Download Feb 4

Course Plan
We will study effects of soil and stresses on plant
secondary products and see where it leads us
1. Learn more about plant secondary products
• Why do they make them?
• When do they make them?
• Where do they make them?
Pick some plants to study
•Capsicum (Chiles) = capsaicin
•Nicotiana (Tobacco) = nicotine
•Onions (Allium cepa)?= syn-Propanethial-S-oxide
•Garlic (Allium sativum)?= Alliin
•Radishes (Raphanus sativus) = glucosinolates
•Mustard (Brassica juncea) = glucosinolates
•Peppermint (Mentha × piperita) = menthol + many
•Catnip (Nepeta cataria) = nepetalactone
Stresses
1.Water
2.Nitrogen
3.Sulfur
4.Herbivory
5.Shaking
On Friday
Present a plant stressor, what is known about it, and why
it might affect plant 2˚ compounds in an ~ 10 minute
presentation.
Alternative: presenting another good plant/stressor
response to study and why we should choose it over the
ones already chosen.
Secondary Metabolites
1˚ metabolites are essential for growth & development
•therefore present in all plants
2˚ metabolites “not” required for growth & development
•therefore not present in all plants
Natural Products
1˚ metabolites are essential for growth & development
•therefore present in all plants
2˚ metabolites “not” required for growth & development
•therefore not present in all plants
•Often only found
in one or a few spp.
capsaicin
Nepetalactone Menthol
Natural Products
1˚ metabolites are essential for growth & development
•therefore present in all plants
2˚ metabolites “not” required for growth & development
•therefore not present in all plants
•Often only found
in one or a few spp.
Derived from 1˚
metabs
Natural Products
2˚ metabolites “not” required for growth & development
•therefore not present in all plants
•Often only found in one or a few spp.
Derived from 1˚ metabs,
can be hard to draw line
Natural Products
2˚ metabolites “not” required for growth & development
•therefore not present in all plants
•Often only found in one or a few spp.
Derived from 1˚ metabs, can be hard to draw line
Natural Products
2˚ metabolites not present in all plants
•Often only found in one or a few spp.
•Derived from 1˚ metabs, can be hard to draw line
•Can be up to 3% of dry weight: very expensive to the the
plant!
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
• Herbivores
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
• Herbivores
• Pathogens
Resveratrol
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
• Herbivores
• Pathogens
• Other plants
leptospermone
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
2. Attractant
• Pollinators
• Odors
• Colors
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
2. Attractant
• Pollinators
• Symbionts
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
2. Attractant
• Pollinators
• Symbionts
• Seed dispersers
Methyl anthranilate(strawberries)
Pentyl butyrate (pears, apricots)
Natural Products
>100,000 types; tremendous variety of functions
1.Defense
2.Attractant
• Pollinators
• Symbionts
• Seed dispersers
• “protectors” (tritrophic interactions)
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
2. Attractant
3. Protecting from UV
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
2. Attractant
3. Protecting from UV
4. metal uptake and transport
Natural Products
>100,000 types; tremendous variety of functions
1. Defense
2. Attractant
3. Protecting from UV
4. metal uptake and transport
5. Hardening cell walls
Natural Products
>100,000 types; tremendous variety of functions
Some are made constitutively
Natural Products
>100,000 types; tremendous variety of functions
Some are made constitutively
Others are induced, especially defense compounds
Natural Products
>100,000 types; tremendous variety of functions
Some are made constitutively, others are induced
Made in many cellular locations
• Cytoplasm: most hydrophilics
Natural Products
>100,000 types; tremendous variety of functions
Some are made constitutively, others are induced
Made in many cellular locations
• Cytoplasm: most hydrophilics
• Chloroplasts: terpenoids and some alkaloids
Natural Products
>100,000 types; tremendous variety of functions
Some are made constitutively, others are induced
Made in many cellular locations
• Cytoplasm: most hydrophilics
• Chloroplasts: terpenoids and some alkaloids
• Mitochondria: some alkaloids and some amines
Natural Products
>100,000 types; tremendous variety of functions
Some are made constitutively, others are induced
Made in many cellular locations
• Cytoplasm: most hydrophilics
• Chloroplasts: terpenoids and
some alkaloids
• Mitochondria: some alkaloids
and some amines
• Peroxisomes: some terpenoids,
convert glucosinolates to active
form upon pathogen attack
Natural Products
>100,000 types; tremendous variety of functions
Some are made constitutively, others are induced
Made in many cellular locations
• Cytoplasm: most hydrophilics
• Chloroplasts: terpenoids and some alkaloids
• Mitochondria: some alkaloids and some amines
• Peroxisomes: some terpenoids, convert
glucosinolates to active form upon pathogen attack
• Endoplasmic reticulum: fatty acid derivatives, other
nonpolars
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
• Some in all
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
• Some in all
• Others in specialized cells or tissues
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
• Some in all
• Others in specialized cells or tissues
• Some are transported in xylem or phloem from site of
synthesis to where they are stored
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
Many are stored in vacuole
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
Many are stored in vacuole
Others in plastids or ER
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
Some are stored in special cell types, eg trichomes
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
Some are stored in special cell types
Others in special cavities or ducts
Secretory cavity in lemon
Pine resin duct
Natural Products
>100,000 types; tremendous variety of functions
Made in many cellular locations
Made in many cell types
Some are stored in special cell types
Others in special cavities or ducts
Others in flowers, leaves or fruits
Natural Products
>100,000 types; 3 main groups
1. Terpenoids
2. Alkaloids
3. Phenolics
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
• Some with N, most w/o
• Monoterpenoids
mostly essential oils
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
• Some with N, most w/o
• Monoterpenoids
mostly essential oils
• Longer ones have
diverse functions
• Pigments
• Signals
• Defense
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
• Longer ones have diverse functions
• Pigments
• Signals
• Defense
• Phytoecdysterones mimic
ecdysone & cause molting
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
2. >12,000 Alkaloids: derived from amino acids: contain
N
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
2. >12,000 Alkaloids: derived from amino acids: contain
N
• Many drugs!
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
2. >12,000 Alkaloids: derived from amino acids: contain
N
• Many drugs! Mainly for defense.
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
2. >12,000 Alkaloids: derived from amino acids: contain
N
3. >8,000 phenolics: contain phenol ring
Natural Products
>100,000 types; 3 main groups
1. >30,000 terpenoids: made from isoprene units
2. >12,000 Alkaloids: derived from amino acids: contain
N
3. >8,000 phenolics: contain phenol ring
• Crucial for moving onto land! Strengthen cell wall
enough to support wt on land & transport water
Phenolics
>8,000 phenolics: contain phenol ring
• Crucial for moving onto land! Strengthen cell wall
enough to support wt on land & transport water
• Comprise ~40% of organic C in the biosphere (most
in cell walls)
Phenolics
>8,000 phenolics: contain phenol ring
• Crucial for moving onto land! Strengthen cell wall
enough to support wt on land & transport water
• Comprise ~40% of organic C in the biosphere (most
in cell walls)
• Many serve other functions:
• Pigments
Phenolics
>8,000 phenolics: contain phenol ring
• Crucial for moving onto land! Strengthen cell wall
enough to support wt on land & transport water
• Comprise ~40% of organic C in the biosphere (most
in cell walls)
• Many serve other functions:
• Pigments
• Signals
Phenolics
>8,000 phenolics: contain phenol ring
• Crucial for moving onto land! Strengthen cell wall
enough to support wt on land & transport water
• Comprise ~40% of organic C in the biosphere (most
in cell walls)
• Many serve other functions:
• Pigments
• Signals
• Defense
Phenolics
>8,000 phenolics: contain phenol ring
• Most are derived from phenypropanoid
Other natural products
~ 100 cyanogenic glycosides
• Release cyanide when plant is damaged
• Found in seeds of apricots, cherries, other fruits
Laetrile
Other natural products
> 100 glucosinolates: contain S and N
Other natural products
> 100 glucosinolates: contain S and N
• Mainly found in Brassicaceae (crucifers)
Other natural products
> 100 glucosinolates: contain S and N
• Mainly found in Brassicaceae (crucifers)
• Made from modified amino acids bonded to glucose
Other natural products
> 100 glucosinolates: contain S and N
• Mainly found in Brassicaceae (crucifers)
• Made from modified amino acids bonded to glucose
• Function in defense
Other natural products
> 100 glucosinolates: function in defense
When damaged release
1. Isothiocyanates
2. nitriles and elemental sulfur
3. Thiocyanates
4. oxazolidine-thiones
5. epithionitriles
Other natural products
The genus Allium produces sulfoxides derived from
cysteine
Other natural products
The genus Allium produces sulfoxides derived from
cysteine
When plants are damaged they are converted to pungent
volatiles