Journal of Physics: Conference Series
PAPER • OPEN ACCESS You may also like
- In vitro cytotoxicity of Artocarpus lakoocha
Prenylated flavon and antibacterial activities of aqueous extract and oxyresveratrol in SH-
SY5Y cells
Artocarpus lanceifolius Roxb bark Hasriadi and Nanteetip Limpeanchob
- The Effectiveness of Raw and Dried
Artocarpus Heterophyllus (Jackfruit) Seed
To cite this article: Hamsidar et al 2019 J. Phys.: Conf. Ser. 1341 072014 as Natural Coagulant in Water Treatment
N. A. C Mahmood and Z. Z. M Zaki
- Classification of Artocarpus species based
on leaf recognition using multiclass
support vector machine
View the article online for updates and enhancements. S Daliman and N Abdul Ghapar
This content was downloaded from IP address 167.205.23.115 on 29/11/2022 at 03:21
The 3rd International Conference On Science IOP Publishing
Journal of Physics: Conference Series 1341 (2019) 072014 doi:10.1088/1742-6596/1341/7/072014
Prenylated flavon and antibacterial activities of Artocarpus lanceifolius
Roxb bark
Hamsidar1*, N H Soekamto2*, Y M Syah3, Firdaus2 and Elvira3
1Department of Pharmacy, Faculty of Sports and Health, Gorontalo State
University, Indonesia
2Department of Chemistry, Faculty of Mathematics and Natural Science,
Hasanuddin University Makassar, Indonesia
3Division of Organic Chemistry, Faculty of Mathematics and Natural Science,
Institute Technology Bandung, Indonesia
1*
[email protected], 2*
[email protected] Abstract. Prenylated flavone compounds, 14-hydroxyartonin E have been
isolated from CHCl3 extract of Artocarpus lanceifolius Roxb bark. The
molecular structure compound was determined based on the UV-Vis, IR, 1H-
NMR and 13C-NMR HSQC, HMBC spectra and compared to the previous data
reported.14-hydroxyartonin E compound provides antibacterial activity with a
moderate category against Streptococcus pneumonia and Staphylococcus
aureus but the category is weak against Escherichiacoli and Salmonella
thyposa
1.Introduction
Infectious diseases caused by bacteria, fungi, viruses, and parasites are a major threat to
public health. Although remarkable progress has occurred in the human medical world, the
impact is huge, especially in developing countries due to lack of sufficient drugs and the
emergence of widespread drug resistance [1].To date, the search effort of new antimicrobial
compounds is an important research activity. Various approaches used in finding sources of
new compounds including compounds from natural ingredients. This approach will be
produced antimicrobial compounds targeting the bacterial metabolic system, thereby it will
inhibit bacterial growth or even causing the death of the bacteria itself.
One of the plants able to grow in tropical and sub-tropical regions including in
Indonesia with the potential as a source of bioactive chemicals in the family of Moraceae.
Moraceae consists of 60 genera and 1400 species. The three main genera are Artocarpus,
Ficus, and Morus. Artocarpus consists of 50 species and spread from South Asia, Southeast
Asia to the Solomon Islands, Pacific Islands, North Australia, and Central America [2].
Ethnobotany, some parts of the Artocarpus plant by the community have long been
used as traditional medicine. The extract of stem bark A. elasticus is used as a preventive
agent, the gum used as dysentery and fever relief medicine [3]. The roots of A. heterophyllus
are used to treat fever, dysentery, and malaria, the seeds for the treatment of diarrhea, the
leaves are a remedy for boils, fever, wounds, and skin diseases [4]. The utilization of the
Artocarpus plant as traditional medicine is related to the secondary metabolites contents.
The Artocarpus lanceifolius Roxb plant with the local name Kaledang is one of the
Moraceae families. It's has been widely used as a producer of wood for heavy construction,
Content from this work may be used under the terms of the Creative Commons Attribution 3.0 licence. Any further distribution
of this work must maintain attribution to the author(s) and the title of the work, journal citation and DOI.
Published under licence by IOP Publishing Ltd 1
The 3rd International Conference On Science IOP Publishing
Journal of Physics: Conference Series 1341 (2019) 072014 doi:10.1088/1742-6596/1341/7/072014
furniture, boat building, household utensils, as a coloring material, and the fruit can be
consumed. Empirically the leaves of A. lanceifolius are used as anti-inflammatory drugs and
steeping of the bark is believed to be a drug for diarrhea. Up to now the utilization of
traditional medicine by the people still based on experience only. There is not supported by
scientific data experimentally so that research on secondary metabolites and plant activity is
still needed.
2. Experiments
2.1 General experimental procedure
Spectroscopy UV, FTIR spectrophotometer Shimadzu Prestige-21, Agilent NMR 500 MHz
with DD2 console system that operates at 500 MHz (1H) and 125 MHz (13C) frequencies,
using residual and deuterated solvent peaks as reference standards, VLC, and radial
chromatography were carried out using Merck silica gel 60 GF254 and for TLC analysis,
precoated silica gel plates (Merck Kiesel-gel 60 GF254, 0,25 mm) were used. All solvents were
of technical grade and were distilled before use.
2.2 Plant material
The collected bark of Artocarpus lanceifolius Roxb from South Kalimantan Province on
January 2018. It was identified by staff at the Herbarium Bogorience, Bogor Botanical
Garden, Bogor Indonesia and, a voucher specimen has been deposited at the herbarium.
2.3 Extraction and isolation
The dried powdered bark of Artocarpus lanceifolius Roxb (6 Kg) was successively extracted
with n-hexane, CHCl3. EtOAc and MeOH. The liquid extract CHCl3 was evaporated with a
rotary evaporator to obtain thick chloroform extract (36.5 gr). All CHCl3 extracts were
fractionated by VLC ( Si-gel, n-hexane: EtOAc). The fractions eluted with n-hexane –EtOAc
(1:1) was subjected to radial chromatography (Si-gel, n-hexane-EtOAc, 1:1) to yield, resulting
in a compound (43.2 mg) in the form of yellow powder.
2.4 Antibacterial screening
The bacterial strains employed in screening were Staphylococcus aureus, Streptococcus
pneumonia, Escherichia coli, and Salmonella typhosa. The test method refers to reference [5].
Antibacterial activity of the compound was determinate by the disc diffusion method with
slight modification in term of sample concentration, the bacteria were cultured at 37 0C for
overnight in nutrient broth. The compound to be tested were dissolved in dimethyl sulphoxide
(DMSO) at concentration 100 ppm. For screening, 10 ȝL of each sample solution was loaded
on Whatman No.1 filter paper disk ((ࣄ 6 mm). The disc was placed on the surface of the agar
plate (Nutrient agar) previously inoculated with bacteria. The agar plate was then inverted and
incubated for 24 h and 48 h at 370C. The antibacterial activity was recorded by measuring the
zone of inhibition (in mm) around each disc. Ampicillin was used as positive control and
DMSO (Dimethylsulfoxide) as the negative control in assays.
3. Results and Discussion
3.1 Isolation
The results of prenylated flavones, 14-hydroxyartonin E isolated have the color of yellow
powder, UV (MeOH) Ȝmax nm (log İ): 283 (4,23), 386 (3,38) show the structure of flavone
[6],[7] The FTIR-Ȟmax (KBR) cm -1 spectrum of Vmax 3392 cm-1 shows the presence of
2
The 3rd International Conference On Science IOP Publishing
Journal of Physics: Conference Series 1341 (2019) 072014 doi:10.1088/1742-6596/1341/7/072014
absorption bands for hydroxyl (OH) groups, a carbonyl (C=O) group conjugated at 1653 cm-1,
and a benzene ring at 1566 cm-1, 1521 cm-1, 1481 and 1431 cm-1 (Figure 1) show the structure
of flavone [7].
Figure 1. 14-hydroxyartonin E FTIR spectrum
Spectrum data are 1H-NMR (d6-acetone, 500 MHz) and 13C-NMR (d6-acetone, 125 MHz)
(Table 1). In the 1H-NMR spectrum, į 13.08 ppm (OH, s) shows chelate OH at C-5 [8] a
characteristic of flavonoid. In the 13C-NMR spectrum, a quaternary carbon (įC= 183 ppm)
shows a carbonyl group (C = O) conjugated to C-4 is a characteristic of a flavone [9]. These
H and C signals can be explained in detail with the help of a two-dimensional NMR spectrum
such as Heteronuclear Single Quantum Correlation (HSQC) and Heteronuclear Multiple Bond
Correlation (HMBC). In the 1H-NMR(d6-acetone, 500 MHz) spectrum shows the presence of
signals for 2 methyl protons at į 1.4 (6H, s), 1 methyl proton at į 1.7 (3H, s) and įH 4.03
associated with 2 proton oxymethylene at C- 14 [10]. This shows the presence of an isoprene
group on the C-3 skeleton of flavones. It also supported by the presence of signals for 3
methyl groups (į 28.3) with two methyl groups, į 21.7 1 methyl, other signals on the H-
NMR spectrum show the presence of 2 aromatic protons atį 6.15 (IH, s, H-6) and į 6.59 (1H,
s, H-3’). The other methyl position is replaced by the presence of an oximetry group at į 61.2
ppm. The two vinyl protons at į 6.62 (1H, d, J = 10 Hz) and į 5.67 (1H, d, J = 10) suggest the
presence of a dimethylallyl group and this indicates a large coupling that matches the cis
coupling so that the group might the side containing the signal in the form of isoprene which
undergoes cyclization forms a Piran ring.13C NMR spectrum of the compound showed
resonance to 25 carbon atoms. including three methyl groups, 1 oxymethylene group, 6
oxyaryl carbons, five carbon metines, 1 carbonyl group corresponding to 14-hydroxyartonin E
( Figure 2). The above data suggests that the isolated compounds are 14 hydroxyartonin E. It
is appropriate previous study [10] in Table 1.
3
The 3rd International Conference On Science IOP Publishing
Journal of Physics: Conference Series 1341 (2019) 072014 doi:10.1088/1742-6596/1341/7/072014
Table 1. Data spectrum 1H-NMR and 13C-NMR, HMBC 14-hydroxyartonin E
C atom 1
H NMR, į ppm (multiplicities, J in Hz 13
C NMR į
HMBC
number unit) ppm
1 1’ 1 1’
2 - 162,5 161,7
3 - 120,7 119,5
4 - 183 181
5 - 160 160,8
6 6.15 (1H.s) 6.28 (1H.s) 99,8 98,7 C-5, C-7,C-8,C-9
7 - 162,6 158,4
8 - 101,7 100,4
9 - 104,9 104,2
10 - 153,2 151,7
1’ - 111,1 109,1
2’ - 150,0 148,8
3’ 6.59 (1H.s) 6.62(1H,s) 104,9 103,9 C-1’, C-5’, C-4’,C-2
4’ - 149 148,4
5’ - 139 138,0
6’ 6.94(1H.s) 7.04(1H,s) 117 116,1 C-2’, C-5’, C-2
11 3.2(2H, d,J =6,05) 3,27(2H, d, 7,7) 24,7 23,1 C-3, C-12, C-13,
C2,C4
12 5,28(1H, t,9,7) 5,62(1H, t,7,7) 124,6 127,5 C-15, C-11
13 - 136,6 135,9
14 4,03 (2H, s) 4,30 (2H, s) 61,2 59,2
15 1,7 (3H, s) 1,89 (3H, s) 21,7 21,1 C-3, C-12,C-13
16 6,62 (1H, d,10) 6,62 (1H, d,10) 115,4 114,1 C-10, C-8, C-18, C-5’
17 5,67 (1H, d,10) 5,56 (1H, d,10) 128 127,6 C-18, C-8
18 - - 78,8 78,0
19 1,4 (3H, s) 1,47(3H, s) 28,3 27,6 C-17
20 1,4 (3H,s) 1,24(3H, s) 28,3 27,6 C-17
21 13,08 (OH, s) C-5, C-7, C-9,C-8
1
Isolated compounds (1H NMR, 500 MHz, acetone-d6, 13C NMR, 125 MHz, acetone-d6
1'
Shugeng CaO et al 2014 ((1H NMR, 500 MHz, CDCl3, 13C NMR, 125 MHz, DMSO)
The HMBC spectrum (Figure 2) shows a long-distance correlation between singlet protons
(1H, 6) and four quaternary carbons at į 160 (C-5), į 162.6 (C-7), į107.1 (C-8) and į 104,9
(C-9). This shows the existence of a substituted isoprene group at C-8 which undergoes
cyclization form a Piran ring. The singlet proton at į 13.08 also shows the same long-
distance correlation with the singlet proton (1H, 6).the doublet proton at į 24.7 (2H, 11)
shows a long-distance correlation and four quaternary carbon į 120.7 (C-3), į 183 (C-4), į
162.5 (C-2), į 136.6 (C -13). This shows the presence of an isoprene group on C-3.
4
The 3rd International Conference On Science IOP Publishing
Journal of Physics: Conference Series 1341 (2019) 072014 doi:10.1088/1742-6596/1341/7/072014
Figure 2. Structure and correlation of HMBC 14-hydroxyartonin E
3.2. Antimicrobial screening
Antibacterial activity tests of these compounds using sterile paper disc diffusion methods,
agar nutrient media, using gram-positive bacteria (Staphylococcus aureus and Streptococcus
pneumonia) and gram-negative bacteria (Escherichia coli and Salmonella typosa) with
inhibitory zones are shown in Table 2.
Table 2. Results of antibacterial screening of 14-hydroxyartonin E compounds
Compounds The Diameter of the inhibition zone (mm)
Gram-positive Gram-negative
S. aureus S. E. coli S. typhosa
pneumonia
24 48 24 48 24 48 24 48
hour hour hour hour hour hour hour hour
14-hydroxyartonin E
10,8 14,0 10,3 10,8 9,1 10,1 9,1 9,8
Positive control
9,5 9,8 13,2 9,2 7,3 14,2 7,4 8,0
Ampicillin
Negative control
6,2 6,4 6,7 6,5 6,3 6,3 6,5 6,5
DMSO
Table 2 shows that the 14-hydroxyartonin E compound provides antibacterial activity with a
moderate category against S. aureus and S. pneumonia with inhibition zones of 14 mm and
10.8 mm [11], but the category is weak against E. coli bacteria and S.thyposa with a barrier
zone of 10.1 mm and 9.8 mm respectively. However, the antibacterial activity of the
compound was stronger than that of positive ampicillin control. The results of previous
studies revealed that the antibacterial activity in these compounds is related to the presence of
polyhydroxy groups in rings A and B, as well as the presence of aliphatic substitutions on ring
A [11].
5
The 3rd International Conference On Science IOP Publishing
Journal of Physics: Conference Series 1341 (2019) 072014 doi:10.1088/1742-6596/1341/7/072014
4. Conclusion
This research has isolated a prenylated flavone compound, 14-hydroxyartonin E from the bark
of Artocarpus lanceifolius Roxb. 14-hydroxyartonin E compound provides antibacterial
activity with a moderate category against Streptococcus pneumonia and Staphylococcus
aureus but the category is weak against Escherichiacoli and Salmonella thyposa
Acknowledgment
We thank the Herbarium Bogorience, Bogor-Indonesia for identification of the plant species
and Ministry of Research, Technology and Higher Education, Republic of Indonesia (Doktor
Dissertation Grand, 2018) for financial support.
References
[1] Okeke IN, Laxminarayan R, Bhutta ZA, Duse AG, Jenkins P, O Brien TF, Pablos
Mondez A, Klugman KR, 2005, Antimikroba resistance in developing countries. Part I.
Lancet infect disk Vol 5:481-93 (http://infection the lancet.com) Accessed 14 July 2019.
[2] Hakim 2011, Diversity of Secondary Metabolites from Genus Artocarpus (Moraceae),
Bioscience vol 2, no 3, Pp. 146-156
[3] Musthapa I, Juliawaty LD, Syah MY, Hakim EH, LatipJ, GhisalbertiE, 2009. An
Oxepinoflavon from Artocarpus elasticus with Cytotoxic Activity Againts P-388 cell.
Arch Pharm Res vol 32, No 2, 191-194.
[4] Heyne K. 1987. Indonesian Useful Plants, Research and Development Agency, Ministry
of Forestry, Jakarta
[5] Septama A, and Panichayupakaranant P, 2015. Antibacterial, Assay-Guided Isolation of
Active Compounds from Artocarpus Heterophyllous heartwoods. Pharm Biol, 2015; 53
(11): 1608-1613
[6] Markham KR. 1988. How to Identify Flavonoids. Chemical Division Department of
Science and Industry Research, Petone New Zealand. ITB Bandung Publisher
[7] Hakim et al, 1999. Pyranoflavone and furanodihidrobenzosanton derivatives from
Artocarpus lanceifolius, Proc ITB, Vol 31, no. 2
[8] Eliza, Syah YM, Lia DJ, Sjamsul AA, Lukman Makmur, Euis H. Hakim. 2008. Three
flavonoid derivates from leaves of Artocarpus Lanceifolius Proceeding of The
International Seminar on Chemistry (pp. 265-268) Jatinangor, 30-31 October 2008
[9] Syah, YM, 2018. The Basis of determining the structure of Natural compounds aromatic
compounds, Spectroscopic Laboratory Faculty of Mathematics and Natural Science,
Institute Technology Bandung, Indonesia.
[10] Cao S, Butler MS, and Buss Antony D, 2002. Flavonoids from Artocarpus lanceifolius,
Natural product Research, vol 17, no 2, pp 79-81
[11] Hashim, NM, Rahmani M, Ee GCL, Sukari MA, YahayuM, AminMA, AliAM, Go R.
2012. Antioxidant, Antimicrobial, and Tyrosinase Inhibitory Activities of Xanthones
Isolated from Artocarpus obtusus F.M.Jarret, Molecules. 17, 6071-6082
