Phenylpropanoids:

Definition: Phenylpropanoids represent a large group

of natural products containing a phenyl ring attached
to a three-carbon propane side chain(C6-C3) in their
structure.
Biosynthesis: Derived from the aromatic amino acids
phenylalanine and tyrosine or the intermediates of the
shikimic acid biosynthetic pathway.
Categories: Simple Phenylpropanoids
(phenylpropenes, phenylpropyl alcohols,
phenylpropionaldehydes, phenylpropionic acids)

Simple phenylpropanoids
Phenylpropenes
OCH3

H3CO

H3CO

OCH3
H3CO

H3CO

HO

anethole

eugenol

H3 CO

OCH3
beta-asarone

OCH3
alpha-asarone

CH2OH
H3CO

HO
coniferol

1-6
glc glc O

phenylpropy
l alcohols

CHO

CH2OH

syringinoside

cinnamaldehyde

Phenylpropionaldehy
des

Simple phenylpropanoids
phenylpropionic acids

HO

COOH HO

HO

HO

OH

O
COOH

OH
C
O

HO

OH

HOOC
HO
HO

ferulic acid
HO
HO

O
C

HOOC
rosmarinic acid

OH
C
O

OH

HOOC

danshensu

caffeic acid

H3 CO

COOH

OH

O
O C
OH

OH

3,4-dicaffeoyl quinic acid

chlorogenic acid
OH
OH
OH
HOOC

COOH

HO

OH
HO
OH

H3CO

OH
OH

quinic acid

OCH3
sinapic acid

Phenylpropanoid
synthesis

Shikimic Acid Pathway

Phosphenolpyruvate
CO2H
OP
CH2

+
CHO
OH
OH
OP
Erythrose-4-phosphate

CO2H
O
CH2
HO
OH
OH
OP

CO2H
OH
CH
HO
OH
OH
OP

"Arabino" 7-phosphate

Shikimic Acid Pathway

CO2H
OH
CH
HO

HO
O

OH
OH
OP

CO2H

CO2H

OH
OH

5-Dehydroquinic Acid

-H20

OH
OH

5-Dehydro
shikimic acid

Shikimic Acid Pathway

CO2H

OH
OH

5-Dehydro
shikimic acid

CO2H

CO2H

HO

OH

PO

OH

OH

OH

Shikimic acid

5-PhosphoShikimic acid

Shikimic Acid Pathway

Phosphenolpyruvate
CO2H
OP
CH2

+
CO2H

-H2O

O
CO2H

HO2C

CO2H

-H2O
-CO2
OH

PO

OH
OH

Prephenic Acid

Phenylpyruvic Acid

Shikimic Acid Pathway

O
CO2H

Phenylpyruvic Acid

NH2

NH2
CO2H

CO2H

OH
L-Phenylalanine

L-Tyrosine

Shikimic Acid Natural

Products
CH
CH
2

Eugenol

Anethole

CH3O
OMe

OH
CHO
CO2CH3
OH

Cinnamaldehyde

Methyl Salicylate

Phenylpropanoids:
Flavonoids water soluble plant pigments
Anthocyanidins improve microcirculation &
nightvision
Coumarins - Anticoagulants
Lignans Anti-cancer drugs
Tannins in green tea, red raspberry & witch
hazel

Structure and Classification:

Coumarins are lactones which are derived from phydroxycinnamic acids which undergo ortho hydroxylation then
ring closure between the ortho hydroxyl group and the
carboxylic group of the side chain, after a trans to cis
isomerization of the side chain double bond.
COOH
HO
p-hydroxycinnamic acid

O
1

6
7

coumarin

3
2
O

COOH
OH

cis-ortho-hyxroxycinnamic acid

Coumarins are widely distributed in higher plants, and

commonly found in families such as the Umbelliferae (Apiaceae)
and Rutaceae, both in the free form and as glycosides.

Coumarins:

HO

Coumarin

O
ONa

CH3

Warfarin Sodium

7-Hydroxycoumarin
"Umbelliferone"

Lignans: Structure and

Classification
Lignans are typically found as dimeric
phenylpropanoids derivatives and are found in
woody tissues and resin of plants.
Most of lignans are free form, seldom as
glycoside.
They have antitumor, antiviral, liver
protective, etc. activities.
The two phenylpropanoid units mostly linked
through the -C atom of the C3 side chains.

Properties:
Colourless crystal, no volatility, insoluble in
water, soluble in organic solvents.
Optical Activity: one or more chiral center.
The optical activity is related to biological
activities.
The optical activity is easily changed by acid.

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Structure and Classification

Classification:

Simple Lignans
Monoepoxylignans
Lignanolides
Cyclolignans

Lignans

Cyclolignolides
Bisepoxylignans
Dibenzocyclooctene lignans
Biphenylene lignans
Other lignans

Shikimic Acid Lignins

HO2C

OH

Gallic Acid

OH
Catechol

OH

OH

OH

OH
OH

OH
O

HO

OH

O
MeO

OH

OH
HO

OH

OMe

Podophyllotoxin
(A Lignan)

OH

OH
O

OH
Procyanidin B-1
A
syntheticTannin)
Lignan
(a condensed

Lignin a complex phenolic

Primary metabolite - secondary cell wall
component occurs in all vascular plants
Structural function
Also protective because deters
herbivores due to its toughness
Blocks growth of many pathogens
because only small group of fungi can
degrade

Lignin monomers

Polymer of three phenolic alochols

Different species have different ratios of
these monomers
Lignin in beech has 100:70:7 of coniferyl:
sinapyl: para-coumaryl

Flavinoids
One of the largest classes of
phenolics
Carbon skeleton has 15 carbons with
two benzene rings connected by a 3C bridge
-C3-

Flavonoids
Many have antimicrobial activity
anti-bacterial, anti-fungal, and anti-viral

Flavonoids in red wine responsible for

the French Paradox - lower risk of
heart attacks by inhibiting platelet
aggregation and blood clots

Flavinoids
Flavinoids classified into different
groups based on the degree of
oxidation of the 3-C bridge
Anthocyanins
Flavones
Flavonols
Isoflavones

Majority of flavinoids exist as

glycosides

Shikimic Acid Flavones

OH
HO

HO

OH O

OH O
A Flavone

An Isoflavone
OH

HO

O
OH

OH

An Anthocyanidin

OH

Anthocyanins
Colored
flavinoids - red,
pink, blue,
purple
pigments
Attract animal
pollinators and
seed dispersers

Flavones and Flavonols

Also flower pigments
Absorb UV not visible light - not visible
to human eye but visible to many
insects - maybe be attractants, nectar
guides
Also present in leaves where they
protect against UV-B damage
Appeared to be involved in legume
roots in attracting N-fixing bacteria

Isoflavonoids
Some have strong insecticidal
activity - rotenoids
Some have estrogenic/antiestrogenic activity and cause
infertility in mammals
Many are phytoalexins - antimicrobial
cmpds produced in response to
bacteria and fungi

Soy isoflavones
Isoflavones in soybean are thought
responsible for a host of beneficial effects
lower cholesterol, especially LDL - thereby
lower risk of cardiovascular disease
lower blood pressure
estrogenic effects reduce symptoms of
menopause and reduce risks of osteoporosis
inhibit growth of tumors and thought to be
responsible for low rates of breast and prostate
cancer among cultures eating soy products

Tannins
Tannin a general name for a large group of
complex phenolic substances that are
capable of tanning animal hides into leather
by binding collagen
Found in almost every plant part - abundant
in unripe fruit
Deter herbivores due to astringent properties
- bind saliva and other digestive proteins
Antimicrobial - tannins in heart wood prevent
decay

Tanins