terpenoid
DESCRIPTION
FarmakognosiTRANSCRIPT
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