GOLONGAN TERPENOID

Soerya Dewi M
Kimia Bahan Alam Hayati
 Chlorophyll + CO2 + light

photosynthesis
METABOLIT PRIMER & SEKUNDER

carbohydrates

glycolisis
Pentose cycle

Phosphoenolpyruvic acid

Shikimic acid Pyruvic acid

alkaloid

Aromatic amino acids Acetyl coenzime A

Amino acids

Cinnamic acids Citric acid/cycle acid

 METABOLIT PRIMER & SEKUNDER (lanjutan)

Acetyl coenzyme A
Cinnamic acids

Flavonoid compound Malonyl co-A

Phenylpropanoid compound Fatty acids

polyacetylenes
polyketides
Mevalonic acid

Phenolic compound
Terpenoid compound
Steroid
Carotenoid
Building blocks
 Terpenes

• Terpenes
are largest class of secondary metabolite,
some are volatile and insoluble in water,
biosynthesize from acetyle-Co A or glycolytic
intermediate.
• Terpenoids
are terpene like substances or derivatives of
terpenes or modified terpenes.
 Terpenes

• Natural organic compounds.

• Components of a variety of fruit and floral
flavors and aromas.
• Used in perfumes, essential oils and
medicines.
• Unsaturated compounds formed by joining
together isoprene units.
 Nomenclature
• All terpenes are formed by union of five carbon
elements that is iso-pentane

• All basic structure of terpenes are called isoprene

units, because terpenes can decompose on high
temperature to give isoprenes.

• These five carbon units polymerize to give rise to large

number of terpenes.
 Classification of Terpenes
Type of terpene Number of carbon atom Isoprene unit
Hemiterpene C5 one
Monoterpene C10 two
Sesquiterpene C15 three
Diterpene C20 four
Sesterterpene C25 five
Triterpene C30 six
Tetraterpene C40 eight
Polyterpene C>40 > eight
Example of Terpenes
 Biosynthesis of Terpenes

Terpenes are biosynthesized from primary

metabolites at least in two different ways:
1. Mavalonic Acid Pathway
2. Methylerythritole Phopsphate (MEP)
Pathway
MEVALONIC ACID PATHWAY
Methylerythritole phopsphate(MEP) pathway
Methylerythritole phopsphate(MEP) pathway (cont.)
 SCH 511

CYTOSOL CHLOROPLASTS
Acetyl CoA G3P + Pyruvate

Mevalonic Acid MethylErythritol Phosphate

(MEP)

Sesquiterpenes
Hemiterpenes,
Triterpenes,
monoterpenes, diterpenes,
Steroid
and tetraterpenes
 SCH 511

Head

OPP DMAPP .
C

SN1 C C
Head

C C
Tail
.
C

Head C C

OPP
C C
Tail
Head Tail

OPP

16
Dr. Solomon Derese
 SCH 511
Reaction of IPP and DMAPP

OPP
- OPP

OPP

OPP

H H

OPP

17
Dr. Solomon Derese
 SCH 511

Joining Isoprene Units

Head-to-Tail

Tail-to-Tail Tail to Middle

Larger terpenoid units dimerize tail-to-tail.

 Biosintesis Terpenoid

Aharoni et al.,2005, Trends in Plant Science, vol. 10(12), 594-602)

Song et al., 2014, Nat. Prod. Rep,
Monoterpenes
Monoterpenes
Monoterpenes
Monoterpenes
Monoterpenes
Irregular Monoterpenes
Iridoids
Iridoids
Sesquiterpenes
Sesquiterpenes
Sesquiterpenes
Biosintesis sesquiterpen

Awouafack et al.,2013,
Biosintesis Sesquiterpenes (lanjutan)
Biosintesis Sesquiterpenes (lanjutan)
Biosintesis Sesquiterpenes (lanjutan)
Biosintesis Sesquiterpenes (lanjutan)
 Sesquiterpenes (lanjutan)
Biosintesis Sesquiterpenes
 Sesquiterpenes (lanjutan)
Biosintesis Sesquiterpenes
Diterpenes
Diterpenes
Diterpenes
Diterpenes
Diterpenes
Diterpenes
Diterpenes
Sesterterpenes
Triterpenes
Triterpenes
Triterpenes
Triterpenes
Steroid
Steroid
Steroid
Steroid
Steroid
Steroid
Steroid