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Abstract

Chemical investigation of the ethanol extract of the leaves of Moringa oleifera Lam. yielded lutein (1), β-carotene (2), phytyl fatty acid ester (3), polyprenol (4), chlorophyll a (5), β-sitosterol (6), triacylglycerols (7), fatty acids, fatty alcohols, and saturated hydrocarbons. Their structures were identified by comparison of their NMR data with those reported in the literature.
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Der Pharma Chemica, 2015, 7(7):395-399
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ISSN 0975-413X
CODEN (USA): PCHHAX
395
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Chemical Constituents of Moringa oleifera Lam. Leaves
Consolacion Y Ragasa
1,2*
, Melanie P. Medecilo
3
, and Chien-Chang Shen
4
1
Chemistry Department, De La Salle University Science & Technology Complex Leandro V. Locsin
Campus, Biñan City,Laguna, Philippines.
2
Chemistry Department, De La Salle University, 2401 Taft Avenue, Manila, 1004, Philippines.
3
Biological Sciences Department, De La Salle University-Dasmariñas, Cavite, Philippines.
4
National Research Institute of Chinese Medicine, Ministry of Health and Welfare, 155-1, Li-Nong St.,
Sec. 2, Taipei 112, Taiwan.
_____________________________________________________________________________________________
ABSTRACT
Chemical investigation of the ethanol extract of the leaves of Moringa oleifera Lam. yielded lutein (1), β-carotene
(2), phytyl fatty acid ester (3), polyprenol (4), chlorophyll a (5), β-sitosterol (6),triacylglycerols (7), fatty acids, fatty
alcohols, and saturated hydrocarbons. Their structures were identified by comparison of their NMR data with those
reported in the literature.
Keywords: Moringa oleifera Lam, Moraceae, lutein, β-carotene, phytyl fatty acid esters, polyprenol, chlorophyll a,
β-sitosterol, triacylglycerols, fatty acids, fatty alcohols, hydrocarbons
_____________________________________________________________________________________________
INTRODUCTION
MoringaoleiferaLam.locally known as malunggayhas been used to combat malnutrition, specially among infants
and nursing mothers [1].The leaves are used for the treatment of malaria, typhoid fever, parasitic diseases, genito-
urinary ailments, hypertension, arthritis, swellings, cuts, diseases of the skin, and diabetes as well as cardiac
stimulants, contraceptive remedy, elicit lactation and to boost the immune system [2–7].
Investigation of the carotenoid contents from the leaves, flowers and fruits of eight M. oleifera cultivars from India
yielded luteoxanthin, lutein, zeaxanthin, and β-carotene. Lutein was identified as the major constituent of the leaves
and fruits accounting for 53.6 and 52.0 % of the total carotenoids, respectively [8]. Furthermore, the β-sitosterol,
total phenolic and flavonoid compounds in the leaves of M. oleifera were reported as 90 mg/g, 8 µg/mL and 27
µg/mL, respectively [9]. The leaves of M. oleifera were also reported to contain chlorophyll a, chlorophyll b,
vitamin C, carotenoids, proteins, amino acids and minerals [10]. We earlier reported the isolation of polyprenol,
phytyl fatty acid esters and lutein from the leaves of M. oleifera [11]. A review on the cultivation, genetic,
ethnopharmacology, phytochemistry and pharmacology of M. oleifera leaves has been provided [12].
We report herein the isolation of lutein (1), β-carotene (2), phytyl fatty acid ester (3), polyprenol (4), chlorophyll a
(5), β-sitosterol (6), triacylglycerols (7) (Fig. 1), fatty acids, fatty alcohols, and saturated hydrocarbons from the
leaves of M. oleifera.
Consolacion Y Ragasa et al Der Pharma Chemica, 2015, 7 (7):395-399
___________________________________________________________________________
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6
2
OH
HO 1
H
2
C
HC
OCR
OCR'
H
2
C OCR"
O
O
O
7 R, R', R" = long chain fatty acid
HO
1
3
6
10
11
14
17
18
19
22 24
26
29
N
N
N
N
Mg
CH
3
O
CH
3
HC
H
3
C
H
H
3
CH
O
H
3
CO
5
1
1a
2
2a
alpha
delta
8
8a
7
7a
17 16
6
5
5a
9
10
10a
10b
2b
7b
7c
beta
gamma
12 13
3
3a
4
4a
4b
14
15
O
O
1' 7'3' 11' 16'
20'17' 18' 19'
OH
[
]3
[]n
4
CH
2
OCR
O
3 R = long chain fatty acid
1
3
7
11 1'
17
20
16
1
3
7915 1'
3'
7'
12'
15'
16
17
16'
18'
Fig. 1. Chemical structures of lutein (1), β-carotene (2), phytyl fatty acid ester (3), polyprenol (4), chlorophyll a (5), β-sitosterol (6),
triacylglycerols (7) from the leaves of M. oleifera Lam.
MATERIALS AND METHODS
General Experimental Procedure
NMR spectra were recorded on a Varian VNMRS spectrometer in CDCl
3
at 600 MHz for
1
H NMR and 150 MHz
for
13
C NMR spectra. Column chromatography was performed with silica gel 60 (70-230 mesh). Thinlayer
Consolacion Y Ragasa et al Der Pharma Chemica, 2015, 7 (7):395-399
___________________________________________________________________________
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chromatography was performed with plastic backed plates coated with silica gel F
254
and the plates were visualized
by spraying with vanillin/H
2
SO
4
solution followed by warming.
Sample Collection
The sample was collected from Laurel, Batangas, Philippines on September 4, 2014. The sample was authenticated
as Moringa oleifera Lam. by one of the authors (MPM).
General Isolation Procedure
A glass column 18 inches in height and 1.0 inches internal diameter was packed with silica gel. The crude extract
from the twigs were fractionated by silica gel chromatography using increasing proportions ofacetone in
dichloromethane (10% increment) as eluents. Fifty milliliter fractions were collected. All fractions were monitored
by thin layer chromatography. Fractions with spots of the same R
f
values were combined andrechromatographed in
appropriate solvent systems until TLC pure isolates were obtained. A glass column 12inches in height and 0.5 inch
internal diameter was used for the rechromatography. Two milliliter fractions were collected. Final purifications
were conducted using Pasteur pipettes as columns. One milliliter fractions were collected.
Isolation of the Chemical Constituents of the Leaves
Fresh leaves (14.2 kg) of Moringa oleifera were air-dried for about 1 week to afford 2.65 kg of dried leaves which
were soaked in EtOH at room temperature for 3 days and then filtered. The filtrate was concentrated under vacuum
to afford a crude extract (218 g). The crude EtOH extract (10 g) was chromatographed using increasing proportions
of acetone in CH
2
Cl
2
at 10% increment by volume. The CH
2
Cl
2
and 10% acetone in CH
2
Cl
2
fractions were
combined and rechromatographed using petroleum ether, followed by 1% EtOAc in petroleum ether, and finally
2.5% EtOAc in petroleum ether. The fractions eluted with petroleum ether were rechromatographed using
petroleum ether to yield saturated hydrocarbons (15 mg). The fractions eluted with 1% EtOAc in petroleum ether
were combined and rechromatographed (2 ×) using 2.5% EtOAc in petroleum ether to afford 2 (3 mg) after washing
with petroleum ether. The fractions eluted with 2.5% EtOAc in petroleum ether were combined and
rechromatographed (3 ×) using 5% EtOAc in petroleum ether to yield 3 (4 mg). The 20% to 30% acetone in CH
2
Cl
2
fractions were combined and rechromatographed using 5% EtOAc in petroleum ether, followed by 7.5% EtOAc in
petroleum ether, and finally 10% EtOAc in petroleum ether. The fractions eluted with 5% EtOAc in petroleum ether
were combined and rechromatographed (2 ×) using 7.5% EtOAc in petroleum ether to afford 4 (5 mg). The
fractions eluted with 7.5% EtOAc in petroleum ether were combined and rechromatographed using the same solvent
to afford 7 (6 mg). The fractions eluted with 10% EtOAc in petroleum ether were combined and rechromatographed
using the same solvent to afford fatty alcohols (4 mg). The 40% to 60% acetone in CH
2
Cl
2
fractions were combined
and rechromatographed using CH
2
Cl
2
. The less polar fractions were combined and rechromatographed (3×) using
15% EtOAc in petroleum ether to afford 6 (2 mg) after washing with petroleum ether. The more polar fractions
were combined and rechromatographed(4 ×) using 20% EtOAc in petroleum ether yield5 (10 mg) after washing
with petroleum ether, followed by Et
2
O. The 70% to 80% acetone in CH
2
Cl
2
fractions were combined and
rechromatographed using CH
3
CN:Et
2
O:CH
2
Cl
2
(0.5:0.5:9, v/v). The less polar fractions were rechromatographed
using CH
3
CN:Et
2
O:CH
2
Cl
2
(0.5:0.5:9, v/v) to afford fatty acids (7 mg). The more polar fractions were combined
and rechromatographed (3 ×) using CH
3
CN:Et
2
O:CH
2
Cl
2
(1:1:8, v/v) to afford 1 (12 mg) after washing with
petroleum ether, followed by Et
2
O.
Lutein(1):
13
C NMR (150 MHz, CDCl
3
): δ 12.81, 13.10, 21.61, 22.86, 24.25, 28.72, 29.49, 30.25, 34.02, 37.11,
42.52, 44.61, 48.39, 54.94, 65.10, 65.94, 124.43, 124.79, 124.92, 125.57, 126.14, 128.71, 130.03, 130.07, 130.79,
131.29, 132.56, 135.06, 135.68, 136.48, 137.56, 137.74, 138.01, 138.49.
β-Carotene (2):
1
H NMR (600 MHz, CDCl
3
): δ 6.09-6.64 (CH=), 1.01 (12H, s, CH
3
), 1.95 (12H, s, allylic CH
3
),
1.69 (6H, s, allylic CH
3
).
Phytyl fatty acid ester (3):
13
C NMR (150 MHz, CDCl
3
): δ 61.21 (C-1), 118.12 (C-2), 142.64 (C-3), 39.85 (C-4),
25.03 (C-5), 36.63 (C-6), 32.67 (C-7), 37.35 (C-8), 24.46 (C-9), 37.42 (C-10), 32.78 (C-11), 37.28 (C-12), 24.79 (C-
13), 39.36 (C-14), 27.97 (C-15), 22.71 (C-16), 16.36 (C-17), 19.74, 19.70 (C-18, C-19), 22.62 (C-20),173.95 (C-1'),
34.40 (C-2'), 25.03 (C-3'), 29.59 (C-4'), 29.11-29.69 (CH
2
')
n
, 31.92 (CH
2
'), 29.59 (CH
2
'), 14.12 (CH
3
'-terminal).
Polyprenol (4):
1
H NMR (600 MHz, CDCl
3
): δ 4.07 (2H, d, J = 7.2 Hz, CH
2
OH), 5.42 (1H, =CH), 5.07-5.11
(11H,=CH), 1.94-2.07 (40H, allylic CH
2
), 1.73 (3H, allylic CH
3
), 1.66 (21H, allylic CH
3
), 1.59 (12H, allylic CH
3
).
Consolacion Y Ragasa et al Der Pharma Chemica, 2015, 7 (7):395-399
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Chlorophyll a (5):
13
C NMR (150 MHz, CDCl
3
): δ 131.85 (C-1),12.12 (C-1a), 136.51 (C-2),129.05 (C-2a),122.79
(C-2b),136.17 (C-3), 11.23 (C-3a), 145.23 (C-4), 19.46 (C-4a), 17.42 (C-4b), 137.93 (C-5),12.12 (C-5a), 129.05 (C-
6), 51.11 (C-7), 29.79 (C-7a), 31.16 (C-7b),172.94 (C-7c), 50.10 (C-8), 23.06 (C-8a), 189.65 (C-9), 64.68 (C-10),
169.60 (C-10a), 52.84 (C-10b), 142.84 (C-11), 136.28 (C-12), 155.66 (C-13), 150.98 (C-14), 129.09 (C-15), 149.64
(C-16), 161.23 (C-17), 172.94 (C-18), 97.54 (C-α), 104.44 (C-β), 105.21 (C-γ), 93.12 (C-δ), 61.45 (1'), 117.68 (2'),
142.03 (3'), 39.77 (4'), 24.96 (5'), 36.62 (6'), 32.60 (7'), 37.30 (8'), 24.40 (9'), 37.37 (10'), 32.74 (11'), 37.24 (12'),
24.75 (13'), 39.33 (14'), 27.94 (15'), 22.70 (16'), 16.27 (17'), 19.63 (18'), 19.70 (19'), 22.60 (20').
β-Sitosterol (6):
1
H NMR (600 MHz, CDCl
3
): δ 3.50 (m, H-3), 2.26, 2.21 (H
2
-4), 5.33 (dd, J = 5.0, 2.0 Hz, H-6),
0.66 (s, CH
3
-18), 0.99 (s, CH
3
-19), 0.90 (d, J = 7.2 Hz, CH
3
-21), 0.79 (d, J = 7.2 Hz, CH
3
-26), 0.82 (d, J = 7.2
Hz,CH
3
-27), 0.84 (t, J = 7.2 Hz, CH
3
-29).
Triacylglycerols (7):
13
C NMR (150 MHz, CDCl
3
): δ 62.08 (glyceryl CH
2
), 68.86 (glyceryl CH), 173.30, 173.26
(C=O α), 172.84 (C=O β), 34.01, 34.04, 34.18 (C-2), 20.54, 22.56, 22.68, 24.82, 24.85, 25.51, 25.60, 25.62, 27.16,
27.19, 27.21, 29.04, 29.07, 29.11, 29.17, 29.19, 29.27, 29.31, 29.34, 29.35, 29.47, 29.52, 29.58, 29.62, 29.65, 29.70,
29.76, 31.52, 31.90, 31.91 (CH
2
), 131.95, 130.22, 130.20, 130.00, 129.98, 129.70, 129.67, 128.28, 128.23,128.21,
128.06, 128.05, 127.88, 127.87, 127.75, 127.73, 127.09 (CH=CH), 14.07, 14.11, 14.27 (terminal CH
3
).
Fatty acids:
1
H NMR (600 MHz, CDCl
3
): δ 5.34 (m, =CH), 2.79 (t, J = 6.6 Hz, double allylic CH
2
), 2.75 (t, J = 6.6
Hz, double allylic CH
2
), 2.33 (t, J = 7.2 Hz, α-CH
2
), 2.03-2.06 (m, allylic CH
2
), 1.56-1.64 (m, β-CH
2
), 1.22-1.35
(CH
2
), 0.96 (t, J = 7.2 Hz, terminal CH
3
), 0.86 (t, J = 7.2 Hz, terminal CH
3
).
Fatty Alcohols:
1
H NMR (600 MHz, CDCl
3
): δ 3.62 (t, J = 7.2 Hz, terminal CH
2
OH), 1.55 (m, α-CH2), 1.23-1.29
(br s, CH
2
), 0.86 (t, J = 7.2 Hz, terminal CH
3
).
Hydrocarbons:
1
H NMR (600 MHz, CDCl
3
): δ 1.23 (br s, CH
2
), 0.86 (t, J = 7.2 Hz, terminal CH
3
).
RESULTS AND DISCUSSION
Silica gel chromatography of the dichloromethane extract of the air dried leaves of M. oleifera yieldedlutein (1) [13],
β-carotene (2) [14], phytyl fatty acid ester (3) [15], polyprenol (4) [16], chlorophyll a (5) [17], β-sitosterol (6) [18],
triacylglycerols (7) [19], fatty acids [14], fatty alcohols [20], and saturated hydrocarbons [21]. The structures of
these compounds were identified by comparison of their
1
H or
13
CNMR data with those reported in the literature. α-
Linolenic acid was deduced as one of the fatty acids from the resonances for the methyl triplet at δ 0.96 (t, J = 7.2
Hz), the double allylic methylenes at δ 2.79 (t, J = 6.6 Hz) and the olefinic protons at δ 5.34 (m) [22]. A small
amount of linoleic acid was detected from the low intensity resonance for a double allylic methylene at δ 2.75 [22],
while another unsaturated fatty acid, oleic acid was suggested by the high intensity resonance for allylic methylene
protons at δ 2.03-2.06 [23]. The fatty acids attached to the triacylglycerols are α-linolenic acid, linoleic acid, and
oleic acid as deduced from the aforementioned resonances.
Acknowledgement
Research grants from the De La Salle University Science Foundation through the University Research Coordination
Office and the University Research Office of De La Salle UniversityDasmariñas are gratefully acknowledged.
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... The NMR data of 2 and 3 were in accordance with the data reported in the literature for cinnamic acid [17] and saturated long-chain hydrocarbons [18], respectively. ...
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Calyptothecium ramosii Broth. of the moss family Pterobyaceae is a species indigenous to the Philippines. Chemical investigation of the dichloromethane extract of C. ramosii has led to the isolation of γ-polypodatetraene (1), cinnamic acid (2) and saturated long-chain hydrocarbons (3). The structure of 1 was elucidated by extensive 1D and 2D nuclear magnetic resonance spectroscopy (NMR) and confirmed by comparison of its NMR data with literature data. The structures of 2 and 3 were identified by comparison of their NMR data with literature data. Abstract Calyptothecium ramosii Broth. ialah lumut dari famili Pterobyaceace merupakan spesies asli bagi Filipina. Kajian juzuk kimia dilakukan ke atas ekstrak C. ramosii menggunakan diklorometana untuk memisahkan γ-polipodatetraen (1), asid sinamik (2) dan hidrokarbon tepu rantaian panjang (3). Struktur 1 telah dicirikan melalui spektroskopi nuklear magnetik resonan 1D dan 2D dan ditentusahkan melalui perbandingan data kajian literatur dan data NMR.
... , 6, 7, 8, 14, 15, 16, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 31, 33, 35, 37, 38 v Aleurites moluccanus (L.) Willd. 4 4, 11, 23, 24, 25 Morinda citrifolia L. 6 1, 7,8,9,10,11,14,15,16,17,29,31,34 Sources: market survey and literature study (Al-Dhubiab 2012;Ramakhrisna et al. 2014;Ragasa et al. 2015;Assi et al. 2017;Goswami et al. 2017;Irawan et al. 2017) ...
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Hidayat S, Zuhud EAM, Widyatmoko D, Bahruni, Batubara I. 2021. The commercial potential of forest trees as medicinal and health ingredients. Biodiversitas 22: 2795-2804. Indonesian forests contain many trees that belong to medicinal plants classified as non-timber forest products (NTFP). Although these plants have been used from generation to generation by several ethnic groups and even some of them have become commercial goods, many species have not received special attention in terms of their cultivation. This study aimed to explore the commercial value of forest trees as medicinal ingredients and obtain a recommended ranking for their cultivation. The method used was market surveys to herbal stores and questionnaires to experts related to medicinal plants. The results showed that there are 59 species of forest trees used as medicinal ingredients and health supplements. Cinnamomum burmanni, Morinda citrifolia, and Moringa oleifera have the most diverse commercial products in drugs and health stores. These three species also have active ingredients that potentially substitute for chemical drugs. Following the advice of medicinal plant experts, these three species are also included in the ten species recommended for immediate cultivation.
... He also reported that flowers contain sucrose, amino acids, alkaloids, and flavonoids such as rhamnetin, isoquercitrin, and kaempferitrin. Whole pods contain isothiocyanate, thiocarbamates, and nitrile; Fruits contain cytokines, whereas seeds contain high concentrations of benzylglucosinolate.Ragasa, Medecilo, and Shen (2015) isolated lutein, β-carotene, phytyl fatty acid ester, polyprenol, chlorophyll a, β-sitosterol, triacylglycerols, fatty acids, fatty alcohols, and saturated hydrocarbons from the leaves of M. oleifera.5.1 | Biological activities of M. oleiferaPresence of high phenolic content in M. oleifera contributes to their high antioxidant activity as they stabilize radicals produced in cells by donating or accepting electrons, hence acting as antioxidants (Abd Rani et al., 2018). Different cultivars of M. oleifera had different antioxidant, phytochemical, and antimicrobial profiles. ...
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