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B IOD I V E R S I TA S ISSN: 1412-033X

Volume 24, Number 7, July 2023 E-ISSN: 2085-4722


Pages: 3665-3672 DOI: 10.13057/biodiv/d240703

Chemical constituents and antioxidant activity of Britton's wild petunia


(Ruellia brittoniana) flower

GRACIA LASMA ROHANA SIANTURI1, ELYNA WAHYU TRISNAWATI1, MAMORU KOKETSU2,


VENTY SURYANTI1,♥
1Departmentof Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Sebelas Maret. Jl. Ir. Sutami 36A, Surakarta 57126, Central Java,
Indonesia. Tel/fax.: +62-271-669376, ♥email: [email protected]
2Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University. 1 -1 Yanagido, Gifu 501-1193, Japan

Manuscript received: 20 April 2023. Revision accepted: 3 July 2023.

Abstract. Sianturi GLR, Trisnawati EW, Koketsu M, Suryanti V. 2023. Chemical constituents and antioxidant activity of Britton's wild
petunia (Ruellia brittoniana) flower. Biodiversitas 24: 3665-3672. Britton's wild petunia or kencana ungu (Ruellia brittoniana), which
has purple flowers, is widely used as a decorative plant. Isolation and structure determination of the antioxidant compound of R.
brittoniana flower were carried out. Extraction was carried out by maceration, and compound isolation was conducted by column
chromatography. Structure elucidation was accomplished by FTIR, NMR, and MS Spectrometry. Apigenin (4',5,7-trihydroxyflavone)
was isolated from the B1 fraction using chloroform: methanol (10: 1) eluent. Fraction A1, obtained from elution by chloroform:
methanol (10: 0), consisted of 24 compounds. Two compounds were identified as 1-hexadecanol and 1-phenyl ethanone, which have
antioxidant properties of fraction A1. Fraction B2 was eluted by chloroform: methanol (10:1), consisting of 20 compounds. A compound
was identified as 2-methoxy phenol, contributing to the antioxidant properties of fraction B2. The total phenolic content of R.
brittoniana flower extract was 1.033 mg GAE/g, and its total anthocyanin content was 16.97%. Fractions A1 and B2 possessed strong
antioxidant activities due to their phenolic compounds. Apigenin has three -OH groups in the 4’, 5, and 7 positions; only the -OH group
at the 4’ position contributes to its antioxidant activity. Therefore, apigenin has moderate antioxidant activity by DPPH assay. The
modification structure of apigenin needs further study to enhance its antioxidant activity. This research shows that R. brittoniana flower
can be a source of apigenin, also known to have anticancer properties.

Keywords: Antioxidant activity, kencana ungu, Ruellia brittoniana, total anthocyanins content, total phenolics content

INTRODUCTION antioxidant, anti-hypertensive, analgesic, anti-inflammatory,


antidiabetic, and antipyretic properties (Khan et al. 2017).
Acanthaceae is a dicotyledonous flowering plant with Ruellia species are traditionally used to treat influenza,
over 250 genera and 2500 species (Matos et al. 2022). fever, and inflammation. The leaves of the R. prostrata
Some are epiphytes, while others are herbs, shrubs, or plant have been widely used in treating rheumatism,
twining vines. The Acanthaceae family is known for its eczema, and other skin diseases. Ruellia asperula is
diverse range of tropical and subtropical habitats. Several commonly used to treat bronchitis, asthma, influenza,
species are found in temperate areas (Khan et al. 2017). fever, and inflammation of the uterus. Ruellia hygrophila
Several species are widespread in Indonesia, Malaysia, has antispasmodic analgesic activity (Afzal et al. 2015).
Africa, Brazil, and Central America (Afzal et al. 2015; Ruellia tuberosa leaves are regularly used to treat
Khan et al. 2017; Matos et al. 2022). Some of these are gonorrhea, ear disease, skin diseases and to heal burns. The
plants with medicinal uses. The Acanthaceae family has dried roots of the R. tuberosa were used to treat eye and
been extensively utilized in Indonesian traditional bladder diseases (Chothani et al. 2010). R. tuberosa has
medicine. The genus has long been recommended to treat antimicrobial activity, antioxidant activity, anticancer and
diseases such as diabetes, high blood pressure, dermatitis, anti-inflammatory (Chothani et al. 2010; Arirudran et al.
asthma, fever, and bronchitis. It contains numerous 2011).
secondary metabolites with many therapeutic utilities, such Britton's wild petunia (Ruellia brittoniana), also known
as flavonoids, alkaloids, terpenoids, tannins, phenols, as kencana ungu (Indonesian), is a herbaceous ornamental
saponins, and quinones (Khan et al. 2017). Further study is perennial herb with a flowering period from April to
required to identify the active compounds in this genus November. It greatly tolerates dry and harsh conditions
responsible for their bioactivities to introduce them to the (Figure 1) (Khan et al. 2017). The purple blossom of R.
commercial health market and offer the community their brittoniana contains anthocyanins (Le et al. 2019).
potential benefits. Anthocyanins are natural water-soluble flavonoid pigments
Ruellia is a genus in the Acanthaceae family as a abundantly found in the vacuoles of plants' stems, flowers,
perennial and decorative plant. Many species of this genus fruits, and leaves (Tan et al. 2022). It has various colors of
contain essential constituents such as flavonoids, alkaloids, purple, red, violet, pink, and blue (Mohammed and Khan
triterpenoids, and glycosides. Ruellia plant extracts exhibit 2022). Anthocyanin has antioxidant activity due to
3666 B I OD I V E R S ITA S 24 (7): 3665-3672, July 2023

phenolate groups in its structure (Suryanti et al. 2020). R.


brittoniana shows various biological activities such as
anticancer, anti-microbes, anti-inflammatory, and antioxidant
activities (Afzal et al. 2015; Ahmad 2017). R. brittoniana
contains 5,2,3-trihydroxy 7-O-glucoflavone; 5,7,4-trimethoxy
3-O-Rhamnoflavone; and 2,2,4,6 -tetrahydroxy-calcone
(Khan et al. 2017). Several flavonoids, such as 2-O-α-D-
galactopyranosil glycerol hexaacetate; 5,2′,3′-trihydroxy-7-
O-glucoflavone; 5,7,4′- trimethoxy-3-O-ramnopyranoside;
and 2,2′,4′,6′-tetrahydroxy-chalcone, have been isolated
from the whole plant of R. brittoniana (Elgindi et al. 2015).
Antioxidant compounds are natural or synthetic
compounds that inhibit or delay oxidation at relatively low
Figure 1. Ruellia brittoniana flower
concentrations. Antioxidants interact with free radicals
before damaging host cells (Abeyrathne et al. 2022).
Antioxidant compounds in plants are β-carotene, ascorbic Column chromatography of ethyl acetate extract
acid, alkaloids, saponins and tannins, and phenolics, such The Friko 24/40 column was filled with 350 g of silica
as flavonoids, cinnamic acid derivates, coumarin, and gel slurry. Sea sand (15 g) was placed on top of the silica
tocopherols (Suryanti et al. 2016; Suryanti et al. 2021; gel. Ethyl acetate extract (8 g) was put on the packed
Suryanti et al. 2022). Phenolic compounds have a wide column. Gradient polarity of solvent was introduced using
range of structural, functional, and biological properties methanol, chloroform, and acetone with the composition as
(Abeyrathne et al. 2022). Phenolate compounds can follows, methanol: chloroform (10: 1), (5: 1), (5: 2) and
scavenge free radical compounds and inhibit singlet acetone (10:0). Eluted fractions were analyzed by thin layer
oxygen due to electron-donating groups such as the chromatography (TLC). The eluted fractions with similar
hydroxyl group. Modification structure of secondary Rf values were collected and evaporated. NMR
metabolites is often carried out to enhance their antioxidant Spectroscopy analyzed the single compound, while GC-MS
activity (Suryanti et al. 2018). Studies have analyzed the Spectroscopy analyzed the fractions.
phytochemical, antioxidant properties, and anticancer
activity of the R. brittoniana flower (Tejaputri et al. 2019; Total phenolics content (TPC) determination
Tejaputri et al. 2020). Meanwhile, isolation and structure TPC of flower extract was determined by the Folin-
identification of the R. brittoniana flower has never been Ciocalteu method (Tian et al. 2021). One mL of methanol
carried out. This paper discusses the isolation and structure extract (10 ppm) in aquadest was put into a glass vial.
determination of antioxidant active compounds of the R. Folin-Ciocalteu reagent (0.5 mL) was added and stirred for
brittoniana flower. 1 min. 7.5% of Na2CO3 solution was added and stirred
again for 1 min. The mixture was incubated at the maximum
time, and the UV-Vis spectrophotometer measured its
absorbance. The same procedure was used to examine
MATERIALS AND METHODS
gallic acid at concentrations of 2, 4, 6, 8, and 10 ppm for
standard curves of total phenolics content determination.
Study area
Total phenolic was calculated using equation (1), where C
R. brittoniana flowers were collected from the Faculty
is the concentration of gallic acid established from the
of Mathematics and Natural Sciences, Universitas Sebelas
calibration curve (mg/mL), V is the volume of extract
Maret, Surakarta, Indonesia. This study was conducted at
(mL), and m is the weight of the plant extract (g). TPC was
the Department of Chemistry, Faculty of Mathematics and
expressed as mg Gallic Acid Equivalent (GAE)/g sample.
Natural Sciences, Universitas Sebelas Maret, Surakarta,
Indonesia, and the Department of Chemistry and C×V
Biomolecular Science, Faculty of Engineering, Gifu 1 TPC=
m
(1)
University, Japan.
Total anthocyanins content (TAC) determination
Extraction of R. brittoniana flowers The pH differential method was used to determine the
The R. brittoniana flowers were macerated using TAC of flower extract (Jaafar et al. 2020). TAC was
methanol and evaporated to obtain methanol extract. The expressed as cyanidin-3-glucoside. Flower extract (0.05 g)
methanol extract was dissolved in aquadest (250 mL) and was added with 4 mL of KCl buffer solution pH = 1, and
transferred into a separating funnel. Hexane (250 mL) was the mixture was then incubated for 2 h, followed by
added to the solution to obtain the hexane and water centrifugation at 150 rpm for 1 min. The supernatant was
fractions. The water fraction was then re-fractioned using measured with a UV-Vis spectrophotometer at 520 and 700
ethyl acetate. The ethyl acetate fraction was evaporated to nm. The same procedures were conducted for CH3COONa
obtain ethyl acetate extract, and further purification of ethyl buffer solution pH = 4.5. Absorbance data was introduced
acetate extract was conducted by column chromatography. into equation (2), where A520 is the absorbance at 520 nm,
and A700 is the absorbance at 700 nm.
SIANTURI et al. – Chemical compounds and antioxidant activity of Ruellia brittoniana flower 3667

A = (A520-A700)pH1 - (A520 -A700)pH4.5 (2) was expected to exhibit good antioxidant activity. Ethyl
acetate extract of R. brittoniana flower was originally
TAC value was determined by equation (3), where A is purple colored and turned into light pink or pink when
the absorbance from eq. (2), Ɛ is 30175 M, l is the path reacted with CH3COONa and KCl buffer solution.
length (cm), Mw is the molecular weight of cyanidin-3- There are three types of anthocyanin structures:
glucoside (611 g/mol), DF is the dilution factors, V is the cyanidin, pelargonidin, and delphinidin for dark red/pink,
volume (mL), W is the weight of samples (g). bright red/orange, and blue/violet/purple, respectively
(Inggrid et al. 2016). These types of anthocyanin structures
A V can be distinguished from the number of hydroxyl groups
1 TAC= ×Mw×DF× ×100 % (3)
Ɛ×l W attached to the parent compound. The number of -OH
groups in anthocyanins indicates their potential as
antioxidants (Le et al. 2019). The distinctive purple color
Antioxidant activities assay of the R. brittoniana flower indicates the presence of
Antioxidant activity of the sample was determined by anthocyanin pigments. The total anthocyanins content
the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method (Sethi et (TAC) of ethyl acetate extract was 16.97%. The purple
al. 2020). The sample was diluted with methanol to obtain color of the R. brittoniana flower indicates that the
5, 10, 15, 20, and 25 ppm concentrations. Each sample was extracted anthocyanins were delphinidin. It is the most
added 1 mL of DPPH 0.2 mM solution and then incubated polar anthocyanin, with three phenolic hydroxy groups in
for 30 mins before being measured with the UV-Vis the B ring in the molecular structure. The ortho-
spectrophotometer at the maximum wavelength determined dihydroxyphenyl structure at the B-ring appears essential
by measuring DPPH 100 ppm solution at 800-400 nm. The for its bioactivity properties. Delphinidin has an inhibitory
same procedure was conducted for Vitamin E as a positive effect on the growth of human vulva carcinoma cell line
control. Antioxidant activities were determined by A431 in vitro, uterine carcinoma (HeLa S3 cells), and
measuring % inhibition using equation (4), where An is the colon adenocarcinoma cells (CaCo-2 cells) (Jing and Giusti
negative control's absorbance, and As is the samples' 2010).
absorbance. The IC50 was calculated by interpolation and Column chromatographic of ethyl acetate extracts
plotting the correlation between each concentration and its resulted in 8 fractions, i.e., fractions A1, A2, B1, B2, C1,
scavenging percentage. The effective concentration of each C2, C3, and D1. The weight of the B1 fraction was 0.05 g
extract, which scavenges 50% of DPPH radicals, was used of yellow powders and showed a single spot-on TLC, and
to measure the antioxidant activity, which was expressed as FT-IR, NMR, and MS Spectrophotometry determined its
the IC50 value. structure. The weight of the green powder of the A1 and B2
fractions were 0.12 and 0.03 g, respectively. TLC plates of
(4) both fractions showed many spots on TLC; therefore, they
were subjected to GC-MS analysis. Since other fractions
Data analysis were obtained very small amounts, no further analyses
The single spot eluted fraction on the TLC plate was were subjected to GC-MS analysis.
recognized as a pure compound. FTIR, NMR, and MS FT-IR spectrum of B1 fraction showed the broad peak
Spectrometry were used to identify the single spot. MS of the hydroxyl group at 3500-3300 cm-1 (Figure 2). Peaks
analysis was conducted using electron impact ionization of aromatic were found at 3030-3150 cm-1 for CH
and 50 scans. The multiple spots eluted fractions were (stretching), 1466 cm-1 for C=C (stretching) and 1605 cm-1
subjected to GC-MS analysis with column type Rtx 5 MS for C=C (bending). The carbonyl group peak was found at
30 m in length with helium gas as the carrier. The oven 1735 cm-1, and the C-O group of ester peak was found at
temperature was 70°C, and the injection temperature was 1297 cm-1 (Peng et al. 2016; Shoubaky et al. 2016).
300°C with split-less mode injection at 13.7 kPa. Total The B1 fraction was dissolved in DMSO-d6 solvent for
1
phenolics, total anthocyanins, and antioxidant activity of H and 13C NMR Spectroscopy analyses (Table 1 and 2).
1
samples were determined. H NMR of B1 fraction showed 8 peaks with 10 protons in
total. The peak of the -OH group as a chelate was found at
12.96 ppm. Two other broad and low-intensity peaks of the
RESULTS AND DISCUSSION -OH group were found at 10.79 and 10.3 ppm. Aromatic
peaks of -CH were found at 6.1-8.5 ppm. Three multiplet
Chemical compounds determination peaks were found at 7.2-7.5 ppm, which were
The Folin-Ciocalteu technique was used to determine characteristics of meta disubstituted aromatic. Two doublet
the total phenolic content (TPC) of ethyl acetate extract peaks were found at 6.48 and 6.16 ppm, characteristic of
(Çayan et al. 2022). The TPC of ethyl acetate extract was para disubstituted aromatic (Peng et al. 2016). 13C NMR of
3.84 mg GAE/g. Phenolic compounds possess a chemical the B1 fraction showed 13 peaks with 15 protons in total. A
structure comprising an aromatic ring with one or more characteristic peak of the carbonyl group of esters was
hydroxyl substituents. The main groups of phenolic found at 182.28 ppm. Characteristic peaks of quaternary
compounds are flavonoids, phenolic acids, tannins, carbon and C-O groups were found at 164.70, 164.31,
stilbenes, and lignans (Machmudah et al. 2017). Phenolic 162.00, 161.74, and 157.86 ppm. Two peaks at 129.14 and
content is responsible for bioactivity; therefore, this extract 116.55 ppm showed the integration of two carbon atoms.
3668 B I OD I V E R S ITA S 24 (7): 3665-3672, July 2023

Three aromatic CH group peaks were found at 104.33, contributes to antioxidant activities (Chen et al. 2020;
100.02, and 94.61 ppm (Peng et al. 2016). Santos and Silva 2020). The 1-hexadecanol had 0.41% of
Two-dimensional NMR, including COSY, HMQC, and the total percent area with a retention time (RT) of 50.142
HMBC, were performed to determine the correlation mins. The 1-phenyl ethenone had 0.45% of the total
between 1H NMR and 1H NMR, 1H NMR, and 13C NMR percent area with an RT of 12.849 mins.
(Table 3). B1 fraction was identified as Apigenin or 4’,5,7- GC-MS analysis of the B2 fraction showed 20 peaks
trihydroxyflavone (Figure 3). Two-dimensional NMR (Figure 8). One compound was successfully identified as 2-
correlation of apigenin is shown in Figure 4. MS analysis methoxy phenol, which had a conjugate double bond and a
of the B1 fraction was performed using EI ionization hydroxyl group (Figure 9). The 2-methoxy phenol had
(Figure 5), which showed base peak of apigenin in the area 2.62% of percent total area with RT of 13.501 mins.
of m/z 270.0366 (Shoubaky et al. 2016; Dou et al. 2020).
The MS data confirmed that apigenin was the isolated Antioxidant activity
compound. Apigenin is a bioflavonoid compound The antioxidant activity (IC50) of samples was
(specifically a flavone) that is found in a wide variety of measured by the DPPH method (Table 4). Antioxidants
plants and herbs. Surprisingly, apigenin has never been scavenge DPPH radicals by donating hydrogen atoms
isolated from any genus of the Acanthaceae family. resulting in a yellow-colored non-radical state (Akter et al.
Apigenin from Tripleurospermum disciforme has been 2019). A decrease in absorbance and color change of the
isolated with a similar extraction process and similar sample solution from purple to yellow confirmed that the
characteristics of NMR data (Tofighi et al. 2015). This sample has antioxidant activity. All samples showed very
result indicated that R. brittoniana flower could be a source strong antioxidant activity except for apigenin which
of apigenin. Apigenin-rich foods are chamomile, celery, showed moderate antioxidant activity. Ethyl acetate had the
parsley, vine spinach, artichokes, and oregano (Shankar et highest antioxidant activity, followed by B2 and A1
al. 2017). fractions. Ethyl acetate extract, fractions A1 and B2 of R.
GC-MS chromatogram of A1 fraction showed 24 peaks brittoniana flower extract, possessed very strong
(Figure 6), and two compounds were identified as 1- antioxidant activities due to the synergic work of
hexadecanol and 1-phenyl ethenone or acetophenone compounds in enhancing their antioxidant activity.
(Figure 7). The 1-hexadecanol has a hydroxyl group and
the 1-phenyl ethenone has a conjugate double bond that

Figure 2. FTIR spectrum of B1 fraction


SIANTURI et al. – Chemical compounds and antioxidant activity of Ruellia brittoniana flower 3669

Table 1. 1H NMR data of B1 fraction

δ Multiplicity, integration,
Proton type
(ppm) position, and J coupling (Hz)
12.96 OH5 Chelator OH group
10.79 OH4’ OH
10.3 OH7 OH
7.91 d, 2H, H3' and H5‘, J = 8 Hz Aromatic CH
6.91 d, 2H, H2' and H6‘, J = 8 Hz Aromatic CH
6.74 s, 1H, H3 Aromatic CH
6.48 d, 1H, H6, J = 2 Hz Aromatic CH
Figure 3. Structure of Apigenin 6.16 d, 1H, H8, J = 2 Hz Aromatic CH

Table 2. 13C NMR data of B1 fraction

δ (ppm) Multiplicity, integration, position Carbon type


182.28 s, C4 Carbonyl
164.7 s, C7 C-O
164.31 s, C2 Aromatic C
162 s, C5 C-O
161.74 s, C8a Aromatic C
157.86 s, C4' C-O
129.14 s, 2C, C3' and C5' Aromatic CH
121.72 s, C2a Aromatic C
116.55 s, 2C, C2' and C6' Aromatic CH
Figure 4. The two-dimensional NMR correlation of apigenin 104.33 s, C3 Aromatic CH
103.36 s, C4a Aromatic C
100.02 s, C8 Aromatic CH
TPC and TAC of ethyl acetate extract showed that the
94.61 s, C6 Aromatic CH
extract possessed phenolic and anthocyanin compounds,
which play significant roles in antioxidant activities (Sethi
et al. 2020). Ethyl acetate extract contains many active Table 3. Table of correlation between 1H NMR and 1H NMR, 1H
compounds contributing to the high antioxidant activity NMR, and 13C NMR based on COSY, HMQC, and HMBC NMR
value. The A1 and B2 fraction contained 24 and 20
compounds, respectively, contributing to their antioxidant COSY NMR HMQC NMR HMBC NMR
activities. Antioxidant activity was enhanced with the δH δH δH δC δH δC
presence of functional groups, such as -OH, heterocyclic, (ppm) (ppm) (ppm) (ppm) (ppm) (ppm)
conjugated double bond, and electron donating group, 7.87 6.9 7.91 129.14 7.91 129.14
which attached in the ortho or para position toward 6.91 116.55 164.31
6.74 104.33 6.91 116.55
phenolic compounds (Lee et al. 2015; Akter et al. 2019). 6.48 94.61 6.74 103.36
Functional groups of compounds that enhanced antioxidant 6.16 100.02 6.48 100.02
activities were found in both fractions. The 1-hexadecanol 6.16 103.36
has a hydroxyl group, and the 1-phenyl ethenone has a 94.61
conjugate double bond contributing to antioxidant activities 104.33
(Chen et al. 2020; Santos and Silva 2020). The 2-methoxy 162.00
phenol has a conjugate double bond and a hydroxyl group.

Figure 5. MS spectrum of B1 fraction


3670 B I OD I V E R S ITA S 24 (7): 3665-3672, July 2023

Figure 6. GC-MS chromatogram of A1 fraction

Figure 7. Structure of 1-hexadecanol (left) and 1-phenyl ethenone (right)

Figure 8. GC-MS chromatogram of B2 fraction

Table 5. IC50 value of antioxidant activities of samples and


positive control

Sample IC50 (ppm) Category


Ethyl acetate extract 16.62 Very strong
A1 fraction 22.28 Very strong
Figure 9. Structure of 2-methoxy phenol B2 fraction 20.12 Very strong
Apigenin 109.24 Moderate
Vitamin E 11.50 Very strong

Apigenin possessed moderate antioxidant activity with C5-OH; hence the hydrogen atom transfer activity of C4’-
an IC50 value is 109.24 ppm. A previous study by Seyoum OH was strongest in scavenging free radicals DPPH. The -
et al. (2006) showed that apigenin also had moderate OH groups at positions 5 and 7 do not support much
antioxidant activity. The -OH groups of 3’ and 4’ positions antioxidant activity because they form intramolecular
in the B ring of flavonoids enhance its antioxidant activity. hydrogen bonds with adjacent carbonyl (Chen et al. 2022).
Apigenin has three -OH groups in the 4’, 5, and 7 positions. Therefore, apigenin only possessed moderate antioxidant
However, only the -OH group at the 4’ position contributes activity despite three -OH groups in its structure. Apigenin
to apigenin antioxidant activity. The bond dissociation is a type of flavonoid with good medicinal properties. It is
enthalpy of C4’-OH is most negligible than C7-OH and abundant in various fruits, vegetables, and medicinal
SIANTURI et al. – Chemical compounds and antioxidant activity of Ruellia brittoniana flower 3671

plants. Apigenin has been utilized as a dietary supplement Elgindi MR, Hagag EG, Mohamed SE. 2015. Phytochemical and
biological studies of Ruellia brittoniana. Res J Pharm Biol Chem Sci
due to its anticancer properties and anti-inflammatory and 6 (2): 926-933.
antioxidation activities. Apigenin exhibits anticancer Inggrid HM, Jaka, Santoso H. 2016. Natural red dyes extraction on roselle
activity with low cytotoxicity and no mutagenic activity in petals. IOP Conf Ser: Mater Sci Eng 162: 012029. DOI:
numerous human cancer cells, such as breast cancer, 10.1088/1757-899X/162/1/012029.
Jaafar NF, Ramli ME, Salleh RM. 2020. Optimum extraction condition of
prostate cancer, and colon carcinoma (Liu et al. 2013).
Clitorea ternatea flower on antioxidant activities, total phenolic, total
Modifications of apigenin have been made as the lead flavonoid and total anthocyanin contents. Trop Life Sci Res 31 (2): 1-
compound in anticancer drugs. Structural-activity relationship 17. DOI: 10.21315/tlsr2020.31.2.1.
(SAR) studies indicate that the A and C rings of Apigenin Jing P, Giusti MM. 2010. Contribution of Berry Anthocyanins to Their
Chemopreventive Properties. In: Stroner GD, Seeram NP (eds).
are suitable for various modifications (Chen et al. 2023). Berries and Cancer Prevention. Springer, New York.
In conclusion, isolated compound from R. brittoniana Khan I, Jan SA, Shinwari ZK, Ali M, Khan Y, Kumar T. 2017.
flower (B1 fraction) was identified as apigenin (4',5,7- Ethnobotany and medicinal uses of folklore medicinal plants
trihydroxyflavone). Apigenin has never been isolated from belonging to family Acanthaceae: An updated review. MOJ Biol Med
1 (2): 34-38. DOI: 10.15406/mojbm.2017.01.00009.
any genus of the Acanthaceae family. Fraction A1 consisted Liu R, Zhang H, Yuan M, Zhou J, Tu Q, Liu JJ, Wang J. 2013. Synthesis
of 24 compounds, with two compounds identified as 1- and biological evaluation of apigenin derivatives as antibacterial and
hexadecanol and 1-phenyl ethanone. Fraction B2 consisted antiproliferative agents. Molecules 18 (9): 11496-11511.
of 20 compounds, and a compound was identified as 2- DOI: 10.3390/molecules180911496.
Le XT, Huynh MT, Pham TN, Than VT, Toan TQ, Bach LG, Trung NQ.
methoxy phenol. The flower of R. brittoniana extract had
2019. Optimization of total anthocyanin content, stability and
total phenolic content of 1.033 mg GAE/g and total antioxidant evaluation of the anthocyanin extract from Vietnamese
anthocyanin content of 16.97%. Ethyl acetate extract Carissa carandas L. fruits. Processes 7: 468. DOI: 10.3390/pr7070468.
possessed strong antioxidant activity, with an IC50 value of Lee CY, Nanah CN, Held RA, Clark AR, Huynh UG, Maraskine MC,
Uzarski RL, McCracken J, Sharma A. 2015. Effect of electron
16.62 ppm. Fraction A1 and B2 possessed strong
donating groups on polyphenol-based antioxidant dendrimers.
antioxidant activity, with IC50 values were 22.28 and 20.12 Biochimie 111: 125-134. DOI: 10.1016/j.biochi.2015.02.001.
ppm, respectively; meanwhile, apigenin possessed moderate Machmudah S, Wahyudiono, Kanda H, Goto M. 2017. Hydrolysis of
antioxidant activity, with an IC50 value of 109.24 ppm. Biopolymers in Near-Critical and Subcritical Water. In: González
HD, Muñoz JG (eds). Water Extraction of Bioactive Compounds.
Elsevier. DOI: 10.1016/B978-0-12-809380-1.00003-6.
Matos P, Batista MT, Figueirinha A. 2022. A review of the
ACKNOWLEDGEMENTS ethnomedicinal uses, chemistry, and pharmacological properties of
the genus Acanthus (Acanthaceae). J Ethnopharmol 293: 115271.
DOI: 10.1016/j.jep.2022.115271.
The author would like to thank Universitas Sebelas Mohammed HA, Khan RA. 2022. Anthocyanins: Traditional uses,
Maret, Surakarta, Indonesia for financial support through structural and functional variations, approaches to increase yields and
research number 228/UN27.22/PT.01.03/2023. product’s quality, hepatoprotection, liver longevity, and commercial
products. Intl J Mol Sci 23 (4): 2149. DOI: 10.3390/ijms23042149.
Peng H, Zhang X, Xu J. 2016. Apigenin-7-O-β-d-glycoside isolation from
the highly copper-tolerant plant Elsholtzia splendens. J Zhejiang Univ
REFERENCES Sci B 17 (6): 447-454. DOI: 10.1631/jzus.B1500242.
Shankar E, Goel A, Gupta K, Gupta S. 2017. Plant flavone apigenin: An
Abeyrathne ED, Nam K, Huang X, Ahn DU. 2022. Plant- and animal- emerging anticancer agent. Curr Pharmacol Rep 3 (6): 423-446. DOI:
based antioxidant’s structure, efficacy, mechanisms and applications: 10.1007/s40495-017-0113-2.
A review. Antioxidants 11 (5): 1025. DOI: 10.3390/antiox11051025. Santos CMM, Silva AMS. 2020. The antioxidant activity of
Afzal K, Uzair M, Chaudhary BA, Ahmad A, Afzal S, Saadulah M. 2015. Prenylflavonoids. Molecules 25: 696. DOI: 10.3390/molecules25030696.
Genus Ruellia pharmacological, phytochemical importance in Sethi S, Joshi A, Arora B, Bhowmik A, Sharma RR, Kumar P. 2020.
ethnopharmacology. Acta Pol Pharm Res 72 (5): 821-827. Significance of FRAP, DPPH, and CUPRAC assays for antioxidant
Ahmad AR, Elya B, Mun’im A. 2017. Antioxidant activity and isolation activity determination in apple fruit extracts. Eur Food Res Technol
of xanthine oxidase inhibitor from Ruellia tuberosa L. leaves. 246 (3): 591-598. DOI: 10.1007/s00217-020-03432-z.
Pharmacogn J 9 (5): 607-610. DOI: 10.5530/pj.2017.5.96. Seyoum A, Asres K, El-Fiky FK. 2006. Structure-radical scavenging
Akter J, Hossain MA, Takara K, Islam MZ, Hou DX. 2019. Antioxidant activity relationships of flavonoids. Phytochemistry 67 (18): 2058-
activity of different species and varieties of turmeric (Curcuma spp.): 2070. DOI: 10.1016/j.phytochem.2006.07.002.
Isolation of active compounds. Comp Biochem Physiol Part C Shoubaky GAEl, Abdel-Daim MM, Mansour MH, Salem EA. 2016.
Toxicol Pharmacol 215: 9-17. DOI: 10.1016/j.cbpc.2018.09.002. Isolation and identification of a flavone apigenin from marine red alga
Çayan F, Tel-Çayan G, Deveci E, Duru ME, Öztürk M. 2022. Isolation Acanthophora spicifera with antinociceptive and anti-inflammatory
and identification of compounds from truffle Reddellomyces activities. J Exp Neurosci 10: JEN.S25096. DOI:
westraliensis and their antioxidant, cytotoxic and enzyme inhibitory 10.4137/JEN.S25096.
activities. Process Biochem 121: 553-562. DOI: Suryanti V, Marliyana SD, Putri HE. 2016. Effect of germination on
10.1016/j.procbio.2022.08.001. antioxidant activity, total phenolics, β-carotene, ascorbic acid and β-
Chen J, Yang J, Ma L, Li J, Shahzad N, Kim CK. 2020. Structure- tocopherol contents of lead tree sprouts (Leucaena leucocephala
antioxidant activity relationship of methoxy, phenolic hydroxyl, and (LMK.) de Wit). Intl Food Res J 23 (1): 167-172.
carboxylic acid groups of phenolic acids. Sci Rep 10 (1): 2611. DOI: Suryanti V, Wibowo FR, Khotijah S, Andalucki N. 2018. Antioxidant
10.1038/s41598-020-59451-z. activities of cinnamaldehyde derivatives. IOP Conf Ser: Mater Sci
Chen B, Su J, Hu Y, Liu S, Ouyang X, Cai R, You X, Li X. 2023. Eng 333: 012077 DOI: 10.1088/1757-899X/333/1/012077.
Antioxidant mechanisms and products of four 4′,5,7- Suryanti V, Kusumaningsih T, Marliyana SD, Setyono HA, Trisnawati
trihydroxyflavonoids with different structural types. RSC Med Chem EW. 2020. Identification of active compounds and antioxidant
14 (1): 173-182. DOI: 10.1039/D2MD00333C. activity of teak (Tectona grandis) leaves. Biodiversitas 21 (3): 941-
Dou X, Zhou Z, Ren R, Xu M. 2020. Apigenin, flavonoid component 947. DOI: 10.13057/biodiv/d210313.
isolated from Gentiana veitchiorum flower suppresses the oxidative Suryanti V, Marliyana SD, Rohana GL, Trisnawati EW, Widiyanti. 2021.
stress through LDLR-LCAT signaling pathway. Biomed Bioactive compound contents and antioxidant activity of fermented
Pharmacother 128: 110298. DOI: 10.1016/j.biopha.2020.110298. lead tree (Leucaena Leucocephala (Lmk.) De Wit) seeds. Molekul
16(3): 192-199. DOI: 10.20884/1.jm.2021.16.3.756
3672 B I OD I V E R S ITA S 24 (7): 3665-3672, July 2023

Suryanti V, Sariwati A, Sari F, Handayani DS, Risqi HD. 2022. Tejaputri NA, Arsianti A, Qorina F, Fithrotunnisa Q, Azizah NN,
Metabolite bioactive contents of Parkia timoriana (DC) Merr seed Putrianingsih R. 2020. Anticancer activity of Ruellia britoniana
extracts in different solvent polarities. Hayati 29 (5): 681-694 DOI: flower on cervical HeLa cancer cells. Pharmacogn J 12 (1): 29-34.
10.4308/hjb.29.5.681-694. DOI: 10.5530/pj.2020.12.6.
Tan J, Han Y, Han B, Qi X, Cai X, Ge S, Xue H. 2022. Extraction and Tian W, Chen G, Gui Y, Zhang G, Li Y. 2021. Rapid quantification of
purification of anthocyanins: A review. J Agric Food Res 8: 100306. total phenolics and ferulic acid in whole wheat using UV-Vis
DOI: 10.1016/j.jafr.2022.100306. spectrophotometry. Food Control 123: 107691. DOI:
Tejaputri NA, Arsianti A, Qorina F, Fithrotunnisa Q. 2019. Phytochemical 10.1016/j.foodcont.2020.107691.
analysis and antioxidant properties by DPPH radical scavenger Tofighi Z, Molazen M, Doostdar B, Taban P, Shahverdi AR, Samadi N,
activity of Ruellia brittoniana flower. Intl J Appl Pharm 11 (6): 24- Yassa N. 2015. Antimicrobial activities of three medicinal plants and
28. investigation of flavonoids of Tripleurospermum disciforme. Iran J
Pharm Res 14 (1): 225-231.

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