Isolation of Chemical Compounds from xBrassicoraphanus

38(4) : 403 408 (2007)

403

배무채 ( × Brassicoraphanus ) ^{의 화학성분 분리}

이연희¹·안규석¹·이수성²·박영두³·유시용⁴·김성훈¹*

1경희대학교한의과대학

,

²중앙대학교창업보육센터바이오브리딩

,

³경희대학교원예학과

,

⁴한국화학연구원

Isolation of Chemical Compounds from x Brassicoraphanus

Yun-Hee Rhee

¹

, Kyoo-Seok Ahn

¹

, Soo-Seong Lee

²

, Young-Doo Park

³

, Shi-Yong Ryu

⁴

and Sung-Hoon Kim

^1*

1

Oriental Medical College, Kyunghee University, Seoul 130-701

2

BBI, Business Incubator Center, Chungang University Ansan 456-756

3

Department of Horticultural Biotechnology, Kyunghee University 449-70

4

Korea Research Institute of Chemical Technology, Daejeon 305-764

Abstract

−

xBrassicoraphanus is an intergenic breed crossed between Brassica campetris L. ssp. pekinensis and Raphanus sati- vus L. that have been daily consumed. x Brassicoraphanus was known to have good tastes and biological activities. Nev- ertheless, its constituetnts were not elucidated yet. Thus, in the present study, to indirectly evaluate the biological activity of xBrassicoraphanus , 12 compounds were isolated from leaves and roots of xBrassicoraphanus . On the basis of spectroscopic evidences, the structures of these compounds isolated from leaves of xBrassicoraphanus . were identified as

β

-sitosterol, indole- 3-acetonitrile, ferulic acid, methyl ferulate, linolenic acid methyl ester, linolenic acid and coniferyl alcohol, while the chemical structures of compounds isolated from the roots of were xBrassicoraphanus were characterized as

β

-sitosterol, indole-3-ace- tonitrile, ferulic acid, methyl ferulate, linolenic acid methyl ester, 1-methoxyindole-3-acetonitrile, goitrin, 4-hydroxycinnamyl alcohol, coniferyl alcohol, palmitic acid and daucosterol. These can be classified as three steroids, two indole cyanides, two cin- namic acid derivatives, one cinnamyl alcohol derivative, three fatty acid derivatives one isothiocyanate. These results suggest that the compounds isolated from xBrassicoraphanus were almost identical with known components of Brassica campetris L.

ssp pekinensis or Raphanus sativus L. However, it is necessary to investigate more about the difference of amounts of con- stituents according to harvest time and variant species amounts.

Key words

−

xBrassicoraphanus , Steroid, Indole, Cinnamic acid, Fatty acid, Isothiocyanate

배추

( Brassica campestris L. ssp. pekinensis [Lour.] Rupr.)

는십자화과

(Cruciferae)

^{에속하는두해살이풀로써}

,

^영어명

은

Chinese cabbage,

^또는

Celery cabbage,

^{중국명은菜}

,

^白

菜

,

^大白菜로

,

^{우리나라에서는숭}

,

^숭채

,

^백숭

,

^백채

,

^배추

,

배차

,

^{배채등으로불리우고있다}

.

¹⁾

원산지는중국북부지방이나그기원은지중해연안에자 생하는잡초성의유채

(

^油菜

)

^{라고전해지고있다}

.

^지중해

,

^중

앙아시아지역을거쳐서중국에전파되었고그후

7

^세기

경 중국 북부지방에서 재배되고 있던 순무

( Brassica campestris L. ssp. rapa Metzg : turnip,

^蕪菁

,

^蔓菁

)

^와남부

지방에서재배되고있던숭

(

^某

)

^{이자연교잡되어배추의원}

시형이나타났고이후

16

^{세기에반결구배추}

, 18

^{세기에결구}

배추로발전되어왔다

.

^{순무는배추와마찬가지로십자화과}

(

^배추과

; Cruciferae)

^{에속하는두해살이풀로서뿌리와잎을}

식용하는채소이다

.

^{1,2)원산지는중앙아시아와유럽남부지}

방이며기원은배추와마찬가지로지중해연안에자생하는 유채

(

^油菜

, Brassica campestris L)

^{라고알려져있다}

.

^현재

우리나라에서는강화도등지에서특산물로널리재배되고 있으며주로김치의원료로활용되고있다

.

^3,4)

한편

,

^배무채

( xBrassicaraphanus )

^{는무와배추의교배와}

약배양을통해육성된새로운속간식물이다

. ‘

^배무채

’

^는배

추와무의염색체를모두가지고있고

, 90

^{일이상재배하면}

배추와같이통이앉으며속잎이노랗고소형무정도비대 한뿌리를가지는특성이있다

. ‘

^배무채

’

^{는저온장일에서}

꽃눈이형성되고고온장일에서추대되므로봄과여름에는 성숙식물체재배가어려우나열무와같이이용할경우재

*교신저자(E-mail):[email protected] (FAX):02-964-1074

배가가능하여무가온시설이나노지에서는겨울을제외한 연중재배가가능하다

.

^또한

‘

^배무채

’

^의맛은무

,

^배추와다

른매운맛이나며김치를담그면중륵부분에수분함량이 많아시원하면서아삭아삭하여김치재료로사용이가능하 다고알려져있다

.

⁵⁾

이와같이동일한기원을가지고있는배추및무우등이 우리식단에서빼놓을수없는중요한식품소재임에도불구 하고이들식물들의화학성분에대한연구로는최근본연 구진에의하여이들식물의화학성분특히

dichloromethane

및

ethyl acetate

^{가용성분군에대한 성분연구4,6) 외에는미}

진한실정이다

.

^{이에본연구진은교배종인배무채의성분}

연구를배추와비교하여함유성분의차이점을살펴보고자 하였다

.

재료 및 방법

시약 및 기기 −본연구에사용된시약은모두특급

(GR)

및

1

^급

(EP)

^{급시약을사용하였으며지방산표준품은}

Aldrich

사로부터구입하였다

.

^융점은

Haakebuchler

^{미량융점측정}

기를이용하여측정하였으며측정치는따로보정하지아니 하였다

.

^선광도

[

^α

]

D는

JASCO DIP-4 digital polarimeter

^를

Low resolution MS (70 eV)

^는

JEOL

^사의

JMS-DX 303 mass spectrometer,

^각종

proton

^및

carbon NMR spectra

^는

Bruker

^의

AM-300

^및

AMX-500

^{을이용하여측정하였다}

. Column chromatography

^는

silica gel (70-230 mesh, Merck), Lichroprep RP-18 (40-63u, Merck)

^{를사용하였으며}

preparative TLC

^는

Kiesel gel 60 F plate (0.5 mm, Merck)

를사용하였다

.

실험재료 −실험에사용된배무채는중앙대학교안성캠 퍼스 바이오브리딩

(

^주

)

^{에서공급받은배무채의지상부와}

지하부를따로따로분리하여음건시킨후실험에사용하였 으며

voucher specimen

^{은경희대학교한의과대학병리학교}

실에보관되어있다

.

추출 및 용매분획 −뿌리부분을제거한배무채의지상부

(

^습중량

100 kg)

^{를일주일간음건한후건조시료를}

5

^일동

안

MeOH

^{에냉침시켰다}

.

^{냉침액을감압농축하여조}

MeOH

추출물

1,800 g

^을얻었다

.

^이

MeOH

^추출물을

20 L

^의증류

수에현탁시킨후분액여두에서동량의

EtOAc

^{로수차례추}

출하여

EtOAc

^가용분획

18 g

^을얻었다

.

^{잔류수층은}

BuOH

로추출하여

BuOH

^가용분획

16 g

^을얻었다

.

⁷⁾

또

,

^습중량

50 kg

^{의뿌리부분을따로잘게썰어일주일간}

음건한후

5

^일동안

MeOH

^{에냉침시켰다}

.

^{냉침액을감압농}

축하여

MeOH

^추출물

920 g

^을얻었다

.

^이

MeOH

^엑스를

같은요령으로

10 L

^{의증류수에현탁시킨후분액여두에넣}

고동량의

EtOAc

^{로수차례추출하여}

EtOAc

^가용분획

4 g

을얻었다

.

^{잔류수층은}

BuOH

^{로추출하여}

BuOH

^가용분

획

19 g

^을얻었다

.

배무채 지상부 EtOAc 용매분획으로부터 함유성분의 분

리 −배무채지상부

MeOH

^{추출물을전술한방법에준하}

여용매분획한

EtOAc

^가용분획

10 g

^을취하여

n -hex/EtOAc

=4:1, 3:1, 2:1, 1:1, EtOAc, 50% CH

2

Cl

2

/ MeOH

^의용출

용매 순으로

silica gel (70-230 mesh, 750 g) column (Ø=5.0

^×

100 cm) chromatography

^{를실시하여}

Fr. 1 (0.8 g), Fr. 2 (1.8 g), Fr. 3 (2.7 g), Fr. 4 (2.4 g)

^및

Fr. 5 (4.9 g)

^등

총

5

^{개의분획으로나누었다}

.

^그중

Fr. 2

^으로부터

120 mg

의무색침상결정이석출되었다

(

^화합물1

). Fr. 3

^은용출

용매

;CH

2

Cl

2

:MeOH 100:1, 50:1, 10:1, 1:1

^{를사용하여}

재차

silica gel column chromatography

^{를실시하여총}

5

^개

의소분획

(Fr. 31-Fr. 35)

^{으로나누었다}

.

^이중

Fr. 31

^을다시

40% MeOH

^{을 용출용매로 하여}

RP-18 column

chromatography

^{를실시하여화합물 2}

(10 mg)

^{과화합물 4}

(16 mg)

^{을각각분리하였다}

. Fr. 32 (56 mg)

^를

50% MeOH

을용출용매로하여

RP-18 column chromatography

^를실시

하여

20 mg

^{의무색침상결정}

(

^{화합물 3}

)

^{을분리하였다}

. Fr.

34 (580 mg)

^를

RP-18 column chromatography

^{를실시하여}

240 mg

^의

oil

^{상물질화합물 5를분리하였다}

.

배무채 지하부 EtOAc 용매분획으로부터 함유성분의 분

리 −배무채지하부

MeOH

^{추출물을전술한방법에준하}

여용매분획한

EtOAc

^가용분획

EtOAc

^층

4 g

^을

n -hexane/

EtOAc

^{혼합용매를용출용매로사용하여기울기용리방식}

으로

silica gel column chromatography

^{를실시하여}

Fr. 1- Fr. 8

^등총

8

^{개의분획으로나누었다}

.

^이중

Fr. 1

^로부터

oil

상태의 화합물 5

(1.2 g)

^{을 분리하였다}

.

^한편

Fr. 2

^를

n - hexane/EtOAc

^{혼합용매에방치한결과}

14 mg

^{의무색분말}

이석출되었다

(

^{화합물 11}

).

^또

, Fr. 3

^을

MeOH

^{에녹여방치}

한결과무색침상결정화합물 1

(23 mg)

^{이석출되었다}

.

^화

합물 1을 여과하고 남은 결정여액은

RP-18 column chromatography (

^용출용매

:MeOH in water

^{기울기용리방식}

)

를실시하여

Fr. 321, Fr. 322, Fr. 323

^{으로나누었으며}

Fr.

322

^으로부터

7 mg

^{의화합물7을분리하였다}

.

^또

,

^같은방법

으로

Fr. 5

^를

RP-18 column chromatography (

^용출용매

: MeOH in water

^{기울기용리방식}

)

^{를시행하여}

6

^{개의소분획}

(Fr. 51-Fr. 56)

^{으로나누었다}

.

^이중

Fr. 53

^{에서화합물2}

(4 mg)

^과

Fr. 55

^{에서화합물 6}

(110 mg)

^{을분리하였다}

.

한편

Fr. 6 (0.9 g)

^을

MCI gel column chromatography (

^용

출용매

:MeOH in water

^{기울기용리방식}

)

^{를실시한결과화}

합물 8

(22 mg),

^{화합물 9}

(8 mg)

^{및화합물10}

(4 mg)

^을얻

었다

.

^또한

Fr. 7 (8 g)

^을

RP-18 column chromatography (

^용

출용매

: MeOH in water

^{기울기용리방식}

)

^및

silica gel column chromatography

^{를반복실시한결과무색분말화합}

물 12

(45 mg)

^을얻었다

.

Compound

^{1 무색침상결정}

(MeOH), mp. 140

^o

C,

C

29

H

50

O, EIMS m/z; M

⁺

: 414.72, [

^α

]

D

=

⁻

37

^o

(c 0.1 CHCl

3

),

¹

H-NMR (300 MHz, CDCl

3

) :

^δ

5.32 (1H, m, H- 6), 3.49 (1H, m, H-3), 0.98 (3H, s, H-19), 0.89 (3H, d, J

=6.5 Hz, H-21), 0.64 (3H, s, H-18).

¹³

C-NMR (125 MHz, CDCl

3

) :

^δ

11.8 (C-29), 11.9 (C-18), 18.8 (C-21), 19.0 (C-27), 19.4 (C-19), 19.8 (C-26), 21.1 (C-11), 23.0 (C-28), 24.3 (C-15), 26.3 (C-23), 28.2 (C-16), 29.1 (C-25), 31.6 (C-2), 31.8 (C-8), 31.9 (C-7), 33.9 (C-22), 36.1 (C-20), 36.5 (C-10), 37.2 (C-1), 39.7 (C-12), 42.3 (C-4), 45.8 (C- 13), 50.1 (C-24), 56.0 (C-9), 56.1 (C-17), 56.7 (C-14), 71.8 (C-3), 121.7 (C-6), 140.7 (C-5)

Compound

²

White powder, mp 37

^o

C, C

10

H

8

N

2, 1

H- NMR (300 MHz, CDCl

3

) :

^δ

8.35 (1H, brs, NH), 7.52 (1H, d, J =7.9 Hz), 7.38 (1H, d, J =7.9 Hz), 7.15 (2H, m, H-5,6), 7.12 (1H, s, H-2), 3.78 (2H, s, H-10).

¹³

C-NMR (125 MHz, CDCl

3

) :

^δ

14.4 (C-10), 104.8 (C-3), 111.5, 118.1 (CN), 120.3 (

^×

2), 122.9, 123.2, 125.9 (C-9), 136.3 (C-8)

Compound

³

mp. 174

^o

C, C

10

H

10

O

4, 13

C-NMR (125 MHz, (CD

3

)

2

CO- d

₆

) :

^δ

127.7, 110.5, 147.1, 146.4, 115.3, 121.9, 141.3, 121.1, 175.8, 55.6.

Compound

⁴

mp. 63

^o

C, C

11

H

12

O

4, 1

H-NMR (300 MHz, CDCl

3

) :

^δ

7.55 (1H, d, J =15.9 Hz, H-7), 7.19 (1H, d, J

=2.4 Hz, H-2), 6.99 (1H, dd, J =8.1, 2.4 Hz, H-6), 6.84 (1H, d, J =8.1 Hz, H-5), 6.22 (1H, d, J = 15.9 Hz, H-8), 3.86 (3H, s, -OCH

3

), 3.72 (3H, s, -OCH

3

)

Compound

⁵

colorless oil, C

21

H

36

O

4, 1

H-NMR (300 MHz, CDCl

3

) :

^δ

0.99 (3H, t, H-18'), 1.33 (8H, m), 1.65 (2H, m, H-3'), 2.09 (4H, m, H-8',17'), 2.36 (2H, t, H-2'), 2.82 (4H, m, H-11',14'), 3.68 (2H, m, H-3), 3.95 (1H, m, H-2), 4.19 (2H, m, H-1), 5.38 (6H, m, H-9',10',12', 13',15',16'),

¹³

C-NMR (125 MHz, CDCl

3

) :

^δ

14.2 (C-18'), 20.5 (C-17'), 24.8, 25.5, 25.6, 27.2, 29.0 (

^×

2), 29.1, 29.5, 34.1, 63.6 (C-1), 65.1 (C-3), 70.2 (C-2), 127.1, 127.7, 128.2, 128.3, 130.2, 131.9, 174.3 (C=O)

Compound

⁶

colorless oil, C

19

H

34

O

2

,

¹

H-NMR (300 MHz, CDCl

3

)

^δ

: 0.90 (3H, t, terminal -CH

3

), 1.20 ((CH

2

)

n

, m), 1.54 (2H, m), 1.98 (4H, m), 2.22 (2H, t), 2.74 (2H, m), 3.59 (3H, OCH

3

), 5.30 (4H, m, H-olefinic protons)

Compound

⁷

C

11

H

10

N

2

O,

¹

H-NMR (300 MHz, CDCl

3

)

δ

: 3.69 (2H, s, H-10), 3.98 (3H, s, -OCH

3

), 7.08 (1H, m), 7.18(1H, s, H-2), 7.21 (1H, m), 7.37 (1H, d, J =7.8 Hz), 7.47 (1H, d, J =7.8 Hz)

¹³

C-NMR (125 MHz, CDCl

3

)

^δ

: 14.2 (C-10), 66.0 (OCH

3

), 100.2 (C-3), 108.5, 117.8 (CN), 118.2, 120.3, 121.6, 122.3, 123.1, 132.2.

Compound

^{8 무색분말}

, mp 50

^o

C, C

5

H

7

NOS,

¹

H-NMR (300 MHz, CDCl

3

)

^δ

: 3.46 (1H, dd, J =9.6, 9.6 Hz, H-4a), 3.85 (1H, dd, J =9.6, 9.6 Hz, H-4b), 5.31 (3H, m, H-2', 5), 5.91 (1H, m, H-1'), 7.60 (1H, brs, NH)

¹³

C-NMR (125 MHz, CDCl

3

)

^δ

: 49.1(C-4), 83.7(C-5), 120.5(C-2'), 132.9(C-1'), 189.5(C-2).

Compound

⁹

C

9

H

11

O

2

,

¹

H-NMR (300 MHz, CDCl

3

)

^δ

: 4.07 (2H, d, J = 5.0 Hz, H-3'), 6.15 (1H, m, H-2'), 6.42 (1H, d, J =15.9 Hz, H-1'), 6.70 (2H, d, J =8.4 Hz, H-3,5), 7.23 (2H, d, J =8.4 Hz, H-2,6)

Compound

^{10 무색분말}

, mp 74-75

^o

C, C

10

H

12

O

3

,

¹

H- NMR (300 MHz, CDCl

3

)

^δ

: 3.81 (3H, s, OCH

3

), 4.22 (2H, d, J =6Hz, H-3'), 6.15 (1H, m, H-2'), 6.45 (1H, d, J

= 15.9 Hz, H-1'), 6.81 (3H, m, aromatic H).

Compound

^{11 무정형분말}

, mp 63-64

^o

C C

16

H

32

O

2 1

H- NMR (300 MHz, CDCl

3

)

^δ

: 0.83 (3H, t, terminal -CH

3

), 1.18 ((CH

2

)

n

, m), 1.58 (2H, m), 2.30 (2H, t)

Compound

^{12무색분말}

, mp 270~272

^o

C, C

35

H

60

O

6

,

¹

H- NMR (300 MHz, DMSO- d

₆

)

^δ

: 0.83 (3H, s, H-18), 0.99 (3H, s, H-19), 4.40 (1H, d, J =7.7 Hz, anomeric H), 5.52 (1H, m, H-6).

결과 및 고찰

배무채의지상부

(100 Kg)

^와지하부

(50 Kg)

^{를따로따로}

음건한후

MeOH

^로

5

^{일간상온에서각각추출한결과배무}

채의지상부의경우

1,800 g,

^{지하부의경우}

920 g

^의

MeOH

추출물을얻었으며수득율은지상부및지하부모두원시료

의습중량대비

1.8%

^{정도로나타나배추의경우}

(

^습중량

대비

1.0%)

^{와비슷한결과를얻을수있었다}

.

^{배무채의지}

상부 및지하부의 함수율을 약

90%

^{로가정하였을경우}

MeOH

^{추출물의수득율은각각약}

18%

^{정도인것으로나}

타났다

.

이지상부

MeOH

^{추출물을통상의방법에따라증류수}

에현탁시킨후

EtOAc, BuOH

^{순으로용매분획하여본결}

과원시료습중량대비

0.018%

^의

EtOAc

^가용분획

(18 g)

^과

원시료습중량대비

0.016%

^의

BuOH

^가용분획

(16 g)

^을얻

었다

.

^즉

,

^{배무채지상부}

MeOH

^{추출물을통상의방법에따}

라용매분획을실시할경우추출물의

98%

^{이상이모두최}

종수층에잔류되는점으로보아배무채지상부는거의대

부분

(98%

^이상

)

^{이탄수화물등수용성물질들로구성되어}

져있음을짐작할수있으며유기용매에이행되는지용성

성분군은원시료중량대비

0.05%

^{미만으로극히소량만이}

존재함을알수있었다

.

지하부

MeOH

^{추출물도같은요령으로증류수에현탁시}

킨후

EtOAc, BuOH

^{순으로용매분획하여본결과원시료}

습중량대비

0.009%

^의

EtOAc

^가용분획

(4 g)

^{과원시료습}

중량 대비

0.038%

^의

BuOH

^가용분획

(19 g)

^을얻었다

.

^따

라서배무채지하부

MeOH

^{추출물의경우에도추출물의거}

의대부분

(98%

^이상

)

^{이탄수화물등수용성물질들로구}

성되어져있으며유기용매에이행되는지용성성분군은아 주소량이었다

.

한편배무채의지상부와지하부의

MeOH

^{추출물을전술}

한방법에따라용매분획하여얻어진

EtOAc

^{분획물각각}

으로부터함유성분의분리를시도하기에앞서

EtOAc

^분획

물들의

TLC

^{를실행하여}

TLC pattern

^및

profile

^을배무추

지상부및지하부와배추의

EtOAc

^{분획물의그것들과비}

교하여보았다

. (Fig 1).

그결과로보아 배무채지상부의경우에는

TLC pattern

이배추지상부의

TLC pattern

^{과거의비슷하나더다른성}

분을함유하고잇는것으로보이며

,

^{지하부의경우도배추}

와다른

TLC pattern

^을보였다

(Fig 1).

^따라서

Fig 1

^에서

관찰된

TLC pattern

^{의소견으로보아배추의지상부에존}

재하는대부분의성분들을배무채의지상부는모두함유하 면서배무채의지하부도지상부와다른여러성분을함유하 고있음을알수있었다

.

^{결론적으로배추와무의교잡으로}

만들어진배무채는배추에비해 지용성성분들의경우에 는대체로비슷하지만보다다양한성분의종류및함량이 있을것으로추정된다

.

한편배추의경우와동일한방법으로배무채지상부의지 용성성분군즉

EtOAc

^{가용분획을}

Scheme. 1

^{과같은방식}

으로

silica gel column chromatography

^와

RP-18 column chromatography

^{를반복적으로실시하여정제한결과}

2

^종의

steroid

^계화합물

(

¹

,

⁶

), 1

^종의

indole

^계

cyanide

^화합물

(

²

), phenylpropanoid

^에속하는

2

^종의

cinnamic acid

^유도체

(

³

,

4

)

^{및다량의지방산}

linolenic acid (

¹⁰

)

^{및그유도체}

(

⁵

)

^등

총

6

^{종의화합물을순수분리하였다}

(Scheme. 2).

또

,

^{동일한방법으로배무채지하부의지용성성분군즉}

EtOAc

^{가용분획을}

Scheme. 2

^{과 같은방식으로}

silica gel column chromatography, RP-18 column chromatography

^를

반복적으로실시한결과

isothiocyanate

^화합물

1

^종

(

⁸

), 2

^종

의

steroid

^계화합물

(

¹

,

¹²

), 2

^종의

indole

^계

cyanide

^화합물

(

²

,

⁷

), 2

^종의

cinnamic acid

^유도체

(

³

,

⁴

), 1

^종의

cinnamyl alcohol

^유도체

(

⁹

)

^및

3

^{종의지방산및그유도체}

(

⁵

,

¹⁰

,

11

)

^등총

10

^{종의화합물을분리하였다}

.

^특히

EtOAc

^가용

분획의경우절반이상이

linoleic acid

^{등지방산혹은지방}

산유도체로구성되고있음을알수있었다

.

^8,9)

배무채지상부및지하부의

EtOAc

^{가용분획으로부터분}

리된각화합물들은각각의물리화학적성상

,

¹

H-NMR

^및

13

C-NMR spectral data

^{를종합검토하고10)기존의관련실험}

을비교하여본결과

,

^{4,11)이들은각각 β}

-sitosterol (

¹

), indole- 3-acetonitrile (

²

), ferulic acid (

³

), methyl ferulate (

⁴

), linolenic acid methyl ester (

⁵

), linolenic acid (

⁶

), 1- methoxyindole-3-acetonitrile (

⁷

), goitrin (

⁸

), 4-hydroxy- cinnamyl alcohol (

⁹

), coniferyl alcohol (

¹⁰

), palmitic acid (

¹¹

)

^및

daucosterol (

¹²

)

^{로동정할수있었다}

. (Fig. 2)

이중β

-sitosterol (

¹

)

^및

daucosterol (

¹²

)

^{은배추를비롯}

한십자화과식물및여러초본식물에광범위하게존재하

Fig 1. SiO

2

TLC profile of the EtOAc fractions of xBrassicoraphanus developing solvent: n -hexane/EtOAc=1:1, detection: H

2

SO

4

Scheme. 1. Isolation of compounds 1 ~ 5 from the MeOH extract of the aerial part of xBrassicoraphanus.

Scheme. 2. Isolation of compounds from the MeOH extract of

the underground part of xBrassicoraphanus.

는대표적인식물

steroid

^{화합물로서식물성장에필수적으}

로요구되는성분이며항암활성및고지혈증의개선등의 약리효능이보고되고있다

.

^또

,

^화합물

indole-3-acetonitrile (

²

)

^및

1-methoxyindole-3-acetonitrile (

⁷

)

^{는배추및십자화}

과채소류에널리 함유된유기황배당체화합물

(glucosi- nolate)

^{의분해산물로서}

glucosinolate

^{가추출도중유기용매}

에의하여혹은식물세포에존재하는효소인

myrosinase

^의

작용에의하여분해된

nitrile

^{산물로서항암활성및식물성}

장호르몬으로작용한다고알려져있다

.

^또

, goitrin (5-vinyl-

2-thiooxazolidone)

^역시

glucosinolate

^{가 유기용매 혹은}

myrosinase

^{의작용에의하여분해된}

isothiocyanate

^화합물

의유도체로서순무의쓴맛을나타내는성분의일종으로서 항균작용을나타낸다고보고되고있다

.

^12)또

, ferulic acid (

³

), 4-hydroxy-3-methoxycinnamic acid methyl ester (methyl ferulate,

⁴

)

^는

sinapic acid methyl ester

^와함께십

자화과식물에널리 분포하는

phenolic acid

^{계성분으로서}

항암활성

,

^{항산화작용}

,

^{소염작용등다양한생리활성을나}

타내는성분으로알려져있다

.

^한편

, linolenic acid methyl

Fig. 2. Structure of compounds 1 ~ 12 isolated from the extract of xBrassicoraphanus.

ester (

⁵

)

^{는십자화과식물및여러식물에서분리보고되고}

있으며특히배추에서는지방산중

linolenic acid

^가풍부하

게함유되어있다고보고되고있다

.

¹³⁾

한편배무채지상부및지하부의

MeOH

^{추출물중추출}

물의총중량의대부분을차지하고있으며

EtOAc, BuOH

^등

유기용매분획으로이행되지않고최종수층에잔류되는분 획에대하여는별도로성분연구를시행하여본결과대부 분의성분들이단당류

(glucose), 2

^당류

(maltose)

^및다당류

등탄소화물군과미확인

phenolic polymer

^{등으로구성되}

고있음을알수있었다

.

^{그러나배무채의구성성분의함량}

은배추나무가가지고있는함량차이가있을것으로사료 되며

,

^{배무채의새로운품종과채취시기에따른함량차이}

연구도필요할것으로사료된다

.

결 론

본연구의대상인배무채는우리식단에서다용되는배추 와무우간의속간잡종으로그맛과생리활성이비교적우 수하나그에대한성분연구는아직이루어지지않았다

.

^따

라서본연구에서는배무채의생리활성을간접적으로평가 하기 위한 일환으로

,

^{배무채지상부와 지하부로부터 β}

- sitosterol, indole-3-acetonitrile, ferulic acid, methyl ferulate, linolenic acid methyl ester, 1-methoxyindole-3-acetonitrile , goitrin, 4-hydroxycinnamyl alcohol, coniferyl alcohol, palmitic acid and daucosterol

^등총

12

^{종의성분을분리하}

여보고하는바이다

.

^{이상의성분으로보아배무채는배추}

와무우에서이미알려진성분을대체로함유하고있는것 으로보이나

,

^{그변종과채취시기에따른함량의차이의연}

구도필요할것으로사료된다

.

감사의 글

본연구는바이오그린

21

^{연구비지원에수행되었는바}

감사드립니다

.

인용문헌

1. Lee J.M. (2003) Vegetable Horticultures. Hynagmunsa. 324- 347.

2. Park K.W., Ryu K.O. (2000) Functional Vegetables. Herb World Press . 131.

3. Cheigh H.S., Park K.Y, (1994) Biochemical, morphological, and nutritional aspects of kimchi (korean fermaented veg- etable products). Critical Reviews in Food Science and Nutrition 34 (2): 175-203.

4. Choi Y.H., Kim J.S., Seo J.H., Lee J.W., Kim Y.S., Ryu S.Y., Lee K.R., Kim Y.K., Kim S.H. (2004) Chemical constituents of Brassica campetris ssp pekinensis . Kor J Pharmacogn.

35 (3): 255-258.

5. Lee S.S. (1999) Breeding a fertile intergeneric allotetraploid plant between heading Chinese cabbage and korean radish.

Kor J Hort Sci Technol. 10 : 653.

6. Ahuja K.L., Batta S.K., Raheja R.K., Labana K.S., Gupta M.L. (1989) Oil content and fatty acid composition of prom- ising Indian Brassica campestris L. (Toria) genotypes. Plant Foods Hum Nutr. 39 (2): 155-160.

7. Dias C., Dias M., Borges C., Almoster Ferreira M.A., Paulo A., Nascimento J. (2003) Structural elucidation of natural 2- hydroxy di- and tricarboxylic acids and esters, phenylpro- panoid esters and a flavonoid from Autonoë madeirensis using gas chromatographic/electron ionization, electrospray ionization and tandem mass spectrometric techniques. J Mass Spectrometry 38 (12): 1240-1244.

8. Chowdhury B.K. and Chakraborty D.P. (1971) 3-formylin- dole from Murraya exotica. Phytochemistry 10: 481-483.

9. Harrison L.J., Sia G.L., Sim K.Y., Tan H.T., Connolly J.D., Lavaud C., Massiot G. (1995) A ferulic acid ester of sucrose and other constituents of Bhesa paniculata. Phytochemistry 38 (6): 1497-1500.

10. Pouchert C. (2004) Aldrich Library of

¹³

C and

¹

H FT NMR Spectra, 3, 136A, 136B, 153C.

11. Kim J.S., Choi Y.H., Seo J.H., Lee J.W., Kim Y.S., Ryu S.Y., Kang J.S., Kim Y.K., Kim S.H. (2004) Chemical constituents of Brassica campetris ssp rapa . Kor J Pharmacogn . 35 (3):

259-263.

12. Kenji M., Mitsuo T., Akira S. (1995) Three sulphur-con- taining stress metabolites from Japanese radish. Phytochem- istry 39 : 581-586.

13. Loub W. D., Wattenberg L. W., Davis D. W. (1975) Aryl hydrocarbon hydroxylase induction in rat tissues by naturally occurring indoles of cruciferous plants. J Natl Cancer Inst.

54 (4): 985-988.

(2007

년

12

월

5

일 접수

)