88

Nippon Shokuhin Kagaku Kogaku Kaishi Vol. /2, No. -, 22*30 (,*++) +,

 16 



¯ ° ±². ³´. µ ¶ ·{*N2¸W** O¹º** »¼.P Q½R
?/@AB?
* C D!
** CEFGHIJKRadical Scavenging Activity of Polyphenols in Young Leaves of Sesamum indicum L.
Hiroshi Matsufuji, Junichi Ohmori, Shuichi Goto, Makoto Chino, Etsuji Wada*,
Ayumi Uchida**, Katsunori Fukahori**, Kazuo Yamagata and Hidetoshi Sakurai
College of Bioresource Sciences, Nihon University, +200 Kameino, Fujisawa, Kanagawa ,/,ῌ*22** Wadaman Co. Ltd., 1ῌ31 Oihara, Yao, Osaka /2+ῌ**3,** Wadaman Science Co., Ltd., /.0 Karasumaoike Agaru, Nijoden-cho, Nakagyo-ku, Kyoto 0*.ῌ*2./῎῎῎῎῎῎῎῎῎῎῎῎῎῎῎῎Antioxidant activities of young sesame leaves (Sesamum indicum L.) were measured using - di#erent
radical scavenging methods (DPPH, ABTS, and superoxide anion radicals). The activities of young sesame
leaves in any of the methods were higher than those of barley and kale, while mulberry leaves had thehighest activity. The activities were dependent on the polyphenol content in samples (mulberry, +/.3 ;sesame, 3.-3 ; kale, -.0+ ; barley, ,.*. mg-gallic acid equivalent/g-dry weight). However, when antioxidant
activities per weight of polyphenol were estimated, the young sesame leaves showed the same or higher
antioxidant activity than mulberry leaves, suggesting that young sesame leaves would contain strong
antioxidative phenolic compounds. Next, when young sesame leaf extract was applied to an HPLC-DPPH
online post-column system, nine peaks (S+*S3) appeared in the UV chromatogram at -.* nm, and HPLCseparated components corresponding to peaks S., S/, S0 and S2 reacted with DPPH. This result suggeststhat these are the major antioxidative components in young sesame leaves. From the results of several
chromatographic puriﬁcations, about +.. kg of young sesame leaf powder yielded /,. mg of compound S/.
The MS and NMR analyses revealed that S/ was acteoside, a phenylpropanoid glycoside. The acteosidecontent in young sesame leaf powder was +.,῍.
(Received Sep. ,,, ,*+* ; Accepted Nov. ,0, ,*+*)
Keywords : sesame, DPPH radical, ABTS radical, superoxide anion radical, acteoside῍ῌ῏ῌ῎ :  DPPH  ABTS 



6B Pedaliaceae " Sesamum L"M 

NLO>:P# $QR %S

T UV &0(./0 Sesamum indicum L. 123 45 #W0X'L<=(()*ῌ+Y*89:<=: ,-0./Z[\./0]LO>:;<=:>>(,./- G^ *_10 L`(8 a2N2b03c(- ;d12( S. indicum efL -* gd0/dh2

hi489:>(8jklmM(nh2(o8N3 45 16.789:;ῌ<=:>(+,-p5Nqr0#Wl6s7tu8 vwxy 9 N:

6 z0dvh7;89:<=  dv N

y0{<L>[=:>(8<=:>(- |h}10

=6|h}07/~LO>:8:W>7;1>076 8H>h 0>h7;2(- 16 ?M(5@hALB&<= z89:B&l >Z0

0CND?Eh~%LE=:>( -FG89:H<=:>(--.' S. indicum N S. radiatum 0>6 45
,/,ῌ*22*  +200
* /2+ῌ**3, 
 ! 1ῌ31** 0*.ῌ*2./ " "#$%&'() /.0 Corresponding author hmatsufu@brs.nihon-u.ac.jp¡Z[>

0DIL`(8 >¢£FG6+** g 2^3 + -***+ 2** mg J7v¤KLM89: 0¥54¦§

l¨89:>(- 9Z9 >0¥54¦§

D0©ªL>:0«6¬>- *_10 L`(8 S. indicum 0¢£>6 *.-῍ 0­®5J

ῌ : K@LMN 17 

0FOPI8

0-hydroxy-luteolin 1-methyl ether

89-Q 9,#

0-glucoside +, pedalitin-0-O-glucoside -./012, 

#  !$ +30* " Moritaῌ

1

 S. indicum RHI!
45678 -

ῌ

STUV "39# +,$ Jain2 $%&

*9, S. indicum RHI!
"345678 -ῌST

DPPH 

DPPH

W"++ "#<X,# YEZ[$ \]^"\'(_ *., ml, +** mmolῌl Tris-HCl `)_ pH 1.. *.2+"UV

ml, *.,* mmol/l DPPH῏GHI(_ + ml -,a9$ +*9$ - *./῍ ./0-.bc9dSd/9,e$ f01g" -* 2b349"h9# 9S9E!T$ Ti56E78,# -* 2e$ 9j(_ /+1 nm "klm=: As - ,n$ o;2"pq:TS"

 9,# \'(_<Z4"GHI-,a9,=r

E# 8$ Konan T3 $ S. radiatum OsI

m= : -tuv09$ wx > ῌ STtu?$ 7yz ?$ OPI8 ?E{|7OsI

vm=: AC "@Y$ \',a;m=: AS-AB"./09!$ o;2ῌ.C"p}D~r$ YEZ[E ῍ -n,# Ek$ /*῍

FdTS"9E#  Hata T+* K@E-Y0\'G: HG: - IC/* 09I ;2097yz ?"JK9$ =n,#- L 29, : UPLC-FLD"34 S. indicum E῍%AC&ASῌAC'+**MBCD .-N# 9S9$ K@A((ῌ

 + g ,4BCD . *./,.0 ῌg  4$ OM09, Trolox : ;" -<$ IC/* +ῌ/ *** P:0nDE0-TS"9#Q-n$ \' Trolox R TEAC -wx>S6"$ |7OsI.C0LMNT῍ n,#! 4$ |7OsI.CUVLMN

TEAC%TroloxIC/*ῌgῌmlῌ\'IC/*ῌgῌml-Y# o$ W K@LMN- DPPH((῍$ ABTS $ 
  WST-+  - O8 "34XY00:"$ oYZ|7OsI;2-῍

ABTS 

ABTS

W"++ "#<X,# 1 mmolῌl ABTS [(_ / ml " +.* mmolῌl \M7 22 ῌl -a$ f0

TS"Y0-\,#]g" +,+0 ;b8u9,# (_-ABTS stock solution 09$ 1-. nm m=:! *.1)*.*,+ 

"E3F"GHIJ9$ - ABTS working

K@^_\'$ D @K@ S. indicum

solution 09,# \]^" ABTS working solution + ml

L. ,**1  0 ` ¡¢& ab- -*1* cm 34c-2d9$ o"\' +* ῌl -,a9$ +* .bc9dS

eT,£¤^¥V \V -¦9,# fg

d/9$ -**  . 2b8 u9,# oe$ 1-.

$ §$ ¨^_\'©>ªhijklm34

nm "klm=: As - 9,# \'(_<Z4

no9,# DPPH +, +-diphenyl-,-picrylhydrazyl i" 2*῍ GHI-,a9,=rm=:-t=>?$ ABTS ,, ,῎-azinobis --ethylbenzothiazo-

09,# p> ῌ 34$ t uvm=: Ac "@uv

line-0-sulphonic acid  Roche Diagnostics $ TroloxY$ \',a;m=: Ac }D~rSTE

0 -hydroxy- ,, /, 1, 2 -tertamethylchroman- , -carboxylic῍ -n,# oe$ \ ' "p p> ῍ 34acid  Aldrich $ SOD Assay-Kit WST  qN«TEAC -n$ oQ- ABTS 09,#0$ 

H¬ SOD ; EC. +. +/.

+. +.  r­®st  Sigma -¦9,# o\$ ¯uv°\-$ [ Milli-Q [-,#῎   SOSASOSA W"++ "# SOD Assay Kit-WST ¦8

-w±x9, WST-+"<X,# 30 ²@8³v´LMN!ynTG:-NY,n"$ K@

µu" ,* ῌl \'(_$ ,** ῌl  WST-W (_$ ,* ῌl$ fg$ §$ ¨^_\'o¶ ,./$ 1./$

 WST-E (_-z·,a9$ @8³v´µu76

1./$ +.- g -{9$ - .* ml  2*῍ GHI-a$ +/Sd/9,# WST-E (_,aST +* 2e"@8³v

2b|¸}~9,# ADVANTEC No. /C ¹e$ /*´µu76 ./* nm "klm=: As -ml "R º´9$ \'(_-N9,# (_-»

9,# \'<Z4"|[-,a9,¼m=:- Ab+$J9$ OLMN \'09,# Ek$ T

WST-E  < Z4" dilution buffer - , a9, = rm

w-G½|µHG9$ GHI-e$ V= : - Ab,$ WST-E  < Z4" dilution buffer - , aA9$ oST 2*῍ GHI!

9$ Sp\'<Z4" 2*῍ GHI-,a9,¼

_G:

HIJIKL  /2 M  - N ,*++  - O

90

 18 

PQ! Ab- ?#+ 9:3R ῌ SD!TU, 

g+ .*῍ V567 ./* ml W#+ E3 +/* ml #+ /*῍ 3D!XY?Z3

+ !G4[7 +/* ml+   ! IC/*?#TU,

]!^+

..ῌ

+,-.?#/^ SOD f0g!^+ IC/*
4!TU+ m

3 SOD 5no!9:3R . "TU

, t+ SOD  Milli-Q 6W#,

3IC/*mgῌml& : .*῍ V567+' 0 mlῌmin+ ()* / ml e#, hi1#2j3Ukl\ / @3]# Fr. +/Fr. /#p+ q3rs Fr. - +.*2 g ! .*῍ 4567 / ml %& : .*῍ 4567+' : ..* ml ῌ min, CA_u :.*0+ v89 : -.* nm+ ()* +/* ῌl e#, :..῍#!wxy#p 3 ]# : Fr. -῎+/Fr. -῎3+ 0;:"z{`7#7 HPLC SSC-+-**+ |}~HI !r- ῌ
2*῍ 45678;3z=67*=zῌ[C7*+, STU, Yts+

8 *./ ml ?=zῌ[C7* = *., m++ >^BCDG=  CA_ : Develosil Lop-ODS+ ,.-0* mm+ d%

W#+ #7 HPLC Inertsil ODS-- JET +*/* mm+ d

SOD5no-SOD3IC/*unitsῌmlῌ567]#!$ +1.+ g, ]#! .*῍

V567 ,** ml   W#+ ODS CA_`ab*cA

D῍-Ab+Ab,AsAb,
ῌAb+Ab-+**567 +/* ml \"#*z_8 *./ m + !EFy$%#q?S+ Fr. -῎, S:# S/ !<2# /,. mg,0

MS  NMR .*#? MS  Waters @, E36 ..- mL !$%#+ u" + g9GH

 ESI 

I#J#KL+ 10/ nm 3PQ!#,  FAB 

MG+,8!0NO#$v*Pxkz=,   NMR 

67* MG&Q* !TU,d. + ml W#+ .

DPPH on-line Quattro Premier !A

# UPLC-MS ῌ MS 4`*a
JMS-SX+*,A+* mg ! DMSO-d0    MeOHECA-/**  +H+ +-C+ mR

 DQF-COSY, NOESY, HMQC, TOCSY, HMBC

S3T+- !UV#, Yts+ bW!,3 2*῍ 45678 +/ mgῌml !+ 9:3;31 

HPLC e#, CA_ : X-bridgeTM C-+2 ..0+/* mm,bW /* mg  2*῍ 4567 /* ml !+/ ῌm, Waters+ X : /῍ |*(*z7 *.+῍ G!"#$+/ # 3 Y  8Z[ + *../ ῌ m =75"#+\ * #1-/῍ |*(*z7 *.+῍ G\ +/ #

HPLC

1+**῍ |*(*z7 *.+῍ G\ .* #+P r-*.3333 SbW;3` }*!

':*.2 mlῌmin, v89 : -.* nm, u : .*0+ ()* : +* ῌl.
HPLC 3 ^    - T B*! 7 S _ p+ ,***.0 mlῌmin " #$%#+0*0 " &,
DPPH ABC7?3%"$%#8!

'&'()* *.,/ mm+/ m,&8!89 /+1 nm v#+&`¡\¢

`!v#,

}3v*]f,% & ' (

mmolῌml MES <)=> pH 0.* ? *.+ mmolῌl DPPH῎|*(*z78! 2 : , 3?#, ///** ῌgῌml 3`+ #)*+,



3 2*῍ 45678! #+ E3FG

! - @3ABC7D DPPH ABC7D+ ABTS
ABC7D+ £¤}(ABC7D¥¦y WST-+  San#,b*3c^de/ -. #/0

E§"¨\©+ fgW+ ª7?bW3FG

,** g «¤{ /** ml !+ -* #3h!i¬#?q+ ­3FGo^f+ ®

?r!, q3 O ! , ¯^+ j °#, ^"±FG+ ©2bW2ª72fgW3"?

2*῍ 4567! /** ml + -* #h?r#+ t k +, qlk3FG

8!$, q3O! , ¯²Sl#+ $kl8

7*³´Y\?µklq?xk+ =zῌ[;3z=6

! +** ml "m#, q3O! 1 ¯²Sl#+ %¶C7*Sz=67*!TU, n + XY!Z[#+ ¶ 1** ml 38!$, q3

rz=67*+ ©2bW2ª72fg

8cy3`aa= 7!·q?xk+  HP-,* CW3"?tS+ FG3"?¸op#, T+

A_ /.//- cm \qD!, + ¯QS +**/

z=67*QS"FG!i¬#?q++.. kg 3,** ml 38!r¹+ V567+ V567῎|

DPPH ABC7Do^bW©Sf*$8 + : ++ |*!m +./ l º@ #+ V567»^FG!X#+ ABTS ABC7Do"bW]# ¶ 0.* l !$, 4<5¼s +*,.2

?©3o½tytS+ O, ABC7Do"pqῌr :  g s3t

 19 

+    n.

,   2*ῌ 

/
34-3
,4*.
-40+
+/43




*4.0
*4*//
*4*/2
*4*0*

mgῌῌgῌ

/,. mg u+,  !"#$%&'()* p*4*/

 + 
 !"#$%&'()* p*.*/

! "#$   n.

91+,,#m>v7oK/ wxyz{|9)

RSTU --/ ,3- ,,, nm R} yzv ~K LC-ESIMS S\] FAB-MS ^_IRSTU? mῌz 0,- -M-H.

eN)1;[9vJ  0,.
78#> JK  ./ ~K %Bd()
R%PO)[9 mῌz .0+ vJK/DMSO-d0 + H +- C S\] NMR

a lK  ,/ lKvU  g R]R MeOH-d. R lK3<%)as3tT@A%BCvE~JUT#>GHIJ`a>5b + , R\c S/ %BdeNfC

K/+.+/



12345678#$9:;<2 ,- -, .-dihydroxy-,% &'( )*phenylethyl +-O-a-L-rhamnopyranosil-+0--b-D-.-o" , 6

caffeoyl-glucopyranoside  : verbascoside  /[9 S. > S/ RH 1 6[9viJ ">GHIJK/ ~K HPLC  i UV yz{|9 g hij

HPLC RklK>mn

=>? 3 6@A%BCD EF>GHIJK  -) MS {|9) ¡>¢£R5bl S/ 

¤/ mJI7 S. S/ S0 S2 R¥¦,# . 6D

$9:;<278#>§¨K/ ©ª« @{)PQ¬ DPPH >­®l /+1 nm  DPPH L

g  + g R +, mg +.,῍ $9:;<2v

M9N )OPQRSTUV"WX:YZ[9 l
Km>°I mJIv g V±tD>GHI
JK  - ²/ 7? S/ ³ WX:YZ[9l  g s3tR³?´lUT#D>GH
IJKm>°I mD¶«ῌu

E~J#m>v¯lK/+, g @A%BC REFm>°IµTs·¸K/ 9

3t l ~K¹V±tD56$9:;<N )OP%Y  g  +.. kg \c S

278#m>v¯lK/ 5ºR :»¼½ ,

EFGHIJIKL M /2 N M - O ,*++ P - Q

92

 20 
ῐ ,S/ DMSO-d0
dC
Ag-+
-,
--.
-/
-0
-a
-b
Caf-+
-,
--.
-/
-0
-a
-b
-g
Glc-+
-,
--.
-/
-0
Rhm-+
-,
--.
-/
-0

+,340
++042
+./4/
+..4+
++04*
+,*4*
1*42
-/4/
+,04*
++/4,
+.04+*+.34*++04+,+43
+004,
++.4*
+.04+*+*,42
1/4***
134/
0340
1/4***
0+4,
+*+42
1+4*
1*43
1,4+
034+241

S/ MeOH-d.

dH mult, J in Hz
04/2 d, +41

04/3 d, 24*04./ dd, +41 24*-4// m -42. m
,400 m
0432 d, +41

041, d, 24*043. dd, +41 24*04+0 d, +0
14., d, +0.4-+ d, 24*
-4+1 t, 24/
-400 t, 34*.401 t, 34/-4.. m
-4,2 m -4-/ m
.432 d, +4/
-40. m
-4,. dd, -4* 34/
-4*0 t, 34/
-4-+ m
*43, d, 04*S/ ῍ +H- ῌ῏῎

HMBC

dC

Ag-H/, Ag-Ha, Ag-Hb
Ag-H0, Ag-Hb
Ag-H,, Ag-H/
Ag-H,, Ag-H0
Ag-H0
Ag-H,, Ag-Hb
Ag-Hb, Glc-H+
Ag-H,, Ag-H0, Ag-Ha
Caf-H/, Caf-Hb, Caf-Hg
Caf-H0, Caf-Hg
Caf-H,, Caf-H/
Caf-H,, Caf-H/, Caf-H0
Caf-H0Caf-H,, Caf-Hg
Caf-Hb, Caf-Hg, Glc-H.

Caf-H,, Caf-H0
Glc-H,, Ag-Ha
Glc-HGlc-H,, Glc-H., Rhm-H+
Glc-H-, Glc-H/
Glc-H., Glc-H0
Glc-H., Glc-H/
Rhm-H,, Glc-HRhm-H+
Rhm-H,, Rhm-H.
Rhm-H,, Rhm-H-, Rhm-H0
Rhm-H+, Rhm-H., Rhm-H0
Rhm-H., Rhm-H/

+-+4/
++14+
+.04,
+..41
++04+,+4,
1,4-040
+,141
++/4,
+.043
+.343
++04/
+,-4+024++.41
+.24+
+*.4,
104+
2+41
1*40
1040,4.
+*-4+
1,4.
1,4+
1-42
1*4/
+24/

dH mult, J in Hz
0403 d, ,4*0401 d, 24/
04/0 dd, ,4* 24/
-41* m .4*. m
,413 m
14*/ d, ,4*0411 d, 24/
043/ dd, ,4* 24/
04,1 d, +0
14/3 d, +0
.4-1 d, 24*-4-3 dd, 24/ 34*-42+ t, 34*.43, t, 34/
-4/+ m-4/, m -40, m
/4+2 d, ,4*
-43+ dd, ,4* -4/
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