Introduction to natural prodects
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Transcript of Introduction to natural prodects
![Page 1: Introduction to natural prodects](https://reader036.fdocuments.net/reader036/viewer/2022081413/54778972b4af9fde6f8b456b/html5/thumbnails/1.jpg)
• Terpenes
• Alkaloids
• Pheromones
• Antibiotics
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• When we discuss the terpenes we are most interested in the carbon skeleton.
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Isoprene
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Head
Tail
Head
Tail
Isoprene
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Head
Tail
Head
Tail
Isoprene
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Terpene Classification
•
• Class Name Isoprene Units Carbon Number
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Terpene Classification
•
• Class Name Isoprene Units Carbon Number
•
• Monoterpene 2 10
•
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Terpene Classification
•
• Class Name Isoprene Units Carbon Number
•
• Monoterpene 2 10
• Sesquiterpene 3 15
•
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Terpene Classification
•
• Class Name Isoprene Units Carbon Number
•
• Monoterpene 2 10
• Sesquiterpene 3 15
• Diterpene 4 20
•
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Terpene Classification
•
• Class Name Isoprene Units Carbon Number
•
• Monoterpene 2 10
• Sesquiterpene 3 15
• Diterpene 4 20
• Triterpene 6 30
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Monoterpene Examples
CH2 OHO
O OH
O O
Myrcene Geraniol -Terpinene Cineole
Menthone Menthol Carvone Thujone
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Sesquiterpene Examples
CH2OH OH
O
O O
OH
Farnesol Eudesmol Bulgarene
Atractylone Caryophyllene Aromadendrene
Germacrone Linderene
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Representative Diterpenes
CH2OH
COOH COOH
O
OHO
O
Phytol
Pimeric acid Kaurene Abietic acid
Marrubin
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Representative Triterpenes
HO HO HO
CH2OH
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Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
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Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
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Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
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Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
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Isoprene Units in Terpenes
O
OH
Limonene Camphor -Pinene
-Selinene Guaiol
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Non-Isoprenoid Terpenes
O
Valerane
-VetivoneEremophilone
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Alkaloids
Nitrogen containing, basic natural products often have powerful biological activityalkaloids are not as conveniently organized
by some common structural component.
N H N
H
N
N
N H
N H
NH
Me
Pyrrolidine
Piperidine
Tropane
Pyrrolizidine
IndoleQuinoline
Isoquinoline
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Examples of alkaloids
N H
O
N Me
HO
HO
N
AcO
NH2
N
N
O
O
N
NHO
MeO
N H
N
MeOOC
N H
NMe
COOMe
HO
COOMe
MeO
Quinine
Strychnine
MorphineSlaframine
Coniine
Vinblastine
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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.
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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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