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Isolation and Optical Properties of Natural Pigments from Purple

Mangosteen Peels
To cite this article: Yehezkiel Steven Kurniawan et al 2020 IOP Conf. Ser.: Mater. Sci. Eng. 833 012018

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The 2nd International Conference on Chemistry and Material Science (IC2MS) IOP Publishing
IOP Conf. Series: Materials Science and Engineering 833 (2020) 012018 doi:10.1088/1757-899X/833/1/012018

Isolation and Optical Properties of Natural Pigments from

Purple Mangosteen Peels

Yehezkiel Steven Kurniawan1, M. Riza Ghulam Fahmi1, and Leny Yuliati1,2,*

1
Ma Chung Research Center for Photosynthetic Pigments, Universitas Ma Chung,
Villa Puncak Tidar N-01, Malang 65151, East Java, Indonesia
2
Department of Chemistry, Faculty of Science and Technology, Universitas Ma
Chung, Villa Puncak Tidar N-01, Malang 65151, East Java, Indonesia

*Corresponding author: [email protected]

Abstract. Purple mangosteen (Garcinia mangostana) has several biological applications such
as anticancer, antitubercular and antioxidant agents. In this work, we isolated and studied the
optical properties of the natural pigments from the purple mangosteen peels. To isolate the
natural pigments, the mangosteen peels were macerated using distilled water, ethanol, or
acetone for 24 h. The extracts were filtrated and characterized using spectrophotometers of
Fourier transform infrared (FTIR), ultraviolet-visible (UV-Vis), and spectrofluorometer. The
extracts gave the FTIR vibration peaks of O-H, C-H sp3, C=O, C=C, and C-O functional
groups, while absorption peaks at 210‒374 nm were observed in the UV-Vis spectra of the
extracts due to the presence of mangostins, anthocyanins, and phenolic acids. The three-
dimensional fluorescence spectra showed that the excitation and emission peaks of the
mangosteen peels extracted with ethanol were found at 444 and 498 nm, respectively, while
that extracted with distilled water gave no significant fluorescence peaks. On the other hand,
the mangosteen peels extracted with acetone gave the strongest emission intensity at 472 and
502 nm due to the most intense color intensity. This study provided useful information about
the optical properties of natural pigments extracted from purple mangosteen peels through a
simple isolation technique.

1. Introduction
Purple mangosteen (Garcinia mangostana) is a widely abundant tropical fruit in tropical countries. In
general, it can be found in the Malay Archipelago especially in Indonesia. Purple mangosteen has been
well recognized due to its excellent biological activities [1], therefore purple mangosteen is well-
known as the queen of fruits [2]. Orozco et al. and Palawakong et al. reported that the biological
activities of purple mangosteen are generated by xanthones, phenolic acids, anthocyanins, flavonoids,
tannins, and carotenoids [3, 4]. Xanthones especially their prenylated and oxygenated compounds
exhibit excellent antimicrobial activity against Mycobacterium tuberculosis, Staphylococcus aureus,
Candida albicans, Plasmodium falciparum, etc. Because of that, mangosteen has been thoroughly
investigated and employed as antitubercular and antimalarial agents [5, 6]. Furthermore, the
anticancer, antioxidant, anti-inflammatory, anti-tumorigenic and anti-obesogenic activities of purple
mangosteen have been also evaluated either in in vitro or in vivo studies [7‒9].
In contrast to the excellent biological activities of the purple mangosteen flesh, the purple
mangosteen peels were rarely utilized and thrown as the waste. Some researchers are putting effort to
minimize the waste and utilize them for other potential applications [10‒12]. Therefore, in the present
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The 2nd International Conference on Chemistry and Material Science (IC2MS) IOP Publishing
IOP Conf. Series: Materials Science and Engineering 833 (2020) 012018 doi:10.1088/1757-899X/833/1/012018

work, the natural pigments from purple mangosteen peels were extracted through a maceration method
and their optical properties were studied for a possible application as photonic and dye-sensitized
materials. Distilled water, ethanol and acetone were employed as the media for natural pigments
extraction process and the obtained extracts were characterized using spectrophotometers of Fourier
transform infrared (FTIR), ultraviolet-visible (UV-Vis), and spectrofluorometer.

2. Experimental Section
Purple mangosteen fruits were bought from a supermarket in Malang, East Java. On the other hand,
ethanol and acetone were obtained in EMPLURA grade from Merck. At first, as much as 1 kg of
purple mangosteen fruit was cleaned with distilled water to remove the soil and other impurities. The
peel of purple mangosteen was separated from its flesh, chopped and dried at 25 °C for 20 h. Then, 5 g
of purple mangosteen peel was macerated with 50 mL of either distilled water or ethanol or acetone
separately for 24 h. Afterwards the extract was characterized with a Fourier transform infrared (FTIR)
spectrophotometer (JASCO FTIR-6800), an ultraviolet-visible (UV-Vis) spectrophotometer (JASCO
V-760), and a spectrofluorometer (JASCO FP-8500).

3. Results and Discussion

In the present work, the natural pigments were extracted from purple mangosteen peels and their
optical properties were investigated. Through a simple maceration method, three extracts of the purple
mangosteen peels were successfully obtained and their photograph is shown in Figure 1. Figure 1
shows that the yellow color intensity was increased in the order of using distilled water, ethanol and
acetone solvents. From the naked eye investigation, it could be predicted that the concentration of the
natural pigments in acetone was higher than ethanol and was also higher than distilled water extract.

Figure 1. The photograph images of the purple mangosteen peel extract in (a) distilled water, (b)
ethanol and (c) acetone.

To identify the functional groups of the extracted natural pigments, the FTIR spectra of the extract
was measured by attenuated total reflectance (ATR) method. Before spectrum recording, the extract
was treated using nitrogen gas flow to remove the used solvents. The FTIR spectra of the extracts are
shown in Figure 2. The FTIR spectrum of the distilled water extract (Figure 2(a)) gave six main
absorption peaks at 3319, 2972, 2872, 1735, 1375, and 1054 cm-1. The presence of alkyl groups (R-
CH2-R’) was indicated by the presence of C-H sp3 stretching (2972 and 2872 cm-1) and -CH3 bending
(1375 cm-1) peaks, while the presence of carbonyl ester and hydroxyl groups was confirmed by the
presence of C=O stretching (1735 cm-1), C-O stretching (1054 cm-1) and O-H stretching (3319 cm-1),
respectively.
The FTIR spectrum of the ethanolic extract (Figure 2(b)) gave eight main absorption peaks at 3440,
2938, 2828, 1686, 1419, 1363, 1207 and 1052 cm-1. The presence of alkyl groups was shown by the
presence of C-H sp3 stretching (2938 and 2828 cm-1), -CH2- bending (1419 cm-1), and -CH3 bending
(1363 cm-1) peaks, while the presence of the carboxylic acid functional group was confirmed by the
presence of O-H stretching (3440 cm-1), C=O stretching (1686 cm-1), and C-O ester (1027 cm-1). On
the other hand, the FTIR spectrum of the acetone extract (Figure 2(c)) gave five main absorption peaks

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The 2nd International Conference on Chemistry and Material Science (IC2MS) IOP Publishing
IOP Conf. Series: Materials Science and Engineering 833 (2020) 012018 doi:10.1088/1757-899X/833/1/012018

at 2969, 1738, 1365, 1215 and 1052 cm-1. The presence of alkyl groups was shown by the presence of
C-H sp3 stretching (2969 cm-1), and -CH3 bending (1365 cm-1) peaks, while the presence of the ester
functional group was confirmed by the presence of C=O stretching (1738 cm-1), and either C-O ether
(1215 cm-1) or C-O ester (1052 cm-1) functional groups.
From the FTIR spectra, both distilled water and ethanolic extracts showed that they contained polar
natural pigments as the carboxylic acid and/or alcohol groups were detected. However, due to the low
polarity of acetone as a non-polar solvent, the non-polar natural pigments were extracted as confirmed
by its FTIR spectrum. This is in agreement with “like dissolve like” principle in which polar solvent
gave higher possibility and suitability to extract polar natural pigments and vice versa [13].

(a)
1735 1375
%Transmittance (a.u.)

2872
3319 2972 1054
(b)
2838
2938 1419
3440 1052
1686 1363 1207
(c)
1052
1365 1215
2969 1738
4000 3500 3000 2500 2000 1500 1000 500
Wavenumber (cm-1)

Figure 2. The FTIR spectra of the purple mangosteen peel extract in (a) distilled water, (b) ethanol
and (c) acetone.

The optical properties of each extract were studied by UV-Vis and fluorescence measurements. The
UV-Vis spectra of the extracts of purple mangosteen peels are shown in Figure 3 (a), (b) and (c) when
using distilled water, ethanol and acetone as the media, respectively. The UV-Vis spectrum of the
distilled water extract gave weak absorption peaks at 210, 283 and 374 nm (Figure 3 (a)), while the
ethanolic extract gave a little bit stronger absorption peaks at 240, 256, 320 and 360 nm (Figure 3 (b)).
Among the media, acetone extract gave the strongest absorption intensity. The absorption peaks were
observed at 248, 258, 312, and 354 nm (Figure 3 (c)), in which agreed with the color appearance of the
extract. The UV-Vis spectrum of the distilled water extract showed the absorption peaks at 210 and
374 nm, corresponding to the presence of the mangostin compounds (including α-mangostin, β-
mangostin, ɣ-mangostin, gartanin and garcinone E), while the absorption peak at 283 nm
corresponding to the presence of anthocyanin pigments (including cyanidin-3-sophoroside and
cyanidin-3-glucoside) [14–16]. On the other hand, the characteristic absorption peak of cinnamic acid
(256 nm), sinapinic acid (240 and 320 nm) and syringaldehyde (240 and 360 nm) were found at the
ethanolic extract [17–19]. Similar to the ethanolic extract, the acetone extract also contained these
pigments. However, their absorption peaks, i.e. cinnamic acid (258 nm), sinapinic acid (248 and 312
nm) and syringaldehyde (248 and 354 nm) were shifted due to the solvatochromic effect. The
chemical structures of these compounds are shown in Figure 4, while further investigation is still
required to confirm these natural pigments either by liquid chromatography-mass spectrometry (LC-
MS) or nuclear magnetic resonance (NMR) analysis.

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The 2nd International Conference on Chemistry and Material Science (IC2MS) IOP Publishing
IOP Conf. Series: Materials Science and Engineering 833 (2020) 012018 doi:10.1088/1757-899X/833/1/012018

258
248

312
Absorbance (in a.u.)

354
(c)
240
256 320
360
210 (b)

283
374
(a)
200 300 400 500 600 700 800
Wavelength (nm)

Figure 3. UV-Vis spectra of the purple mangosteen peel extract in (a) distilled water, (b) ethanol and
(c) acetone.

O OH
OH
O
OH

Cl-
HO O+
HO O OH

Mangosteen
Cinammic acid O
O
OH OH
O O O
OH
HO OH

HO OH OH
O
O O Anthocyanin

Sinapinic acid Syringaldehyde

Figure 4. Chemical structures of the natural pigments found in the extracts of purple mangosteen peel.

The three-dimensional fluorescence spectra of the extracts are shown in Figure 5. The x-axis of the
three-dimensional fluorescence spectrum shows the emission wavelength and the y-axis shows the
excitation wavelength. Meanwhile, the z-axis shows the fluorescence intensity from 0 (black color) to
200 (red color) units. The three-dimensional fluorescence spectrum of the distilled water extract gave
a very low fluorescence intensity, while ethanolic and acetone extract gave a stronger fluorescence
spectrum as indicated by the color appearance.

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The 2nd International Conference on Chemistry and Material Science (IC2MS) IOP Publishing
IOP Conf. Series: Materials Science and Engineering 833 (2020) 012018 doi:10.1088/1757-899X/833/1/012018

(a) (b)

(c)

Figure 5. Three-dimensional fluorescence spectra of the purple mangosteen peel extract in (a) distilled
water, (b) ethanol and (c) acetone.

In good agreement to the three-dimensional fluorescence spectra, the two-dimensional fluorescence

spectrum of distilled water extract showed no significant absorption peak. The two-dimensional
fluorescence spectra of ethanolic and acetone extracts are shown in Figure 6 (a) and (b), respectively.
Corresponding to its three-dimensional spectrum, the ethanolic extract gave the main excitation and
emission signals at 444 and 498 nm. Meanwhile, the acetone extract gave a single excitation signal at
452 nm and three emission signals at 472, 502 and 667 nm. According to their UV-Vis spectra shown
in Figure 3 (b) and (c), the ethanolic and acetone extracts contained cinnamic acid, sinapinic acid and

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The 2nd International Conference on Chemistry and Material Science (IC2MS) IOP Publishing
IOP Conf. Series: Materials Science and Engineering 833 (2020) 012018 doi:10.1088/1757-899X/833/1/012018

syringaldehyde compounds. However, these major compounds did not seem to be the emissive ones. It
was found that the ethanolic extract gave a similar fluorescence spectrum to that of the anthocyanin
compounds [20], while the acetone extract showed similar fluorescence spectra to those of the
anthocyanin and chlorophyll compounds [21].
The intensity of either excitation or emission signals of acetone extract was higher than those of the
ethanolic extract, which was in good agreement with the naked-eye observation as well as their UV-
Vis spectrum. These experiments serve a useful preliminary data for the optical properties of the
isolated natural pigments from purple mangosteen peels. Since both ethanolic and acetone extracts
show a remarkable fluorescence intensity, they are promising to be used as the photonic material
and/or dye-sensitizer agents in the near future.

600 600
(a) (b)

Fluorescence Intensity (a.u.)

Fluorescence Intensity (a.u.)

500 500

400 400

300 300

200 200

100 100

0 0
200 300 400 500 600 700 800 200 300 400 500 600 700 800
Wavelength (nm) Wavelength (nm)

Figure 6. The two-dimensional fluorescence spectra of the purple mangosteen peel extract in (a)
ethanol and (b) acetone. Dash line: excitation spectrum. Solid line: emission spectrum.

4. Conclusions
Isolation of the natural pigments from purple mangosteen peels has been successfully carried out
through a maceration technique employing distilled water, ethanol, and acetone as the solvents. From
the FTIR spectra, both distilled water and ethanolic extracts contained polar natural pigments, yielding
a pale yellow color, while the acetone extract contained non-polar natural pigments, giving stronger
yellow color intensity than those of the distilled water and ethanolic extracts. The UV-Vis spectra of
the extracts revealed that the isolated natural pigments were dominated by mangosteen, anthocyanin
and phenolic acid compounds. While the distilled water extract gave no remarkable fluorescence
signal, the acetone extract gave the highest fluorescence intensity in which agreed well with the naked-
eye observation and UV-Vis spectrum analysis.

Acknowledgement
The authors appreciate the financial support from Directorate General of Strengthening Research and
Development, Ministry of Research, Technology and Higher Education of the Republic of Indonesia
via the Higher Education Excellent Applied Research scheme (PTUPT 2019, No.
041/SP2H/LT/MULTI/L7/2019 and No. 005/MACHUNG/LPPM/SP2H-LIT-MULTI/III/2019).

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IOP Conf. Series: Materials Science and Engineering 833 (2020) 012018 doi:10.1088/1757-899X/833/1/012018

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