2017) Comparison
of antioxidant, anticholinesterase, and antidiabetic activities of three curcuminoids
isolated from Curcuma longa L., Natural Product Research, 31:24, 2914-2917, DOI:
10.1080/14786419.2017.1299727

To link to this article: http://dx.doi.org/10.1080/14786419.2017.1299727

View supplementary material Published online: 13 Mar 2017.

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Download by: [Gothenburg University Library] Date: 06 November 2017, At: 02:53
 Natural Product Research, 2017
VOL. 31, NO. 24, 2914–2917
https://dx.doi.org/10.1080/14786419.2017.1299727

SHORT COMMUNICATION

Comparison of antioxidant, anticholinesterase, and

antidiabetic activities of three curcuminoids isolated from
Curcuma longa L.
Zeynep Kalaycıoğlua, Işıl Gazioğlub and F. Bedia Erima
a
Department of Chemistry, Istanbul Technical University, Istanbul, Turkey; bFaculty of Pharmacy, Department
of Analytical Chemistry, Bezmialem Vakıf University, Istanbul, Turkey
Downloaded by [Gothenburg University Library] at 02:53 06 November 2017

ABSTRACT ARTICLE HISTORY

Antioxidant, anticholinesterase and antidiabetic activities of three Received 5 December 2016
curcuminoids isolated from the Curcuma longa were simultaneously Accepted 18 February 2017
tested and compared in this study. The highest antioxidant power
KEYWORDS
was detected for curcumin with the applied methods. The drug Turmeric; curcumin;
potentials of curcuminoids for Alzheimer’s disease were controlled. demethoxycurcumin;
Bisdemethoxycurcumin (BDMC) showed substantial inhibitory activity. bisdemethoxycurcumin;
The activity of demethoxycurcumin (DMC) followed BDMC, whereas bioactivity;
curcumin showed very little acetylcholinesterase inhibition activity. acetylcholinesterase
Antidiabetic activity of curcuminoids was evaluated by their α-glucosidase
inhibitory activities. All curcuminoids show activities with decreasing
order as BDMC > curcumin > DMC. The significant activities of BDMC
compared to its isomers and examination of chemical structures of
isomers might be a starting point in designing new drugs for Alzheimer’s
and Diabetes Mellitus.

1. Introduction
Curcuma species (Zingiberaceae) have long been used in traditional medicine in Asian coun-
tries. Recent studies revealed their bioactive constituents, as mainly curcumin and some

CONTACT  F. Bedia Erim  erim@itu.edu.tr

 Supplemental data for this article can be accessed at http://dx.doi.org/10.1080/14786419.2017.1299727.
© 2017 Informa UK Limited, trading as Taylor & Francis Group
 NATURAL PRODUCT RESEARCH   2915

others (Rameshkumar et al. 2015). Curcuma longa or with a common name turmeric is exten-
sively used worldwide as a spice, food preservative and colouring material. Extensive studies
have been done with turmeric to reveal the biological activity of this spice and interest is
mainly focussed on curcumin as the important bioactive component of turmeric (Elseweidy
et al. 2015; Maione et al. 2016; Zhang et al. 2016). However, recent chromatographic assays
revealed that three curcuminoids, namely curcumin, demethoxycurcumin (DMC) and bis-
demethoxycurcumin (BDMC), always exist together in turmeric samples (Wichitnithad et al.
2009; Kalaycıoğlu et al. 2015). In our previous study, we developed a sensitive analysis
method to quantify three curcuminoids in turmeric (Kalaycıoğlu et al. 2015). Following this
work, in the present study, antioxidant, anticholinesterase and antidiabetic activities of the
curcuminoids isolated from the same turmeric source were found and compared using in
vitro models. Antioxidant activities of curcuminoids were carried out in the two common
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test models, namely DPPH free-radical scavenging and FRAP assays. The drug potentials of
curcuminoids for Alzheimer’s disease were controlled with their inhibition effects against
acetylcholinesterase (AChE) and butrylcholinesterase (BChE) enzymes. Antidiabetic activity
of curcuminoids was evaluated by their α-glucosidase inhibitory activities.

2.  Results and discussion

The results of the present study are given in Table 1. All individual curcuminoids possess
antioxidant activities according to the methods investigated. The antioxidant activities of
curcuminoids decrease in the order: curcumin > demethoxycurcumin > bisdemethoxycur-
cumin. Only two reports exist in the literature giving antioxidant power of three curcuminoids
from turmeric. Ramsewak et al. (2000) reported antioxidant activities of three curcuminoids
with iron-catalysed liposome model and % inhibition of liposome peroxidation of curcumi-
noids. Jayaprakasha et al. (2006) reported phosphomolybdenum and linoleic acid method
for antioxidant activities of curcuminoids. The correlations between the antioxidant activity
orders of curcuminoids found with our methods and two other different antioxidant methods
are in agreement.

Table 1. In vitro inhibition (IC50) and FRAP assay values of compounds for antioxidant, anticholinesterase
and antidiabetic activities.
Antidiabetic
Antioxidant activity Anticholinesterase activity activity
α-Glucosidase
DPPH assay FRAP assay AChE assay BChE assay inhibitory assay
Compounds IC50 (μM)a (μM Fe(II)/g)a IC50 (μM)a IC50 (μM)a IC50 (μM)a
Curcumin 0.72 ± 0.01 1884 ± 63 51.8 ± 0.6 N.A 21.1 ± 0.3
DMC 6.62 ± 0.03 1432 ± 42 19.7 ± 0.2 N.A 26.4 ± 0.2
BDMC 80.2 ± 0.0 667 ± 19 2.14 ± 0.78 67.2 ± 0.6 12.5 ± 0.2
BHAb 1.18 ± 0.03 – – – –
Ascorbic acidb – 10,846 ± 126 – – –
Galantamineb – – 2.41 ± 0.12 17.4 ± 0.6 –
Genisteinb – – – – 2.50 ± 0.02
a
Data represents the means ± S.D of three paralel measurements (p < 0.05).
b
Standard compounds.
N.A: Not active.
 2916   Z. KALAYCIOĞLU ET AL.

The results of AChE and BChE inhibitory activities of tested curcuminoids were expressed
as IC50 (μM). As shown in Table 1, BDMC shows significant AChE inhibition activity, which is
even better than the AChE inhibition value of galantamine which is used as a standard drug.
Among three curcuminoids, curcumin shows much less activity as acetylcholinesterase
inhibitor. The results are in agreement with the study on AChE inhibitory activities of cur-
cuminoids (Ahmed & Gilani 2009). Curcumin and DMC show no inhibitory activity against
BChE, whereas BDMC shows enzyme activity inhibition. The present study reports the BChE
activities of three curcuminoids for the first time.
The concentrations of curcuminoids for 50% inhibition of the α-glucosidase enzymatic
activity decrease in the order: bisdemethoxycurcumin > curcumin > demethoxycurcumin.
BDMC is significantly the most potent compared to the others. The activities of curcumin
and DMC are almost similar. Du et al. (2006) reported the potential of synthetic curcumin
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analogues as inhibitor of human pancreatic α-amylases. The inhibitory behaviour of three

curcuminoids among others are in agreement with the order of our study.

3. Conclusion
Antioxidant activities, acetylcholinesterase (AChE) and butrylcholinesterase (BChE) inhibitory
activities, and antidiabetic activities of three curcuminoids isolated from Curcuma longa L.
were simultaneously investigated in the present study. All these studies suggested that small
differences in the chemical structures of isomers strongly affect biological activities of indi-
vidual curcuminoids. The findings in this research might be useful in designing new drugs
for Alzheimer’s and Diabetes Mellitus.

Supplementary material
Supplementary materials relating to this article are experimental section, Table S1, Table S2 and Figure
S1.

Disclosure statement
No potential conflict of interest was reported by the authors.

Funding
This study was supported by the Research Foundation of Istanbul Technical University.

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