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天然物化学とは? PowerPoint PPT Presentation


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天然物化学とは?. 生薬学. 生化学. 有機化学. 分析化学. 学問は全て繋がっている。. 天然物から創薬へ・・. Key word :. lead 化合物、コンビナトリアルケミストリー、ハイスループットスクリーニング( HTS). ターゲット(標的)の探索. 疾患、生体内における標的部位の決定 天然物からの探索. in vitro (試験管内)、 in vivo (生体内)における薬物評価系を決める. スクリーニングの構築. Lead 化合物の探索. 抽出・分離・構造決定. 生理活性を有する天然由来抽出物から目的化合物を単離精製.

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天然物化学とは?

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5685064


5685064

Key word :

leadHTS)

in vitroin vivo

Lead

-


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morphine

(Serturner)

1803morphine

1818quinine

1819caffeine

1831atropine

1855cocaine

1885ephedrine

1895tubocrarine

1929peniciline

1952reserpine

1953kainic acid

1958vinbrastine

1971paclitaxel

quinine

caffeine

atropine

cocaine

ephedrine

tubocurarine

oeniciline

(Fleming)

kainic acid

reserpine

paclitaxel

vinblastine


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A. Fleming

E. Jenner

G. Domagk

B.N. Ames

P. Ehrlich

S.A. Waksman

R. Koch

J. Pasturner

F. Serturner

H.A. Krebs

Mutation test

TCA

B1


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a) B. N. Amesmutation test

b) P. Ehrlichsalvarsan

c) G. Domagkpenicillin

d) S. A. Waksmanstreptomycin

e) A. Flemingsulfa drug

82


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Taxusbaccata

Taxaceae

paclitaxel (taxol)


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paclitaxel(taxol)

retrosynthesis)

E. J. Corey1991


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paclitaxel(taxol)


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Podophyllumpeltatum

Berberidaceae

Natural products

drug

Podophyllotoxin

PodophyllotoxinGlucoside

Etoposide


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-

C2CoA

C6-C2

C5

C5


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1


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2

Ex)

Krebs/ TCA


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3

Ex)


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1

Krebs

CoA-

-

1- 5-

1- 5-


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2

1) CoA

CoA

(PG)

*

*2

2)

+

4-


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3

3)

CoA x 3

4)

+

3-

5)

Krebs

Krebs


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81

1) C1 : ONCL-S-

2) C2 : CoA

3) C5 : isoprene unit)


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82

4) C6C3

5) C6C2N

6) - C2N


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83

7) C4N

8) C5N


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84

podophylotoxin

papaverine

2 x C6C3 + 4 x C1

C6C2N + C6C2 + 4 x C1

C6C3


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CoA


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1

L-C1

SAM S

O - , N


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2

L-C1

C


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3

DMAPP = C5

O

SN1


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1


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2

A)

B)

C)

D) SAM


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3

A)

SP2

B) /

1

C)


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Wanger - Meerwein

C5

A) 1, 2

D) 1, 3

B) 1, 2

E) 1, 2

C) 1, 2


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AldolClaisen

-


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AldolClaisen

A)

B)

A + B


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Acetyl CoAMalonylCoA


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MalonylCoAAcetoacetylCoA

Claisen


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Claisen

Aldol


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C N1)

Mannich

Schiff

A) 1

B) 2

Schiff


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C N2)

Mannich

(tautomerism)

2


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C N3)

Mannich

.hemibrevetoxin B)


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(transamination) 1

1)


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(transamination) 2

2)


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(decarboxylation) 1

1

1) aldolclaisen

2)

Ex)


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(decarboxylation) 2

A)

PLP


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(decarboxylation) 3

B) b

6


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(decarboxylation) 4-1

C) a


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(decarboxylation) 4-2

C) a


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(decarboxylation) 4-3

C) a


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1

1) NADH NAD+, NADPH NADP+, FAD FADH, FMN FMNH2)

2) peroxidase etc)

3) mono oxygenase, dioxygenase etc)

4) monoamine oxidase, diamineoxidase)

5) Bayer Villiger

6)


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2

1) NADH NAD+, NADPH NADP+)2


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3

1) FAD FADH, FMN FMNH2


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4

2) oxidase


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5

3) oxygenase

(mono oxygenase)

(dioxygenase)

P450hydroxylase)

450nm


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6

3) oxygenase

(mono oxygenase)

(dioxygenase)

P450


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7

3) oxygenase

(mono oxygenase)

(dioxygenase)

P450


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8

3) oxygenase2

(mono oxygenase)

(dioxygenase)


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9

3) oxygenase

(mono oxygenase)

(dioxygenase)


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10

4) amineoxidase

(monoamine oxidase)

FAD

(diamineoxidase)


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11

5) Baeyer Villiger

NADPHP450FAD


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12

6)

P450


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b

X

X = O, N, S, C

()

A) O

B) C


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O

b-

b-

b-

b-


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1

(PG)

(


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MalonylCoAAcetoacetylCoA

2

1) NADH NAD+, NADPH NADP+)2


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2

(PG)

(

16

18

18

18

18

20

0

0

1

2

3

4


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3

(PG)

(

(PG)C20


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4

(PG)

(

(PG)3


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5

(PG)

(


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6

(PG)

(


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7

(PG)

(


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(decarboxylation) 3

B) b

6


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8

(PG)

(


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1

L-L-L-

Styrylpyrone


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Illiciumverum


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2


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3

C6 C3 L Phe, L Tyr, L Trp


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4

C6 C3


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Cinnamomi Cortex

Cinnamomum cassia

Moutan Cortex

Paeoniasuffruticosa


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CaryophylliFlos

Syzygiumaromaticum

(Clove )

(4)

()...600g

()...1

...3

...1

[A]

...10cm

...1/3

...1/2

[]

...1

...1/2

...

...

...2

...

...

...

1.

2.(A)

3.(2)(1)2003040

4.(3)

5.5mm

6.(5)(4)


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5

C6 C3


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hemiterpenes

C10

monoterpenes (C10), iridoids

IPP

C15

sesquiterpenes (C15)

X 2

IPP

C20

diterpenes (C20)

X 2

IPP

C25

sesterterpenes (C25)

C30

triterpenoids (C30)

steroids (C18 C30)

tetraterpenoids (C40), carotenoids

C40


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l menthol cholesterol


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1

-1


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2

-2


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3

-1


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(decarboxylation) 4-2

C) a


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4

-2


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5

(C10) - 1


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6

(C10) - 2


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7

(C10) 1

Ex)

Nepetacatania

- 1


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8

(C10) 2

- 2


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9

(C15) 1


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10

(C15) 2


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11

(C20) 1


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12

(C20) 3


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Taxusbaccata

Taxaceae

paclitaxel (taxol)


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13

(C20) 2 (paclitaxel)


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14

(C25)

Helminthosporiummaydisophioboleneophiobolin A


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15

(C30) 1

Squalene - 1


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16

(C30) 2

Squalene - 2


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17

(C30) 3


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18

(C30) 4


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19

(C40) 1

carotenoid1


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20

(C40) 2


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1

L-PheL-TyrL-Trp

L-OrnL-Lys


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2

1)

2)


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3

1)

2)

(-)-hyoscyamine


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4

1)

2)

cocaine


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5

1)

2)


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6

- 1


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7

- 2


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8


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9

- 4


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10

colchicine

noscapin

tubocrarine

Colchicum autumnale

Papaversomniferum

Chondodendrontomentosum

Strychnostoxifera

palmatine

Coptis japonica

Phellodendronamurense


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11

-1


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12

-2

reserpine

ergometrine

ergotamine

vincristine

vinbrastine

physostigmine


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