MORPHOLOGICAL, ANATOMICAL PROPERTIES,

CHEMICAL ANALYSIS AND BIOLOGICAL

ACTIVITY OF CAESALPINIA SAPPAN L. (FABACEAE)
COLLECTED IN THE NORTH OF VIETNAM

Abstract
Caesalpinia sappan L. is used in South East Asia as a dye for food. Studies have shown that
Caesalpinia sappan L. has anti oxidant, anti fungal and anti bacterial activity. The objectives
of this study are to investigate morphological, anatomical properties of branches, leaves and
heartwood and to compare the chemical composition and biological activities of two different
types of heartwood of Caesalpinia sappan L. collected in the North of Vietnam in order to
determine if we can use Caesalpinia sappan L. as a food preservative.

Key words: Caesalpinia sappan L., anatomy, morphology, extraction, chemical analysis,
food preservative, anti oxidant, anti microbial

Introduction
Caesalpinia sappan is found in many different places: in South India, in Sri Lanka, in
Vietnam and South East Asia. It grows wild in mountains and is cultivated in the gardens for
its yellow flowers. (Pawar, Landge, and Surana, 2008) Throughout history, Caesalpinia
sappan has been used as a medicinal plant in South East Asia because of its believed
astringent, depurative, diuretic, or sedative properties and in case of inflammation,
tuberculosis, atonic diarrhea, postpartum tonic, ulcers, stomachaches, skin infections and
nervous disorders (Badami, S., S. Moorkoth, and B. Suresh. 2004). The plant is indicated in
post partum blood stasis, abdominal chest throbbing, swelling and pain due to trauma and
dysentery (Vietnamese Pharmacopoeia). It is also used as food dyeing (meat, chili sauce,
wine) due to the orange-red color of the heartwood.
Even if the proportion changes with the place of collection, Caesalpinia sappan contains
some common chemical products. The composition also varies amongst to the part of the
plant that is analyzed and amongst the moment of the plant collection. Here is a graph of
different secondary metabolites found in Caesalpinia sappan L (Senthilkumar et al. 2011).

Brazilin and brazilein are the two main constituents of Brazil wood.
Her is a recapitulative of the phytochemical constituents of Caesalpinia sappan L (Pawar,
Landge, and Surana 2008)
In the wood was found amyrin (a glycoside), free sugars (lactose, galactose, glucose
and 2-deoxyribose) and free amino acids (such as alanine, aspartic acid, glycine,
proline, valin, leucine, threonine).
In the heartwood was found aromatic compounds (such as brazilin, sappanchalcone,
caesalpin J and P, protosappanin A and B, homoisoflavonods, sitosterol). In the
lignum was found monohydroxybrazilin and benzyl dihydrobenzofuran derivatives,
sappanol, episappanol, brazilin derivatives.
In the heartwood, were also found Sappanol, episappanol, 3-deoxysappanol, 3-0methylsappanol,
3-0-methylepisappanol,
3-0methylbrazilin,
4-0methylepisappanol, sappanon , 3- deoxysappanone , 3-deoxysappanone and
dibenzoxocin derivative, 10-0-methyl-protosappanion , 4,4 dihydroxy-2methoxychalcone, 8-methoxy-bonducellin, quercetin, rhamnetic and ombuin and
juglone, dimeric methanodibenzoxocinone, named neosappanone A rotosappanin A
dimethyl acetal, protosappanin E-2, neosappanone A
In dried heartwood, in addition to 4,4 dihydroxy-2-methoxychalcone, 8-methoxybonducellin, quercetin, rhamnetic and ombuin, 3 other homoisoflavonoirds were
isolated and identified as 7-hydroxy-3- (4-hydroxy-benzylidene)-chroman-4-one, 3,7dihydroxy-3-(4-hydroxy-benzyl)-chroman-4-one and 3,4,7-trihydroxy-3-(4-hydroxybenzyl)-chroman.
In the leafs, the extracted essential oil contained D-a-phellandrene, oscimene tannin,
gallic acid and saponin.
In the pods was found tannins (40%).
In the seed: 7% protein (alanine, cysteine, glycine, isoleucine, lysine, threonine,
tryptiphan, valine) and fatty acid (capric, lauric, myristic, myristopalmatic, palmitic,
palmitoleic, oleic, linoleic, linolecicy and arachidic acids).
In the stem, tetraacetylbrazilin and protosappanin were isolated.

In this study, we will focus on the botanical and chemical aspects of this species in Vietnam
as the objectives are to investigate morphological and anatomical properties, and to analyze
chemical composition and compare antioxidant, antifungal and antibacterial activities of the
Caesalpinia sappan collected in the North of Vietnam.

Materials and Methods

Sample
A first sample (S1) was collected in Hoa Binh province in North of Vietnam on July
27 , 2015. Wood, branch and leaves were available, but flower and fruit were absent. A
second sample (S2) of Caesalpinia sappan L. heartwood was purchased at a local plant store
on the same day. A third sample (S3) was collected in Thai Nguyen on August 3rd, 2015.
Samples of wood, branch and leaves were collected as well as flowers and legumes.
th

Plant identification
The scientific name was determined by using the classification key of the genus
Caesalpinia Linnaeus of published Flora of China.

Morphology analysis
Morphology analysis was performed on S1 and S3. Nikon Eclipse Ci was used to
analyze the characteristics including life form leafs and flowers. Photographs were then
obtained by using a Canon PowerShot G16 or a Sony DSC-W800.
Voucher specimen of samples was deposited at Herbarium of Hanoi University of Pharmacy
(HNIP).

Anatomy analysis
Anatomy analysis was performed on S1. For anatomical analysis, cross sections of
fresh young branch and leaf were prepared by using a razor blade and were double-stained
with methylen blue and carmine red. A light microscope Nikon was used to view the slides
and adjusted to finest resolution and then photographs were obtained by using a Nikon DSFi2

Chemical analysis
Chemical analysis was performed on S1. For chemical analysis, concentrate was
obtained by extraction. 50 gr of wood, gr of dried leaves, gr of dried branch, gr of petioles
were soaked in methanol (100 mL of methanol/10 gr of sample in 3 times) at room
temperature and extracted by bain-marie. The combined extracts were added. Analysis was
performed using TLC. 0,01 gr each concentrate sample was diluted into methanol and then 3
L of each sample was deposed on a silica gel G plaque using HPTLC Camag linomat 5 and

Camag automatic developing chamber ADC2 was used. The mobile phase consisted of
chloroform, acetone and formic acid. Different proportions were tested (8:4:1 8,5:3:1
9;3;0,5 8;5;1).

Biological activity
Samples were sent to the Laboratory of bioassay, Institute of Biotechnology at the
Vietnam Academy of Science and Technology for antioxidant analysis. Here is what the
report states:
Determine potent inhibition of lipid peroxidation method (MDA method)
The experimental method is followed the report of Jelili A Badmus et al (2011) with
minor modification. Potent inhibition of lipid peroxidation of samples were determined
malonyldialdehyde (MDA) formation.
MDA is product of lipid peroxidation,
malondialdehyde (MDA) can react with TBA to produce a red adduct.
The mice were decapitated and the brain was removed carefully, immediately weighed
and homogenzied with ice cold 1.15% KCl to make 10% (1:10) homogenate.
1ml of tissue homogenate was combined with 0.1 ml of sample, 0.8ml of phosphat
buffer, 0.1ml Penton (FeSO4 0.1 mM : H2O2 15mM with rate 1:1) reagents and mixed
thoroughly. Incubate mixture in 370C, for 30 minutes.
Stop reaction with 1 ml of tricloacetic acid 10%.
Centrifuge 12000 rpm for 5 minutes.
Collect 1ml of supernantant and mix with 1ml of thiobarbituric acid 0,8% (rate 2:1).
The solution was heated for 15min in a boiling water bath.
After cooling, the absorbance of the supernatant was measured at 532 nm and
the percentage inhibition was calculated with the formula:
% inhibition of lipid peroxidation = [(ODC ODs)/ODC] 100
+ ODC: Optimal density of control
+ ODs: Optimal Density of sample
Trolox is used as positive control.
Lipid peroxidation is one of the most important organic expression of oxidation stress
(Yagi, 1987). Following peroxidation of N- 6 and N-3 polyunsaturated fatty acids (PUFAs),
relatively unstable fatty acids hydroperoxides may be converted into more stable carbonyls,
among others malondialdehyde (MDA). In fact, MDA formation, often assayed with
thiobarbituric acid (TBA) assay, is the most widely used index of lipid peroxidation in human
and animal studies (de Zwart et al., 1999)
For measurement of the lipid oxidation products in tissue samples of the brain, the
standard procedure using thiobarbituric acid (TBA) reaction under the conditions specified by
Yagi was used (Ohkawa et al., 1979). All measurements were done in triplicate for each
sample concentration.
Because the samples were diluted at: 2000 g/ml, 400 g/ml, 80 g/ml, 16 g/ml
concentration , so final testing concentration of samples were: 200 g/ml, 40 g/ml, 8 g/ml
and 1.6 g/ml.

Samples were sent to the Laboratory of bioassay, Institute of Biotechnology at the Vietnam
Academy of Science and Technology for antimicrobial analysis. Here is what the report
states:
1. Medium, reagent
* Soyabean Casein Digest Agar
Pancreatic Digest of Casein
15.0 g
Papaic digest of Soyabean
5.0 g
Sodium Chlorid
5.0 g
Water
1000 ml
pH 7.3 0.2
* Antibiotics medium
Peptone
6.0 g
Pancreatic digest of casein
4.0 g
Yeast extract
3.0 g
Beef extract
1.5 g
Dextrose
1.0 g
Agar
15.0 g
Water
1000 ml
pH 8.3 0.1
* Sabouraud Dextrose Agar
Dextrose
40.0 g
Mixture of Peptic Digest of Animal Tissue and
Pancreatic digest of Soyabean (1:1)
5.0 g
Agar
15.0g
Water
1000 ml
pH 5.6 0.2
* Buffer No. 1: pH 8.0 0.1
Monobasic potassium phosphate
0.523 g
Dibasic potassium phosphate
16.73 g
Water
1000 ml
Adjust with 18 N phosphoric acid or 10 N potassium hydroxide to a pH of 8.00.1
* Buffer No 2: pH 6.0 0.1
Monobasic potassium phosphate
80.0 g
Dibasic potassium phosphate
20.0g
Water
1000 ml
Adjust with 18 N phosphoric acid or 10 N potassium hydroxide to a pH of 6.00.1
2. Test strains
- Staphylococcus aureus ATCC 6538
- Escherichia coli ATCC 8739

* Preparation of inocula:
Cultivate the organism in Soyabean Casein Digest Agar at 32 to 35 C for 18 - 24 h. After
incubation, havert the organism with 5 ml of sterile saline, using a sterile glass beads. Dilute
an appropriate amount of the havert suspension with sterile saline to give inocula suspension
having turbidity equivalent to McFarland No 2.
3. Preparation Sample solutions
Weight a sufficient amount of dry extract, add sufficient volume of methanol to dissolve,
add Buffer No. 1 to gain S5 solution (50 mg/ml) (see Table 1 below)
Pipette 1000 l of S5, add 1000 l Buffer No. 1 to gain S4 (25 mg/ml).
Pipette 1000 l of S4, add 1000 l Buffer No. 1 to gain S3 (12.5 mg/ml).
Pipette 1000 l of S3, add 1000 l Buffer No. 1 to gain S2 (6.25 mg/ml).
Pipette 1000 l of S2, add 1000 l Buffer No. 1 to gain S1 (3.125 mg/ml).

Samples
TTV2/5
TTV2/7

Table. Weight and dilution

Weight of
Volume of
Volume of Buffer
extract (g)
methanol (ml)
No. 1 (ml)
0.0797
0.300
1.294
0.2879
1.000
4.760

4. Preparation antibiotics solution

4.1. Neomycin sulfate solution (SNeo)
Vietnamese Pharmacopoeia Reference Substance: Neomycin sulfate
Batch: 0413015.02. Potency: 659.4 IU/mg (as is)
Weight 0.0535 g Neomycin sulfate RS into a 100-ml volumetric flash, add Buffer No. 1
to volume to gain Sstock (352.78 IU/ml).
Pipette 5 ml of Sstock into a 100-ml volumetric flash, add Buffer No. 1 to volume to gain
Sm (17.64 IU/ml)
Pipette 6 ml of Sm into a 50-ml volumetric flash, add Buffer No. 1 to volume to gain
SNeo (2.12 IU/ml).
5. Diffusion plate method
5.1. Experimental conditions
- Volume of sample solution ( S5, S4, S3, S2 , S1, SNeo and SNys ) applied in to each hold
(diameter 6 mm): 100 l
- Volume of medium into each plate (diameter 90 mm): 21 ml
+ Base layer (without micro-organism): 12 ml
- S. aureus and E. coli: use Antibiotics medium
+ Seed layer (containing micro-organism): 9 ml
- Incubation temperature and incubation time
+ S. aureus and E. coli: 37 oC/16-18 h
- Volume of inocula suspension : 0.1% (v/v) of working suspension into antibiotics
medium/Sabouraud Dextrose Agar.
6

Results
Morphological properties:
S1:
The tree is small, about 6 m tall; puberulent, but not on old branches. The leaves are
about 40 cm long. Pinnae: 7-13 pairs, opposite, 7,5-15 cm. Leaflet: 9-14 pairs, closely spaced,
sessile, oblong, 1 cm x 2 cm and papery, glabrous. Lateral veins is slender, conspicuous on
both surfaces, contiguous near margin, base oblique, inserted at oblique angles to rachis of
pinnae; retuse apex. No flower and no fruit were collected, as none were present at the
moment of the sample collection.
The morphology matches the Flora of China, though the identification through the
flower characteristics and through fruiting specimens was not full-filled as no flower and no
fruit was available at the time of collection Figure 1.

(c)

(a)
(b)

(d)

(e)
(f)
Figure 1: Caesalpinia sappan L collected in Hoa Binh province

(a) and (b) Leaf of Caesalpinia sappan

(c) and (d) Pinnae of Caesalpinia sappan
(e) and (f) Leaflets of Caesalpinia sappan with veins and retuse apex

S3:
The leaves are about 30-40 cm long. Pinnae: 10 pairs, opposite, 8-15 cm. Leaflet : 1018 pairs, closely spaced, sessile, oblong, 0,8 cm x 1,5 cm and papery, glabrous. Lateral veins
is slender, conspicuous on both surfaces, contiguous near margin, base oblique, inserted at
oblique angles to rachis of pinnae; retuse apex. Bracts are absent (caducous). Pedicel is 1.5
cm and puberulent. Receptable is shallowly campanulate. The five sepals, slightly unequal,
the lower one is larger than others and cucullate. The five petals are yellow, broadly obovate.
Stamen slightly exserted, filaments densely pubescent at lower part. The ovary grayish
velutinous, stalked, 5-ovuled. Style is slender and hairy. The stigma is truncate. The legume
is oblong-ovoid 4 seeded and the apex has a beak. Figure 2

(a)

(d)

(b)

(e)

(c)

(f)

(g)
(h)

(i)

(k)

(l)

(j)

(m)
(n)
Figure 2. Caesalpinia sappan L collected in Thay Nguyen province
(a) Heartwood ; (b) leafs and flowers ; (c) leaf ; (d) leaflet ; (e) flowers ; (f) flower ; (g) and
(h) stamen with pubescent filaments ; (i) base of pubescent filament ; (j) anther ; (k) ovary ;
(l) longitudinal section of flower ; (m) and (n): legume

Leaf anatomy:
The veins consist of an upper and of a lower epidermis of uniform rectangular cells. Cuticle
covers the epidermis. On the upper and on the lower side, collenchyma is composed of
cellulose cell walls and no intercellular space. The parenchyma is composed a 4-6 cell layers.
The palisade parenchyma consists of one or two cell layer of elongated cells under the upper
epidermis. The spongy parenchyma is below the palisade parenchyma and is composed of
around 5 layers of spherical cells loosely arranged with noticeable intercellular space and
calcium oxalate crystal is present. Figure 3 and Figure 4

1
2

3
4
5

Figure 3 : leaf microscopic anatomy of Caesalpinia sappan L.

(1) Lower epidermis; (2) Upper epidermis; (3) Xylem; (4) Phloem;
(5) Sclerenchyma; (6) Mesophyll

7
8
9

10

Figure 4: leaf microscopic anatomy of Caesalpinia sappan L.

(7) Cuticle; (8) Upper epidermis; (9) Palissade parenchyma; (10) Spongy parenchyma.
10

Branch anatomy:
The transverse section of a branch is circular in the outline. The epidermis is
composed of a single layer cells and the cortex is composed of a 8-11 cells layer of different
size. The sclerenchyma is composed of thick walled cells. The phloem is well developed and
consists of many layers of sieve plates, companion cells and phloem parenchyme. The xylem
is also well developed and is composed of parenchyma and vessels arranged irregularly. Soft
and spongy parenchyma cells are of different size and are arranged irregularly compose the
pith at the center of the branch. Few crystals of calcium oxalate are dispersed within the cell.
Figure 5
1
2

4
5
6

Figure 5: branch microscopic anatomy of Caesalpinia sappan L.

(1) Epidermis; (2) Cortex; (3) Pith; (4) Sclerenchyma; (5) Phloem; (6) Xylem

11

Chemical analysis:
Mobile phase consisted of chloroform, acetone and formic acid (8:4:1)

Figure 6: TLC of extracts of Caesalpinia sappan L. under white light

(1) H2O; (2) 45; (3) 70; (4) wood collected; (5) branch; (6) leaf; (7) petiole; (8) wood bought

Figure 7: TLC of extracts of Caesalpinia sappan L. at 254 nm

(1) H2O; (2) 45; (3) 70; (4) wood collected; (5) branch; (6) leaf; (7) petiole; (8) wood bought

12

Figure 8: TLC of extracts of Caesalpinia sappan L. at 366 nm

(1) H2O; (2) 45; (3) 70; (4) wood collected; (5) branch; (6) leaf; (7) petiole; (8) wood bought

Biological activity
Antioxidant activity. The effect of TTV2/5 (methanol extract of wood), TTV2/7 (methanol
extract of leaf) and Trolox in vitro inhibition of lipid peroxidation is showed in The IC50
values of TTV2/5 (methanol extract of wood) and TTV2/7 (methanol extract of leaf) were
3.79 g/ml and >100 g/ml respectively. IC50 of Trolox was 10.68 g/ml.

Figure 9: Inhibition of lipid peroxidation

Final
Concentration
(g/ml)
100
20
4
0.8
IC50 (g/ml)
Table 1: Percentage

% inhibition
TTV2/5

TTV2/7

Trolox

78.91
76.27
54.00
28.22

48.50
34.24
13.41
8.59

3.79 1.13

>100

81.12
58.56
40.83
10.30
10.68
1.17

of lipid peroxidative inhibition activity (%)

13

Anti microbial
Staphylococcus aureus ATCC 6538:

Sample
TTV2/5
TTV2/7

S1

S2

S3

S4

S5

SNeo

Plate 1

17.46

18.98

22.60

27.30

31.37

16.39

Plate 2

17.22

19.22

22.57

27.45

31.60

16.20

Plate 1

16.08

Plate 2

16.20

Table 2. Diameter of inhibition zone (mm) with S. aureus

Escherichia coli ATCC 8739

Sample
TTV2/5
TTV2/7

S1

S2

S3

S4

S5

SNeo

Plate 1

9.72

11.79

13.20

14.40

12.46

Plate 2

9.80

11.98

12.91

14.25

12.47

Plate 1

12.64

Plate 2

12.78

Table 3. Diameter of inhibition zone (mm) with E. coli

14


Discussion
As for the chemical analysis, different mobile phases were tested but the results were
unsatisfactory. The most adequate mobile phase that gave the best TLC results consisted to
chloroform, acetone and formic acid at a ratio of 8:4:1. The bands in the middle (Rf around
0,3-0.6) are not distinguishable enough as the separation is not good enough. However, the
bands from the wood collected (4) and the wood bought (5) are very similar in position and
intensity, meaning that they contain the same compounds in approximately the same quantity.
The sample from the leaf (6) show a band at Rf =1 which is probably chlorophyll. In the
branch (5) and in the petiole (7), few compounds were revealed with this TLC system,
compounds that are different from the samples from the wood (Rf, colour and intensity are
different). No comparison was possible with the results in the Pharmacopoeia of China.
Indeed, we did not dispose of the same stationary phase. Also, to have more precise results,
heartwood at different ages could have been used as samples to see if the composition varies
with age.
Anti oxidant result showed that TTV2/5 (methanol extract of wood) inhibited lipid
peroxidation better than Trolox (standard used) and that TTV2/7 (methanol extract of leaf)
showed no anti oxidant activity. This can be explained by the difference of compounds in the
wood and in the leaf. One or more compound present in the wood and absent in the leaf is
very probably responsible of the strong antioxidant activity. Those results are very conclusive
as for the potential use of Caesalpinia sappan heartwood in food conservative. Isolation and
identification of the anti oxidant compound(s) in the wood should be the next step of the
research.
Anti microbial activity of wood methanol has been proven. Against S. aureus (cocci Gram +),
the lower concentration tested of wood methanol extract (3.125 mg/ml) had a slightly bigger
diameter of inhibition zone that neomycin 2,12 UI/ml (17,46 mm against 16,39 mm). At 50
mg/mL of extract, the diameter of inhibition zone was almost twice the diameter of inhibition
with neomycin (41,37 mm against 16,39 mm). This means that the wood of Caesalpinia
sappan L. contains compounds that possess a strong activity against S. aureus (Cocci Gram +)
and that the anti bacterial activity of wood methanol extract is higher than the standard.
Against E. coli, the antimicrobial activity was weaker than against S. aureus. Indeed, at low
concentrations tested (3,125 mg/ml, 6,25 mg/ml and 12,5 mg/ml), the diameter of inhibition
was smaller than with the standard, neomycin (2,12 UI/ml). At higher concentrations (25
mg/mL and 50 mg/ml), the diameter of inhibition was slightly superior that the standard
neomycin 2,12 UI/ml (13,20 mm, 14,40 mm and 12,46 mm respectively). This means that the
compounds in methanol extract of Caesalpinia wood possess a stronger antibacterial activity
against Gram + than Gram -. It would be interesting to search for the mechanism of action of
the activity of the compound(s) to understand why the activity is higher with Gram + bacteria.
As for leaf methanol extracts, there was no activity against S. aureus (cocci Gram +) and E.
Coli (bacilli Gram -). This means that compounds that are responsible for the antimicrobial
activity of Caesalpinia sappan L. are absent in the leaf and present in the wood.

15

The results confirm the results obtained in previous article (Nirmal and Panichayupakarant,
2015; Badami S, Moorkoth and al, 2003)

Conclusion
The sample of Caesalpinia sappan L was described and identified. The results show
that the samples share common characters with the description of the species in the Flora of
China. The chemical analysis did not yield enough exploitable results but the two types of
wood tested showed very similar chemical composition. Methanol extract of wood exhibited a
strong lipid peroxidative inhibition with low IC50 values whereas methanol extract of leaf
showed no antioxidant activities at all tested concentrations. No antibacterial activity was
detected with methanol extract from the leaf, whereas some antibacterial activity was shown
with wood methanol extract. The antibacterial activity was shown to be stronger against Gram
+ than against Gram bacteria.
This study deepens the knowledge on the antioxidant and anti microbial properties of
Caesalpinia sappan L and confirms the interest of potential use of Caesalpinia sappan L. as a
food preservative in addition to is dyeing use.

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Vietnamese Pharmacopoeia
Flora of China
http://efloras.org/florataxon.aspx?flora_id=2&taxon_id=200011982

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