terpenoid

excellent in Quality, Competitiveness, and Care (e-QCC)

excellent in Quality, Competitiveness, and Care (e-QCC)

NN

NN

O

O

H3C

CH3

CH3

HO

O

HN

O

H3CO

O

O

OCH3

apiol

O

OH

Terpen(a)

Senyawa alam, strukturnya disusun oleh satuan isopren

Isopren dari asetat melalui mevalonat yang mengandung 5 atom karbon dg dua ikatan rangkap

Isoprene

Struktur kimia terpen

Head

Tail

Head

Tail

Isoprene

Head

Tail

Head

Tail

Isoprene

Klasifikasi Terpen

Class Name Isoprene Units Carbon Number

Monoterpene 2 10

Sesquiterpene 3 15

Diterpene 4 20

Triterpene 6 30

Tetraterpene 8 40

Contoh Monoterpen *)20

CH2 OHO

O OH

O O

Myrcene Geraniol -Terpinene Cineole

Menthone Menthol Carvone Thujone

Tipe monoterpenmenthan, carane, bornan, pinan, fenchan

Monoterpen• Champor : ketone dari Cinamomum

camphoraDestilasi uap kulit batang &

akarSintesis dari pinene

• Sineol : minyak cengkehdg destilasi uapdestilasi fraksinasi minyak

CengkehStimulan, ekspektoran

Contoh Sesquiterpen

CH2OH OH

O

O O

OH

Farnesol Eudesmol Bulgarene

Atractylone Caryophyllene Aromadendrene

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

CH2OH

COOH COOH

O

OHO

O

Phytol

Pimeric acid Kaurene Abietic acid

Marrubin

Forskolin: hipertensi& glaukoma

Ginko biloba

excellent in Quality, Competitiveness, and Care (e-QCC)

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

sintesis

25

• 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.

Taxol

26

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.

27

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.

28Taxus brevifolia Nutt.Pacific Yew

Where does taxol come from?

What can we do?

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

Representative Triterpenes

HO HO HO

CH2OH

Tetraterpenen=karotenoid= *)8,49,50

• Vitamin A

• Beta carotene

Chapter 23 31

• Carotenes are tetraterpenes (C40 terpenes)

– Tetraterpenes can be viewed as two diterpenes (C20 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

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Isoprene Units in Terpenes

O

OH

Limonene Camphor -Pinene

-Selinene Guaiol

Non-Isoprenoid Terpenes

O

Valerane

-VetivoneEremophilone

Stop m.a. *))

terpenoid