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CHEMICAL CONSTITUENTS OF Terminalia Chebula
Dedicated to Professor Umesh R. Desai (Virginia Commonwealth University, Virginia, USA)
Muhammad Riaz1* and Obaid-ur-Rehman Khan1¸ Muhammad Qayyum Khan2 and Rehana Rashid3
1
Department of Chemistry, University of Azad Jammu and Kashmir, Muzaffarabad, 13100, Pakistan
2 Department of Botany, University of Azad Jammu and Kashmir, Muzaffarabad, 13100, Pakistan
3 Department of Chemistry, COMSATS Institute of Information Technology, University Road, 22060, Abbottabad, Pakistan
Corresponding Author:
Dr. Muhammad Riaz, Associate Professor, Department of Chemistry, University of Azad Jammu and Kashmir, Muzaffarabad, 13100,
Pakistan Tel: (92)334 9270235, Email: [email protected]
ABSTRACT:: Despite the revolutionary progress and discoveries, the challenge to combat newly emerged and discovered
diseases remains unmet. Natural products are still the prime reservoirs for providing new and novel molecular skeletons as
drug candidates and inspiration. Terminalia chebula showed promising anti-microbial and anti-viral potentials and about133
natural products have already been isolated from T. chebula and importantly, its richness of variety of metabolic enzymes are
biosynthesizing diverse variety of secondary metabolites with attractive novelty and variety, ranging from phenolic derivative
to flavonoids and falvins, terpenoids to steroids, alkaloids, tannins and their derivatives and glycosides. Molecular topology
and variety in functionalities of in its natural products are important, especially dealing with the variable and adaptive
capabilities of viruses and microorganism generated diseases. Importantly, it is useful for natural product chemist to have the
updated chemical constituents of T. chebula.
Key words: Terminalia Chebula, chemical constituents, nature unique diverse and rich variety
INTRODUCTION:
Despite of the investments and progress in molecular biology
and drug discovery, several infections by pathogenic
microbes are major threats for human life. Development of
various anti-microbial drugs have meaningfully controlled
several pathogenic diseases or made them less destructive.
However, emerging resistance against existing antibiotics has
made them less effective and is a major threat to the
humanity. Therefore the new antibiotics are crucially required
on War-footing for the discovery and development of new
antibiotics. Prevention of infections, tracking the resistant
strains and proper use of antibiotics would be important
precautionary measures [1,2]. Natural products played the
fundamental role as traditional herbal medicine and remedies
and through advancement in the knowledge and research
gave birth to the specific molecular medicines which also
enhanced the structural and mechanistic understandings of
biochemical entities and processes [3,4]. A major number of
drugs have been derived or inspired from natural products
[5]. Pain relieving properties of the Willow’s bark lead to the
discovery of acetylsalicylic acid (aspirin)[6]. The first
antibiotic, penicillin, was isolated from a mold, penicillium
and terpenoidal anti-cancer taxol was isolated from Taxus
brefolia [7]. Structural and functional biology, and medicinal
chemistry have rewarded with revolutionary drugs, however,
pathogenic micro-organism are major global risk to human
health [8]. A progressive microbial resistance is
an alarming threat causing community-acquired infections
and antibiotic failure [9]. Plants have 9 been and are still the
major, rich and diverse source of variety of phytochemicals
including potent anti-microbial molecules. 34 Interestingly
and presumably, since plant extracts contain many
phytochemicals therefore, using plant extracts may pose some
difficulty against the development of bacterial resistance as
compared to the single molecular drug. 35 Plants have
provided anti-AIDS agents as well as anti-cancer taxol and
homoharringtonine, benzylisoquinoline, papaverine with high
inhibition to the replication of many viruses (e.g.
cytomegalovirus, measles and HIV), atropisomeric
naphthylisoquinoline dimers, michellamines A, B, and C
showed potential HIV-1 and HIV-2 on human
lymphoblastoid target cell in vitro. Low cost to benefit ratio
of natural product derived drugs is another attraction. 4
1. Terminalia chebula
Terminalia chebula is a large sized traditional medicinal plant
that is found in Pakistan, India, China and Tibet. It belongs to
genus Terminalia which contains 250 species widely
distributed throughout the tropical areas of the world [10]
Traditionally, it is being used to treat gastrointestinal and
urinary tract diseases, fever, cough, diarrhea, wound
infections, skin diseases, urinary tract infection and
candidiasis [11]. T. chebula possesses effective anti-bacterial
and anti-viral activity against various bacterial strains.[12].
September-October
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4.
Rich, Diverse and Novel Nature Molecular
Engineering (Chemical Constituents) in Terminalia
chebula:
Terminalia chebula habitats in tropical and sub-tropical
diverse climatic condition and also is rich with metabolic
engineering enzymes, therefore it is extremely rich and
diverse precursor for variety of natural products belonging to
the various classes with different levels of biosynthesis.
Richness, diversity and novelty of tannins and their analogues
in T. chebula is a complex challenge both in term of isolation
and structural modification but is an opportunity for the
organic and medicinal chemists to modulate various
biological disorders, especially pathogenic diseases because
of their structural properties. Opportunity by T. chebula, is
not limited to the tannins but also is fascinating with the
provision of its small bioactive molecules which are very
Sci.Int.(Lahore),28(5),4511-4521,2016
attractive for medicinal chemists and R&D organizations.
Additionally, the variety of different classes of bioactive
natural products in T. chebula further attracts the focused
researchers which include, flavonoids, flavins, terpenoids,
steroids, various phenols, functionalized aliphatic molecules
and their glycosides.13 Structural diversity and novelty of the
nature’s molecular engineering in T. chebula, especially in
terms of in their skeletons, functionalities and linkages, is
fascinating and invite focused and applied research to exploit
their benefits in the form of new drugs (especially,
antibiotics) further studies. Also, we understand and strongly
propose that the standardization, efficacy, safety studies and
documentations of its herbal products as of urgent prime
importance. Focused and guided phytochemical reinvestigation would be important and rewarding.
Table-1: Chemical Constituents of Terminalia chebula
Tannins
Ref.
#
1
2
3
Punicalagin((2,3-(S)-hexahydroxydiphenoyl-4,6-(S,S)-gallagyl-D-glucose)
terflavin A
Terchebulin
14
4
5
6
7
8
9
Terchebin (1, 3, 6-trigalloyl glucose,)
Terflavins B
Terflavin C
Terflavin D
Punicalin
Neo-chebulic acid
13
10
11
12
X+
1,6-di-O-galloyl-D-glucose
Gallic acid (3,4,5-Trihydroxybenzoic acid)
15
13
14
15
16
17
18
19
20
21
22
Casuarinin
Chebulanin
Corilagin
Ellagic acid(2,3,7,8-Tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione)
Chebulagic acid
Chebulinic acid (1,3,6-Tri-O-galloyl-2,4-chebuloyl-β-D-glucopyranoside)
1,2,3,4,6-penta-O-galloyl-D-glucose
2,3,4,6-tetra-O-galloyl-B-D-glucose
Ethyl gallate( Ethyl 3,4,5-trihydroxybenzoate)
Methyl gallate (Methyl-3,4,5-trihydroxybenzoate)
16
23
Chebulaginic acid
13
24
25
26
27
28
29
30
4-O-methylgallic acid
Methyl(S)-flavogallonate
Methyl neochebulagate
Eugenol
Ascorbic acid
Triethyl chebulate
Tannic acid [2,3-dihydroxy-5-({[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis({3,4-dihydroxy-5[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)oxan-2yl]methoxy}carbonyl)phenyl 3,4,5-trihydroxybenzoate]
2, 4-Chebulyl-beta-D-glucopyranose
18
31
14
14
14
14
14
14
15
16
16
September-October
16
16
16
16
16
16
17
17
17
18
18
19
19
20
20
21
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OH
OH
HO
HO
O
HO
O
HO
HO
O H
O
O
O
O
HO
O
O
HO
O
HO
OH
HO
OH
Punicalagin (1) HO
OHHO
O
HO
O
O
O
O
OH
O
O
HO
OH
O
O
O
OH
H O
OH
O
O
OH
O
HO
O
OH
O
OH
HO
HO
HO
O
HO
O
O
OH
O
HO
OH
OH
O
O
OH
O O
HO
OH
HO
CH2
OH
O
O
OH
O
O
4513
OH
OH
OH
O
HO
O
OH
HO
Terflavin A (2)
OH
Terchebulin (3)
OH
HO
OH
OH
OH
HO
OH
HO
OH
O
HO
O
OH
OH
O
O
OH
O
OH
O
OH
OH OH
O
O
O
O
HO
HO
OH
O
O
O
OH
O
HO
HO
OH
HO
OH
1,3,6-Trigalloylglucose (4)
O
O
Terflavin B (5) OH
HO
O
OH
OH
O
O
OH
O
O
OH
OH
O
R
O CHO
HO
HO
HO
O
HO
O
O
O
HO
COOH
H OH
O
O
OH
HOOC
OH
HO
OO
HO
HO
OH
OH
OH
HO
O
O
OH
OH
O
O O
O
O
OH
OH
O
HO
O
O
O
OH
O
Ellagic acid (16)
O
O
OH
O
O
OH
O
O
O
HO2C
O
OH
O
HO
HO
O
O
HO
O
O
O
OH
OH
O
O
O
OH
O
OH
O
OH
OH
Chebulinic acid (18)
September-October
HO
HO
O
OH
Chebulagic acid (17)
OH
O
HO
HO
O
OH
OH
O O
O
O
OH HO2C
HO
OH
beta-1-O-galloyl-3,6-(R)hexahydroxydiphenoyld-glucose (15)
OH
O
OH
O
O
Chebulanin 14
OH
O
OH
O
O
OH
OH
O
HO
O
OH
HO
Casuarinin (13)
HO OH OH OH
OH
O
O
O
HO
OH
O
OH
OH
O O
O
HO
OH
HO OH OH OH
OH
O
O
O
HO
HO
O
O
OH HO
O
HO
1,6-Di-O-galloyl-B-D-glucose (11) Gallic acid (12)
HO
O
O
O
OH
OH
O
OH
O
O
O
O
OH
HO
O
HO
OH
OH
O
Chebulic acid (10)
OH
HO
O
HO
OH
OH
OH
O O
HO
HO
O
OH
Neo-chebulinic acid (9)
HO
OH
HOOC
O
Punicalin (8)
OH
OH
OH
O
OH
OH
HO
HOOC
O
HO
O
OH
H
OH
HO
Terflavin D (7)
OH Terflavin C(6)
HO
COOH
O
OH
O
COOH
O OH
O
OH
HO
CH2
OH
HO
O
HO HO
O
OH
O
O
HO
OH
O
O
HO
O
OH
O
HO
O
HO
OH
OH
HO
OH
OH
HO
OH
OH
1,2,3,4,6-Penta-O-galloyl-B-D-glucose (19)
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OH
OH
HO
OH
CO2H
OH
OH
HO
CO2C2H5
HO
O
O
HO
OH
HO
O
OH
Ethyle gallate (21)
OH
HO
OH
HO
OH
OH
HO
OH
HO
OH
HO
OH
OH
OH
H
O
OH
O
OH
Methyl (S)-flavogallonate (25)
Chebulaginic acid (23)
Methyl gallate (22)
O
O
OH
O
HO2C
H3CO2C
OH
HO
OH
Tetra-O-galloyl-B-D-glucose (20)
OH
CO2CH3
H
HO
OH
OH
OH
O
O
O
O
Eugenol (27)
O
O
O
OH
O
O
O
O
4-O-Methylgallic acid (24)
O
CO2CH3
OH
OH
O
O
O
O
HO
OMe
OH
O
O
OH
OH
O
O
O
HO
O
HO
O
HO
O
HO
OH
OH
O
HO
HO
O
HO
OH
OH
HO
OH
O
OH
HO
OH
HO
Methylneochebulagate (26)
OH
O
HO
O
O
O
HO
O O
O
OH
O
O
HO
O
O
O
HO
CH2OH
OH
O
OH
O
O O
O
OH
O
HO
OH
OHO
O
COOC2H5
H OH
C2H5OOC
OH
OH
HO
OH
O
HO
HO
HO
O
OH
O
Triethyl chebulate (29)
O
O
HO2C
O
HO
OH
C2H5OOC
O
O
OH
OH
2,3-Dihydroxy-5-({[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis({3,4dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)oxan-2-yl]methoxy}carbonyl)phenyl 3,4,5trihydroxybenzoat (30)
O
OH
O
OH
2, 4-Chebulyl-beta-Dglucopyranose (31)
Table-2: Phenolic Carboxylic Compounds from Terminalia chebula
Phenolic carboxylic compounds
Shikimic acid
Ferulic acid
Vanillic acid
p-Coumaric acid
Caffeic acids
Melilotic acid
#
32
33
34
35
36
37
O
HO
H3CO
O
HO
OH
O
OH
HO
HO
OH
HO
OCH3
(E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid (33) 4-Hydroxy-3-methoxybenzoic acid (34)
Shikimicacid (32)
O
O
OH
OH
OH
O
OH
HO
HO
OH
(E)-3-(4-Hydroxyphenyl)-2propenoic acid (35)
3-(3,4-Dihydroxyphenyl)-2propenoic acid
(36)
3-(2-Hydroxyphenyl)
propanoic acid (37)
Table-3: Phenols from Terminalia chebula
No.
38
Phenols
Phloroglucinol [benzene-1,3,5-triol ]
Ref.
39
40
Pyragallol [1,2,3-Trihydroxybenzene]
Phenol
22
22
23
September-October
CH2OH
O
OH
Ascorbic acid (28)
O
OH
O
HO
H3CO
HO
Ref.
20
20
20
20
20
22
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HO
OH
HO
HO
HO
HO
OH
Phenol (40)
1,2,3-Trihydroxybenzene (39)
Benzene-1,3,5-triol (38)
Table-4: Triterpenoids and their Saponins from Terminalia chebula
No.
Terpenoids and Triterpene Saponins
41
Arjungenin
42
Arjunolic acid
43
Arjunic acid
44
Terminolic acid
45
Arjunglucoside I
46
Arjunglucoside II
47
Arjunetin
48
Chebuloside II
49
Bellericoside
50
Chebuloside I [2α,3β,23-Trihydroxy-olean-12-en-28-oic Acid]
51
2α-Hydroxyursolic acid
52
2α-Hydroxymicromiric acid
53
Maslinic acid [(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic
acid]
54
β-caryophyllene
55
α-Phellandrene[α: 2-Methyl-5-(1-methylethyl)-1,3-cyclohexadiene]
Ref.
18
18
18
18
18
18
18
18
24
25
25
25
25
19
19
α-Terpinene
Terpinen-4-ol
Terpinolene
Chebupentol [Olean-12-ene-2,3,19,23,28-pentol,(2a,3b,4a,19a)]
56
57
58
59
19
19
19
19
HO
HO
H
HO
H
HO
H
OH
Arjungenin (41)
O
OH
H
HO
H
HO
H
O
OH
H
HO
H
HO
H
OH
Arjunolic acid (42)
Arjunic acid (43)
September-October
O
OH
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OH
HO
O
H
OH
H
HO
H
OH
O
HO
HO
OH
OH
HO
O
OH
OH
OH
HO
O
O
H
HO
O
O
O
H
H
OH
OH
H
HO
HO
O
H
OH
HO
H
Arjunglucosid I (45)
OH
OH
O
HO
H
HO
H
HO
Terminolic acid (44)
OH
Arjunglucoside II (46)
H
Arjunetin (47)
OH
OH
HO
HO
OH
OH
HO
OH
OH
O
O
OH
O
OH
OH
H
HO
O
O
O
H
HO
O
H
HO
H
OH
HO
H
HO
H
OH
HO
H
O
H
Chebuloside II (48)
H
HO
H
HO
OH
OH
HO
O
H
OH
Bellericoside (49)
Chebuloside I (50)
H
(1S,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)10,11-Dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl2,3,4,5,6,6a,7,8,8a,10,11,12,13,14btetradecahydro-1H-picene-4a-carboxylic acid (51)
CO2H
H
HO
H
(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl1,3,4,5,6,6a,7,8,8a,10,11,12,13,14btetradecahydropicene-4a-carboxylic acid (53)
H2C
H
H
OH
a: 2-Methyl-5-(1methylethyl)-1,3- alphaCaryophyllene (54) cyclohexadiene (55) terpinene (56) Terpinen-4-ol (57) Terpinolene (58)
HO
H
HO
CH2OH
H
HO
H
CH2OH
Olean-12-ene-2,3,19,23,28pentol,(2a,3b,4a,19a) (59)
#
60
61
62
63
64
65
66
CO2H
H
Table-5: Flavonoids Isolated from Terminalia chebula
Flavonoids
Ref.
Rutin
Quercetin
Luteolin [2-(3,4-Dihydroxyphenyl)- 5,7-dihydroxy-4-chromenone]
Isoquercetin
[2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one]
3’-Methoxy quercetin
3,4-Dimethoxy
quercetin
[5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3Methoxy-4H-chromen-4-one]
Pelargonidin
September-October
26
27
28
19
21
21
21
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OH
HO
HO
O
OH
OH
OH
OH
O
H
OH
OH
OH
OH
OH
O
OH O
HO
O
H3C
HO
HO
HO
O
O
HO
O
OH
HO
Pelargonidin (66)
O
OH
H
OH
2-(3,4-Dihydroxyphenyl)- 5,7dihydroxy-4-chromenone (62)
Quercetin (61)
O
OH
OH O
OH O
OH
Rutin (60)
OH
OH O
O
HO
OCH3
OH
HO
HO
O
O
OCH3
OCH3
OH O
OH O
3’-Methoxy quercetin (64) 3,4-Dimethoxy quercetin (65)
No.
67
68
Table-7: Sterols Isolated from Terminalia chebula
Ref.
Sterols
β-Sitosterol
Daucosterol
19
29
H
OH
H
H
HO
H
H
HO
HO
17-(5-Ethyl-6-methylheptan-2-yl)-10,13-dimethyl2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1Hcyclopenta[a]phenanthren-3-ol (67)
O
H
H
O
OH H
Daucosterol (68)
Table-6: Miscellaneous Compounds from Terminalia chebula
Miscellaneous compounds
Ref.
19, 23
Behenic acid [Docosanoic acid]
19, 13
Stearic acid [Octadecanoic acid]
13, 23
Palmitic acid [hexadecanoic acid]
13, 23
Oleic acid [(9Z)-Octadec-9-enoic acid]
13, 23
Arachidic acid [icosanoic acid]
13, 23
Linoleic acid [9Z,12Z)-9,12-Octadecadienoic acid]
22
12-Hydroxyoctadec-cis-9-enoic acid (ricinoleic acid)
No.
69
70
71
72
73
74
75
O
O
OH
HO
Palmitic acid (71)
Bhenic acid (69)
O
OH
O
O
HO
HO
Stearic acid (70)
Oleic acid (72)
O
OH
OH
OH
Linoleic acid (74)
Ricinoleic acid (75) O
September-October
OH
OH
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydrox
ymethyl)oxan-2-yl]oxychromen-4-one (63)
OH
OH
O
Arachidic acid (73)
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Table-7. Compounds from Terminalia chebula Fruit
No.
76
77
78
79
80
Compound isolate from Terminalia chebula fruit
2-Undecanone
Cyclododecane
9-Octadecene
Hexadecane
Cylohexane
Ref.
81
82
83
8-Pentadecanone
9-Eicosene
Triacontane
23
84
85
86
Tetradecane
Oxirane
1,16-Hexadecanediol
23
87
88
89
Heptylcyclohexane
10-Nonadecanone
Phthalic acid
23
90
91
92
93
94
95
96
97
98
99
100
101
102
103
104
105
106
107
108
109
110
111
112
113
114
115
Tritetracontane
9-Heptadecanone
Tetratetracontane
Linoleic acid ethyl ester
9-Octadecenoic acid ethyl ester
9,12,15-Octadecatrienoic acid
1-Tricosene
1,19-Eicosadiene
Heptafluorobutyric acid
1-Octanol
1-Decanol
Cyclooctacosane
1H-Indene
Hexacosyl pentafluoropropionate
Octatriacontyl pentafluoroprppionate
Tetratriacontane
1,2-benzenedicarboxylic acid
Ibogamin-9(17H)-ol [(9α)-12-Methoxy-16,17-didehydro-9,17-dihydroibogamin-9-ol]
9-Tricosene
Tetratriacontyl heptafluorobutyrate
Dotricontyl heptafluorobutyrate
Tetracosanoic acid [Lignoceric acid]
Pentatriacontane
Eicosyl trifluoroacetate
Squalene
Tetracosyl heptafluorobutyrate
23
116
117
118
119
120
121
122
123
Tetratriacontyl heptafluorobutyrate
Heptafluorobutyric acid
Sulfurous acid
Octacosanoic acid
Vitamin E
Tetracosyl heptafluorobutyrate
Hexacosanoic acid
Octatriacontyl pentafluoropropionate
23
124
125
126
127
128
129
130
Triacontanoic acid [Melissic acid]
Tricosyl pentafluoropropionate
Acetic acid
Heptacosanoic acid
Tetratriacontyl pentafluoropropionate
Tetracosanoate
Kaempferol-3-rutinoside
23 19
131
Ethanedioic acid
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
23
,
23
23
23
23
23
23
September-October
Sci.Int.(Lahore),28(5),4511-4521,2016
ISSN 1013-5316; CODEN: SINTE 8
4519
O
2-Undecanone (76)
9-Octadecene (78)
Cyclododecane (77)
Hexadecane (79)
Cyclohexane (80)
O
Triacontane (83)
9-Eicosene (82)
8-Pentadecanone (81)
O
Tetradecane (84)
1,16-Hexadecanediol (86)
Oxirane (85)
O
OH
HO
10-Nonadecanone (88)
Heptylcyclohexane (87)
OH
O
HO
O
Phthalic acid (89)
Tritetracontane (90)
O
Tetratetracontane (92)
9-Heptadecanone (91)
O
O
O
O
O
HO
9-Octadecenoic acid ethyl ester (94)
Ethyl linoleate (93)
9,12,15-Octadecatrienoic acid (95)
F
F
F OH
F
F F
1-Tricosene (96)
1,19-Eicosadiene (97)
HO
HO
1-Octanol (99)
1-Decanol (100)
Cyclooctacosane (101) 1H-Indene (102)
F
F
O
O
F
F
F
Hexacosyl pentafluoropropionate (103)
F
F
O
O
Octatriacontyl pentafluoroprppionate (104)
September-October
F
O
Heptafluorobutyric acid (98)
F
F
F
4520
ISSN 1013-5316; CODEN: SINTE 8
Sci.Int.(Lahore),28(5),4511-4521,2016
OH
N
O
O
HO
H
H3CO
N
HO
H
1,2-benzenedicarbo- (9a)-12-Methoxy-16,17-didehydroxylic acid (106)
9,17-dihydroibogamin-9-ol (107)
Tetratriacontane (105)
9-Tricosene (108)
F
FF
O
OF
F
F
F
Tetratriacontyl heptafluorobutyrate (109)
F
O
OF
FF
F
F
F
Dotricontyl heptafluorobutyrate (110)
O
HO
Tetracosanoic acid (111)
Pentatriacontane (112)
F
F
O
O
F
Eicosyl trifluoroacetate (113)
Squalene (114)
F
O
OF
FF
F
F
F
Tetracosyl heptaflourobutyrate (115)
F
FF
O
F
F
F
F OH
F
OF
F
F F
F
F
O
O
HO S
OH
Heptafluorobutyric Sulfurous acid
(118)
acid (117)
Tetratriacontyl heptafluorobutyrate (116)
O
HO
Octacosanoic acid (119)
F
O
OH
O
OF
FF
F
F
F
Tetracosyl heptafluorobutyrate (121)
Vitamin E (120)
O
OH
Hexacosanoic acid (122)
F
F
O
O
F
F
F
Octatriacontyl pentafluoropropionate (123)
F
F
O
O
O
HO
Triacontanoic acid (124)
Tricosyl pentafluoropropionate (125)
September-October
F
F
F
Sci.Int.(Lahore),28(5),4511-4521,2016
ISSN 1013-5316; CODEN: SINTE 8
4521
OH
O
HO
O
OH O
OH
O
OH
H3C
O
O
OH
O
OH
HO
HO
O
Acetic acid (126)
OH
OH
O
HO
O
HO
Heptacosanoic acid (127)
kaempferol-3-rutinoside Ethanedioic acid (131)
F
F
O
O
Tetratriacontyl pentafluoropropionate (128)
CONCLUSION:
In light of role of nature engineered secondary metabolites in
pharmaceuticals, the structural and functional diversity and
novelty of natural products of Terminalia chebula along with
the rich and diverse biosynthesis, together with their wide
range of therapeutic applications, and importantly its valuable
anti-pathogenic biological properties coupled with the
burnings needs for new antibiotics, we conclude and propose:
1). Focused and guided phytochemical re-investigations on
the Terminalia chebula and its herbal products, 2). Structure
activity relation (SAR) further medicinal chemistry to explore
the drug potentials of already known bioactive molecules of
Terminalia chebula, especially anti-microbial agents. 3).
Further studies for the standardization, formulation,
documentation, efficacy and safety of traditional herbal
medicinal products (THMPs) of Terminalia chebula. Hence,
it is crucial to be shared with the relevant scientists.
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