Introduction to Natural Products - Colby · PPT file · Web view ·...
Transcript of Introduction to Natural Products - Colby · PPT file · Web view ·...
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• 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
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Isoprene
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Head
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Head
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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
HN
H
N
N
N
H
N
H
NH
Me
Pyrrolidine
Piperidine
Tropane
Pyrrolizidine
Indole
Quinoline
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
N
Me
COOMe
HO
COOMe
MeO
Quinine
Strychnine
Morphine
Slaframine
Coniine
Vinblastine
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AntiobioticsThere 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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