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Lecture 2

The document discusses the biosynthesis of terpenes from isoprene units, detailing the different ways isoprene molecules can be linked, such as head-to-tail and tail-to-tail. It classifies terpenes based on the number of carbon atoms and provides examples of various types, including hemiterpenes, monoterpenes, sesquiterpenes, and triterpenes. Additionally, it highlights that all steroids are triterpenes but have undergone rearrangements that prevent them from being analyzed into isoprene units.

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12 views11 pages

Lecture 2

The document discusses the biosynthesis of terpenes from isoprene units, detailing the different ways isoprene molecules can be linked, such as head-to-tail and tail-to-tail. It classifies terpenes based on the number of carbon atoms and provides examples of various types, including hemiterpenes, monoterpenes, sesquiterpenes, and triterpenes. Additionally, it highlights that all steroids are triterpenes but have undergone rearrangements that prevent them from being analyzed into isoprene units.

Uploaded by

shamiipepo232
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Natural Products Chemistry

Dr. Mohamed Saleh Abdelfattah


Professor of Natural Products Chemistry

2024
TERPENES
And Isoprene Rule
- Formally, in biosynthesis of terpenes, two or more isoprene

molecules are linked to one another.

- Linking between two isoprene molecules could occur in three

ways, given that the head and the tail of the molecule are

primarily involved in the linking:


JOINING ISOPRENE UNITS
individual
isoprene units
Head-to-Tail join head-to-tail
an extra
bond

Tail-to-Tail

The terms head-to-tail and


tail-to-tail are often used to
describe how the isoprene
larger terpenoid units are joined.
units dimerize
tail-to-tail
….. explained later
4
TERPENES CAN BE SHOWN TO BE
FORMED FROM ISOPRENE UNITS

head to
tail

limonene diagram showing how two


isoprene units combine to
from lemon and form the limonene skeleton
orange peels

5
CLASSIFICATION OF TERPENES

TYPE OF NUMBER OF ISOPRENE


TERPENE CARBON ATOMS UNITS

hemiterpene C5 one
Monoterpene C10 two
sesquiterpene C15 three
diterpene C20 four
sesterterpene C25 five
triterpene C30 six
tetraterpene C40 eight

NOTE: hemi = half di = two


sesqui = one and a half tri = three
tetra = four
6
SOME TERPENES (C10)

C H 2O H

OH

geraniol menthol
rose and other flowers peppermint

camphor a-pinene
camphor tree turpentine
7
SESQUITERPENES
CH3

CH3 CH3
CH

CH3
guaiazulene
geranium oil

CH3

CH3 CH3

caryophyllene
oil of cloves
8
TRITERPENES

CH3

CH3 CH3
OH

CH3
C H3
TAIL-TO-TAIL
CH3 CH3

ambrein
ambergis

9
STEROIDS ARE TRITERPENES (C30)

CH3

C H3

CH3

C H3

HO
CH3 CH3

rearrangements
All steroids are triterpenes in this area
but their skeletons have been
rearranged so that they can
not be analyzed into isoprene
units.
10
TETRATERPENE
head-to-tail tail-to-tail

head-to-tail

b-carotene

Carotene is the substance in carrots that colors them orange and is the most common form of
carotene in plants.
11

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