Ch 13: Secondary metabolism

and plant defense

1- First line of defense: Plant
perimeter protection
2- Second line of defense:
Chemical warfare
3- Three major groups of
secondary compounds
- Terpenes
- Phenolics
- N-containing compounds

Agricultural pests
economic damage
- cost Cotton
of prevention
and eradication
boll weevil

Fig. 11.13

Fig. 13.4

Classes of plant defenses

PHYSICAL DEFENSES
Spines, thorns
cutins
waxes
suberins

SECONDARY METABOLITES
Phenolics

Defense-related proteins

phenolic glycosides

peroxidases

bound phenolics

polyphenol oxidase

lignin?

PAL

condensed tannins

hydrolysable tannins

Terpenes
monoterpenes

N-containing
Alkaloids

diterpene acids

Mustard oils

Physical Defenses

Stem spines Colletia paradoxa

Leaf spines- Opuntia invicta

Shoot spines- Dovyalis

caffra

Otherwise known as kei apple

Drought tolerant

A closer look

 Why did spines often evolve in

areas that are dry or in other
ways stressful?
Other roles - competition,
camouflage?

Waxes, Cutins, and

Suberins

Cutin, Waxes, Suberins are

made of hydrophobic
compounds
Hydrophobic: having water-repelling
properties
These compounds are non-polar
Fatty acids are one type of
hydrophobic compound

Cutin
composed of long fatty acid chains
a major component of plant cuticle

Cutin
Plants cuticles
often vary with
the climate in
which they live.
Cactus cuticle

Cactus cuticle

Waxes
complex mixtures of long-chain lipids
that are extremely hydrophobic.
are synthesized by epidermal cells.
exuded through pores in the epidermal
cell wall by an unknown mechanism.

Suberin
Also formed from fatty acids but has a
different structure from cutin.
A cell wall constituent.

Suberin
often within roots.
can protect against pathogens and other
damage.
older parts of roots more suberized
endodermis has suberin side walls, water
must pass through plasma membrane to get to
stele

Suberin can form transport barriers

between the soil and the roots

Secondary Metabolites- a
term that has stuck

Secondary Compounds are

so-called because:
They do not play a role in
photosynthesis, growth, or
respiration. HOWEVER

Sec Plant secondary metabolites

ondary Compounds

protect primary metabolism by deterring

herbivores, reduce tissue loss.
also attract pollinators and seed-dispersing
animals.
formed from the byproducts or intermediates
of primary metabolism (see figure 13.4)

Constitutive vs. Induced

Defenses

Constitutive defense always present

Induced defense - synthesized

in response to challenge

Terpenes
Constituents of essential oils
Building block- 5 C isoprene unit
Terpenes are classified by the number of isoprene
units they have.
i.e. monoterpenes-1, diterpenes-4 etc.

Terpenes
produced from the mevalonic acid pathway
some functions in primary metabolism
function as herbivore deterrents
can be produced in response to herbivore
feeding, and to attract predatory insects
and parasites of the feeding herbivore.

Isoprene is the basic building block of the terpenes

(terpenes also called isoprenoids)

H3C
CH

CH

CH2

H2C
Monoterpenes have two C5 units (10C)
Sesquiterpenes have three C5 units (15C)
Diterpenes have four C5 units (20C)
Triterpenes 30 C
Tetraterpenes 40C
Polyterpenes ([C5]n), n>8

Terpene functions
1. Growth and development
carotenoid pigments are tetraterpenes
chlorophyll side chain is diterpene
giberellins (hormones) are diterpenes
abscissic acid (hormone) is a sesquiterpene C15
sterols are triterpenes

Terpene functions
2. As defensive compounds
toxins and feeding deterrenets to insects and mammals
Examples
resins of conifers are monoterpenes
essential oils - peppermint, limon, basil, sage
may be in glandular hairs on epidermis

Non-volatile

Volatile

Non-volatile terpenes - limonene

apparently distasteful to herbivores

Volatile terpenes such as menthol

broadcast a smell that warns herbivores
that the plant is toxic to them before

 Phytoecdysones are plant

steroids (within the
terpene class) that have
the same basic structure
as insect molting hormones
and thus interfere with
molting. These compounds
sometimes cause death of
the insect herbivore.

 Terpenes such as
pyrethrum (from
chrysanthemums) and
azadirachtin (from
the Asian and African
Neem tree) can be
used as natural
insecticides in
agricultural practices
or in horticulture.

Terpenes that act against vertebrate herbivores

Triterpenes
1. cardenolides (glycosides) - acutely toxic
influence Na+/K+ ATPase of heart muscle

beat

medicinal application - digitalis (from foxglove), used to

treat heart disease. Can slow and strengthen heart
2. Saponins (soaplike) - steroid, triterpenes glycosides
have lipid and water soluble parts of molecule
toxicity related to sterol binding, membrane
disruption

Genomic Organization of Plant

Terpene Synthases and
Molecular Evolutionary Implications
Trapp & Croteau, 2001
Some 30,000 known terpenes.
Phylogenetically widespread.
Common evolutionary origins
may predate angiosperms.
Extensive gene duplication events
may drive the diversity.

Prior to divergence of gymnosperms and

angiosperms, during the carboniferous, the
duplication of an ancestral terpene synthase
geneoccurred. Once copy of the duplicated
ancestral gene remained highly conserved in
structure and function, and this gene may have
contemporary descendants in the terpene
synthases involved in giberellins biosynthesis. The
second ancestral gene copy diverged in structure
and function, by adaptive evolutionary processes,
to yield a large superfamily of terpene synthases
involved in secondary metabolic pathways.

Terpenes as human medicinal drugs

limonene - monoterpenoid (C10) dietary anticarcinogen

Artemisnin - sesquiterpenoid (C15) antimalarial

Taxol - diterpenoid anticancer drug from Pacific yew (Taxus brevifolia)

Taxol from Pacific Yew, Taxus brevifolia

Taxol was isolated from bark of Pacific Yew in 1970s. Taxol
interferes with cell division by binding to the protein tubulin, a
key factor in mitosis. Taxol and related compounds now widely
used in treating breast and ovarian cancer.

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