O

H3C

CH3

CH3

O
OH
HO

H
N
O

O
O

H3CO

OCH3

apiol

Terpen(a)
Senyawa alam, strukturnya disusun oleh satuan isopren
Isopren dari asetat melalui mevalonat yang mengandung 5
atom karbon dg dua ikatan rangkap

Struktur kimia terpen

Isoprene

Head
Tail

Isoprene
Head
Tail

Head
Tail

Isoprene
Head
Tail

Klasifikasi Terpen
Class Name
Monoterpene
Sesquiterpene
Diterpene
Triterpene
Tetraterpene

Isoprene Units

Carbon Number

2
3
4
6
8

10
15
20
30
40

Contoh Monoterpen *)20

CH 2OH

Myrcene

O
Menthone

Geraniol

-Terpinene

Cineole

Carvone

Thujone

OH
Menthol

Tipe monoterpen
menthan, carane, bornan, pinan, fenchan

Monoterpen
Champor : ketone dari Cinamomum
camphora
Destilasi uap kulit batang &
akar
Sintesis dari pinene
Sineol : minyak cengkeh
dg destilasi uap
destilasi fraksinasi minyak
Cengkeh
Stimulan, ekspektoran

Contoh Sesquiterpen
OH

CH 2 OH
Farnesol

Bulgarene

Eudesmol
O

Atractylone

Caryophyllene

Aromadendrene

OH
Germacrone

Linderene

Seskuiterpen
Seskuiterpen terdistribusi dalam bunga,
khususnya Compositae (Asteraceae)
Efek farmakologis seskuiterpene: dari
neurotoxic sampai antimikrobia.
Struktur kimia seskuiterpene sangat
komplek, dibentuk dari kondensasi 3
isopren diikuti oksidasi.

Tipe seskuiterpen lakton

Representative
Diterpenes
CH 2 OH
P hytol

COOH
Kaurene

P imeric acid
HO

O
Marrubin

COOH
Abietic acid

Forskolin:
hipertensi& glaukoma

Ginko biloba

sintesis

Gingkolide B may be effective:

preventive treatment in reducing migraine attack frequency
Anti-inflammatory effect
Therapeutic actions on acute pancreatitis
Protective effects on ischemia-reperfusion
Protective effects on neuronal degeneration
Anti-asthmatic effects
Anti-tumor effects

Taxol

Taxol is a terpenoid
"the best anti-cancer agent by National Cancer
Institute
Has remarkable activity against advanced ovarian
and breast cancer, and has been approved for
clinical use.
25

How does taxol work as an anticancer drug?

Microtubule and tubulin
Important for cell division and intracellular
trafficking.
Polymers of tubulin
The dynamics of assembly and disassembly of
microtubules is essential for the function of
microtubules.
26

How does taxol work as an anticancer drug?

Taxol binds to assembled microtubules and
block them from disassembling, therefore
preventing normal cell division and intracellular
trafficking.
Cancer cells are active in cell division, therefore
especially vulnerable for taxol treatment.

27

Where does taxol come from?

Taxol is found in the bark of the tree.

Problems:
Pacific yew tree is very slow-growing.
Harvesting taxol from the bark kills the tree
To treat one cancer patient requires 60
pounds of Yew tree bark, the equivalent of
three, one hundred years old trees

What can we do?

Taxus brevifolia Nutt.

Pacific Yew

28

Representative
Triterpenes

CH 2 OH
HO

HO

HO

Tetraterpenen
=karotenoid= *)

8,49,50

Vitamin A

Beta carotene

 Carotenes are tetraterpenes (C40 terpenes)

Tetraterpenes can be viewed as two diterpenes (C 20 terpenes) that
are joined in a tail-to-tail fashion in the middle

The carotenes are biosynthetic precursors to Vitamin A

Carotenes are converted to vitamin A by enzymes in the liver

Chapter 23

31

Isoprene Units in
Terpenes
O

Limonene

Camphor

-Pinene

OH
-Selinene

Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

Pinene

OH
Selinene

Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

Pinene

OH
Selinene

Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

Pinene

OH
Selinene

Guaiol

Isoprene Units in Terpenes

O

Limonene

Camphor

Pinene

OH
Selinene

Guaiol

Non-Isoprenoid Terpenes
O

Valerane
-Vetivone

Eremophilone

Stop m.a. *))

terpenoid