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Chemical investigation of the dichloromethane extracts of Strongylodon macrobotrys led to the isolation of taraxerone (1), stigmasterol (2), β-sitosterol (3), and triglycerides (4) from the stems; 2, 3, and β-stigmasteryl 3-O-β-D-glucopyranoside (5) from the flowers; and polyprenol (6), lutein (7), squalene (8) and chlorophyll a (9) from the leaves. The structures of these compounds were identified by comparison of their 13C NMR data with those reported in the literature.
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Der Pharma Chemica, 2014, 6(6):366-373
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Chemical constituents of Strongylodon macrobotrys
Consolacion Y. Ragasa
1,2*
, Virgilio D. Ebajo Jr.
2
, Vincent Antonio S. Ng
2
,
Mariquit M. De Los Reyes
3,4
and Chien-Chang Shen
5
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, Taft Avenue, Manila, Philippines
3
Biology Department, De La Salle University Science & Technology Complex Leandro V. Locsin Campus, Biñan
City, Laguna, Philippines
4
Biology Department, De La Salle University, Taft Avenue, Manila, Philippines
5
National Research Institute of Chinese Medicine, 155-1, Li-Nong St., Sec. 2, Taipei, Taiwan
_____________________________________________________________________________________________
ABSTRACT
Chemical investigation of the dichloromethane extracts of Strongylodon macrobotrys led to the isolation of
taraxerone (1), stigmasterol (2), β-sitosterol (3), and triglycerides (4) from the stems; 2, 3, and β-stigmasteryl 3-O-
β-D-glucopyranoside (5) from the flowers; and polyprenol (6), lutein (7), squalene (8) and chlorophyll a (9) from
the leaves. The structures of these compounds were identified by comparison of their
13
C NMR data with those
reported in the literature.
Keywords: Strongylodon macrobotrys, Leguminosae, taraxerone, stigmasterol, β-sitosterol, β-stigmasteryl 3-O-β-
D-glucopyranoside, polyprenol, lutein, squalene, chlorophyll a
_____________________________________________________________________________________________
INTRODUCTION
Strongylodon macrobotrys A. Gray, of the family Leguminosae, commonly known as jade vine or emerald creeper
and locally known as “tayabak”, is a leguminous perennial woody vine that can reach up to 18 m in length. It is
native to the Philippines, thriving best in tropical forests, along streams or in ravines from 700 to 1,000 m asl [1, 2].
It is considered as one of the most beautiful of all tropical climbers because of its elegant and striking turquoise
flowers that dangle in mid-air when in full bloom. In the Philippines, jade vine is cultivated as an ornamental plant.
Naturally pollinated by bats, the destruction of rainforests in the Philippines threatens S. macrobotrys in the wild
resulting in the plant being listed as vulnerable in the IUCN list of threatened species [3].
There are few studies on the chemical constituents of S. macrobotrys. An earlier study reported that the major
visible pigment in the jade vine flower is the anthocyanin, malvidin 3,5-di-O-glucoside, accompanied with C-
glycosylflavones, isovitexin 7-O-glucoside and isovitexin [4]. Recently, the flower color of S. macrobotrys which is
luminous blue green was attributed to a mixture of an anthocyanin, malvin, and a flavone, saponarin, in
approximately 1:9 molar ratio [5]. The isolation and identification of two saponins, the dimethyl esters of
pseudoginsenoside-RP1 and zingibroside-R1 from the seeds of S. macrobotrys were also reported [6]. There is no
reported study on the biological activity of jade vine.
Consolacion Y. Ragasa
et al Der Pharma Chemica, 2014, 6 (6):366-373
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This study is part of our research on the chemical constituents of endemic and native Philippine ornamental plants.
Our chemical investigation of Hoya mindorensis, an endemic ornamental plant of the Philippines, led to the isolation
of lupenone and lupeol from the roots; lupeol, squalene and β-sitosterol from the leaves; and betulin from the stems
of the plant. Except for lupenone, all the isolated secondary metabolites from H. mindorensis are known anticancer
compounds [7].
We report herein the isolation and identification of taraxerone (1), a mixture of stigmasterol (2) and β-sitosterol (3)
in a 2:1 ratio, and triglycerides (4) from the stems; a mixture of 2 and 3 in a 3:1 ratio and stigmasterol-β-D-
glucoside (5) from the flowers; and polyprenol (6), lutein (7), squalene (8) and chlorophyll a (9) from the leaves
(Fig. 1) of S. macrobotrys. To the best of our knowledge this is the first report on the isolation of these compounds
from the plant.
8
9
3
HO
NN
CH
3
NN
Mg
CH
3
O
H
3
C
H
HHC
H
3
C
CO
H
3
CO
O
O
2b 2a
2
12 13
3
4
4a
4b
beta
gamma
alpha
delta
18
1
1a
8a
7
16
96
55a
14
15
817
10a
10b
7b
7c
10
11
P1 P3 P7 P11 P15 P16
P3a P7a P11a P15a
1
5
9
11 13 16
18
19
3
20
21
23 25
28
1
2
HO
CH
2
OCR
O
CHOCR'
O
CH
2
OCR"
O
4 R, R', R" = long chain fatty acids
OH
[
]
3
[
]
n
6
OH
HO
7
5
O
O
OH
HO
HOHOH
2
C
1'
3'
6'
1
359
11 14
18
20
23
25
27
28
30
1
3
6
5
13
15
1617
18
20
15'
1'
3'5'
9'
13'
18'
17'
16'
1
3
5
710
12 13
14
15
O
Fig. 1. Chemical constituents of Strongylodon macrobotrys: taraxerone (1), stigmasterol (2), β-sitosterol (3), triglycerides (4), β-
stigmasteryl 3-O-β-D-glucopyranoside (5), polyprenol (6), lutein (7), squalene (8) and chlorophyll a (9).
Consolacion Y. Ragasa
et al Der Pharma Chemica, 2014, 6 (6):366-373
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MATERIALS AND METHODS
Sample Collection
Samples of leaves, twigs and flowers of Strongylodon macrobotrys A. Gray were a generous gift collected from the
Center for Ecozoic Living and Learning (CELL), Silang, Cavite in May 2014. The samples were authenticated at
the Botany Division of the National Museum, Manila and deposited with voucher # 268-2014.
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). Thin layer
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.
General Isolation Procedure
A glass column 20 inches in height and 2.0 inches internal diameter was packed with silica gel. The crude extract
from the leaves were fractionated by silica gel chromatography using increasing proportions of acetone in
dichloromethane (10% increment) as eluents. One hundred milliliter fractions were collected. All fractions were
monitored by thin layer chromatography. Fractions with spots of the same Rf values were combined and
rechromatographed in appropriate solvent systems until TLC pure isolates were obtained. A glass column 12 inches
in height and 0.5 inch internal diameter was used for the rechromatography. Five milliliter fractions were collected.
Final purifications were conducted using Pasteur pipettes as columns. One milliliter fractions were collected.
Isolation
The air-dried stems of S. macrobotrys (40.8 g) was ground in a blender, soaked in CH
2
Cl
2
for 3 days and then
filtered. The solvent was evaporated under vacuum to afford a crude extract (1.5 g) which was chromatographed
using increasing proportions of acetone in CH
2
Cl
2
at 10% increment. The CH
2
Cl
2
fraction was rechromatographed
(3 ×) using 5% EtOAc in petroleum ether to afford 1 (5 mg) after washing with petroleum ether. The 30% acetone
in CH
2
Cl
2
fraction was rechromatographed (2 ×) in 5% EtOAc using petroleum ether to afford 4 (7 mg). The 40%
acetone in CH
2
Cl
2
fraction was rechromatographed (4 ×) using CH
3
CN:Et
2
O:CH
2
Cl
2
(0.5:0.5:9, v/v) to afford a
mixture of 2 and 3 (9 mg) after washing with petroleum ether.
The air-dried flowers of S. macrobotrys (28.5 g) were ground in a blender, soaked in CH
2
Cl
2
for 3 days and then
filtered. The solvent was evaporated under vacuum to afford a crude extract (0.15 g) which was chromatographed
using increasing proportions of acetone in CH
2
Cl
2
at 10% increment. The 40% acetone in CH
2
Cl
2
fraction was
rechromatographed (3 ×) using CH
3
CN:Et
2
O:CH
2
Cl
2
(0.5:0.5:9, v/v) to afford a mixture of 2 and 3 (5 mg) after
washing with petroleum ether. The 60% acetone in CH
2
Cl
2
was rechromatographed (5 ×) using
CH
3
CN:Et
2
O:CH
2
Cl
2
(2:2:6, v/v) to afford 5 (4 mg) after trituration with petroleum ether.
The air-dried leaves of S. macrobotrys (69.2 g) was ground in a blender, soaked in CH
2
Cl
2
for 3 days and then
filtered. The solvent was evaporated under vacuum to afford a crude extract (3.0 g) which was chromatographed
using increasing proportions of acetone in CH
2
Cl
2
at 10% increment. The CH
2
Cl
2
fraction was rechromatographed
(2 ×) using 1% EtOAc in petroleum to afford 8 (5 mg). The 20% acetone in CH
2
Cl
2
fraction was
rechromatographed (3 ×) using 12.5 % EtOAc in petroleum ether to afford 6 (6 mg). The 40% acetone in CH
2
Cl
2
fraction was rechromatographed (4 ×) using 20% EtOAc in petroleum ether to afford 9 (8 mg) after washing with
petroleum ether, followed by Et
2
O. The 60% acetone in CH
2
Cl
2
fraction was rechromatographed (5 ×) using
CH
3
CN:Et
2
O:CH
2
Cl
2
(1:1:8, v/v) to afford 7 (9 mg) after washing with petroleum ether, followed by Et
2
O.
Taraxerone (1):
1
H NMR (600MHz, CDCl
3
) δ: 5.54 (dd, J = 3.6, 8.4 Hz, H-15), 1.06 (s, H
3
-23), 1.05 (s, H
3
-24),
1.07 (H
3
-25), 0.888, 0.894 (s, H
3
-26, H
3
-30), 1.12 (s, H
3
-27), 0.81 (s, H
3
-28), 0.93 (s, H
3
-29);
13
C NMR (CDCl
3
) δ:
38.33 (C-1), 34.14 (C-2), 217.60 (C-3), 47.58 (C-4), 55.76 (C-5), 19.94 (C-6), 35.08 (C-7), 38.86 (C-8), 48.68 (C-9),
35.77 (C-10), 17.43 (C-11), 37.73, 37.67 (C-12, C-13), 157.58 (C-14), 117.18 (C-15), 36.65 (C-16), 37.52 (C-17),
48.76 (C-18), 40.61 (C-19), 28.79 (C-20), 33.55 (C-21), 33.06 (C-22), 26.08 (C-23), 21.33 (C-24), 14.80 (C-25),
29.84 (C-26), 25.56 (C-27), 29.91 (C-28), 33.34 (C-29), 21.48 (C-30).
Stigmasterol (2):
13
C NMR (150 MHz, CDCl
3
): δ 37.24 (C-1), 31.65 (C-2), 71.81 (C-3), 42.29 (C-4), 140.74 (C-5),
121.71 (C-6), 31.89 (C-7), 31.89 (C-8), 50.14 (C-9), 36.51 (C-10), 21.08 (C-11), 39.67 (C-12), 42.20 (C-13), 56.75
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(C-14), 24.35 (C-15), 28.91 (C-16), 55.94 (C-17), 12.04 (C-18), 19.39 (C-19), 40.49 (C-20), 21.08 (C-21), 138.31
(C-22), 129.26 (C-23), 51.23 (C-24), 31.89 (C-25), 21.20 (C-26), 18.97 (C-27), 25.40 (C-28), 12.25 (C-29).
β-Sitosterol (3):
13
C NMR (150 MHz, CDCl
3
): δ 37.24 (C-1), 31.65 (C-2), 71.82 (C-3), 42.29 (C-4), 140.74 (C-5),
121.71 (C-6), 31.89, 31.90 (C-7, C-8), 50.14 (C-9), 36.49 (C-10), 21.07 (C-11), 39.76 (C-12), 42.20 (C-13), 56.75
(C-14), 24.35 (C-15), 28.24 (C-16), 56.04 (C-17), 11.97 (C-18), 19.39 (C-19), 36.14 (C-20), 18.77 (C-21), 33.93 (C-
22), 26.04 (C-23), 45.82 (C-24), 29.13 (C-25), 19.02 (C-26), 19.81 (C-27), 23.05 (C-28), 11.85 (C-29).
Triglyceride (4):
13
C NMR (150 MHz, CDCl
3
): δ 62.09 (glyceryl CH
2
), 68.87 (glyceryl CH), 173.25 (C=O α),
172.84 (C=O β), 34.01, 34.05, 34.18 (C-2), 24.83, 24.86, 24.87 (C-3), 29.08 29.04 (C-4), 29.17, 29.19, 29.27 (C-5),
29.48 (C-6), 22.19 (C-8), 130.00, 129.98 (C-9), 127.87, 128.05 (C-10), 25.62, 25.52 (C-11), 127.88. 128.07 (C-12),
130.22, 128.07 (C-13), 27.19, 25.62 (C-14), 29.35 (C-15), 127.10 (C-15), 31.52 (C-16), 132.00 (C-16), 22.57, 22.69
(C-17), 14.07, 14.12 (C-18).
β-Stigmasteryl 3-O-β-D-glucopyranoside (5):
13
C NMR (150 MHz, CDCl
3
): δ 37.24 (C-1), 31.84 (C-2), 79.53 (C-
3), 42.20 (C-4), 140.25 (C-5), 122.17 (C-6), 31.84, 31.87 (C-7, C-8), 50.15 (C-9), 36.72 (C-10), 19.81 (C-11), 38.88
(C-12), 42.30 (C-13), 56.83 (C-14), 24.34 (C-15), 28.91 (C-16), 55.94 (C-17), 11.84 (C-18), 18.77 (C-19), 39.64 (C-
20), 20.04 (C-21), 138.28 (C-22), 129.29 (C-23), 51.23 (C-24), 31.84 (C-25), 19.34 (C-26), 18.97 (C-27), 24.98 (C-
28), 12.26 (C-29), 101.18 (C-1'), 73.99 (C-2'), 76.79 (C-3'), 69.98 (C-4'), 76.79 (C-5'), 63.10 (C-6').
Polyprenol (6):
13
C NMR (150 MHz, CDCl
3
): δ 59.01 (CH
2
OH), 139.90, 136.08, 135.37, 135.28, 135.24, 135.20,
134.93, 134.86, 131.25, 125.01, 124.99, 124.99, 124.92, 124.39, 124.31, 124.24, 124.21, 124.11, 39.71, 32.21,
32.19, 31.97, 26.75, 26.66, 26.62, 26.39, 26.32, 25.68, 23.45, 23.42, 23.37, 17.66, 15.99, 15.98.
Lutein (7):
13
C NMR (150 MHz, CDCl
3
): δ 37.12 (C-1), 48.42 (C-2), 65.10 (C-3), 42.55 (C-4), 126.15 (C-5),
138.01 (C-6), 125.57 (C-7), 138.49 (C-8), 135.69 (C-9), 131.29 (C-10), 124.93 (C-11), 137.56 (C-12), 136.41 (C-
13), 132.57 (C-14), 130.08 (C-15), 28.72 (C-16), 30.26 (C-17), 21.62 (C-18), 12.81, 12.75 (C-19, C-20), 34.02 (C-
1'), 44.22 (C-2'), 65.93 (C-3'), 124.45 (C-4'), 137.72 (C-5'), 54.96 (C-6'), 128.72 (C-7'), 130.80 (C-8'), 135.07 (C-9'),
137.56 (C-10'), 124.80 (C-11'), 137.72 (C-12'), 136.49 (C-13'), 132.57 (C-14'), 130.08 (C-15'), 28.28 (C-16'), 29.49
(C-17'), 22.87 (C-18'), 12.81, 3.11 (C-19'), 12.81 (C-20').
Squalene (8):
13
C NMR (150 MHz, CDCl
3
): δ 25.69 (C-1, C-1'), 131.24 (C-2, 2'), 124.30 (C-3, C-3'), 26.66 (C-4, C-
4'), 39.73 (C-5, C-5'), 134.89 (C-6, C-6'), 124.40 (C-7, C-7'), 26.76 (C-8, C-8'), 39.75 (C-9, C-9'), 135.10 (C-10, C-
10'), 124.30 (C-11, C-11'), 28.27 (C-12, C-12'), 17.67 (C-13, C-13'), 16.03 (C-14, C-14'), 15.99 (C-15, C-15').
Chlorophyll a (9): dark green crystals.
13
C NMR (150 MHz, CDCl
3
): δ 131.85 (C-1), 12.12 (C-1a), 136.51 (C-2),
129.06 (C-2a), 122.80 (C-2b), 136.18 (C-3), 11.24 (C-3a), 145.24 (C-4), 19.47 (C-4a), 17.43 (C-4b), 137.93 (C-5),
12.12 (C-5a), 129.06 (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), 136.18 (C-12), 155.66 (C-13), 150.99
(C-14), 129.10 (C-15), 149.65 (C-16), 161.24 (C-17), 172.94 (C-18), 97.55 (C-α), 104.44 (C-β), 105.22 (C-γ), 93.12
(C-δ), 61.45 (P-1), 117.69 (P-2), 142.02 (P-3), 16.27 (P-3a), 39.77 (P-4), 24.96 (P-5), 36.62 (P-6), 32.60 (P-7), 19.64
(P-7a), 37.30 (P-8), 24.40 (P-9), 37.37 (P-10), 32.74 (P-11), 19.70 (P-11a), 37.24 (P-12), 24.76 (P-13), 39.33 (P-14),
27.95 (P-15), 22.60 (P-15a), 22.70 (P-16).
RESULTS AND DISCUSSION
Silica gel chromatography of the dichloromethane extract of S. macrobotrys afforded taraxerone (1) [8], a mixture of
stigmasterol (2) [9] and β-sitosterol (3) [10] in a 2:1 ratio, and triglycerides (4) [11] from the stems; a mixture of 2
and 3 in a 3:1 ratio and stigmasterol-β-D-glucoside (5) [12] from the flowers; and polyprenol (6) [13], lutein (7)
[14], squalene (8) [15] and chlorophyll a (9) [16] from the leaves. The ratios of the mixture of 2 and 3 were deduced
from the integrations of the
1
H NMR resonances for the olefinic protons of 2 at δ 5.33 (dd, J = 1.8, 4.8 Hz, H-6),
5.13 (dd, J = 9.0, 15.0 Hz, H-22) and 5.00 (dd, J = 9.0, 15.0 Hz, H-23) and 3 at δ 5.33 (dd, J = 1.8, 4.8 Hz, H-6).
The fatty acids esterified to the glycerol in the triglycerides are linolenic acid, linoleic acid and saturated fatty acid.
These were deduced from the integration of the resonances at δ 0.95 (t, J = 7.8 Hz, CH
3
) and 2.76 (2 double allylic
CH
2
) for the linolenic acid; δ 0.88 (t, J = 6.6 Hz, CH
3
) and 2.74 (double allylic CH
2
) for the linoleic acid; and δ 0.86
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(t, J = 7.2 Hz, CH
3
) for the saturated fatty acid. The structures of 1-9 were identified by comparison of their
13
C
NMR data with those reported in the literature [8-16].
Although no biological activity tests were conducted on the isolated compounds (1-9), literature search revealed that
these have diverse bioactivities as follows.
Taraxerone (1) was reported to exhibit antioxidant activity with IC
50
values of 102.34±1.53 µM and 1,763.81±12.63
µM/mL by the DPPH and ferric reducing ability of plasma assays, respectively [17]. Another study reported that 1
exhibited the highest giardicidal activity (IC
50
= 11.33 µg/mL) against Giardia lamblia trophozoites among the
samples tested [18]. Moreover, 1 enhances alcohol oxidation via increases of alcohol dehydrogenase (ADH) and
acetaldehyde dehydrogenase (ALDH) activities and gene expressions [19]. It also showed in vitro anti-leishmanial
activity against promastigotes of Leishmania donovani (strain AG 83) and anti-tumour activity on K562 leukemic
cell line [20]. It was also reported to exhibit weak antiviral activity against herpes simplex virus (type I and II) [21].
Stigmasterol (2) shows therapeutic efficacy against Ehrlich ascites carcinoma bearing mice while conferring
protection against cancer induced altered physiological conditions [22]. It lowers plasma cholesterol levels, inhibits
intestinal cholesterol and plant sterol absorption, and suppresses hepatic cholesterol and classic bile acid synthesis in
Winstar as well as WKY rats [23]. Other studies reported that stigmasterol showed cytostatic activity against Hep-2
and McCoy cells [24], markedly inhibited tumour promotion in two stage carcinogenesis experiments [25],
exhibited antimutagenic [26], topical anti-inflammatory [27], anti-osteoarthritic [28] and antioxidant [29] activities.
β-Sitosterol (3) was reported to exhibit growth inhibitory effects on human breast MCF-7 and MDA-MB-231
adenocarcinoma cells [30]. It was shown to be effective for the treatment of benign prostatic hyperplasia [31]. It
attenuated β-catenin and PCNA expression, as welll as quenched radical in-vitro, making it a potential anticancer
drug for colon carcinogenesis [32]. It was reported to induce apoptosis mediated by the activation of ERK and the
downregulation of Akt in MCA-102 murine fibrosarcoma cells [33]. It can inhibit the expression of NPC1L1 in the
enterocytes to reduce intestinal cholesterol uptake [34].
Triglycerides (4) exhibited antimicrobial activity against S. aureus, P. aeruginosa, B. subtilis, C. albicans, and T.
mentagrophytes [35]. Another study reported that triglycerides showed a direct relationship between toxicity and
increasing unsaturation, which in turn correlated with increasing susceptibility to oxidation [36]. Linoleic acid
which is one of the fatty acids esterified to 4 belongs to the omega-6 fatty acids. It was reported to be a strong
anticarcinogen in a number of animal models. It reduces risk of colon and breast cancer [37] and lowers
cardiovascular disease risk and inflammations [38]. Linolenic acid which is another fatty acid esterified to 4
belongs to omega-3 fatty acid. A previous study reported that α-linolenic acid (ALA) inhibited the human renal cell
carcinoma (RCC) cell proliferation [39]. Another study reported that apoptosis of hepatoma cells was induced by the
α-linolenic acid enriched diet which correlated with a decrease in arachidonate content in hepatoma cells and
decreased cyclooxygenase-2 expression [40]. γ-Linolenic acid (GLA) and α-linolenic acid (ALA) exhibited greater
than 90% cytotoxicity between 500 µM and 1 mM against all but two malignant micro-organ cultures tested in 5-
10% serum. GLA and ALA killed tumor at concentrations of 2 mM and above in tests using 30-40% serum [41].
β-Stigmasteryl 3-O-β-D-glucopyranoside (5) was reported as an auxin synergist which promoted markedly the
elongation of Avena coleoptile segments induced by indole acetic acid (IAA) [42]. β-Sitosteryl and stigmasteryl
glucosides were reported as selective DNA polymerase β lyase inhibitors and also potentiators of bleomycin
cytotoxicity in the A549 human lung cancer cell line [43]. The antiproliferative test showed growth inhibition of
human leukemic cell lines (NB4, HT93A, Kasumi and K562) by a fraction containing β-sitosteryl and stigmasteryl
glucosides as major compounds, with IC
50
values of 22.68, 31.54, 28.88 and 47.72 µg/mL, respectively [44].
Saponin 5 revealed only marginal antifungal activity against R. solani (25%) and P. ultimum (50%) at dose 10 mg
/disk [45].
Polyprenols (6) act as co-enzymes of membrane active transport systems for polysaccharides, peptidoglycans and
carbohydrate containing biopolymers [46]. Polyprenols from Ginkgo biloba L showed hepatoprotective effects
against CCl
4
-induced hepatotoxicity in rats [47] and exhibited antitumor activity [48]. The antidyslipidemic activity
of polyprenols from Coccinia grandis in high-fat diet-fed hamster model was also reported [49].
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Dietary lutein (7), especially at 0.002%, inhibited tumor growth by selectively modulating apoptosis, and by
inhibiting angiogenesis [50]. Another study reported that the chemopreventive properties of all-trans retinoic acid
and lutein may be attributed to their differential effects on apoptosis pathways in normal versus transformed
mammary cells [51]. Moreover, very low amounts of dietary lutein (0.002%) can efficiently decrease mammary
tumor development and growth in mice [52]. Another study reported that lutein and zeaxanthine reduces the risk of
age related macular degeneration [53].
Squalene (8) was reported to significantly suppress colonic ACF formation and crypt multiplicity which
strengthened the hypothesis that it possesses chemopreventive activity against colon carcinogenesis [54]. It showed
cardioprotective effect which is related to inhibition of lipid accumulation by its hypolipidemic properties and/or its
antioxidant properties [55]. A recent study reported that tocotrienols, carotenoids, squalene and coenzyme Q10 have
anti-proliferative effects on breast cancer cells [56]. The preventive and therapeutic potential of squalene containing
compounds on tumour promotion and regression have been reported [57]. A recent review on the bioactivities of
squalene has been provided [58].
Chlorophyll a (9) and its various derivatives are used in traditional medicine and for therapeutic purposes [59].
Natural chlorophyll and its derivatives have been studied for wound healing [60], anti-inflammatory properties [61],
control of calcium oxalate crystals [62], utilization as effective agents in photodynamic cancer therapy [63-65], and
chemopreventive effects in humans [66, 67]. A review on digestion, absorption and cancer preventive activity of
dietary chlorophyll has been provided [68].
CONCLUSION
S. macrobotrys is a native Philippine ornamental plant with no reported biological activity. Our chemical
investigation of the stems, flowers and leaves of the plant yielded compounds with diverse biological activities. All
the compounds (1-9) isolated from the different parts of the plant were reported to exhibit anticancer properties.
Acknowledgement
The authors gratefully acknowledge a research grant from the De La Salle University Science Foundation through
the University Research Coordination office and the Center for Ecozoic Living and Learning (CELL) in Silang,
Cavite, Philippines for the samples used in this study.
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To investigate the chemical constituents of the stems, leaves and roots of Euphorbia hirta, and to test for the cytotoxic and antimicrobial potentials of the major constituents of the plant. The compounds were isolated by silica gel chromatography and their structures were elucidated by NMR spectroscopy. The cytotoxicity tests were conducted using the 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay, while the antimicrobial tests employed the agar well method. The air-dried stems of E. hirta afforded taraxerone 1, a mixture of 25-hydroperoxycycloart-23-en-3β-ol (2a) and 24-hydroperoxycycloart-25-en-3β-ol (2b) (sample 2) in a 2 : 1 ratio, and another mixture of cycloartenol (3a), lupeol (3b), α-amyrin (3c) and β-amyrin (3d) (sample 3) in a 0.5 : 4 : 1 : 1 ratio. The air-dried leaves of E. hirta yielded sample 2 in a 3 : 2 ratio, sample 3 in a 2 : 3 : 1 : 1 ratio, phytol and phytyl fatty acid ester, while the roots afforded sample 2 in a 2 : 1 ratio, sample 3 in a 2 : 1 : 1 : 1 ratio, a mixture of cycloartenyl fatty acid ester 4a, lupeol fatty acid ester 4b, α-amyrin fatty acid ester 4c and β-amyrin fatty acid ester 4d (sample 4) in a 3 : 2 : 1 : 1 ratio, linoleic acid, β-sitosterol and squalene. Compound 1 from the stems, sample 2 from the leaves, and sample 3 from the stems were assessed for cytotoxicity against a human cancer cell line, colon carcinoma (HCT 116). Sample 2 showed good activity with an IC50 value of 4.8 μg·mL(-1), while 1 and sample 3 were inactive against HCT 116. Sample 2 was further tested for cytotoxicity against non-small cell lung adenocarcinoma (A549). It showed good activity against this cell line with an IC50 value of 4.5 μg·mL(-1). Antimicrobial assays were conducted on 1 and sample 2. Results of the study indicated that 1 was active against the bacteria: Pseudomonas aeruginosa and Staphylococcus aureus, but was inactive against Escherichia coli and Bacillus subtilis. Sample 2 was active against the bacteria: Pseudomonas aeruginosa, Staphylococcus aureus and Escherichia coli and fungi: Candida albicans and Trichophyton mentagrophytes. It was inactive against Bacillus subtilis and Aspergillus niger. The triterpenes: 2a, 2b, 3a, 3b, 3c and 3d were obtained from the stems, roots and leaves of E. hirta. Taraxerol (1) was only isolated from the stems, the leaves yielded phytol and phytyl fatty acid esters, while the roots afforded 4a-4d, linoleic acid, β-sitosterol, and squalene. Triterpene 1 and sample 2 were found to exhibit antimicrobial activities. Thus, these compounds are some of the active principles of E. hirta which is used in wound healing and the treatment of boils. The cytotoxic properties of sample 2 imply that triterpenes 2a and 2b contribute to the anticancer activity of E. hirta.
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A pentacyclic triterpenoid compound was isolated from the ethyl acetate extract of sedum (Sedum sarmentosum) and identified as d-friedoolean-13-en-3-one (taraxerone) by GC-MS and crystallographic analysis. The extraction yield of taraxerone was 74.12±0.57 mg/kg sedum (dry weight). The IC50 values of taraxerone were 102.34±1.53 μM and 1,763.81±12.63 μM/mL (Trolox equivalent) by the DPPH and ferric reducing ability of plasma (FRAP) assays, respectively. Taraxerone exhibited comparable antioxidant capacities with butylated hydroxytoluene (BHT) by the DPPH (p=0.117) and FRAP (p= 0.179) assays. The production of inducible nitric oxide in lipopolysaccharide-stimulated murine macrophage was inhibited by taraxerone (IC50=38.49±3.77 μM) via downregulation of inducible nitric oxide synthase (iNOS) expression at the transcriptional level. The inhibitory effect of taraxerone on nitric oxide generation was significantly more effective than that of caffeic acid and/or gallic acid.
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The flower colour of Strongyledon macrobotrys is luminous blue green and attracts bats for pollination. The chemical basis for development of the flower colour was investigated. The flower contained an anthocyanin (malvin) and a flavone (saponarin), approximately 1:9 (malvin: saponarin) in molar ratio. The pH of the pigmented epidermal cell sap of the jade vine petal was exceptionally high, 7.90, while the pH value of the colourless inner tissue was 5.60. Copigmentation test using the mixtures of malvin and saponarin (1:9 M ratio) at various pH values revealed that the characteristic blue green colour of the jade vine is developed by copigmentation of malvin with saponarin in slightly alkaline cell sap, pH 7.9. In the copigmentation in slightly alkaline condition, saponarin shows a strong yellow colour, which gives a greenish tone to the flower colour.