TERPENOID
-
Upload
ahmad-riduan -
Category
Documents
-
view
19 -
download
3
description
Transcript of TERPENOID
![Page 1: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/1.jpg)
excellent in Quality, Competitiveness, and Care (e-QCC)
![Page 2: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/2.jpg)
![Page 3: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/3.jpg)
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
![Page 4: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/4.jpg)
![Page 5: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/5.jpg)
Terpen(a)
Senyawa alam, strukturnya disusun oleh satuan isopren
Isopren dari asetat melalui mevalonat yang mengandung 5 atom karbon dg dua ikatan rangkap
![Page 6: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/6.jpg)
Isoprene
Struktur kimia terpen
![Page 7: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/7.jpg)
Head
Tail
Head
Tail
Isoprene
![Page 8: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/8.jpg)
Head
Tail
Head
Tail
Isoprene
![Page 9: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/9.jpg)
Klasifikasi Terpen
Class Name Isoprene Units Carbon Number
Monoterpene 2 10
Sesquiterpene 3 15
Diterpene 4 20
Triterpene 6 30
Tetraterpene 8 40
![Page 10: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/10.jpg)
Contoh Monoterpen *)20
CH2 OHO
O OH
O O
Myrcene Geraniol -Terpinene Cineole
Menthone Menthol Carvone Thujone
![Page 11: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/11.jpg)
Tipe monoterpenmenthan, carane, bornan, pinan, fenchan
![Page 12: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/12.jpg)
Monoterpen• Champor : ketone dari Cinamomum
camphoraDestilasi uap kulit batang &
akarSintesis dari pinene
• Sineol : minyak cengkehdg destilasi uapdestilasi fraksinasi minyak
CengkehStimulan, ekspektoran
![Page 13: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/13.jpg)
Contoh Sesquiterpen
CH2OH OH
O
O O
OH
Farnesol Eudesmol Bulgarene
Atractylone Caryophyllene Aromadendrene
Germacrone Linderene
![Page 14: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/14.jpg)
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.
![Page 15: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/15.jpg)
Tipe seskuiterpen lakton
![Page 16: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/16.jpg)
![Page 17: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/17.jpg)
![Page 18: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/18.jpg)
![Page 19: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/19.jpg)
![Page 20: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/20.jpg)
![Page 21: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/21.jpg)
Representative Diterpenes
CH2OH
COOH COOH
O
OHO
O
Phytol
Pimeric acid Kaurene Abietic acid
Marrubin
![Page 22: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/22.jpg)
Forskolin: hipertensi& glaukoma
![Page 23: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/23.jpg)
Ginko biloba
![Page 24: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/24.jpg)
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
![Page 25: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/25.jpg)
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
![Page 26: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/26.jpg)
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.
![Page 27: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/27.jpg)
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.
![Page 28: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/28.jpg)
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
![Page 29: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/29.jpg)
Representative Triterpenes
HO HO HO
CH2OH
![Page 30: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/30.jpg)
Tetraterpenen=karotenoid= *)8,49,50
• Vitamin A
• Beta carotene
![Page 31: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/31.jpg)
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
![Page 32: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/32.jpg)
![Page 33: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/33.jpg)
Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
![Page 34: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/34.jpg)
Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
![Page 35: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/35.jpg)
Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
![Page 36: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/36.jpg)
Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
![Page 37: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/37.jpg)
Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
![Page 38: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/38.jpg)
Non-Isoprenoid Terpenes
O
Valerane
-VetivoneEremophilone
![Page 39: TERPENOID](https://reader035.fdocument.pub/reader035/viewer/2022062216/55cf917e550346f57b8deea3/html5/thumbnails/39.jpg)
Stop m.a. *))
terpenoid