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Terpenes - Alkaloids - Pheromones - Antibiotics

Here are the isoprene units for the example terpenes provided: - Limonene contains 2 isoprene units (monoterpene) - Camphor contains 2 isoprene units (monoterpene) - α-Pinene contains 2 isoprene units (monoterpene) - β-Selinene contains 3 isoprene units (sesquiterpene) - Guaiol contains 3 isoprene units (sesquiterpene)

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69 views25 pages

Terpenes - Alkaloids - Pheromones - Antibiotics

Here are the isoprene units for the example terpenes provided: - Limonene contains 2 isoprene units (monoterpene) - Camphor contains 2 isoprene units (monoterpene) - α-Pinene contains 2 isoprene units (monoterpene) - β-Selinene contains 3 isoprene units (sesquiterpene) - Guaiol contains 3 isoprene units (sesquiterpene)

Uploaded by

RedaGaafar
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 PPT, PDF, TXT or read online on Scribd
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• Terpenes

• Alkaloids
• Pheromones
• Antibiotics
• When we discuss the terpenes we are most
interested in the carbon skeleton.
Isoprene
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
CH2 OH
O

Myrcene Geraniol -Terpinene Cineole

O O

O OH

Menthone Menthol Carvone Thujone


Sesquiterpene Examples

CH 2 OH OH

Farnesol Eudesmol Bulgarene

Atractylone Caryophyllene Aromadendrene


O O

OH
Germacrone Linderene
Representative Diterpenes
CH 2 OH

Phytol

COOH COOH
Pimeric acid Kaurene Abietic acid

HO O

O
O Marrubin
Representative Triterpenes

CH 2 OH

HO HO HO
Isoprene Units in Terpenes

Limonene Camphor -Pinene

OH

 -Selinene Guaiol
Isoprene Units in Terpenes

Limonene Camphor -Pinene

OH

-Selinene Guaiol
Isoprene Units in Terpenes

Limonene Camphor -Pinene

OH

-Selinene Guaiol
Isoprene Units in Terpenes

Limonene Camphor -Pinene

OH

-Selinene Guaiol
Isoprene Units in Terpenes

Limonene Camphor -Pinene

OH

-Selinene Guaiol
Non-Isoprenoid Terpenes

Valerane Eremophilone
β-Vetivone
Alkaloids
Nitrogen containing, basic natural products
often have powerful biological activity
alkaloids are not as conveniently organized
by some common structural component.
Me

Piperidine N

H
N
Pyrrolizidine

Pyrrolidine H

Tropane

Indole

Quinoline

N
NH

Isoquinoline
HO
Examples of alkaloids

Coniine

N
Me

AcO

NH
2 HO

Morphine
HO
N

Slaframine

N MeO

Quinine

Strychnine
O

Me

H COOMe

MeOOC

COOMe

N
HO
MeO

H
Antiobiotics
There are many classes of antibiotics; four are listed
as major groups: lactams ( includes the penicillins);
tetracyclines (tetracycline); macrolides (erythromycin)
and peptides (gramacidin).
For the purposes of this course, we will be primarily
concerned with macrolide antibiotics
and highly-oxygenated compounds.
Practice Problem #1

• For each of the example terpenes given to


you, find the isoprene units that are contained
in the carbon skeleta.

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