Fitokimia TM 3

FITOKIMIA TM 3
BIOSINTESIS/BIOGENESIS
Ada 3 jalur biosintesis yang umum dikenal
yaitu :
1. THE ACETATE PATHWAY: FATTY ACIDS

AND POLYKETIDES
2. THE SHIKIMATE PATHWAY: AROMATIC
AMINO ACIDS AND PHENYLPROPANOIDS
3. THE MEVALONATE AND DEOXYXYLULO-
SE PHOSPHATE PATHWAYS: TERPENO-
IDS AND STEROIDS
1. THE ACETATE PATHWAY: FATTY
ACIDS AND POLYKETIDES
CH3 CH3
C O + HSCoA C O + H2O
OH SCoA
POLIKETIDA
Asam asetat (Asetil CoA, Malonil CoA)
sumber atom C
Metabolit sekunder pada fungi dan bakteri
Contoh :- asam orselinat, fungi dan linchen
- endokrosin, pigmen antrakuinon
lichenCebtralia endocrocea dan
fungus Claviceps purpurea
- griseofulvin, Penicillium griseo-
fulvin
- kulvularin, Culvularis sp
POLIKETIDA
CH3
O
COOH COOH
4 X C2
O O
HO OH
ASAM ORSELINAT
HO CH3
O
8 X C2 O O O
COOH COOH
O O O OH O OH
ENDOKROSIN
POLIKETIDA
O OCH3
O O O OCH3
7 X C2 O
COOH O O
O
H3CO O
Cl CH3
GRISEOFULVIN
O O O CH3
O OH
C
HO
O O
8 X C2 O
O O O OH O
KULVULARIN
CH3 COOH CH3 COOH C2
KONDENSASI
(+C2)
CH3 CO CH2 COOH CH3 CO CH2 COOH C2
REDUKSI
CH3 CH2 CH2 COOH
KONDENSASI
(+C2)
CH3 (CH2)2 CO CH2 COOH CH3 (CH2)2 CO CH2 COOH C2
REDUKSI
CH3 (CH2)2 CH2 CH2 COOH
KONDENSASI
(+C2)
CH3 (CH2)4 CO CH2 COOH CH3 (CH2)4 CO CH2 COOH C2
ASAM LEMAK POLIKETIDA Cn
Biosintesis asam lemak dan poliketida

(a )
(a ) Kondensasi tipe KROTONAT
R - CO - CH2 - CO - CH2 - CO - CH2 - COOH (b) Kondensasi tipe CLAISEN
(b) R = CH3 - (CO - CH2) n
(a ) (b) R n = 0, 1, 2 . . . . .
R CO
COOH O O
O O
R
R CO
COOH HO OH
HO OH
OH
Asam 2,4-dihidroksi-6-metil benzoat Asilfloroglusinol
(turunan resorsinol = asam-asam orselinat R = CH3 asetilfloroglusinol
Endokrosin Kurvularin
(polisiklik) (monosiklik)
Kondensasi tipe krotonat (aldol)
CH3 CH3
COOH COOH COOH
O
4 X C2
O O
O O HO OH
ASAM ORSELINAT
HO CH3
O
8 X C2 O O O OH
COOH C
O O O OH O OH O
(O)
O O
HO CH3 HO CH3
OH
C
OH O OH OH O OH O
EMODIN ENDOKROSIN
Kondensasi tipe Claisen
O O
O O O OH
C
H3C C CH2
H2 H3C H3C
OH
O C C
O O HO OH
C O
H2
ASETIL FLOROGLUSINOL
O O O O
H2 H2 H2
H3C C C C C C C C 0H TETRA - ASETIL
O OH
O O
HO
H3C OH O H3C O O
- PIRON
(c )
(c ) Reaksi LAKTONISASI
R - CO - CH2 - CO - CH2 - CO - CH2 - COOH (d) Reaksi ETERIFIKASI
(d) R = CH3 - (CO - CH2) n
(c ) (d) n = 0, 1, 2 . . . . .
OH O
R O O R O CH2 - COOH
piron piron
O O OOH O
R C
O
(a ) O (c ) O (b ) (b )
CHOOH
C O O R O O O R
O HOOH (d ) (d )
OH O
HO R
O
HO O R
OH O
ISOKUMARIN KHROMON
Kondensasi tipe laktonisasi
O O O O
H2 H2 H2
H 3C C C C C C C C 0H TETRA - ASETIL
O OH
O O
HO
H 3C OH O H 3C O O
- PIRON
O O O O
H2 H2 H2
Kondensasi tipe eterifikasi
H3C C C C C C C C 0H TETRA - ASETIL
O O
O O
HO
H3C OH CH3 HO O CH3
- PIRON
2. THE SHIKIMATE PATHWAY : AROMATIK AMINO
ACID AND PHENYL PROPANOIDS
O PO3H2
COOH COOH COOH
H2C C H
COOH - H2O CH2
H CH2
C C
HO OH HO O COOH O COOH
OH OH OH
ASAM SHIKIMAT ASAM KORISMAT
COOH COOH COOH

O
O
NH2 O
HO C CH2 C COOH
- NH3 - H2O
- CO2
OH
ASAM SINAMAT FENIL ALANIN ASAM FENILPIRUVAT ASAM PREFENAT
COOH COOH
NH2
O PO3H2
COOH COOH COOH
H2C C H
COOH - H2O CH2
H CH2
C C
HO OH HO O COOH O COOH
OH OH OH
ASAM SHIKIMAT ASAM KORISMAT
COOH COOH COOH

O
O
NH2 O
HO C CH2 C COOH
- NH3 - H2O
- CO2
OH
ASAM SINAMAT FENIL ALANIN ASAM FENILPIRUVAT ASAM PREFENAT
COOH COOH
NH2
ASAM p-LKUMARAT TIROSIN
OH OH
MMAMA
3. THE MEVALONATE AND DEOXYXYLULOSE PHOS-
PHATE PATHWAYS : TERPENOIDS AND STEROIDS
TERIMA
KASIH

Fitokimia TM 3

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FITOKIMIA TM 3

1. THE ACETATE PATHWAY: FATTY ACIDS

CH3 CO CH2 COOH CH3 CO CH2 COOH C2

CH3 CH2 CH2 COOH

CH3 (CH2)2 CO CH2 COOH CH3 (CH2)2 CO CH2 COOH C2

CH3 (CH2)2 CH2 CH2 COOH

ASAM LEMAK POLIKETIDA Cn

Biosintesis asam lemak dan poliketida

(b) R = CH3 - (CO - CH2) n

(turunan resorsinol = asam-asam orselinat R = CH3 asetilfloroglusinol

(d) R = CH3 - (CO - CH2) n

COOH COOH COOH

COOH COOH COOH

ASAM p-LKUMARAT TIROSIN

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