NatPro - Isolation of Flavonoids From the Fruits of Cornus Kousa Burg

7/28/2019 NatPro - Isolation of Flavonoids From the Fruits of Cornus Kousa Burg

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Isolation of Flavonoids from the Fruits of Cornus kousa Burg.

Dae-Young Lee,

Ha-Na Lyu,Ho-Young Kwak,

Lakoon Jung,

Youn-Hyung Lee,

Dae-Keun Kim,

In-Sik Chung,Sung-Hoon Kim

and Nam-In Baek,

Presented by

Ekrima Astari


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Cornus kousa Taxonomy

Kingdom:Plantae

(unranked):Angiosperms

(unranked):Eudicots

(unranked):Asterids

Order:Cornales

Family:Cornaceae

Genus:Cornus

Subgenus:Benthamidia

Species:C. kousa

Small deciduoustree 812 m (2639 ft) tall,

Native to eastern Asia.

Like most dogwoods, it has opposite,

simple leaves, 410 cm long.

The tree is extremely showy when in bloom, but

what appear to be four petaled white flowers.

The blossoms appear in late spring, weeks after

the tree leafs out.
http://en.wikipedia.org/wiki/Plantaehttp://en.wikipedia.org/wiki/Angiospermshttp://en.wikipedia.org/wiki/Eudicotshttp://en.wikipedia.org/wiki/Asteridshttp://en.wikipedia.org/wiki/Cornaleshttp://en.wikipedia.org/wiki/Cornaceaehttp://en.wikipedia.org/wiki/Dogwoodhttp://en.wikipedia.org/wiki/Deciduoushttp://en.wikipedia.org/wiki/Treehttp://en.wikipedia.org/wiki/Native_planthttp://en.wikipedia.org/wiki/Dogwoodhttp://en.wikipedia.org/wiki/Leafhttp://en.wikipedia.org/wiki/Flowerhttp://en.wikipedia.org/wiki/Flowerhttp://en.wikipedia.org/wiki/Leafhttp://en.wikipedia.org/wiki/Dogwoodhttp://en.wikipedia.org/wiki/Native_planthttp://en.wikipedia.org/wiki/Treehttp://en.wikipedia.org/wiki/Deciduoushttp://en.wikipedia.org/wiki/Dogwoodhttp://en.wikipedia.org/wiki/Cornaceaehttp://en.wikipedia.org/wiki/Cornaleshttp://en.wikipedia.org/wiki/Asteridshttp://en.wikipedia.org/wiki/Eudicotshttp://en.wikipedia.org/wiki/Angiospermshttp://en.wikipedia.org/wiki/Plantae


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Cornus kousa

Cornus kousa Burg. (Cornaceae) is a tree distributed in the mountains of Korea, China

and Japan.

The fruit of this plant has been used as:

hemostatic agent

treatment ofdiarrhea in Korean traditional medicine

immuno-regulatory

Some chemical constituents such as isoquercitrin, gallic acid, tannin, phenolics and

flavonoids have been reported from the leaves of C. kousa.

Also, our previous phytochemical researches on the fruits of this plant reported the

presence ofsteroids and cytotoxic lignans


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Isolated CompundsAromadendrin 7-O--D-glucoside

Quercetin 3-O-rutinoside

Quercetin 3-O--D-galactoside

Quercetin 3-O--D-glucoside

Quercetin 3-O-a-L-rhamnoside

Kaempferol 3-O--D-galactoside

Quercetin 3-O--D-glucuronide


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Isolated Compunds Lactones

Triterpenes and Lignans

Triterpenes Glycosides Sterols

Loganin


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E i


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ExperimentsBuah 10kg

Dicincang

Diekstraksi 3x methanol 80%

EvaporasiEtil Acetat (2L x 3) dan H2O (2L)

n-hexane-EtOAc (4 : 1 2 : 1, 1.5 L)

CHCl3-MeOH (15 : 113 : 110 : 1, 1.5 L)

TLC

44g

CKFE1 2.5g

CKFE1-2 88mg

CHCl3 MeOH-H2O (13 : 3 : 1, 3 L)

Senyawa 1 35mg

MeOH H2O (2 : 1, 1 L)

MeOH-H2O (2 : 3, 2 L)

CKFE2 870mg

CHCl3-MeOH-H2O (12 : 3 : 1,2.5 L)

CKFE2-1 310mg

2CKFE2-1-1 (35 mg)

80% MeOH

Senyawa 2 35mg

2CKFE2-1-2 (35 mg)


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Experiments2CKFE2-1-2 (35 mg)

HPLC

CH3CN-H2O-TFA (50 : 50 : 0.05, vol. %)370 nm by UV detector

2 peak: 2.97min dan 3.65min

Senyawa 3 Senyawa 4


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Result and Discussion

Compound 1: Light yellow powder

Compound 2: Yellow amorphous powder

Compound 3: Yellow powder

Compound 4: Yellow powder


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Compound 1

m.p. 178- 180;

UV (MeOH) max: 269, 364 nm;

IR (KBr) max 3350, 1660, 1610, 1500 cm1;

EI/MS m/z: 286[M+], 258, 229, 213, 184, 153,121;1H-NMR(400 MHz, CD3OD, )

8.06 (2H, d, J = 9.2 Hz, H-2'/6'),

6.89 (2H, d, J = 9.2 Hz, H-3/5'),

6.36 (1H, d, J = 2.0 Hz, H-8),

6.16 (1H, d, J = 2.0 Hz,H-6);

H

H


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Compound 2

m.p. 230-232oC;


[]25 D= +16.0o

(c = 1.1, MeOH);IR(KBr) max 3420, 1680 cm1; pos.

FAB/MS m/z: 449, 287;

1H-NMR (400 MHz, CD3OD, )

8.04 (2H, d, J = 8.4 Hz, H-2'/6'),

6.87 (2H, d, J = 8.4 Hz, H-3'/5'),

6.38 (1H, br s, H-8),6.19 (1H, br s, H-6),

5.23 (1H, d, J = 7.2 Hz, H-1''),

3.18~3.70 (4H, m, H-2'', 3'', 4'', 5''),

3.71 (1H, dd, J = 12.0, 2.4 Hz, H-6a''),

3.58(1H, dd, J = 12.0, 5.2 Hz, H-6b'');

H


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Compound 2

m.p. 230-232oC;


[]25 D= +16.0o

(c = 1.1, MeOH);IR(KBr) max 3420, 1680 cm1; pos.

FAB/MS m/z: 449, 287;


8.04 (2H, d, J = 8.4 Hz, H-2'/6'),

6.87 (2H, d, J = 8.4 Hz, H-3'/5'),

6.38 (1H, br s, H-8),6.19 (1H, br s, H-6),

5.23 (1H, d, J = 7.2 Hz, H-1''),

3.18~3.70 (4H, m, H-2'', 3'', 4'', 5''),

3.71 (1H, dd, J = 12.0, 2.4 Hz, H-6a''),

3.58(1H, dd, J = 12.0, 5.2 Hz, H-6b'');

H


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Compound 3

m.p. 235-238oC;


[]25D= 12.5o

(c = 0.9, MeOH); neg.FAB/MS m/z: 463 [M-H], 447, 431, 389, 339, 325, 301;

IR (KBr) max 3400, 2919, 1656, 1606, 1508 cm1;


7.84 (1H, d, J = 2.4 Hz, H-2'),

7.56 (1H, dd, J = 2.4, 8.6 Hz, H-6'),

6.84 (1H, d, J = 8.6 Hz, H-5'),6.34 (1H, d, J = 2.0 Hz, H-8),

6.16 (1H, d, J = 2.0 Hz, H-6),

5.13 (1H, d, J = 8.0 Hz, H-1''),

3.85 (dd, J = 3.2, 2.0 Hz, H-4''),

3.82 (dd, J = 8.0, 7.8 Hz, H-2''),

3.65 (dd, J = 11.0, 3.2, H-6''a),3.56 (dd, J = 11.0, 5.5 Hz, H-6''b),

3.58 (dd, J = 7.8, 2.0 Hz, H-3'')

3.48 (m, H-5)

OH


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Compound 4

m.p. 230-232 oC;

UV (MeOH) max: 207, 256 nm; neg. FAB/MS

m/z: 463 [M-H], 447, 423, 389, 297, 204;IR (KBr) max 3400, 2919, 1656, 1606, 1508

cm1;


7.70 (1H, d, J = 2.4 Hz, H-2'),

7.55 (1H, dd, J = 2.4, 8.6 Hz, H-6'),

6.85 (1H, d, J = 8.6 Hz, H-5'),6.34 (1H, d, J = 2.0 Hz, H-8),

6.16 (1H, d, J = 2.0 Hz, H-6),

5.22 (1H, d, J = 7.2 Hz, H-1''),

3.22~3.51 (4H, m, H-2'', 3'', 4'', 5''),

3.71 (1H, dd, J = 12.0, 2.4 Hz, H-6a''),

3.58 (1H, dd, J = 12.0, 5.2 Hz, H-6b'');

OH


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Result and Discussion

Compound 1: Kaempferol examined as an inhibitor of

cigarette smoke-induced activation of the aryl

hydrocarbon receptor and cell transformation

Compound 2: Astragalin (kaempferol-3-O--

Dglucopyranoside) , had cytotoxicity against four

human cancer cell lines

Compound 3: Hyperin (quercetin-3-O--D-

galactopyranoside) was reported to be a source ofantiretroviral for AIDS therapy due to significant anti-

HIV-1 activity

Compound 4: Isoquercitrin (quercetin-3-O--D-

glucopyranoside) has also been found to be a major

factor in anti-inflammatory and hepatoprotective

activity All the isolated flavonoids have been reported to

exhibit antioxidant activity


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CHORISMIC ACID

SHIKIMIC ACID

PREPHENIC

ACID

TYROSINE

PHENYLALANINE

CINNAMIC

ACIDS

ALKALOIDS ALKALOIDS

PHENYL-C3

COMPOUNDS

ANTHRANILIC

ACID

TRYPTOPHAN

ALKALOIDS

Shikimate

Pathways

PHENYL-C1

COMPOUNDS

FLAVONOIDS

(+ acetogenin piece)

NEXTLECTURE


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Biosynthesis


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Biosynthesis

NatPro - Isolation of Flavonoids From the Fruits of Cornus Kousa Burg

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Transcript of NatPro - Isolation of Flavonoids From the Fruits of Cornus Kousa Burg