Chemistry of Natural Products
• 1. Terpenoids
• 2. Flavonoids
Terpenes/Terpenoids
Ø S.V.Bhat, B.A. Nagasmpagi and M.Sivakumar. Chemistry of Natural Products.
Narosa Publications 2009
Ø I.L.Finar
Ø O.P.Agarwal
Topics
• Introduction
• Classification and Nomenclature
• Occurance
• Isolation and General methods for
identifications
• Biosynthesis
• Synthesis of Geraniol, Menthol, β-
carotene
Terpenes
• Turpentine (also called spirit of turpentine, oil of
turpentine, and wood turpentine) is a fluid
obtained by the distillation of resin obtained
from trees, mainly pine
turpentine tree (Pistacia terebinthus),
Also emits by some termites
General Rules
• When we discuss the terpenes we are most
interested in the carbon skeleton.
• Isoprene Rule- All terpenoids are build of
isoprene units Wallach (1887)
• Special isoprene Rule- Terpenoids are built up
of isoprene unit and joined by head to tail
union Ingold (1925)
TERPENES
The Czech chemist Leopold Ruzicka ( born 1887) showed that
many compounds found in nature were formed from multiples
of five carbons arranged in the same pattern as an isoprene
molecule (obtained by pyrolysis of natural rubber).
natural
rubber head
Δ C tail .
C
C C C C
C C
C C
isoprene isoprene
unit
He called these compounds “terpenes”. 6
JOINING ISOPRENE UNITS
.
C
The terms head-to-tail and C C Head-to-Tail
tail-to-tail are often used to
describe how the isoprene C C
units are joined.
an extra
Tail-to-Tail bond
Head-to-Tail
7
TERPENES CAN BE SHOWN TO BE
FORMED FROM ISOPRENE UNITS
7
1
6 2
head to
tail
5 3
4
10 9 8
limonene diagram showing how two
from lemon and isoprene units combine to
orange peels form the limonene skeleton
8
Isoprene
2-methyl-1,3-butadiene
Head
Tail Isoprene
Head
Tail
Head
Tail Isoprene
Head
Tail
Terpene Classification
•
• Class Name Isoprene Units
Carbon Number
Terpene Classification
•
• Class Name Isoprene Units
Carbon Number
•
• Monoterpene 2
10
•
Terpene Classification
•
• Class Name Isoprene Units
Carbon Number
•
• Monoterpene 2
10
• Sesquiterpene 3
15
•
Terpene Classification
•
• Class Name Isoprene Units
Carbon Number
•
• Monoterpene 2
10
• Sesquiterpene 3
15
• Diterpene 4
20
•
Terpene Classification
•
• Class Name Isoprene Units
Carbon Number
•
• Monoterpene 2
10
• Sesquiterpene 3
15
• Diterpene 4
20
• Triterpene 6
30
Monoterpene Examples
CH 2OH
O
Myrcene! Geraniol α -Terpinene Cineole!
O O
O OH
Menthone Menthol Carvone Thujone
Sesquiterpene
Examples
CH 2 OH OH
Farnesol Eude smol Bulga re ne
Atractylone Caryophylle ne Aromade ndre ne
O O
OH
Ge rmac rone Linderene
Representative
Diterpenes
CH 2 OH
Phytol
COOH COOH
Pime ric a cid Ka urene Abietic acid
HO O
O
O Marrubin
Representative
Triterpenes
CH 2 OH
HO HO HO
Isoprene Units in
Terpenes
O
Limonene Camphor α -Pinene
OH
β -Selinene Guaiol
Isoprene Units in Terpenes
Limonene Camphor α -Pinene
OH
β -Selinene Guaiol
Isoprene Units in Terpenes
Limonene Camphor α -Pinene
OH
β -Selinene Guaiol
Isoprene Units in Terpenes
Limonene Camphor α -Pinene
OH
β -Selinene Guaiol
Isoprene Units in Terpenes
Limonene Camphor α -Pinene
OH
β -Selinene Guaiol
