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Context: Terminalia is the second largest genus of family Combretaceae. The plants of this genus were used in traditional folk medicine worldwide. Objectives: This review is a comprehensive literature survey of different Terminalia species regarding their biological activities and their isolated phytochemicals. The aim of this review is to attract the attention to unexplored potential of natural products obtained from Terminalia species, thereby contributing to the development of new therapeutic alternatives that may improve the health of people suffering from various health problems. Materials and methods: All the available information on genus Terminalia was compiled from electronic databases such as Medline, Google Scholar, PubMed, ScienceDirect, SCOPUS, Chemical Abstract Search and Springer Link. Results: Phytochemical research has led to the isolation of different classes of compounds including, tannins, flavonoids, phenolic acids, triterpenes, triterpenoidal glycosides, lignan and lignan derivatives. Crude extracts and isolated components of different Terminalia species showed a wide spectrum of biological activities. Conclusion: phytochemical studies on genus Terminalia have revealed a variety of chemical constituents. Numerous biological activities have validated the use of this genus in treatment of various diseases in traditional medicine. Further studies are needed to explore the bioactive compounds responsible for the pharmacological effects and their mechanism of action.
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Research Article Open Access
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Open Access
Review Article
Medicinal & Aromatic Plants
Fahmy et al., Med Aromat Plants 2015, 4:5
http://dx.doi.org/10.4172/2167-0412.1000218
*Corresponding author: Singab AN, Department of Pharmacognosy, Faculty
of Pharmacy, Ain Shams University, 11566, Cairo, Egypt. Tel: +20224051120;
Fax: +20224051107; E-mail: dean@pharma.asu.edu.eg
Received October 17, 2015; Accepted November 23, 2015; Published November
26, 2015
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A
phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants 4:
218. doi:10.4172/2167-0412.1000218
Copyright: © 2015 Fahmy NM, et al. This is an open-access article distributed
under the terms of the Creative Commons Attribution License, which permits
unrestricted use, distribution, and reproduction in any medium, provided the
original author and source are credited.
Genus Terminalia: A phytochemical and Biological Review
Fahmy NM, Al-Sayed E and Singab AN*
Department of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, Cairo, 11566, Egypt
Keywords: Terminalia; Tannins; Flavonoids; Terpenoids;
Combretaceae; Traditional medicine
Abbreviations:A549: Human lung epithelial cancer; AChE:
Acetylcholinesterase; ACP: Acid phosphatase; ALP: Alkaline phosphatase;
ALT: Alanine aminotransferase; AST: Aspartate aminotransferase; Bw:
Body weight ; COLO-205: Human colon cancer ; COX-2: Cyclooxygenase-2
enzyme; DPPH•: 2;2-diphenyl-1-picrylhydrazyl radical; DU-145: Human
prostate cancer; FRAP: Ferric reducing ability of plasma; GSH: Glutathione;
HbA1c: Glycated hemoglobin; HCT-15: Human colorectal cancer; HL-60:
Human promyelocytic leukemia ; IMR: Ischemic mitral regurgitation;
iNOS: inducible nitric oxide synthase ; K562: Human immortalised
myelogenous leukemia; MBC: Minimum bactericidal concentration;
MDA-MB-231:M.D.anderson-metastatic breast cancer; MIC: Minimum
inhibitory concentration; ORAC: Oxygen radical absorbance capacity;
PPARα / PPARγ: Peroxisome proliferator-activated receptor alpha/ gamma
; STZ: Streptozotocin; T: Terminalia
Introduction
e genus Terminalia is the second largest genus of the Combretaceae
aer Combretum, with about 200 species. ese plants are distributed
in tropical regions of the world with the greatest genetic diversity
in Southeast Asia [1]. Genus Terminalia gets its name from Latin
terminus, since the leaves appear at the tips of the shoots [2]. Terminalia
species range from shrubs to large deciduous forest trees. Mostly they
are very large trees reaching in height up to 75 m tall [3]. Members
of the genus Terminalia are widely used in traditional medicine in
several continents in the world for the treatment of numerous diseases
including, abdominal disorders, bacterial infections, colds, sore throats,
conjunctivitis, diarrhea, dysentery, fever, gastric ulcers, headaches,
heart diseases, hookworm, hypertension, jaundice, leprosy, nosebleed,
edema, pneumonia and skin diseases [4]. e fruits of both T. bellerica
and T. c h ebula are important components of triphala, a popular
Ayurvedic formulation that possess numerous activities in the Indian
traditional medicine [5]. T. c hebu l a fruit possess an extraordinary
power of healing and is called the “King of Medicine” in Tibet as it’s
used for the treatment of various diseases [6,7]. e Bark of T. a r j una
are used as cardioprotective and anti-hyperlipidemic in folklore
Abstract
Context: Terminalia is the second largest genus of family Combretaceae. The plants of this genus were used in
traditional folk medicine worldwide.
Objectives: This review is a comprehensive literature survey of different Terminalia species regarding their
biological activities and their isolated phytochemicals. The aim of this review is to attract the attention to unexplored
potential of natural products obtained from Terminalia species, thereby contributing to the development of new
therapeutic alternatives that may improve the health of people suffering from various health problems.
Materials and methods: All the available information on genus Terminalia was compiled from electronic databases
such as Medline, Google Scholar, PubMed, ScienceDirect, SCOPUS, Chemical Abstract Search and Springer Link.
Results: Phytochemical research has led to the isolation of different classes of compounds including, tannins,
avonoids, phenolic acids, triterpenes, triterpenoidal glycosides, lignan and lignan derivatives. Crude extracts and
isolated components of different Terminalia species showed a wide spectrum of biological activities.
Conclusion: phytochemical studies on genus Terminalia have revealed a variety of chemical constituents.
Numerous biological activities have validated the use of this genus in treatment of various diseases in traditional
medicine. Further studies are needed to explore the bioactive compounds responsible for the pharmacological effects
and their mechanism of action.
medicine [8]. In Africa, T. mol l i s is used to treat diarrhea, gonorrhea,
malaria, and in HIV treatment, while T. brachystemma is used for the
treatment of shistosomiasis and gastrointestinal disorders [9]. e
diverse phytochemical constituents and various biological activities
attracted us to perform a comprehensive literature survey of dierent
Terminalia species regarding their phytochemical constituents, their
ability to exert biological activities and the evidence-based information
regarding the phytochemistry and biological activities of this genus.
e present review is divided into two main sections, the rst include
a phytochemical review of various chemical constituents and their
occurrence within the Terminalia species, the second comprises the
numerous biological studies conducted for dierent species of the
genus Terminalia.
Phytochemical Studies
Phytochemical studies performed on dierent Terminalia
species have demonstrated the occurrence of several classes of active
constituents, such as tannins, pentacyclic triterpenes and their glycoside
derivatives, avonoids and other phenolic compounds [10].
Literature survey has revealed that genus Terminalia is a rich
source of tannins and pseudotannins, including gallic acid and its
simple gallate esters, chebulic and non-chebulic ellagitannins, ellagic
acid derivatives and ellagic acid glycosides (Table 1 and Figure 1).
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 2 of 21
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
No. Compound Species Part used (Type of extract) Reference (s)
A. Gallic acid and simple gallate esters
1 Gallic acid
T. chebula
T. bellerica
T. horrida
T. muelleri
T. nigrovenulosa
T. arjuna
T. superba
T. macroptera
T. mollis
T. catappa
T. oblongata
T. pallida
T. stenostachya
T. myriocarpa
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves, fruits, bark (MeOH)
Bark (EtOAc)
Leaves (EtOH), fruits, bark
Stem bark (CH2Cl2: MeOH)
Leaves
Leaves (MeOH)
Leaves (H2O)
Leaves
Fruits (EtOH)
Leaves
Leaves
[27, 82]
[27]
[27]
[28, 50]
[52]
[83, 84]
[18]
[54]
[9]
[85]
[86]
[87]
[49]
[88]
2 Methyl gallate
T. chebula
T. bellerica
T. horrida
T. superba
T. myriocarpa
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Stem bark (CH2Cl2: MeOH)
Leaves
[27]
[27]
[27]
[18]
[88]
3 Ethyl gallate
T. arjuna
T. chebula
T. myriocarpa
Arial parts (MeOH)
Leaves
Leaves
[64]
[59]
[88]
4 1,6-di-O-galloyl-β--Glc
T. chebula
T. bellerica
T. horrida
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 82]
[27]
[27]
53,4,6-tri-O-galloyl-β--Glc
T. chebula
T. bellerica
T. horrida
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 82]
[27]
[27]
61,3,4,6-tetra-O-galloyl-β--Glc
T. chebula
T. bellerica
T. horrida
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 82]
[5, 27]
[27]
72,3,4,6-tetra-O-galloyl-β--Glc T. arjuna Leaves (EtOH) [83]
81,2,3,4,6-penta-O-galloyl-β--Glc
T. chebula
T. bellerica
T. horrida
T. arjuna
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (EtOH)
[27, 82]
[27]
[27]
[83]
9 3,4,5-tri-O-galloyl-shikimic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
B. Chebulic acid and chebulic ellagitannins
10 Chebulic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH, EtOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 33]
[27]
[27]
11 Neo-chebulic acid T. chebula Fruits (EtOH) [33]
12 Chebulanin
(1-O-galloyl-2,4-O-chebuloyl-β--Glc)
T. chebula
T. bellerica
T. horrida
T. brachystemma
T. mollis
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (MeOH)
Leaves (MeOH)
[12, 27]
[27]
[27]
[9]
[9]
13
Chebulinic acid
(1,3,6-tri-O-galloyl-2,4-O-chebuloyl-β-
-Glc)
T. bellerica
T. chebula
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[12, 27]
[27]
14 Methyl neo-chebulanin
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27, 60]
[27]
[27]
15
Methyl neochebulinate T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
16
Chebulagic acid
(1-O-galloyl-2,4-O-chebuloyl-3,6-O-
HHDP-β--Glc)
T. chebula
T. bellerica
T. horrida
T. catappa
Fruits (MeOH), seeds
Fruits (MeOH)
Fruits (MeOH)
Leaves (H2O)
[27, 89]
[5, 27]
[27]
[34]
17 Methyl neochebulagate
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
18 1,6-di-O-galloyl-2,4-O-chebuloyl-β--Glc
(or 1,3-)
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
C. Non-chebulic ellagitannins
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 3 of 21
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
19 Tellimagrandin(I)
(2,3-di-O-galloyl-4,6-O-HHDP-α/β--Glc)
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
20 Corilagin
(1-O-galloyl-3,6-O-HHDP-β--Glc)
T. chebula
T. bellerica
T. horrida
T. catappa
Fruits (MeOH, EtOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (H2O)
[27, 90]
[27]
[27]
[34]
21 Tercatain
(1,4-di-O-galloyl-3,6-O-HHDP-β--Glc) T. catappa Leaves (Acetone) [91]
22 Arjunin
(3-O-galloyl-4,6-O-gallagyl-α/β--Glc) T. arjuna Leaves (EtOH) [83]
23 Punicalin
(4,6-O-gallagyl-α/β--Glc)
T. bellerica
T. chebula
T. horrida
T. arjuna
T. catappa
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (EtOH)
Leaves (Acetone)
[27]
[27]
[27]
[83]
[91]
24 Punicalagin
(2,3-O-HHDP-4,6-O-gallagyl-α/β--Glc)
T. chebula
T. bellerica
T. horrida
T. oblongata
T. brachystemma
T. macroptera
T. catappa
T. arjuna
T. myriocarpa
Leaves (H2O), fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (H2O)
Leaves (Acetone)
Roots (EtOH)
Leaves (Acetone, H2O)
Bark
Leaves
[27, 90]
[27]
[27]
[92]
[9]
[55]
[61, 91]
[93]
[88]
25 2,3:4,6-bis-O-HHDP-1-O-galloyl-β--Glc T. arjuna Leaves (EtOH) [83]
26 Tergallagin T. catappa Leaves (Acetone) [91]
27
Teravin (A)
(4-O-avogallonyl-6-O-galloyl-2,3-O-
HHDP-α/β--Glc)
T. chebula
T. catappa
T. macroptera
Fruits (H2O)
Leaves (Acetone)
Stem bark (EtOAc)
[90]
[91]
[94]
28 Teravin (B)
(4-O-avogallonyl-6-O-galloyl-α/β--Glc)
T. chebula
T. bellerica
T. horrida
T. catappa
T. macroptera
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves (Acetone)
Stem Bark (EtOAc)
[27]
[27]
[27]
[91]
[94]
29
Teravin (C)
(4-O-avogallonyl -2,3-O-HHDP-α/β-
-Glc)
T. chebula
T. catappa
T. arjuna
Fruits (H2O)
Leaves (Acetone)
Bark
[90]
[91]
[93]
30
Calamansanin
(4-O-avogallonyl-6-O-galloyl-2,3-O-
HHDP-α--Glc)
T. calamansanai Leaves [93]
31 Terchebulin
T. chebula
T. macroptera
T. arjuna
Fruits (H2O)
Roots (EtOH)
Bark
[90, 95]
[55]
[93]
32 Isoterchebulin T. macroptera Stem bark (EtOAc) [94]
33 4,6-O-isoterchebuloyl-α/β--Glc T. macroptera Stem bark (EtOAc) [94]
34 Casurarinin T. chebula
T. arjuna
Fruits (H2O)
Bark (Acetone)
[90]
[48]
35 Casuariin T. arjuna Bark [96]
36 Castalagin T. arjuna Leaves [93]
D. Ellagic acid and ellagic acid derivatives
37 Ellagic acid
T. chebula
T. bellerica
T. horrida
T. muelleri
T. arjuna
T. superba
T. macroptera
T. pallida
T. paniculata
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Bark, fruits (MeOH)
Leaves (EtOH), fruits
Stem bark (CH2Cl2: MeOH)
Leaves
Fruits (EtOH)
Heartwood (alc.)
[27]
[27]
[27]
[28]
[83, 84]
[18]
[54]
[87]
[97]
38 3-O-methyl ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
39 3,3’-di-O-methyl ellagic acid
T. chebula
T. bellerica
T. horrida
T. superba
T. paniculata
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Stem bark (CH2Cl2: MeOH)
Heart wood (alc.)
[27]
[27]
[27]
[18]
[97]
40 3,4,4-tri-O-methyl ellagic acid T. catappa Fruits, Leaves (EtOH) [98]
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 4 of 21
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Phenolic acids (Table 2 and Figure 2), avonoids (Table 3 and Figure
3), triterpenes and triterpenoidal glycosides (Table 4 and Figure 4) are
also present in high amounts in various Terminalia species, few lignan
and lignan derivatives have been isolated from genus Terminalia (Table
5 and Figure 5).
Biological Studies
Screening of available literature on genus Terminalia revealed
numerous biological activities in various in vivo and in vitro models.
Biological activities included anti-diabetic, anti-hyperlipidemic,
antioxidant, anti-bacterial, anti-fungal, anti-viral, anti-inammatory,
anti-cancer, anti-ulcer, anti-parasitic, hepatoprotective and
cardioprotective activities.
Anti-diabetic activity
T. ch ebula showed a strong anti-diabetic activity, compounds isolated
from the fruits, such as corilagin and ellagic acid acted as α-glucosidase
inhibitors [11]. Additionally, chebulanin, chebulagic acid and chebulinic
acid possessed a potent intestinal maltase inhibitory activity, with IC50
values of 690 μM, 97 μM and 36 μM, respectively [12]. In another study,
T. che bu la fruits and seeds exhibited a dose-dependent reduction in blood
glucose in STZ-induced diabetic rats [13]. Furthermore, ellagitannins
and gallotannins isolated from T. bellerica and T. c h ebula fruit extracts
enhanced the PPARα and/or PPARγ signaling [5]. e aqueous extract of
T. paniculata bark reduced the elevated blood glucose, HbA1c, creatinine,
urea, ALT, AST levels and reversed the abnormal status of endogenous
antioxidants and the lipid prole levels towards their normal levels in
STZ-induced diabetic rats in comparison with the untreated diabetic
rats [14]. Nampoothiri [15] reported that the methanolic extract of T.
bellerica fruits exhibited a potent α-amylase and α-glucosidase inhibitory
activities. Moreover, the anti-diabetic activity of T. bellerica fruit extract
is attributed to its gallic acid content, as it induced a dose-dependent
reduction in blood glucose level with a simultaneous increase in plasma
insulin (62.92%), C-peptide (79.74%), total protein (42.41%) and albumin
(51.52%) in STZ-induced diabetic rats when compared to the untreated
41 3,4,8,9,10-Pentahydroxydibenzo[b,d]
pyran-6-one
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
42 Flavogallonic acid
T. chebula
T. bellerica
T. horrida
T. myriocarpa
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves
[27]
[27]
[27]
[88]
43 Methylavogallonate
T. chebula
T. bellerica
T. horrida
T. myriocarpa
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Leaves
[27]
[27]
[27]
[88]
44 3,4,3-O-trimethyl avellagic acid T. paniculata Heartwood (alc) [97]
45 Gallagic acid.
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
E. Ellagic acid glycosides
46 3’-O-methyl-4-O-(β--xylopyranosyl)
ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
47 3,3’-di-O-methyl-4-O-(β--xylopyranosyl)
ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
48
3’-O-methyl-4-O-(n”-O-galloyl-β--
xylopyranosyl) ellagic acid (n = 2, 3,
or 4)
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
49
3,3’-di-O-methyl-4-O-(n”-O-galloyl-β-
-xylopyranosyl) ellagic acid. (n = 2, 3,
or 4)
T. chebula
T. bellerica
T. horrida
T. superba
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
Stem bark (CH2Cl2: MeOH)
[27]
[27]
[27]
[18]
50 4’-O-galloyl-3,3’-di-O-methyl-4-O-(β--
xylopyranosyl) ellagic acid T. superba Stem bark (MeOH) [56]
51 3’,4-di-O-methyl-3-O-(β--xylopyranosyl)
ellagic acid T. superba Stem bark (MeOH) [56]
52 3’-O-methyl-4-O-(α-L- rhamnopyranosyl)
ellagic acid
T. arjuna
T. mollis
Bark (MeOH)
Stem bark (MeOH)
[99]
[9]
53 4-O-(4”-O-galloyl-α-L-rhamnopyranosyl)
ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
54 4-O-(3”,4”-di-O-galloyl-α-L-
rhamnopyranosyl) ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
55 3’-O-methyl-4-O-(3”,4”-di-O-galloyl-α-L-
rhamnopyranosyl) ellagic acid
T. chebula
T. bellerica
T. horrida
Fruits (MeOH)
Fruits (MeOH)
Fruits (MeOH)
[27]
[27]
[27]
56
3,3-di-O-methyl-4-O-(β-D-
glucopyranosyl-(1→4)-β-D-
glucopyranosyl-(1→2)-α-L-
arabinopyranosyl) ellagic acid
T. alata Roots [58]
Table 1: Tannins and pseudotannins and their occurrence within Terminalia species.
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 5 of 21
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 6 of 21
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
Figure 1: Chemical structures of tannins and pseudotannins isolated from different Terminalia species.
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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No. Compound Species Part used (Type of extract) Reference (s)
57 Caffeic acid T. chebula Leaves [90]
58 Ferulic acid T. chebula
T. catappa
Leaves
Fruits, leaves (EtOH)
[90]
[98]
59 Vanillic acid T. chebula
T. catappa
Leaves
Fruits, leaves (EtOH)
[90]
[98]
60 Coumaric acid T. chebula
T. catappa
Leaves, fruits
Leaves (H2O)
[90]
[85]
61 p-hydroxybenzoic acid T. catappa Leaves (H2O) [85]
62 3,4-dihydroxybenzoic acid T. nigrovenulosa
T. catappa
Bark
Leaves (H2O)
[75]
[85]
Table 2: Phenolic acids and their occurrence within Terminalia species.
Figure 2: Chemical structures of phenolic acids isolated from different Terminalia species.
No. Compound Species Part used (Type of extract) Reference (s)
A. Flavonols
63 Quercetin
T. arjuna
T. muelleri
T. macroptera
T. bellerica
T. chebula
Fruits (MeOH)
Bark, fruits, leaves (MeOH)
Leaves
Bark, fruits, leaves (MeOH)
Leaves
[28]
[28]
[54]
[28]
[100]
64 Kaempferol T.arjuna Bark [101]
65 Kaempferol 3-O-rutinoside T. myriocarpa Leaves [88]
66 Rutin
(Quercetin-3-O-rutinoside)
T. chebula
T. myriocarpa
Leaves
Leaves
[100]
[88]
B. Flavones
67 Luteolin T. arjuna
T. chebula
Arial parts (MeOH)
Fruits
[64]
[59]
68 Apigenin T. arjuna Leaves (MeOH) [102]
69
Arjunolone
(6,4’-dihydroxy-7-O-methyl-
avones)
T. arjuna Stem bark [103, 104]
70 Baicalein
(5,6,7-trihydroxy-avones) T. arjuna Stem bark [103, 104]
71 Orientin
T. mollis
T. catappa
T. myriocarpa
Leaves (Acetone)
Leaves
Leaves
[9]
[105]
[88]
72 Isoorientin
T. brachystemma
T. catappa
T. macroptera.
T. myriocarpa
Leaves (Acetone)
Leaves
Leaves
Leaves
[9]
[105]
[54]
[88]
73
Vitexin T. arjuna
T. catappa
T. myriocarpa
Leaves (MeOH)
Leaves
Leaves
[102]
[105]
[88]
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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diabetic rats [16]. e ethanolic leaf extracts of T. arjuna, T. catappa, T.
bellerica and T. cheb u l a had a potent α-glucosidase inhibition activity
[17]. Gallic acid and methyl gallate isolated from T. superba stem bark
showed a signicant α-glucosidase inhibitory activity [18]. Additionally,
the methanolic and the aqueous extracts of T. cata p p a fruits exhibited
signicant anti-hyperglycemic activities and showed an improvement
in body weight and lipid prole as well as regeneration of β-cells of the
pancreas [19]. Also, T. pallida fruit extract showed a signicant anti-
diabetic activity in alloxan-induced diabetic rats at a dose of 0.50 g/kg
bw [20].
Anti-hyperlipidemic activity
e oral administration of gallic acid isolated from T. bellerica
fruit at a dose of 20 mg/kg bw signicantly reduced the serum total
cholesterol, triglyceride and LDL-cholesterol levels [21]. Moreover, T.
chebula f ruits possessed anti-hyperlipidemic activity against cholesterol-
induced hypercholesterolemia and atherosclerosis in rabbits [22]. In
addition, the ethanolic extract of T. a r juna tree bark reduced the serum
total cholesterol, LDL, VLDL, triglycerides and raised HDL levels in
diet-induced hyperlipidemic rabbits [23]. Also, it was shown that T.
bellerica, T. chebula and T.ar ju n a had anti-hyperlipidemic activities T.
arjuna the most potent one caused an inhibition of rabbit atheroma
aer oral administration in hyperlipidemic rabbits [24].
Antioxidant activity
Most Terminalia species were reported to possess an antioxidant
activity. e antioxidant activity of the T. arjuna bark was studied and
the results of DPPH assay, superoxide radical scavenging activity and
lipid peroxidation assay were comparable with the standard antioxidant
ascorbic acid [25]. T. che b ula fruit extract possessed a potent
antioxidant activity and can be used as a radio-protector as it protected
from γ-irradiation-induced oxidative stress in rats by the reduction of
radiation-induced cellular DNA damage [26].
e antioxidant activities of the methanolic fruit extract of T.
bellerica and its isolated compounds was examined using DPPH,
oxygen radical absorbance capacity (ORAC) and ferric reducing ability
of plasma (FRAP) in vitro assays. Chebulic ellagitannins showed the
highest antioxidant activity [27]. Moreover, the high antioxidant
activity of the aqueous methanolic extracts of the leaves, bark and fruits
of T. ar j u na, T. bellerica, T. chebula and T. muelleri were attributed to
their high phenolic contents (72.00-167.20 mg/g) [28].
74 Isovitexin
T. arjuna
T. brachystemma
T. catappa
T. myriocarpa
Leaves (MeOH)
Leaves (Acetone)
Leaves
Leaves
[102]
[9]
[105]
[88]
75 2”-O-galloylvitexin T. mollis
T. catappa
Leaves (MeOH)
Leaves
[9]
[105]
76 2”-O-galloylisovitexin T. catappa Leaves [105]
77 Arjunone
(5,7,2’,4’-tetra-O-mrthyl-avones) T. arjuna Fruits (EtOH) [106]
C. Flavans
78 7,3-dihydroxy-4-O-methyl-avan T. argentea Bark (EtOH) [107]
79 7,4’-dihydroxy-3’-O-methyl-avan T. argentea Bark (EtOH) [107]
80 7-hydroxy-3’,4’-methylenedioxy-
avan T. bellerica Fruits [108]
D. Flavanones
81 8-methyl-5,7,2,4-tetra-O-methyl-
avanone T. alata Roots (EtOH) [109]
82
5,7,2-tri-O-methyl-avanone
4-O-α-L-rhamnopyranosyl-(1→4)-
β--glucopyranoside
T. alata Roots [58]
E. Flavan-3-ol
83 Catachin
T. arjuna
T. mollis
T. brachystemma
Leaves, stem bark
Stem bark (MeOH)
Leaves (Acetone)
[84]
[9]
[9]
84 Gallocatechin
T. arjuna
T. catappa
T. mollis
Stem bark
Bark
Stem bark (MeOH)
[84]
[93]
[9]
85 Epicatechin
T. arjuna
T. catappa
T. mollis
Stem bark
Bark
Stem bark (MeOH)
[84]
[93]
[9]
86 3-O-galloyl-epicatechin T. catappa Bark [93]
87 Epigallocatechin
T. arjuna
T. catappa
T. mollis
Stem bark
Bark
Stem bark (MeOH)
[84]
[93]
[9]
88 3-O-galloyl-epigallocatechin T. catappa Bark [93]
F. Chalcones
89 2-O-β--glucosyloxy-4,6,2,4-
tetramethoxychalchone T. alata Roots (EtOH) [109]
G. Anthocyanidins
90 Pelargonidin T. arjuna Bark [101]
H. Leucoanthocyanidins
91 Leucocyanidin T. arjuna Bark (MeOH) [110]
Table 3. Flavonoids and their occurrence within Terminalia species.
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 9 of 21
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Figure 3: Chemical structures of avonoids isolated from different Terminalia species.
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 10 of 21
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ISSN: 2167-0412 MAP, an open access journal
No. Compound Species Part used (Type of extract) Reference (s)
A. Triterpenes
92 Ursolic acid T. brachystemma
T. catappa
Leaves (n-hexane)
Leaves (EtOH)
[9]
[42]
93 2α-hydroxyursolic acid T. chebula
T. mollis
Leaves (Acetone)
Stem bark (n-hexane)
[111 ]
[9]
94 2α,3β,23-trihydroxyurs-12-en-28-oic acid T. catappa Leaves (EtOH) [42]
95 Asiatic acid T. brassii
T. complanata
Wood (Et2O)
Wood (Et2O)
[112]
[112]
96 Oleanolic acid T. arjuna
T. superba
Root bark
Stem bark (CH2Cl2: MeOH)
[84]
[18]
97 Methyl oleonate T.arjuna Fruits [106]
98 Arjunic acid T. arjuna
T. macroptera
Fruits, roots, stem bark
Bark
[84, 113],
[114]
99 Arjunolic acid
(2α,3β,23-trihydroxyolean-12-en-28-oic aid)
T. arjuna
T. brassii
T. complanata
Bark (pet. ether)
Wood (Et2O)
Wood (Et2O)
[32]
[112]
[112]
100 23-O-galloyl-arjunolic acid T. macroptera Stem bark (EtOAc) [114]
101 Arjungenin
(2α,3β,19α,23-tetrahydroxyolean-12-ene-28-oic acid)
T. arjuna
T. bellerica
T. macroptera
Bark (EtOH)
Stem bark (MeOH)
Bark
[113]
[115]
[114]
102 Tomentosic acid
(2α,3β,19β,23-tetrahydroxyolean-12-ene-28-oic acid)
T. arjuna
T. tomentosa (T.
alata)
Stem bark
Heart wood
[84]
[116]
103 Sericic acid
(2α,3β,19α,24-tetrahydroxy-olean-12-en-28-oic acid)
T. sericea
T. macroptera
Roots
Stem bark
[117]
[114]
104 Belleric acid
(2α,3β,23,24-tetrahydroxy-olean-12-en-28-oic acid) T. bellerica Stem bark (MeOH) [115]
105 Bellericagenin A
(2α,3β,7α,23-tetrahydroxyolean-12-en-28-oic acid) T. bellerica Stem bark [118]
106 Bellericagenin B
(2α,3β,19α,23,24-pentahydroxyolean-12-en-28-oic acid) T. bellerica Stem bark [118]
107 Terminolic acid
(2α,3β,6β,23-tetrahydroxyolean-12-en-28-oic acid)
T. macroptera
T. glaucesence
T. catappa
T. laxiora
T. avicennioides
Stem bark
Heartwood (Et2O)
Heartwood (Et2O)
Heartwood (Et2O)
Heartwood (Et2O)
[114]
[119]
[119]
[119]
[119]
108 Maslinic acid
(2α,3β-dihydroxyolean-12-en-28-oic acid) T. chebula Leaves (Acetone) [111 ]
109 3-acetylmaslinic acid T. alata Root bark [120]
110 2α-hydroxymicromeric acid T, chebula Leaves (Acetone) [111]
111 Terminic acid
(3β,13β-dihydroxylup-20-en-28-oic acid) T. arjuna Root bark (n-hexane) [121]
112 Friedelin
T. arjuna
T. glaucescens
T. mollis
T. alata
Fruits
Stem bark
Stem bark (n-hexane)
Roots
[106]
[122]
[9]
[58]
113 β-sitosterol
T. chebula
T. superba
T. bellerica
T. glaucescens
T. phanerophlebia T.
sambesiaca
T. arjuna
Stem bark
Stem bark ( CH2Cl2: MeOH)
Fruits
Stem bark
Leaves (EtOH)
Leaves
Stem bark, fruits
[123]
[18]
[124]
[122]
[36].
[125]
[84]
114 β-sitosterone T. phanerophlebia Leaves (EtOH) [36]
115 Stigmasterol
T. superba
T. glaucescens
T. arjuna
Stem bark (CH2Cl2: MeOH)
Stem bark
Leaves (MeOH)
[18]
[122]
[102]
116 Stigma-4-ene-3,6-dione T. phanerophlebia Leaves (EtOH) [36]
117 Terminalin A T. glaucescens Stem bark [122]
B. Triterpenoidal glycosides
118 2α,3β-dihydroxyurs-12,18-dien-28-oic acid-28-O-β--glucopyranoside T. arjuna Bark (MeOH) [99]
119 2α,3β,23 trihydroxyurs-12,18-dien-28-oic acid-28-O-β--glucopyranoside T. arjuna Bark (MeOH) [99]
120 2α,3β,23 trihydroxyurs-12,19-dien-28-oic acid-28-O-β--glucopyranoside T. arjuna Bark (MeOH) [99]
121 Quadranoside VIII
(2α,3β,23-trihydroxyurs-12,19-dien-28-oic acid-28-O-β--glucopyranoside) T. arjuna Bark (MeOH) [99]
122 Kajiichigoside F1
(2α,3β,19α-trihydroxyurs-12-en-28-oic acid-28-β--glucopyranoside) T. arjuna Bark (MeOH) [99]
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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123 Arjunetin
(2α,3β,19α-trihydroxyolean-12-en-28-oic acid-28-β--glucopyranoside)
T. argentea
T. arjuna
Bark (EtOH)
Stem, root bark (EtOH)
[107]
[113, 126]
124
Arjunosides (I)
(3-O-β--galactoside of arjunic acid)
Arjunosides (II)
(3-O-β--glucosyl-2-deoxy-α-L-rhamnoside of arjunic acid)
Arjunosides (III)
(28-β--glucuronopyranoside of arjunic acid)
Arjunosides (IV)
(3-O-α-L-rhamnoside of arjunic acid)
T. arjuna Root bark (EtOAC, MeOH) [84, 126]
125 2α,3β,19α-trihydroxyolean-12-en-28-oic acid-methylester-3-O-rutinoside T. alata Roots (EtOH) [109]
126 2α,3β,19α-trihydroxyolean-12-en-28-oic acid-3-O-β--galactopyranosyl- (1→3)-β--
glucopyranoside T. alata Roots [127]
127 2α,3β,19β,23-tetrahydroxyolean-12-en-28-oic acid 3-O-β--galactopyranosyl-(1→3)-
β--glucopyranoside-28-O-β--glucopyranoside T. alata Roots [58]
128
Arjunolitin
(2α,3β-23-trihydroxyolean-12-en-28-oic acid-3-O-β--glucopyranosyl-28-O-β--
glucopyranoside)
T. arjuna Stem bark [110]
129 Tormentic acid-β--glucopyranoside T. argentea Bark (EtOH) [107]
130 Chebuloside (I)
(2α,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β--galactopyranoside) T. chebula Stem bark (MeOH) [123]
131 Chebuloside (II)
(2α,3β,6β,23-tetrahydroxyolean-12-en-28-oic acid-28-O-β- glucopyranoside) T. chebula Stem bark (MeOH) [123]
132 23-galloylarjunolic acid-28-O-β--glucopyranoside T. macroptera Stem bark (MeOH) [114]
133 Arjunglucoside (I)
(2α,3β,19α,23-tetrahydroxyolean-12-en-28-oic acid-28-O-β--glucopyranoside)
T. bellerica
T. chebula
T. tropophylla
T. macroptera
T. arjuna
Fruits, Stem bark
Stem bark (MeOH)
Roots (EtOH)
Bark
Stem bark
[115]
[123]
[128]
[114]
[126, 129]
134 Arjunglucoside (II)
(2α,3β,23-trihydroxyolean- 12-en-28-oic acid-28-O-β--glucopyranoside) T. arjuna Stem bark [129]
135 Terminoside (A)
(1α,3β,22β-trihydroxyolean-12-en-28-oic acid-3-O-β--glucopyranoside) T. arjuna Bark (EtOH) [130]
136 Termiarjunoside (I)
(1α,3β,9α,22α-tetrahydroxyolean-12-en-28-oic acid-3-O-β--glucopyranoside) T. arjuna Bark (EtOH) [131]
137 Termiarjunoside (II)
(3α,5α,25-trihydroxyolean-12-en-23,28-dioic acid-3-O-α --glucopyranoside) T. arjuna Bark (EtOH) [131]
138 Sericoside
(2α,3β,19α,24-tetrahydroxy-olean-12-en-28-oic acid -28-O-β- -glucopyranoside)
T. sericea
T. tropophylla
T. macroptera
T. ivorensis
Roots
Roots (EtOH)
Stem bark
Bark
[117]
[128]
[114]
[65]
139
Ivorenoside (A)
(Dimer of 18,19-seco-2α,3β,19,19,24-pentahydroxyolean-12-en-28-oic acid-28-O-β-
-glucopyranoside and 2α,3β,19α,24-tetrahydroxyolean-12-en-28-oic acid-28-O-β--
glucopyranoside)
T. ivorensis Bark [65]
140
Ivorenoside (B)
(Dimer of 18,19-seco-24-carboxyl-2α,3β,19,19-tetrahydroxyolean-12-en-28-oic acid-
28-O-β--glucopyranoside and 2α,3β,19α,24-tetrahydroxyolean-12-en-28-oic acid-28-
O-β--glucopyranoside)
T. ivorensis Bark [65]
141
Ivorenoside (C)
(2α,3β,19β,24-tetrahydroxyolean-11-oxo-olean-12-en-28-oic acid-28-O-β--
glucopyranoside)
T. ivorensis Bark [65]
142 Bellericoside
(2α,3β,23,24-tetrahydroxyolean-12-en-28-oic acid-28-O-β--glucopyranoside)
T. chebula
T. bellerica
Stem bark (MeOH)
Stem bark (MeOH)
[123]
[115]
143 Bellericaside (A)
(2α,3β,7α,23-tetrahydroxyolean-12-en-28-oic acid-28-O-β--glucopyranoside) T. bellerica Stem bark [118]
144 Bellericaside (B)
(2α,3β,19α,23,24-pentahydroxyolean-12-en-28-oic acid-28-O-β--galactopyranoside) T. bellerica Stem bark [118]
145 2α,19α-dihydroxy-3-oxo-olean-12-en-28-oic acid-28-O-β--glucopyranoside T.arjuna Roots [101]
146 1α,3β,23-trihydroxy-olean-12-en-29-oic acid-23-O-α-L-4-acetylrhamnopyranoside T. stulhamanii Stem bark (CH2Cl2) [132]
147 1α,3β,23-trihydroxy-olean-12-en-29-oic acid-23-O-α-L-(4-acetylrhamnopyranosyl)-29-
α-rhamnopyranoside T. stulhamanii Stem bark (CH2Cl2) [132]
148 16,17-dihydroneridienone-3-O-β--glucopyranosyl-(1→6)-O-β--galactopyranoside T.arjuna Roots [133]
149 Daucosterol
(β-sitosterol-3-O-β--glucopyranoside)
T. catappa
T. arjuna
T. bellerica
Fruits, leaves (EtOH)
Leaves (MeOH)
Fruits (MeOH)
[98]
[102]
[5]
Table 4. Triterpenes and triterpenoidal glycosides and their occurrence within Terminalia species.
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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Figure 4A: Chemical structures of triterpenes isolated from different Terminalia species.
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 15 of 21
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Figure 4B: Chemical structures of triterpenoidal glycosides isolated from different Terminalia species.
Hepato and nephro-protective activities
T. muelleri polyphenolic-rich fraction possessed hepato
and nephro-protective activities in CCl4-induced hepato- and
nephrotoxicities in mice [29]. e ethanolic bark extract of T.
paniculata possessed hepatoprotective activity and reduced the elevated
serum biochemical parameters and lipid peroxides in paracetamol-
induced liver damage in rats [30]. Also, oral administration of T.
arjuna fruit extract inhibited the hepatic damage and oxidative stress
in cadmium-induced hepatotoxicity in rats [31]. In addition, Manna
demonstrated the protective role of arjunolic acid, isolated from the
bark of T. a r j una, against sodium arsenite-induced oxidative stress in
mouse hepatocytes [32]. In vitro treatment of hepatocytes with chebulic
acid and neochebulic acid, isolated from T. chebula ethanolic fruit
extract, signicantly reduced the tert-butyl hydroperoxide-induced
cell cytotoxicity, reactive oxygen species level, and increased the
hepatic GSH [33]. Corilagin, isolated from T. catappa protected against
galactosamine and lipopolysaccharide-induced hepatotoxicity in rats
at a dose of 1 mg/kg by decreasing the oxidative stress and apoptosis
[34]. Also, pre-treatment with T. bellerica leaf extract in CCl4-induced
hepato- and nephrotoxicities, exhibited a dose-dependent recovery in
all the biochemical parameters, while gallic acid from its extract had a
more pronounced eect at a dose of 200 mg/kg [35].
Anti-inammatory activity
e ethanolic extract of T. phanerophlebia stem as well as its isolated
compound β-sitosterol selectively inhibited cyclooxygenase enzyme
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
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(COX-2) [36]. e aqueous extract of T. paniculata bark signicantly
reduced the edema volume in carrageenan-induced rat paw edema
[37]. Furthermore, the extract at a dose of 400 mg/kg also reduced
the carrageenan-induced leukocyte migration and myeloperoxidase
activity in air pouch exudates and exhibited anti-rheumatic and
analgesic activities at a dose of 200 mg/kg. T. ferdinandiana fruit had
a unique anti-inammatory activities in lipopolysaccharide-activated
murine macrophages, by inhibiting the expression of COX-2 and
inducible nitric oxide synthase (iNOS), as well as by inhibiting the
production of prostaglandin E2 [38].
Chebulagic acid from T. c h ebul a seeds, signicantly suppressed
the onset and progression of collagen-induced arthritis in mice [39].
Moreover, anolignan B isolated from the ethyl acetate root extract of
T. sericea possessed an inhibitory activity against both COX-1 and
COX-2 enzymes [40]. Punicalagin at a dose of 10 mg/kg and punicalin
at a dose of 5 mg/kg isolated from the leaves of T. cat a ppa possessed
an anti-inammatory activity against carrageenan-induced hind paw
edema in rats [41]. Ursolic acid and 2α,3β,23-trihydroxyurs-12-en-28-
oic acid isolated from T. c ata ppa leaf ethanolic extract were responsible
for its anti-inammatory activity, as it caused a signicant reduction
(over 50%) of the edema induced in mice ear at 0.30 mg/ear dose [42].
Gastroprotective activity
Chebulinic acid isolated from T. cheb u l a fruit showed a gastro
protective eect against ulcers induced by cold restraint (62.90%
gastro protection), aspirin (55.30%), alcohol (80.67%) and pyloric
ligation (66.63%) induced ulcer models. Chebulinic acid signicantly
reduced free acidity (48.82%), total acidity (38.29%) and upregulated
mucin secretion (by 59.75%). Additionally, chebulinic acid signicantly
inhibited H+ K+-ATPase activity in vitro with an IC50 value of 65.01
μg/ml compared to that of Omeprazole 30.24 μg/ml, proving its anti-
secretory activity [43]. In addition, the methanolic extract of T. ar jun a
caused a signicant reduction in the lesion index in diclofenac-induced
ulcer, and a signicant increase in pH, non-protein sulydryls, reduced
glutathione, protein bound carbohydrate complexes, adherent mucus
content with a signicant decrease in the volume of gastric juice, free
and total acidity, pepsin concentration, acid output, lipid peroxidase
levels and myeloperoxidase activities [44]. e ethanolic extract of T.
pallida exhibited a signicant anti-ulcer activity against indomethacin,
histamine and ethanol in Swiss albino rats by enhancing the antioxidant
state of the gastric mucosa, thereby reducing mucosal damage [45].
Antimicrobial and Antiviral activity
Various Terminalia species were reported to exert a potent
antimicrobial eect on dierent microorganism. T. ch e bula water
extract had a signicant antibacterial activity on Helicobactor pylori with
MIC and MBC of 125 and 150 μg/ml respectively [46]. Additionally, the
acetone extract of T. c h ebul a exhibited a potent antibacterial activity
on Enterococcus faecalis, Bacillus sabtilis and Klebsiella pneumoniae
bacterias [47]. Casuarinin isolated from the bark of T. a r juna, showed
a strong antiviral activity on Herpes simplex type 2 at a concentration
of 25 μM and reduced the viral titers up to 100,000-fold by inhibiting
the viral attachment and penetration [48]. Recently, Fyhrquist reported
that the methanolic root and stem bark extracts of T. sambesiaca
showed lower MIC values than its aqueous, butanol and chloroform
fractions against mycobacterium [49]. e strong antibacterial activity
of T. muelleri ethylacetate leaf extract was attributed to its gallic acid
content [50].
e antifungal activity of dierent leaf extracts prepared from six
Terminalia species (T. prunioides, T. brachystemma, T. sericea, T. gazensis,
T. mollis and T. sambesiaca) were examined against numerous fungi. It
was found that the acetone extracts possessed the highest antifungal
activity. T. sericea extracts were the most active against nearly all tested
microorganisms [51]. Another study revealed that anolignan B isolated
No. Compound Species Part used (Type of extract) Reference (s)
150 Isoguaiacin T. argentea Bark (EtOH) [107]
151 Termilignan T. bellerica Fruits [108]
152 Thannilignan T. bellerica Fruits [108]
153 Anolignan (B) T. bellerica
T. sericea
Fruits
Roots (EtOAc)
[108]
[40]
154 4-hydroxy-4-methoxy-7,7-epoxylignan T. superba Stem bark (CH2Cl2: MeOH) [18]
155 4,4-dimethoxy-7,7-epoxylignan T. superba Stem bark (CH2Cl3: MeOH) [18]
Table 5. Lignan and lignan derivatives and their occurrence within Terminalia species.
Figure 5: Chemical structures of lignans isolated from different Terminalia species.
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 17 of 21
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
from the ethyl acetate root extract of T. sericea had a strong antimicrobial
activity with MIC values ranging from 3.80 μg/ml against Bacillus
sabtilis to 31 μg/ml against Escherichia coli [40]. Gallic acid isolated
from the methanolic extract of T. nigrovenulosa bark showed a high
antifungal activity against Fusarium solani [52]. Ethanolic root extract of
T. macroptera had a signicant antimicrobial activity, where the lowest
MICs were obtained for Shigella dysenteriae, Staphylococcus aureus and
Vibrio cholera with a signicant activity against Campylobacter species
[53]. Also, the leaf extract of T. macroptera showed an antimicrobial
activity against Neisseria gonorrhoeae with an MIC value between 100
and 200 μg/ml, the diethyl ether fraction was the most active fraction
with an MIC values between 25 and 50 μg/ml [54]. Moreover, it was
assumed that punicalagin and terchebulin, the major compounds of
the T. macroptera root extract were responsible for the in vitro activity
of the extract against Helicobacter pylori [55]. e methanolic extract
of T. superba stem bark, together with its major component 3’,4-di-O-
methyl-3-O-(β--xylopyranosyl) ellagic acid prevented the growth of
various mycobacteria and fungal species [56]. Punicalagin, isolated
from the acetone extract of T. brachystemma leaves, displayed a good
antifungal activity against Candida parapsilosis (MIC=6.25 µg/ml),
Candida krusei (MIC=6.25 µg/ml) and Candida albicans (MIC=12.50
µg/ml) [9]. T. australis methanol and aqueous extracts were eective
against the several Aspergillus and Candida strains [57]. e compounds
5,7,2-tri-O-methyl-avanone-4-O-α-L-rhamnopyranosyl-(1→4)-β--
glucopyranoside and 2α,3β,19β,23-tetrahydroxyolean-12-en-28-oic-
acid-3-O-β--galactopyranosyl-(1→3)-β--glucopyranoside-28-O-β-
-glucopyranoside isolated from the roots of T. al a t a were reported to
have a strong antifungal activity [58].
Cytotoxic activity
T. ch e bula methanolic fruit extract showed a reduction in cell
viability, inhibition of cell proliferation, and induction of cell death in
a dose-dependent manner on many malignant cell lines. In addition,
it induced apoptosis at lower concentrations, and necrosis at higher
concentrations. Chebulinic acid, tannic acid and ellagic acid, with
IC50 values of 53.20, 59.00 and 78.50 µg/ml respectively, were the most
cytotoxic compounds of T. che b ula fruit [59]. Furthermore, chebulagic
acid isolated from the T. c hebu l a fruit extract possessed an anti-
proliferative activity against HCT-15, COLO-205, MDA-MB-231, DU-
145 and K562 cell lines [60]. T. catappa leaf water extract, along with
its isolated component punicalagin were eective against bleomycin-
induced genotoxicity in Chinese hamster ovary cells [61]. Furthermore,
T. ca t appa leaf extract exerted a dose-dependent inhibitory eect on
the invasion and motility of highly metastatic A549 and Lewis lung
carcinoma cells [62]. Moreover, the ethanol extract of T. c ata p pa leaves
signicantly inhibited the cell migration capacity of oral squamous cell
carcinoma cells [63]. Luteolin, gallic acid and gallic acid ethyl ester
isolated from the bark, stem and leaves of T. arjuna methanolic extract
possessed a strong antineoplastic activity [64]. Moreover, ivorenoside
C isolated from the bark of T. ivorensis had an antiproliferative activity
against MDA-MB-231 and HCT116 human cancer cell lines with IC50
values of 3.96 and 3.43 μM respectively [65]. Additionally, the acetone
extract of T. calamansanai leaves inhibited the viability of HL-60 cells
[66].
Cardioprotective activity
T. arjuna bark has been used widely in traditional medicine as a
cardioprotective. e ethanolic extract of T. arjuna bark enhanced the
cardiac intracellular antioxidant status in CCl4-induced oxidative stress
in rats [67]. e protective eect was comparable to that of vitamin C.
In addition, e butanol fraction of T. arju n a bark extract exhibited
a protective eect against doxorubicin-induced cardiotoxicity by
increasing cardiac antioxidant enzymes, decreasing serum creatine
kinase-MB levels and reducing lipid peroxidation [68]. Many clinical
trials were also conducted to prove the benecial eect of T. arju na bark
on the heart. A group of scientists showed that patients with refractory
chronic congestive heart failure, when received T. a r j una bark extract
as an adjuvant therapy, showed a long lasting improvement in the signs
and symptoms of heart failure with an improvement in le ventricular
ejection phase indices and quality of life [69]. Moreover, a clinical
study was done to evaluate the role of T. ar ju n a in ischemic mitral
regurgitation (IMR) following acute myocardial infarction. Patients
receiving adjuvant T. ar ju n a showed signicant decrease in IMR and
reduction in anginal frequency [70]. In addition, pretreatment with T.
pallida fruit extract ameliorated myocardial injury in isoproterenol-
induced myocardial infarction in rats and exhibited cardioprotective
activity [71]. Similarly, pretreatment with T. cheb ul a extract ameliorated
the eect of isoproterenol on lipid peroxide formation [72].
Anti-hypertensive activity
T. superba bark extract showed a potent antihypertensive activity
in spontaneously hypertensive rats, as well as in glucose-induced
hypertensive rats due to the withdrawal of sympathetic tone and the
improvement of the antioxidant status [73,74].
Antiparasitic and molluscicidal activity
e in vitro nematicidal activity of T. nigrovenulosa bark against
Meloidogyne incognita was attributed to 3,4-dihydroxybenzoic acid
isolated from it. [75]. e ethyl acetate, acetone and methanol leaf
and seed extracts of T. ch e bula showed in vitro ovicidal and larvicidal
activities on Haemonchus contortus [76]. In addition, T. ch e b ula fruit
molluscicidal activity was due its tannic acid content that signicantly
inhibited the AChE, ACP and ALP activity in the nervous tissue of
freshwater snail Lymnaea acuminate [77]. Additionally, ethanolic leaf
extract of T. ca t appa possessed a molluscicidal activity against the
snail intermediate hosts of schistosomiasis (Biomphalaria pfeieri and
Bulinus globosus) with B. pfeieri being more susceptible [78].
Wound healing activity
Topical administration of T. chebula alcoholic leaf extract on the
rat dermal wounds showed a benecial eect in the acceleration of the
healing process, by increasing the tensile strength of tissues by about
40% and decreasing the period of epithelialization [79]. Moreover, the
tannin-rich fraction obtained from T. chebula fruits endorsed wound
healing in rats due to the powerful antibacterial and angiogenic activity
of the extract [80]. Topical application of T. arjuna hydro-alcholic
extract resulted in a signicant increase in the tensile strength of the
incision wounds and epithelialization of excision wounds. is wound
healing property was more pronounced in the tannin-rich fraction
compared to the other fractions [81].
Conclusion
An extensive literature survey on genus Terminalia has revealed
a variety of chemical constituents produced by this genus. Tannins,
avonoids, phenolic acids, triterpenes, triterpenoidal glycosides, lignan
and lignan derivatives constitute the major classes of phytoconstituents
of this genus [82-105]. In addition, the current review showed that most
of the biological studies performed on dierent extracts and isolated
compounds from dierent species of Terminalia were focused on the
assessment of the antimicrobial, antioxidant, hepatoprotective, anti-
Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
Page 18 of 21
Volume 4 • Issue 5 • 1000218
Med Aromat Plants
ISSN: 2167-0412 MAP, an open access journal
inammatory, hypoglycemic, hypolipidimic, cytotoxic and wound
healing activities of these species. e various pharmacological studies
validated the folk medicinal uses of dierent Terminalia species.
Although many phytochemical and biological investigations were
reported from the genus Terminalia, the studies have focused mainly
on certain species, with chebula, bellerica, arjuna, catappa, horrida,
superba, macroptera, pallida, ivorensis, sericea and alata being the most
phytochemically and biologically studied species, leaving a fertile area
for further investigations on other species that have not been fully
explored yet [106-133]. e present review provides a comprehensive
understanding of the chemistry and biology of dierent Terminalia
species, which may help in the discovery and development of new
alternative medications for the treatment of various diseases and health
problems.
Declaration of Interest
The authors have declared no conicts of interest.
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Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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ISSN: 2167-0412 MAP, an open access journal
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Citation: Fahmy NM, Al-Sayed E, Singab AN (2015) Genus Terminalia: A phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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ISSN: 2167-0412 MAP, an open access journal
131. Ali A, Ali M, Alam MS (2006) Two new oleanane triterpene glycosides from the
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phytochemical and Biological Review. (Montin.) Species. Med Aromat Plants
4: 218. doi:10.4172/2167-0412.1000218
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... Lillo, T. stenostrachya Engl.& Diels have been reported to have flavonoids, ellagitannins, stilbenes, glycosides, and phenolic compounds (Beigi et al., 2018;Cock, 2015;Fahmy et al., 2015) with different biological activities. Sclerocarya birrea (A.Rich) Hochst (also known as Morula in Botswana), is a savanna tree that belongs to the Anacardiaceous family. ...
... TPPE methanol extracts showed high concentrations of saponins, flavonoids and phenols, and mild concentrations of tannins, steroids and terpenoids. Saponins, tannins, flavonoids, phenols, terpenoids, cardiac glycoside and steroids have been reported by (Beigi et al., 2018;Cock, 2015;Fahmy et al., 2015) in other species of genus Terminalia. The observed folk pharmacological activities of various parts of Sclerocarya birrea and Terminalia prunioides may be due to the presence of flavonoids and phenols at mild and high quantities (Fahmy et al., 2015;Russo et al., 2018). ...
... Saponins, tannins, flavonoids, phenols, terpenoids, cardiac glycoside and steroids have been reported by (Beigi et al., 2018;Cock, 2015;Fahmy et al., 2015) in other species of genus Terminalia. The observed folk pharmacological activities of various parts of Sclerocarya birrea and Terminalia prunioides may be due to the presence of flavonoids and phenols at mild and high quantities (Fahmy et al., 2015;Russo et al., 2018). Seventeen compounds were identified/quantified by HPLC and 24 by LC-ESI-MS/MS, summing to a total of 33 different polyphenolic compounds. ...
Article
Cancer is one of the leading causes of death globally. Conventional drugs are expensive and have been reported to have side effects. This directs efforts in cancer research to search for inexpensive solutions with less or no side effects. This study aimed at screening for phytochemicals and the antiproliferative effects of Sclerocarya birrea fruit exocarp (SBFE) and Terminalia prunioides pods extracts (TPPE) on human cervical cancer cell line (HeLa). Extracts were qualitatively evaluated for their phytochemicals using HPLC and LC-MS/ MS, and the antiproliferative effects by 4-[-3(4-Iodophenyl)-2-(4-nitro-phenyl)-2H-5-tetrazolio]-1,3-ben-zene sulfonate (WST-1) assay. HPLC and LC-MS/MS analysis led to identification and quantification of 24 polyphenolic metabolites amongst which shikimic acid (3.6014 mg g-1), gallic acid (40.8283 mg g-1), and quercetin-3-d-xyloside (3.4677 mg g-1) as the major metabolites. Results from antiproliferative effects of extracts were used to make 3 potential anticancer formulations. Furthermore, effects of extracts and formulations on the expressions of cervical cancer markers: Epidermal Growth Factor Receptor (EGFR), Metastasis-Associated in Colon Cancer 1 (MACC1), Vascular Endothelial Growth Factor (VEGF), Cytokeratin Fragment (CYFRA 21-1), and Cluster differentiation 95 (CD95) were evaluated by Reverse transcription quantitative Polymerase Chain Reaction (RT-qPCR). Methanol and ethyl acetate extracts of both plants tested positive for saponins, tannins, flavonoids, phenols, terpenoids, cardiac glycoside and steroids. Methanol extracts were the most effective with IC 50 values of 75 mg/mL and 190 mg/mL for SBFE and TPPE respectively. The formulations: M1E1M2E2 and M1M2 had IC 50 values of 77 mg/mL and 83 mg/mL respectively. All treatments down-regulated mRNA expression of EGFR, VEGF, MACC1, CYFRA 21-1, and upregulated CD 95 mRNA expression. Formulations were more effective than individual extracts against HeLa cells. However, there is need for further testing for other possible mechanisms of action and isolation of phytocompounds.
... (20,21). The Terminalia elliptica plant, also called Asna, exhibits various medicinal properties such as anti-microbial, anti-inflammatory, anti-cancer, anti-diabetic, anti-aging, hepato-protective, antioxidant, and neuroprotective activities ( Figure 3) (22)(23)(24). This evidence suggests we investigate the potential anti-cancer activity of Terminalia Elliptica. ...
Article
Full-text available
Cancer remains a significant global health challenge, prompting exploration into alternative treatments such as those derived from natural compounds found in traditional medicine. Recent research has underscored the role of proteins like Focal Adhesion Kinase (FAK), Vascular Endothelial Growth Factor (VEGF), and Metastasis-Associated Protein 1 (MTA1) in driving cancer cell proliferation and survival. Here, we investigated the potential of a single molecule to modulate these key proteins involved in metastasis, offering a promising avenue for cancer therapy. Terminalia elliptica, commonly known as Asna, possesses a diverse range of medicinal properties, including antimicrobial, anti-inflammatory, anticancer, antidiabetic, antiaging, hepatoprotective, antioxidant, and neuroprotective activities. Our study aimed to explore the anticancer potential of Terminalia elliptica by identifying bioactive compounds capable of targeting FAK, VEGF, and MTA1 to impede cancer metastasis. Through in silico analysis, we conducted network analysis using Cytoscape to assess the significance of these bioactive compounds in the inhibition of signaling pathways driving metastasis. The utilization of these bioactives as potential candidates for targeted therapy of VEGF, FAK, and MTA1 regulated pathways was preliminarily assessed by Molecular Docking and MD Simulation. Our findings revealed that phytobioactives namely, Chebulinic Acid of Terminalia elliptica, exhibited notable binding affinity and interaction with FAK, and Chebulagic Acid with VEGF, and MTA1. This discovery holds promise as a novel therapeutic approach for combating cancer, offering potential benefits in cancer treatment and management.
... While the phytochemical constituents of the Terminalia plant species have been extensively reviewed Cock, 2015;Zhang et al., 2019;Cock and Cheesman, 2021), limited data exists on the compounds present in TP and TS other than a few sterol and steroid compounds (Fahmy et al., 2015). As such, metabolomics analysis of the methanolic and aqueous TP and TS leaf extracts were conducted in the present study, which identified several compounds known to possess antibacterial activity (Table 7; Fig. 2). ...
Article
Full-text available
Plants of the genus Terminalia are used in multiple traditional medicine systems globally, including in southern Africa. Whilst scientific studies have confirmed the therapeutic properties of some Terminalia species, other species remain relatively overlooked. This study examines the antibacterial properties of Terminalia phanerophlebia Engl. & Diels (TP) and Terminalia sambesiaca Engl. & Diels (TS) leaf extracts, and their ability to potentiate selected conventional antibiotics against antibiotic-sensitive and antibiotic-resistant pathogens. The antibacterial activities of the extracts and reference antibiotics were screened using disc diffusion assays and quantified using liquid microdilution MIC assays. The methanolic and aqueous TP and TS leaf extracts inhibited the growth of S. aureus, E. coli and K. pneumoniae, including MRSA and ESBL antibiotic-resistant strains, producing zones of inhibition on agar of 13À15 mm, and minimum inhibitory concentration values of 182À1500 mg/mL in most cases. Notably, the extracts inhibited MRSA growth with a similar efficacy to that observed against the susceptible S. aureus strain (133À265 mg/mL). Combining the extracts with tet-racycline and chloramphenicol had substantially greater antibacterial activity than for either component alone, indicating that extract components block bacterial resistance mechanisms. In contrast, the extracts antagonised the activity of ciprofloxacin against some of the bacterial species. Extract toxicities were assessed using Artemia nauplii toxicity bioassays and were all found to be nontoxic. Additionally, Orbitrap LC-MS was used to identify and highlight noteworthy compounds in the extracts. Non-targeted LC-MS analysis revealed the presence of several noteworthy compounds, including tannins and flavonoids. Our findings suggest that the TP and TS extracts show promise for antibacterial drug development. Further study is warranted to elucidate their antibacterial and potentiating mechanisms.
... "Terminalia catappa, also known as a tropical plant widely recognized by its common name; the indian almond or tropical almond plant. It is the second-largest genus of the family Combretaceae" [9]. "It is a well-known plant recognized for its edible parts including fruit, bark, leaves, and roots. ...
Article
Full-text available
Context: Terminalia catappa, also known as tropical almond, is a well-known plant recognized for its edible parts, including fruit, bark, leaves, and roots. It is also noted for its medicinal usefulness and numerous pharmacological actions. Aim: This study aims to analyze the proximate composition of the seeds of tropical almonds, extract and characterize the oil from Terminalia catappa seeds and mesocarp. The goal is to assess the nutritional value of Terminalia catappa and to evaluate the oil's physicochemical properties. Materials and Methods: Standard methods were used to assess physicochemical parameters such as saponification, acid, peroxide, iodine, and specific gravity. The seed's proximate composition was also analyzed, revealing moisture, ash, crude fiber, fat, protein, and carbohydrate content. Results: The results indicate that the saponification value (mg KOH/g), acid value (mg KOH/g), iodine value (mg iodine/mg), peroxide value (mg/peroxide/kg), and specific gravity of the oil are 162, 1.68, 89, 1.40, and 0.95 respectively. The proximate composition reveals that the seed contains 23.24% moisture, 5.50% ash, 12.30% crude fiber, 16.51% fat, 21.22% protein, and 39.99% carbohydrate. These findings suggest that tropical almond seed is a good source of protein, carbohydrates, and oil and contains minerals that can contribute valuable amounts of essential nutrients to the human diet. The low acid value suggests that the oil is edible, while the high saponification value indicates its potential in industrial applications such as cosmetics. The low iodine value reveals that it is a non-drying oil unsuitable for the paint industry. Additionally, the low peroxide value of the oil indicates low susceptibility to oxidative rancidity and deterioration, confirming the presence of antioxidants in the seed oil. Conclusion: Terminalia catappa seeds exhibit a high level of most chemical components, making them a promising raw material for various industries. Their high protein value and low level of anti-nutrients indicate their potential usefulness in animal and poultry feed supplements. They also serve as beneficial dietary supplements and should be encouraged in diets.
... The seed is not exploited commercially. Their approximate analysis revealed a high content of proteins and lipids (whose composition is predominantly oleic (C18:1) and linoleic (C18:2) unsaturated acids, in addition to carbohydrates and minerals [4,6,[8][9][10][11]). C. aphrodisiac activity and moderate consumption are useful in the treatment of sexual dysfunction among men, especially for premature ejaculation [12]. ...
Article
The Terminalia catappa L. tree is an ornamental and shade tree producter of a large amount of biological waste sent to landfills. Therefore, this plant constitutes so-called municipal solid wood waste (MSWW), which causes undesirable impacts on the environment, such as the generation of methane through the action of microorganisms. Sustainable solutions for the proper use and disposal of MSWW are a topic that has assumed great relevance at present due to the high quantities of MSWW generated worldwide. Pyrolysis constitutes an attractive alternative for the sustainable use of MSWW to produce higher value-added products. This study investigated the slow pyrolysis of Terminalia catappa L. fruit and the use of the aqueous fraction produced for bovine mastitis control. We obtained four fractions from the pyrolysis process, with average yields of the aqueous phase (36.22 ± 2.0 %), bio-oil (5.52 ± 0.4 %), biochar (37.55 ± 2.8 %) and gas (20.71 ± 2.0 %). The aqueous fraction was extracted with organic solvents and analyzed by gas chromatography coupled to mass spectrometry (GC-MS). The extracts were composed mainly of phenols (50 %), furan derivatives, cyclic ketones, and others with lower contents, such as alcohols and esters. The aqueous fraction had bactericidal activity against Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli, which are responsible for bovine mastitis. In addition, the fraction showed low cytotoxicity against a murine melanoma cell line from a C57BL/6J mouse, B16F10 cells and mouse peritoneal cells.
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