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Article history:
Received 10 August 2007
Received in revised form 6 March 2008
Accepted 10 March 2008
Coenzyme Q10 (CoQ10) was emulsied with fats and emulsiers commonly used in the food industry, and
the oral bioavailability of the emulsied product was compared with that of a standard commercial
product. Five commonly used fats (olive oil, safower oil, coconut oil, butter, and cocoa butter), four types
of emulsier (lecithin, monoglycerides, calcium stearoyl-2-lactate (CSL), and diacetyl tartaric acid esters
of monoglycerides), and two types of aqueous phase (distilled water with or without 8 g/100 g w/w skim
milk) were employed in this study. It was found that CoQ10 was more soluble in coconut and safower
oils than in the other fats. In addition, it was demonstrated that emulsion with coconut oil, skim milk
aqueous solution, and CSL produced an optimal formulation. Based on the results, a model emulsied
CoQ10 product was prepared. Its oral bioavailability was conrmed to be slightly greater than that of
a standard commercial CoQ10 product.
2008 Swiss Society of Food Science and Technology. Published by Elsevier Ltd. All rights reserved.
Keywords:
Coenzyme Q10
Emulsion
Oral bioavailability
1. Introduction
Coenzyme Q10 (CoQ10; ubiquinol-10 and/or ubiquinone-10)
plays the essential role of electron carrier and proton translocator
during cellular respiration and ATP production and protects
numerous cellular membranes and plasma lipoproteins against free
radical-induced damage. CoQ10 is primarily obtained from meat,
poultry, sh, and rapeseed oil (Mattila & Kumpulainen, 2001;
Purchas, Busboom, & Wilkinson, 2006). In recent years, the use of
CoQ10 as a nutritional supplement has attracted much attention.
Numerous CoQ10 products are available on the market, including
tablets (chewable and non-chewable), powder-lled capsules, and
soft gels containing an oil suspension (Bhagavan & Chopra, 2007).
The oral bioavailability of CoQ10 in these products is very low
because of its high molecular weight and poor water solubility. In
the past few years, there has been an extensive effort to improve
the oral bioavailability of CoQ10 in nutritional supplements.
Various formulations for improvement of the oral bioavailability of
CoQ10 have been investigated, including molecular complexes (Gao
et al., 2006; Terao et al., 2006; Ueno, Ijitsu, Horiuchi, Hirayama, &
Uekama, 1989), emulsions (Carli, Chiellini, Bellich, Macchiavelli, &
Cadelli, 2005; Kang et al., 2004; Kommuru, Gurley, Khan, & Reddy,
2001; Nazzal et al., 2002; Nazzal, Smalyukh, Lavrentovich, & Khan,
2002; Palamakula & Khan, 2004), and liposomal systems (Xia, Xu, &
Zhang, 2006; Xia, Xu, Zhang, & Zhong, 2007). Some of the formulations have been conrmed to have greater oral bioavailability of CoQ10
* Corresponding author. Tel./fax: 81 426 37 2193.
E-mail address: kajiwara@bs.teu.ac.jp (K. Kajiwara).
0023-6438/$34.00 2008 Swiss Society of Food Science and Technology. Published by Elsevier Ltd. All rights reserved.
doi:10.1016/j.lwt.2008.03.006
386
State
Oleic
Palmitic Linoleic
Myristic Stearic
Lauric
acid
acid
acid
acid
acid
acid
(g/100 g) (g/100 g) (g/100 g) (g/100 g) (g/100 g) (g/100 g)
Olive
Safower
Coconut
Butter
Cocoa
Liquid
Liquid
Liquid
Solid
Solid
77
77
7
22
34
10
5
9
33
25
7
14
2
2
3
17
12
3
2
3
10
35
47
4
Fig. 1. Solubility of CoQ10 in fats. Data are shown as mean SD (n 4). Tests were
performed in four replicates. Means with the same letter are not signicantly different
(P < 0.05).
Table 2
The average size and stability of emulsions after storage
Oil
Safower oil
Butter
Cocoa butter
Olive oil
Coconut oil
Emulsier
Amount of
oil (g/100 g)
30 days (mm)
Stability
Water
0 day (mm)
30 days (mm)
Stability
CSL
5
10
30
1.84 0.29
2.22 0.63
2.10 0.68
2.15 0.25
No
No
1.72 0.22
1.64 0.2
1.74 0.27
2.11 0.20
No
No
MG
5
10
30
1.91 0.25
1.46 0.21
1.85 0.39
No
No
No
2.15 0.52
1.87 0.22
1.72 0.46
No
No
No
LC
5
10
30
2.05 0.23
1.81 0.22
2.14 0.25
No
No
No
2.07 0.23
2.04 0.23
1.98 0.26
No
No
No
DATEM
5
10
30
1.82 0.33
1.84 0.25
2.32 0.29
No
No
No
1.75 0.34
2.16 0.28
2.12 0.24
No
No
No
CSL
5
10
30
1.75 0.33
2.04 0.23
1.98 0.48
1.91 0.22
2.03 0.28
No
1.98 0.37
1.99 0.48
2.11 0.46
No
No
No
MG
5
10
30
1.67 0.33
1.77 0.29
2.01 0.48
2.08 0.33
2.11 0.24
No
1.93 0.41
2.16 0.41
2.07 0.47
No
No
No
LC
5
10
30
1.75 0.33
2.04 0.23
1.98 0.48
2.14 0.22
No
No
1.98 0.37
1.99 0.48
2.11 0.46
No
No
No
DATEM
5
10
30
1.66 0.28
2.07 0.33
2.24 0.24
No
No
No
1.65 0.29
1.92 0.29
2.14 0.49
No
No
No
CSL
5
10
30
1.99 0.29
2.05 0.33
1.91 0.55
No
No
No
2.09 0.47
2.12 0.51
2.33 0.47
No
No
No
MG
5
10
30
1.99 0.35
2.04 0.32
2.03 0.27
No
No
No
2.09 0.39
2.38 0.56
2.41 0.73
No
No
No
LC
5
10
30
2.05 0.45
2.06 0.34
2.06 0.55
No
No
No
2.36 0.55
2.30 0.70
2.58 0.77
No
No
No
DATEM
5
10
30
1.76 0.29
1.78 0.26
2.03 0.44
No
No
No
1.84 0.28
1.81 0.25
2.02 0.56
No
No
No
CSL
5
10
30
2.09 0.34
2.06 0.46
1.79 0.52
No
No
No
2.03 0.28
2.15 0.49
2.11 0.44
2.07 0.39
No
No
MG
5
10
30
1.86 0.27
1.84 0.25
2.11 0.19
No
No
No
2.06 0.56
2.11 0.52
2.19 0.56
No
No
No
LC
5
10
30
1.74 0.21
1.88 0.24
2.13 0.19
No
No
No
2.14 0.27
2.03 0.26
1.93 0.24
No
No
No
DATEM
5
10
30
1.85 0.25
2.09 0.29
2.03 0.25
No
No
No
1.84 0.25
1.93 0.26
2.02 0.24
No
No
No
CSL
5
10
30
1.46 0.23
1.72 0.23
1.78 0.19
1.71 0.26
1.82 0.23
No
1.84 0.22
1.86 0.24
1.79 0.23
No
No
No
MG
5
10
30
1.82 0.23
2.06 0.22
2.19 0.38
2.05 0.23
2.58 0.44
No
1.87 0.21
1.88 0.26
2.17 0.26
No
No
No
LC
5
10
30
1.63 0.20
1.93 0.22
1.94 0.44
1.96 0.23
No
No
1.84 0.25
1.96 0.19
1.97 0.23
No
No
No
DATEM
5
10
30
1.71 0.29
1.66 0.25
1.88 0.25
1.96 0.27
No
No
1.49 0.21
2.12 0.29
2.08 0.33
1.83 0.24
2.36 0.44
No
: no separation; : partial separation; : completely separation between oil and continuous phase.
no: droplet size did not observe.
388
containing 30 g/100 g w/w fat and most of the emulsions containing 10 g/100 g w/w fat separated into their lipid and aqueous
phases during storage; the stability of the emulsions decreased
with increased content of fats. For the economy of space, only the
typical droplet size distribution of the emulsion with 5 g/100 g
coconut oil with the various emulsiers is shown here in Fig. 2.
Emulsiers with high HLB (CSL, HLB 79 and DATEM,
HLB 810) tended to be more effective than those with low HLB
(MG and LC, HLB 34), that is the maximum peak of droplet size
distribution in the emulsion with high HLB present in the smaller
range, and CSL maintained a more homogenous oil droplet than
DATEM did. Addition of 8 g/100 g w/w skim milk into the aqueous
phase stabilized the emulsion. In addition, the emulsion with
coconut oil, 8 g/100 g skim milk aqueous solution, and CSL has the
good stability and small droplet size. From the solubility of CoQ10 in
fats experiment, coconut oil signicantly provided high solubility of
CoQ10. Therefore, it was concluded that this emulsion was an
optimal formulation.
Fig. 2. Size distribution in the emulsion with 5 g/100 g coconut oil, 8 g/100 g skim milk aqueous solution with the various emulsiers after storage for 0 day.
389
Fig. 3. Total content of CoQ10 (TQ) at each stage: (1) before administration of CoQ10; (2)
after administration of the standard commercial CoQ10 product during 1 week after
lunch; (3) 3 weeks after the administration of the CoQ10 product was stopped; and (4)
after administration of the model emulsied CoQ10 product during 1 week after lunch.
Data are shown as mean SD (n 5). Means with the same letter are not signicantly
different (P < 0.05).
Fig. 4. The ratio of total content of CoQ10 to total content of cholesterol (TQ/TC) at each
stage, as shown in Fig. 3. Data are shown as mean SD (n 5). Means with the same
letter are not signicantly different (P < 0.05).
390
Purchas, R. W., Busboom, J. R., & Wilkinson, B. H. P. (2006). Changes in the forms of
iron and in concentrations of taurine, carnosine, coenzyme Q10, and creatine in
beef longissimus muscle with cooking and simulated stomach and duodenal
digestion. Meat Science, 74, 443449.
Sohmiya, M., Tanaka, M., Tak, N. W., Yanagisawa, M., Tanino, Y., & Suzuki, Y., et al.
(2004). Redox status of plasma coenzyme Q10 indicates elevated systemic oxidative stress in Parkinsons disease. Journal of the Neurological Sciences, 223,
161166.
Tanino, Y., Budiyanto, A., Ueda, M., Nakada, A., Nyou, W. T., & Yanagisawa, M., et al.
(2005). Decrease of antioxidants and the formation of oxidized diacylglycerol in
mouse skin caused by UV irradiation. Journal of Dermatological Science
Supplement, 1, S21S28.
Terao, K., Nakata, D., Fukumi, H., Schmid, G., Arima, H., & Hirayama, F., et al. (2006).
Enhancement of oral bioavailability of coenzyme Q10 by complexation with
g-cyclodextrin in healthy adults. Nutrition Research, 26, 503508.
Ueno, M., Ijitsu, T., Horiuchi, Y., Hirayama, F., & Uekama, K. (1989). Improvement of
dissolution and absorption characteristics of ubidecarenone by dimethyl-bcyclodextrin complexation. Acta Pharmaceutica Nordica, 2, 94104.
Wada, H., Hagiwara, S., Saitoh, E., Ieki, R., Okamura, T., & Ota, T., et al. (2006). Increased oxidative stress in patients with chronic obstructive pulmonary disease
(COPD) as measured by redox status of plasma coenzyme Q10. Pathophysiology,
13, 2933.
Xia, S., Xu, S., & Zhang, X. (2006). Optimization in the preparation of coenzyme Q10
nanoliposomes. Journal of Agricultural and Food Chemistry, 54, 63586366.
Xia, S., Xu, S., Zhang, X., & Zhong, F. (2007). Effect of coenzyme Q10 incorporation
on the characteristics of nanoliposomes. Journal of Physical Chemistry B, 111,
22002207.
Yamashita, S., & Yamamoto, Y. (1997). Simultaneous detection of ubiquinol and
ubiquinone in human plasma as a marker of oxidative stress. Analytical
Biochemistry, 250, 6673.