ﺔﻴﺒﻌﺸﻝﺍ ﺔﻴﻁﺍﺭﻘﻤﻴﺩﻝﺍ ﺔﻴﺭﺌﺍﺯﺠﻝﺍ ﺔﻴﺭﻭﻬﻤﺠﻝﺍ
ﻲﻤﻠﻌﻝﺍ ﺙﺤﺒﻝﺍ ﻭ ﻲﻝﺎﻌﻝﺍ ﻡﻴﻠﻌﺘﻝﺍ ﺓﺭﺍﺯﻭ
ﺔﻨﻴﻁﻨﺴﻗ ﻱﺭﻭﺘﻨﻤ ﺔﻌﻤﺎﺠ
ﻡﻭﻠﻌﻝﺍ ﺔﻴﻠﻜ ﺔﻘﻴﻗﺩﻝﺍ
ﻜﻝﺍ ﻡﺴﻗ ﻴ
ﺀﺎﻴﻤ
ﺏﻴﺘﺭﺘﻝﺍ ﻡﻗﺭ ... :
لﺴﻠﺴﺘﻝﺍ ﻡﻗﺭ ...:
ﺓﺭﻜﺫﻤ
ﺴﺠﺎﻤﻝﺍ ﺓﺩﺎﻬﺸ لﻴﻨﻝ ﺔﻤﺩﻘﻤ ﺭﻴﺘ
ﻡﻭﻠﻌﻝﺍ ﻲﻓ
ﺹﺼﺨﺘ ﻭ ﺔﻴﺌﺎﻴﻤﻴﻜﻭﻴﺯﻴﻓ لﻴﻝﺎﺤﺘ
ﻜ ﻴ ﺔﻴﻭﻀﻋ ﺀﺎﻴﻤ
ﻥﺍﻭﻨﻋ ﺕﺤﺘ :
ﺏﻝﺎﻁﻝﺍ ﻡﻴﺩﻘﺘ :
ﻥﺎﻤﺤﺭﻝﺍﺩﺒﻋ ﻕﺍﺭﺯﻤ ﻝﺍ ﻑﺍﺭﺸﺇ ﺕﺤﺘ
ﺭﻭﺘﻜﺩ : ﺩﻤﺤﻤ ﻡﻭﺭﻫﻭﺒ
ا :
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تاE=3
ﻡﻝ ﺎﻤ ﻥﺎﺴﻨﻹﺍ ﻡﻠﻋ ،ﻡﻠﻘﻝﺎﺒ ﻡﻠﻋ ﻱﺫﻝﺍ ﷲ ﺩﻤﺤﻝﺍ ﻡﻠﻌﻤ ﻰﻠﻋ ﻡﻼﺴﻝﺍ ﻭ ﺓﻼﺼﻝﺍ ﻭ ،ﻡﻠﻌﻴ
ﻥﻴﻌﻤﺠﺃ ﻪﺒﺤﺼ ﻭ ﻪﻝﺃ ﻰﻠﻋ ﻭ ،ﺭﺸﺒﻝﺍ .
ﺯﺠﻌﻴ ﻥﻤ ﻰﻝﺇ ﺭﻴﺩﻘﺘﻝﺍ ﻭ ﻥﺎﻨﺘﻤﻻﺍ ﻭ ﺭﻜﺸﻝﺍ ﺕﺍﺭﺎﺒﻋ ﻰﻤﺴﺄﺒ ﻡﺩﻘﺘﺃ ﺀﻲﺸ لﻜ لﺒﻗ ﻭ ﻻﻭﺃ ﻲﺒﻫﺍﻭ ﻰﻝﺇ ،ﻲﻘﻴﺭﻁ ﺭﺎﻨﺃ ﻭ ﻱﺎﻁﺨ ﺩﺩﺴ ﻥﻤ ﻰﻝﺇ ،ﻩﺭﻜﺸﻝ ﺔﺒﺴﺎﻨﻤﻝﺍ ﺕﺍﺭﺎﺒﻌﻝﺍ ﺩﺎﺠﻴﺇ ﻥﻋ ﻲﻨﺎﺴﻝ
،ﻲﺒﺭ ﻰﻝﺇ ،ﺓﺎﻴﺤﻝﺍ ﹼﻞﺟ ﺓﺰﻌﻟﺍ ﺏﺭ
ﻟﻼﺟ .ﻪ
ﺫﺎﺘﺴﻸﻝ ﻥﺎﻓﺭﻌﻝﺍ ﻭ ﺀﺎﻨﺜﻝﺍ ﻭ ﺭﻜﺸﻝﺎﺒ ﻡﺩﻘﺘﺃ ﺵﺎﻴﻋ ﻥﺒ ﺭﻴﻤﺴ
ﺢﺌﺎﺼﻨﻝﺍ ﻭ ﺕﺎﻬﻴﺠﻭﺘﻝﺍ ﻰﻠﻋ
ﺭﺒﺨﻤﺒ ﻡﺘ ﻱﺫﻝﺍ لﻤﻌﻝﺍ ﺍﺫﻫ ﺯﺎﺠﻨﺇ لﺤﺍﺭﻤ لﻜ لﻼﺨ ﻲﻝﺇ ﺎﻬﻤﺩﻗ ﻲﺘﻝﺍ ''
ﺔﻴﻌﻴﺒﻁﻝﺍ ﺕﺍﻭﺭﺜﻝﺍ ﻥﻴﻤﺜﺘ
ﻝﺍ ﻉﺎﻨﻁﺼﺍﻭ ﻲﺘﺎﺒﻨﻝﺍ لﺼﻷﺍ ﺕﺍﺫ ﺎﻴﺠﻭﻝﻭﻴﺒ ﺔﻝﺎﻌﻔﻝﺍ ﺕﺎﺌﻴﺯﺠ
'' ﻱﺭﻭﺘﻨﻤ ﺔﻌﻤﺎﺠ ﺀﺎﻴﻤﻴﻜﻝﺍ ﻡﺴﻘﺒ
ﺔﻨﻴﻁﻨﺴﻗ .
ﺔﻴﻝﺎﻐﻝﺍ ﺓﺩﻴﺴﻠﻝ ﺔﺼﻝﺎﺨﻝﺍ ﻲﺘﺍﺭﻜﺸﺘﺒ ﻡﺩﻘﺘﺃ ﺎﻤﻜ ﺵﺎﻴﻋ ﻥﺒ ﺔﻠﻴﻀﻓ
ﺓﺫﺎﺘﺴﺃ ﻰﻠﻋ ﻱﺭﻭﺘﻨﻤ ﺔﻌﻤﺎﺠﺒ
ﺔﻝﺎﺴﺭﻝﺍ ﻩﺫﻫ ﺔﺸﻗﺎﻨﻤ ﺔﻨﺠﻝ ﺔﺴﺎﺌﺭ لﻭﺒﻘﺒ ﺎﻬﻠﻀﻔﺘ ﺔﻤﻴﻘﻝﺍ ﺎﻬﺤﺌﺎﺼﻨ ﻭ ﺎﻬﺘﺎﻬﻴﺠﻭﺘﺒ ﻲﻠﻋ لﺨﺒﺘ ﻡﻝ ﻲﺘﻝﺍ
ﻨﺇ لﺤﺍﺭﻤ لﺍﻭﻁ ﺔﻨﻴﻤﺜﻝﺍ ﻭ ﺔﺼﺎﺨﻭ لﻤﻌﻝﺍ ﺍﺫﻬﻝ ﺎﻨﺯﺎﺠ
ﺔﻝﻭﺼﻔﻤﻝﺍ ﺕﺎﺒﻜﺭﻤﻝﺍ ﻰﻨﺒ ﺩﻴﺩﺤﺘ ﻲﻓ .
ﻲﻝﺎﻐﻝﺍ ﺫﺎﺘﺴﻷﺍ ﻰﻝﺇ لﻴﺯﺠﻝﺍ ﺭﻜﺸﻝﺎﺒ ﻡﺩﻘﺘﺃ ﻭ ﺩﻤﺤﻤ ﻡﻭﺭﻫﻭﺒ
ﻭ ﻪﺘﺎﻬﻴﺠﻭﺘﺒ ﻲﻠﻋ لﺨﺒﻴ ﻡﻝ ﻱﺫﻝﺍ ،
لﻤﻌﻝﺍ ﺍﺫﻬﻝ ﺎﻨﺯﺎﺠﻨﺇ لﺤﺍﺭﻤ لﺍﻭﻁ ﺔﻨﻴﻤﺜﻝﺍ ﻭ ﺔﻤﻴﻘﻝﺍ ﻪﺤﺌﺎﺼﻨ .
ﺫﺎﺘﺴﻷﺍ ﻰﻝﺇ ﻱﺭﻜﺸﺒ ﻪﺠﻭﺘﺃ ﻙﻝﺫﻜ ﻥﻴﺩﻝﺍﺭﻭﻨ ﺔﺠﻴﻐﺒ
ﺫﺎﺘﺴﻷﺍ ﻭ ﻝ ﺭﺘﻴﻋﺯ
ﻥﺴﺤ ﺎﻤﻬﻝﻭﺒﻗ ﻰﻠﻋ
ﺔﺸﻗﺎﻨﻤﻝﺍ ﺔﻨﺠﻝ ﻲﻓ ﺔﻜﺭﺎﺸﻤﻝﺍ .
ﺩﺍﺭﻓﺃ ﻊﻴﻤﺠ ﻰﻝﺇ ﺹﻝﺎﺨﻝﺍ ﺭﻜﺸﻝﺎﺒ ﻡﺩﻘﺘﺃ ﺎﻤﻜ ﺎﻨﺭﺒﺨﻤ
ﻭ ﺢﺌﺎﺼﻨ ﻥﻤ ﻲﻝ ﻩﻭﻤﺩﻗ ﺎﻤ ﻰﻠﻋ
ﺔﺼﺎﺨ ،ﺕﺍﺩﻋﺎﺴﻤ ﺔﻴﻫﺯ ﻡﻭﻠﺒ
, ﻰﺴﻴﻋ ﻥﺒ ﺔﺒﻴﻫﻭ
، ﻥﺎﻀﻤﺭ ﻱﺭﻴﻐﺼ ،
ﻥﻴﺫﻝﺍ ﻰﺴﻨﺃ ﻥﺃ ﻥﻭﺩ
ﻲﺘﻌﻓﺩ ﺩﺍﺭﻓﺃ ﺀﺍﺯﻋﻷﺍ ﻲﺘﺍﻭﺨﺃ ﻭ ﻲﺘﻭﺨﺍ ﺔﺒﺎﺜﻤﺒ ﻡﻫﺭﺒﺘﻋﺃ ﺩﻤﺤﻤ
ﻡﺎﻬﺴ , ﻥﺍﻭﻀﺭ, ﺯﻭﺭﻴﻓ ,
ﺏﻴﺒﻝ ,
ﺓﺩﺠﻤ ﺭﺎﻤﻋ , ﺓﺭﻴﻤﺴ , ﺩﻴﺭﻓ ,
ﻥﻴﺩﻝﺍ ﻑﻴﺴ, ﻥﺎﻨﺤ,
ﺓﺯﻴﻭﻝ , ﻭ ﻕﻴﻓﻭﺘﻝﺍ لﻜ ﺎﻌﻴﻤﺠ ﻡﻬﻝ ﻰﻨﻤﺘﺃ ﻭ
ﺡﺎﺠﻨﻝﺍ .
ﺩﻴﻌﺒ ﻭﺃ ﺏﻴﺭﻗ ﻥﻤ ﻲﻨﺩﻋﺎﺴ ﻥﻤ لﻜ ﻰﺴﻨﺃ ﻻ ﺎﻤﻜ .
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..
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52.
-IV 2 - 1 - أ - 3 - دو 2 ص,< ا X&
NaOAc ..
...
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52..
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+H3BO3 NaOAc
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52
-IV 2 - 1 - أ - 5 - دو 2 ص,< ا X&
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و AlCl3+HCl ...
... 54
2–IV - 2 - 2B&[ا يوا Oا ..RMN
...
....
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58
2–IV - 2 - أ - 2B&[ا يوا Oا RMN-1H
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58…...
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68...
2–IV - 3 - ج - - 2و<">ا شا ...
...
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68..
-V Kا ه >ا 68...………...………..
-V 1 - Hا %ا ...
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69.
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70
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71
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75...……….
1– II - <+ا ص(<=ا .
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78….……
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; 9,<ا رB"ا ?H .
..
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. 96
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115
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1
ﻘﻤﻝﺍ ـ ﺔﻤﺩ :
،ﻲﻌﻴﺒﻁﻝﺍ ﺝﻼﻌﻝﺍﻭ ﺏﻁﻝﺎﺒ ﺱﺎﻨﻝﺍ ﻡﺎﻤﺘﻫﺍ ﺓﺩﺎﻴﺯ ﻲﻤﻭﻴﻝﺍ ﺎﻨﻌﻗﺍﻭ ﻲﻓ ﺩﻫﺎﺸﻤﻝﺍ ﻥﻤ ﺔﻴﺫﻏﻷﺎﺒ ﻱﻭﺍﺩﺘﻝﺍﻭ
ﺓﺭﺒﺨﻝﺍ لﻫﺃ ﻥﻤ ﺔﺒﺭﺠﻤﻝﺍ ﺔﻴﺒﻌﺸﻝﺍ ﺕﺎﻔﺼﻭﻝﺍ ﻭ ﺔﻴﺒﻁﻝﺍ ﺕﺎﺘﺎﺒﻨﻝﺍ ﻭ ﺏﺎﺸﻋﻷﺍ ﻭ ﺔﻴﻌﻴﺒﻁﻝﺍ .
،ﺭﻴﻗﺎﻘﻌﻝﺍ ﻡﻅﻌﻤ ﻲﻓ ﻲﺴﻴﺌﺭ ﺭﺩﺼﻤﻜ ﺏﺎﺸﻋﻷﺍ لﻤﻌﺘﺴﺘ ﺕﻨﺎﻜ ﺎﻤﻴﺩﻗ [2,1]
ﺕﺎﺒﻨﻝﺍ ﺔﻜﻠﻤﻤﻓ ﺏﻁﻝﺍ ﺩﻭﺯﺘ
ﺓﺭﻤﺘﺴﻤ ﺔﻔﺼﺒ ﻭ
ﺏﺍﺭﺸ ،ﺕﺎﻴﺎﺸ لﻜﺸ ﻰﻠﻋ ﻡﺎﺨﻝﺍ ﺎﻬﻠﻜﺸ ﻲﻓ لﻤﻌﺘﺴﺘ
،ﻉﻭﻘﻨﻤ ﻭﺃ ﻥﺎﻫﺩ ،ﻡﻫﺍﺭﻤ
ﻕﻴﺤﺎﺴﻤ .
ﻲﻝﺍﻭﺤ ﻰﻝﺇ ﺏﺎﺸﻋﻷﺍ ﺏﻁ ﺭﻭﻬﻅ ﺩﻭﻌﻴﻭ 60000
ﺔﻨﺴ ﻑﺸﺘﻜﺃ ﺕﻴﺤ ﺔﻨﺴ
) (1960 ﻲﻓ ﺭﺒﻗ
ﻕﺍﺭﻌﻝﺍ لﺎﻤﺸ ﺓﺭﺎﻐﻤ ]
[3
، ﻤﻝﺍ لﻴﻝﺎﺤﺘﻝﺍ ﺕﺭﻔﺴﺃ ﺫﺇ ﺔﻴﺭﺒﺨ
ﻰﻠﻋ ﻲﻤﻅﻌﻝﺍ لﻜﻴﻬﻝﺎﺒ ﺔﻁﻴﺤﻤﻝﺍ ﺔﺒﺭﺘﻝﺍ ﻰﻠﻋ ﺩﻭﺠﻭ
ﻡﻝﺎﻌﻝﺍ ﺀﺎﺤﻨﺃ لﻜ ﻲﻓ لﻤﻌﺘﺴﺘ لﺍﺯﺘ ﻻ ﺔﻴﺒﻁ ﺎﻬﻨﻤ ﺔﻌﺒﺴ ﺕﺎﺘﺒﻨ ﻲﻨﺎﻤﺜﻝ ﻊﻠﻁ ﺏﻭﺒﺤ ] .
[4
ﻝﺍ ﺏﻁﻝﺍ ﻭ ﺀﺎﻴﻤﻴﻜﻝﺍ ﺭﻭﻁﺘ ﻊﻤ ﺭﺼﺎﻌﻤ
ﺔﻌﻨﺼﻤﻝﺍ ﺔﻴﻭﺩﻷﺍﻭ ﺭﻴﻗﺎﻘﻌﻝﺎﺒ ﻱﻭﺍﺩﺘﻝﺍ ﻰﻠﻋ ﺩﻤﺘﻋﺃ ]
[5 ﺩﻘﺘﻋﺍ ﺩﻗ ﻭ
ﺔﻌﻨﺼﻤﻝﺍ ﺔﻴﻭﺩﻷﺍ ﻩﺫﻫ ﻥﺃ ﻥﻭﺭﻴﺜﻜﻝﺍ ﺔﻴﺒﻁﻝﺍ ﺕﺎﺘﺎﺒﻨﻝﺍ لﺤﻤ لﺤﺘ ﻑﻭﺴ
ﻝﺍﻭ ﺏﻁﻝﺍ ﻲﻓ ﺔﻠﻤﻌﺘﺴﻤﻝﺍ ﺏﻁ
ﻲﺒﻌﺸﻝﺍ ﻥﺃ ﻊﻗﻭﺘﻤﻝﺍ ﻥﻤ ﻥﺎﻜﻭ ، ﻱﺫﻝﺍ ﻥﻜﻝ ، ﺭﻴﻗﺎﻘﻌﻝﺍ ﻡﻠﻋ ﻲﻓ ﺔﺤﺴﺎﻜﻝﺍ ﺓﺭﻭﺜﻝﺍ ﻩﺫﻫ ﻡﺎﻤﺃ ﺽﺭﻤﻝﺍ ﻊﺠﺍﺭﺘﻴ
ﺱﻜﻌﻝﺍ ﻭﻫ ﺙﺩﺤ لﺒ ، لﺒﻗ ﻥﻤ ﺓﺭﺸﺘﻨﻤ ﻭﺃ ﺔﻓﻭﺭﻌﻤ ﻥﻜﺘ ﻡﻝ ﺎﻀﺍﺭﻤﺃ ﺙﻴﺩﺤﻝﺍ ﻥﺎﺴﻨﻹﺍ ﻑﺭﻋ ﺩﻘﻓ ، ﺎﻤﺎﻤﺘ
لﺨﺩ ﻭﻀﻌﻝﺍ ﺀﺎﻴﻤﻴﻜﻝﺍ ﻡﻠﻋ ﻲﻓ ﺏﻴﻫﺭﻝﺍ ﻡﺩﻘﺘﻝﺍ ﻰﻝﺇ ﻙﻝﺫ ﻊﺠﺭﻴﻭ ، ﺔﻨﻤﺯﻤﻝﺍ ﺽﺍﺭﻤﻷﺍ ﺭﺼﻋ ﻲﺘﻝﺍ ﺔﻴ
ﺕﻠﺨﺩﺃ
ﻤ ﻊﻴﻤﺠ ﻲﻓ ﺔﻴﺌﺎﻴﻤﻴﻜ ﺩﺍﻭﻤ ﻥﻴﺩﺎﻴ
لﻋ ﺕﺭﺜﺃ ﻲﻝﺎﺘﻝﺎﺒﻭ ، ﻥﺎﺴﻨﻹﺍ ﺔﺌﻴﺒ ﺕﺜﻭﻝﻭ ، ﺓﺎﻴﺤﻝﺍ ، ﻪﺘﻭﻗﻭ ﻪﺘﺤﺼ
ﺭﻴﺜﻜﻝﺍ لﺍﺯ ﺎﻤ ﺔﻌﻨﺼﻤﻝﺍ ﺔﻴﻭﺩﻷﺍ ﻥﺎﻓ ﻙﻝﺫﻜ ، ﺽﺍﺭﻤﻷﺍ ﺔﻤﻭﺎﻘﻤ ﻲﻓ ﻪﺘﻋﺎﻨﻤﻭ ﺕﺎﻤﻭﻠﻌﻤ ﻰﻝﺇ ﺭﻘﺘﻔﻴ ﺎﻬﻨﻤ
ﺭﺎﺜﻵﺍ ﻥﻤ ﺭﻴﺜﻜﻝﺍ ﺎﻨﻝ لﻤﺤﻴ ﻲﻤﻠﻌﻝﺍ ﺙﺤﺒﻝﺍ لﺍﺯﺎﻤﻭ ، ﻰﻓﻭﺃ ﺍ ﺔﻴﺒﻨﺎﺠﻝﺍ
ﺎﻤﺇ ، ﺔﻌﻨﺼﻤﻝﺍ ﺔﻴﻭﺩﻷﺍ ﺽﻌﺒﻝ ﺓﺭﺎﻀﻝ
ﺏﺒﺴﺒ ﻥﺎﺼﻘﻨ ﺎﻬﻨﻷ ﺎﻤﺇﻭ ﺎﻬﻨﻋ ﺔﻓﺭﻌﻤﻝﺍ ﻑﻭﺭﻅ ﺕﺤﺘ لﻤﻌﻤﻝﺍ ﻲﻓ ﺎﻫﺭﻴﻀﺤﺘ ﻡﺘ ، ﺓﺯﻜﺭﻤ ﺔﻴﺌﺎﻴﻤﻴﻜ ﺩﺍﻭﻤ
، ﺔﻴﺴﺎﻗ ﺔﻴﺌﺎﻴﻤﻴﻜ ﺕﻼﻋﺎﻔﺘ ﻥﺃ ﻻﺇ لﺠﻭ ﺯﻋ ﻕﻝﺎﺨﻝﺍ ﺔﻤﻜﺤ ﺕﺒﺃ ﺎﻤﻨﻴﺒ
ﺘ ﺕﺎﺘﺎﺒﻨﻝﺍ ﻲﻓ ﺔﻠﻋﺎﻔﻝﺍ ﺩﺍﻭﻤﻝﺍ ﻩﺫﻫ لﻌﺠ
ﺕﺍﺯﻴﻜﺭﺘﺒ ﻱﺭﺸﺒﻝﺍ ﻡﺴﺠﻠﻝ ﻥﻜﻤﻴ ، ﺔﻠﻬﺴ ﺔﻀﻔﺨﻤ
ﺔﻴﻌﻴﺒﻁﻝﺍ ﺎﻬﺘﺭﻭﺼ ﻲﻓ ﻕﻓﺭﺒ ﺎﻬﻌﻤ لﻋﺎﻔﺘﻝﺍ .
ﻡﺍﺩﺨﺘﺴﺍ ﻥﺃ ﺕﺒﺜ ﻭ ﺔﻴﻋﺎﻨﺼﻝﺍ ﺔﻴﻭﺩﻷﺍ
ﺏﺒﺴﻴ ﺩﻗ ﺁ
ﺍﺭﺎﺜ ﺔﻴﺒﻨﺎﺠ
،ﺓﺭﺎﻀ ﺔﻴﻝﻭﺩﻝﺍ ﺕﺍﺭﻤﺘﺅﻤﻝﺍ ﺕﺼﻭﺃ ﺎﻤﻜ
ﺕﺎﺘﺎﺒﻨﻝﺍ ﻰﻝﺇ ﻱﺃ ﺔﻌﻴﺒﻁﻝﺍ ﻰﻝﺇ ﺓﺩﻭﻌﻝﺎﺒ ﺔﻋﺎﻨﺼﻝ ﻥﻤﺁ ﺭﺩﺼﻤ ﺎﻬﺘﻔﺼﺒ ﺎﻬﺒ ﻡﺎﻤﺘﻫﻻﺍﻭ ﺔﻴﺒﻁﻝﺍ
ﺔﻴﻭﺩﻷﺍ .
ﺫﻨﻤ ﻁﺍﺭﻗ ﻭﺒﺃ لﺎﻗ ﺩﻘﻝﻭ ﻡﺎﻋ 4500
) ﻥﻜﻴﻝ ﺫﻏ ﻲﻬﻓ ، ﻪﻀﺭﺃ ﺕﺎﺒﻨﺒ ﺽﻴﺭﻤ لﻜ ﺍﻭﺠﻝﺎﻋﻭ ، ﻙﺀﺍﻭﺩ ﻙﺅﺍ
ﻪﺌﺎﻔﺸﻝ ﺏﻠﺠﺃ (
.
2
ﺔﻴﺒﺭﻌﻝﺍ ﺭﺎﻁﻗﻷﺍ ﻯﺩﻝ )
ﻹ ﺎﻬﺘﻌﻗﺭ ﻉﺎﺴﺘ ﺎﻫﻭﺠ لﺍﺩﺘﻋﺍﻭ
( ﻥﻤ ﺔﻠﺌﺎﻫ ﺔﻴﺩﺎﺼﺘﻗﺍ ﻯﺭﺨﺃﻭ ﺔﻴﻌﻴﺒﻁ ﺓﻭﺭﺜ
، ﺔﻴﺭﻁﻌﻝﺍﻭ ﺔﻴﺒﻁﻝﺍ ﺏﺎﺸﻋﻷﺍ ﺎﻤ ﻙﻝﺫ ﻰﻠﻋ ﺩﻬﺸﻴﻭ ، ﻥﺎﻤﺯﻝﺍ ﻡﻴﺩﻗ ﻥﻤ ﺏﺭﻌﻝﺍﻭ ﻥﻴﻴﺭﺼﻤﻝﺍ ﺀﺎﻤﺩﻗ ﺎﻬﻤﺩﺨﺘﺴﺍ
ﻥﻭﻴﺭﺼﻤﻝﺍ ﻪﻨﻭﺩ ﻲﻓ
ﺎﻤ ﻙﻝﺫﻜﻭ ، ﺔﻴﺒﻁﻝﺍ ﺕﺎﺘﺎﺒﻨﻝﺍ ﻥﻋ ﻡﻬﺘﺎﻋﻭﺴﻭﻤﻭ ﻡﻬﺘﺍﺭﻜﺫﻤ ﻲﻓ ﺏﺭﻌﻝﺍﻭ ، ﻡﻬﺘﺎﻴﺩﺭﺒ
ﻪﻴﻭﺤﺘ
، ﻡﻬﻀﺍﺭﻤﺃ ﺝﻼﻋ ﻲﻓ ﺔﻤﺎﻌﻝﺍ ﺎﻬﻤﺩﺨﺘﺴﻴ ﻲﺘﻝﺍ ﺭﻭﺫﺒﻝﺍﻭ ﺭﺎﻤﺜﻝﺍﻭ ﺏﺎﺸﻋﻷﺍ ﻥﻤ ﻥﻴﺭﺎﻁﻌﻝﺍ ﻕﺍﻭﺴﺃ ﺎﻤﻭ
ﺀﺎﻤﻠﻋ ﺏﺘﻜ ﻥﻤ ﺎﻤﻫﺭﻴﻏﻭ ﺀﺎﻨﻴﺴ ﻥﺒﺍ ﺔﻋﻭﺴﻭﻤ ﻥﻭﻤﺩﺨﺘﺴﻴ ﺓﺭﺎﻁﻌﻝﺍ ﺭﺎﺠﺘ لﺍﺯﻴ ﻰﻀﺭﻤﻝﺍ ﺝﻼﻌﻝ ﺏﺭﻌﻝﺍ
ﻴ ﺎﻤ ﻥﻴﺫﻝﺍ ﻪﺘﺭﻴﺨﺫﻭ ﺓﺭﺎﻁﻌﻝﺎﺒ ﻥﻭﻨﻤﺅﻴ ﻥﻭﻝﺍﺯ
.
ﻥﻴﻴﺭﺼﻤﻝﺍ لﻀﻓ ﺭﻜﺫﻝ ﺎﻨﻫ لﺎﺠﻤﻝﺍ ﻊﺴﺘﻴ ﻻﻭ ، ﺎﻬﺒ ﻱﻭﺍﺩﺘﻝﺍﻭ ﺭﻴﻗﺎﻘﻌﻝﺍﻭ ﺏﻁﻝﺍ ﻰﻠﻋ ﺏﺭﻌﻝﺍﻭ ﺀﺎﻤﺩﻘﻝﺍ
ﺕﻴﺯ ﻡﺩﺨﺘﺴﺍ ﻥﻤ لﻭﺃ ﻥﻭﻴﺭﺼﻤﻝﺍﻭ ، ﻙﺎﺴﻤﻹﺍ ﺝﻼﻌﻝ ﻉﻭﺭﺨﻝﺍ ﺕﻴﺯﻭ ، ﻪﺠﻭﻝﺍ ﺩﻴﻋﺎﺠﺘ ﺔﻝﺍﺯﻹ ﺔﺒﻠﺤﻝﺍ
ﻥﻤ لﻭﺃﻭ ، ﺭﻌﺸﻠﻝ ﺎﻨﺎﻫﺩﻭ ﺍ ﺏﺎﻬﺘﻝﺍ ﺝﻼﻌﻝ ﺵﺎﺨﺸﺨﻝﺍ ﻡﺩﺨﺘﺴﺍ
ﺭﻤﻝﺍﻭ ﻉﺎﻨﻌﻨﻝﺍﻭ ،ﻡﻻﻵﺍ ﻥﻴﻜﺴﺘﻭ ، ﺀﺎﻌﻤﻷ
ﺡﻭﺭﻘﻝﺍ ﺝﻼﻌﻝ ﺝﻼﻌﻝ لﻅﻨﺤﻝﺍﻭ ﻥﺍﺩﻴﺩﻝﺍ ﺩﺭﻁﻝ ﻥﺎﻤﺭﻝﺍ ﺭﺸﻗﻭ ﺔﻴﻭﻌﻤﻝﺍ ﺕﺎﺒﺍﺭﻁﻀﻻﺍﻭ ﺔﻴﺩﻠﺠﻝﺍ ﺕﺎﺒﺎﻬﺘﻝﻻﺍﻭ
ﻥﺍﺩﻴﺩﻝﺍ ﺩﺭﻁﻭ لﺎﻬﺴﻹﺍ .
ﺔﻠﺌﺎﻌﻝﺍ ﻰﻠﻋ ﺎﻨﺭﺎﻴﺘﺨﺍ ﻊﻗﻭ ﺎﻨﻫ ﻥﻤ ﺔﻴﻝﻭﻘﺒﻝﺍ
ﺎﻬﻨﺃ ﺙﻴﺤ ﺔﻴﺘﺎﺒﻨﻝﺍ ﺕﻼﺌﺎﻌﻝﺍ ﻲﻗﺭﺃ ﻥﻤ ﺭﺒﺘﻌﺘ ﺫﺇ ﺎﻬﺘﺴﺍﺭﺩﻝ ﻡﻀﺘ
ﻴ ﺎﻤ ﺏﺭﺎﻘ ﺱﻨﺠ 700
ﻭ ﻉﻭﻨ 1700 . ﺎﻬﻝ ﺓﺭﻴﺒﻜ ﺔﻴﺩﺎﺼﺘﻗﺍ ﺔﻴﻤﻫﺃ ﺔﻴﺭﻫﺯ ﺔﻠﺌﺎﻋ ﺭﺒﻜﺍ ﺙﻝﺎﺜ ﺭﺒﺘﻌﺘ ﺙﻴﺤ
ﺕﺎﻴﻭﻨﻭﻓﻼﻔﻝﺎﺒ ﺔﻴﻨﻏ .
لﻭﻔﻝﺍ ﻭ ﻲﻜﻤﺎﻨﺴﻝﺍ ﻭ ﺢﺒﻠﻝﺍﺍ ﻭ ﻡﻠﺴﻝﺍ ﻭ ﻁﻨﺴﻝﺍ ﺕﺎﺘﺎﺒﻨ ﺎﻬﻋﺍﻭﻨﺃ ﺭﻬﺸﺃ ﻥﻤ ﻭ ﻻﺯﺎﺒﻝﺍ ﻭ
ﺹﻤﺤﻝﺍ و ﺱﻭﺴﻝﺍ ﻕﺭﻋ ﻭ
....
ﺦﻝﺇ . لﺜﻤﺘ ﻲﻫﻭ ﺱﻨﺠ ﺎﻬﻨﻤ ﺭﻜﺩﻨ ﺱﺎﻨﺠﻷﺍ ﻥﻤ ﺭﻴﺒﻜ ﺩﺩﻋ
Acacia
,Alibizia ,Bauhinia, Ceratonia , Cercis, Colivillea, Erythrina, Gliricidia, Labumum, Maackia, Ougeinia, Ononis , .
ﻨ ﺔﻠﻴﺼﻓ ﻰﻠﻋ ﺙﺤﺒﻝﺍ ﺍﺫﻫ ﻲﻓ ﺎﻨﻤﺎﻤﺘﻫﺍ ﺯﻜﺭ ﺕﺎﻴﻝﻭﻘﺒﻝﺍ
) Fabaceae ﺱﻨﺠﻝﺍ ﻡﻀﻴ ﻱﺫﻝﺍ (
ononis ﻭ
ﻱﺫﻝﺍ
ﺭﻬﺘﺸﻴ ﺒ ﺕﺎﺒﻜﺭﻤﻝﺎ ﺔﻴﺩﻴﻨﻭﻓﻼﻔﻝﺍ
. ﻭﻓﻼﻔﻝﺍ ﻥﺃ ﻭﺩﺒﻴ ﺽﺍﺭﻤﺃ ﻥﻤ ﻱﻭﺍﺩﺘﻝﺍ ﻲﻓ ﺎﻤﻬﻤ ﺍﺭﻭﺩ ﺎﻬﻝ ﺕﺍﺩﻴﻨ
ﻭ ﺏﻠﻘﻝﺍ
ﺓﺩﺭﻭﻷﺍ , ﺔﻴﻨﻴﺠﻴﺴﻜﻷﺍ ﺕﻼﻋﺎﻔﺘﻤﻝﺍ ﻉﺍﻭﻨﺃ ﻥﻤ ﺭﻴﺜﻜﻝﺍ ﻊﻤ لﻋﺎﻔﺘﺘ ﻥﺃ ﻥﻜﻤﻴ ] .
[7 ,6
ﺎﻫﺭﻴﻏ ﻭ ﻁﻐﻀﻝﺍ ﻭ ﻥﺎﻁﺭﺴﻝﺍ ﺩﻀ ﺔﻝﺎﻌﻓ ﺕﺎﺒﻜﺭﻤ ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺭﺒﺘﻌﺘ ,
ﺭﺒﺘﻌﺘ ﻭ ﺔﻬﺠ ﻥﻤ ﻩﺫﻫ
ﺔﻠﺌﺎﻋ
Fabaceae ﻫ لﺜﻤﺒ ﺔﻴﻨﻏ
ﺫ ﺕﺎﺒﻜﺭﻤﻝﺍ ﻩ .
ﻤ ﻭ ﺍ ﺔﺴﺍﺭﺩﻝﺎ ﻰﻠﻋ لﻴﻝﺩﻝ ﺎﻬﻝ ﺔﻘﺒﺎﺴﻝ
ﺫ ﺕﺎﻨﻭﻓﻼﻓ ﻊﺒﺭﺃ ﺙﻴﺤﺒ ﻙﻝ
ﻫ ﻲﻓ ﺎﻬﻨﻤ ﺕﻠﺼﻓ ﺩﻗ ﺫ
ﺭﺒﺨﻤﻝﺍ ﺍ ''
ﺭﺒﺨﻤ ﻝﺍ ﻉﺎﻨﻁﺼﺍﻭ ﻲﺘﺎﺒﻨﻝﺍ لﺼﻷﺍ ﺕﺍﺫ ﺔﻴﻌﻴﺒﻁﻝﺍ ﺕﺍﻭﺭﺜﻝﺍ ﻥﻴﻤﺜﺘ ﺕﺎﺒﻜﺭﻤ
ﺎﻴﺠﻭﻝﻭﻴﺒ ﺔﻝﺎﻌﻔﻝﺍ ''
ﺔﻨﻴﻁﻨﺴﻗ ﻱﺭﻭﺘﻨﻤ ﺔﻌﻤﺎﺠ ﺀﺎﻴﻤﻴﻜﻝﺍ ﻡﺴﻘﺒ ]
[8 .
3
ﺔﻤﺘﺎﺨ ﻭ لﻭﺼﻓ ﺔﻌﺒﺭﺃ ﻰﻝﺇ ﺔﻝﺎﺴﺭﻝﺍ ﻩﺫﻫ ﻡﻴﺴﻘﺘ ﻡﺘ ﺩﻗ ﻭ :
ﺼﻔﻝﺍ ﻲﻓ • ﺔﺴﺍﺭﺩ ﻪﻴﻓ ﺕﻤﺘ لﻭﻷﺍ ل
ﺔﻴﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺕﺎﺒﻜﺭﻤﻝﺍ .
ﺔﺴﺍﺭﺩ ﻪﻴﻓ ﺕﻤﺘ ﻲﻨﺎﺜﻝﺍ لﺼﻔﻝﺍ ﻲﻓ • ﻕﺭﻁ
ﻭ لﺼﻓ ﻜﺭﻤﻝﺍ ﺔﺴﺍﺭﺩ
ﺔﻴﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺕﺎﺒ .
ﺙﻝﺎﺜﻝﺍ لﺼﻔﻝﺍ ﻲﻓ • ﻪﻴﻓ ﺕﻤﺘ
ﺔﺘﺒﻨﻠﻝ ﺔﻴﺌﺎﻴﻤﻜﻝﺍﻭ ﺔﻴﺘﺎﺒﻨﻝﺍ ﺔﺴﺍﺭﺩﻝﺍ .
ﻪﻴﻓ ﺕﻌﻀﻭ ﻊﺒﺍﺭﻝﺍ لﺼﻔﻝﺍ ﻲﻓ • ﺞﺌﺎﺘﻨﻝﺍ
ﺔﻋﻭﺒﺘﻤ ﺎﻬﻴﻠﻋ لﺼﺤﺘﻤﻝﺍ ﺒ
ﺔﻴﻭﻴﻨﺒﻝﺍ ﻎﻴﺼﻝﺍ ﺩﻴﺩﺤﺘ
ﻤﻠﻝ ﺕﺎﺒﻜﺭ ﺔﻴﻔﻴﻁﻝﺍ ﻕﺭﻁﻝﺍ لﺎﻤﻌﺘﺴﺈﺒ ﺔﻝﻭﺼﻔﻤﻝﺍ
) (UV ,RMN
ﺔﻤﺘﺎﺨﻝﺍ ﺍﺭﻴﺨﺃ ﻭ • :
ﺙﺤﺒﻝﺍ ﺍﺫﻫ ﺞﺌﺎﺘﻨ ﻪﻴﻓ ﺎﻨﻤﻴﻗ .
4
ﻊﺟﺍﺮﳌﺍ
[1] Cooper, E. (2004). Evid. based complement altern. med.1, 215-217.
[2] Tsao, G. C. I., Zeltzer, L. K. (2005). Evid. based complement altern med.2, 149-159.
[3] Solecki, R., Shanidar, I.V. (1975). A Neanderthal flower burial in northern Iraq, Science, 190, 880-881.
[4] Bensky, D., Gamble, A. (1993). Chinese herbal medicine, materia medica, revised edition, Seattle, W.A. Eastland press, Inc. 13-17.
[5] Farnsworth, N. R., Morris, R.W. (1976). Am. J. pharm. Sci. support public health. 148, 46-52.
[6] Remesy, C., Manach, C., Demigne, C., Texier, O., Regerat, F. (1998), « Polyphenols 96», Edition INRA, Paris, 251-265.
[7] Erlund, I. (2004). Nutrition Research, 24, 851–874.
[8] Bouheroum, M., Zaiter, L., Benayache, S., Benayache, F., Bermejo, J. B., Leon, F., Garcia, V. (2009). Chemistry of Natural Compounds, 45, 6.
5
آا ـــــــــ
ا ت ـــ
ـــــ
6
A C B
1 2
4 3 5
6 7
8
1'
2' 3'
4' 6' 5'
O
O
I ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝﺍ – :
ﺎﻬﻔﻴﺭﻌﺘ
•:
ﻨ ﻥﻤ ﺔﻴﻌﻴﺒﻁ ﺕﺎﺒﻜﺭﻤ ﻥﻋ ﺓﺭﺎﺒﻋ ﻲﻫ ﻑﻠﺘﺨﻤ ﻲﻓ ﺩﺠﺍﻭﺘﺘ ﺔﻴﺘﺎﺒﻨ ﺕﺎﻐﺒﺼ ﻲﻫ ﻭ ،ﻱﻭﻨﺎﺜﻝﺍ ﺽﻴﻷﺍ ﺞﺘﺎ
ﺔﺘﺒﻨﻝﺍ ﺀﺍﺯﺠﺃ )
ﺭﺎﻫﺯﺃ ،ﻕﺍﺭﻭﺃ ،ﺭﻭﺫﺠ (
.
ﻤﺴﺇ ﻕﺘﺸﺃ ﺎﻬ
ﻥﻤ flavus ﻥﻤ ﺓﺭﻴﺒﻜ ﺔﻋﻭﻤﺠﻤﻝ ﻡﺎﻌﻝﺍ ﺢﻠﻁﺼﻤﻝﺍ ﻭﻫﻭ ،ﺔﻴﻨﻴﺘﻼﻝﺍ ﻲﻓ ﺭﻔﺼﺃ ﻲﻨﻌﺘ ﻲﺘﻝﺍ
ﺕﺎﺒﻜﺭﻤﻝﺍ ﻡﻝﺎﻌﻝﺍ لﺒﻗ ﻥﻤ ﺓﺭﻤ لﻭﻷ ﺕﻓﺭﻋ ﻲﺘﻝﺍ ﺔﻴﻝﻭﻨﻴﻔﻝﺍ
"
Albert Szent-györgyi
"
ﻝﺍ ﻭ ﺫ ﻥﻴﻤﺎﺘﻴﻓ ﺎﻬﻨﺃ ﺱﺎﺴﺃ ﻰﻠﻋ ﺎﻬﻔﻨﺼ ﻱ ] P
[1 ، ﺙﻴﺤ ﻲﺌﺍﻭﻬﻝﺍ ﻡﺴﻘﻝﺍ ﻲﻓ ﺔﻴﻝﺎﻋ ﺯﻴﻜﺍﺭﺘﺒ ﺩﺠﺍﻭﺘﺘ ﺕﺎﺒﻨﻠﻝ
.
،ﺭﻭﺫﺒﻝﺍ ﺕﺎﻴﺴﺎﻜ ﺩﻨﻋ ﺭﺎﺸﺘﻨﻻﺍ ﺔﻌﺴﺍﻭ ﻲﻫ ﻭ ،ﺎﻬﻨﻤ ﺔﻴﻗﺍﺭﻝﺍ ﺔﺼﺎﺨ ﺔﻴﺘﺎﺒﻨﻝﺍ ﻑﺎﻨﺼﻷﺍ ﻡﻅﻌﻤ ﻲﻓ ﺩﺠﻭﺘ ﺍ ﺔﻁﺴﻭﺘﻤ ﺏﻝﺎﺤﻁﻝﺍ ﺩﻨﻋ ﺔﻤﺩﻌﻨﻤ ﻪﺒﺸ ﻭ ﺭﻭﺫﺒﻝﺍ ﺕﺎﻴﺭﺎﻋ ﺩﻨﻋ ﺭﻭﻀﺤﻝ
] [2 ﺕﺎﻴﺯﺍﺯﺤﻝﺍ ﺩﻨﻋ ﺕﺩﺠﻭ ﺎﻤﻜ ]
[3 ،
ﻥﻴﺘﻘﻠﻔﻝﺍ ﺕﺍﻭﺫﻝ ﺔﻴﺼﻴﺨﺸﺘ ﺓﺍﺩﺄﻜ ﺭﺒﺘﻌﺘ ﻭ ،ﺔﻘﻠﻔﻝﺍ ﺔﻴﺩﺎﺤﺃ ﺕﺎﺘﺎﺒﻨ ﺩﻨﻋ ﻙﻝﺫﻜ ]
.[2
ﺔﻠﺼﻴﻭﺤ ﻲﻓ ﺓﺯﻜﺭﻤﺘﻤ ﺀﺎﻤﻝﺍ ﻲﻓ ﺔﺒﺍﻭﺩ ﺕﺍﺩﻴﺯﻭﺭﺘﻴﺇ ﺓﺭﻭﺼ ﻲﻓ ﺔﻴﺘﺎﺒﻨﻝﺍ ﺔﻴﻠﺨﻝﺍ ﻯﻭﺘﺴﻤ ﻰﻠﻋ ﺩﺠﺍﻭﺘﺘ ﺎﻤﻜ
ﺎﻤﺃ ﺔﻴﻠﺨﻝﺍ ﺍ
لﺤﻨﺘ ﻲﺘﻝﺍ ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝ ﺔﻴﺒﻁﻘﻝﺍ ﺭﻴﻏ ﺕﺎﺒﻴﺫﻤﻝﺍ ﻲﻓ
) ﺎﻜ لﻴﺴﻜﻭﺘﻴﻤﻝﺍ ﺓﺩﻴﺩﻋ ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝ (
ﺩﺠﺍﻭﺘﺘﻓ ﻲﻓ ﺎﻤﺯﻼﺒﻭﺘﻴﺴ ﺔﻴﻠﺨﻝﺍ
] [4 ، ﺕﺎﻨﻭﻜﻴﻠﺠﺃ ﺓﺭﻭﺼ ﻲﻓ ﺎﻫﺩﻭﺠﻭ ﺔﻝﺎﺤ ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﻊﻀﻭﺘﺘﻭ
) (aglycones ﺔﻴﻠﻴﻓﻭﺒﻴﻝ ﻯﺭﺨﻷﺍ ﻲﻫ ﺓﺯﺭﻔﻤ ﺩﺍﻭﻤﻝ ﺔﻤﺯﻼﻤ ﻥﻭﻜﺘ ﺙﻴﺤ ﻕﺍﺭﻭﻸﻝ ﺔﻴﺤﻁﺴﻝﺍ ﺔﺠﺴﻨﻷﺍ ﻰﻠﻋ
ﺔﻓﺎﺠﻝﺍ ﻪﺒﺸ ﻭ ﺔﻓﺎﺠﻝﺍ ﻕﻁﺎﻨﻤﻝﺍ ﺕﺎﺘﺎﺒﻨ لﺎﺤ ﻭﻫﻭ ]
[5
، ﺕﺎﺘﺎﺒﻨﻝﺍ ﻲﻓ ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺏﻠﻏﺃ ﺩﺠﻭﺘ ﺎﻤﻭﻤﻋ ﻭ
ﻲﻤﺤﻤ لﻜﺸﺒ )
ﺕﺍﺩﻴﺯﻭﺭﺘﻴﺇ (
ﺔﺘﻴﻤﻝﺍ ﺔﻴﺘﺎﺒﻨﻝﺍ ﺔﺠﺴﻨﻷﺍ ﻲﻓ ﺕﺎﻨﻭﻜﻴﻠﺠﻷﺍ ﺩﺠﻭﺘ ﺎﻤﻨﻴﺒ )
ﻲﻀﻤﺤﻝﺍ ﻪﻴﻤﺘﻝﺍ ﺔﺠﻴﺘﻨ
ﺕﺎﻤﻴﺯﻨﻹﺍ ﺔﻁﺴﺍﻭﺒ ﺯﻔﺤﻤﻝﺍ (
ﺭﺎﺠﺸﻷﺍ ﺏﺸﺨ ﻲﻓ ﻙﻝﺩﻜ ﻭ .
] [4
ﻊﻴﻤﺠ ﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺕﺍ
ﻰﻠﻋ ﻱﻭﺘﺤﺘ لﻜﺸﻝﺍ ﻰﻠﻋ ﺔﻋﺯﻭﻤ ﻲﺴﺎﺴﻷﺍ ﺎﻬﻠﻜﻴﻫ ﻲﻓ ﻙﻝﺫ ﻭ ﻥﻭﺒﺭﻜ ﺓﺭﺫ 15
C6-C3-C6 ﻥﻴﺯﻨﺒﻝﺍ ﺎﺘﻘﻠﺤ لﺼﺘﺘ ﺙﻴﺤﺒ
"A"
ﻭ
"B"
ﺔﺴﻨﺎﺠﺘﻤ ﺭﻴﻏ ﺔﻘﻠﺤﺒ
"C"
ﺭﺼﻨﻋ ﻰﻠﻋ ﻱﻭﺘﺤﺘ
ﻥﻴﺠﺴﻜﻷﺍ ].
[4
لﻜﺸﻝﺍ - -1 لﻜﻴﻬﻝﺍ ﻥﻴﺒﻴ ﻡﺎﻌﻝﺍ
ﻝ ﺩﻴﻨﻭﻓﻼﻔﻠ ﺕﺍ
.
-
لﻜﺸ
- 1
7
ﺎﻨﻫ ﻥﺃ ﺎﻤﻜ لﺜﻤ ﺕﺎﻨﻭﻓﻼﻓﻭﺯﻴﻹﺍ ﻲﻫﻭ ﺕﺎﻨﻭﻓﻼﻔﻠﻝ ﻲﺌﺎﻨﺒﻝﺍ ﺏﻴﻜﺭﺘﻝﺎﺒ ﺔﻠﺼﻝﺍ ﺔﻘﻴﺜﻭ ﺔﻴﻌﻴﺒﻁ ﺕﺎﺠﺘﻨﻤ ﻙ
:
) (Formononetine
لﻜﺸﻝﺍ ﻲﻓ ﺎﻤﻜ )
(2 ﻩﺎﻨﺩﺃ
، ﻭ ﺭﺘﺴﺇ ﺕﺎﺒﻜﺭﻤ ﻥﻋ ﺓﺭﺎﺒﻋ ﻲﻫﻭ ﺔﻴﺘﺎﻔﻠﺴ ﺕﺍﺩﻴﻭﻨﻭﻓﻼﻓ
لﻭﻨﻭﻓﻼﻔﻝﺍﻭﺃ ﻥﻭﻓﻼﻔﻝﺍ ﺕﻼﻴﺴﻜﻭﺭﺩﻴﻫ ﻥﻤ ﺩﻴﺩﻌﻠﻝ ﻲﺘﺎﻔﻝﻭﺴ (kaempferole)
ﺔﻴﺭﻴﺜﻴﻹﺍ ﻡﻬﺘﻼﻴﺜﻤ ﻭﺃ
، ﻲﻫﻭ
ﻊﺴﺍﻭ ﻕﺎﻁﻨ ﻰﻠﻋ ﺓﺭﺸﺘﻨﻤﻝﺍ ﺕﻻﻭﻨﻭﻓﻼﻔﻝﺍ ﻭ ﺕﺎﻨﻭﻓﻼﻔﻝﺍ ﻑﻼﺨﺒ ﺔﻌﻴﺒﻁﻝﺍ ﻲﻓ ﺍﺭﺎﺸﺘﻨﺇ لﻗﺃ .
] [6
Kaempferole Formononetine
-
لﻜﺸ
2 –I – I
ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻠﻝ ﻱﻭﻴﺤﻝﺍ ﻉﺎﻨﻁﺼﻻﺍ :
ﺩﻴﺴﻜﺃ ﻲﻨﺎﺜ ﻭ ﺀﺎﻤﻝﺎﻜ ،ﺔﻴﺴﺎﺴﻷﺍ ﺕﺍﺩﺤﻭﻝﺍ ﻥﻤ ﺔﻋﻭﻤﺠﻤ ﻰﻠﻋ ﺔﻴﻌﻴﺒﻁﻝﺍ ﺎﻬﺘﺎﺠﺘﻨﻤ ﻉﺎﻨﻁﺼﺍ ﻲﻓ ﺔﻴﻠﺨﻝﺍ ﺩﻤﺘﻌﺘ ﺔﻠﻴﺴﻷﺍ ،ﺔﻠﻜﻝﻷﺍ ،لﺍﺯﺘﺨﻻﺍ ،ﺓﺩﺴﻜﻷﺍ ﺕﻼﻋﺎﻔﺘ ﺭﺒﻋ لﺨﻝﺍ ﺽﻤﺤ ﻭ ،لﻤﻨﻝﺍ ﺽﻤﺤ ،ﻥﻭﺒﺭﻜﻝﺍ ...
ﺦـﻝﺍ . ﻭ
ﻙﻝﺫ ﻡﺘﻴ ﻙﻝﺫﻝ ﺔﺼﺎﺨ ﺕﺎﻤﻴﺯﻨﺇ ﺩﻭﺠﻭﺒ .
ﻨﺍ ﺙﻴﺤ ـﺒ ﺔﻤﻭﺴﻭﻤﻝﺍ ﺭﺌﺎﻅﻨﻝﺍ لﺎﻤﻌﺘﺴﺎﺒ ﻙﻝﺫ ﻭ ﺓﺩﻴﺩﻋ ﺏﺭﺎﺠﺘ ﺀﺍﺭﺠﺇ ﻡﺘ ﻪ
14C ﻅـﺤﻻ ﺩـﻘﻓ ،ﻊﺸـﻤﻝﺍ
ﺙﺤﺎﺒﻝﺍ
" Robinson "
ﺔﻨﺴ ] 1936 [7
ﺱـﻔﻨ ﺎـﻤﻬﻝ ﺱﻴـﻝ ﺔﻴﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺕﺎﺒﻜﺭﻤﻠﻝ ﺔﻴﻨﻴﺯﻨﺒﻝﺍ ﻥﻴﺘﺍﻭﻨﻝﺍ ﻥﺃ
ﺔﺜﻼﺜ لﻼﺨ ﻡﺘﺘ ﻱﻭﻴﺤﻝﺍ ﻉﺎﻨﻁﺼﻻﺍ ﺔﻴﻠﻤﻋ ﻥﺈﻓ ﻪﻴﻠﻋ ﻭ ﻱﻭﻴﺤﻝﺍ ﻲﺜﺍﺭﻭﻝﺍ لﺼﻷﺍ ﻕﺭﻁ
:
I I –
-
1ﻕﻴﺭﻁ ﻙﻴﻤﻴﻜﻴﺸﻝﺍ
:
ﺙﺤﺎﺒﻝﺍ ﻥﺃ ﺙﻴﺤ ﻰﻝﻭﻷﺍ ﺔﻠﺤﺭﻤﻝﺍ ﻲﻫ ﻭ
" Davis "
ﺔﻨﺴ ﺕﺒﺜﺃ ] 1955
[8 ﻲـﻓ ﻙﻴﻤﻴﻜﻴﺸـﻝﺍ ﺽﻤﺤ ﺭﻭﺩ
ﻘﻠﺤﻝﺍ ﻥﻴﻭﻜﺘ ـ
ﺔ ﺔﻴﺜﻼﺜﻝﺍ ﺔﻴﻨﻭﺒﺭﻜﻝﺍ ﺔﻠﺴﻠﺴﻝﺍ ﻙﻝﺫﻜ ﻭ B C3
ﻲـﻓ ﻥﻴـﺒﻤ ﻭﻫ ﺎﻤﻜ ،ﺯﻭﻜﻭﻠﻐﻝﺎﺒ ﺍﺀﺩﺒ ﻙﻝﺫ ﻭ
لﻜﺸﻝﺍ - -3 :
8
+ 1 = 2
OH OH HO
O COOH
PO HO COOH
OH
O OH
O OH
OH COOH
OH OH COOH
HO COOH
PO
OH OH
COOH
OH
PO O C
COOH CH2
OH COOH
O C
COOH CH2
OH
CH2COCOOH HOOC
OH CH2
OH CH2 H2N COOH
OH HC CH
COOH
COCOOH 4-Phosphate
erythrose
Ac.Phosphate pyruvique
Ac.2-Ceto-3-desoxy-7- phosphoglucoheptoni que
Ac.5-Dehydroqu inique
Ac.5-Déhydroshikimique Ac.Shikimique
Ac.5-Phophoshikimique
ADP+Pi ATP
Ac.3-Enolpyruvyl-5- phosphoshikimique
Ac.Chorismique Ac.Prephénique
H+
CO2
Ac.p-Hydroxyphenyl pyruvique
Ac.p-Hydoxyphenyl alanine
Ac.p-Hydroxycinnamique (Ac.p-coumarique)
CHO CHOH CHOH CH2OP
COOH COP CH2
COOH CO CH2
CHOH CHOH CHOH CH2OP
3
H2O
5 4
6
7
8
9
H2O Pi Pi
10
Pi
- -3 Coumarique
- P . ا Ac ا ارو" ز آ $%ا &" '(
9
OH
HOOC
Ac.P-coumarique P-coumaroyl CoA
OH
O CoAs
CoA
ﻲﻓ لﺜﻤﺘﻤﻝﺍ ﻭ ﺞﺘﺎﻨﻝﺍ لﻭﺤﺘ ﻪﻴﻠﻴ Ac.4-coumaroyl
) Ac.P-Coumarique (
ﻰﻝﺇ
4-coumaroyl-CoA ﻊﻤ ﺩﺎﺤﺘﻼﻝ ﺍﺯﻫﺎﺠ ﻥﻭﻜﻴ ﻱﺫﻝﺍ
Malonyl-CoA ﺔﻤﺩﺎﻗ ﺔﻠﺤﺭﻤ ﻲﻓ
.
- -4
لﻭﺩﺠ - -1 ﺽﻤﺤ ﻥﻴﻭﻜﺘ ﻲﻓ ﺔﻠﺨﺍﺩﻝﺍ ﺕﺎﻤﻴﺯﻨﻹﺍ ﺔﻤﺌﺎﻗ arique
Coum -
p .
Ac
)*+ا )'ا
Aldolase, 3-désoxy-O-arabinoheptulosonate-7-phosphate synthase ou DHAP synthase
1
Déshydroquinate synthase
2
Déshydroquinate déshydratase
3
Shikimate déshydrogénase
4
Complexe shikimate kinase
5
Ac.Phosphate pyruvique
6
Chorismate mutase
7
Préphénate déshydrogénase
8
Aminitrensférases
9
Tyrosine ammonia-lyase
10
لﻭﺩﺠ
- -1 ﺽﻤﺤ ﻥﻴﻭﻜﺘ ﻲﻓ ﺔﻠﺨﺍﺩﻝﺍ ﺕﺎﻤﻴﺯﻨﻹﺍ Coumarique
- p .
Ac
10
O
H3C SCoA OH
O O
SCoA
O HO OH
OH
OH CO2
ATP ADP
Malonyl
+
CoA
S-CoA 3 x
OH
HOOC
OH
O CoAS CoA
OH
O O
OH
O CoAS
synthese chalkone
-II
-
2ﺕﻼﺨﻝﺍ ﻕﻴﺭﻁ :
ﺔﻘﻠﺤﻝﺍ ﺱﺃﺭ ﻑﺜﺎﻜﺘ ﻥﻤ لﻜﺸﺘﺘ A
– لﻜﺸ ﻰﻠﻋ ﺕﻼﺨﻝﺍ ﻥﻤ ﺕﺍﺩﺤﻭ ﺙﻼﺜﻝ لﻴﺫ
Malonyl-CoA
ﺽﻤﺤ ﻊﻤ
Ac.P-Coumarique
. ﻡﻗﺭ لﻜﺸﻝﺍ -
-5 ] . -4 -6 [7
لﻜﺸﻝﺍ
– -5 ﻥﻭﻜﻝﺎﺸﻝﺍ ﻥﻴﻭﻜﺘ
I
-
I-
3ﻥﻭﻜﻝﺎﺸﻝﺍ ﻕﻴﺭﻁ :
ﺭﺩﺤﻨﺘ ﻲﺘﻝﺍ ﺔﻴﺴﻴﺌﺭﻝﺍ ﺓﺍﻭﻨﻝﺍ ﻥﻭﻜﻝﺎﺸﻝﺍ ﺭﺒﺘﻌﻴ ﺕﻴﺤ ،ﺔﺜﻝﺎﺜﻝﺍ ﺔﻠﺤﺭﻤﻝﺍ ﻲﻫ ﻭ
ﺔﻴﺩﻴﻭﻨﻭﻓﻼﻔﻝﺍ لﻜﺎﻴﻬﻝﺍ ﻑﻠﺘﺨﻤ ﺎﻬﻨﻤ
11
لﻜﺸﻝﺍ - -6 ﻥﻭﻜﻝﺎﺸﻝﺍ ﻥﻤ ﺎﻗﻼﻁﻨﺍ ﺔﻴﺩﻴﻭﻨﻭﻓﻼﻔﻝﺍ لﻜﺎﻴﻬﻝﺍ ﻑﻠﺘﺨﻤﻝ ﻱﻭﻴﺤﻝﺍ ﻉﺎﻨﻁﺼﻹﺍ
CAos
O
CAos
O
OCAs
O
Carbohydrates
shikimate
arogenate
phenylalanine cinnamate
4-coumarate 4-coumamoyl-CoA
3-malonyl-CoA acetyl-CoA
isoliquiritigénine VI III
1+2 I
II
1
O OH
HO O
OH
naringenin
O OH
HO O
OH
apigenin
OH
O OH
HO O
OH
dihydrokaempf erol
O OH
H O O
OH
genistein
OH
O OH
HO O
OH
kaempf erol
O OH HO
OH
3 4 5
Apif orl Apipenidine-5-O-glucoside
OH
OH OH
HO O
OH
OH
OH
HO O
OH
OH
OH
HO O
OH
O- Glu
OH
HO O
OH
OH
OH
HO O
OH
OH
OH OH
HO O
OH OH
7 6a 6b
10 11
9 8
12
13
14
15
leucopelargonidine
pelaronidine
pelargoinid 3-glucoside
propelagonidin B-3
12
لﻭﺩﺠﻝﺍ –
-2 ﻯﻭﻴﺤﻝﺍ ﻊﻴﻨﺼﺘﻝﺍ ﻲﻓ ﺔﻠﺨﺍﺩﻝﺍ ﺕﺎﻤﻴﺯﻨﻹﺍ ﺔﻤﺌﺎﻗ ﻥﻴﺒﻴ :
)'ا )*+ا
) ACRONYME (
./ا "0ا
) CO-FACTEUR (
Acétyl-CoA I Non
II Phénylalanine ammonia-lyase(PAL)
Non
Cinnimate 4- hydroxylase (C4H) III NADPH
VI 4-Coumarate:CoA ligase (4CL)
CO-Sh ATP
1 Chalcone synthase (CHS)
Non
2 Polyketide réductase (PKR)
NADPH
3 Chalcone isomérase
Non
4 2-Hydroxyisoflavone synthase (IFS)
NADPH
5 2-Hydroxyisoflavanol déshydrathase
Non
6 6-a Flavone synthase I (FNSI)
NADPH
6 6-b Flavone synthase II (FNSI)
NADPH
7 Flavanone 3-hydroxylase (FHT)
2-Oxoglutarate Fe2+ ascoparate
8 Flavonol synthase (FLS)
2-Oxoglutarate Fe2+ ascoparate
9 Dihydroflavanol 4- réductase (DFR)
NADPH
10 Flavanone 4-réductase (FNR)
NADPH
11 Leucoanthocyanidine 4-réductase
NADPH
12 Anthocyanine synthase (ANS)
Inconnu
13 Flavonoid 3-O-glucosyltransférase
14 Flava-3,4-cis-diol-reductase
Non
15 Anthocyanidine / flavonol 3-O-
glucosyltransférase non
لﻭﺩﺠﻝﺍ
– -2 ﻯﻭﻴﺤﻝﺍ ﻊﻴﻨﺼﺘﻝﺍ ﻲﻓ ﺔﻠﺨﺍﺩﻝﺍ ﺕﺎﻤﻴﺯﻨﻹﺍ
13
+ 0° - 5° NaH
8 Jours H
O
O Me
HO OH
OH
MeO HO
O Me
III
ﻱﺭﺒﺨﻤﻝﺍ ﻉﺎﻨﻁﺼﻻﺍ
- ]:
[2
-
III-
1ﻥﻭـﻜﻝﺎﺸﻝﺍ ﻊﻴﻨﺼﺘ
]:
[2
ـﻝ ﻲﻝﻭﺩﻝﻷﺍ ﻑﺜﺎﻜﺘﻝﺎﺒ ﻙﻝﺫ ﻭ ﺕﺎﻨﻭﻜﻝﺎﺸﻝﺍ ﻰﻠﻋ لﻭﺼﺤﻝﺍ ﺎﻨﻨﻜﻤﻴ :
2-hydroxyacetophenone
ﺔﻴﺩﻴﻫﺩﻝﻷﺍ ﺔﻴﻨﻴﺯﻨﺒﻝﺍ ﺕﺎﻘﺘﺸﻤﻝﺍ ﻊﻤ )
benzenaldehydes
( ﻁـﺴﻭﻝﺍ ﻲﻓ ﻙﻝﺫ ﻭ
ﻱﺩﻋﺎﻘﻝﺍ ﻭﺃ ﻲﻀﻤﺤﻝﺍ .
لﻋﺎﻔﺘ ﻕﻓﻭ ﻥﻭﻨﺎﻓﻼﻔﻝﺍ ﺭﻭﻬﻅ ﻰﻝﺇ ﻱﺩﺅﻴ ﻱﺫﻝﺍ ﻲﻀﻤﺤﻝﺍ ﻁﺴﻭﻝﺍ ﻲﻓ ﻙﻝﺫ ﻭ ﻥﻭﻜﻝﺎﺸﻠﻝ ﻕﻠﺤﺘ ﺔﻴﻠﻤﻋ ﺙﺩﺤﺘ ﻥﺯﺍﻭﺘﻤ )
ﻥﻭﻜﻝﺎﺸ - ﻥﻭﻨﺎﻓﻼﻓ (
ﺇ ﻲﻠﻜ ﻪﺒﺸ لﻜﺸﺒ ﺡﺍﺯﻨﻴ ﻥﺯﺍﻭﺘﻝﺍ ﺍﺫﻫ ﻥﺃ ﻻﺇ ، ﻲـﻓ ﺍﺫﻫ ﻭ ﻥﻭﻜﻝﺎﺸﻝﺍ ﺔﻬﺠ ﻰﻝ
ﻊﻗﻭﻤﻝﺍ ﻲﻓ ﺭﺤ لﻴﺴﻜﻭﺭﺩﻴﻫ ﺩﻭﺠﻭ ﺔﻝﺎﺤ ﻥﻭﻜﻝﺎﺸﻠﻝ ﺔﺒﺴﻨﻝﺎﺒ 4
.
ﺔﻴﻝﺎﺘﻝﺍ ﻁﻭﺭﺸﻝﺍ ﺏﻠﻁﺘﻴ ﻱﺩﻋﺎﻘﻝﺍ ﻁﺴﻭﻝﺍ ﻲﻓ لﻋﺎﻔﺘﻝﺍ :
لﻋﺎﻔﺘﻝﺍ ﺓﺭﺍﺭﺤ ﺔﺠﺭﺩ
ﺓﺩﻋﺎﻘﻝﺍ ﺯﻴﻜﺭﺘ
لﻋﺎﻔﺘﻠﻝ ﻡﺯﻼﻝﺍ ﻥﻤﺯﻝﺍ
°0 ﻡ –
° 20 ﻡ KOH
%50 -
%60 -15
ﺔﻋﺎﺴ 48
ﻴﺜﻤﻝﺍ ﺕﺎﻋﻭﻤﺠﻤ ﻡﺍﺩﻌﻨﺍ ﻥﺃ ﻅﺤﻭﻝ ﺩﻗ ﻭ ﺩﻴﺠ ﺩﻭﺩﺭﻤ ﻰﻝﺇ ﻱﺩﺅﻴ ل
لﻜﺸﻝﺍ ﺏﺴﺤ . 7
لﻜﺸﻝﺍ
- -7
14 Zn AcOH anhy OH
O
OH
O
ﻲﻓ ﺔﻘﻠﺤﻝﺍ ﺢﺘﻔﺒ ﻙﻝﺫ ﻭ ﻥﻭﻨﺎﻓﻼﻔﻝﺍ ﻥﻤ ﺎﻗﻼﻁﻨﺍ لﻴﺜﻤﻝﺍ ﺕﺎﻋﻭﻤﺠﻤ ﺕﺍﺫ ﺕﺎﻨﻭﻜﻝﺎﺸﻝﺍ ﻰﻠﻋ لﻭﺼﺤﻝﺍ لﺠﺃ ﻥﻤ ﺩﻭﺩﺭﻤ ﻰﻠﻋ لﻭﺼﺤﻠﻝ ﻭ ﺔﻀﻔﺨﻨﻤ ﺓﺭﺍﺭﺤ ﺕﺤﺘ ﻭ ﺩﺩﻤﻤﻝﺍ ﺽﻤﺤﻝﺎﺒ ﺏﻴﺴﺭﺘﻝﺍ ﻡﺜ ﻲﻝﻭﺤﻜﻝﺍ ﻱﺩﻋﺎﻘﻝﺍ ﻁﺴﻭﻝﺍ ﺴﻜﻭﺭﺩﻴﻫ ﺩﻭﺠﻭ ﻡﺩﻋ ﻲﻐﺒﻨﻴ ﺩﻴﺠ ﻊﻀﻭﻝﺍ ﻲﻓ ﺭﺤ لﻴ
ﻥﻭﻨﺎﻓﻼﻔﻠﻝ ﺔﺒﺴﻨﻝﺎﺒ 5 .
-III -2 ﻥﻭﻜﻝﺎﺸﻭﺭﺩﻴﻫ ﻲﺌﺎﻨﺜ ﻊﻴﻨﺼﺘ ]
:
[2
ﻭﺭﺩـﻴﻫ ﻲﺌﺎـﻨﺜ ﺽـﻤﺤ ﺕﺎﻘﺘﺸـﻤ ﻊﻤ ﺕﻻﻭﻨﻴﻔﻝﺍ ﻑﺜﺎﻜﺘ ﻥﻤ ﻙﻝﺫﻭ ﻥﻭﻜﻝﺎﺸﻭﺭﺩﻴﻫ ﻲﺌﺎﻨﺜ ﻰﻠﻋ لﺼﺤﺘﻨ ﻙﻴﻤﺎﻨﻴﺴ )
acide dihydrocinnamique
( ﻥﻭﻨﺎﻓﻼﻔﻝﺍ ﻭﺃ ﻥﻭﻜﻝﺎﺸﻝﺍ ﺔﺠﺭﺩﻬﺒ ﻭﺃ لﻜﺸﻝﺍ ﺏﺴﺤ
.8
لﻜﺸﻝﺍ
8 - -
15
-III
-
3ﻥﻭﺭﻭﻷﺍ ﻭ لﻭﻨﻭﻓﻼﻔﻝﺍ ﻊﻴﻨﺼﺘ
]:
[2
NaOH
لﻜﺸﻝﺍ
9 - -
ﻻﺩﺒﺘﺴﻤﻝﺍ ﺩﻭﺠﻭ ﻭ لﻋﺎﻔﺘﻝﺍ ﻁﻭﺭﺸ ﻥﺃ ﻅﺤﻭﻝ ﺔﺒﺴـﻨﻝﺎﺒﻓ ،لـﻋﺎﻔﺘﻝﺍ ﺔـﻴﺩﻭﺩﺭﻤ ﻰـﻠﻋ ﺭـﻴﺒﻜ ﺭﻴﺜﺄﺘ ﺎﻬﻝ ﺕ
ﻊﻗﻭﻤﻝﺍ ﻲﻓ لﻴﺴﻜﻭﺭﺩﻴﻫ ﺩﻭﺠﻭ ﻥﺃ ﻅﺤﻭﻝ ﺕﻻﺩﺒﺘﺴﻤﻠﻝ ﻊﻗﻭﻤﻝﺍ ﻭ 2
لﻴﺴـﻜﻭﺘﻴﻤ ﺔﻋﻭﻤﺠﻤ ﻰﻝﺇ ﺔﻓﺎﻀﻹﺎﺒ 4
ﻊﻀﻭﻤﻝﺍ ﻲﻓ
´6 ﺏﻭﻠﻁﻤﻝﺍ لﻭﻨﻭﻓﻼﻔﻝﺍ ﻰﻠﻋ لﻭﺼﺤﻝﺍ ﻩﺎﺠﺘﺎﺒ ﺩﻴﺯﻴ لﻋﺎﻔﺘﻝﺍ ﺩﻭﺩﺭﻤ ﻥﺈﻓ .
ﺔﻴﻝﺎﺜﻤﻝﺍ ﻁﻭﺭﺸﻝﺍ :
H2O2 %5
30 -
% ، 20 NaOH
%
-
III-
4ﻥﻭﺭﻭﻷﺍ ﻊﻴﻨﺼﺘ
]:
[2
ﻲـﻓ ﺔﻴﺭﻁﻌﻝﺍ ﺕﺍﺩﻴﻫﺩﻝﻷﺍ ﻊﻤ ﻥﻴﺭﺎﻤﻭﻜﻝﺍ ﻑﺜﺎﻜﺘ ﻰﻠﻋ ﺎﺴﺎﺴﺃ ﺩﻤﺘﻌﺘ ﺎﻬﻠﻜ ﺎﺒﻴﺭﻘﺘ ﺔﻠﻤﻌﺘﺴﻤﻝﺍ ﺔﻴﻠﻤﻌﻝﺍ ﻕﺭﻁﻝﺍ ﺏـﻠﻁﺘﺘ ﻲﺘﻝﺍ ﺔﻘﻴﺭﻁﻝﺍ ﻩﺫﻫ لﺎﻤﻌﺘﺴﺍ ﻥﻜﻤﻴ ﻻ ﺕﻻﺩﺒﺘﺴﻤﻜ ﺕﺎﻴﺭﻜﺴ ﺩﻭﺠﻭ ﺔﻝﺎﺤ ﻲﻓ ﻪﻨﺃ ﻻﺇ ﻲﻀﻤﺤ ﻁﺴﻭ ﺽﻤﺤ ﺩﻭﺠﻭ ﻯﺭﺨﺃ ﺕﻼﻋﺎﻔﺘ ﻰﻝﺇ ﺄﺠﻠﻨ ﺎﻨﻨﺈﻓ ﺍﺫﻝ HCl
.
OH
O
O
O
OH
O
O
H2O2
16
لﻜﺸﻝﺍ
10 - -
-
IVﻱﺩﻴﻨﻭﻓﻼﻔﻝﺍ لﻜﻴﻬﻝﺍ ﻰﻠﻋ ﺔﻴﻝﺍﺩﺒﺘﺴﻹﺍ ﺕﺎﻋﻭﻤﺠﻤﻝﺍ ﺕﻴﺒﺜﺘ :
لﻴﺴﻜﻭﺭﺩﻴﻬﻝﺍ ﺕﺎﻋﻭﻤﺠﻤ ﺕﻴﺒﺜﺘ ﻥﺇ ,
ﺭﻜﺴﻝﺍ ﻭﺃ لﻴﺴﻜﻭﺘﻴﻤﻝﺍ ,
ﻉﺎﻨﻁﺼﻻﺍ ﺔﻴﺎﻬﻨ ﺩﻨﻋ ﻡﺘﻴ ﺔﻤﺎﻋ ﺓﺭﻭﺼﺒ
ﺜﺅﺘ ﻻﻭ ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺽﻌﺒ ﻲﻓ ﺭﺜﺅﺘ ﺕﺎﻋﻭﻤﺠﻤﻝﺍ ﻩﺫﻫ ﺕﻴﺒﺜﺘ ﺔﻴﻠﻤﻋ ﻥﻷ ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻠﻝ ﻱﻭﻴﺤﻝﺍ ﺭ
ﻰﻠﻋ
ﻵﺍ ﺽﻌﺒﻝﺍ ﺭﺨ
9] . [
-
IV-
1ﺘ
ﺘ ﺠﻤ ﺕﻴﺒﺜﺠﻤ ﺕﻴﺒﺜ ﻤ
ﻤلﻴﺴﻜﻭﺭﺩﻴﻬﻝﺍ ﺔﻋﻭ
لﻴﺴﻜﻭﺭﺩﻴﻬﻝﺍ ﺔﻋﻭ
: :10] [
ﺇ ﺕﻴﺒﺜﺘ ﻥ ﺔﻴﻠﻴﺴﻜﻭﺭﺩﻴﻬﻝﺍ ﺕﺎﻋﻭﻤﺠﻤﻝﺍ
ﻭﻤﻝﺍ ﻲﻓ ﻀ ﻥﻴﻌ ﻭ 5 ﺒﻗ ﻡﺘﻴ 7 ل ﺔﻘﻠﺤﻝﺍ لﻴﻜﺸﺘ
، A ﺍﺫﻬﻝ ﻭ ﻲﻬﻓ
ﻌﺘ ﺘ ﻤﺠﻤ ﺭﺒ ﺔﻴﻠﺼﺃ ﺕﺎﻋﻭ
، ﻷﺍ ﺱﻔﻨ ﺭﻤ
ﺒ ﻝﺎ ﺴﻨ ﻊﻗﻭﻤﻝﺍ لﻴﺴﻜﻭﺭﺩﻴﻬﻝ ﺔﺒ ﺔﻘﻠﺤﻠﻝ 4
. B
ﺜﺘ ﺎﻤﺃ ﺒ ﻓ لﻴﺴﻜﻭﺭﺩﻴﻬﻝﺍ ﺔﻋﻭﻤﺠﻤ ﺕﻴ ﻲ
ﺍ ﻊﻀﻭﻤﻝ ﻡﺘﻴ 3
ﻲﻓ ﻠﺤﺭﻤ ﻭﻜﻝﺎﺸﻝﺍ ﻥﻴﻭﻜﺘ ﺔ ﻥ
ﻋ ﻰﻠ ﺨ ﻼ ﻑ ﻤﻝﺍ ﻭ ﻀ ﻊ
ﻴﻬﻝﺍ ﺔﻋﻭﻤﺠﻤ ﺕﻴﺒﺜﺘ ﻪﻴﻓ ﻡﺘﻴ ﻱﺫﻝﺍ '3 ﺩ
لﻴﺴﻜﻭﺭ ﺒ
ﻥﻭﻜﻝﺎﺸﻝﺍ ﺔﻠﺤﺭﻤ ﺩﻌ ﺔﻘﻠﺤﻝﺍ ﻕﻠﻏ ﺩﻌﺒ ﻱﺃ
. C
-
IV-
2ﺘ
ﺘ ﺠﻤ ﺕﻴﺒﺜﺠﻤ ﺕﻴﺒﺜ ﻋﻭﻤ
ﻋﻭﻤﺔ
ﺔ ﻴﺜﻤﻝﺍﻴﺜﻤﻝﺍ ل
ل : :ﺇ ﺕﻴﺒﺜﺘ ﻥ ﺍ ﺕﻴﺒﺜﺘ ﺩﻌﺒ ﻲﺘﺄﻴ لﻴﺜﻤﻝﺍ
ﻝ ﺴﻜﻭﺭﺩﻴﻬ ﻴ
ﻥﻴﺘﻝﺎﺤ ﻲﻓ ﻥﻭﻜﻴﻠﺠﻷﺍ لﻜﻴﻫ ﻰﻠﻋ ﺭﻴﺨﻷﺍ ﺍﺫﻫ ﻡﺘﻴ ﻭ ،ل :
CH2 O
C O
CH OH
Glu
O
OH HO
H O
OH Glu
O
OAc
OAc
Ac2O +
17
ﺍ ﻝﻭﻷﺍ ﺔﻝﺎﺤﻝ ﻰ
:
ﺘ ﻥﻭﻜ ﺍ ﺭﻜ ﻥﻴﺒ ﺔﻁﺒﺍﺭﻝ ﻭﺒ
ﻥ ﻝﺍ ﺜﻤ لﻴ ﺒﺭﻜ ﻭ ﻭ ﻥ ﺍ ﻨﻝ ﺍﻭ ﻴﺘ ﻥ ﻭ A ) ﻭﺃ ( ﻭ B ﺜﻤ لﺎ ﻋ ﻰﻠ ﺫ ﻙﻝ ﺏﻜﺭﻤﻝﺍ
O
OH OH
HO
HO
OH
O CH3
8-C-méthylgalangine
ﺍ ﺔﻝﺎﺤﻝ ﺍ ﺔﻴﻨﺎﺜﻝ :
ﻫ ﻲ ﻠﻴﺴﻜﻭﺭﺩﻴﻬﻝﺍ ﺕﺎﻋﻭﻤﺠﻤﻝﺍ ﺔﻴﻠﻴﺜﻤ ﺔﻴ
ﺍ لﺒﻗ ﻥﻤ ﺎﻬﺘﻴﺒﺜﺘ ﻡﺘ ﻲﺘﻝ )
O-methylation
( ﺍﺫﻫ ﻭ ﻓ ﺩﻭﺠﻭ ﻲ
ﻡﻴﺯﻨﺃ O-methyltransférase
ﺎﻤﻜ ﻠﻝ ﺢﻨ ﻴﺜﻤ ل 10] [ ﻭ ﺍ ﻝ ﺸ ﻜ ل ﻲﻝﺎﺘﻝﺍ ﻴﺒ ﻴ ﻥ ﺫﻝ ﻙ .
O O
OH
HO
OH
Lutéoline
O O
OMe
OH
OH HO
Chrysoériol
SAM SAH
OH
SAM: S – adénosyl méthionine SAH: S – adénosyl homocysteine
ـﻝ ﻲﻤﻴﺯﻨﻹﺍ لﻭﺤﺘﻝﺍ
lutéoline ﻝﺇ
ﻰ chrysoériol
18
IV - 3 ﺘ- ﺕﺎﻴﺭﻜﺴﻝﺍ ﺕﻴﺒﺜ
ﺘ ﺕﺎﻴﺭﻜﺴﻝﺍ ﺕﻴﺒﺜ :
:ﺘ ﻤﻝﺍ ﺩﺠﻭ ﺭ
ﻫ ﻰﻠﻋ ﺔﻴﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﺕﺎﺒﻜ ﻴ
ﻜﻴﻠﺠ ﺔﺌ ﻭ ﺔﻴﺭﻜﺴ ﺕﺍﺩﺤﻭ ﻰﻠﻋ ﻱﻭﺘﺤﻴ ﺎﻫﺀﺎﻨﺒ ﻥﺃ ﻱﺃ ،ﺕﺍﺩﻴﺯ
ﺍ ﺀﺎﻨﺒ ﻲﻓ لﺨﺩﻴ ﻥﺃ ﻥﻜﻤﻴ ﺎﻤﻜ ﺔﻴﺌﺎﻨﺜ ﻭﺃ ﺔﻴﺩﺎﺤﺃ ﻥﻭﻜﺘ ﺩﻗ ﻝ
ﻜﺃ ﺏﻜﺭﻤ ﺜ
ﺘﺴﻤ ﻥﻤ ﺭ ﺩﺒ
ﻱﺭﻜﺴ ل .
ﻭ ﺘ ﻁﺒﺘﺭ ﻭ ﺩﺤ ﺴﻝﺍ ﺓ ﺭﻜ ﺒ ﺫ ﺓﺭ ﺃ ﺴﻜ ﻴﺠ ﻥ ﻉﻭﻨ ﻥﻤ ﻱﺃ ﺓﺭﺸﺎﺒﻤ )
O-heterosidique
( ﺘ ﺎﻤﺇ ﻥﻭﻜ ﻊﻀﻭﻤﻝﺍ ﻲﻓ 7
ﻭﻓﻼﻔﻠﻝ ﻨ ﺍ ﻲﻓ ﻭﺃ ﺕﺎ ﻊﻀﻭﻤﻝ
ﻭﻓﻼﻔﻠﻝ 3 ﻨ ﺭﻜﺴﻝﺍ ﺕﻴﺒﺜﺘ ﻡﺘﻴ ﻭ ﺕﻻﻭ ﺩﻭﺠﻭ ﻲﻓ
ﻡﻴﺯﻨﺇ
"
O -glucosyl
transférase
"
ﺢﻨﺎﻤ ﻭ ﻝ
لﺜﻤ ﺭﻜﺴﻠ :
"
UDP-glu ) "
Uridine diphosphate glucose (
12]
ﻭ [
ﻝﺍ ﻜﺸ ل ﻝﺍ ﺎﺘ ﻲﻝ ﻙﻝﺫ ﺢﻀﻭﻴ
.
O
O OH HO
OH
OH OH
O
O OH HO
OH
O OH
Glu
UDP glu UDP
3-O-glucosyl transferase
quercétine 3-O-glucosylquercétine
ﻭ ﺘ ﺩﻗ ﺭ ﺭﺫ ﻯﺩﺤﺈﺒ ﺭﻜﺴﻝﺍ ﺓﺩﺤﻭ ﻁﺒﺘ ﺍ
ﻘﻠﺤﻝﺍ ﻥﻭﺒﺭﻜ ﺕ ﺔ
ﻉﻭﻨ ﻥﻤ ﻱﺃ ﻱﺩﻴﻨﻭﻓﻼﻔﻝﺍ لﻜﻴﻬﻠﻝ ﺔﻴﺭﻁﻌﻝﺍ
) C-hétérosidique (
ﻭ لﻜﺸﺘﺘ ﺍ ﺍ ﻩﺫﻫ ﻲﻓ ﺔﻁﺒﺍﺭﻝ ﻝﺎﺤﻝ
ﺒ ﺔ ﻴ ﻥ ﺫ ﺓﺭ ﺍ ﻜﻝ ﻥﻭﺒﺭ ﻷﺍ ﻨ ﻭ ﻱﺭﻴﻤ C1 ﺀﻱﺯﺠﻝ
ﺍﻝ ﻥﻴﻌﻀﻭﻤﻝﺍ ﺩﺤﺃ ﻭ ﺭﻜﺴ C6
ﻭﺃ C8 ﻜﻴﻠﺠﻸﻝ ﻭ
،ﻥ ﻉﻭﻨ ﻥﻤ ﺔﻁﺒﺍﺭ ﺄﺸﻨﺘ ﻭ ﻜ
ﻥﻭﺒﺭ – ﻥﻭﺒﺭﻜ , ﺩﻌﺒ ﻡﺘﺘ ﻭ
ﻝﺎﺸﻝﺍ ﻥﻴﻭﻜﺘ ﻭﻜ
ﺸﺎﺒﻤ ﻥ ﺓﺭ 11] [ ﻭ ، ﻤ ﺎﺜ ل ﻠﻋ ﻰ ﻝﺫ ﺏﻜﺭﻤﻝﺍ ﻙ
vitexine
.
19
O
O OH HO
Glu OH
vitexine
ﺭﺜﻜﻷﺍ ﻊﻗﺍﻭﻤ ﺢﻀﻭﺘ ﺔﻴﻝﺎﺘﻝﺍ ﺓﺭﻭﺼﻝﺍﻭ ﺇ
لﻴﺴﻜﻭﺭﺩﻴﻬﻝﺍ ﺕﺎﻋﻭﻤﺠﻤ ﻁﺎﺒﺘﺭ )
ﺊﻠﺘﻤﻤ ﻡﻬﺴ (
ﻱﺩﻴﻨﻭﻓﻼﻔﻝﺍ لﻜﻴﻬﻝﺎﺒ ,
ﻉﻭﻨ ﻥﻤ ﺭﻜﺴﻝﺍ ﺕﺎﻋﻭﻤﺠﻤ ﻙﻝﺫﻜﻭ
O- glycosylation
ﻭ / ﻭﺃ
C- glycosylation
) ﻊﻁﻘﺘﻤﻝﺍ ﻡﻬﺴ (
10] [ .
-V
ﺕﺍﺩﻴﻨﻭﻓﻼﻔﻝﺍ ﻡﺎﺴﻗﺃ :
ﺔﻘﻠﺤﻝﺍ ﺩﺴﻜﺄﺘ ﺔﺠﺭﺩ ﻰﻠﻋ ﺍﺩﺎﻤﺘﻋﺍ ﺎﻬﻤﻴﺴﻘﺘ ﻥﻜﻤﻴ ,C
ﺔﻘﻠﺤﻝﺍ ﻁﺎﺒﺘﺭﺍ ﺔﻬﺠ ﺏﺴﺤ ﻰﻠﻋﻭ ﺔﻘﻠﺤﻝﺎﺒ C
.A
ﻊﻴﻁﺘﺴﻨ ﺎﻤﻜ ﺎﻬﻤﻴﺴﻘﺘ
ﺎﻬﻝ ﻱﻭﻴﺤﻝﺍ ﻉﺎﻨﻁﺼﻹﺍ ﻥﻤ ﺎﻗﻼﻁﻨﺇ ,
ﻲﻓ ﺔﻴﺌﺎﻬﻨ ﺕﺎﺒﻜﺭﻤﻭ ﻁﺌﺎﺴﻭ ﺭﺒﺘﻌﻴ ﺎﻬﻀﻌﺒﻓ
ﻱﻭﻴﺤﻝﺍ ﻉﺎﻨﻁﺼﻹﺍ ﺕﺎﻨﻭﻜﻝﺎﺸﻝﺍ لﺜﻤ
, ﻝﺍ ﻭﻨﺎﻓﻼﻔ 3-
- لﻭﺃ , ﻥﺎﻓﻼﻓ 3,4-
- لﻭﻴﺩ . ﻁﻘﻓ ﻑﺭﻌﺘ ﺭﺨﻵﺍ ﺎﻬﻀﻌﺒ
ﻱﻭﻴﺤﻝﺍ ﻉﺎﻨﻁﺼﻹﺍ ﻲﻓ ﺔﻴﺌﺎﻬﻨﻝﺍ ﺕﺎﺒﻜﺭﻤﻝﺎﺒ ﻜ
ﺕﺎﻨﻭﻨﺎﻓﻼﻔﻝﺎ ,
ﺕﻻﻭﻨﻭﻓﻼﻔﻝﺍ 6]
[ .
ﻭ ﻲﻠﻴﺎﻤﻴﻓ ﺎﻬﺼﻴﺨﻠﺘ ﻥﻜﻤﻴ :
20
ﻥﻭﻓﻼﻔﻝﺍ :
ﺔﻘﻠﺤﻠﻝ ﻥﻜﻤﻴ ﻊﻀﻭﻤﻝﺍ ﻲﻓ ﺩﺠﺍﻭﺘﺘ ﻥﺃ B
ﺔﻁﺒﺍﺭﻝﺍ ﺕﻨﺎﻜ ﺍﺫﺇﻭ ،2 ـ2
ﻭ ﺔﻌﺒﺸﻤ ﺭﻴﻏ 3 لﺩﺒﺘﺴﺍ
ﻊﻗﻭﻤﻝﺍ ﻭﺒﺭﻜ ﺔﻋﻭﻤﺠﻤﺒ 4
ﻨ
،لﻴ
،ﻥﻭﻓﻼﻓ ﺫﺌﻨﻴﺤ ﺏﻜﺭﻤﻝﺍ ﻰﻤﺴ ﻲﻓ ﺔﻠﻴﺩﺒ ﺕﺎﻋﻭﺠﻤ ﺕﺎﺒﻜﺭﻤﻝﺍ ﻩﺫﻫ ﻥﻤﻀﺘﺘﻭ
ﺏﻝﺎﻐﻝﺍ ﻲﻫ ﺭﻜﺴ ﺔﺌﻴﻫ ﻰﻠﻋ ﺔﻴﺭﻜﺴ ﺕﺍﺩﺤﻭ ﻰﻠﻋ ﺎﻫﺅﺎﻨﺒ ﻱﻭﺤﻴ ﺩﻗﻭ لﻴﺴﻜﻭﺘﻴﻤ ﻭﺃ لﻴﺴﻜﻭﺭﺩﻴﻫ ﺔﻋﻭﻤﺠﻤ
،ﺭﺜﻜﺃ ﻭﺃ ﻲﺌﺎﻨﺜ ﻭﺃ ﻱﺩﺎﺤﺃ ﻝﺍ ﺔﻋﻭﻤﺠﻤﻝ ﺔﻨﻭﻜﻤﻝﺍ ﻥﻴﺠﺴﻜﺃ ﺓﺭﺫﺒ ﺕﺍﺩﺤﻭﻝﺍ ﻩﺫﻫ ﻁﺒﺘﺭﺘ ﺩﻗﻭ
ﻭﺃ لﻴﺴﻜﻭﺭﺩﻴﻬ
ﺩﺠﻨ ﺕﺎﻴﺭﻜﺴﻝﺍ ﻩﺫﻫﺭﻬﺸﺃ ﻥﻤ ﻭ ﻱﺩﻴﻨﻭﻓﻼﻔﻝﺍ لﻜﻴﻬﻠﻝ ﻥﻭﺒﺭﻜﻝﺍ ﺕﺍﺭﺫ ﻯﺩﺤﺈﺒ ﺓﺭﺸﺎﺒﻤ ﻁﺒﺘﺭﺘ :
ﺕﺍﺯﻭﺴﻜﻬﻝﺍ
Hexoses )
D-glucose ،
D-galactose ﻭﺃ
D-allose (
L-arabinose ،
L-rhamnose ،
D-
xylose. D-apioses (
.
O O
flavone
R2
R1
1
H CH3
Genkwanine
CH3 H
َ
Acacétine
H H
Apigénine
CH3 CH3
7,4'diméthoxyapigénine
O R1O
1 OH O
OR2
21
ﻥﻭﻨﺎﻓﻼﻔﻝﺍ :
ﺍﺫﺇ ﺔﻁﺒﺍﺭﻝﺍ ﺕﻨﺎﻜ C2
- C3
ﻥﻭﻨﺎﻓﻼﻓ ﺏﻜﺭﻤﻝﺍ ﻰﻤﺴﻴ ﺔﻌﺒﺸﻤ ﻥﻭﻓﻼﻔﻝﺍ لﻜﻴﻫ ﻲﻓ .
O
O
Squelette Flavonone
Naringenine (R=H) Eriodictyole (R=OH)
لﻭﻨﻭﻓﻼﻔﻝﺍ :
لﻴﺴﻜﻭﺭﺩﻴﻫ ﺔﻋﻭﻤﺠﻤ ﺕﺩﺠﻭ ﺍﺫﺇ ﺔﻝﺩﺒﺘﺴﻤ ﻭﺃ ﺓﺭﺤ (OH)
ﻊﻗﻭﻤﻝﺍ ﻲﻓ (OR) 3)
( ﺏﻜﺭﻤﻝ
ﻝﺍ ﺕﺎﺒﻜﺭﻤﻝﺍ ﻥﻤ ﺩﻴﺩﻌﻠﻝ ﺔﻴﺴﺎﺴﺃ ﺓﺍﻭﻨ لﹼﻜﺸﻴ ﻭﻫﻭ لﻭﻨﻭﻓﻼﻔﻝﺎﺒ ﺏﻜﺭﻤﻝﺍ ﻲﻤﺴ ﻥﻭﻓﻼﻔﻝﺍ ﺔﻴﺩﻴﻨﻭﻓﻼﻔ
.
O O
OR1 R2O
R3
OR4
OH
O
Squelette Flavonole
OH O
O O
R
OR
OH OH
22
OH
O
CHA LCON E DIHYDROCHA LCON E
OH
O
R4
R3
R2
R1
H OH H
H Quercétine
H OH
H Gluc
Quercétine -3-glycoside
H H
H H
Kaempferole
ﻥﻴﺩﻴﻨﻴﺴﻭﻁﻨﺍ :
ﻊﻗﻭﻤﻝﺍ ﻲﻓ ﺔﻴﻨﻭﺘﻴﺴﻝﺍ ﺔﻔﻴﻀﻭﻝﺍ ﺏﺎﻴﻐﺒ ﺕﺎﺒﻜﺭﻤﻝﺍ ﻩﺩﻫﺯﻴﻤﺘﺘ .4
ﻲـﻓ ﺔـﻴﺌﺎﻨﺜ ﺔﻁﺒﺍﺭ ﺩﻭﺠﻭ ﻭ
ﻊﻗﻭﻤﻝﺍ O1-C2
ﻊﻗﻭﻤﻝﺍ ﻲﻓ ﻙﻝﺫﻜ ﻭ C3-C4
. ﺡﻼﻤﺃ لﻜﺸ ﻰﻠﻋ ﺩﺠﺍﻭﺘﺘﻭ .
ﻝﺎﺸﻝﺍ ﻥﻭــــــﻜ :
ﺔﻘﻠﺤﻝﺍ ﺏﺎﻴﻏ ﻱﺃ ﺔﺤﻭﺘﻔﻤ ﻥﻭﻜﺘ ﻭ ﺕﺍﺩﻴﻭﻨﻭﻓﻼﻔﻠﻝ ﺔﻠﻴﺎﺨﻤ ﻥﻭﻜﺘ ﺕﺎﺒﻜﺭﻤ ﻲﻫ C
ﺔﻁﺒﺍﺭﻝﺍ ﺎﻬﻴﻓ ﻥﻭﻜﺘ ﻥﺃ ﻥﻜﻤﻴ ﺎﻤﻜ C3-C2
ﺔﻌﺒﺸﻤ ﺕﺎﻨﻭﻜﻝﺎﺸﻭﺭﺩﻴﻬﻝﺍ ﻲﺌﺎﻨﺘ ﻲﻁﻌﺘﻝ .
O
+
