Analysemetoder anvendt på antocyaner

(1)

(2)

(3)

! "

# # " #

#

! $

% &

' (

)

*

)+,,,-

.

(4)

/( ((

/ "$ (0

// (1

/2 '$ (3

/0 "$ 4 (3

/1 "$ #

2( 5 (

2 %

2( )

2 6 % /

2/ 7%*88,89:89,-

. /

22 !%)+,,, 0

20 "% 1

21 &% ;

2; )#% *)<8,. 3

2/ + /(

2/( + = /

2/ '!>'$!$ >$ $$ /

2// )- //

2/2 ? )-

,)+@, //

2/0 ? )-

,)!, //

2/1 ? )- ) ,A+B /2

2/; ? )- ) &A,+B /2

2/3 ? )- ) 'A5+B /2

2/C ? )- ) >A5+B /0

2/( ? )-

,)+@,-&A,+B /0

22 + /0

22( 7 /0

0( 5 % /3

0 < $ /3

0/ > " D"?-; /3

02 5% # /C

(5)

# /C

01 ")<8, /C

0; )+,,, /C

03 )+,,, /C

0C )+,,, $ 2

0( '!> $-/- 2

0((

$ 2

0( 6&8,- 7)E 2(

0(/ ) $ 2(

0(2 7 $ 2(

0(0 =-$ 2(

0(1 $ 2

0(; 7 -

2

0(3 2/

0(C ? $ # 2/

0 )+,,,- $ 2/

0( 22

1( A 20

1 )+,,,- 20

1/ '!>-$-/- 2C

1/(

,- 2C

1/ )- 0

1// )+@,- - 0(

1/2 )!,- - 0/

1/0 >A5+B- 02

1/1 &A,+B- 00

1/; )+@,- - 01

1/3 +'!>- 0;

12

$ 03

10 ) $ 1

11 7 $ 1

1; - $ 1(

13 $ 1

1C 7 -

$ 1/

1C( 10

1C = )<8, 10

1C/ 5F 11

(6)

1(( ;

1( ;2

!

;( A% ;0

;(( + ;0

;( ;1

;(/ 8 ;3

; A ;3

;( =:+ ;3

; *'!>. ;C

(7)

? % 4-

? (

+

*. $ -

#

4$

"$ -

%

% :

G( H

$

F 5

4

- G H G/HG2H =

F 4

A

*$. &

# )

-G0H )

$ I

J"$K$ $

$*$-

. $$K

J

? $-

$ ?

%#:#

% *)+,,,:,,,. *&8,.

#% *)<8,.

=: *'!>.

" $

* . #

D"?-; ) + ,-, ,-

*)+,,,.

(8)

#$

+

*$-/-. '!>

5 )+,,, -

$ -

# * . # * .

?

*%$

. =

5

< #* . -

>

$

? )+,,, -

$ ? -

%)+,,,

? # --

::$: ?

$

"

,-/-* .-

% -

! -

%

- !

7 F

!1I2

?

=

"

D"?-;

(9)

O ⁺

O

OH OH OH O

H O

H

OH

OH OH

O ⁺

O

OH OH OH O

O O H

OH OH

O H

OH

OH OH

O ⁺

O

O OH OH O

H O

H

OH

OH OH

O

OH OH

O H

Cyanidin-3-glukosid

Cyanidin-3-sambubiosid

Cyanidin-3-rutinosid Pigmentene omtalt i oppgaven:

7(I? $ I $-/- $-

/- $-/-

(10)

O ⁺

O

O OH OH O

H O

H

OH

OH OH

OH

O

OH OH

O H O ⁺

O

OH OH OH O

H O

H

OH

OH OH

OH

Delfinidin-3-glukosid

Delfinidin-3-rutinosid

7I? % I%-/- %-/-

(11)

!

# 4-

G1H ?

G; H

%

G3H 7 %

*. *..I

: *#.

" I> # '

I

=

0(0-020

I + -

I

/0-/31

I 4 I

//-/0

I7% -

I6!:),L

#$" I7 -

I

/;-2(

%& I 7

4I

*. -

,- * % /. -

( + *4 4 $$.

):

/ " * $.

2 6 * .

7 4 (0,-

,1-,/-,1-%

(12)

O O

H

OH O

OH

A C

B

7/I+ 4

OH

O OH O

H

OH

72I+ $$

O

OH

OH O O

H

70I+

O

O OH O

H

OH

71I+ 4

,/- *,-. * $-

$%2.*%0. -

,- )4 -

- 4 *% 1.

/- 7

(13)

O

O OH O

H

OH

7;I+ 4

O

O OH O

H

OH

73I+ 4

O ⁺

O

OH

OH OH

OH O

H

CH ₃

7CI+4 )I

,- 7 4 *%;. -

4*%3. ,-

< *%C. $ -A) -A!

7 4

A- ?

4

! ,-A-,

?

(14)

+

7 ;- 4 4

4 4

4 /-;- $ /- 0-

G; H ? 4

M

O O

H

OH OH OH

O O

H O H

OH OH

O

O H

OH OH OH O O

H

OH OH OH OH

O O

H O H

OH OH OH

Glukose Galaktose Rhamnose

Xylose Arabinose

7(I? 4

7 - -

7

*-A--?---?-. --

*-A--8---?-.

-

+#,-,-

*4-,-. 7(C3(-

,- 1-3- 4 GCH

4-A-4

-NG; H

(15)

O ⁺

R1

OH

R2 OH

OH O

H ²

3 5 4 6

7 8

9

10 1 '

2 '

4 '

3 '

5 '

6 '

A C

B

7((I5 $ -

"$ 4 ? -

%

% G(H ' J$J

JJ ? 4

$#G(( H ?

? %#

7 # #

$ % $

-

G( H

& (I? $ *+% ((

> >

.

* /-$.

< ) ) 0 01 A

, A) ) 0/0 0/ >

< A,)

) 0/; 00 A:

?% A) A) 021 0/2 :%

< A,)

A) 023 0/1 7

! A,)

A,)

00 0/3 7

< $ $

7 $-

# $

$4*1.

$ * . ? $

(16)

# )

G(/HG(2H.

6 $ $

4*/(. 8%-

# $4

4

! 4 I

( ?-*,1-,/-,1.

+ 4

/ !% 4 * -

.

' ( )*

&

# -

)

*

,.

% G(0H

"- 4 J--J

$-,"-," ?,1-,/-

-- !

,(0- $$

+ % (

' &

7$$4-

7( $$ $

' + , &

=% 4-

4-

- * -

4. ! % 4

* 4-A-.

4*4-,-.$-

(17)

SCoA COOH

O O SCoA

OH ₂ CO ₂

OH O

O H

OH

O O

O SCoA

O

OH

O OH O H

OH

O H

OH

O OH O H

O

O OH O H

H OH H

OH

O ⁺

OH O H

OH OH

+

-3

-2 p- Kumarsyre

Hypotetisk i ntermedi at

Chalcon Flavanon

Dihydroflavanol

Antocyanidin

7 (I$

(18)

"$4-%-

)(- = )-

- :

+% (/

5 4 4

%

& I7

-

+ $

+

=

7 + $

+

=-

* .

" F

$

?

"$ G(1 H "-

$-

$-/-F-

G(;H ?4

? $

$ F ) 20 * )

$. # ? 4

%

" $ #

% ?

4 $ G( H

5 $ -

* .

$F-

?-

(19)

O ⁺

OH OH

OR OH

O H

O

OH OH

OR OH

O O

OH O

OR OH

O H

O

OR OH

O

OH OH

O

OH O

OR OH

O

OH OH

OR OH

O H

OH

O

OH OH

OR OH

O H

OH

OH OH

OR OH

O

H OH

O

OR

OH O

H OH

O

OH OH

7(/I5 $-

(20)

G(; H

< F

G((HG(3 H $ #-

$# -

F 5 F$

) " -

>-

7 -

) /

) 7 $

$ "-

$ $

? $ -

+#

$ -

G(CH

! $

7

$

G(CH

(21)

5

=#:#

&8,

,,-

)<8,

)

&8,

,,,%

)<8,

'!>

7(2I 7 $

- %

! "

7

5

! # # F

+ 4

-

4

5%

&

# =

(22)

3-/ ,

+

#

%

F

?% %4

! %I

6%

=#% #

.. /

? !$+$&K*(3;-(C(C.-

%%

(C( -

I

J %

J

( I

J %

(C(J

*$ O % O.

& &K

7

&K

!

F

5 &K

- %

GH

5%

< (C/;

(C2; , < "

,I

(23)

%$$$&KJ

$ $ J

.. 0 ,

+% -

% %

*#:# .%*"D"?-;.-

% * . #% *-

. % * .

)+,,, ?,,,

8+, +5, ,,,

,, 88,

<, 68, 6+,

&8, 8, )<8, 6,

%

7(0I6 %

.. ,122#3 24 524 #$*

$'

7 F

# ?

(24)

& *

$.

=

J J ?

? F 7 -

# F

A (

F I

*(.

?

( ( #

F A

4 ?

5 4

5 #:#

$ 4 -

?,,,*? ,, ,-

.G(H ,<, *,< , . GH )+,,,

*)+ , , , . 22

- & $

5 4

: 0:0 ,

F* -

.

* .4* . ?

-

=

* .

- " "

=:4

F % -

$4 +-

F $-

F*4

(25)

%

#:# $ G/ H ?

:$ 0:0 5

: * . $

%

*$. 5 4 $-

-

! $

? -

?

F

7,,- -

8 $

$ -

A 4

*&7"

),.

? #

$ 4 <-

#

.. 6,3 /###

? -

# ) -

#

+ )+,,,

4 7

# -

<

#

5 ?"?-

7)+,,,

# * .

*(. "

+ M

/-2 )<8,

#

+ # )+,,, ) -

(26)

F =

* . #

JJ ?-

?

# JJ

&$

--:-:$ : II(I0 -

2 &7" *4 . ?

# #

30

/ ?

(

.. ),

5 $

--

+ "-

D"?-; ?

4 *20

:. +

-

?4- -

# -

-

<-

7 4

!

) ' )-

$:4

* $I 0 ( &7"

),.

(27)

&8,*&8, .##-

*$. 4

#

&8,F#%

-

& $

?

=- * 4.

*'F-

N ". 7 4

+ 4

&8, -

*.

5 F &8,-

-I

*.

7 (1I& &8,-

72#* )

&8, %-

-

(28)

$ 7)E *--. (I(I/ : G2 H #

"E *-$-.

#

- ) 72#

7 J-FJ -

# *% (1 .

< #

? -

$ ($4

*/-2 4 .

<

4 & # -

? #

&8,- 7 -

< # &8,-

=-

F %-

# =7)E(I(I/ / 2

&8,- $

.. /6 8, 1/-2#'

)<8, *) <$ 89 , .

!

+

)<8,

)-

= -

(-(0 7 )<8,

F ?

)<8,

7

?

? *<,. )<8,-

G0 H 7 (; )<8,-

7

5

F ?

(29)

>

>/

<

7

,(3-

=:=+-

+

7(;I+ )<8,-

5 ?

* 2. -

* /. 7 %

-

(30)

8 )<8, -

I

26 )

AI),AA) CI0*:.

26 9!A)I),AA)I)

A0I0I2 *:.

0 10 20 30 40 50 60 70 80 90 100

0 5 10 15 20 25 30

Minutter

% B

0 10 20 30 40 50 60 70 80 90 100

0 5 10 15 20 25 30

Minutter

% B

7 (3I I )<8,- $

'I )<8,-

7 *--.

> " *-.

?

" ?

(31)

*%(3. $

'

$ $ -

%

- ) /-2#

<

-

= 4

?"? *? " ?$. ? -

?

-

?

- G1H

%

I )K-<$ (0

<I )K-<$ ,

?I? "? *?"?.

I A?+) 0 0M/

*($ .

I(

7 -

*

(-(0. = -

4

$" "

) *.

* .

: -

=> G(2H

(32)

'!>* .

.. :+

=:

=-

!# =:

7

#

F

=- -

4 6 4 -

/-00 2-30 " $

- *3-/. +

)-

.. ;3 ; " " " ""

'!>- (C21

'!>

G;HG3H

'!>

$

+

'

*

'-+-'-+. * '-+-+-'. 4

*'-+-'-+. N

'>7- -

N- 5

F ? F -

>7- 7 -

* . ## *.

## ? -

'!>- GCH

? '!>

(33)

?

4

%

?>D-1 7&-'!>

1(/!)N ) (0C!)N

,

< DE'-'!>

? % 5

'!>- $-/- -

)+,,, '!> 7

'!>- G/ H

.. /*

" '!>- =-

+

"- C-1 %

"- 1-2

+- 2 #

# 4 -

##

.. ( /*

# /<#

)+@, *)$ + @ ,$.

)

, #

*

. = M-

, -

5 #

,A+B-

? -

.. ( /*

# /9#

)!, *)$ ! ,.

)

, 4 #

*

OO/. ?

M-

,-

(34)

)!, 4 ? -

-

=

& %

: - :

5 %I *-

.

5-%)!,- ?

?-

,-

)-

(/-(0)N 5-

%

.. ( /* / #=>

,A+B*,A+ $$ B. -

?

-

,A+B %

,A+B- -

$ !

)-( %

)- )- )-/ <

% A

4 #

,A+B

#

.. ( /* / 7=#>

&A,+B*&A,+ $$ B.

+

&A,+B

&A,+B ?

'

%

.. ( /* / ;=>

'A5+B *'$ A 5F$ + $$ B.

'A5-F 'A5-F

(35)

-

= -

# 5

..? ( /* / =>

>A5+B *> $ A 5F$ + $$ B.

#

>A5+B 'A5+B-

+'A5+B

>A5-F #

A -

..@ ( /*

# /<#*7=#>

)+@,-&A,+B

# *)+@,.

*&A,+B. +

, )-

5

$

.. AA6

5

?

7

I ) P )

P ) P &

I ) P

) P

?

*/.

(36)

! ! !

( - -

Q -

/ - Q

2 Q Q

& 2I7-

! ! !

!

( - - -

Q - -

/ - Q -

2 Q Q -

0 - - Q

1 Q - Q

; - Q Q

3 Q Q Q

? # -

? - #

5!

I

*2.

' F

" I

*0.

' -

"

)

# -

J-J JQJ ?

7

F F

F )

&0I?

F 7

-

% I

*1.

(37)

. . ! !

!

( - - - Q Q Q - >(

Q - - - - Q Q >

/ - Q - - Q - Q >/

2 Q Q - Q - - - >2

0 - - Q Q - - Q >0

1 Q - Q - Q - - >1

; - Q Q - - Q - >;

3 Q Q Q Q Q Q Q >3

#

I

*;.

F

FI

*3.

5F -

I

*C.

! -

F

(38)

? -

$ ? -

)<8,)+,,,'!> =

! # " %

0 # ( -

*),. ( ?

# (-

5

%

&

5/ ? /

$ ?$-

*( .

?

7 *$.

*6

.& $

7 5

$- # + $ -

4$ =

0 7$

'( )*+,

?

)-

5 0

# <

- '

) 1-;

? * ),.

8

(39)

0#

0( 5 % $-

D"?-;* 0/. &

! -# " .

0 # 0 # (

*),. (

? # (

5

( (

),

? %

? $

D"?-; * 0/.

/&01

+* .

( ! ( -

6

3 / /1 0 4-

, /$111

5 * (. $

0 )+,,,-

"*(. #

JJ 7

(: ( ?

0

2 /$111 ""

5 * . $

2 )+,,,-

(40)

J J 7

0: ( ?

0

3 /$111 (

"$ * -

), . ( 5

( 2

)+,,,- " )+,,,

4 5' + +

< -

$-/- <

D"?-; ?

-

'!>-

$ > ( Æ

,

<

? *,?

A?. -

$ <

/ '!>- ?

> '!>-

I )

, -?@7-,A+B&A,+B>A5+B

)+@,)!, )+@,-&A,+B

6( % " ". %+

( - # # 0

! ), < #-

4 &

C0 Æ

, 0 ( 2 3 (1

&8,

(41)

#- &8,- ($

# < 7)E *-

-. (I(I/ 5 /-2 -

$ >

/

##(0!),

0 ? C0-(

Æ

,

1 5

84*#-

.

+

' %

%

9( ". %

< - #-

&8,- +

I

5$ (I(

5:

5 :$ I/I0 -

? &8,- 4

5

6( 6;+

? % 0 $ $-/-

)-

(13: (1:32: 2: ?

=- "

(42)

%/

=-

?

*($ ($.

6( ( % +

"$$-/-%I

( = ! ), ?

- ! ), ?

-),-

/ " /! )

<A

#

2 &

&

"$ //:

)

6 C0 Æ

,1

=- &8,-

% 7 =-

-0 ?

0 ?

? =- 2 2 ;

& %

, 9 ( (

%

5- #

$ ?

(43)

? $-/-

;: ? -

/ 1! )

<A

?

1

& 1I=

+) 2 /6

& *D . C Æ

, (0 Æ

,

& *D

. 0 (

+ *D

. /!)

<A

1! )

<A

5(0 )<8,

<

)<8,

#

2 6 % (

5 " D"?-; ?

0$ %

? ) -

< -

? /-2

)1-; + *

),.

-/

3 * %

( # (0

)<8, + 0 0 /! )

<A

(0 ?

C0-(

Æ

, / 5

(0 )<8, >

4 /$111+ %

)+,,,- *30.

# J

(44)

2 7

0: ( ?

0

6( ( %

5 -

)+,,, & (

2 5

( $ * . ?

I

)--$*0I(I2.

)-$-- *0I(I0I(.

-- *II(.

)-- *1I0I(.

<-- *2I/I(.

!- *(I(.

---$- *II(I0.

>

(45)

$ % 7

)+ ,-, ,

)+,,, #

$

,-/-

<"" " %

5 $ D"?-

)<8, * 01. "

$ (22 */

. (23 *;;

. ? *

(; . # 5

7(CI)<8,- * .

/$111+ %

?

)+,,, * 0;

03.

*% .

?

0 5 -

)<8, %

)<8,-%(/

( ((0

(46)

I .

(47)

7(I)<8,- (*./*.

)+,,,

7I)<8,- / 2 (2 * .

)+,,,

(48)

(22 # " *2

3./ (22

)<8,

*%.

?

7 (

)<8, *+ %

% .

# (((/(2(-

(//(23

/ (2( #

+ (((/ +

- / (2(

(0

2 (2(

# ? (/

(2(

(2

(0; 7

2 (/ )<8,

(49)

O ⁺

O

OH OH OH O

H O

H

OH

2 3 5 4

6 7

8 9

10 1' 2'

3' 4' 5' 6'

1''

2''

3'' 5'' 4''

6''

7/I+ $-/-

40 60

80 100

120 140

160 ppm

72I

,- $-/-

..

#*

- *% 2. + -

4

(50)

* % (/.

# ?3-

1 - ?

.. /*

<- - *

10C . *+% 0.)1

*<A)-

. 5

+ -

7

20 0 %

& ;I+ )-

B A B)

3C0 +

3 ? 30 (/

;C0 ? (/

; ? 30

1C ? (C

1; ? (C

? ; ;C0 3

+; ;C0 -

30 (/ )N + 3

?-

; 3 ;C0 3

? "D- ;-3

- ;C0-3 - ?

-0J-

$ <

/J- A A,)

-

/J- * . -

$

= 1C 1;

(C)N ? #"D-

& 3C0

(51)

10 9 8 7 6 5 4 3 2 1 ppm

6.8 7.0 7.2 7.4 7.6 7.8 8.0 8.2 8.4 8.6 8.8

9.0 ppm

70I I )-'!> $-/- 'I

)- -*1; C( .

.. /<#*3 6 *

)+@,- *%1.%

!M-

-

(52)

ppm

6.5 7.0

7.5 8.0

8.5 9.0 ppm

90 95 100 105 110 115 120 125 130 135 140 145 150

71I )+@,- -

ppm

5.5 6.0

6.5 7.0

7.5 8.0

8.5 9.0 ppm

100 110 120 130 140 150 160 170

7;I )!,- -$-/-

(53)

-A )A

3C0 (/0

3 (3

;C0 (;1

; (1C

1C C2

1; (

.. /9#*3 6 *

)!,- * % ;. >A5+B -

$ )!,- -

4

5*

. 4-

*

.

2

3C0-

% *(202 (0; (0C (1/ .

+ (/0 *

.

((0 (0

?

# + )- 3C0

1C 1; ?

21 3 + -

2- %

#3C0 ?#

2 1 3 (-

?((0 = #

1 3

? (J- ?

(0

? 1-3-

3- 0- 1-

C- A

3-

1- - ?

3- 1C 1- 1; A

C-0- * (0;

(0C . 5

;-

A (J-

(54)

)- ?

J0J 1J

2- J

)- ? 1J- *3

. ? 1J -

J-0J- ?

/J2J

(210 (00

.. =>*

>A5+B- *% 3. 'A5-F 0J-

1J- J0J

? 020 3C0

/- *'A5-F 2-

(R- .

ppm

5.5 6.0

6.5 7.0

7.5 8.0

8.5 9.0 ppm

5.5

6.0

6.5

7.0

7.5

8.0

8.5

9.0

73I >A5+B- -

(55)

&A,+B- *% C. % -

!JJ-020 -

)I/1 /12

/;2 /3 /C ? #

# 1R-

' /C

- 2; ? -

1R- - -

ppm

3.5 4.0

4.5 5.0

5.5 6.0 ppm

3.2 3.4 3.6 3.8 4.0 4.2 4.4 4.6 4.8 5.0 5.2 5.4 5.6 5.8 6.0

7CI &A,+B- -

(56)

)+@,- *%/.%-

- )

2; /C I -

ppm

3.0 3.5

4.0 4.5

5.0 5.5 ppm

50 55 60 65 70 75 80 85 90 95 100 105 110 115

7/I )+@,- -

& CI

-A )A

020 (0

2; 1(1

/C 1(1

/3 ;/3

/;2 ;;C

/10 ;1

/1 ;

(57)

)- )!,-

+-

!$-/-

* (.

G/(H

& (I+ $-/-

- - . A B) . A

,

(1/

/ (202

2 3C0 (/0

0 (0C

1 1; (

; (;

3 1C C2

C (0;

( ((0

(J (0

J ;C0 (;1

/J (210

2J (00

0J ; (1C

1J 3 (3

A--6

(R 020 (0

R /3 ;/3

/R /10 ;1

2R /1 ;

0R /;2 ;;C

1"R 2; 1(1

1R /C 1(1

(58)

+ 0(( #- -

$ # # 7

&8,-

& ((I?

- . /

(

0

/ (

2

0 2

1 3

; (1

? #- &8,-

7)E *(I(I/.

?

- 5

&8,-

7/(

&8,- >

- !

G2 H %

< ( * .

< *0

./*(. <

2*. -

$ <0*2. #

$ < 1 *3

. < ;

*(1.

$

?

1! C0 Æ

,

(59)

< -

( ; < -

I (. . 0 /. (

2. 0. 2 1. 3 ;. (1 -

>

- =

G2H ?% 0

$2 00

?%-/- 1/ /- $

;0 /- /-%-

$ ;0 C

(60)

+ 0(/ $ #

# ! ), ? -

% C0-(

Æ

,1 5%

&8,- ?

#

$ ? 4

&8,- >

- 30 8 -

4

9( ". %

7* 0(2.

< $

$- ? #

- < &8,

# ?

$ 0-(

# +

%

5 -

#

<

$ #

5I/I0-

$ ?-

-

F $

&

&8,-

? -

?

$ %

-

7

(61)

=:=+- $-/-I

(31:(1:32:2: "0/

*% /.

0 1 2 3 4 5 6 7

0 0,2 0,4 0,6 0,8 1 1,2 1,4 1,6 1,8

mg/ml cyanidin-3-glukosid

A bs or ba ns v e d 5 2 0 n m

7 /I I " - $-/- 'I -

0

=#=-

(62)

#

-

? %

=:=+-

+

$ (:

2 6( ( % +

% %

$ $

//: 0 -

?

? % // /

?-0/ $-/-

020$

6 $

A %

# !

-

=-

*%//. '

?

5 -

$ ?

-:

+-

-: ?

#

- *((;

Æ

,#.

5 * ;3 Æ

,. = -

)-

( Æ

,

#

(63)

0 0,5 1 1,5 2 2,5 3 3,5 4

Vann, 2M HCl n-ButOH, 3M HCl EtOH (100%), 3M H3PO4

EtOH (96%), ionebytter

A bs or bs jo n v e d 5 4 5 n m

7//I I" - $ 'I %-

22 ;

= :#

#

3 9 ( - ( +

%

+ : #

$ ?

(64)

? $-/-

;: ? -

/ 1! )

<A

?

(

& (I=

+) 2 /6

& *D . C Æ

, (0 Æ

,

& *D

. 0 (

+ *D

. /!)

<A

1! )

<A

& (/I>

C C

C

C C

C

C C

C

-

( - - - Q Q Q - (;0C

- - Q Q - - Q ;2C

/ - Q - - Q - Q (2

2 - Q Q - - Q - 2(C

0 Q - - - - Q Q 22;

1 Q - Q - Q - - ;C

; Q Q - Q - - - 21

3 Q Q Q Q Q Q Q (1

5 (0 )<8,

(65)

O (C0

)FI

O -20

O -13;0

O ((

+ FI

O -0

O -2;;0

O -2;0

O -030

= (/ -

I ? -

F +

F*

.

= # *

.F

.?. + A/-2#

*7 /2 /0 .

(*-- -.I)

$-/-

? #

$

*-- Q.I & #

$

+# (

/*-Q-.I& #

$

8 (

2*- QQ.I 7

$

0 *Q - -.I '#

$

!

(66)

$

+#

; *Q Q -.I 7 $

!

3 *Q Q Q.I 7 $

?#

.?. D

<20#

$ ?

<2*/!)

<A

.

0 *1! )

<A

. ? (0 )<8,

=-

"*%/1/;.

0

2 =

4- *

% (/.

8 #

(67)

?% *C Æ

,.

0 (

/! 1!

(68)

?% *(0 Æ

,.

0 (

/! 1!

(69)

*. / ; *

.

(70)

*. / ; *

.

(71)

Dag 0

Dag 3

Dag 7

Parallell 4 Parallell 5 2350

2400 2450 2500 2550 2600

7 /3I + -

2 0 =

*%/1 /;.

7 /CI )<8, # I I

(72)

)<8,-#

% I$-/-$-/-%-/--

%-/-G/ H =

$ % + -

* % /C . / C0-(

Æ

,

/!)

<A

$

6( ( % +

5 )+,,,- -

? #

<

#

7 #

#

# )

/**" 1'

?

# "$

- 5#

)+,,,

/*"** 1'

<--

$ 5 )+,,,

BA** 1'

+ " -

/** 1'

+ :

?

- *) * 1'

?

< #

(73)

"

*) *) *"* 1'

? # *-$.

' $

I $

?

# JJ )+,,,

$

+ # -

$

5 #

#

(74)

& -

% -

'!> ?

$

)+,,,

( 5 * .

)+,,, ?

'!>

=)+,,,- %-

-

? -

::"$: "

?

$

/ 4

$

= -

-

D"?-; =

4

? : -

- $

(75)

, < #

..

) %

% ! -

" 7 2 -

7 2I +% F " ,

*. *. $*. *7 8#

%G1H

5 F"

, %

S # = -

F

F ! -

% I

+F

7 F L

% 7

(76)

+ &

" * . A >

%F -

I

*(.

7 > #

7 >

%

*((.

8%

* . 8

% '

?*.

*(.

*

T .

-

7 O(

# :

? *

.

'

#

?

.. 9E

F

' #

= F -

? F

(77)

+ 'I

*(/.

5 I

*(2.

' #

F 5'

?

-

#

< I

!

*(0.

< -

) #

?

)#

*(1.

)

8 F

)

5F

)

!

)

!

)

! #

8F*

.I& FF

-

?

5F*

.I)

#

! *

.I8

!#-

+

F -

(78)

#

# +F

F 'F

" >

! # *

.I +F

# ' F

#

G1H G// H

.. 2

" % F

? F

F !

6 F

, < " "

.. :+5

'%-

?

%*.

?

5 % ?

% %

% *.

7 5 5

- 5 7 #

I

"

#$

*(;.

$J *

.

$*

:.

" --

-

J

J %

(79)

# ?=: #

G/2H

.. B 1;'

" '!>

*.

= * ). O

'!> !

'!> ?

, )

, O

?

(1

## '!>-

A )-

,- -

I -

?

-

5 " "

"

I

+

?

? %

" #% *(3.

* # <$J .

" F -

6

-

" -

?F

(80)

G(H 8

(CC0

GH ," >$-5 8 <$ ' ( !$

?(CC3

G/H ) ) ) > " 7 4

$ M

$$ )$ $ *

$ /;I(2;U(1/(CC3

G2H " +N ? < = $$ I

" K + $ C1I(;U(/C

(CC1

G0H ) , - $ "$$

< 8(C1;

G1H ! >+ ? ) ?= )

. 8 (CC2

G;H > ! &$9 4%$ (C3 $

$9

G3H ) $ , -

) 88(C;/

GCH ) /01 2345 , -

) 88(C33

G(H ) / 01$ 2346 , -

) 88(CC/ + 22(-2;(

G((H 6 !NN 5 ! $7

,>, <(CC/

G(H ! " ' ( . */.I3CUC/ (C3;

G(/H ? +$ = E "$$ <

8 (C3C + /0-/0

G(2H ?) E 8 7

!$6K-) (CC0

G(0H >8 E / $ 5K " *<-

.8 (C;0

(81)

/2I((CU(/ (C/

G(;H ,! )

8 92: "> 8$'KB(C31

G(3H < , & 7$03 (CC; + (/

G(CH ! " ' . 0I(CU(C2(C3;

GH 8+ 5 , 0-1 (CC1 + /2/-/0(

G(H 6E 7$ ! " ? $-$$

$ +$ , *3/.I220U223 (C32

GH ) >V &W ! XW$-) $-

;1/(CC; + /20-/0

G/H ! " , $ ? -

, (C33

G2H ! " 6E 7$ + $

$ $ + $ ,

*/(3.I20U202 (C30

G0H ! " ) $ 9 $ $

$ K- $ ; $

1 < =3 22 "8 2335 7 >

2U2/ (CC

G1H 6 8 > ? /

(CC2

G;H ) 7 - / ( .

E-=,) (CC3

G3H ! + ) . AM-

<(CC/

GCH < ) '- EI

I::KKK$:::

G/H 'V 7 . 7

G/(H ! " ?E "E 'A< +$ -

$ $-/- (

(/$ $K- -$$-

9 I(;0U(3/ (CC(

(82)

G//H )& ) ? -

/ (CC(

G/2H E !$< 8/(CC(

Analysemetoder anvendt på antocyaner

O +

O

O

OH OH OH O

H O

H

OH

OH OH

O +

O

O

OH OH OH O

O O H

OH OH

O H

OH

OH OH

O +

O

O

O OH OH O

H O

H

OH

OH OH

O

OH OH

O H

Cyanidin-3-glukosid

Cyanidin-3-sambubiosid

Cyanidin-3-rutinosid Pigmentene omtalt i oppgaven:

O +

O

O

O OH OH O

H O

H

OH

OH OH

OH

O

OH OH

O H O +

O

O

OH OH OH O

H O

H

OH

OH OH

OH

Delfinidin-3-glukosid

Delfinidin-3-rutinosid

O O

H

OH O

OH

A C

B

OH

O OH O

H

OH

O

OH

OH O O

H

O

O OH O

H

OH

O

O OH O

H

OH

OH

O

O OH O

H

O ⁺

O ⁺

O ⁺

O ⁺

O H O ⁺

O ⁺

CH ₃

O ⁺

H ²

OH ₂ CO ₂

O ⁺