Secondary

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metabolites
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Metabolites
Primary metabolites: Molecules that are
essential for growth and development of an essential for growth and development of an
organism.
Secondary metabolites: molecules that are not
essential for growth and development of an
i organism.
Secondary metabolism refers to compounds present in Secondary metabolism refers to compounds present in
specialized cells that are not necessary for the cells
survival but are thought to be required for the plants
surviv l in the envir nment
2
survival in the environment
Secondary metabolites are derived from primary metabolites
Plant Secondary Metabolites
Secondary compounds are grouped into classes based on similar
structures, common biosynthetic pathways where a chemical is
derived, or the kinds of plants that make them.
Often limited distribution among plants
A particular metabolite may be restricted to one species or one
s genus
Usually synthesized from primary products
Variety of functions recognized today but originally thought to
be waste products
The largest such classes are the N compounds (alkaloids +
glycosides), terpenoids, and phenolics.
Possibly over 250,000 secondary metabolites in plants
Why secondary metabolites? Why secondary metabolites?
Chemical warfare to protect plants from the Chemical warfare to protect plants from the
attacks by predators, pathogens, or
tit competitors
Attract pollinators or seed dispersal agents
I f bi i Important for abiotic stresses
Medicine
Industrial additives
5
Functions of Secondary Compounds Functions of Secondary Compounds
The most common roles for secondary compounds in
l t l i l l th t i t ti plants are ecological roles that govern interactions
between plants and other organisms.
(+)Many secondary compounds are brightly colored
pigments like anthocyanin that color flowers red and
blue. These attract pollinators and fruit and seed
dispersers dispersers.
(+) Nicotine and other toxic compounds may protect
th l t f h bi d i b the plant from herbivores and microbes.
(-) Other secondary compounds like rubber and
h d b l ( ) f b l h
( ) y p
tetrahydrocannabinil (THC) from cannabis plants have
no known function in plants.
Examples of plant secondary metabolites
High-Value/Low-Volume compounds may open up g p y p p
new markets for farmers.
Other Plant-derived Drugs
Terpenoids: The largest group Terpenoids: The largest group
Formed from 5-C subunits (isoprene synthesized )
Synthesized from G-3-P, pyruvate, and acetyl CoA
Compounds have from 10 to >40 carbons
Some terpenoids have functions in growth and development Some terpenoids have functions in growth and development
1. Plant hormones (gibberellins, abscisic acid)
2 Accessory pigments in photosynthesis 2. Accessory pigments in photosynthesis
Most terpenoids act as herbivory deterrents and are a prime
example of a biochemical arms race p
M (C 10) Monoterpenes (C-10)
Pyrethroid
insecticides
Conifer resins
Plant-plant defensive
communication
1 Deter pest 1. Deter pest
2. Attract pest
predators
Essential oils
Essential oils are often stored in surface glands Essential oils are often stored in surface glands
Sesquiterpenes (C-15) Sesqu terpenes (C 5)
Herbivory Herbivory
deterrents
(generalized)
Bitterness
Examples include E amp nc u
sagebrush and
sunflower
Diterpenes (C-20) Diterpenes (C-20)
Toxins and irritants (generalized)
Resins from some trees to seal
herbivore induced wounds herbivore-induced wounds
Human use has adapted these
compounds to anti-cancer drugs (Taxol
from Pacific yew)
Tri-terpenes (C-30)
More specialized toxins More spec al zed tox ns
Steroid in structure
Examples :
Cardenolides vertebrate heart toxins
Saponins detergent like structure p g u u
Additi l t i t Additional tri-terpenes
Phenolic compounds
Common element is a phenolic group
Derived from amino acids, principally phenylalanine p p y p y
Examples of phenolic compounds Examples of phenolic compounds
and their roles
Phenylpropanoids
Allelopathic compounds inhibit plant growth p p p g
Examples of phenolic compounds
and their roles
Furanocoumarins (celery, parsnip, and parsley)
Toxicity to insect herbivores Toxicity to insect herbivores
UV-activated toxins
Examples of phenolic compounds
d h l and their roles
Benzoic acid derivatives Benzoic acid derivatives
Systemic resistance to pathogens
Plant immune systems
Plant-wide response to Plant wide response to
a local infection
May involve both toxic
compounds like oxygen p yg
radicals
Can produce a memory
response
Examples of phenolic compounds
d th i l and their roles
Lignin g
Reinforcing molecule
(esp. in woody tissue)
D l b l Decreases palatability
T nnins Tannins
Flavor deterrent
Tea blackberry grape Tea, blackberry, grape,
apple
Mode of action is via
protein binding
Examples of phenolic compounds
and their roles
Flavonoids
Anthocyanins : Pigmentation (pollinator attractant) Anthocyanins : Pigmentation (pollinator attractant)
Flavones and Flavonols: UV protection and bee attractant
(nectar guides)
Isoflavones : Antimicrobial antiestrogenic Isoflavones : Antimicrobial, antiestrogenic
Nitrogen-Containing Compounds: Nitrogen Containing Compounds
Only chemical similarity is the presence Only chemical similarity is the presence
of nitrogen somewhere in the molecule
Well studied because of their toxicity
t i l d th i di i l l to animals and their medicinal value
Perhaps the most easily recognizable
group of secondary compounds in plants group of secondary compounds in plants
Examples of N containing E amp s of N conta n ng
compounds and their roles
Alkaloids
A large group of compounds found in 20% of A large group of compounds found in 20% of
all plant species
All contain a heterocyclic ring (i.e., a ring
formed from carbons and one nitrogen) formed from car ons and one n trogen)
Best known for their pharmacological effect Best known for their pharmacological effect
on animals
Examples of alkaloids Examples of alkaloids
Examples of alkaloids p
Examples of N-containing containing
Cyanogenic glycosides
A large group of compounds found in thousands of plant species
compounds and their roles
A large group of compounds found in thousands of plant species
Stored in leaves (cherry, Johnson grass), seeds (apple,
peach), or roots (cassava)
Enzymatic release of cyanide gas following herbivory y y g g y
Examples of N-containing compounds and their roles
Glucosinolates (mustard oil glycosides) Glucosinolates (mustard oil glycosides)
Principally found in plants from the Brassicaceae
Enzymatic release following herbivory
l l d f d ( d ) Volatile defensive compounds (toxins, deterrents)
Can also serve as attractants
Examples of N containing
N t i i id
compounds and their roles
Non protein amino acids
Interfere with herbivore protein synthesis
Replace normal amino acids to create nonfunctional Replace normal amino acids to create nonfunctional
proteins