Food Chemistry 135 (2012) 24252429

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Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Isolation, identication and quantication of unsaturated fatty acids, amides,

phenolic compounds and glycoalkaloids from potato peel
Zhi-Gang Wu, Hai-Yan Xu, Qiong Ma, Ye Cao, Jian-Nan Ma, Chao-Mei Ma
College of Life Sciences, Inner Mongolia University, Huhhot, Inner Mongolia, China

a r t i c l e

i n f o

Article history:
Received 12 April 2012
Received in revised form 6 June 2012
Accepted 5 July 2012
Available online 17 July 2012
Keywords:
Potato
Omega 3-unsaturated fatty acid
Phenolic compounds
Glycoalkaloids
Antioxidant

a b s t r a c t
Eleven compounds were isolated from potato peels and identied. Their structures were determined by
interpretation of UV, MS, 1D, and 2D NMR spectral data and by comparison with reported data. The main
components of the potato peels were found to be chlorogenic acid and other phenolic compounds,
accompanied by 2 glycoalkaloids, 3 low-molecular-weight amide compounds, and 2 unsaturated fatty
acids, including an omega-3 fatty acid. The potato peels showed more potent radical scavenging activity
than the esh. The quantication of the 11 components indicated that the potato peels contained a higher
amount of phenolic compounds than the esh. These results suggest that peel waste from the industry of
potato chips and fries may be a source of useful compounds for human health.
2012 Elsevier Ltd. All rights reserved.

1. Introduction
Potatoes are one of the worlds most important staple foods,
ranking after only maize, wheat, and rice. Potato production in China
reached 72,040,000 tonnes in 2007 (FAO, 2008). This accounted for
more than one fth of the 325.30 million tonnes of potato harvested
worldwide. Potatoes contain phenolic compounds and glycoalkaloids that are especially rich in the peels. The reported phenolic components of potato skins include caffeic acid, chlorogenic acid, ferulic
acid, coumaric acid, protocatechic acid, gallic acid and vanillic acid,
which play major roles in the antioxidant activity of potato skins
(Nara, Miyoshi, Honma, & Koga, 2006; Rodriguez de Sotillo, Hadley,
& Holm, 1994). It has been reported that oxidative stress is a primary
cause of various degenerative diseases and participates in the normal ageing process (Halliwell, Gutteridge, & Cross, 1992). Potato
peel extract may be used as natural antioxidant (Kanatt, Chander,
Radhakrishna, & Sharma, 2005; Wijngaard, Ballay, & Brunton,
2011) and precursors for steroid hormones (Schieber, Marleny, &
Sladana, 2009). a-Chaconine, a potato glycoalkaloid, has been found
to induce apoptosis in human colon cancer cells and inhibit ERK 1/2
phosphorylation (Yang, Paek, Kozukue, Lee, & Kim, 2006).
Every year, tens of thousand tonnes of potatoes are made into
potato chips and fries, and most of the peels become animal feed
or are discarded. The present research was carried out to investigate the chemical components and antioxidants of potato peels.
In addition, the contents of these compounds in potato peels and
Corresponding author. Fax: +86 4992435.
E-mail address: cmma@imu.edu.cn (C.-M. Ma).
0308-8146/$ - see front matter 2012 Elsevier Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.foodchem.2012.07.019

esh were compared by ultra performance liquid chromatographyquadrupole mass spectrometry (UPLCQQQMS).
2. Material and methods
2.1. Chemicals
Solvents used for the extraction and isolation were of analytical
grade. Authentic quinic acid, chlorogenic acid and caffeic acid were
purchased from SigmaAldrich Corporation (St. Louis, MO, USA).
Methyl caffeate was prepared by treatment of caffeic acid with trimethylsilyldiazomethane (SigmaAldrich) in methanol. HPLC grade
solvents used for UPLC-diode array (DAD)electrospray ionization
(ESI)-MS were purchased from Fisher scientic company (New Jersey, USA). Silica gel (100200 mesh, Qingdao Marine Chemical Inc.,
Qingdao, China), RP-18 (3863 lm, Wako Pure Chemical Industries,
Ltd., Osaka, Japan), and Sephadex LH-20 (GE Healthcare Bio-Sciences AB, Uppsala, Sweden) were used for column chromatography.
NMR spectra were obtained from a Bruker Avance III 500 spectrometer with tetramethylsilane as internal standard. UPLC-DADESIMS experiments were carried out on an Agilent 1290 innity
UPLC-DAD system [Agilent Technologies Singapore (International)
Pte. Ltd., Singapore] with an auto-sampler and a photo-diode array
detector (DAD) coupled with an Agilent 6430 triple Quad MS.
2.2. Plant materials
Potato used in the present research was the product of Wulanchabumeng, Inner Mongolia, China. Peels for extraction were of 1

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Z.-G. Wu et al. / Food Chemistry 135 (2012) 24252429

Fig. 1. Chemical compounds from potato peels.

2 mm thickness containing a thin layer of esh similar to the byproduct of some potato-processing industry. For UPLC-DADESIMS analysis, the plant material was freeze-dried rst.

2.3. Extraction and isolation

The potato peels (2 kg) were cut to small pieces and extracted
with methanol under reux three times (2 h, 1 h and 30 min,
respectively). The methanol extracts were combined and concentrated under vacuum. The concentrated extract was partitioned
with EtOAcH2O. The EtOAc soluble part was subjected to a silica
gel column eluted with a solvent gradient of EtOAc/EtOH/H2O
(20:0:010:2:1, v/v/v). Similar fractions were combined to obtain
ve fractions (Fractions IV). Fraction I (EtOAc/EtOH/
H2O = 20:0:0, v/v/v) was subjected to an octadecylsilane (ODS or
C-18) column chromatography with a solvent gradient of MeOH/
H2O (0:100100:0, v/v). Compounds 8 (12 mg) and 9 (13 mg) were
obtained from the MeOH/H2O (30:7035:65, v/v), eluted part after
further purication. Compounds 3 (123 mg), 6 (43 mg) and 5

(98 mg) were obtained from MeOH/H2O (25:75, 70:30 and 75:25,
v/v), eluted parts of the ODS column, respectively. Compound 4
was identied from fraction II by LCMS analysis and by comparing with standard compound.
The H2O soluble part was subjected to chromatography on
Sephadex LH-20 column eluted with a solvent gradient of H2O/
MeOH (100:00:100, v/v) to obtain 10 fractions (Fraction IbXb).
Compound 1 was detected from Ib (H2O/MeOH 100:0, v/v, eluted
part) and compound 2 was detected from IIb (H2O/MeOH 90:10,
v/v, eluted part), respectively, by LCMS. Fraction IIIb was subjected to an ODS column chromatography to get compound 7
(8 mg) from MeOH/H2O (7:93, v/v), eluted part. Fraction Xb
(H2O/MeOH 10:90, v/v, eluted part) was subjected to a silica gel
column to get compound 10 (85 mg) and 11 (112 mg) from
EtOAc/EtOH/H2O 6:2:1 and 4:2:1, v/v/v, eluted part, respectively.
2.4. NMR spectral data of compound 7
Compound 7, yellowish powder. 1H NMR (D2O) d 2.97 (dd, 1H,
J = 8.0, 14.5 Hz, 7a), 3.13 (dd, 1H, J = 5.5, 14.5 Hz, 7b), 3.83(dd,

Z.-G. Wu et al. / Food Chemistry 135 (2012) 24252429

2427

Fig. 2. UPLCESIMS proles of standard compounds, potato peel and esh (from upper to bottom).

1H, J = 5.5, 8.0 Hz, 8), 7.25 (m, 5H, ArH). 13C NMR (500 MHz), 36.4
(7), 56.00 (8), 127.63 (4), 129.06 (2, 6), 129.31 (3, 5), 135.06 (1),
174.0 (9).
2.5. DPPH radical scavenging assay
The DPPH radical scavenging activity was measured using the
principles described in the literatures (Liu, David, Popovich, & Jing,
2010) with some modication. The experiment was carried out on
96-well microplates. To each well was added 10 ll of sample solution (DMSO as solvent) and 190 ll of freshly prepared DPPH solution (0.1 mM in EtOH). In the control wells, sample solution was
replaced by DMSO. To measure the absorbance of the compound
(Acolour), 10 ll of sample solution and 190 ll EtOH without DPPH
was mixed. The mixture was allowed to stand in the dark at room
temperature for 20 min before reading the absorbance at 520 nm.
The absorbance (A) of the resulting solution was measured with
a microplate reader (DNM-9602, Beijing Pu Long new technology
Co. Ltd., Beijing, China). Radical scavenging (%) was calculated
using the following formula:

DPPH radical scavenging %

100  Acontrol  Asample  Acolour =Acontrol
2.6. Quantication of the chemical components with UPLC-DADESIMS
2.6.1. Preparation of sample solutions for UPLC-DADMS analysis
The freeze-dried potato peel or esh powder (1 g) was extracted
by ultrasonication with 20 ml of methanol for 20 min. After ltration through a G3 lter plate, the ltrates were concentrated under

reduced pressure. The residue was dissolved in 20 ml of methanol

and passed through a Sep-Pak cartridge (Vac C18 3 cc, WAT020805,
waters corporation, Milford, MA, USA). The obtained solution was
ltrated through a 0.22 lm microlter to obtain the sample solution for UPLC-DADESI-MS analysis.
2.6.2. UPLC-DADESI-MS analysis
Samples were analyzed by UPLC-DADQQQMS using an Agilent
ZORBAX SB-C18 RRHT column (50  2.1 mm i.d.; particle size
1.8 lm) at 30 C. The mobile phase consisted of 0.1% formic acid
in H2O (solvent A) and 0.1% formic acid in acetonitrile (solvent
B). The elution program was set up as: 0 min, 0% B; 0.4 min, 13%
B; 1 min, 13% B; 2 min, 21% B; 3 min, 31% B; 3.5 min, 40% B;
4 min, 48% B; 4.015.5 min, 100% B. Post time: 1.5 min. The injection volume was 2 lL and the ow rate was kept at 0.4 ml/min.
MS2 scan mode (negative) was used for qualitative analysis
(Fig. 2). For quantication of the components, multiple reaction
monitoring (MRM) or selective ion monitoring (SIM) mode was
used with positive polarity for compounds 711 and negative
polarity for compounds 16. Compound 1 was analyzed at MRM
191 and 85, compound 2 at MRM 353 and 191, and compound 8
at MRM 330 and 312 after in-source fragmentation. Other compounds were quantied using SIM mode. The ion source parameters were set as following: capillary, 4 kV; gas temperature,
350 C; gas ow, 11 L/min; nebulizer, 45 psi (Table 1).
3. Results and discussions
3.1. Identication of the isolated components of the potato peel
Compounds 1 (quinic acid), 2 (chlorogenic acid), 3 (caffeic acid),
and 4 (methyl caffeate) were identied by comparing with authen-

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Z.-G. Wu et al. / Food Chemistry 135 (2012) 24252429

tic standards in UPLC-DADESI-MS experiments. The structures of

compounds 5 and 6 were determined by analysis of their 1D, 2D
NMR and MS spectra, and by comparing their spectral data with
those reported. Gao, Wang, Zhang, and Liu (2001) rst found compound 5 [9,10,11-trihydroxy-12(Z)-octadecenoic acid] in Chinese
trufe tuber inducun. Gbel et al. (2001) detected compounds 5
and 6 [9,10,11-trihydroxy-12(Z), 15(Z)-octadecadienoic acid] in
elicitor-treated potato cells and De Marino et al. (2006) fully characterized compound 6.
Compound 7 was obtained as a yellowish powder. Its 1H and 13C
NMR displayed characteristic signals for a mono-substituted benzene ring. Besides, there were signals at d 2.97 (dd, 1H, J = 8.0,
14.5 Hz) and 3.13 (dd, 1H, J = 5.5, 14.5 Hz) for a methylene group,
and a signal at d 3.83 (dd, 1H, J = 5.5, 8.0 Hz) for a proton linked at
an oxygenated carbon. A carbonyl signal at d 174.0 was found in
its 13C NMR. Its negative ESIMS displayed a quasi-molecular ion
at 164 [MH]. This, in combination with the information obtained
from NMR spectra, suggested a molecular formula of C9H11NO2 for
compound 7. In the HMBC spectrum, long range correlations were
found between the methylene protons and two kinds of aromatic
carbons, suggesting the direct linkage of the methylene group to
the benzene ring. The proton on the oxygenated carbon was found
to have long range correlation with one of the benzene carbon, suggesting it was linked next to the methylene group. The HMBC correlations of these aliphatic protons with the carbonyl carbon
make it possible to determine the whole structure of compound 7
as 2-hydroxy-3-phenyl-propionamide. This compound has been reported as an intermediate compound for the chemical synthesis of
some compounds having a model pharmacophore structure of
mycalamides, the natural anti-tumor agents from marine sponge
(Abell, Blunt, Foulds, & Munro, 1997). This is the rst report of 2-hydroxy-3-phenyl-propionamide from potato.
The structures of compounds 8 and 9 were determined by analysis of their 1D and 2D NMR as well as MS spectral data. The position of a methoxy group in compound 8 was determined by
nuclear Overhauser effect (NOE) experiment. Signicant NOE effect
was observed for a doublet signal with a small J-value at d 7.12 (d,
J = 2.0 Hz) when the signal of the methoxy group at d 3.88 ppm was
irradiated, indicated that the methoxy group was at the meta-position in the structure of 8. Compound 8 {N-[2-hydroxy-2-(4hydroxyphenyl) ethyl] ferulamide, trans-N-feruloyloctopamine},
and 9 (cis-N-feruloyloctopamine) are trans and cis isomers which
were rst reported by Muhlenbeck, Kortenbusdh, and Barz
(1996). These two compounds were reported from potato common
scab lesions (King & Calhoun, 2005) and detected in potato via
induction of redox sensitive extracellular phenolic amides (Baker
et al., 2009).
Compounds 10 and 11, the two major glycoalkaloids in potato,
were identied as a-chaconine and a-solanine, respectively, by
interpretation of their NMR and MS spectra data and by compari-

Table 2
Radical scavenging activity of the components and extracts of potato.
Samplea

EC50b (lg/ml) S.D.

Compound 2
Compound 3
Compound 4
Compound 8
Compound 9
Potato peel extract
Potato esh extract
Vc (positive control)

15.7 0.04
9.8 0.03
21.2 0.16
77.5 0.21
80.2 0.17
1.5 0.08
15.2 0.09
21.5 0.04

Compounds 1, 57 and 1011 showed less than 50% of activity at 100 lg/ml.
EC50: the concentration that showed 50% of radical scavenging activity on
DPPH.
b

son with those reported in literatures (Bianco, Schmitt-Kopplin,

Benedetto, Kettrup, & Cataldi, 2002; Gong, 1986) (Fig. 1).
3.2. Antioxidant activity of the extracts and components
Table 2 shows the DPPH scavenging activity of the extracts of
potato esh, potato peel, and the compounds from potato peel.
The strongest DPPH scavenging activity was observed in the peel
extract, which is stronger than any of the isolated compounds.
The reason for this may be that the peel contains some other compounds that are much stronger DPPH scavengers, or because of the
synergistic antioxidant effect of multiple components in the extract. Of the pure compounds isolated, caffeic acid and chlorogenic
acid showed high DPPH scavenging activity, higher than the positive control, vitamin C. Of the two extracts, potato peel showed
stronger DPPH scavenging activity than potato esh, which was
in agreement with the reported data (Nara et al., 2006).
3.3. Analysis of the components of the potato peel and potato esh
The results for quantitative analysis of compounds 111 are
listed in Table 3. As shown in Table 3, higher levels of glycoalkaloids were found in potato peels than in the esh, which was in
agreement with reported data (Ieri, Innocenti, Andrenelli, Vecchio,
& Mulinacci, 2011). Glycoalkaloids may play a role in defence
against pests or microorganisms. Compounds 3 and 4 were detected in the peel but could hardly be found in the esh. Low levels
of compound 8 were detected in potato peels, but no compound 9
was detected. This suggests that compound 9, a cis-isomer of compound 8, may be formed from compound 8 under the inuence of
light during the extraction process. Putt, Nesterenko, Dothager, and
Hergenrother (2006) have reported that compound 8/9 selectively
induced apoptosis in cancerous white blood cells. The potential
uses of potato peels and potato peel products containing these

Table 1
UPLCESIMS data for the constituents of potato peels.

Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
a
b

1
2
3
4
5
6
7
8
9
10
11

Retention time (min)

Charge

Calibration curvea

R2

LODb (lg/mL)

0.43
1.50
1.83
3.24
4.46
4.24
1.10
2.76
2.52
3.54
3.49

N
N
N
N
N
N
P
P
P
P
P

y = 80546x + 293.95
y = 8.2E + 5x + 4581.4
y = 350648x + 77.643
y = 353360x + 69.5
y = 2E + 06x + 273.5
y = 337307x + 40.75
y = 24654x + 13.820
y = 151837x + 3.5
y = 23347x + 321.76
y = 7.1E + 7x + 60454
y = 5.0E + 6x + 4120.9

0.9973
0.9955
0.9984
0.9981
0.9991
0.9983
0.9999
0.9977
0.9984
0.9987
0.9966

1.24
0.009
0.23
0.42
0.002
0.015
1.25
0.002
<0.001
0.14
<0.001

y is the signal area and x is the concentration in lg/mL.

LOD: limit of detection.

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Z.-G. Wu et al. / Food Chemistry 135 (2012) 24252429

Table 3
Contents of the chemical components in potato peel and esh (mg/g dry powder).

Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
Compound
a
b
c

1
2
3
4
5
6
7
8
9
10
11

Peel 2011a

Peel 2012b

Flesh 2011a

Flesh 2012b

0.71 0.04
3.87 0.04
2.23 0.08
0.002 0.001
0.02 0.0001
0.01 0.0015
0.13 0.01
0.02 0.00
n.d
2.00 0.09
8.89 0.36

0.63 0.03
1.26 0.06
0.72 0.0026
0.033 0.004
0.03 0.0007
0.02 0.0005
0.16 0.0017
0.07 0.01
n.d
0.77 0.01
3.52 0.03

0.23 0.01
1.0 0.07
n.dc
n.d
0.001 0.0002
0.0023 0.0001
1.02 0.02
n.d
n.d
0.26 0.16
1.52 0.09

0.16 0.0063
0.60 0.01
n.d
n.d
0.02 0.001
0.02 0.0017
0.15 0.0040
0.0018 9.31E  05
n.d
0.32 0.01
2.18 0.04

2011: Potato peel/esh were analyzed in September, 2011, 2 months after harvest.
2012: Potato peel/esh were analyzed in March, 2012, 6 months after harvest.
n.d = Not detectable.

compounds in the treatment of blood cancer merits further investigation. Potato peel was found to contain more phenolic compounds than potato esh. As stocking time increased, levels of
phenolic compounds decreased. Both the potato peel and the esh
were found to contain notable amounts of unsaturated fatty acids,
compounds 5 and 6. Compound 5 is an omega-6 fatty acid, and
compound 6 is an omega-3 fatty acid, which is rarely found in
plants. Omega-3 fatty acids, such as eicosapentaenoic acid (EPA)
and docosahexaenoic acid (DHA), are known to have health benets, such as prevention of coronary heart disease and stroke. Besides, they are known to be essential fatty acids for infant brain
and retinal development (Connor, 2000). The main source of EPA
is seafood; however, EPA can also come from the in vivo conversion
of a short-chain omega-3 fatty acid, alpha-linolenic acid (Burdge &
Calder, 2005). The biological activity of the omega-3 fatty acid from
potato, compound 6, may merit further investigation. It, like alphalinolenic acid, may be converted into EPA or DHA in vivo.
4. Conclusions
Potato peels were found to contain a variety of components,
including phenols, unsaturated fatty acids, and glycoalkaloids. An
omega-3 fatty acid, 9,10,11-trihydroxy-12(Z),15(Z)-octadecadienoic acid, was found in both potato peel and potato esh and it
may be an important part of the benecial effects of potato consumption. The phenolic compounds showed strong antioxidant
activity, and higher levels were observed in potato peels than in
potato esh. Potato peels, which are wasted in the production of
potato chips and fries, merit more attention and more utilization.
Acknowledgements
This work was supported by a Grant from the Department of
Science and Technology of Inner Mongolia, China. The authors
are grateful to Mr. Meng He for helping with the nuclear magnetic
resonance instrument.
Appendix A. Supplementary data
Supplementary data associated with this article can be found,
in the online version, at http://dx.doi.org/10.1016/j.foodchem.
2012.07.019.
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