Bioactivity and Phytochemical Constituents of Extract Etanol from

Stem Musa paradisiaca Linn

Mayang Sari

1,3

, Tamrin

, Jamaran Kaban

and Zul Alfian

Postgraduate Chemistry Study Program, Faculty of Mathematics and Natural Sciences, Universitas Sumatera Utara,

Jl. Bioteknologi No. 1 Kampus USU, Medan, Indonesia

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Sumatera Utara,

Medan, 20155, Indonesia

Institut Kesehatan Helvetia , Jl. Kp. Sumarsono No.107, Medan-20124, Indonesia

Keywords: Phytochemical, Triterpenoid, DPPH, GC-MS.

Abstract: The search for active ingredients from plants that are secondary metabolites as a defense compound from

plants has been carried out. This study was conducted to investigate the phytochemical constituents of Musa

paradisiaca Linn’s pseudo-stem, such as alkaloids, flavonoids, steroids, terpenoids, and saponins. In this

study, we estimated the content of terpenoids and saponins and determined the activity of 1,1-diphenyl-2-

picrylhydrazyl (DPPH) scavenging. Ethanol extract of Musa paradisiaca Linn’s pseudo-stem, active as an

antioxidant (IC 50 = 494.2) with a comparison of Ascorbic acid. Chemical constituents of ethanol extract of

Musa paradisiaca Linn’s pseudo-stem are characterized by GC-MS, which shows that they contain

triterpenoid organic compounds, such as: Corticosterone, Stigmasterol, Obtusifoliol, Lupeol, and 9-

Cyclolanost-24-en-3-ol

1 INTRODUCTION

Indonesia's geographical location has a tropical

climate with high average rainfall throughout the

year so that Indonesia has very famous natural

resources. Various types of plants that can thrive

throughout the archipelago do not know the season.

The use of these plants as well as food ingredients is

also used as traditional medicine. Research on the

chemistry of natural materials is increasingly being

exploited today as a medicinal ingredient and for the

benefit of other fields. The chemical structure

diversity produced by these plants also reduces

abandoned and easily available side effects.

Banana plants, plants that are easy to breed in

tropical climates. One of the varieties known is

kepok banana plant (Musa paradisiaca Linn). Some

parts of this plant have benefits, one of which is as

an antioxidant.

The use of diphenylpicrylhydrazyl (DPPH) as a

stable free radical can estimate antioxidant activity

with IC50 parameters. As a good recommendation for

testing and evaluating data (Molyneux, 2003).

Dopamine and L-dopa compounds contained in

banana peels are significantly active as antioxidants.

The banana peel extract from the varieties (Cavendish

and Dream) had been analyzed by DPPH inhibitory

activity 26.55% to 52.66% (Fatemeh et al, 2012). The

compound content of banana peel extract (Musa

Cavendish) has been identified as Gallocatechin the

most, which is a strong antioxidant (158 mg / 100 g

dry weight) (Someya et al, 2002).

Extract of Banana peel (Musa acuminata Colla

AAA) from 4 types of banana peel has been ana-lyzed

has a high capacity to scavenge 2,2-diphenyl-1-

pikrillhidrazil (DPPH). DPPH scavenging activity of

acetone extract and methanol from banana peel

showed greater value than ethanol and water ex-tract

(Aboul-Enein, 2016). Peel extract from all nine

banana varieties showed significant antioxidant and

phytochemical activity. Antioxidant activity of fresh

green and yellow banana peel from fruit (Musa, cv.

Cavendish) was treated with 70% acetone, which was

partitioned with chloroform (CHCl

) and ethyl acetate

(EtOAc), which was evaluated (Mok-bel et al., 2005).

Pseudo-stem sap Banana has several special

properties related to various phenomena such as

browning of fruit after harvest, permanent coloring of

fabrics and fibers, antioxidant, antimicrobial and

antihemorrhagic properties. All aqueous pseudo-stem

Sari, M., Tamrin, ., Kaban, J. and Alﬁan, Z.

Bioactivity and Phytochemical Constituents of Extract Etanol from Musa paradisiaca Linn.

DOI: 10.5220/0008855100890095

In Proceedings of the 1st International Conference on Chemical Science and Technology Innovation (ICOCSTI 2019), pages 89-95

ISBN: 978-989-758-415-2

extracts, methanol and ethanol have been found to

contain good amounts of antioxidants along with

different phytochemical compounds such as

carbohydrates, proteins and phenolic compounds

(Kumar et al., 2014).

This research has been carried out phytochemical

screening test and determined the compounds

contained in the ethanol extract of kepok banana

stem (Musa paradisiaca Linn) as well as knowing

the antioxidant activity of the crude extract.

2 MATERIALS AND METHODS

2.1 Collection and Processing of Kepok

Banana Pseudo-stem (Musa

Paradisiaca Linn)

Kepok Banana pseudo-stems were collected from

the Kotamadya Medan which has a stem diameter of

about 5-10 cm collected in February 2019. Sample

was washed with tap water and dried in drying

cabinet at 500 C for 3 days, crushed with a blender

into powder. And preparations were immediately

made for crude extract ethanol.

2.2 Extraction Procedures

Kepok banana stem powder (250 gr) was extracted

with ethanol 96% immersion for 72 hours and

occasionally stirring. Filtration was carried out, the

filtrate was collected and the precipitate was soaked

with ethanol 96% for 48 hours and filtered again.

The first and second filtrates were combined and

then concentrated at 70

C using a rotary flash

evaporator. The crude extract obtained is stored in

the dark at 4ºC for further testing.

2.3 Phytochemical Tests

Introduction Phytochemical analysis is carried out to

determine the presence of various phytochemicals.

2.3.1 Phenolic Compounds

The extract (500 mg) was dissolved in 5 ml of dis-

tilled water. For this, a few drops of neutral 5%

ferric chloride solution is added. Dark green

indicates the presence of phenolic compounds

(Ingonga et al., 2015).

2.3.2 Terpenoids and Steroids

Steroids (Liebermann-Burchard reaction). The 200

mg extract material was added in 10 mL of chloro-

form. Acetic anhydride is added in a 1: 1 ratio which

results in a blue-green ring formation pointing to-

wards the presence of steroids.

Terpenoid (Salkowski test). For 200 mg of ex-

tract material, 2 mL of chloroform (CHCl

) and 3

mL of concentrated sulfuric acid (H

) were

added carefully. Reddish brown marks the presence

of terpenoids (Ingonga et al., 2015).

2.3.3 Phytochemical Tests

200 mg of extract is diluted to 10 mL with

Methanol, boiled and filtered. For 5 mL of filtrate, 2

mL of dilute ammonia is added. 5 mL Chloroform is

add-ed and gently shaken the alkaloid base extract.

The chloroform layer was extracted with 1 mL of

acetic acid. This is divided into two parts. Mayer

reagent was added to one part and Draggendorff

reagent to the other. The formation of cream (with

Mayer reagent) or reddish-brown precipitate (with

Draggendorff reagent) is considered positive for the

presence of alkaloids (Abdallah, 2016).

Mayer reagent & Wagner reagent confirmed the

presence of alkaloids in the extract. Plant extracts

are heated with 2% H

for two minutes. It is

filtered and a few drops of reagent are added

separately. With a few drops of Reagent Mayer

creamy white precipitation appears a positive result.

Indi-cates the presence of alkaloid compounds.

Wagner's reagent, the precipitate of reddish brown

appeared which also confirmed the presence of

alkaloids in the extract (Rdhia et al, 2018).

2.3.4 Saponins

Crude extract (2 g) boiled in 20 mL of distilled

water in a water bath and filtered. The filtrate was

shaken violently for stable froth which was

considered positive for the presence of saponins

(Moubayed et al., 2017).

2.3.4 Flavonoids

In the aqueous filtrate, 5 mL of dilute ammonia

solution is added, followed by concentrated H

yellow staining indicates the presence of flavonoids

(Ingonga et al., 2015).

ICOCSTI 2019 - International Conference on Chemical Science and Technology Innovation

2.4 Gas Chromatography and Mass

The analysis was carried out using Shimadzu

GCMS-QP2010S with Detector: 0.85 kV + 0.00 kV.

Electron Energy: 10 to 200 eV with helium at 1.51

ml for 1 minute as a carrier gas. The mass spec-

trometer is operated in electron (El) impact mode at

70 eV in the scanning range 50-500 m / z. Column

Flow: 1.03 mL / min Separation ratio is adjusted to

1:10. The injector temperature is 200◦C, and the

oven temperature is maintained at 70◦C for 3

minutes, rising to 200◦C. Identification of peak

extracts of raw banana plant extracts was carried out

by comparison with standard retention times, and

mass spectra obtained compared to those available in

the NIST library (NIST 14 - MassSpectral Library,

2014 version).

2.5 Activities for DPPH Radical

Scavengers

Scavenging 1,1-diphenyl-2-pikrillhidrazil (DPPH)

Radicals by the sample were monitored according to

the modified Yen and Chen (1995) method. Briefly,

2 mL aliquots of the test sample were added to 1 mL

of DPPH 0.4 mM methanol solution. Mix the vortex

for 1 minute and then leave the room temperature for

30 minutes in dark conditions, and the absorbance is

read at 517 nm (Moubayed et al., 2017). Synthetic

antioxidant ascorbic acid is used as a positive

control.

The ability of test samples to scavenge DPPH

radicals is calculated using the following equation

(Wu el al., 2009):

Inhibition percent = [(AB - AA) / AB] x 100 (1)

Where: AB = absorbance value of blank sample, AA

= absorbance value of test sample

3 RESULTS AND DISCUSSION

3.1 Phytochemical Screening

Important phytochemicals, such as alkaloids,

triterpenoids, steroids, phenolics, flavonoids and

saponins for their presence and are presented in

Table 1.

From the results of the phytochemical tests

carried out, it is clear that the high content of the

banana plant stems is terpenoids, steroids and

saponins. Further testing of crude extracts in GC-MS

was carried out to determine the compounds present

in the plant extract.

Table 1: Phytochemical test results of crude ethanol

extract of Kepok Banana pseudo-stem (Musa paradisiaca

Linn).

Secondary metabolite

Ethanol extract

Phenolic

Terpenoids

Steroids

Alkaloids

Saponins

Flavonoids

+ : The presence of secondary metabolite

- : The absence of secondary metabolite

3.2 GC-MS of Crude Extract

Table 2: Chemical constituents of ethanolic crude extract

from Musa paradisiaca Linn pseudo-stem.

Compound’s name

Peak

area

(%)

1,3,5-triazine-2,4,6-triamine

12.49

0.17

Trihloroacetic acid, tridecyl

ester

13.31

0.08

Phytol

19.07

0.04

Corticosterone

22.27

0.19

Heptasiloxane tetradecamethyl

28.29

54.05

Corticosterone 21-acetate

28.78

10.95

Stigmasterol

29.05

4.63

Obtusifoliol

29.33

8.47

Butyl-4-

[(trimethylsilyl)amino]benzoate

29.77

3.93

Propionic acid, 3-

(benzol[1,3])dioxol-5-yl)-3-(4-

methylbenzoylamino)

29.89

1.67

Sebacic acid, 4-bromo-2,6-

difluorobenzyl isobutyl ester

30.02

1.59

Lupeol

30.37

4.14

9,19-Cyclolanost-24-en-3-ol,

(3-beta)-

30.63

3.69

9,19-Cyclolanost-3-ol, 24-

methylene-,

31.22

5.49

Pentasiloxane,

1,1,3,3,5,5,7,7,9,9-decamethyl

31.65

0.22

Trimethylsilyl-2-(5H-

chromenol[2,3-b]pyridine

31.96

0.33

Ethanethioic acid, S-[8-

(diethylphosphono)octyl

33.69

0.34

The consequences associated with GC-MS

investigations led to the recognition of many

Bioactivity and Phytochemical Constituents of Extract Etanol from Musa paradisiaca Linn

compounds from GC from the ethanol extract of the

Musa paradisiaca Linn. This compound is

recognized through the mass spectrum assembled

with GC. The active principle with their retention

time [RT], molecular formula (MF), molecular

weight (MW) and concentration (%) can be accessed

in Table 2.

Seventeen chemical compounds identified from

ethanol extract from the stem of Musa paradisiaca

Linn by GC-MS analysis. The occurrence of various

bioactive compounds confirms the application of the

stem of Musa paradisiaca Linn to various diseases,

by traditional practitioners, a number of compounds

previously reported from a number of other plant

species.

From the data above (Table 2), there are eight of

the most chemical compounds: Heptasiloxane,

1,1,3,3,5,5,7,7,9,9,11,11,13,13-tetradecamethyl ( RT

28.29; 54.05%); Corticosterone 21-acetate (RT

28.78; 10.95%); Obtusifoliol (RT 29.33; 8.47%);

9,19-Cyclolanostan-3-ol, 24-methylene -, (RT 31.22;

5.49%); Stigmasterol (RT 29.05; 4.63%); Lupeol

(RT 30.37; 4.14%); Butyl 4 - [(trimethylsilyl)

amino] benzoate (RT 29.77; 3.93%); 9,19-

Cyclolanost-24-en-3-ol, (3.beta.) - (RT 30.63;

3.69%). And the bioactive compounds in the extract

have the following chemical structures:

(a)

(b)

(c)

(d)

(e)

(f)

Figure 1: Chemical structures of (a) Obtusifoliol (b)

Lupeol (c) Stigmasterol (d)9,19-Cyclolanostan-3-ol, 24-

methylene- (3β. (e) Corticosterone (f) Corticosterone

acetate.

The obtusifoliol content of 8.47%, the type of

steroid contained in stem ethanol extract is very

potential as a compound that can inhibit the

proliferation of MCF-7 and MDA-MB231 breast

cancer cells through the cell cycle which is stopped

ICOCSTI 2019 - International Conference on Chemical Science and Technology Innovation

the development and induction of apoptosis.

(Aghaei et al., 2016)

Lupeol obtained from GC-MS results as much as

4.14%. Lupeol is a pharmacologically active penta-

cyclic triterpenoid found in several medicinal plants

throughout the world. This compound shows a

hepatoprotective effect on Aflotoxin B1-induced

damage in mice. In addition, lupeol has a hepato-

protective effect on CCl

poisoning. The protective

effect of the Lupeol compound will improve kidney

injury associated with hypercholesterolemia, namely

the presence of cardioprotective which can be

beneficial in the condition of hypercholesterolemia

because it minimizes lipid abnormalities and ab-

normal biochemical changes caused by cholesterol

and mice fed colic acid (Mbaveng et al., 2014).

Stigmasterol in the crude extract of ethanol stem

as much as 4.63%. The presence of cholesterol-

lowering activities by Stigmasterol, other

bioactivities are ascribed to plant sterol compounds,

one of which has the potential to cause anti-

inflammatory effects. To investigate the effects of

stigmasterol, plant sterols, on inflammatory

mediators and metalloproteinases produced by

chondrocytes (Gabay et al., 2010).

9,19-Cyclolanostan-3-ol, 24-methylene- (3β.) In

this extract contained 9.08%, were triterpenes and n-

Hexadecanoic acid, have been reported to have

antimicrobial activity. It has also been reported that

plant sterols are a good therapeutic choice for the

management of hypercholesterolemia (Ameachi and

Chijioke, 2018).

Some antibacterial compounds, such as 24, 24-

dimethyl-9,19-cyclolanostan-3 b-ol, daucosterol,

allantoin, and D-mannitol have been reported in

aerial parts (Phthalides et al., 2018). 9.19-

cyclolanostan-3-ol.24-methylene-3.beta acting as an

anti-HIV compound, used to prevent the HIV virus.

(Arora and Kumar, 2017). Corticosterone is a

compound that can act as a metabolism (low to

moderate levels) and stress hormones (high levels)

and, can affect reproductive (Apfelbeck et al., 2017).

3.3 Antioxidant Test

Effect of ethanol extract of Musa parasiaca Linn

containing active compounds reacting with DPPH

free radicals will change to 1,1-diphenyl-2-

picrylhydrazine which is non-radical. Look at the

color changes that occur from DPPH which is purple

to yellow and proven by the smaller absorbance

value (Molyneux, 2003). The decrease in absorbance

along with the increase in plant ethanol extract was

added. So that we can determine% inhibition of each

concentration and we can determine the linear

regression equation in the Figure 2.

Based on Figure 2, the linear line equation is

obtained and from this equation is used to calculate

the IC50 value of the ethanol extract of the sample.

The results of calculation of IC50 values were

obtained 494.209. And from Figure 3 as a

comparison is ascorbic acid with an IC50 value of

5.492.

The ability of extracts to ward off DPPH is

thought to be the presence of Lupeol compounds.

The statement that Lupeol as a natural active

constituent is well-known for its anti-inflammatory,

antioxidant and neuroprotective activities (Kaundal,

2017).

Figure 2: Curve of % inhibition of Musa paradisiaca Linn

extract.

Figure 3: Curve of % inhibition of ascorbic acid.

Besides lupeol, there is also the presence of

Stigmasterol, also known as Stigmasterin or the

Wulzen anti-stiffness factor, a non-saturated plant

sterol found in various medicinal plants.

Stigmasterol is used in a number of chemical

processes designed to produce various synthetic and

semi-synthetic compounds for the pharmaceutical

industry. It acts as a precursor in the synthesis of

Bioactivity and Phytochemical Constituents of Extract Etanol from Musa paradisiaca Linn

progesterone and acts as an intermediary in

androgen biosynthesis, estrogen, corticoids 1 and in

the synthesis of vitamin D and Stigmasterol has also

been investigated for its pharmacological prospects

such as antiosteoarthritis, antihypercholestrolemic,

cytotoxic, antitumor, hypoglycemic, antimutagenic,

antioxidant, and anti-inflammatory (Chaudhary et

al., 2011).

4 CONCLUSIONS

Crude ethanol extract of Musa paradisiaca Linn

from 250 g of dried powder phytochemical

screening test was carried out and continued with

compound analysis by GC-MS. Some active

compounds are obtained which are thought to be

very beneficial for biological activities. The

presence of antioxidant activity extracts has been

evaluated. As far as we know, this research is the

first report on the bioactivity of plant ethanol extract

Musa Paradisiaca Linn Further phytochemical

research is needed to identify the active principle

responsible for activity antioxidant. This

investigation presents sufficient data about

phytochemical constituents in one polar solvent.

Bioactive compounds found in the stem of Musa

paradisiaca Linn plant hope to be applied as natural

antioxidants and can be extrapolated for clinical

studies.

ACKNOWLEDGEMENTS

We are grateful to Doctoral Department of Chemis-

try Universitas Sumatera Utara, and LPDP for

funding my research under the scholarship number

20161141021370.

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Bioactivity and Phytochemical Constituents of Extract Etanol from Musa paradisiaca Linn