3. 天然物由来の医薬品 3.1. 医薬品として利用されている天然物

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
(
(
p. 3-1�
L-Tyr
(
Cf.
N
(isoquinoline)
NH
(tetrahydroisoquinoline)
N
(quinoline)
p. 3-1�
CH3
O
H N
N
O
H
H3CO
H
OCH3
OCH3
CH3
H
O
RO
O
OH
O
H H
H3CO
N
OCH3
H3CO
OCH3
R=H
R = CH3
LOCH3
O
N
(
Papaver somniferum
CH3
O
p. 3-2�
L-
(
CH3
N H
O
O
HO
H3CO
O
OCH3
O
H
HO
N
H3C
N
H3CO
OCH3
CH3
)
p. 3-2�
+
H3CO
NHCOCH3
H
H3CO
H3CO
O
-
OCH3
コルヒチン
L-
L-
(
)
N
p. 3-2�
CHO
N
H
NH2
OGlc
+
MeOOC
L-
N
H H
O
MeOOC
NH
OGlc
O
p. 3-3�
OH
H
H
H
H
N
OH
CH3
N
H H
CH3
H3CO
H3CO
H
N
N
HH
H
ajmaline
H
H O
H
OCH3
O
H
O H OCH3
OCH3
OCH3
reserpine
Rauwolfia serpentina
p. 3-3�
HO
CH3
N
H
N
H
O
H3CO H3CO
CH3
N
H
O
N
R
H OH
ビンクリスチン: R = CHO
ビンブラスチン: R = CH3
Catharanthus roseus
Vinca rosea
HO
O
CH3
OCH3
p. 3-3�
COOH
NH2
+
OPP
N
H
H
H
H
D-(+)-
HO
O H3C O
N
Me
N
H
L-Trp
N H
N
H
N
NH2
N
H
DMAPP
HOOC
COOH
O
O
N
H
N
H
O
H
N
CH3
H
HN
H
CH3
OH
CH3
HN
エルゴタミン
Claviceps purprea
エルゴメトリン
p. 3-3�
N
H
CHO
N
H
N
H
N
H
OH
H+
N
N
NH2
CHO
O
N
H
O
H
H
N
O
NADPH
NADPH
N
N
N
N
H3CO
H
HO
N
H
H3CO
N
H
HO
H
N
p. 3-4�
(-)H3C
H3C N
N
N CH3
H
H
OH
N CH3
O
*
H O
H
(-)-ヒヨスチアミン
H
OH
N CH3
O
H
H
O
O
N CH3
H O
OCH3
H
O
H O
H
H
コカイン
スコポラミン
* ラセミ体：アトロピン
p. 3-4�
O
O
N
HN
O
HO
OH
O
HO
O
O
H3C
O
H
N
N
D-ribose
N
CH3
N
O
O
O
H
N
HN
N
H
OH
7-methylxanthosine
D-ribose
O
N
N
H
OH
OH
xanthosine
N
HN
N
N
H
CH3
N
HN
N
O
7-
N
H
O
CH3
N
HN
O
N
CH3
O
CH3
N
H3C
N
O
CH3
N
N
N
CH3
N
p. 3-4�
O
O
COOH
O
O
SCoA HOOC
L-Phe
CO2
-CoA
H
OH
H
H
N
H
O
OH
NH2
NH2
CH3
H
CH3
(-)-
(-)-
(-)-
N
CH3
CH3
O
O
L-His, L-Leu
N
CH3
H H
CH3
3.1.2.
MEP
C5
GPP
C10
FPP
C15
GGPP
C30
C20
p. 3-6�
C15
O
H3C
O
H
O
H
H
O
CH3
O O
O
CH3
O
サントニン
駆虫
アルテミシニン
マラリア治療
C20
p. 3-6�
A
H3C
OH
CH3
CH3
CH3
OH
OH
CH3
プラウノトール
レチノール
ビタミンA
O
H3C
p. 3-7�
O
O CH3
OH
H3C H
O
H
H O
CH3
H
N
O
CH3
H
O
H OH
H
HO H
CH3
O O
O
O
タキソール
（パクリタキセル）
p. 3-7�
H3C
H3C
H3C
CH3
H
CH3
H
H
H
HO
cholest-5-en-3β-ol
-5-3β21
12
H
19
H
H
11
1
2
H
A
3
4
H
5
α
18
C
9
10
5
24
22
27
25
23
17
13
14
8 H
B
20
D
26
16
15
7
H
6
B/C
β
p. 3-8�
O
H
AcO
O O
O
O
Ac2O
H
H
AcO
AcOH
H
HO
H
O
CrO3
H
H
O
Δ
H
AcOH
H
AcO
H2
O
OH
HO
O
O
H
H
O
O
[O]
H
H
H
H
H
O
OH–
H
H
HO
OH
OH
H
H
O
H
H
H
HO
H
p. 3-9�
O
O
OH
H3C
H3C
H
CH3
CH3
H
H
H
HO
O
H
H
O O H
H
O O
H
H
O
H
H
H
H
H
H
CH3
O
O
H3C
OH
H
CH3
H
CH3
OH
H
OH
H
H
H
H
O O H
R2O
OH
O
H
O
H
O O
H
H
H
H
H
H
CH3
H
CH3
OH
H
H
OH
OH
OR1
C
R1
17
α,β3β14βA/B, C/D
H
R2
OH
cis
H
3-
COCH3
H
H
CH2OH
O
H
OH H
HO
H
H
H
OH
CH2OH
O
H
OH H
HO
H
H
OH
p. 3-9�
3.1.3.
(
C6-C3
2 x C6-C3
C6-C3
OCH3
O
O
O
p. 3-9�
3.1.4.
H
N
CO2H
CO2H
H
H2C
H3C
CO2H
H
H
H
HO
OH
L-DOPA
L-
Digenea simplex
NH2

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