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Study on the structure and biological activity of some compounds isolated from the halong palm (Livistona halongensis TH Nguyen & Kiew) and gotu kola [Centella asiatica(Linn.) Urban] - 2

The leaves can be used as vegetables. The palm fruit can be cooked and eaten or pressed for oil, and is a specialty of western Nghe An [10].

The roots of the male clematis plant are used to treat leucorrhea and vaginal discharge. They are often combined with other herbs such as areca root, bamboo root, and hook root in equal amounts. The decoction is concentrated and taken twice a day. Daily dosage is 6 - 12 g [11].

According to oriental medicine, the saw palmetto tree ( Livistona chinensis ) has a sweet and astringent taste, neutral properties, the seeds help to eliminate cancer and tumors, the roots have pain-relieving effects [11, 12]. Chinese folk medicine uses saw palmetto seeds to treat cancer of the nose, throat, esophagus, vegetable cancer, leukemia. The roots of this tree are used to treat asthma, reduce pain caused by injections. Dosage 15-30 g, in decoction form. Leaves are used to treat uterine bleeding 1, 11].

Chinese prescriptions containing saw palmetto:

- Treating malignancy: Use 30g of saw palmetto seeds, cook with 30g of lean pork for 2 hours.

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hour.

- Uterine bleeding: Use palm leaf stalks, burn them to ashes, mix with water

Study on the structure and biological activity of some compounds isolated from the halong palm (Livistona halongensis TH Nguyen & Kiew) and gotu kola [Centella asiatica(Linn.) Urban] - 2

drink, or roast and boil to drink.

- In folk medicine, the seeds of the saw palmetto L. chinensis R.Br. are called "Quỳ thư tử".

1.1.2. Research status on palm genus


1.1.2.1. Chemical composition


* Domestic research:

Previously, there were almost no domestic studies on palm trees. In early 2011, Giang Thi Kim Lien and colleagues announced in the Chemistry journal that they had isolated 4 compounds from extracts of Livistona chinensis fruit , including: 5,7,4'-trihydroxy–3',5'–dimethoxy–flavon (tricin, 1 ), 2–(hydroxy–methyl) phenyl–D–glucopyranosid (salicin, 2 ), stigmast–5,22–dien–3β–O–β–D–glucopyranosid (stigmasterol glucosid, 3 ), saccharose ( 4 ) [13].

3'

OCH 3

2' 4' OH

O

HO 8 9 2 1'

7 6'

5'

OCH 3

6

5 10 4 3

OH O


1. Tricin


COUGH


O HO


O

OH OH

COUGH


2. Salicin


2 9


2 1


1 9

1 2


11 13

1 18 H

9 14

2

1 0 8


2 8

2 2 2 4 2 7

25

2 0 2 3


17

26

16


15

COUGH

6 ' O

5 ' O

HH


3 4 5 7

6

4' HO 1 '


HO 3' 2'

COUGH


3. Stigmasterol glucoside


HO 6

5 O

4OH​

HO 3 2

COUGH


HO 1'

O

1 2' HO 5'

O

3' 4' CH 2 OH

COUGH


4. Sucrose


* World research:

Among the palms, saw palmetto has been extensively studied for its chemical composition and biological activities. Singh, RP and Kaur G. (India) qualitatively studied the chemical composition and found that phenolic compounds are present in high concentrations [14].

Maurer – Menestrina and colleagues (Brazil) isolated and determined the structure of a polysaccharide with multiple substituents from saw palmetto resin [15].

Tao Yuan and colleagues isolated and determined the structure of 14 compounds in saw palmetto fruit, including 3 new substances: two depsidons ( 5 , 6 ), one benzofuran ( 7 ) and 11 known compounds: 3-stilbenes, 4-steroids, 3-flavan-3-ol, and 1 alkaloid: trans-3,5,3',5'-tetrahydroxy-4'-methoxy-stilbenes ( 8 ), cis-3,5,3',5'-tetrahydroxy-4'-methoxy-stilbenes ( 9 ), 4-hydroxy-3',5'-dimethoxystilbenes

( 10 ), 5α,8α-epidioxy-22E-ergosta-6,22-dien-3 β -ol ( 11 ), 5α,8α-epidioxy-22E-

ergosta-6,9,22-trien-3 β -ol ( 12 ), 24-ethylcholest-4-en-3-one ( 13 ) , 6 β -hydroxy-

stigmast-4-en-3-on ( 14 ), catechin ( 15 ), epicatechin ( 16 ), epiafzelechin ( 17 ),

terreusinone ( 18 ) [16].



8

O

6

7

5

1

4

3 2

9

O

1'

6'

5'

2'

3'

4'

7'

O H


HO OH


COUGH

5. Depsidon 1


O


8

O

6

7

5

1

4

3

2

O

9

COUGH

6'

1'

5'

2'

3'

4'

COUGH


7'

6. Depsidon 2


CH 3


OH



3' 2'

4' 2

HO 1'


4 5

3a

3

1a 7

O

OCH 3

R 1


6


R 2

R 3


R 4


R 5

5' 6'

OCH 3

8. (E) R = R = R = R =OH R = OCH

1 2 3 5 4 3

7. Benzofuran

9. (Z) R 1 = R 2 = R 3 = R 5 =OH R 4 = OCH 3

10. (E) R 1 = R 2 = OCH 3 R 4 = OH R 5 = R 3 =H






From saw palmetto fruit, Xiaobin Zeng and colleagues isolated 11 compounds.

Flavonoids with 3 new substances ( 19 , 20 , 21 ) and 8 known substances: tricin ( 1 ), quercetin

3- O-β-D -glucopyranoside ( 22 ), isorhamnetin 3- O-β-D -glucopranoside ( 23 ),

rhamnazin 3- O-β-D -glucopyranoside ( 24 ), (-)-epiafzelechin ( 25 ), (+)–catechin

( 26 ), 2 R ,3 R -3,5,7,3',5' pentahydroxyflavan ( 27 ), (–)-catechin ( 28 ) [17].



OH


HO

OH


OH

OH

OH

OH

HO


HO OH

OH

19 . 2 S ,3 S -3,5,7,3',5'-pentahydroxyflavan

20 . 2 R ,3 R -3,5,6,7,8,4'-hexahydroxyflavan


OH

O

OH

OH



COUGH

OH


COUGH

OH

21 . 2 R ,3 R -3,5,6,7,8,3',5'-heptahydroxyf lavan


In particular, from the Australian palm tree ( Livistona australis ), in 2009, Samy K El-Desouky (Egypt) and colleagues isolated from the leaves a new substance, a pyranone derivative: 3-hydroxy-2-(4-hydroxyphenyl)-6-methyl-4H-pyran-4-one ( 29 ) [18]. In 2011, Mona ES Kassem at the National Research Center (Egypt) and colleagues isolated a new salt compound: flavone glycoside.

sulfate ( 30 ) and 14 known flavonoid compounds, including: genkwanin-6-C-β- glucopyranosid ( 31 ), genkwanin-8- C-β - D -glucopyranosid (32 ), isovitexin

( 33 ), isoorientin ( 34 ), orientin ( 35 ), tricin 7- O-β - D -glucopyranoside ( 36 )

tricine 4'- O-β- glucopyranoside ( 37 ) luteolin 7- O-β -glucopyranoside ( 38 ),

quercetin 3- O- -glucopyranoside ( 22 ) quercetin 3- O-β -galactopyranoside ( 39 ),

tricin ( 1 ), quercetin ( 40 ), apigenin ( 41 ), and luteolin ( 42 ) [19].



O

O

COUGH

OH


COUGH​

OSO 3 Na

OCH 3


O


OH OCH 3


H 3 CO


H


H

Glu OH

O

H


H

OH O


30. Flavone sulfate glycoside

OH O

32. Genkwanin-8-C- -D-glucopyranoside







41. Apigenin 42. Luteolin


1.1.2.2. Biological activity


In Vietnam, Giang Thi Kim Lien and colleagues reported the results of biological activity testing of extracts from saw palmetto fruit as follows: n-hexane and MeOH extracts have growth inhibitory activity against Gram (+) bacteria Staphylococcus aureus with IC 50 concentrations of 46.77 and 209.71 μg/ml, respectively. In terms of antioxidant activity, MeOH extract of saw palmetto fruit has peroxidase enzyme inhibitory activity with IC 50 of 61.22 μg/ml. MeOH extract of saw palmetto fruit has cytotoxic activity against 3 tested cancer cell lines: KB (epithelial cancer), MCF-7 (breast cancer) and Hep-G2 (liver cancer) with IC 50 values ​​of 68.04; 88.30 and 101.25 μg/ml, respectively [13].

Singh, RP and Kaur G. (India) reported the in vitro antiangiogenic and antiproliferative activities of the fruit and seed extracts of saw palmetto. The phenolic fraction of the plant exhibited hemolytic activity [ 20 ]. The authors also hypothesized that the high content of phenolic compounds in saw palmetto was responsible for cell death [14].

The research group of Hoang WC (Taiwan) reported the inhibitory activity of epidermal growth factor (EGF) and mitogen-activated protein kinase (MAPK) in human cancer cell lines by a protein fraction denoted LC–X isolated and purified from saw palmetto seeds [21].

Zhong ZG and colleagues reported that the ethyl acetate extract of saw palmetto root exhibited growth inhibitory activity against seven experimental cancer cell lines, including: gastric cancer SGC 7901, leukemia L 1210, P 388D1, laryngeal cancer Hela, liver cancer Hele 7404, melanoma B16 and mouse-rat hybrid neuroblastoma NG 108-15 [22].

The alcoholic extract and aqueous extract of saw palmetto seeds were studied in detail by Cheng S. and colleagues for their inhibitory activity against leukemia cells HL 60, the results showed that the alcoholic extract had better activity [23].

Muneo Tsukiyama and colleagues (Japan) studied the anti-fat accumulation, skin tightening, anti-wrinkle, and slimming effects of saw palmetto seed extract. Therefore, it is possible to study the use of saw palmetto seed extract in cosmetics [24].

In addition, flavan compounds were isolated from saw palmetto fruits such as 3

new substances ( 19 , 20 , 21 ) and (-)-epiafzelechin ( 25 ), (+)-catechin ( 26 ), 2R,3R-

3,5,7,3',5' penthahydroxyflavan ( 27 ), (–)-catechin ( 28 ) are known to

Outstanding biological activities such as:


*.) Antioxidant activity

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