ﻓﺼﻠﻨﺎﻣﺔ ﭘﮋوﻫﺸﻲ ﺗﺤﻘﻴﻘﺎت ﮔﻴﺎﻫﺎن داروﻳﻲ و ﻣﻌﻄﺮ اﻳﺮان ﺟﻠﺪ 20 ﺷﻤﺎرة 2، ﺻﻔﺤﺔ 149-158، (1383)

اﺳﺘﺨﺮاج و ﺷﻨﺎﺳﺎﻳﻲ ﺗﺮﻛﻴﺒﻬﺎي ﻓﺮار . sibthorpiana Guss

ﻓﺎﻃﻤﻪ ﺳﻔﻴﺪﻛﻦ1

ﭼﻜﻴﺪه            !"  #"   Echinophora  $ %&' $ %& $#    ( ) *     %&+   ,-  . .! #  /01 $2 $ 3 ( . 04 $ %& 56

Echinophora sibthorpiana  . 4#8 !" #+    $9!:- ;    " @' $  A<  #8 !0< *= > $?  +"  >  Guss.) G .4 !"  $B  C( ( !: D ( E!-       4 F=8 > G . " 0 - F=8 !" > ( H0&   > ( $  >  > H(#< >

?,% A"# > "  (GC) A"# > " *% > % ( I J   .H6" 1 !  '   4 # (GC/MS)  K L!< ( 4 I  0!  4   4 M! + Echinophira sibthorpiana    ?! (  #" ;   . #( W# X ?!%  (%OS/V)  )6N  $(%OS/Q)  NON %  !&(  0! >  +   )6N     NON % >  # ?( 1  :  #(  ?( 1  !  # %&+ %4 (N=  >  @ I  % #   .4 ( %

واژهﻫﺎي ﻛﻠﻴﺪي: 4#8 .  $Echinophira sibthorpiana Guss. $  $ % NON .W# X ?!% $ )6N  $ 

[email protected] :  !" #$ ,         

 اﺳﺘﺨﺮاج و ﺷﻨﺎﺳﺎﻳﻲ ﺗﺮﻛﻴﺒﻬﺎي ﻓﺮار .Echinophora sibthorpiana Guss

ﻣﻘﺪﻣﻪ   (   #"        !"  #"   . 4#8 

 sibthorpiana   ( *  #"      ,-  platyloba  cinerea 04 $ %& 56 $ %&' $!  %& $#    ( ) orientalis .(SOZ[ $ Y)  .! #  /01 $2 $ 3 ( .

$%'!%  [V  ]V \  ( $ $     G H + !" E. sibthorpiana ; .H HC  ^!C_  1  $^+ ( !(#8  #   ( $D#G !  +%  @'%b $ 4 !` $  "0" ( a ' >  "  !"

 E. sibthorpiana > #, .4 ( !   8 !" ; ?" ^# .H % .(S  $  1) #4  S  '4 ?34 cC(  >0 : $ B`  W '4  E. sibthorpiana  !65  =%  .4 (  .

#  %& G  ( : < > 4 @' ) E. sibthorpiana #+ d      4   ;  M! > .(Seee $Ahmed et al) H %6" 1    NON % $(%Sf/O)  )6N  $(%[V/ ) W# X ?!%   ; '  4 .+  ?!3= (%O/Z)  )6 %(  (%Q/O) ;'! N  G $(%SZ/ )   #   H!!  H!' Y > . 4#8  > *  +  #" . #4 g b  I)8 #< (  H %6" 1

  Echinophora cinerea (Boiss.) Hedge #+    6  0!  ; '  4   4 M! ]Z .H 4   GC/MS  GC !#( $(%Z/[) ;'! N  G $(%e/Q)  )6N %( $(%Sf/[) ;!GN  $(% V/f)  )6N 

.(]VV] $Sajjadi et al) H #( (% /Q) W# %!  (%[/ ) W# !

ﻓﺼﻠﻨﺎﻣﺔ ﭘﮋوﻫﺸﻲ ﺗﺤﻘﻴﻘﺎت ﮔﻴﺎﻫﺎن داروﻳﻲ و ﻣﻌﻄﺮ اﻳﺮان ﺟﻠﺪ 20 ﺷﻤﺎرة 2 

 % > Echinophora cinerea " 8 4    $* 9!:-  N  $(%SV/Z)  )6N %( $(%fS/ )  )6 N   4   4 M! Se / 6

$Ahmadi et al)   #(   '  0! (%f/S) ;'! N  G  (%e/f) ;!G .(]VVS

 >   !  E. tenuifolia subsp. Sibthorpiana 8 4   .H  H( %S/S  S/O $V/e > ( ( (  8  H= 0  $; 6) H4 (  %ef/eS $%QZ/][ M! (     +  4   4 I  0!  )6N   W# X ?!% $ NON % ? 4    ?!3=    %eZ/OQ

.(]VVO $Ozcan et al)   #(  )6N  I M!  4   4 M! SZ E. chrysantha    .(Seef $Baser et al) H #(  H 4  h!C= M! O .! ! > E. lamondiana    ' . (%Z/ ) ;'! N  G  (%]Z/Z)  )6N  $(% Q)  NON %

.(]VV] $Baser et al)   #(   H 4 d b  E. tenuifolia   (3! _ 2i #  .!  :!:-  #" ;    4 hC=  (]VV] $Aridogan et al  ]VVS $Akin et al) .  % ( _ H! 6

W '4) Fb > +" ?,6  E. sibthorpiana #+ d  9!:- ;  I J K %  %6" 1   #      "  @' (  .+   =  %& G  4 d b    K % (      %+ 04

 اﺳﺘﺨﺮاج و ﺷﻨﺎﺳﺎﻳﻲ ﺗﺮﻛﻴﺒﻬﺎي ﻓﺮار .Echinophora sibthorpiana Guss

ﺷﻜﻞ ﺷﻤﺎره 1- ﺗﺼﻮﻳﺮ ﮔﻴﺎه Echinophora sibthorpiana Guss

روش ﻛﺎر اﻟﻒ- ﺟﻤﻊآوري ﮔﻴﺎه و اﺳﺘﺨﺮاج اﺳﺎﻧﺲ

> 3 > (Echinophora sibthorpiana)  . 4#8 !" #+     @' ?  +" J  $(  W '4) Fb   !0<  + *= $@  * 2 :!:- &k d# (+ E# !"   4 !j > G . " !" H(#< ! > G .H6" 1 4 F=8 ( M        !" lC%   $B  C( ( !: D (   8 :   $I [ ( !" > ( H0&   > ( .4  > H(#< ^ 2 # E#   " . H( %V/fQ $F=8

ﻓﺼﻠﻨﺎﻣﺔ ﭘﮋوﻫﺸﻲ ﺗﺤﻘﻴﻘﺎت ﮔﻴﺎﻫﺎن داروﻳﻲ و ﻣﻌﻄﺮ اﻳﺮان ﺟﻠﺪ 20 ﺷﻤﺎرة 2 

[V    !" > d" [ : $!"    >  !" H(#< ;!! H   I  H(#< .! $H( i > ( ! > G  H6" 1 *!%   . " 0 -

ب- ﺷﻨﺎﺳﺎﻳﻲ ﺗﺮﻛﻴﺒﻬﺎي ﺗﺸﻜﻴﻞ دﻫﻨﺪه

. ( ;%0  ;%6   (GC) A"# > " *% ( &  9. > G  %   ( I J  &  $>  ;% ( ( ( !% H  $#% J

(GC/MS)  K L!< ( 4 ?G# A"# > " *% (  4 9!1 > % ( m . H( <#(  +d"#     !<  4 9.  0! ( & :    !<   $#  > (   $ > (  >

?!3=  0! $SATURN .6d  ## 2 )< > %   %  +  0 - ( .H6" 1 !  '   4 # $ &  + J . ( E4  $( ]]  e W   ("!+ 9. >  > ( . " % ( #' 9. ( ( =) #%

ج- ﻣﺸﺨﺼﺎت دﺳﺘﮕﺎﻫﻬﺎي ﻣﻮرد اﺳﺘﻔﺎده

دﺳﺘﮕﺎه GC

1  % fV W#< ( DB-1 #% 9A W (Shimadzu) > '!4 A"# > " .  ( .4 ( %3! V/][   ;  > 6 n H C_  %'!! V/][ $   '+  L1# :!1 [ > G  4 \4 *!%   V > #% J ! *!%   ][V (  %6  c.6 :!1   H ( K ( #%   ;8 >  SV)  ]fV #%3  9. Y-   .H

> " >  #( FID \# > GC *%  % # #%3 .H 4 ^!Y (n (

 اﺳﺘﺨﺮاج و ﺷﻨﺎﺳﺎﻳﻲ ﺗﺮﻛﻴﺒﻬﺎي ﻓﺮار .Echinophora sibthorpiana Guss

W#<  ! i ( %'!%  O] H (  .H 4 % ? J > " #( ^!+ .H  HJ #%

دﺳﺘﮕﺎه GC-MS #% . #  \# >  K L!< ( 4 ?G# O VV   A"#  > "

  ;  > 6 n H C_  %'!! V/][ 1  % fV W#< ( DB-1  #% . ( ( !04 #% J . ( .H #( %3! V/][

]fV) #%    > n (  SV 9. Y-   .H #( GC *% %'!%  OS/[ H (  #( d#!+ ? J > " .H 4 ^!Y ( *!%   #!.! # X  $! i F (( ;3  > .H  HJ #% W#<  ! i ( .H #( O V  V >  !J  H %3 ZV

ﻧﺘﺎﻳﺞ > ( H0& $!"   >   #' + H(#< I ;!! (      > G . H( %V/fQ  . 4#8   > ( . " 0 - !" F=8 ' I  #   0 - ( $  !<  "#    H(  4 g #  +  > % (    !<   ( .!   0!

( d1 $(SeQZ $Shibamoto  SeeV $Davies) @(   DB-1 #%  ( @(  W    .!  > ?I J K % . "   + ?!3=  0!   4 . #4  ]  '4 ?34   ( o#( d"#   S  M! SZ $#  > (  +  0 -    !<   ( .4   4 $ . 4#8 " 8 4  

ﻓﺼﻠﻨﺎﻣﺔ ﭘﮋوﻫﺸﻲ ﺗﺤﻘﻴﻘﺎت ﮔﻴﺎﻫﺎن داروﻳﻲ و ﻣﻌﻄﺮ اﻳﺮان ﺟﻠﺪ 20 ﺷﻤﺎرة 2 

N  $(%OS/e)  NON % $  ;  4   4  0! ; ' .! ( ;! . #( (%[/O)  )6 N %(  (%Sf/e) W# X ?!% $(%OS/V)  )6 .H4 #    %S/] .! ( ;!G N  "  %]

ﺟﺪول ﺷﻤﺎره 1- ﺗﺮﻛﻴﺒﻬﺎي ﻣﻮﺟﻮد در اﺳﺎﻧﺲ اﻧﺪام ﻫﻮاﻳﻲ (Echinophora sibthorpiana) ردﻳﻒ ﻧﺎم ﺗﺮﻛﻴﺐ اﻧﺪﻳﺲ ﻛﻮاﺗﺲ (%) '/ %&  α-thujene '/( %&% & α-pinene '/( %)* sabinene ( '/ %+' * β-pinene &/' %. myrcene - (/' ''' ) α-phellandrene (/% ''. + δ-3-carene */+ '( p-cymene . 01 '. limonene % -/( '& ' β-phellandrene '/ '(+  (Z)-β-ocimene 01 '* & (E)-β-ocimene /& '*% ( γ-terpinene '/- '++ terpinolene * / '%% 1,3,8-p-menthatriene - '/& &)% trans-anethole ) )/% (++ methyl eugenol + .   " 0 - DB-1 #% M&J ( #  +  %V/V[ > %' N .!

 اﺳﺘﺨﺮاج و ﺷﻨﺎﺳﺎﻳﻲ ﺗﺮﻛﻴﺒﻬﺎي ﻓﺮار .Echinophora sibthorpiana Guss

ﺷﻜﻞ ﺷﻤﺎره 2- ﻛﺮوﻣﺎﺗﻮﮔﺮام اﺳﺎﻧﺲ Echinophora sibthorpiana

ﺑﺤﺚ  #";!'+    (  %& G  4 d b  9!:- ( K % ; & :

 .!  %&+ ( = '  0! "    = (Seee $Ahmed et al) I M! %O] J  .! (    NON % #< ( .H 2 %  !&( #(  %& G  9!:- #  #'  +  ?!3=  ( #       W# X ?!% 6< > .H %4 # %SZ/ .! (  d M!  H  p ,%8 #8 (    %[V > c!( I M! #(  #' ; o#(  #   M!    ; .H #( %SZ  ( #   .4 (  H4 ( : '!1 E4  c ?-  !" H4 (  > (

 =  ;  + #" * ( E. sibthorpiana   M! & :    H   ; '  0! > * 3   )6N   + 

ﻓﺼﻠﻨﺎﻣﺔ ﭘﮋوﻫﺸﻲ ﺗﺤﻘﻴﻘﺎت ﮔﻴﺎﻫﺎن داروﻳﻲ و ﻣﻌﻄﺮ اﻳﺮان ﺟﻠﺪ 20 ﺷﻤﺎرة 2 

E. chrysantha $(]VVS $Ahmadi et al  ]VV] $Sajjadi et al) E. cinerea #( .! (]VV] $Baser et al) E. lamondiana ;!q'+  (Seef $Baser et al) E. tenuifolia    W# X ?!% 3! J  .  #rJ I  0! > 3 .!  NON % .(]VVO $Ozcan et al) H I . > subsp. Sibthorpiana .H M! ; ' E. lamondiana      3 ( # (  H6" b!% ( ; > # ;!q'+

  ( ( =  I .  H % ( _ H!I 8  E. tenuifolia .4 ( %4 % ( _ p#8  # .! _ J   %&+ E. sibthorpiana % # ^   0! > *'+  )6N %(  N   +.   NON %   >  Y ( ;( ( .%&+ %4 ( – = @ I  >   .  % @ I  #";  #  '+ (  !" sm -  !" ;

ﺳﭙﺎﺳﮕﺰاري ; d b  ( d>n 2 3  @  * 2 :!:- &k d%- ;!#t& > + !" '!4 " d%-  3'+ > ;!q'+ .d.* m  #' ^+6  9!:-     >(   '-   1 u#( $    + !" 2 :!:- cC( .^ 3=  %4   3'+ H 9!:-  W#<   >!

 اﺳﺘﺨﺮاج و ﺷﻨﺎﺳﺎﻳﻲ ﺗﺮﻛﻴﺒﻬﺎي ﻓﺮار .Echinophora sibthorpiana Guss

ﻣﻨﺎﺑﻊ ﻣﻮرد اﺳﺘﻔﺎده .  $I  a+6 2 =%  $  + !"   a+6 .SOZ[ $. . $ Y N .S  $@  * 2 :!:- &k 2 =%  $*  #6 $.\ $  1 N - Ahmad, V.U., Jassbi A.R., 1999. Analysis of the of Echinophora sibthorpiana Guss. By means of GC, GC/MS and C-NMR techniques, J. Essent. Oil Res., 11; 107-108. - Ahmadi, L., Mirza, M., Khorram, M.T., 2001. Essential oil of Echinophora cinerea (Boiss) Hedge and Lamond from Iran, J. Essent. Oil Res., 13; 82- 83. - Akin, M., Aktumsek, A., Okur O., 2001. Investigation of antimicrobial activities of some essential oils against some animal pathogens, Veterinarium, 12; 83-85. - Aridogan, B.C., Baydar, H., Kaya, S., Demirci, M., Ozbasar D., Mumcu E., 2002. Antimicrobial activity and chemical composition of some essential oils, Archives of Pharmacal Research, 25; 860-864. - Baser, K.H.C., Bicakci, A., Malyer, H., 2000. Composition of the essential oil of Echinophora lamondiana, J. Essent. Oil Res., 12; 147-148. - Baser, K.H.C., Ozek, T., Demircakmak, B., Bicakci, A., Malyer, H., 1996. Essential oil of Echinophora chrysantha, J. Essent. Oil Res., 8; 433-434. - Davies B. W., 1990. Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicone and Carbowax 20M phases. J. Chromatogr, 503: 1-24. - Ozcan M., Akgul A., 2003. Essential oil composition of Turkish (Echinophora tenufolia), Acta Botanica Hungarica, 45; 163-167. - Sajjadi, S.E., Ghannadi A., 2002. Composition of the essential oil of Echinophora cinerea (Boiss) Hedge et Lamond, J. Essent. Oil Res., 14; 114-115. - Shibamoto T., 1987. Retention Indices in Essential Oil Analysis, In: Capillary Gas Chromatography in Essential Oil Analysis. Edits., P. Sandra and C. Bicchi, p 259-274, Huethig, Verlag, New York.

Iranian Journal of Medicinal and Aromatic Research 246

Vol. 20 No. (2), 149-158 (2004)

Extraction and Identification of Volatile Components of Echinophora sibthorpiana Guss.

F. Sefidkon1

Abstract The genius of Echinophora presents 4 aromatic species in Iran, two of them are endemic. In this research, the aerial parts of E. sibthorpiana were collected in full flowering stage, from Tehran Provinc (north of Tehran). The materials were dried in room temprature and the essential oil isolated by steam distillation. The oil was analyzed by capillary GC and GC/MS. Among 17 compounds identified, the major components were delta-3-carene (31.8%), alpha-phellandrene (31.0%), methyl eugenol (16.9%), beta-phellandrene (5.3%) and p-cymene (4.7%). This oil could be used in cosmetic-hygenic industries because of the high amounts of delta-3-carene and alpha-phellandrene. These compounds have very good smells and used in perfumes.

Key Words: Echinophora sibthorpiana Guss., Umbelliferae, essential oil, delta-3-carene, alpha-phellandrene, methyl eugenol.

1- Research Institute of Forests and Rangelands, P. O. Box :13185-116, Tehran. E-mail : [email protected]