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Combretum quadrangulare (Combretaceae): Phytochemical Constituents and

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 Indo American Journal of Pharmaceutical Research, 2014 ISSN NO: 2231-6876

INDO AMERICAN
Journal home page: JOURNAL OF
http://www.iajpr.com PHARMACEUTICAL
RESEARCH

Combretum quadrangulare (Combretaceae): Phytochemical Constituents and Biological

activity
Rajiv Roy1, Raj K. Singh2, Shyamal K. Jash3, Atasi Sarkar4 and Dilip Gorai1*
1
Department of Chemistry, Kulti College, Kulti, Burdwan-713 343, West Bengal, India
2
Department of Botany, Jhargram Raj College, Jhargram, Paschim Medinipur-721507, West Bengal, India
3
Department of Chemistry, Saldiha College, Saldiha, Bankura-722173, West Bengal, India
4
Department of Zoology, Kapastikuri S.S.K. Vidyapeeth, Sitapur-731235, Birbhum, West Bengal, India

ARTICLE INFO ABSTRACT

Article history The present work offers a review addressing the chemistry and pharmacology of Combretum
Received 05/08/2014 quadrangulare (belonging to Combretaceae family) regarded as one of the most significant
Available online plant species in traditional system of medicine and is established as a source of terpenoids,
31/08/2014 flavonoids, steroids etc. The isolated phytochemicals as well as different extracts exhibited
significant biological activities such as antimicrobial, anti-HIV, cytotoxic and
hepatoprotective activities. Exhaustive research regarding isolation of more phytochemicals
Keywords and pharmacology study on this medicinal plant is still necessary for the exploration the plant
Combretum quadrangulare, regarding its medicinal importance. Therefore, the aim of this review is to boost up present
Combretaceae, day researchers in this direction to undertake further investigation of this plant for searching
Phytochemical constituents, new phytochemicals for the development of new drugs. The present review covers literature
Biological activity. up to June 2014 and enlists 23 references.

Corresponding author
Dr. Dilip Gorai
Address: Department of Chemistry,
Kulti College, Kulti, Burdwan, West Bengal, India,
PIN-713 343,
E-mail: dilipgorai1976@gmail.co.in/Dgorai2005@yahoo.co.in

Please cite this article in press as Dilip Gorai et al. Combretum quadrangulare (Combretaceae): Phytochemical Constituents and
3416

Biological activity. Indo American Journal of Pharmaceutical Research.2014:4(08).

Copy right © 2014 This is an Open Access article distributed under the terms of the Indo American journal of Pharmaceutical
Research, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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INTRODUCTION
The Combretaceae family consists of as many as 600 species of trees, shrubs and lianas in about 18-20 genera.
Plants belonging to this family are found in tropical and sub- tropical regions, mostly in Africa and India. The largest genera are
Combretum and Terminalia, with about 370 and 200 species, respectively [1]. Combretum quadrangulare is the most investigated
species of this genus.
Combretum quadrangulare is a shrub or tree, indigenous to Southeast Asia, especially Burma to Laos. The plant is
commonly known as “tram bau” (Vietnam), “ke khao” (Laos) or “sang kae” (Cambodia). The tree grows wildly or is planted in
Vietnam, Cambodia, Laos, Myanmar and Thailand. The tree is planted along the banks of rivers or arroyos for firing. It is found
throughout Thailand especially in open, wet places. Height of tree is 5-10 meters, having young branchlets acutely quadrangular or
very narrowly quadrialate. Leaves are simple, opposite, elliptic or obovate, which are 3-8 cm wide and 6-16 cm long: petiole acutely
ridged. Inflorescence in terminal and axillary spike; flowers are small having yellowish white colour. Fruit are dry, thinly quadrialate:
seed brownish red, ellipsoid, 4-angled [2]. Various terpenoids and flavonoids constituents have been isolated from this plant and some
significant biological activities are reported by different plant parts, crude extracts as well as isolated phytochemicals. Therefore, the
aim of this review article is to stimulate present day researcher to undertake more systematic research work on this important
medicinal plant so as to isolate more phytochemicals and to discover other significant biological activities of the plant.

Taxonomical background
The taxonomical classification of the plant is presented below:

Kingdom Plantae
Order Myrtales
Family Combretaceae
Genus Combretum
Species C. quadrangulare

Medicinal use
The plant is reported to have traditional use as medicine. Its seeds, leaves, and the stem bark are used in Vietnamese
traditional medicine as an antipyretic, antidysenteric, and anthelmintic agent. The seeds are administered orally together with ripe
bananas as an anthelmintic for ascariasis and oxyuriasis. [3]

MATERIALS AND METHODS

The chemical constituents isolated and identified from Combretum quadrangulare, pharmacological activities exhibited by
the isolated compounds as well as by the crude plant extracts were searched across the Medline (National Library of Medicine) and
Science Direct databases. The data were updated in June 2014, using the search terms Combretum quadrangulare, chemical
constituents, biological activities, pharmacological activities or properties of Combretum quadrangulare as keywords. In addition, the
reference lists of all papers identified were thoroughly reviewed.

RESULTS AND DISCUSSION

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Phytochemical constituents isolated from Combretum quadrangulare

Chemical constituents isolated so far from this plant are presented in Table 1. Most of the isolated compounds belong to the class
of triterpenoids and flavonoids. As per literature survey upto June 2014, ninety-seven chemical constituents (Structure No. 1-97,
Table-1) have been isolated so from this plant.
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Table 1: List of phytochemical constituents isolated from C. quadrangulare.

Str.No. Compound Name Reference

Triterpenoids
1 Arjungenin [4]
2 Arjunglucoside I [4]
3 1α,3β-dihydroxy-cycloart-24-ene-30-carboxylic acid [5]
4 1α,3β-dihydroxy-cycloart-24-ene-30-carboxylic acid methyl ester [5]
5 (20ξ)-1α,3β,25-trihydroxy-cycloart-21-al-23-ene-30-carboxylic acid methyl ester [5]
6 Quadrangularic acid F [6]
7 Quadrangularic acid J [6]
8 Quadrangularic acid G [6]
9 Methyl quadrangularate I [6]
10 24-epiquadrangularic acid M [6]
11 24-epiquadrangularic acid G [6]
12 Quadrangularic acid M [6]
13 Quadrangularic acid H [6]
14 Quadrangularic acid K [6]
15 Quadrangularic acid L [6]
16 24-epiquadrangularic acid L [6]
17 7β-hydroxy-23-deoxojessic acid [6]
18 Norquadrangularic acid A [6]
19 Methyl quadrangularate A [7]
20 Methyl quadrangularate B [7,8]
21 Methyl quadrangularate C [7]
22 Methyl 24-epiquadrangularate C [7]
23 Methyl quadrangularate O [7]
24 Methyl quadrangularate D [7,8]
25 Quadragularol A [7]
26 Methyl quadrangularate N [7]
27 Quadragularol B [7]
28 Quadrangularic acid E [7]
29 23-Deoxojessic acid [7]
30 1-O-acetyl-23-deoxojessic acid [7]
31 4β,14α-dimethyl-5α-ergosta-9β,19-cyclo-24(31)-en-3β-hydroxy-4α-carboxylic acid [7]
32 Methyl 23-deoxojessate [7]
33 Methyl quadrangularate P [7]
34 Norquadrangularic acid B [7]
35 Norquadrangularic acid C [7]
36 Betulinic Acid [7]
37 2α,6β-dihydroxybetulinic acid [9]
38 6β-hydroxyhovenic acid [9]
39 Quadranoside II [9,10]
40 6β-hydroxyarjunic acid [9]
41 Arjunic acid [9]
42 Arjunolic acid [9,11]
43 Arjunglucoside II [9,11]
44 19α-hydroxyasiatic acid [9,10]
45 Nigaichigoside F1 [9,10]
46 Quadranoside IV [9,10,11]
47 2α,3β,23-trihydroxyurs-12,18-dienoic acid [9]
48 Glucosyl 2α,3β,23-trihydroxyurs-12,18-dien-28-oate [9]
49 Glucosyl 2α,3β,23-trihydroxyurs-12,19(20)-dien-28-oate [9]
50 Quadranoside I [10]
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51 Quadranoside III [10]

52 Quadranoside V [10]
53 2α,3β,23-trihydroxyurs-12,19-dien-28-oic acid β-D-glucopyranosyl [4,10]
54 Pinfaensin [10]
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55 Quadranoside VI [4]
56 Quadranoside VII [4]

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57 Quadranoside VIII [4]

58 Quadranoside IX [4]
59 Rosamutin [4]
60 28-O-β-D-glucopyranosyl-6β,23-dihydroxytormentic acid [4]
61 Quadranoside X [4]
62 Quadranoside XI [4]
63 Arjunetin [4]
64 Chebuloside II [4]
65 β-D-glucopyranosyl-2α,3β,6β-trihydroxyolean-12-en-28-oate [4,11]
66 Ursolic Acid [12]
67 Combretanone A [12]
68 Combretanone B [12]
69 Combretanone C [12]
70 Combretanone D [12]
71 Combretanone E [12]
72 Combretanone F [12]
73 Combretanone G [12]
74 Combretic acid A [12]
75 Combretic acid B [12]
Flavonoids
76 Kamatakenin [7]
77 Isokaempferide [7]
78 5,7,4′-trihydroxy-3,3′-dimethoxyflavone [7]
79 5,4′-dihydroxy-3,7,3′-trimethoxyflavone [7]
80 (+)-catechin [10]
81 (+)-gallocatechin [4]
82 (-)-epicatechin [4]
83 (-)-epigallocatechin [4]
84 Vitexin [10]
85 5,7,3′,5′-tetrahydroxy-3,4′-dimethoxyflavone [12]
86 Combretol [12]
87 3′,5-dihydroxy-3,4′,5′,7-tetramethoxyflavone [12]
88 Pachypodol [12]
89 Quercetin 3,4′-dimethyl ether [12]
90 Myricetin 3,3′,4′-trimethyl ether [12]
Miscellaneous
91 Gallic acid [10]
92 Methyl gallate [10]
93 1-O-Galloyl-6-O-(4-hydroxy-3,5-dimethoxy)benzoyl-β-D-glucose [13]
94 β-sitosterol [7]
95 β-sitosterol glucoside [10]
96 5-methoxy-(-)-isolariciresinol [10]
97 5-methoxy-9β-xylopyranosyl-(-)-isolariciresinol [10]

Biological activity exhibited by the plant and phytochemicals isolated

Crude plant extracts as well as phytochemicals isolated from C. quadrangulare exhibited various biological activities as
discussed below:

Antibacterial activity
Crude methanolic extracts of C. quadrangulare seeds showed antibacterial activity against gram-positive cocci, methicillin-
sensitive S. aureus (MSSA) and methicillin-resistant S. aureus (MRSA) having MIC values of 1212 μg/mL and 606.25 μg/mL,
respectively [14]. The extract was also found to be active against non-fermentative gram-negative bacteria P. aeruginosa ATCC
27853 and Acinetobacter baumanii, having MIC value 2425 μg/mL and 2425 μg/mL, respectively and fermentative gram-negative
bacilli E. coli having MIC value 9,700 μg/mL [14]. Somanabandhu et al. revealed t h a t ether and ethanolic extracts of dried root
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bark or dried seeds of the plant are effective against earthworms when tested in vitro [15]. D r i e d l e a f e x t r a c t o f t h e p l a n t
wa s r e p o r t e d t o s h o w a ntimicrobial activity against Helicobacter pylori [16]. Acetone, MeOH, and aqueous extracts of C.
quadrangulare were tested for their trypanocidal activity against epimastigotes of Trypanosoma cruzi, the causative agent of
Chagas disease; acetone extract being the most active [17].
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Anti-HIV Activity
The aqueous and EtOH extracts of C. quadrangulare were screened for their inhibitory activity against HIV-1 integrase
(IN) - an enzyme essential for viral replication. The investigators noted significant inhibitory activity against the tested enzyme for
both the aqueous and EtOH extract having IC50 values of 2.5 and 2.9 µg/mL, respectively [18].

Cytotoxic Activity
Cycloartane tritererpenoids and flavonoids isolated from the MeOH extract of leaves were subjected to cytotoxic activity
against highly liver metastatic murine colon 26-L5 carcinoma cells [7]. Methyl quadrangutarate B (20) and D (24) out of the tested
terpenoids exhibited strong cytotoxicity having ED50 values of 9.54 and 5.42 µM, respectively, whereas all the flavonoids (76-79)
showed the strong cytotoxicity having ED50 values less than 6 µM (Table-2)[7].

Table 2: Cytotoxic activity of the constituents isolated from C. quadrangulare

Compounds ED50 value Compound ED50 value Compound ED50 value

(µM) (µM) (µM)
19 43.8 27 17.6 32 65.7
20 9.5 28 58.6 34 65.9
21 18.9 78 5.2 36 59.7
23 52.6 79 4.5 76 3.0
24 5.4 29 49.6 77 1.8
25 49.7 30 57.7
26 61.4 31 62.4

Hepatoprotective activity
Many plants are reported to exhibit hepatoprotective activity [19-21]. The hepatoprotective effect of MeOH, MeOH/H2O
(1:1) and aqueous extracts of C. quadrangulare seeds were examined on D-galactosamine (D-GalN)/tumor necrosis factor-α
(TNF-α)-induced cell death in primary cultured mouse hepatocytes [22]. The MeOH extract n o t o n l y showed the strongest
inhibitory effect on D-GalN/TNF-α-induced cell death (IC50 56.4 μg/mL) but also significantly lowered the serum GPT level in
mice with D-GalN/lipopolysaccharide (LPS)-induced liver injury [22].
Bio-guided separation of the MeOH extract led to the isolation of various classes of compound including triterpcne
glucosides, lignans and catechin derivatives. Among the isolated triterpene glucosides, lupane-type Quadranoside II (39),
Quadranoside I (50) and Quadranoside XI (62) exhibited hepatoprotective efficacy against n-GalN/TNF-α-induced cell death in
primary cultured mouse hepatocytes having IC50 values of 63.1, 59.8 and 76.2 μM, respectively whereas ursane-type Quadranoside V
(52), mixture of Glucosyl 2α,3β,23-trihydroxyurs-12,19(20)-dien-28-oate (49) and Glucosyl 2α,3β,23-trihydroxyurs-12,18-dien-28-
oate acid (48), and β-D-glucopyranosyl (53) exhibited strong hepatoprotective activity having IC50 values 30.2 and 34.6 μM,
respectively. Other isolated compounds like 1-O-galloyl-6-O-(4-hydroxy-3,5-dimethoxy)benzoyl-β-D-glucose (93), methyl gallate
(92) and (-)-epicatechin (82) were also found to exhibit potent hepatoprotective effect having IC 50 values of 7.2, 19.9 and 71.2 μM,
respectively [22]. The compound 1 - O-galloyl-6-O-(4-hydroxy-3,5-dimethoxy)benzoyl-β-D-glucose (93), a gallic acid derivative
isolated from C. quadrangulare, demonstrated potent hepatoprotective activity against D-GalN/TNF-alpha-induced cell death in
primary cultured mouse hepatocytes with an IC50 of 3.3 μM [13].
The triterpenes of the lupane type, 2α,6β-dihydroxybetulinic acid (37) and 6β-hydroxyhovenic acid (38), isolated from the
MeOH extract of C. quadrangulare seeds, also exhibited strong hepatoprotective activity [9]. Both MeOH and water extracts of the
leaves of Combretum quadrangulare showed hepatoprotective effect dose-dependently with cell survival rates of 88.2±8.8% and
60.0±6.7%, respectively, at 100 μg/mL concentration as compared to control (cell survival rate 43.7±5.7%). This result indicated that
the MeOH extract had stronger hepatoprotective effect than the water extract, which is parallel to that obtained from the in vivo
experiment.
The MeOH extract of leaves of the plant showed significant hepatoprotective effect on D-galactosamine (D-
GalN)/lipopolysaccharide (LPS)-induced experimental liver injury in mice and on D-GalN/tumor necrosis factor-α (TNF-α)-induced
cell death in primary cultured mouse hepatocytes [23]. The compounds isolated from MeOH extract showed various potencies of
hepatoprotective effect on D-GalN/TNF-α-induced cell death in primary cultured mouse hepatocytes. Quadrangularol B (27), methyl
quadrangularate I (9), kamatakenin (76), 5,7,4'-trihydroxy-3,3'-dimethoxyflavone (78), 5,4'-dihydroxy-3,7,3'-trimethoxyflavone (79)
and isokaempferide (77) showed strong inhibitory effect on TNF-α-induced cell death with IC50 values of 34.3, 33.7, 13.3, 22.4, 13.4
and 22.8 μM, respectively whereas clinically-used silibinin had an IC50 value of 39.6 μM while glycyrrhizin showed very weak
inhibitory effect. Methyl quadrangularates A (19) and N (26), norquadrangularic acid B (34) and vitexin (84) also showed potent
3420

inhibition on TNF-α-induced cell death with IC50 values of 45.7, 89.3, 67.6 and 40.1 μM, respectively, however the other isolated
constituents like 4β,14α-dimethyl-5α-ergosta-9β,19-cyclo-24(31)-en-3β-hydroxy-4α-carboxylic acid (31), Methyl quadrangularate
D (24), 24-epiquadrangularic acid M (10), Quadrangularic acid H (13), 24-epiquadrangularic acid L (16), Norquadrangularic acid C
(35) and epimeric mixture of Methyl quadrangularate C (21) and Methyl 24-epiquadrangularate C (22) exhibited weak
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hepatoprotective activity against O-GalN/TNF-α-induced cell death in primary cultured mouse hepatocytes. All these compounds
were found to have stronger hepatoprotective effect than glycyrrhizin [23].

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CONCLUSION
The present article deals with an up-to-date review on the chemistry and pharmacology of Combretum quadrangulare, a
useful medicinal plant from Combretaceae family finding applications in indigenous systems of medicine. Its seeds, leaves, and the
stem bark are used in Vietnamese traditional medicine as an antipyretic, antidysenteric, and anthelmintic agent. The isolated
phytochemicals as well as different extracts exhibited significant biological activities such as antimicrobial, anti-HIV, cytotoxic and
hepatoprotective activities and is established as a source of terpenoids, flavonoids and other phytochemicals. Exhaustive research
regarding isolation of more phytochemicals and pharmacology study on this medicinal plant is still necessary so as to explore the plant
regarding its medicinal importance. Therefore, the aim of this review is to boost up present day researchers in this direction to
undertake further investigations of this plant and we do anticipate that this plant will be much effective in drug development
programme in near future; present day researcher will surely undertake further research work on this medicinal plant for the
betterment of mankind.

ACKNOWLEDGEMENTS
The authors are thankful to the Department of Chemistry, Kulti College and Department of Chemistry, Saldiha College for
providing necessary infrastructural facilities to carry out the review work.

Authors’ Statements
Competing Interests
The authors declare no conflict of interest.

Figure-1: Structure of the chemical constituents isolated from C. quadrangulare.

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