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3.
3.1. ) (3-29〜3-34
3.2. ) ( +
3-35, 3-36
3.1. ) (
3.1.1.
3.1.2.
3.1.3.3.1.4.
3.1.5.3.1.6.
3.1.1.
L-Tyr (
L-Trp (
L-Trp C5 DMAPP
) (
L-Orn (
L-Tyr (
NH
����������(tetrahydroisoquinoline)
N
���(quinoline)
Cf.
N
�����(isoquinoline)
p. 3-1�
O OHRO
NCH3
H
H
H H
����R = H�����R = CH3
N
O
O
O
OCH3
OCH3O
H3CO
CH3HH
H3CO
H3CO
N
OCH3
OCH3
���� ��� �
L- (
N CH3OCH3
O
O
��������
Papaver somniferum
p. 3-1�
N
H3CO O
CH3
HO
HO OCH3
NH3C CH3
O
H
H H3CON
OCH3
OO
������
�����
L- (
)
p. 3-2�
H3COH3CO
H3CO
H
NHCOCH3
OOCH3
コルヒチン
L- L- (
)
-
+
N
��������� �
p. 3-2�
NH
NH2
O
OGlc
CHO
MeOOC
NH
NH
O
OGlc
MeOOC
H+
����������� �
� � �� � �
L-�������������
����������
p. 3-2�
N
N
CH3
H
OHH
H OH
CH3H
HH H
H
ajmaline
NH
N
OCH3OCH3
H3CO H
O
OOCH3
OCH3
H
HH3CO
O HH
H
reserpine
Rauwolfia serpentina
p. 3-3�
ビンクリスチン: R = CHOビンブラスチン: R = CH3
NH
N
NH3COOH
H
HOCH3
R
N
O
CH3
H
HH3CO
OH
CH3
O
OCH3
O
Catharanthus roseus Vinca rosea
p. 3-3�
L-Trp
NH
NH2
COOH
OPP
+
NH
NH2
COOH
NH
HOOCNH
D-(+)-�����
Me
DMAPP
HN
N
NN
O
CH3
O
NH O
H
HO
O
H3C
H
H
H
HN
N
OHCH3
CH3
O
NH
H
H
H
エルゴタミン エルゴメトリン
Claviceps purprea
p. 3-3�
NH
N
H
OHH+
NH
N
CHO
H
NH2
NCHO
HO NH
O
N
N N
NHO
N� ����������
NADPH
NH
HO
N
NH
HO
N
H3COH3CO
NADPH
� �� ������
������
������
HH
p. 3-3�
N CH3
H
H
H
O
OH
ON CH3
H
H
H
O
OH
O
H
H
O N CH3
H
H
H
H
O
OCH3
O
O
(-)-ヒヨスチアミン スコポラミンラセミ体：アトロピン*
*
コカイン
NH3C
NH3CN CH3
������
(-)-
p. 3-4�
xanthosine 7-methylxanthosine
D-ribose �����
HN
NH
N
N
O
O
CH3
HN
N N
N
O
O
CH3
�����
CH3
N
N N
N
O
O
CH3
CH3
H3CHN
NH
N
HN
O
O
N
N N
HN
O
OCH3
H3C
�������
�����7-����������
�����
D-ribose �����
HN
NH
N
N
O
O
OHOH
HOO
CH3
HN
NH
N
N
O
O
OHOH
HOO
p. 3-4�
L-Phe� CO2
COOHSCoA
O
HOOC
O
O
O
� �����
NH2
O
CH3
���� ����-CoA
(-)-���(-)-������
NH2
OHH
H CH3
(-)-�����
CH3
HN
OHH
H CH3
N
N OO
CH3HHCH3
������
L-His, L-Leu
p. 3-4�
3.1.2.
GPP C10
FPP C15
GGPP C20
C30
MEP
C5
C15
H3C
CH3
OO
O
H
H
HCH3
O
O
O
OO
サントニン駆虫 アルテミシニン
マラリア治療
p. 3-6�
C20
A
OH
OH
CH3
CH3
CH3H3C CH3
OH
OO
OH
O
NH
O
CH3CH3
HO OHO
CH3 OHOOH3C
O
H
H
H
H
HH
CH3
O
H3CO
プラウノトール
タキソール（パクリタキセル）
レチノール�ビタミンA�
p. 3-7�
p. 3-6�
H3C
H
H
H3C CH3
CH3
H
H3C H
HO������
cholest-5-en-3β-ol�����-5-�-3β-���
5 α β
B/C
1
2
3
4
5
6
7
8
9
10
11
12
1314
15
16
17
18
19
2021 22
23
24
25
26
27
A B
C D
H
H
H
H
H H
H
p. 3-7�
HOH
H
H
H O
O
Ac2O
AcOH
AcOH
H
H
HO
AcO
CrO3 HO
AcOO O
OH–
HOH
H
H
O
H2
Δ
AcOH
O
O
[O]
OH
H
H
O
OH
H
H
OH
OH
H
H
OOH
HO
HOH
H
H
OH
p. 3-8�
H
H3C
O
H
H
OH
HH3C
OO
HH O
O HOH
H
CH3
HH O
O HOH
H
CH3
HH O
HO HOH
H
CH3
H
H
H3C
OH
H
OH
HCH3
O O
H
OHH
R1
R2
H
H
HCOCH3
H O
O HOH
H
CH3
HH O
O HOH
H
CH3
HH O
R2O HOR1
H
CH3
H
H O
HO HH
OH
CH2OH
HH
OH
H O
HO HH
OH
CH2OH
HH
OH
����� ���� ��� C �����
-
17 α,β-3β- 14β- OH 3-A/B, C/D cis
p. 3-9�
3.1.3.
OOOOCH3
��������
������
������� ��������
(
C6-C3
2 x C6-C3
C6-C3
p. 3-9�
3.1.4.
HN
HCO2H
HHH2C
H3C
CO2H
CO2H
H NH2HOOH
���� ����
Digenea simplex
L-DOPA L-
p. 3-9�
