1

MINISTRY OF EDUCATION AND TRAINING
VINH UNIVERSITY

VU THI HIEN

STUDY ON CHEMICAL CONSTITUENTS
AND BIOLOGICAL ACTIVITY OF FRUITS OF
Aphanamixis polystachya (Wall.) R.Parker,
Khaya senegalensis A. Juss AND Melia azedarach L.
BELONGING TO THE FAMILY MELIACEAE IN
VIETNAM
MAJOR: ORGANIC CHEMISTRY
Code: 62.44.01.14

PhD THESIS SUMMARY

NGHE AN - 2018


2

The present study has been completed at: Specialized Lab Organic
Chemistry, Vinh University

Supervisors:
1. Assoc. Prof. Dr. Vu Dinh Hoang
2. Assoc. Prof. Dr. Hoang Van Luu

Reviewer 1: Assoc. Prof. Dr. Trinh Thi Thuy

Reviewer 2: Assoc. Prof. Dr. Do Quang Huy

Reviewer 3: Assoc. Prof. Dr. Le Duc Giang

The thesis will be defended at the High-tech buildings at Vinh
University, 182 Le Duan, Vinh City, Nghe An Province, 2019
At 8 h 00

The thesis can be found at:
1. The National Library of Vietnam
2. Centre for information - Library Nguyen Thuc Hao, Vinh
University


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1. Preamble
In recent years there are many traditional medicinal plants that are subjected to
the research in experimental and clinical treatment of cancer. There have discovered
a number of new substances, many of which are promising substances and become
lead compounds.
The family Meliaceae is interested in the world with a very diverse and rich
chemical composition including limonoid, mono-, di-, sesqui-, and triterpenoid,
coumarin, chromone, lignan and flavonoid classes. ... especially the limonoid class
near 2000 interesting structural compounds, with antifungal, antimicrobial, and
insecticidal activity. Many limonoid compounds exhibit antimicrobial, cytotoxic,
anti-tumor and anti-HIV activity.
Species Aphanamixis polystachya, Khaya senegalensis and Melia azedarach
belong to Vietnamese folk medicinal plants. However, until now, almost no research

on the chemical composition and biological activity of these plants in Vietnam has
been reported. This thesis is aimed to clarify the use in folk, improve the
effectiveness and safety of medicinal plants, develop medicinal materials to use in a
more scientific way. Therefore, the study field has important theoretical and
practical significance, making an important contribution to finding natural resources,
economic value of Vietnam's natural medicinal resources. For that reason, we have
chosen the topic: "Study on chemical composition and biological activity of
fruits of Anphanamixis polystachya, Khaya senegalensis and Melia azedarach
belonging to family Meliaceae in Vietnam”
2. Objects
The research objects of the thesis are extracts from fruits of Anphanamixis
polystachya, Khaya senegalensis and Melia azedarach in Vietnam.
3. Tasks
The research tasks include:
- Selecting suitable solvents to extract the existing compounds from fruits of
Anphanamixis polystachya, Khaya senegalensis and Melia azedarach in
Vietnam.
- Separating and identifying structures of the compounds isolated.
- Assaying biological activities of the concerned compounds.
4. Methods
- Collection samples: collection, identification, cultivation for some fungi,
storage and preservation dried fungi of 2 samples at the laboratory temperature
0
(20-30 C).
Isolation of compounds by a combination of chromatographic techniques;
column chromatography (CC), thin layer chromatography (TLC) with different


4


stationary phases are silica gel, Sephadex LH-20, RP-18; high-performance liquid
chromatography (HPLC).
- Structure elucidation by UV, IR, mass spectrometry (MS), as well as one and
1
13
1 1
two dimensional NMR techniques ( H-NMR, C-NMR, 2D- H- H-COSY,
HMBC, HSQC).
- Test of anti-inflammatory and antibacterial activities and plant pathogenic
antifungal activity of pure compounds.
5. New contributions of the thesis
Study the chemical composition and biological activity of fruits of Anphanamixis
polystachya, Khaya senegalensis, Melia azedarach in Vietnam, we have
obtained some results as follows:
1. Isolated and determined the structure 6 compounds from fruits extract of
Aphanamixis polystachya, include:
- 04 limonoid compounds: dysobinin, chisocheton compound E, chisocheton
compound G và 6α - acetoxyepoxyazadiradione VI.
- 02 sterol compounds: β-sitosterol, -sitosterol-3-O--D-glucopyranoside.
dysobinin, chisocheton compound E, chisocheton compound G và 6α acetoxyepoxyazadiradione VI were isolated for the first time.
2. Isolated and determined the structure 8 compounds from fruits extract of
Khaya senegalensis, include:
- 04 limonoid compounds: seneganolide, khayanone, khayanolide B, 6-acetoxymethyl angolensate.
- 02 flavonoid compounds: (-)-epicatechin and quercitrin.
3. Isolated and determined the structure 8 compounds from fruits extract of Melia
azedarach, include:
01
new
limonoid
compound

3α,12α-diacetoxy-7α-benzoyloxy-1αhydroxytrichilinin which is called trichilinin F.
- 02 flavonoid compounds: apigenin and quercetin 3-O-[-L-rhamnopyranosyl(1→6)]--D-glucopyranoside).
- 01 triterpenoid compound: taraxerol
- 02 phenolic compounds: scopoletin and acid vanillic
- 02 sterol compounds: β-sitosterol, -sitosterol-3-O--D-glucopyranoside.
4. Test of anti-inflammatory biological activity and antifungal activity that causes
plant diseases. Evaluate the antifungal activity of compounds isolated with C.
acutatum, C. fragariae, C. gloeosporioides, F. oxysporum, B. cinerea và P.
obscurans.
6. Outline of the thesis


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It is displayed in a total of 112 pages with 21 tables, 19 figures, 3 diagrams.
Its major sections include: Introduction (4 pages), overview (25 pages), methods
and experiment (20 pages), results and discussion (69 pages), conclusion (1
pages), published works (1 page). Morever, there is an appendix with 130 spectra
of the compounds.

CHAPTER 1: OVERVIEW
The thesis has conducted a literature review content:
1. Family Meliaceae
- Introduction of common plant characteristics of species belonging to the
Meliaceae family, the main chemical composition of family Meliaceae as
limonoid mono-, di-, sesqui-, and triterpenoid, coumarin, chromone, lignan,
flavonoid and phenolic compounds… Besides, the review also mentions the
biological activity and application of the family Meliaceae in agriculture,
pharmaceutical ...
2. Species Aphanamixis polystachya

- Introduction of botanical characteristics of Aphanamixis polystachya
- The chemical composition of Aphanamixis polystachya
- The biological activity of Aphanamixis polystachya
3. Species Khaya senegalensis
- Introduction of botanical characteristics of Khaya senegalensis
- The chemical composition of Khaya senegalensis
- The biological activity of Khaya senegalensis
4. Species Khaya senegalensis
- Introduction of botanical characteristics of Melia azedarach
- The chemical composition of Melia azedarach
- Biological activity of Melia azedarach

CHAPTER 2: METHODS AND EXPERIMENT
2.1. Methods
2.1.1. Method of collecting samples
The plant material is collected at the appropriate time of the year. When fresh
plant material is required for study, they are washed, stored in cool place,
isolation, preservation, and fermentation. They are stored at appropriate
conditions for the experiment.


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2.1.2. Methods of separation
Thin layer chromatography (TLC); column chromatography (CC); lash
column chromatography (FC); high performance liquid chromatography (HPLC);
fractional crystallization.
2.1.3. Methods of identifying the component structure
Using modern spectroscopic methods to demonstrate structure of obtained
compound consisting of ultraviolet (UV), infrared (IR), mass spectrometry (ESI1

13
MS, HR-ESI-MS), nuclear magnetic resonance spectroscopic H-NMR, C1 1
NMR, DEPT and HSQC, HMBC, H- H COSY
2.1.4. Methods of bioactivity assay
Test anti-inflammatory activity and plant anti-fungal activity. Evaluate the
antifungal activity of compounds isolated with C. acutatum, C. fragariae, C.
gloeosporioides, F. oxysporum, B. cinerea và P. obscurans.
2.2. Chemicals and equipment
2.2.1. Chemicals: Solvents for extraction plant material are pure. The solvents
for thin layer chromatography, fast column chromatography are pure analytical
(PA).
2.2.2. Equipment: Melting temperature was determined with a Yanaco MP-S3;
The polarity was determined with a Jasco DIP -370 polarimeter. Thin layer
chromatography (TLC); column chromatography (CC); lash column
chromatography (FC); high performance liquid chromatography (HPLC);
ultraviolet (UV), infrared (IR), mass spectrometry (ESI-MS, HR-ESI-MS),
nuclear magnetic resonance spectroscopic (NMR), optical rotation and melting
points measurement;
2.3. Study on compounds from fruits of Aphanamixis polystachya
2.3.1. Collecting samples
The fruits of Anphanamixis polystachya was collected at the Vu Quang
National Park of Ha Tinh Province, Vietnam, in August 2013 and identified by
Assoc. Prof. Dr. Tran Huy Thai, Institute of Ecology and Biological Resources Vietnam Academy of Science and Technology. A voucher specimen (DHV-2013)
was deposited at the herbarium of the Department of Chemistry, Vinh University.
2.3.2. Isolating substances
The fruits of Anphanamixis polystachya (4.0 kg) were air-dried and
powdered and soaked with methanol at room temperature for 7 days, and the
combined extracts were concentrated under reduced pressure to give deep brown
syrup (290.0 g). The crude extract was suspended into water and partitioned with
cloroform and butanol, successively to afford cloroform (106 g), butanol (35.0 g),

respectively, after removal of the corresponding solvent.


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The chloroform soluble extracts were purified by silica gel column
chromatography eluted with n-hexane and acetone gradients (100:0, 25:1, 15:1,
10:1, 7:1, 5:1) and CHCl3:CH3OH (100:0, 6:1, 3:1, 2:1, 1:1) gradients to afford 7
fractions (F1 to F7).
Fraction F1 (8.6 g) was subjected to silica gel column chromatography
eluted (200 gam, 60 x 5 cm) with n-hexane/acetone (100:0, 25:1, 15:1, 10:1, 4:1)
to afford seven subfractions (F1-1 to F1-7). Subfraction F1-4 was subjected to
the silica gel column chromatography eluted with n-hexane/acetone (100:0, 25:1,
15:1, 10:1, 4:1) to afford AP-5 (153 mg).
Fraction F2 (2.3 g) was subjected to silica gel column chromatography
eluted (200 gam, 60 x 3 cm) with n-hexane/acetone (9:1, 6:1) to afford six
subfractions (F2-1 to F2-6). Subfraction F2-6 was subjected to the Sephadex LH20 column chromatography eluted (50 gam, 60x3cm) with CH3OH:H2O to afford
AP-1 (41 mg).
Fraction F3 (2.7 g) was subjected to silica gel column chromatography
eluted (200 gam, 60 x 3 cm) with n-hexane/acetone (9:1, 6:1, 4:1, 1:1) to afford
four subfractions (F3-1 to F3-4). Subfraction F3-2 was subjected to the phase
reversal (RP -18 ) column chromatography eluted (100 gam, 60 x 3 cm) with
CH3OH:H2O to afford AP-2 (31 mg).
Fraction F4 (4.7 g) was subjected to silica gel column chromatography
eluted (200 gam, 60 x 3 cm) with CHCl3:CH3OH (20:1, 10:1, 6:1, 4:1, 2:1) to
afford five subfractions (F4-1 to F3-5). Subfraction F4-1 was subjected to the
phase reversal (RP -18 ) column chromatography eluted (100 gam, 60 x 3 cm)
with CH3OH:H2O (19:1, 16:1) to afford AP-4 (43 mg) and AP-3 (21 mg).
Fraction F5 (1.5 g) was subjected to silica gel column chromatography
eluted (200 gam, 60 x 3 cm) with CHCl3:CH3OH (9:1, 6:1) to afford AP-6 (13

mg).
2.4. Study on chemical constituents of fruits of Khaya senegalensis A. Juss
2.4.1. Collecting samples
The fruits of Khaya senegalensis A. Juss was collected at the Nghe An
Province, Vietnam, in January 2014 and identified by Assoc. Prof. Dr. Tran Huy
Thai, Institute of Ecology and Biological Resources - Vietnam Academy of
Science and Technology. A voucher specimen was deposited at the herbarium of
the Department of Chemistry, Vinh University.
2.4.2. Isolating substances
The fruits of Anphanamixis polystachya (4.0 kg) were air-dried and
powdered and soaked with methanol at room temperature for 7 days, and the
combined extracts were concentrated under reduced pressure to give deep brown


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syrup (285.0 g). The crude extract was suspended into water and partitioned with
n-hexane and ethyl acetate, successively to afford n-hexane (55g), butanol (95.0
g), respectively, after removal of the corresponding solvent.
The ethyl acetate soluble extracts were purified by silica gel column
chromatography eluted with n-hexane and acetone gradients (100:0; 50:1; 39:1;
30:1; 20:1; 15:1; 9:1; 4:1; 2:1; 1:1) to afford 7 fractions (F1 to F7).
Fraction F3 was subjected to silica gel column chromatography eluted with
n-hexane/acetone (20:1; 15:1; 9:1; 2:1) to afford five subfractions (F3-1 to F3-5).
Subfraction F13-3 was subjected to the silica gel column chromatography eluted
with n-hexane/acetone (9:1; 4:1) to afford KS1 (15 mg) and KS3 (29 mg).
Fraction F4 was subjected to silica gel column chromatography eluted with
chloroform:methanol (9:1) to afford KS4 (12.5 mg).
Fraction F5 was subjected to silica gel column chromatography eluted with
n-hexane/acetone (15:1; 9:1; 4:1; 2:1) to afford seven subfractions (F5-1 to F5-7).

Subfraction F5-2 was subjected to silica gel column chromatography eluted to
afford KS5 (53 mg).
Fraction F5-4 (4.7 g) was subjected to silica gel column chromatography
eluted with chloroform: methanol (15:1, 9:1) to afford KS6 (71.5 mg).


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2.5. Study on chemical constituents of fruits of Melia azedarach
2.5.1. Collecting samples
The fruits of Melia azedarach was collected at the Pu Huong National Park
of Nghe An Province, Vietnam, in August 2016 and identified by Assoc. Prof.
Dr. Tran Huy Thai, Institute of Ecology and Biological Resources - Vietnam
Academy of Science and Technology. A voucher specimen (DHV 2016) was
deposited at the herbarium of the Department of Chemistry, Vinh University.
2.5.2. Isolating substances
The fruits of Anphanamixis polystachya (5.0 kg) were air-dried and
powdered and soaked with methanol at room temperature for 7 days, and the
combined extracts were concentrated under reduced pressure to give deep brown
syrup (425.0 g). The crude extract was suspended into water and partitioned with
ethyl acetate and n-butanol, successively to afford chloroform (106 g), n-butanol
(35.0 g), respectively, after removal of the corresponding solvent.
The ethyl acetate soluble extract was fractionated by silica gel column
chromatography eluted with chloroform and methanol gradients (100:0, 40:1:
30:1; 20:1; 10:1: 4:1; 2:1) to afford 7 fractions (F1 to F7).
Fraction F1 was subjected to silica gel column chromatography eluted with
n-hexane/acetone (15:1) to afford MA6 (128 mg).
Fraction F3 was subjected to silica gel column chromatography eluted with
n-hexane/acetone (7:1) to afford MA3 (28 mg) and MA5 (31 mg).
Fraction F5 was subjected to silica gel column chromatography eluted with

chloroform: methanol (10:1) to afford MA4 (51 mg)
The n-butanol soluble extract was fractionated by silica gel column
chromatography eluted with chloroform and methanol gradients (30:1; 20:1;
10:1: 4:1; 2:1) to afford 5 fractions. Fraction 2 was subjected to the silica gel
column chromatography eluted with chloroform: methanol (15:1) to afford MA1
(12 mg). Fraction 3 was subjected to the silica gel column chromatography
eluted with chloroform: methanol (10:1) to afford MA2 (21.5 mg). Fraction 5
was subjected to the silica gel column chromatography eluted with chloroform:
methanol (10:1) to afford MA7 (41 mg)


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2.6. Biological activity test
Test anti-inflammatory activity and plant anti-fungal activity. Evaluate the
antifungal activity of compounds isolated with C. acutatum, C. fragariae, C.
gloeosporioides, F. oxysporum, B. cinerea và P. obscurans.
CHAPTER 3: RESULTS AND DISCUSSION
3.1. Fruits of Anphanamixis polystachya
Table 3.1: Isolated compounds from fruits of Anphanamixis polystachya
No
Symbol
Name of the compound
Mass (mg)
1
2
3
4
5
6


AP-1
AP-2
AP-3
AP-4
AP-5
AP-6

Dysobinin
Chisocheton compound E
chisocheton compound G
6α - acetoxyepoxyazadiradione VI
β-sitosterol
-Sitosterol-3-O--Dglucopyranoside

41
31
21
43
153
13

3.2. Fruits of Khaya senegalensis
Table 3.2: Isolated compounds from fruits of Khaya senegalensis
No
Symbol
Name of the compound
Mass (mg)
1
2

3
4
5
6

KS1
KS2
KS3
KS4
KS5
KS6

Seneganolide
Khayanone
Khayanolide B
6-Acetoxy-methyl angolensate
(-)-Epicatechin
Quercitrin

34
32
9
22
10
20

3.3. Fruits of Melia azedarach
3.3.1. Isolated compounds
The process of isolating the substances from the fruits of Melia azedarach
was presented in detail in the experimental section. In the course of our research

we have focused on studying the chemical composition of the methanol extract
from leaves Annona reticulata by combining the methods of extraction, thin layer


11

chromatography, silica gel column chromatography, high performance liquid
chromatography (HPLC). The results of the study are shown in Table 3.15
Table 3.15: Isolated compounds from fruits of Melia azedarach
No
Symbol
Name of the compound
Mass (mg)
1
2
3

MA1
MA2
MA3

4
5
6
7
8

MA4
MA5
MA6

MA7
MA8

New
Apigenin
Quercetin
3-O-[-Lrhamnopyranosyl-(1→6)]--Dglucopyranoside
Scopoletin
Acid vanillic
Taraxerol
β-sitosterol
-sitosterol-3-O--Dglucopyranoside

14
12
21,5

28
31
25
128
41

3.1.2. Structural elucidation of new compound MA1
Compound MA1 was isolated as optically active colorless syrup and the
HRESIMS analytical data of 1 revealed the molecular formula as C37H44O9 (m/z
655.2879, [M+Na]+). The UV absorption maxima at 205, 218, 244, and 273 nm
indicated the presence of a conjugated benzene chromophore [99]. The 1H-NMR
spectrum of MA1 (Table 3.2) displayed the characteristic resonances for four
methyl singlets [H 1.00 (6H, CH3-20, -22), 1.18 (3H, CH3-18), and 1.25 (3H,

CH3-21)], one oxymethylene group [H 3.13 (m) and 3.45 (d, J = 7.5 Hz)], and
one set of signals for furan moiety [H 6.16 (br s), 7.13 (br s), and 7.28 (br s)],
respectively, which indicated the basic skeleton of MA1 was similar to that of
trichilinins [48]. In addition, there were also proton signals representative for two
acetyl singlets [H 1.90 (3H) and 1.91 (3H)] and one benzoyl fragment [H 7.43
(2H, t, 7.5), 7.56 (1H, t, 7.5), and 8.08 (2H, d, 7.5)]. Comparison of the above
spectral data with those of trichilinin E [48], the observed difference in 1 was the
presence of one more acetyl group. The substitution position of acetyl and
benzoyl groups were determined by the assistance of comprehensive 2D NMR
spectroscopic examinations of 1. In the HMBC spectrum, 2J, 3J-HMBC
correlations from H-3 to C-1, C-27; from H-6 to C-7; from H-7 to C-1'; from H12 to C-29; from H-15 to C-8, C-17; from H-17 to C-23, C-24, C-26; from CH3-


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18 to C-3, C-4, C-19; from CH3-20 to C-1, C-5, C-9; from CH3-21 to C-14; from
CH3-22 to C-12, C-14, C-17; from H-7' to C-1', respectively, were observed and
established its 2D planar structure as shown (Figure 1). The other successive 2D
experiments constructed the same stereochemical configurations of 1 and
completed the assignments of all the proton and carbon signals. Conclusively, the
chemical structure of 1 was established as 3α,12α-diacetoxy-7α-benzoyloxy-1αhydroxytrichilinin (Figure 1) and named trivially as trichilinin F followed the
previous convention.
Table 3.2: 1H and 13C-NMR data of MA1
STT
δH (J =Hz)
δC
STT
δH (J =Hz)
δC
1

3.56 (br s)
71.8
20
1.00 (s)
15.8
2
1.53 (m). 2.27 (m)
24.3
21
1.25 (s)
27.1
3
5.08 (br s)
72.8
22
1.00 (s)
15.4
4
42.3
23
124.6
5
2.55 (d. 12.5)
40.3
24
7.13 (br s)
140.2
6
4.27 (dd. 12.5. 3.0) 73.6
25

7.28 (br s)
141.9
7
5.85 (d. 3.0)
74.2
26
6.16 (br s)
111.8
8
51.7
27
169.0
9
3.15 (dd. 13.0. 7.5) 36.2
28
1.91 (s)
20.8
10
44.1
29
171.0
11
2.04 (m). 2.36 (m)
30.0
30
1.90 (s)
21.3
12
5.08 (m)
77.8

1’
165.0
13
40.2
2’
130.6
14
155.7
3’
8.08 (d. 7.5)
129.5
15
5.70 (br s)
122.7
4’
7.43 (t. 7.5)
128.3
16
2.32 (m)
36.6
5’
7.56 (t. 7.5)
132.9
17 2.97 (dd. 10.8. 7.5) 50.4
6’
7.43 (t. 7.5)
128.3
18
1.18 (s)
18.8

7’
8.08 (d. 7.5)
129.5
19
3.13 (m). 3.45 (d.
77.9
7.5)


13

(MA-1) A3α,12α-diacetoxy-7α-benzoyloxy-1α-hydroxytrichilinin

Figure 3.16. The ESI-MS spectra of MA1


14

Figure 3.37. The HR-ESI-MS spectra of MA1


15

Figure 3.18. The 1H-NMR spectra of MA1

Figure 3.19. The 1H-NMR spectra of MA1

Figure 3.20. The 1H-NMR spectra of MA1



16

Figure 3.21. The 13C-NMR spectra of MA1


17

Figure 3.22. The 13C-NMR spectra of MA1

Figure 3.25. The DEPT spectra of MA1


18

Figure 3.27. The HMBC spectra of MA1

Figure 3.28. The HSQC spectra of MA1


19

Figure 3.29. The COSY spectra of MA1
3.3. Antimicrobial and antifungal activity of compounds
The food-poisoned technique-used to quantify the antibiotic activity of
compounds against Fusarium oxysporum is determined by mixing the substance
into the molten PDA environment according to the test concentration (200 ppm
and 500 ppm). Petri dishes after transplanting are incubated at 25 ° C after 3 and
7 days and measuring the diameter of the fungus. The antifungal effect is
calculated according to the formula:
CV (%) =100 × (Dc-Dt)/(Dc-4)

Where: Dc: fungus diameter on a petri-controlled plate; Dt: fungus diameter on
petri dish with mixing substance and 4: diameter of PDA at center of disc.


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The chemical compounds isolated from the fruits of Anphanamixis
polystachya
O

23

O

22

21

12

12

17

11

16

1
14


9
3

5

2

15

8

10

10

7

3

6

4

O

13

16


1

OAc

5

4

O

9
6

OAc

OH

20
17

11

13

2

O

23


22

21
20

14

8
7

15

OAc

OAc

(AP-1) Dysobinin

(AP-2) Chisocheton compound G
O
O

23

22

21

21
12


10
3
4

O

5

9
6

24 13

1

16

14

9

10

15

3
4

O


OAc
OAc

5

25

26

8
7

6

O

O

16

14

2
8
7

20
17


11
19

13
1
2

18
12

20
17

11

O

23

22

15

OAc

OAc

(AP-3) Chisocheton compound E (AP-4) 6α -Acetoxyepoxyazadiradione VI
29
28


29
28
21
18
19

24
23

13
9

2

17

11
8

14

10
7

HO

3

4


5

6

(AP-5) β-Sitosterol

27

22
20

12
1

21
12

25

1

HOH2C

O

4'

HO
HO


5'
3'

2'

O

3

4

5

23
17

13
8

16

14 15

10

6'

27
24


18

11
9

2

26
16

15

19

22
20

7
6

1'

OH

(AP-6) -Sitosterol-3-O--D-glucopyranoside

25
26



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The chemical compounds isolated from the fruits of Khaya senegalensis

(KS-1) Seneganolide

(KS-3) Khayanolide B

(KS-5) (-)-Epicatechin

(KS-2) Khayanone

(KS-4) 6-Acetoxy-methyl angolensate

(KS-6) Quercitrin


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The chemical compounds isolated from the fruits of Melia azedarach

(MA-1) 3α,12α-diacetoxy-7α-benzoyloxy-1α-hydroxytrichilinin

(MA-2) Apigenin

(MA-3) Quercetin 3-O-[-L-rhamnopyranosyl(1→6)]--D-glucopyranoside)

(MA-4) Scopoletin


(MA-6) Vanillin

(MA-5) Taraxerol

(MA-7) β-Sitosterol (MA-8) -Sitosterol-3-O--D-glucopyranoside


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CONCLUSIONS
Study on chemical constituents and biological activity of Anphanamixis
polystachya fruits, Khaya senegalensis fruits and Melia azedarach fruits in
Vietnam gains significant achievements which is as follows:
1. From the extract of Anphanamixis polystachya fruits there have isolated and
identified 06 compounds including:
- 04 known limonoid compounds: dysobinin, chisocheton compound G,
chisocheton compound E and 6α - acetoxyepoxyazadiradione VI;
- 02 known sterol compounds: β-sitosterol, -sitosterol-3-O--Dglucopyranoside.
2. From the extract of Khaya senegalensis fruits have isolated and identified 06
compounds including:
- 04 known limonoid compounds: seneganolide, khayanone, khayanolide B, 6acetoxy-methyl angolensate;
- 02 known flavonoid compounds: (-)-epicatechin and quercitrin.
3. From the extract of Melia azedarach fruits have isolated and identified 06
compounds including:
- 01 new limonoid compound: 3α,12α-diacetoxy-7α-benzoyloxy-1αhydroxytrichilinin (trichilinin F).
- 02 known flavonoid compounds: apigenin and quercetin 3-O-[-Lrhamnopyranosyl-(1→6)]--D-glucopyranoside).
- 01 known triterpenoid compound: taraxerol;
- 02 phenolic compounds: scopoletin and acid vanillic;
- 02 sterol compounds: β-sitosterol, -sitosterol-3-O--D-glucopyranoside.
4. Evaluation of antifungal activity of isolated compounds AP2, AP3, KS2, KS3,

KS4 against Fusarium oxysporum. The results showed that KS3 has strong
antifungal activity with inhibitory effect of over 80% at 500ppm concentration
and no decline after 7 days of culture.


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PUBLISHED WORKS
1. Vu Thi Hien, Tran Thi Ngoc Han, Pham Thi Hang, Tran Dinh Thang
(2013), The tertranortriterpenoid compounds from the fruits of
Anphanamixis polystachya (Wall.) Parker) (Meliaceae) in Vu Quang – Ha
Tinh, Journal of Chemistry, T.51 (6ABC), 68-71.
2. Vu Thi Hien, Nguyen Thi Thanh Phuong, Tran Dinh Thang (2014), The
limonoid compounds from the fruits of Anphanamixis polystachya (Wall.)
Parker) (Meliaceae), Journal of Science and Technology, T.52 (5A), 49-54.
3. Vu Thi Hien, Vu Dinh Hoang (2016), Chemical constituents of fruits of
Khaya senegalensis A. Juss growing in Vietnam, Vietnam Journal of
Chemistry, International Edition, 54(6) 781-785.
4. Vu Thi Hien, Nguyen Ngoc Tuan, Hoang Van Luu, Vu Dinh Hoang (2018),
Isolation and structure determination of compounds from Melia azedarach
fruits in Vietnam, Journal of Science and Technology (Technical
Universities) (Accepted)
5. Vu Dinh Hoang, Vu Thi Hien, Nguyen Ngoc Tuan, Ping-Chung Kuo,
Tian-Shung Wu, Tran Dinh Thang (2018), Chemical constituents of fruits of
Melia azedarach growing in Vietnam, Nat. Prod. Res. (submitted).