MELALEUCA ERICIFOLIA SM.

www.wjpr.net Vol 8, Issue 9, 2019.

Fatma. World Journal of Pharmaceutical Research

110

RADICAL SCAVENGING POTENTIAL OF COMPOUNDS FROM

MELALEUCA ERICIFOLIA SM.

Fatma M. Abdel Bar1*

,2

1Department of Pharmacognosy, Faculty of Pharmacy, Prince Sattam Bin Abdulaziz

University, Al-Kharj 11942, Saudi Arabia.

2Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura

35516, Egypt.

ABSTRACT

Plants belonging to genus Melaleuca are economically important

plants as the leaves of most species contain volatile oils. In this study,

the non-volatile constituent of the leaf and bark of Melaleuca ericifolia

Sm. grown in Egypt was investigated. The leaf extract afforded (E)-

3`,4`-dimethoxy cinnamaldehyde 1, methyl tri-O-methyl gallate 2,

kaempferol 3, 3,3`,4`-trimethoxy ellagic acid-4-O--glucoside 4 and 3-

methoxyellagic acid 4-O--rhamnopyranoside 5. While the bark

extract afforded melaleucic acid 6 and gallic acid 7. The structures of

the isolated compounds were identified using 1D and 2D NMR

spectroscopy. The antioxidant activities represented by %inhibition

and free radical scavenging profile of ABTS+ radical was evaluated at

25, 50, 100 and 200 M, for 30 min. The results showed that gallic

acid 7 (88% inhibition, at 25 M) and kaempferol 3 (85% inhibition, at 100 M)

respectively, were the most active compounds with comparable activity to ascorbic acid as a

positive control. Remarkably, the lupane-type triterpene melaleucic acid 6 showed

considerable ABTS+ radical bleaching activity (53.7 %inhibition at 200 M, after 5 min). In

conclusion, this study reported for the first time the isolation of compounds 4 and 6 from this

plant and the antioxidant activity of melaleucic acid.

KEYWORDS: Melaleuca ericifolia; melaleucic acid; 3,3,4`-trimethoxy ellagic acid-4-O-

glucoside; antioxidant activity; radical scavenging activity.

World Journal of Pharmaceutical Research SJIF Impact Factor 8.074

Volume 8, Issue 9, 110-123. Research Article ISSN 2277– 7105

Article Received on

04 June 2019,

Revised on 25 June 2019,

Accepted on 15 July 2019,

DOI: 10.20959/wjpr20199-15478

*Corresponding Author

Dr. Fatma M. Abdel Bar

Department of

Pharmacognosy, Faculty of

Pharmacy, Prince Sattam

Bin Abdulaziz University,

Al-Kharj 11942, Saudi

Arabia.



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INTRODUCTION

Melaleucas are commonly known "paper-bark trees". The essential oil of Melaleuca

alternifolia, ―tea tree oil‖ is the most common one. Melaleuca ericifolia Sm. is an evergreen

bushy shrub to small tree, with grayish papery bark, needle-like leaves and white to cream

scented bottlebrush-like flowers, known as the Swamp Paperbark tree.[1]

Phytochemical

studies on M. ericifolia Sm. is mainly concerned with the volatile oil of this plant. Great

variation in the chemical composition of the volatile oil has been observed based on its

geographical source. The chemical composition of essential oil of M. ericifolia Sm. growing

in southeastern Australia was composed mainly from the terpenoids, linalool 60% v/v and

1,8-cineole 16%v/v.[2]

However, the essential oil of M. ericifolia Sm. grown in Egypt was

shown to contain the phenylpropanoid, methyleugenol 96.84% v/v.[3,4]

The essential oil of M.

ericifolia Sm. showed antibacterial, antifungal, antiviral activities (Farag et al. 2004, Farag

1998). Additionally, the antioxidant activity of the essential oil of M. ericifolia Sm. has been

investigated by the same work group.[4]

The presence of pentacyclic triterpenes including 28-norlupane derivatives, betulinic acid,

betulinaldehyde, betulin, platanic acid, ursolaldehyde, ursolic acid, and asiatic acid has been

previously reported.[5]

The antiprolifrative activity of these pentacyclic triterpenes have been

also described.[5]

Regarding the phenolic contents of this plant, several phenolics have been

identified including ericifolin, gallic and ellagic acid derivatives, in addition to flavonoids

such as kaempferol, quercetin, myricetin and their glycosides.[6]

The hepatoprotective effect

of praecoxin A, a polyphenolic from M. ericifolia Sm., has been also investigated against

CCl4‐induced toxicity in mice.[7]

Nevertheless, no studies addressed the antioxidant activity of the non-volatile compounds

isolated from this plant. Therefore, this work aimed at isolation and characterization of the

non-volatile constituents of the leaf and bark extracts of M. ericifolia Sm. and investigation of

their antioxidant activity using ABTS+ radical bleaching assay.

MATERIALS AND METHODS

Plant Materials

Branches of M. ericifolia Sm. growing in Mansoura University, Egypt, were collected in

January 2004, leaves and barks were separated, dried and powdered. The authentication of

the plant was kindly implemented by Prof. Dr. Sayed F. Khalifa, Faculty of Sciences, Ain



112

Shams University, Cairo, Egypt. A voucher specimen was deposited at the Pharmacognosy

Dept., Mansoura University, Egypt (06-Mansoura-1).

General experimental

The 1H and

13C NMR spectra were recorded in CDCl3, CD3OD, pyridine-d6 and DMSO-d6

(dimethyl sulfoxide) using TMS as an internal standard, on a JEOL Eclipse NMR

spectrometer operating at 400 MHz for 1H and 100 MHz for

13C. The solvents used for

extraction and chromatographic separations were of reagent grade. TLC analysis was carried

out on precoated silica gel 60 F254 500 µm TLC plates, using the developing systems

chloroform-methanol (9:1). For TLC, silica gel 60 F254 plates (EMD Chemicals Inc.) were

used. For CC., silica gel 60 (EMD Chemicals Inc.), 70-230 mesh, or Silica gel (Natland

International Corporation), 230-400 mesh, were used. For gel permeation CC. Sephadex LH20

(SIGMA-ALDRICH) was used. For ABTS+

radical assay, Azino-bis-(3-ethylbenzthiazoline-

6-sulfonic acid) was purchased from Fluka (Buchs, Switzerland); MnO2 was purchased from

Sigma–Aldrich (Steinheim, Germany), Ascorbic acid (Memphis Pharmaceutical Co., Cairo,

Egypt), Phosphate buffer from BDH Chemicals (London, UK) and absorbance was obtained

using a Bio-Tek Elisa microplate reader (Winooski, VT, USA).

I- Phytochemical investigation of leaves of M. ericifolia Sm.

Extraction

The powdered leaves of Melaleuca ericifolia Sm. (2.5 kg) were extracted with methanol (7 x

2 L) and methanol-water (7.5:2.5, 2 x 2 L). The combined methanol extract was then

concentrated under vacuum at 45 C°. The dry methanol extract (915 g) was dissolved in

methanol-water (1.5: 0.5 L). The hydro-alcoholic solution was partitioned successively using

n-hexane, chloroform and EtOAc. The obtained extracts were evaporated under vacuum at

45°C and kept for phytochemical investigation.

Column chromatographic investigation of n-hexane extract of M. ericifolia Sm. leaves

The n-hexane extract (135 g) was chromatographed over silica gel CC. and eluted with n-

hexane-EtOAc mixtures of increasing polarity starting with n-hexane 100%. Fractions of 200

mL were collected to give 50 fractions. Similar fractions were then grouped and purified as

follows.

Fraction (12-16), 15.6 g, eluted with n-hexane-EtOAc (9.5: 0.5), revealed the presence of

one major spot [Rf 0.21, n-hexane-EtOAc (8:2)]. Purification using silica gel CC. and n-



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hexane-EtOAc (gradient) give 91 sub-fractions. Sub-fraction (77-88), 70 mg, was further

purified using medium-pressure liquid chromatography (MPLC), C18 silica gel and water-

methanol (50:50) to afford compound 1, 12 mg.

Fraction 5 (17-28), 5 g, eluted with n-hexane-EtOAc (9.5:0.5), revealed the presence of

presence of seven major spots [n-hexane-EtOAc (8:2)]. This fraction was purified by

repeated column chromatography using silica gel and n-hexane-EtOAc (9.5:0.5), 50 mL

fractions were collected to give 37 sub-fractions. Sub-fraction (22-30), 2.5 g, was further

fractionated using silica gel CC., n-hexane-EtOAc (gradient elution) and fractions of 50 mL

were collected to give 59 sub-fractions. Sub-fraction (34-41), 1.3 g, was further purified

using MPLC, C18 silica gel and water-methanol, gradient elution. Fractions of 5 mL were

collected to obtain sub-fraction (21-26), eluted with water-methanol (3:7), which afforded

compound 2 [Rf 0.37, n-hexane-EtOAc (8:2)], 200 mg.

Investigation of the chloroform extract of M. ericifolia Sm. leaves

The chloroform extract was divided based on its components into two parts (A and B).

Chloroform-A extract was obtained as the first crop and contained a large amount of gel

precipitate that was evaporated into a yellowish solid (142.0 g, 5.6 %w/w). Unlike the

chloroform-B which was obtained as a brown viscous liquid (14.0 g, 0.6 %w/w).

The chloroform-B extract, 14 g, was fractionated using silica gel and chloroform-methanol,

gradient elution and fractions of 50 mL were collected to give 48 fractions purified as

follows.

Fraction (21-23), 300 mg, eluted with chloroform-methanol (9.5: 0.5), revealed the presence

of two major spots. The fraction was further purified by gel permeation on Sephadex LH20

column and chloroform-methanol, gradient elution and fractions of 5 mL were collected to

obtain 420 sub-fractions. Sub-fractions (370-400), eluted with chloroform-methanol (8:2)

afforded compound 3 [Rf 0.77, chloroform-methanol (8:2)], 15 mg.

Fraction (31-33), eluted with eluted with chloroform-methanol (9:1), afforded compound 4

[Rf 0.23, chloroform-methanol (9:1)], 100 mg.

Fraction (39-41), eluted with chloroform-methanol (8:2), afforded compound 5 [Rf 0.13,

chloroform-methanol (9:1)], 35 mg.



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II- Phytochemical investigation of the bark of M. ericifolia Sm.

Extraction

The powdered bark of Melaleuca ericifolia (900 g) was extracted with methanol (5 x 1 L) and

methanol-water (7.5:2.5, 2 x 1 L). The combined methanol extract was concentrated under

vacuum at 45 °C. The dry methanol extract (90 g), was partitioned using n-hexane and

EtOAc, respectively.

Column chromatographic investigation of the EtOAc extract of the bark

The EtOAc extract (12 g) was purified using gel permeation on Sephadex LH20 column,

chloroform-methanol (gradient elution) and sub-fractions of 50 mL were collected to give 82

fractions. Similar fractions were then grouped and purified as follows:

Fraction (38-39), 1 g, eluted with chloroform-methanol (9:1), revealed the presence of one

major spot [Rf 0.51, chloroform-methanol (9.5:0.5)]. The fraction was further purified using

silica gel and gradient elution with chloroform-methanol. Fractions of 25 mL were collected.

Sub-fraction (8-12), eluted with chloroform-methanol (9.8:0.2) afforded compound 6, 10 mg.

Fraction (75-82), 200 mg, eluted with chloroform-methanol (8:2), revealed the presence of

one major spot [Rf 0.76, EtOAc-methanol (8:2)]. The fraction was further purified using

MPLC, C18 silica gel and water-methanol (gradient elution). Fractions of 5 mL were

collected. Sub-fractions (14-30) eluted with water-methanol (9:1) afforded compound 7, 25

mg.

Antioxidant ABTS+ radical bleaching assay

The procedure was according to the published methods with some modification.[8-11]

Thoroughly, for preparation of the derived ABTS+ radical, 2 mL of ABTS solution (60 mM)

was added to 3 mL of MnO2 solution (25 mg/mL), all prepared in aqueous phosphate buffer

solution (pH 7, 0.1 M). The mixture was shaken, centrifuged and decanted. The formed

radical cations are almost prompt and stable for several hours. Duplicates were prepared for

each sample in a 96-well microplate. The absorbance (A) of the preformed ABTS+

radical

blue-green solution at 734 nm was adjusted to approximately 0.5 (Acontrol). The absorbance

(Atest) was measured upon the addition of aliquots of 20 L of the test sample (200, 100, 50,

25 M) in spectroscopic grade MeOH–buffer (1:1 v/v) to 180 L the ABTS•+

solution.

Duplicate of each sample was used in this assay. Ascorbic acid was used as a positive control.

Blank sample was run without ABTS+ radical solution and using MeOH–phosphate buffer



115

(1:1) instead samples. Negative control was run with ABTS•+

and MeOH–phosphate buffer

(1:1) only.

The %inhibition was calculated from the equation:

%Inhibition = Acontrol – Atest/ Acontrol x 100

RESULTS AND DISCUSSION

Identification of the isolated compounds

The structures of the isolated compounds (1-7), Figure 1, were identified using 1D and 2D

NMR spectroscopy. Based on 1H and

13C NMR data of compound 1 was identified as the

known compound (E)-3`,4`-dimethoxy cinnamaldehyde. Compound 1 has not been isolated

before from genus Melaleuca.

Compound 2 showed a good example of symmetry in 1H and

13C NMR data. Compound 2

was assigned based on its NMR spectra and comparison with published data[12]

to be methyl

tri-O-methyl gallate, which has not been isolated before from genus Melaleuca.

The structure of 3 was determined based on 1H and

13C NMR to be the flavonol aglycone,

kaempferol which has been isolated before from M. ericifolia Sm.[6]

Assignment of 1H and

13C NMR data of 4, HETCOR and HMBC determined its structure to

be the known compound, 3,3`,4`-trimethoxy ellagic acid-4-O- -glucoside.[13]

It is worth to

note that this is the first report of this compound in genus Melaleuca.



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Figure 1: Structures of the isolated compounds from Melaleuca ericifolia.

Compound 5 was determined based on 1H and

13C NMR data (Table 1) to be 3-

methoxyellagic acid 4-O--rhamnopyranoside which has been isolated before from M.

ericifolia Sm. (Hussein et al., 2007). However, the underlined 13

C NMR C values (Table 1)

are miss-assigned as C-3 replaced C-4 and C-6 replaced C-6`. The true values are corrected

based on HMBC correlations (Figure 2a) that showed clearly 3J-HMBC correlation of the

methoxyl group (C-8) with a quaternary signal at 142.2 (C-3) and 3J-HMBC correlation of

the anomeric proton H-1`` with a quaternary carbon signal at 146.9 (C-4). Similarly, the C

values for C-6 and C-6` are corrected based on 2J-HMBC correlation of the proton singlet at

7.69 (H-5) with a quaternary carbon at 107.4 (C-6) and the proton singlet at 7.48 (H-5`)

with the carbon signal at 111.7 (C-6`), Figure 2b.



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(a)

(b)

Figure 2a,b. Expanded HMBC correlations of compound 5.

Table 1: 1

H and 13

C NMR Data of Compound 5 (DMSO-d6, at 400 MHz for 1H

and 100

MHz for 13

C, Coupling constants (J) are in Hz).

Position H (J=Hz) C (ppm) HMBC

1 --- 114.7, qC

2 --- 140.6, qC

3 --- 142.2, qC

4 --- 146.9, qC

5 7.69, s 112.0, CH 1, 3, 4, 6, 7

6 --- 107.4, qC

7 --- 159.2, qC

8-OCH3 4.03, s 61.3, CH3 3

1` --- 113.5, qC

2` --- 136.5, qC

3` --- 140.6, qC

4` --- 153.1, qC

5` 7.48, 5 111.9, CH 1`, 3`, 4`, 6`, 7`

6` --- 111.7, qC

7` --- 159.2, qC

1`` 5.47, s 100.6, CH 4, 2``, 3``, 5``

2`` 4.01, m 70.5, CH 4``

3`` 3.86, m 70.6, CH 5``, 4``

4`` 3.33, m 72.3, CH

5`` 3.52, m 70.4, CH

6``(Me) 1.13, d (6.2) 18.4, CH3

1H NMR of compound 6 (Table 2) showed only 5 methyl signals and two exomethylene

protons at 4.82 (Ha -29) and 5.06 (Hb -29) suggesting a lup-20-ene nucleus with the

oxidation of two methyl into either CHO and/or COOH. 13

C NMR data showed two

quaternary carbon signals at 178.4 and 179.2 assigned to the two carboxylic groups at C-



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27 and C-28, respectively. Different protons were assigned using HETCOR and COSY

correlations.

Table 2: 1H and

13C NMR data of compounds 6 (In pyridine-d6 at 400 MHz for

1H and

100 MHz for 13

C, Coupling constants (J) are in Hz).

Position H (J=Hz) C (ppm)

1 1.18, m , 1.80, m 39.3, CH2

2 1.76, m, 1.95, m 28.2, CH2

3 3.20, dd (11.0, 5.1) 77.7, CH

4 --- 39.1, s

5 1.00, m 55.9, CH

6 1.62, m, 1.80, m 18.7, CH2

7 1.96, m, 2.88, m 35.4, CH2

8 --- 40.7, s

9 2.25, m 52.3, CH

10 --- 37.7, s

11 1.34, m, 1.51, m 21.1, CH2

12 2.70, m, 2.09, m 26.9, CH2

13 2.93, m 40.2, CH

14 --- 59.9, s

15 2.54, m, 1.94, m 28.6, CH2

16 1.90, m, 2.06, m 38.3, CH2

17 --- 56.4, s

18 2.14, dd (11.4, 11.4) 51.6, CH

19 3.68, ddd (10.6, 10.6, 4.0) 47.8, CH

20 --- 151.0, s

21 1.56m, 2.54m 31.0, CH2

22 1.53m, 2.27m 37.6, CH2

23 1.04, s 28.4, q

24 0.97, s 16.4, q

25 0.86, s 16.9, q

26 1.18, s 17.4, q

27 --- 178.4, s

28 --- 179.2, s

29 4.82, brs, 5.06, brs 110.2, CH2

30 1.92, s 19.1, q

The structure of 6 was confirmed based on different NMR spectral method to be the known

compound melaleucic acid which has been isolated before from the bark and heartwood of

some species from genus Melaleuca.[14-16]

However, this is the first report of this compound

in Melaleuca ericifolia.

Based on 1H and

13C NMR, compound 7 was assigned to be gallic acid which has been

isolated before from different Melaleuca species.[17-19]



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Antioxidant activity

Evaluation of the antioxidant activity of the isolated compounds (1-7) using ABTS+ radical

bleaching assay showed that kaempferol (3) and gallic acid (7) were the most active among

the tested compounds (Figure 3).

Figure 3: Antioxidant activity of the different compounds (1–7) using ABTS+ radical

scavenging assay and ascorbic acid (As.) as a positive control after 30 min, at different

concentrations (200, 100, 50, 25 M), absorbance was measured at 750 nm.

Gallic acid (7) showed potent antioxidant activity (85-88 %inhibition) comparable to the

positive control, ascorbic acid at all tested concentrations (25, 50, 100 and 200 M), Figure 3,

4a, 4d. This may be explained by the presence of three adjacent free phenolic OH groups.[20]

Likewise, kaempferol (3) showed strong antioxidant activity at 50, 100 and 200M (77-85

%inhibition), Figure 3, 4b, due to two meta phenolic OH in ring-A.[20]

Interestingly, the

lupane-type triterpene melaleucic acid (6) showed considerable ABTS+ radical bleaching

activity started after 5 min and become constant during the experiment time (53.7% inhibition

at 200 M), Figure 3, 4c. Thus, this study reported for the first time the antioxidant activity of

melaleucic acid. For the ellagic acid derivatives (4 and 5), compound (5) showed slight

antioxidant activity (5-30 %inhibition) due to the presence of only two phenolic OH groups

in the bulky structure. However, compound 4 did not show any significant ABTS+ radical

bleaching activity. This is can be explained by the lack of any free phenolic OH groups in the

structure of 4.[20]

Similarly, compounds 1 and 2 showed insignificant activity for the same

reason.



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Figure 4: Time suppression profile of free radical scavenging activity of ABTS+ radical

at different concentrations (750 nm); (a) compound 7; (b) 3; (c) 6; (d) ascorbic acid.

(E)-3`,4`-dimethoxy cinnamaldehyde 1, NMR data (In CDCl3, at 400 MHz for 1H and 100

MHz for 13

C, coupling constants (J) are in Hz, carbon multiplicities were determined by APT

experiment); H 9.65, d (8.0 Hz, H-1), 6.58, dd (15.7, 8.0 Hz, H-2), 7.40, d (15.7 Hz, H-3),

7.07, d (1.8 Hz, H-2`), 6.89, d (8.4 Hz, H-5`), 7.15, dd (8.4, 1.8 Hz, H-6`), 3.92, s (H3-7`),

3.93, s (H3-8`).13

C NMR data;C 193.8, CH (C-1), 126.8, CH (C-2), 153.0, CH (C-3), 127.1,

qC (C-1`), 109.8, CH (C-2`), 152.9, qC (C-3`), 149.7, qC (C-4`), 111.1, CH (C-5`), 123.6,

CH (C-6`), 56.1, CH3 (C-7`), 56.0, CH3 (C-8`).

Methyl tri-O-methyl gallate 2, NMR data (In CDOD3, at 400 MHz for 1H and 100 MHz for

13C, coupling constants (J) are in Hz, carbon multiplicities were determined by APT

experiment);H 7.27, s (H-3/7), 3.82, s (H3-1`/3`), 3.87, s (H3-2`), 3.80, s (H3-4`).13

C NMR

data; C 166.7, qC (C-1), 125.2, qC (C-2), 106.5, CH (C-3), 153.0, qC (C-4), 142.1, qC (C-5),

153.0, qC (C-6), 106.5, CH (C-7), 55.3, CH3 (C-1`/3`), 59.8, CH3 (C-2`), 52.4, CH3 (C-4`).



121

Kaempferol 3, NMR data (In DMSO-d6, at 400 MHz for 1H and 100 MHz for

13C, coupling

constants (J) are in Hz, carbon multiplicities were determined by APT experiment); H 6.19,

d (1.8 Hz, H-7), 6.44, d (1.8 Hz, H-9), 8.03, d (8.8 Hz, H-2`), 6.92, d (8.8 Hz, H-3`), 6.92, d

(8.8 Hz, H-5`), 8.03, d (8.8 Hz, H-6`).13

C NMR data; C 147.3, qC (C-2), 136.2, qC (C-3),

176.5, qC (C-4), 161.3, qC (C-5), 98.8, CH (C-6), 164.5, qC (C-7), 94.0, CH (C-8), 159.8, qC

(C-9), 103.6, qC (C-10), 122.2, qC (C-1`), 130.1, CH (C-2`/6`), 116.0, CH (C-3`/5`), 156.7,

qC (C-4`).

3,3`,4`-Trimethoxy ellagic acid-4-O--glucoside 4, NMR data (In DMSO-d6, at 400 MHz for

1H and 100 MHz for

13C, coupling constants (J) are in Hz, carbon multiplicities were

determined by APT experiment); H 7.58, s (H-5), 4.04, s (8-OCH3), 7.82, s (H-5`), 4.11, s

(8`-OCH3), 3.99, s (9`-OCH3), 5.16, d (7.4 Hz, H-1``), 3.34, m (H-2``), 3.37, m (H-3``), 3.21,

m (H-4``), 3.43, m (H-5``), 3.50, m (H-6``a), 3.70, m (H-6``b). 13

C NMR data; C112.8, qC

(C-1), 141.7, qC (C-2), 141.4, qC (C-3), 152.5, qC (C-4), 108.0, CH (C-5), 113.3, qC (C-6),

158.9, qC (C-7), 61.9, CH3 (8-OCH3), 113.1, qC (C-`), 141.7, qC (C-2`), 142.2, qC (C-3`),

154.8, qC (C-4`), 112.5, CH (C-5`), 114.1, qC (C-6`), 158.7, qC (C-7`), 62.2, CH3 (8`-

OCH3), 57.3, CH3 (9`-OCH3), 101.8, CH (C-1``), 73.9, CH (C-2``), 77.0, CH (C-3``), 70.0,

CH (C-4``), 77.8, CH (C-5``), 61.1, CH2 (C-6``).

CONCLUSIONS

In this research, the chemical composition of the Swamp Paperbark tree, Melaleuca ericifolia

Sm. has been investigated. The isolation and characterization of seven known compounds

were reported from the leaves and barks of this plant. Compounds 4 (3,3`,4`-trimethoxy

ellagic acid-4-O--glucoside) and compound 6 (melaleucic acid) were reported for the first

time from this plant. The results of ABTS+ radical scavenging assay showed that gallic acid 7

and kaempferol 3 were the most active compounds while, the lupane-type triterpene

melaleucic acid 6 showed moderate antioxidant activity.

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