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Oriental Journal of Chemistry


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India  -  SIR Ranking of India

Biochemistry, Genetics and Molecular Biology


Biochemistry
18
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Environmental Science
Environmental Chemistry

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Drug Discovery

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ISSN 0970020X, 22315039

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1/16/2020 Oriental Journal of Chemistry

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Biochemistry
comprises the quarter of the journals with the highest values, Q2 (yellow) the second highest values, Q3 (orange) the third
highest values and Q4 (red) the lowest values.
Chemistry (miscellaneous)

CategoryDrug Discovery Year Quartile


Biochemistry 2009 Q4
Biochemistry
Environmental Chemistry 2010 Q4
Biochemistry 2011 Q4
Biochemistry 20092012 2010
Q4 2011 2012 2013 2014 2015 2016 2017 2018

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The
0.3SJR is a size-independent prestige indicator that This indicator counts the number of citations received by
0.8
ranks journals by their 'average prestige per article'. It is documents from a journal and divides them by the total
based on the idea that 'all citations are not created
0.225 number of documents published in that journal. The
equal'. SJR is a measure of scienti c in uence of chart shows the evolution of the average number of
0.15 0.6
journals that accounts for both the number of citations times documents published in a journal in the past two,
received by a journal and the importance or prestige of three and four years have been cited in the current year.
0.075
the journals where such citations come from It The two years line is equivalent to journal impact factor
measures
2009
the scienti
2011
c in uence
2013
of the2015
average article
2017
™ (Thomson Reuters) metric.
0.4
in a journal it expresses how central to the global

Total Cites Self-Cites Cites per document Year Value


Cites / Doc. (4 years) 2008
0.2 0.000
800 Cites / Doc. (4 years) 2009 0.096
Evolution of the total number of citations and journal's
self-citations received by a journal's published Cites / Doc. (4 years) 2010 0.183
documents during the three previous years. Cites / Doc. (4 years) 2011 0.167
0
Cites / Doc. (4 years) 2012 0.428
400
Journal Self-citation is de ned as the number of citation
from a journal citing article to articles published by the Cites / Doc. (4 years) 2013 0.498
2008 2010 2012 2014 2016 2018
same journal.
Cites / Doc. (4 years) 2014 0.456
Cites / Doc.
Cites / Doc.(4
(4years)
years) 2015 0.463
0 Cites / Doc. (3 years)
Cites / Doc. (4 years) 2016 0.607
Cites
2008 Year
2010 Value
2012 2014 2016 2018 Cites
Cites / Doc.(4
/ Doc. (2years)
years) 2017 0.608
S lf Cit 2008 0
External Cites per Doc Cites per Doc % International Collaboration

Evolution of the number of total citation per document


0.8 International Collaboration accounts for the articles that
21
and external citation per document (i.e. journal self- have been produced by researchers from several
citations removed) received by a journal's published countries. The chart shows the ratio of a journal's
14
0.4
documents during the three previous years. External documents signed by researchers from more than one
citations are calculated by subtracting the number of 7
country; that is including more than one country address.
self-citations from the total number of citations received
0 0
by the journal’s documents. Year International Collaboration
2008 2010 2012 2014 2016 2018 2008
2008 1.60 2010 2012 2014 2016 2018
Cit Y V l 2009 1 89
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https://www.scimagojr.com/journalsearch.php?q=11900154394&tip=sid&clean=0 2/5
ISSN: 0970-020 X
ORIENTAL JOURNAL OF CHEMISTRY CODEN: OJCHEG
An International Open Access, Peer Reviewed Research Journal
2019, Vol. 35, No.(5):
Pg. 1579-1583
www.orientjchem.org

Rapid Identification of Anthocyanin in Ficus aurata Fruits by


Liquid Chromatography-Mass Spectrometry Approach
Daimon Syukri*, Ismed, Vioni Derosya, Ririn Fatma Nanda
and Dosmawarni Indah Gultom

Faculty of Agricultural Technology, Andalas University, Limau Manis, Padang, West Sumatera,
25163, Indonesia.
*Corresponding author E-mail: dsyukri@ae.unand.ac.id

http://dx.doi.org/10.13005/ojc/350516

(Received: September 03, 2019; Accepted: October 01, 2019)

Abstract

The aim of this study was to identify the chemical structure of anthocyanins in the fruits of
Ficus aurata. The anthocyanin was detected and characterized using the liquid chromatography
system with UV-Vis detection tandem triple quadrupole mass spectrometer. After UV-Vis detection,
the characterization of anthocyanin was subjected to a triple quadrupole system of mass spectrometer.
The precursor ions of anthocyanidins (cyanidin, delphinidin, malvidin, pelargonidin, petunidin,
and peonidin) were scanned to identify the distinctive particular anthocyanin. Then, the detected
anthocyanins was further confirmed and their isomers such as glycosides and galactosides forms
were distinguished by the fragmentation pattern on production analysis scan after comparison with
mass spectroscopy online databases. For the first time, it had characterized that in the fruits of
Ficus aurata contains at least seven kinds of anthocyanins with all possible combinations of three
anthocyanidins.

Keywords: Ficus aurata, Mass spectrometry, Structure conformation, Triple quadrupole.

INTRODUCTION Many plants are being discovered as


the natural source of anthocyanin where each of
Anthocyanin is a class of phenolic compounds them is showing the attractive color from their peel
that cause certain colors (blue, purple and red) in such as grape, strawberry, apple, berries and etc9.
natural products1,2. Since the few last decades, there Meanwhile, there is a fruit which has no specific
have been an increasing attention in anthocyanins attractive color, namely Ficus aurata, yet might
research due to its benefits on potential health effect has a potential as an anthocyanin source since
on human being other than attractive food colorant. its seed has a strong specific anthocyanin’s color.
There are many reports indicated the health beneficial Ficus aurata is a variety of ficus or fig species that
effects of anthocyanins such as antioxidative3,4,5, is very commonly seen along the roadside in the
anti-inflammatory and anti-obesity6, DNA cleavage7 Andalas University, Indonesia, in which it gives great
and cardiovascular protective properties8. contribution to the forest ecosystem.

This is an Open Access article licensed under a Creative Commons license: Attribution 4.0 International (CC- BY).
Published by Oriental Scientific Publishing Company © 2018
Syukri et al., Orient. J. Chem., Vol. 35(5), 1579-1583 (2019) 1580

When it is ripe, Ficus aurata can acquire herbarium identification laboratory of Andalas
coloring seed hues to dark-violet that might due to University (Identification Number: 101/K-ID/ANDA/
the presence of high amount of anthocyanin (Fig.1). III/2019). The fruits of Ficus aurata were sampled
We suggest, due to the lack of striking color form at the botanical garden of Andalas Univesiry and
the peel of Ficus aurata, make this fruit has not immediately transported to laboratory for analysis.
recognized as a potential source of anthocyanin.
Chemicals
Methanol, acetonitrile and water (LC
MS grade) were purchased from J. T. Baker
(Baker Mallinckrodt, Phillipsburg, NJ, USA).
Methanol, acetonitrile, formic acid (LC grade) were
purchased from Smart Lab (SMART-LAB, Tangerang,
Indonesia). Pro analysis grade hidrochloric acid was
also purchased form Smart Lab (SMART-LAB,
Tangerang, Indonesia).
Fig.1. The fruits of Ficus aurata

The objective of this study was to identify The extraction process of anthocyanins
the anthocyanin in the fruits of the Ficus aurata A 100 g of fruits has cut into small pieces
because there is no information available for this till and put into 1000 mL erlenmeyer flask then acidified
date. Many analytical techniques are applicable for methanol (pH 1.5) was added to the flask. The
anthocyanins characterization in natural products. extraction of anthocyanins were done by maceration
However, the most popular techniques is liquid technique at room temperature for 12 h in a absence
chromatography with multiple UV-Vis detection using of light. This step was conducted three times.
photodiode-array detector (LC UV-Vis) combined Furthermore, the extract was concentrated using a
with mass spectrometry (MS) detection10. Although rotary evaporator. About 5 mL of concentrated extract
the utilization of LC UV-Vis especially in the range was then filtered passed through a 0.2 μm millipore
of wavelength from 500 to 550 nm has already filter for subsequent analysis.
known as general condition for identification of
HPLC UV-Vis and LC MS/MS analysis
anthocyanin in natural product mixtures, however
The anthocyanins in the fruits of Ficus
this kind of method cannot produce very accurate
aurata was separated in reverse phase liquid
results. This detection only indicate the presence
chromatography and subsequent identified and
of the red-violet colors as representative of normal
characterized using an photodiode array detector
anthocyanin without any consideration of various
and a MS/MS detector as describes on Syukri
forms of anthocyanins11.
et al., 201414 and Syukri et al., 201815 with some
Moreover, since the anthocyanins modifications, respectively. The utilization of
derivatives have classified as class-targeted simultaneous detection modes in triple quadrupole
metabolite, the use of MS detection with triple ion trap mass spectrometer such as precursor ion
quadrupole system permits an ideal platform to scan, multiple and product ion scan were considered
produce more accurate analyses of anthocyanin and proposed to get a rapid, sensitive and accurate
down to low-level and establishment any kind of data of anthocyanin qualitatively in this study.
anthocyanin derivatives structure up to oxidation
nor various forms that exhibit no absorbance in the A high performance liguid chromatography
range from 500 to 550 nm through determination (HPLC) series system (Prominence HPLC 20
of specific molecular mass and subsequent its ion series Shimadzu, Kyoto, Japan), and a reverse-
fragmentations12,13. phase chromatographic column (a Zorbax SB-
C18, 150 mm×3.0 mm i.d., 5 μm in particle size,
EXPERIMENTAL agilent, Canada, USA) coupled to a DAD detector
(Prominence SPD-M20A) were used for HPLC
Materials Plant material UV-Vis analysis. The mobile phases were (A) 1%
The Ficus aurata was identified at of formic acid in water and (B) 50% of acetonitrile
Syukri et al., Orient. J. Chem., Vol. 35(5), 1579-1583 (2019) 1581

in water containing 1% formic acid. The separation and 550 nm, respectively). There were two peaks
of anthocyanin in the sample was eluted based on observed at those wavelengths. The highest peak
the step gradient polarity separation as described intensity of the peak was observed at a wavelength
in Table 1. The detection wavelengths on UV-Vis of 520 nm. Primary anthocyanin was detected at RT
were in the range of 500 to 550 nm. The extract 11.8 min while the second ones was detected at
samples were injected as 5 μL. Moreover, for RT 10.8 minute. Such detection can be used to
LC MS/MS, the anthocyanins were identified confirm anthocyanins in plant material samples16.
and characterization using a prominence HPLC However, referring to previous studies, most plant
20A Shimadzu, Kyoto, Japan that equiped with a material samples should contain more than two
reverse-phase chromatographic column (Unison anthocyanins16,17,18,19. Therefore, another analysis
UK-C8, 150 mm ×2.0 mm i.d., 3 μm in particle
such as mass spectrometry needs to be further
size, Imtakt, Kyoto, Japan). The LC was coupled to
carried out to obtain more comprehensive data on
a triple-quadrupole mass spectrometer (Q-TRAP
anthocyanins in the fruits of Ficus aurata.
4500 AB-Sciex, Framingham, MA, USA). The mobile
phases were 0.1% formic acid in water (solvent A)
and 0.1% formic acid in acetonitrile (solvent B). The
mobile phases were set on anthocyanin separation
similar as the LC UV-Vis detection at flow rate as
0.2 mL/minute. Anthocyanins were ionized using a
Turbo-V™ ion source in positive mode. Precursor
ion scan functions in AB- Sciex, QTRAP®, namely,
PSI scan followed by enhanced product ion (EPI)
scans, were used to study the fragmentation pattern
of anthocyanins in the Ficus aurata extraction solvent
that was separated in retention on a chromatographic
column. For mass spectroscopy scanning, the MS
was operated in positive polarity at a scan rate of
1000 Da/s within the mass range of 200–800 amu.
The MS parameters were set as follows: Collision
Energy Spread (CES) = 15, Declostiring Potential
(DP) = 45, Entrance Potential (EP) = 10, Curtain
gas (CUR) = 10 and Temperature (TEM) = 600. The
Fig. 2. HPLC UV-Vis chromatogram of anthocyanins in the
Analyst software version 1.5 was used to integrate
fruits of Ficus aurata
and analyze all detection component in this study.
Figure 3 indicates the precursor-ion
Table 1: The step gradient polarity program scan (PIS) chromatogram of anthocyanin in
for HPLC-anthocyanin identification
the fruit of Ficus aurata. The PIS analysis was
No Time (min) %B Flow (mL/min) conducted simultaneously for all precursors of six
anthocyanidins (aglycone) i.e. 287 for cyanidin, 303
1 0 6 1.2
for delphinidin, 331 for malvidin, 301 for peonidin,
2 4 10 1.2
3 12 25 1.2 271 for pelargonidin, and 317 for petunidin. It has
4 13 25 1.2 detected three precursor of anthocyanidins such as
5 20 40 1.2
cyanidin (287), pelargonidin (271) and delphinidin
6 35 60 1.2
7 40 100 1.2 (303) that formed in seven anthocyanins derivatives.
8 45 6 1.2 The major and the smallest were identified as
RESULT AND DISCUSSION a cyanidin anthocyanin while pelargonidin and
delphinidin anthocyanin were found in the moderate
Figure 2 shows the UV-Vis chromatogram level. This data can strengthen the previous UV-Vis
of the predicted anthocyanin in the methanol observation that indicate the presence of two kinds
extract from the fruits of Ficus aurata (λ = 500, 520 of anthocyanin in the fruits of Ficus aurata.
Syukri et al., Orient. J. Chem., Vol. 35(5), 1579-1583 (2019) 1582

as the major anthocyanin. Moreover, delphinidin


3-O-(6”-acetylglycoside), pelargonidin 3-glycoside,
delphinidin 3-O- galactoside, cyanidin 3-O-(6-O-
malonyl-β-D-glycoside), cyanidin 3-O-sophoroside
were identified as minor anthocyanins.

Fig. 3. The chromatogram of product ion scan anthocyanin


analysis in the fruits of Ficus aurata. Precursor of cyanidin,
m/z = 287 (A,B,E and G), Precursor of pelargonidin, m/z =
303 (D) and precursor of delphinidin, m/z = 303 (C and F)

Furthermore, the structural confirmation


of detected anthocyanin was conducted by the
enhanced product ion (EPI) analysis. Fig. 4 indicates
the EPI chromatogram of each detected anthocyanin
in the fruits of Ficus aurata. Each fragmentation
Fig. 4. Fragmentation mass spectra of each detected
was compared to the mass fragmentation of
anthocyanin after enhanced product ion analysis. cyanidin
common anthocyanins from online databases 3-glycoside (A); cyanidin 3-(6''-acetylglycoside) (B);
such as METLIN metabolomics databases and delphinidin 3-O-galactoside (C); pelargonidin 3-glycoside)
LIPIDMAPS. As the results, it can be proposed (D); cyanidin 3-O- (6-O- malonyl -β -D-glycoside) (E);
that the fruits of Ficus aurata contain cyanidin delphinidin 3-O-(6”-acetylglycoside)(F) and cyanidin 3-O-
3-glycoside and cyanidin 3-(6''-acetylglycoside) sophoroside (G)
Syukri et al., Orient. J. Chem., Vol. 35(5), 1579-1583 (2019) 1583

CONCLUSION anthocyanins in all possible combination of three


anthocyanidins were identified. This approach allows
The data described here demonstrating mass spectrometry to be a rapid identification method
the combination of UV-Vis detection, precursor-ion with high selectivity and accurate characterization of
analysis and product-ion analysis tandem mass anthocyanins whereas it could be possibly used as
spectrometer on liquid chromatography instrument
a general screening tool for identifying anthocyanins
for viable technique on the screening of anthocyanins
in plants for practical use.
in complex biological matrices rapidly. By employing
these techniques, the anthocyanins in the fruits
ACKNOWLEDGEMENT
of Ficus aurata could be identified and confirmed
only by an injection into the LC-MS/MS system and This work was financed by a grant from
without any standard needed. Thus, the efficiency
the Faculty of Agricultural Technology of Andalas
of time analysis in the identification of anthocyanin
University, Indonesia (01K/PL/DF-DIPA/FATETA-
was the main consideration in this study.
2019).
In addition, till date, there is no report
indicated the anthocyanin conformation in the fruits of
Ficus aurata, therefore, we describe the anthocyanins Conflict of Interests
in the fruits of Ficus aurata for the first time. In the The authors declare that there is no conflict
fruits of Ficus aurata, at least, there are seven of interests.
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