TERPENOID

Indah Yulia Ningsih, S.Farm., M.Farm., Apt.

History
 Old term : isoprenoids
 Terpenes or terpenoids  the turpentine
oils used in elucidating the chemical
structures of isoprenoids in the 1800s
 The term isoprenoids more descriptive
than terpenoid  revealed from the latest
biochemical pathway
Pie chart representing the major groups of
plant secondary metabolites according to Croteau et
al.(2000).

(Zwenger & Basu, 2008)

Examples …

Kunyit putih
(Curcuma zedoaria)
Classification :
Plant Isoprenoids :
 Primary metabolites
 Secondary metabolites
1. Primary metabolites
 Essential for membrane integrity,
photoprotection, orchestration of
developmental programs, and
anchoring essential biochemical
functions to specific membrane
systems, respectively.
Ex : sterols, carotenoids, growth
regulators, and the polyprenol
substituents of dolichols, quinones,
and proteins.
2. Secondary metabolites
 Not essential for viability.
 However, they mediate important
interactions between plants and their
environment : plant-plant, plant-insect &
plant-pathogen interactions.
Ex : monoterpenes, sesquiterpenes, and
diterpenes.
Unit isopren
Structures of terpenoids

(Wagner & Elmadfa, 2003)

Bagan hubungan biosintesis metabolit
primer dan metabolit sekunder
 Biosintesis Terpenoid
Biosintesis Isopentenil difosfat (IPP)

(McGarvey & Croteau, 1995)

Biosintesis Terpenoid Abbreviations:
IPP: isopentenyl
diphosphate/pyro
phosphate;
DMAPP: 3,3-
dimethylallyl
diphosphate/pyro
phosphate;
GPP: geranyl
diphosphate;
FPP: farnesyl
diphosphate;
GGPP:
geranylgeranyl
diphosphate;
HMG-COA : 3-
hydroxy-
3-methylglutaryl
coenzyme A;
HMGR: HMG-
COA reductase;
(McGarvey & Croteau, 1995) .
 Terpenoid
biosynthesis
(McGarvey & Croteau, 1995)
(Chappell, 1995)
Distribusi Terpenoid
(Chappell, 1995)
(Bohlmann et al., 1998)
Ekstraksi Terpenoid
 Destilasi uap  pemisahan monoterpena
& seskuiterpena dari minyak atsiri
 Ekstraksi dengan pelarut : eter, eter
minyak bumi (PE) & kloroform
 Ekstraksi bertingkat (pe↑ polaritas solven)
 Partisi cair-cair dari ekstrak awal aseton
atau metanol
 KLT preparatif + KG
 KG preparatif + KLT
Analisis Terpenoid
 KG atau KG-SM (GC-MS)
 KCKT atau KCKT-SM (LC-MS)
 Spektofotometer IM (IR)
 KLT (TLC).
KG
 Analisiskualitatif & kuantitatif
 Kuantitatif  umum u/ kemotaksonomi
 Kolom :
 Non Polar : Apiezon L & Silikon SE 30
 Polar : poliester dietilena glikol adipat &
Carbowax 400
 Suhu : isotermik & gradien
 KLT
 Metode terpilih u/ terpena yg kurang atsiri
 Fase diam :
 Silika gel  umum.
 Silika gel-AgNO3  Σ ikatan rangkap terpena
Lempeng diaktifkan dulu, kecuali u/ analisis
terpena yg mgd atom O
 Eluen :
 Benzena atau Benzena-kloroform (1:1)
 Benzena-etil asetat (19:1)
 Metilen klorida-klorofom-etil asetat-n-propanol
(45:45:4,5:4,5)  Σ ikatan rangkap terpena
 KLT
 Deteksi umum :
 Lar. KMnO4 0,2 % dalam air
 Antimon klorida dalam kloroform
 H2SO4 atau vanilin-H2SO4
Lempeng dipanaskan pada 100-105oC 
ad warna sempurna
 Pereaksi selektif :
 Ikatan rangkap : uap brom
 Gugus keton : 2,4-dinitro fenil hidrazin (DNP)
Thank You