TERPENOID

KELOMPOK 4 :
Riski Ishariyanto
Fransiska D. Toteng
Gabriela Teurupun
Sesty Rumperiai
Raisah N.
Merianti
 Terpenoid

• Senyawa yang berasal dari

molekul satuan isoprena H 3C
(C5H8)
C CH CH 2
• Kerangka karbonnya
dibangun oleh H2 C
penyambungan 2 atau lebih isoprena
satuan C5

Penggolongan berdasarkan jumlah satuan tersebut :

dua (C10), tiga (C15), empat (C20) enam (C30) atau
delapan (C40) satuan
Golongan Utama
Terpenoid
Compounds containing carbon atoms in multiples of 5 suggest a C 5 building block - isoprene units
linked in a “head-to-tail” fashion

2-methyl-1,3-butadiene

“Head” - branched end of isoprene

“Tail” - unbranched end of isoprene

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Finding the isoprene building block - cyclic compounds

Finding the isoprene building block - sesquiterpenes (C15)

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 Finding the isoprene building block - triterpenes (C30) -

Squalene has a natural and vital part in the synthesis of all plant and animal sterols, including
cholesterol, steroid hormones, and vitamin D in the human body

Finding the isoprene building block - tetraterpenes (C40)

Lycopene's eleven conjugated double bonds give it its deep red color and are responsible for its antioxidant activity.

Lycopene is responsible for the red color in tomatoes and watermelon 6

-carotene is the compound that causes carrots and apricots to be orange

Hemiterpenes consist of a single isoprene unit. Isoprene itself is considered the only hemiterpene,
but oxygen-containing derivatives are hemiterpenoids such as prenol (found in citrus fruits, grapes, blackberry,
tomato) and isovaleric acid (found in essential oils).
Monoterpenes consist of two isoprene units and have the molecular formula C10H16. Examples of
monoterpenes are: geraniol, limonene and terpineol.
Sesquiterpenes consist of three isoprene units and have the molecular formula C15H24. Examples of
sesquiterpenes are: humulene, farnesenes, farnesol.

Prenol isovaleric acid

limonene humulene
a strong smell of oranges
found in the essential oils of Humulus lupulus terpineol
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 Contoh Monoterpen

CH 2OH
O

Myrcene Geraniol a-Terpinene Cineole

O O

O OH

Menthone Menthol Carvone Thujone

 Contoh Seskuiterpen

CH 2 OH OH

Farnesol Eudesmol Bulgarene

Atractylone Caryophyllene Aromadendrene

O O

OH
Germacrone Linderene
Bagaimana terbentuknya Terpenoid ?

 Terpen berasal dari sejumlah reaksi

ekstensif antara 2 unit C5 :
dimetilalilpirofosfat (DMPP) dan
isopentenil pirofosfat (IPP)  produk ini
akan memiliki berbagai struktur Isoprena Isopentana
berkarbon lima.

 DMPP dan IPP dibiosintesis dari 1

sumber yaitu asam mevalonat atau
deoksisilulosa fosfat.
OPP
OPP

DMPP IPP
Biosynthesis of Terpenes

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 Isopentenyl pyrophosphate is only one of the necessary reagents for the biosynthesis of terpenes…
dimethylallyl pyrophosphate, a C5 isomer, is also necessary:

RULE - isopentenyl pyrophosphate and dimethylallyl pyrophosphate are the C 5 building blocks for the
biosynthesis of terpenes

Elimination of a proton from a carbocation intermediate generates a double bond (E1 reaction)
Geranyl pyrophosphate - C10 building block for many biological monoterpenes
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Geranyl pyrophospate ester hid ile geraniol verir.
 From 10 Carbons to 15

OPP

+
OPP

Geranyl pyrophosphate IPP

+
OPP
From 10 Carbons to 15

OPP

+
– H

+
OPP
 From 10 Carbons to 15

OPP

 This compound is called farnesyl pyrophosphate.

 Hydrolysis of the pyrophosphate ester gives the alcohol farnesol.
TERIMAKASIH