ArticlePDF Available

Studies on the chemical constituents of Phyllanthus emblica

Authors:

Abstract and Figures

Phytochemical investigations on Phyllanthus emblica have resulted in the isolation of the two new flavonoids, kaempferol-3-O-alpha-L-(6''-methyl)-rhamnopyranoside (1) and kaempferol-3-O-alpha-L-(6''-ethyl)-rhamnopyranoside (2). Their structures were determined on the basis of extensive spectroscopic studies including 2D-NMR experiments.
Content may be subject to copyright.
PLEASE SCROLL DOWN FOR ARTICLE
This article was downloaded by:
[PERI Pakistan]
On:
28 June 2010
Access details:
Access Details: [subscription number 909589956]
Publisher
Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 37-
41 Mortimer Street, London W1T 3JH, UK
Natural Product Research
Publication details, including instructions for authors and subscription information:
http://www.informaworld.com/smpp/title~content=t713398545
Studies on the chemical constituents of <i>Phyllanthus emblica</i>
Habib-ur-Rehman
a
; Khawaja Ansar Yasin
a
; Muhammad Aziz Choudhary
a
; Naeem Khaliq
a
; Atta-ur-
Rahman
b
; Muhammad Iqbal Choudhary
b
; Shahid Malik
b
a
Department of Chemistry, University of Azad Jammu and Kashmir, Muzaffarabad, Pakistan
b
H. E. J.
Research Institute of Chemistry, University of Karachi, Karachi, Pakistan
To cite this Article Habib-ur-Rehman, Yasin, Khawaja Ansar , Choudhary, Muhammad Aziz , Khaliq, Naeem , Atta-ur-
Rahman, Choudhary, Muhammad Iqbal and Malik, Shahid(2007) 'Studies on the chemical constituents of <i>Phyllanthus
emblica</i>', Natural Product Research, 21: 9, 775 — 781
To link to this Article: DOI: 10.1080/14786410601124664
URL: http://dx.doi.org/10.1080/14786410601124664
Full terms and conditions of use: http://www.informaworld.com/terms-and-conditions-of-access.pdf
This article may be used for research, teaching and private study purposes. Any substantial or
systematic reproduction, re-distribution, re-selling, loan or sub-licensing, systematic supply or
distribution in any form to anyone is expressly forbidden.
The publisher does not give any warranty express or implied or make any representation that the contents
will be complete or accurate or up to date. The accuracy of any instructions, formulae and drug doses
should be independently verified with primary sources. The publisher shall not be liable for any loss,
actions, claims, proceedings, demand or costs or damages whatsoever or howsoever caused arising directly
or indirectly in connection with or arising out of the use of this material.
Natural Product Research, Vol. 21, No. 9, 20 July 2007, 775–781
Studies on the chemical constituents of Phyllanthus emblica
HABIB-UR-REHMAN*y, KHAWAJA ANSAR YASINy, MUHAMMAD
AZIZ CHOUDHARYy, NAEEM KHALIQy, ATTA-UR-RAHMANz,
MUHAMMAD IQBAL CHOUDHARYz and SHAHID MALIKz
yDepartment of Chemistry, University of Azad Jammu and Kashmir,
Muzaffarabad-13100, Pakistan
zH. E. J. Research Institute of Chemistry, University of Karachi,
Karachi-75270, Pakistan
(Received 17 November 2006; in final form 15 February 2007)
Phytochemical investigations on Phyllanthus emblica have resulted in the isolation of the
two new flavonoids, kaempferol-3-O--
L-(6
00
-methyl)-rhamnopyranoside (1) and kaempferol-
3-O--
L-(6
00
-ethyl)-rhamnopyranoside (2). Their structures were determined on the basis of
extensive spectroscopic studies including 2D-NMR experiments.
Keywords: Phyllanthus emblica; HMQC interactions; Euphorbiaceae; Amla
1. Introduction
Phyllanthus emblica Linn. a monoecious glabrous or pubescent deciduous tree belongs
to the family Euphorbiaceae. The plant is commonly known as Amla and found
throughout plains of Pakistan at an elevation of 610–1390 m above the sea level.
Various species of the genus including P. emblica possess pharmaceutical properties and
are commonly used to cure various ailments [1–7]. Every part of the plant is useful in
antidotal treatment of snakebite and scorpion-sting. The fruits of the plant are known
to be a rich source of vitamin C and are frequently used in making pickles, preserves
and jellies. The formulation of the ripe fruits find therapeutic use in the ‘sidha’ system of
indian medicine [8]. The leaves are used in aphrodisiac, antipyretic, useful in biliousness,
asthma, bronchitis, leucorrhoea and vomiting. The leaves are also used in cases of
chronic dysentery and are also considered as a bitter tonic. Antithermic lotions have
also been prepared from leaves of the plant. The roots, the bark and the ripe fruit are
astringent. The flowers are refrigerant and aperient. The unripe fruit is cooling, diuretic
and laxative. The exudation from the incisions on the fruit is used as an external
application in inflammation of eye. The juice of the fresh bark with honey and turmeric
is given in gonorrhoea. The decoction of the roots given in myalgia following upon
some febrile condition. The extract of the plant also showed antioxidant and
*Corresponding author. Email: drhabib56@yahoo.com
Natural Product Research
ISSN 1478-6419 print/ISSN 1029-2349 online ß 2007 Taylor & Francis
http://www.tandf.co.uk/journals
DOI: 10.1080/14786410601124664
Downloaded By: [PERI Pakistan] At: 09:50 28 June 2010
antiatheroscleotic activities [9]. The plant contains a variety of structures [10–12], some
of which proved to be physiologically active [13–17].
Our investigations on ethanolic extract of the plant have resulted in the isolation of
kaempferol-3-O--
L-(6
00
-methyl)-rhamnopyranoside (1) and kaempferol-3-O--L-
(6
00
-ethyl)-rhamnopyranoside (2). The structures of the compounds were determined
on the basis of spectroscopic data including the 2D-NMR experiments.
2. Results and discussion
Kaempferol-3-O-a-
L-(6
00
-methyl)-rhamnopyranoside (1): The mass spectrum of com-
pound (1) showed the molecular ion at m/z 432.1034, corresponding to the molecular
formula C
21
H
20
O
10
, indicating 12
of unsaturation in the molecule. The other major
fragmentation peaks were found to be at m/z 431, 415, 391, 367, 340, 339, 325, 286, 285,
269, 255, 227, 211, 183 and 163. The peak at m/z 415 showed the loss of hydroxyl group
from the molecule. The characteristic fragment of flavonoid glycosides appears at m/z
286 showed the loss of 146 m.u. indicating the cleavage of the O-sugar bond. Similarly,
the peak at m/z 339 showed the loss of 93 m.u. (C
6
H
3
O), indicating the cleavage of a
phenol moiety from the molecule. The molecular ion was confirmed by the FAB
positive and FAB negative mass spectrometry.
The UV (MeOH) spectrum of compound 1 showed absorptions at
max
345, 266, 224,
215 and 210 nm, indicating the presence of kaempferol chromophore in the molecule.
The IR (CHCl
3
) showed major absorptions at 1090, 1590, 1655, 2890 and 3540 cm
1
,
indicating the presence of the C–O, C¼C, C¼O(, -unsaturated), C–H and O–H
functionalities in the molecule.
The
1
H-NMR (CDCl
3
300 MHz) spectrum showed the presence of 20 proton
resonances. The 2H singlet at 6.71 showed the presence of two symmetrical aromatic
protons, 6H and 8H at meta disposition to each other. The 2H doublet at 7.23
(J ¼ 8.0 Hz) was assigned to the 2
0
-H and 6
0
-H, indicating a pair of symmetrical protons.
Another 2H doublet at 8.03 (J ¼ 8.0 Hz) was assigned to the other pair of symmetrical
protons, 3
0
-H and 5
0
-H. The assignments of 3
0
-H/5
0
-H and 2
0
-H/6
0
-H were made on the
basis of HMBC interactions of the protons with 1
0
-C and 4
0
-C, respectively. A 1H
singlet at 6.26 was assigned to the 1
00
-H. The absence of splitting showed that the
dihedral angle between the 1
00
-H and 2
00
-H would be 90
. A singlet at 5.07 and a
doublet at 4.57 (J ¼ 7.0 Hz) were assigned to the 2
00
-H and 3
00
-H. The double doublet at
4.05 (J
1
¼ 7.0 Hz, J
2
¼ 6.5 Hz) was assigned to the 4
00
-H, while another double doublet
at 4.24 (J
1
¼ 6.5 Hz, J
2
¼ 6.1 Hz) was assigned to the 5
00
-H. A 3H doublet at 1.28
(J ¼ 6.1 Hz) was assigned to the 6
00
-H. The
1
H-NMR chemical shift assignments are
presented in table 1.
The
13
C-NMR (CHCl
3
, 75 MHz) spectrum showed the presence of 21 carbon
resonances in the molecule. The multiplicities of the carbon signals were determined by
the DEPT experiments. The signals at 94.39 and 99.70 were assigned to the 6C/8C
aromatic carbons adjacent to the hydroxyl functions while the hydroxyl bearing
carbons resonated at 165.84 (C-5) and 162.50 (C-7). The symmetrical carbons of the
phenol moiety were appeared as a 2C signal each at 131.23 (C-2
0
/C-6
0
) and 116.20
(C-3
0
/C-5
0
). The signal at 161.44 was assigned to the phenol carbon (4
0
-C) bearing OH
function. The anomeric carbon appeared at 103.61 indicating the presence of an
-glucosidic unit [13–15]. The other methine carbons of the glycosidic moiety appeared
776 Habib-ur-Rehman et al.
Downloaded By: [PERI Pakistan] At: 09:50 28 June 2010
at 73.18 (2
00
-C), 72.54 (4
00
-C), 71.80 (3
00
-C) and 69.21 (5
00
-C). The absence of a
signal around 65.00 showed the absence of –CH
2
OH function and the presence of a
methyl signal at 18.10 indicated the presence of 6
00
-methyl group. The downfield
quaternary carbon signal at 178.80 was assigned to the carbonyl carbon (4C). The
13
C-NMR chemical shifts are presented in table 2.Inlinegraphic is hidden
The signal at 8.03 assigned to the 3
0
-H/5
0
-H symmetrical protons showed COSY
interactions with the signal at 7.23 assigned to the 2
0
-H/6
0
-H, another pair of
symmetrical protons. The absence of COSY interactions of the signal at 6.71 (6H and
8H) indicated that the two aromatic protons are placed at meta disposition. The signal
at 6.26 assigned to 1
00
-H showed no detectable COSY interaction with the signal at
5.07 (2
00
-H). The latter also did not show COSY interaction with the signal at 4.57
assigned to the 3
00
-H, indicating besides the 1
00
-H and 2
00
-H, 90
dihedral angle between
the 2
00
-H and 3
00
-H. The signal at 4.57 (3
00
-H) showed COSY interactions with the
signal at 4.05 (4
00
-H) which in turn showed interactions with the signal at 4.24 (5
00
-H).
The signal at 4.24 showed strong COSY interaction with the signal at 1.28 assigned
to the 6
00
-methyl protons.
The 3H signal at 1.28 (6
00
-CH
3
) showed HMQC interaction with carbon resonance
at 18.10 (6
00
-C). The 1H signal at 4.24 showed interaction with the C-signal at 69.21.
The 1H signal at 4.57 showed interaction with the C-signal at 71.80 (3
00
-C) while the
signal at 4.05 (4
00
-H) showed interaction with the C-signal at 72.54 (4
00
-C). The
H-signal at 4.57 (3
00
-H) showed HMQC interaction with the C-signal at 71.80 (3
00
-C).
The 1H signal at 5.07 (2
00
-H) showed interaction with the C-signal at 73.18 (2
00
-C).
The 2H signal at 8.03 (3
0
-H/5
0
-H) showed interaction with the C-signal at 116.20
(3-C/5
0
-C) while the 2H signal at 7.23 (2
0
-H/6
0
-H) showed interaction with C-signals at
131.45 (2
0
-C/6
0
-C). The signal at 6.71 assigned to the 6H and 8H showed HMQC
interactions with the C-signals at 99.70 and 94.39, assigned to the 6C and 8C,
respectively. The H-signal at 6.26 (1
0
-H) showed HMQC interactions with the C-signal
at 103.61 (1
00
-C).
The 3H signal 1.28 (6
00
-CH
3
) showed HMBC interactions with the C-signals at
69.21 (5
00
-C) and 72.54 (4
00
-C). The H-signal at 4.24 (6
00
-H) showed interactions
with the C-signals at 18.10 (6
00
-C) and 71.80 (3
00
-C) while the H-signal at 5.07
(2
00
-H) showed interactions with the C-signal at 72.54 (4
00
-C). The H-signal at 8.03
Table 1.
1
H-NMR chemical shift assignments of compounds 1 and 2.
Proton no. 12
6H 6.71 (1H, s) 6.60 (1H, s)
8H 6.71 (1H, s) 6.60 (1H, s)
2
0
-H 7.23 (1H, d, J ¼ 8.0 Hz) 7.13 (1H, d, J ¼ 8.0 Hz)
3
0
-H 8.03 (1H, d, J ¼ 8.0 Hz) 8.15 (1H, d, J ¼ 8.0 Hz)
5
0
-H 8.03 (1H, d, J ¼ 8.0 Hz) 8.15 (1H, d, J ¼ 8.0 Hz)
6
0
-H 7.23 (1H, d, J ¼ 8.0 Hz) 7.13 (1H, d, J ¼ 8.0 Hz)
O-Hs 5.31 (6H, bs) 5.30 (6H, bs)
1
00
-H 6.26 (1H, s) 6.29 (1H, m)
2
00
-H 5.07 (1H, s) 4.73 (1H, m)
3
00
-H 4.57 (1H, d, J ¼ 7.0 Hz) 4.31 (1H, d, J ¼ 7.0 Hz)
4
00
-H 4.05 (1H, dd, J
1
¼ 7.0 Hz, J
2
¼ 6.5 Hz) 4.12 (1H, dd
0
J
1
¼ 7.0 Hz, J
2
¼ 6.7 Hz)
5
00
-H 4.24 (1H, dd, J
1
¼ 6.5 Hz, J
2
¼ 6.1 Hz) 4.20 (1H, dd, J
1
¼ 6.7 Hz, J
2
¼ 6.5 Hz)
6
00
-H 1.28 (3H, d, J ¼ 6.1 Hz) 1.41 (2H, m)
7
00
-H 0.88 (3H, m)
Phytochemical investigations of P. emblica 777
Downloaded By: [PERI Pakistan] At: 09:50 28 June 2010
(3
0
-H/5
0
-H) showed HMBC interactions with the C-signals at 131.23, 131.45 and
161.44. The H-signal at 7.23 (2
0
-H/6
0
-H) showed interactions with the C-signals at
116.20 (3
0
-C and 5
0
-C), 121.80 (1
0
-C) and 131.23 (2C) while the H-signal at 6.71
(6H and 8H) showed HMBC interactions with the C-signals at 157.57, 157.65,
162.50 and 165.84. The H-signal at 6.26 showed HMBC interactions with the
C-signals at 73.18 (2
00
-C). Similar
1
H–
13
C interactions were also observed for other
glycosidic protons. Based on the above spectroscopic data, structure 1 was assigned to
the compound, kaempferol-3-O--
L-(6
00
-ethyl)-rhamnopyranoside.
Kaempferol-3-O-a-
L-(5
00
-ethyl)-rhamnopyranoside (2): The mass spectrum of compound
2 showed the molecular ions peak at m/z 446.1235, corresponding to the molecular
formula C
22
H
22
O
10
, indicating 12
of unsaturation in the molecule. The other major
fragmented ion peaks were found to be at m/z 445, 431, 429, 352, 286, 269, 255, 227,
210, 183, and 163. The peak at m/z 431 showed the loss of methyl group from the
molecule. A fragment characteristic to flavonoid glycosides appear at m/z 286. The peak
at m/z 269 showed the loss of 177 m.u., indicating the cleavage of the O-sugar bond.
Similarly, the peak at m/z 353 showed the loss of 93 m.u. (C
6
H
5
O), indicating the
cleavage of phenol moiety from the molecule. The molecular ion was confirmed by the
FAB positive mass spectrometry.
The UV (MeOH) spectrum of the compound 1 showed max at 210, 230, 285 nm,
indicating the presence of kaempferol chromophore in the molecule. The IR (CHCl
3
)
showed major absorptions at 1090, 1590, 1655, 2890 and 3540 cm
1
indicating the
presence of the C–O, C¼C, C¼O(, -unsaturated), C–H and O–H functionalities in
the molecule.
Table 2.
13
C-NMR chemical shift assignments of compounds 1 and 2.
Carbon no. 12
2C 131.23 (C) 131.40 (C)
3C 121.70 (C) 121.93 (C)
4C 178.75 (C) 178.70 (C)
4a-C 157.65 (C) 157.60 (C)
5C 165.84 (C) 165.80 (C)
6C 94.39 (CH) 99.50 (CH)
7C 162.50 (C) 162.55 (C)
8C 99.70 (CH 94.20 (CH)
8a-C 157.57 (C) 157.30 (C)
1
0
-C 121.80 (C) 122.10 (C)
2
0
-C 131.23 (CH) 131.69 (CH)
3
0
-C 116.20 (CH) 116.28 (CH)
4
0
-C 161.44 (C) 161.30 (C)
5
0
-C 116.20 (CH) 116.28 (CH)
6
0
-C 131.23 (CH) 131.69 (CH)
1
00
-C 103.61 (CH) 103.60 (CH)
2
00
-C 73.18 (CH) 73.38 (CH)
3
00
-C 71.80 (CH) 71.60 (CH)
4
00
-C 72.54 (CH) 72.00 (CH)
5
00
-C 69.21 (CH) 69.20 (CH)
6
00
-C 18.10 (CH
3
) 29.76 (CH
2
)
7
00
-C 9.18 (CH
3
)
778 Habib-ur-Rehman et al.
Downloaded By: [PERI Pakistan] At: 09:50 28 June 2010
The
1
H-NMR (CDCl
3
, 300 MHz) spectrum showed the presence of 22 proton
resonances in the molecule. The 2H singlet at 6.60 showed the presence of two
symmetrical aromatic protons (6H/8H) at meta disposition to each other. The doublets
at 7.13 (J ¼ 8.0 Hz) and 8.15 (J ¼ 8.0 Hz) of 2H each indicating the two pairs of
symmetrical protons, 2
0
-H/6
0
-H and 3
0
-H/5
0
-H, respectively. The signal at 6.29 was
assigned to the 1
00
-H. The multiplet at 4.73 and a doublet at 4.31 (J ¼ 7.0 Hz) were
assigned to the 2
00
-H and 3
00
-H, respectively. The double doublet at 4.12 (J
1
¼ 7.0 Hz,
J
2
¼ 6.7 Hz) was assigned to the 4
00
-H while another double doublet at 4.20
(J
1
¼ 6.7 Hz, J
2
¼ 6.5 Hz) was assigned to the 5
00
-H. A 2H multiplet at 1.41 was
assigned to the 6
00
-CH
2
protons. A 3H multiplet at 0.88 was assigned to the methyl
protons. The
1
H-NMR assignments and coupling interactions were confirmed by the
2D-COSY and also by the HMQC and HMBC experiments. The
1
H-NMR chemical
shift assignments are presented in table 1.
The
13
C-NMR (CHCl
3
, 75 MHz) spectrum showed the presence of 22 carbon
resonances in the molecule. The multiplicities of the carbon signals were determined by
the DEPT experiments. The peaks at 99.50 and 94.20 were assigned to the aromatic
carbons 6C and 8C, adjacent to the hydroxyl functions, respectively while the OH
bearing carbons, (5C and 7C) resonated at 165.80 and 162.55, respectively. The
symmetrical carbons of the phenol moiety (2
0
-C/6
0
-C and 3
0
-C/5
0
-C) were appeared as a
2C signal each at 131.69 and 116.28. The signal at 161.30 was assigned to the
phenol carbon (4
0
-C) bearing OH function. The anomeric carbon (1
00
-C) appeared at
103.60, indicating the presence of -glucosidic unit [13–15]. The other methine carbon
signals appeared at 73.38, 71.60, 72.00 and 69.20, were assigned to the 2
00
-C, 3
00
-C,
4
00
-C and 5
00
-C. The absence of the signal around 65.00 showed the absence of CH
2
OH
function and the presence of methylene and methyl signals at 29.76 and 9.18,
respectively, indicated the presence of –CH
2
CH
3
at 5
00
-C. The downfield quaternary
carbon signal at 178.70 was assigned to the carbonyl carbon (4C). The
13
C-NMR
chemical shifts are presented in table 2. Based on the above spectral data, structure 2
was assigned to the compound, kaempferol-3-O--
L-(6
00
-ethyl)-rhamnopyranoside.
3. Experimental
3.1. Instrumental
UV spectra were recorded on a Shimadzu 1601 Japan made double beam spectro-
photometer, IR spectra were recorded on FTIR Shimadzu Japan made, mass spectra
were recorded on Varian MAT 312 mass spectrometer connected to DDP 11/34 DEC
computer system. The
1
H-NMR spectra were recorded at 300 MHz on Bruker AM 300
NMR Spectrometer while the
13
C-NMR spectra were recorded at 75 MHz on the same
instrument. The optical rotation was recorded on polartromic universal Australian
Standard K-157 digital Polarimeter. TLC experiment were performed on silica gel
(GF-254, 0.2 mm) E.Merk.
3.2. Plant material
The shoots and leaves (5 kg) of P. emblica Linn. (Euphorbeaceae) were collected in June
2002 from the Village Jatlan, District Mirpur, Azad Kashmir, Pakistan. The plant was
Phytochemical investigations of P. emblica 779
Downloaded By: [PERI Pakistan] At: 09:50 28 June 2010
identified by a taxonomist at the Department of Botany, University of Azad Jammu
and Kashmir, Muzaffarabad where a voucher specimen is deposited in the herbarium of
the department.
3.3. Isolation of (1) and (2)
The shoots and leaves of P. emblica were dried and cut into small pieces. The dried plant
material was crushed to powder. The powdered material (1.3 kg) was extracted with
methanol (4.2 L) and filtered. The filtrate was evaporated on a rotary evaporator under
reduced pressure to dryness, which resulted to a blackish green material.
The methanol extract was subjected to the silica-gel column chromatography and
eluted with a mixture of chloroform and methanol (7.0 : 3.0). This resulted seven frac-
tions of 15 mL each. The fraction 3 was subjected to the PTLC experiments to identify
the isolation pattern. The system of CHCl
3
/CH
3
OH (5.0:5.0) indicated two bands
having distinct Rf values. Therefore, the fraction was subjected to the PTLC with
CHCl
3
/CH
3
OH (5.0 : 5.0) as the solvent system. This afforded semi-pure compounds
1 and 2 which were further purified by rechromatography on PTLC with
CHCl
3
/CH
3
OH (5.5 : 4.5) as the solvent system. This resulted in the isolation of the
pure compounds 1 (Rf ¼ 0.7; 23 mg; m.p. 78
C; 1.77 10
3
% yield; []
D
45
) and
2 (Rf ¼ 0.6; 15 mg; m.p. 83
C; 1.16 10
3
% yield; []
D
70
).
References
[1] A.V.S. Sambamurty, N.S. Subrahmaniyam. Economic Botany, p. 738, Wiley Estern Ltd., New Dehli
(1989).
[2] S. Krishnamurty. Proc. Ind. Aca. Sci., 24A, 357 (1946).
[3] A. Kalam, S.M. Sacay. J. Sci. Ind. Res., 6B, 42 (1947).
[4] N.V.R. Kumar, K.L. Joy, G. Kuttan, R.S. Ramsewak, M.G. Nair, R. Kuttan. J. Ethnopharmacology, 81,
17 (2002).
[5] G.D. Bagchi, G.N. Srivastara, S.C. Singh. Indian J. Pharmacognosy, 30, 161 (1992).
[6] N. Fox. Phillipino. J. Sci., 81, 217 (1952).
[7] N. Chopra. J. Bombay Nat. Hist. Soc., 42, 888 (1941).
[8] K.R. Shanmugasundaram, P.G. Seethapathy, E.R. Shanmugasundaram. J. Ethnopharmacol, 7, 247
(1983).
[9] P. Scartezzini, E. Speroni. J. Ethnopharmacology, 71, 23 (2000).
[10] Y.J. Zhang, T. Tanaka, Y. Iwamoto, C.R. Yang, I. Kouno. J. Nat. Prod., 63, 1507 (2000).
[11] Y.J. Zhang, T. Tanaka, Y. Iwamoto, C.R. Yang, I. Kouno. Tetrahedron Lett., 41, 1781 (2000).
[12] N. Vongvanich, P. Kittakoop, J. Kramyu, M. Tanticharoen, Y. Thebaranonth. J. Org. Chem., 65, 5420
(2000).
[13] W.B. Mors, M. Celia-do-Nascimento, M. Ruppelt, B. Pereira, N.A. Pereira. Phytochemistry, 55, 627
(2000).
[14] Y.J. Zhang, T. Tanaka, C.R. Yang, I. Kouno. Chem. Pharm. Bull., 49, 537 (2001).
[15] K. Yawaski, H. Kohda, R. Tkobeyashi, O. Tanaka. Tetrahedron Lett., 1005 (1976).
[16] M.R. Vigon, J.A. Vottero. Tetrahedron Lett., 2445 (1976).
[17] P.J. Houghton, I.M. Osibogun. J. Ethnopharmacology, 39, 1 (1993).
780 Habib-ur-Rehman et al.
Downloaded By: [PERI Pakistan] At: 09:50 28 June 2010
Phytochemical investigations of P. emblica 781
Downloaded By: [PERI Pakistan] At: 09:50 28 June 2010
... Flavonols are widely distributed in the different sections of the amla plant. Kampferol their derivatives (dihydrokaempferol, kaempferol 3-b-dglucopyranoside, kaempferol 3-o-rhamnoside, kaempferol-3-o-α-l-(6"-ethyl)rhamnopyranoside, and kaempferol-3-o-α-l-(6"-methyl)-rhamnopyranoside) are found in fruits, leaves branches and shoots [19,[21][22][23]. In a similar way, quercetin and its derivatives (quercetin 3-b-D -glucopyranoside, quercetin 3-O-glucoside, quercetin 3-O-rhamnoside, and rutin) are distributed in fruits, leaves and branches [16][17][18][19]21,23]. ...
Article
Full-text available
Phyllanthus emblica L. (also popularly known as amla) is a tree native to the India and Southeast Asia regions that produces fruits rich in bioactive compounds that could be explored as part of the increasing interest in naturally occurring compounds with biological activity. Thus, this review aims to highlight the nutritional aspects, rich phytochemistry and health-promoting effects of amla. Scientific evidence indicates that polyphenols are central components in fruits and other sections of the amla tree, as well as vitamin C. The rich composition of polyphenol and vitamin C imparts an important antioxidant activity along with important in vivo effects that include improved antioxidant status and activity of the endogenous antioxidant defense system. Other potential health benefits are the anti-hyperlipidemia and antidiabetic activities as well as the anticancer, anti-inflammatory, digestive tract and neurological protective activities. The promising results provided by the studies about amla bioactive compounds support their potential role in assisting the promotion of health and prevention of diseases.
... The flavonoid compounds contained in PE are kaempferol-3-O α-L-(6"-methyl)-rhamnopyranoside, kaempferol-3-O-α-L-(6"-ethyl) rhamnopyranoside, and other compounds, such as Triacontanol, Triacontanoic acid, β-Amyrin ketone, Betulonic acid, Daucosterol, Lupeol acetate, β-Amyrin-3-palmitate, Gallic acid, Betulinic acid, Ursolic acid, Oleanolic acid, Quercetin, Rutin, and Bisabolane. Also, PE fruit is rich in vitamin C, luteolin, and corilagin (Habib et al. 2007;Poltanov et al. 2009;Luo et al. 2011;Pientaweeracth et al. 2016). ...
Article
Full-text available
Phyllanthus emblica (PE) is a plant widely found in Indonesia, especially in Sumatra island, and in India. This study followed the OECD No. 420. The groups were divided based on gender, male and female rats. Male rats were divided into 6 groups, which were male/female control, male/female 2000 mg/kgBW, and male/female 5000 mg/kgBW. This study revealed that the ethanol extract of Phyllanthus emblica (EEPE) doses of 2000 mg/kgBW and 5000 mg/kgBW did not cause histological changes in the heart, liver, testes, ovaries, and kidneys, and did not cause changes to the hematological parameters, kidney biochemical parameters, liver biochemical parameters, and electrolyte parameters both in male and female rats. The results show that the LD50 of EEPE is higher than 5000 mg/kgBW. In short, this study provides information regarding the antioxidant activity and the safe use of EEPE. The LD 50 of extract ethanol of Phyllanthus emblica is higher than 5000 mg/kgBW.
... Moreover, it demonstrates cardiotonic properties by lowering serum cholesterol levels, reducing myocardial necrosis, enhancing blood circulation, and strengthening capillaries. Flavonoids, tannins, gallic acid, pectin, vitamin C, corilagin, and phyllaemblic compounds are present in in P. emblica fruits (Habib-ur-Rehman et al., 2007). Terminalia bellirica extract contains b-sitosterol, tannins and phenolic acids such as ellagic acid, gallic acid, galloyl glucose, ethyl gallate, and chebulaginic acid (Kumar and Khurana, 2018). ...
Article
Full-text available
Severe acute respiratory syndrome coronavirus disease (SARS-CoV-2) induced coronavirus disease 2019 (COVID-19) pandemic is the present worldwide health emergency. The global scientific community faces a significant challenge in developing targeted therapies to combat the SARS-CoV-2 infection. Computational approaches have been critical for identifying potential SARS-CoV-2 inhibitors in the face of limited resources and in this time of crisis. Main protease (M pro) is an intriguing drug target because it processes the polyproteins required for SARS-CoV-2 replication. The application of Ayurvedic knowledge from traditional Indian systems of medicine may be a promising strategy to develop potential inhibitor for different target proteins of SARS-CoV-2. With this endeavor, we docked bioactive molecules from Triphala, an Ayurvedic formulation, against M pro followed by molecular dynamics (MD) simulation (100 ns) to investigate their inhibitory potential against SARS-CoV-2. The top four best docked molecules (terflavin A, chebulagic acid, chebulinic acid, and corilagin) were selected for MD simulation study and the results obtained were compared to native ligand X77. From docking and MD simulation studies, the selected molecules showed promising binding affinity with the formation of stable complexes at the active binding pocket of M pro and exhibited negative binding energy during MM-PBSA calculations, indication their strong binding affinity with the target protein. The identified bioactive molecules were further analyzed for drug-likeness by Lipinski's filter, ADMET and toxicity studies. Computational (in silico) investigations identified terflavin A, chebulagic acid, chebulinic acid, and corilagin from Triphala formulation as promising inhibitors of SARS-CoV-2 M pro , suggesting experimental (in vitro/in vivo) studies to further explore their inhibitory mechanisms .
... Moreover, it demonstrates cardiotonic properties by lowering serum cholesterol levels, reducing myocardial necrosis, enhancing blood circulation, and strengthening capillaries. Flavonoids, tannins, gallic acid, pectin, vitamin C, corilagin, and phyllaemblic compounds are present in in P. emblica fruits (Habib-ur-Rehman et al., 2007). Terminalia bellirica extract contains β-sitosterol, tannins and phenolic acids such as ellagic acid, gallic acid, galloyl glucose, ethyl gallate, and chebulaginic acid (Kumar and Khurana, 2018). ...
Article
Full-text available
Severe acute respiratory syndrome coronavirus disease (SARS-CoV-2) induced coronavirus disease 2019 (COVID-19) pandemic is the present worldwide health emergency. The global scientific community faces a significant challenge in developing targeted therapies to combat the SARS-CoV-2 infection. Computational approaches have been critical for identifying potential SARS-CoV-2 inhibitors in the face of limited resources and in this time of crisis. Main protease (Mpro) is an intriguing drug target because it processes the polyproteins required for SARS-CoV-2 replication. The application of Ayurvedic knowledge from traditional Indian systems of medicine may be a promising strategy to develop potential inhibitor for different target proteins of SARS-CoV-2. With this endeavor, we docked bioactive molecules from Triphala, an Ayurvedic formulation, against Mpro followed by molecular dynamics (MD) simulation (100 ns) to investigate their inhibitory potential against SARS-CoV-2. The top four best docked molecules (terflavin A, chebulagic acid, chebulinic acid, and corilagin) were selected for MD simulation study and the results obtained were compared to native ligand X77. From docking and MD simulation studies, the selected molecules showed promising binding affinity with the formation of stable complexes at the active binding pocket of Mpro and exhibited negative binding energy during MM-PBSA calculations, indication their strong binding affinity with the target protein. The identified bioactive molecules were further analyzed for drug-likeness by Lipinski’s filter, ADMET and toxicity studies. Computational (in silico) investigations identified terflavin A, chebulagic acid, chebulinic acid, and corilagin from Triphala formulation as promising inhibitors of SARS-CoV-2 Mpro, suggesting experimental (in vitro/ in vivo) studies to further explore their inhibitory mechanisms.
... D-glucose, D-fructose, D-myositol, D-galacturonic acid, D-arabinose, D-rhamnosyl, D-xylosyI, D-glucosyI, D-mannosyl, and D-galactosyI residue are sugars. The major tannins identified in the plant are emblicanin A, emblicanin B, pedunculagin, and punicgluconin [102]. ...
Article
Full-text available
Viruses are responsible for a variety of human pathogenesis. Owing to the enhancement of the world population, global travel, and rapid urbanization, and infectious outbreaks, a critical threat has been generated to public health, as preventive vaccines and antiviral therapy are not available. Herbal medicines and refined natural products have resources for the development of novel antiviral drugs. These natural agents have shed light on preventive vaccine development and antiviral therapies. This review intends to discuss the antiviral activities of plant extracts and some isolated plant natural products based on mainly preclinical (in vitro and in vivo) studies. Twenty medicinal herbs were selected for the discussion, and those are commonly recognized antiviral medicinal plants in Ayurveda (Zingiber officinale, Caesalpinia bonducella, Allium sativum, Glycyrrhiza glabra, Ferula assafoetida, Gymnema sylvestre, Gossypium herbaceum, Phyllanthus niruri, Trachyspermum ammi, Withania somnifera, Andrographis paniculata, Centella asiatica, Curcuma longa, Woodfordia fruticose, Phyllanthus emblica, Terminalia chebula, Tamarindus indica, Terminalia arjuna, Azadirachta indica, and Ficus religiosa). However, many viruses remain without successful immunization and only a few antiviral drugs have been approved for clinical use. Hence, the development of novel antiviral drugs is much significant and natural products are excellent sources for such drug developments. In this review, we summarize the antiviral actions of selected plant extracts and some isolated natural products of the medicinal herbs.
... Different parts of the plant have been used to defend against diseases (Variya et al., 2016). Particularly, its fruit contains the highest source of vitamin C and also various bioactive substances including tannin, gallic acid, quercetin, ellagic acid, corilagin, apigenin and luteolin (Habib-ur-Rehman et al., 2007). Furthermore, previous studies have shown the anti-hyperglycemic, anti-diabetic, anti-hyperlipidemic, anti-inflammatory, anti-oxidant, anti-cancer and immune-enhancer properties in Indian gooseberry fruits (Variya et al., 2016;Yadav et al., 2017;Srinivasan et al., 2018;Variya et al., 2018). ...
Article
Full-text available
Indian gooseberry (Phyllanthus emblica L.) is widely used in Ayurvedic medicine, traditional Chinese medicine, as well as traditional medicine to treat health complications including disorders of diabetes and obesity. The aim of this study was to investigate the effects of Indian gooseberry fruit on anxiety-related behaviors and memory performance in high-fat diet-induced obese mice. C57BL/6 mice were randomly divided into four groups (n = 11 pre group); group 1: normal diet control, 2: normal diet treated with Indian gooseberry fruit juice, 3: high-fat diet control, and 4: high-fat diet treated with Indian gooseberry fruit juice. Each mouse was orally and daily administrated with 5mL/kg of Indian gooseberry fruit juice. After six weeks, all groups were tested for blood glucose levels, anxiety and memory performances, and the level of interleukin 6 (IL-6) in the hippocampus. The results revealed that the treatment with Indian gooseberry juice for six weeks produced a significant decrease in blood glucose levels (P <0.05). In anxiety-related behaviors, Indian gooseberry juice showed a remarkable decrease in self-grooming behavior (P <0.001). In addition, there was a significant increase in memory performance in the high-fat diet treated with Indian gooseberry fruit juice compared to the high-fat diet control (P <0.05). Furthermore, the level of inflammatory cytokine IL-6 in the hippocampus was significantly decreased after oral administration of Indian gooseberry fruit juice (P <0.05). These findings suggest that Indian gooseberry fruit can serve as a natural nutritional treatment for preventing high-fat diet-induced cognitive impairment. Keywords: Anxiety-related behaviors, High-fat diet, Indian gooseberry, Memory performance, Obesity
Preprint
Full-text available
The years 2019-2021 witnessed a pandemic that forced humans to confine to their homes. COVID has already taken millions of lives worldwide and there is a need to review the existing medical intervention. When there is an outbreak of a disease, our body's defense mechanism works as a shield to prevent the body from invading pathogens. This ability of humans has evolved over a long period. Though the COVID-19 pandemic is threatening the world, even in the absence of any targeted medicine or vaccine, 433 million people recovered, which speaks volumes about the immune system's capability to counter hitherto unknown invaders. The proposed plasma therapy is also dependent on the antibodies produced by the immune system of a recovered patient. Vaccines created against SARS-CoV2 also trigger the natural immune system to make the necessary antibodies before the active virus attacks. Thus, all available and future roads point towards the capability of our immune system only. The COVID waves made scientists and researchers understand that not every person exposed to the SARS CoV-2 virus gets infected, and not all COVID-positive patients develop respiratory issues [1]. The conventional medicinal system has also contributed in a great way to curb the situation. However, an accepted and recommended approach to complementary therapies as a holistic tool has not found its way. Antibiotics target pathogens mostly with no consideration of repercussions on host cells [2]. In this paper, we have tried to address the current situation and the role of yoga, meditation, and breathing techniques to help face the crisis and prepare our immune system for possible further outbreaks. We also look at diet and other factors that impair our immunity and make us more vulnerable to virus attacks.
Article
Medicinal plant are mostly used in healthcare in the whole world. The medicinal plant. are Effective in production of medicine . In this paper we can seen the role and usefullness of medicinal plants and approaches to diseases prevention.
Article
Full-text available
Purpose In this paper, a probabilistic neural network (PNN)-based simple model for the detection of freshness in Indian gooseberry or amla (Phyllanthus emblica) samples has been developed. Methods The amla images have been analyzed using two features: hue histogram, which is a kind of color representative of the image, and entropy analysis, which corresponds to texture analysis of the sample images. Three freshness classes have been assigned depending on the freshness of the samples and governed by the Hedonic scale. Results The proposed PNN model is also tested with five different activation functions; out of which, radial and triangular basis functions are found to yield the most accurate results. Moreover, the hue-PNN model is found to possess marginal superiority over the entropy-PNN model, thus signifying the higher effectiveness of the former in the proposed work. The proposed work is computationally lighter as it contains PNN as the single analysis tool, aided by the image histograms. Moreover, the experiments have been conducted with the images captured using smartphones only, which establishes the portability of capturing images. Conclusions High freshness classification accuracy of 97.5%, ease of implementation, and use of smartphone captured images widen its practical applicability of developing into a smartphone application-based module.
Article
Full-text available
A lot of medicinal plants, traditionally used for thousands of years, are present in a group of herbal preparations of the Indian traditional health care system (Ayurveda) named Rasayana proposed for their interesting antioxidant activities. Among the medicinal plants used in ayurvedic Rasayana for their therapeutic action, some of these have been throughly investigated. In the present paper seven plants (Emblica officinalis L., Curcuma longa L., Mangifera indica L., Momordica charantia L., Santalum album L., Swertia chirata Buch-Ham, Withania somnifera (L.) Dunal) are viewed for their historical, etymological, morphological, phytochemical and pharmacological aspects. The plants described contain antioxidant principles, that can explain and justify their use in traditional medicine in the past as well as the present. In order to identify the plants with antioxidant activity in Ayurveda, a formulation of some rasayanas with well defined antioxidant properties has been examinated. For this purpose, we have considered Sharma's work on the preparation MAK4, MAK5, MA631, MA 471, MA Raja's Cup, MA Student Rasayana, MA Ladies Rasayana.
Article
Full-text available
The article surveys the substances identified in plants reputed to neutralize the effects of snake venoms. Protective activity of many of them against the lethal action of the venom of the jararaca (Bothrops jararaca) snake was confirmed by biological assays. It was shown that all belong to chemical classes capable of interacting with macromolecular targets--receptors and enzymes. In a few cases it has been shown that exogenous natural micromolecules can mimic the biological activity of endogenous macromolecules. From the evidence presented, it can be inferred that micromolecules which neutralize the action of snake venoms mechanistically replace endogenous antitoxic serum proteins with venom neutralizing capacity such as produced by some animals.
Article
Phyllaemblic acid, a novel highly oxygenated norbisabolane was isolated from the roots of Phyllanthus emblica, and its structure was fully characterized by spectroscopic and chemical means. The absolute stereochemistry was determined by applying modified Mosher’s method to an opportune degradation product.
Article
Phyllanthin, the bitter principle of the leaves ofPhyllanthus niruri has been isolated in a crystalline condition and in good yield. It melts at 97–98°, has the molecular formula C21H22O7 and contains methoxyl and methylene-dioxy groups. Its important properties are described. A related crystalline substance, hypophyllanthin, which is not bitter, has also been isolated in a small yield. The leaves contain about 5% of wax which consists mostly of esters.
Article
Six new phenolic constituents, L-malic acid 2-O- (1), mucic acid 2-O- (5), mucic acid 1, 4-lactone 2-O- (6), 5-O- (8), 3-O- (10), and 3, 5-di-O- (11) gallates, were isolated from the fruit juice of Phyllanthus emblica together with their methyl esters (2-4, 7, 9), and their structures were determined by spectral and chemical methods. Compounds 5, 6, and 8, the major phenolic constituents of the juice, were present as an equilibrium mixture in aqueous solution
Article
The procedure for the preparation of Anna Pavala Sindhooram (APS), a drug based on the concepts of Indian medicine for the prevention and reversal of the atherosclerotic disease process is described in detail. The uniformity in the composition of samples of the drug obtained in 10 batches, prepared over a period of 5 years is evident from the chemical analysis of the mineral constituents. The possibility of iodine, copper, iron, calcium and magnesium present in the Anna Pavala Sindhooram, acting metabolically to reduce hypercholesterolemia is discussed. The ingredients used are green vitriol (Annabedi or ferrous sulphate), coral reef (Corallium rubrum or Pavalam), leaves of Acalypha indica (Kuppaimeni), Lippia nodiflora (Poduthalai), Vinca rosea (Nityakalyani), Lawsonia alba (maruthondri) and Cynodon dactylon (Arugampul) and the flowers of Hibiscus rosasinensis (Chemparathampoo) and the ripe fruits of Phyllanthus emblica (nellikkai). Sindhooram is the chief therapeutic form of herbo-mineral preparations used in the Sidha system of Indian medicine.
Article
A list of flowering plants used for the treatment of snakebite has been complied from a variety of literature sources. Details of the geographical area and parts used are given and the basis for the reputed activity discussed. Methods of testing the reputed activity of such plants are reviewed and the identity and mode of action of the chemical substances which might be responsible is discussed for some of the plants listed.
Article
Three ester glycosides, named phyllaemblicins A (3), B (4), and C (5), and a methyl ester (2), of a highly oxygenated norbisabolane, phyllaemblic acid (1), were isolated from the roots of Phyllanthus emblica, along with 15 tannins and related compounds. The structures of 2-5 were established by spectral and chemical methods.