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Secondary Metabolites from Plants
David S.-Y. Wang
Assistant Professor
Department of Forestry, NCHU
Plant Secondary Metabolites
Secondary metabolites are those metabolites which are often
produced in a phase of subsequent to growth, have no function in
growth (although they may have survival function), are produced by
certain restricted taxonomic groups of microorganisms, have unusual
chemicals structures, and are often formed as mixtures of closely
related members of a chemical family.
The simplest definition of secondary products is that they are
not generally included in standard metabolic charts.
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Plant Secondary Metabolites
A metabolic intermediate or product, found as a differentiation
product in restricted taxonomic groups, not essential to growth and
the life of the producing organism, and biosynthesis from one or
more general metabolites by a wider variety of pathways than is
available in general metabolism.
Secondary metabolites are not essential for growth and tend to
be strain specific. They have a wide range of chemical structures
and biological activities. They are derived by unique biosynthetic
pathways from primary metabolites and intermediates.
Plant Secondary Metabolites
Biochemical pathways that are not necessary for growth
or reproduction of an organism, but which can be
demonstrated genetically, physiologically or
biochemically.
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Plant Secondary Metabolites
Plants produce as amazing diversity of low molecular
weight compounds.
Of the estimated 400,000 500,000 plant species around
the globe, only a small percentage has been investigated
phytochemically and the fraction subjected to biological or
pharmacological screening is even lower.
Plant Secondary Metabolites
The ability to synthesize secondary metabolites has
been selected through the course of evolution in different
plant lineage when such compounds address specific
needs.
Floral scent volatiles and pigments have evolved to attract
insect
pollinators and thus enhance fertilization.
To synthesize toxic chemical has evolved to ward off
pathogens
and herbivores or to suppress the growth of neighboring
plants.
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Plant Secondary Metabolites
Chemicals found in fruits prevent spoilage and act as signals
(in
the form of color, aroma, and flavor) of the presence of
potential
rewards (sugars, vitamins and flavor) for animals that eat the
fruit
and thereby help to disperse the seeds.
Other chemicals serve cellular functions that are unique to
the
particular plant in which they occur (e.g. resistance to salt
or
drought).
Natural Products Drug Discovery and Development
Over the ages, human have relied on nature fro their
basic needs for the production of foodstuffs, shelters,
clothing, means of transportations, fertilizers, flavors and
fragrances, and not least medicine.
Plants have formed the basis of sophisticated traditional
medicine system that have been in existence thousands
of years in countries such as China and India.
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Natural Products Drug Discovery and Development
About 25% of all prescriptions sold in the US are for
natural products, while another 25% are for structural
modifications of a natural products.
According to Fransworth (1990) claims that 119
characterized drugs are still obtained commercially from
higher plants and that 74% were found from
ethnobotanical information.
. Fransworth, N.R. (1990) In bioactive compounds from
plants.
John and Wiley Co..
Primary and Secondary Metabolism
Primary metabolism
The biological reactions are essential to maintain life in
living
organisms and are known as primary metabolism.
Plant convert sunlight energy to chemical energy, such as
ATP,
NADPH, by the mediation of chlorophyll in chloroplasts and
synthesize sugars and starch from CO2 by using ATP and
NADPH+.
These carbohydrates are stored and used for differentiation
and formation of plant tissues.
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Primary and Secondary Metabolism
Secondary metabolism
The metabolisms which are not directly related to
maintaining
life, are known as secondary metabolisms.
The products formed by secondary metabolism are called
secondary metabolites.
Secondary metabolite play a role in reinforcement of tissue
and
tree body (e.g. cellulose, lignin, suberin), protection
against
insects, dieses, and plant regulation (plant hormones).
Primary and Secondary Metabolism
All organisms need to transform and interconvert a vast number
of organic compounds to enable them to live, grow and
reproduce.
All organisms need to provide themselves with energy in the form
of ATP, and a supply of building blocks to construct their own
tissues.
An integrated network of enzyme-mediated and carefully regulated
chemical reactions in used for this purpose, collectively referred
to as intermediary metabolism, and the pathways involved are termed
metabolic pathway.
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Primary and Secondary Metabolism
The pathways for generally modifying and synthesizing
carbohydrates, proteins, fats, and nucleic acids are
found to be essentially to same in all organisms, apart
from minor variations.
These processes demonstrate the fundamental unity of all
living
matter, and are collectively described as primary
metabolism,
with the compounds involved in pathways being termed primary
metabolites.
Primary Metabolisms
Degradation of carbohydrates and sugars generally
proceeds via the well characterized pathways, known as
glycolysis and the kerbs / citricacid / tricarboxylic acid
cycle, which release energy from the organic compounds
by oxidative reactions.
Oxidation of fatty acids from fats by the sequence called
-oxidation also provides energy.
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Primary Metabolisms
Aerobic organisms are able to optimize these processed by
adding on a further process, oxidative phosphorylation.
This improves the effeiciency of oxidation by incorporating
a more general process applicable to oxidation of a wide
variety of substrates rather then having to provide specific
process for each individual substrate.
Primary Metabolisms
Proteins taken in via the diet provide amino acids, but
the proportions of each will almost certainly vary from the
organisms requirements.
Most organisms can synthesize only a proportion of the
amino acids they actually require for protein synthesis.
Those structures not synthesized, so-called essential
amino acids, must be obtained from external sources.
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Secondary Metabolisms
The compounds which synthesized from the secondary metabolisms
are so-called secondary metabolites.
Secondary metabolites are formed in only specific organisms, or
groups of organisms, ane are expressioin of the individuality of
species.
Secondary metabolites are not necessarily produced under all
conditions, and in the vast majority of cases the function of these
compounds and their benefit to the organism is not yet known.
It is this area of secondary metabolism that provides most of
the pharmacologically active natural products.
Secondary Metabolisms
To make such compounds as sugars, waxes, lignin starch,
pigments,
or alkaloids, plants utilize very specific enzymes, each of
which
catalyzes a specific metabolic reaction.
The enzymes are proteins called organic catalysts.
These enzymes are coded by specific genes in the plants DNA and
are
made via processed we call transcription and traslation.
When there is a series of enzymatically catalyzed reaction in a
well-
defined sequence of step, we have what is termed a metabolic
pathway.
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Biosynthetic Pathway
Nucleoside diphosphate sugar pathway: cellulose,
hemicellulose, glycosides.
Shikimate-cinnamate pathway: lignin, lignans,
hydrolyzed tannins.
Mixed pathways of 3 and 4: some prenylflavonoids,
quinones and stilbenes.
Primary and Secondary Metabolism
Primary and secondary metabolites leave a grey area
at the boundary, so that some groups of natural products
could be assigned to either divisions.
Primary metabolites Biochemistry
Secondary metabolites Natural products Chemistry
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The Classes of Secondary Metabolites
The majority of secondary metabolites belong to one of a number
of families, each of which have particular structural
characteristics arising from the way in which they are built up in
nature (biosynthesis).
The classes of secondary metabolites are: Polyketides and fatty
acids
Terpenoids and steroids
Phenylpropanoids
Alkaloids
Others (specialize amino acids and carbohydrates)
Polyketide and Fatty acids
Polyketides are formed by the linear combination of acetate
units derived from the building block acetyl co-enzyme A.
The acetate origin of these compounds leads to a preponderance
of even-numbered carbon chains.
Many plant oils and animal fats contain long-chain
monocarboxylic acids know as fatty acids.
In the fatty acids, the carbonyl group of the acetate units is
reduced during the course of the chain assembly process.
Dehydrogenation and oxidative processed may subsequently give the
unsaturated fatty acids.
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Polyketide and Fatty acids
The common fatty acids have an even number of
carbon atoms, typically C12 C20, linked together in a
straight chain with up four double bonds.
In plants the fatty acids and the corresponding alcohol
are found in leave waxes and seed coating:
Myristic acid (C14) is found in nutmeg seeds.
Palmitic acid (C16) is found in almost all plant oils.
Stearic acid (C18) occurs in long amounts in animal
fat.
Polyketide and Fatty acids
Unsaturated fatty acids are important to us in food. Oleic acid
is the most widely
distributed, and a major constituent of olive oil.
Linoleic and linolenic acids are most highly unsaturated and are
found in linseed oil.
Linolenic acid is easily oxidized by air, and is one of the
drying oil used in paint and varnishes.
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Polyketide and Fatty acids
Linolenic acid is oxidized
by plants to jasmonic acid,
which is a signaling
substances that stimulates
plant defense mechanisms.
Arachidonic acid (C20) is a
precursors of the
prostaglandin hormones.
Polyketide and Fatty acids
Polyacetylenes
They are a group of naturally
occurring hydrocarbon
derivatives characterized by
one or more acetylenic groups
in their structures.
Araliaceae(),
Campanulaceae(),
Apiaceae(),
Asteraceae, Pittosporaceae(
), and some fungi.
OH
OH
OH
O
O
COOH
OH
OH
Falcarinol
Safynol
Wyerone acid
1,2-dihdroxytrideca-5,7,9,11-tetrayne
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Terpenes
The terpenes are among the most widespread and
chemically diverse groups of natural products.
Terpenes are a unique group of hydrocarbon-based
natural products whose structures may be derived from
isoprene.
Terpenes are classified by the number of 5-carbon units.
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Terpenes
Isopentenyl pyrophosphate (IPP) and dimethylallyl
pyrophosphate (DMAPP) combined to yield geranyl
pyrophosphate (GPP), leading to monoterpenes.
Similarly, compounds derived from farnesyl
pyrophosphate (IPP) lead to sesquiterpenes, and
triterpenes are formed from two equivalents of FPP, and
triterpenes are formed from two equivalents of FPP.
Terpenes
The function of terpenes in plants is generally
considered to be both ecological and physiological
Allelophathy
Insecticidal
Insect pollinators
Plant hormone (Abscisic acid, gibberlellin)
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Myrcene
Greek Bay (Laurus nobilis)
Myrcene is found in the essential oil of bay leaves as well as
hops. It is used as an intermediate in the manufacture of
perfumes.
Hops (Humulus lupulus)
Geraniol and Linalool
OH
Geraniol is isomeric with linalool, constitutes the major part
of the oil of roses and is also found in essential oils of
citronella, lemon grass, and others.
Geraniol
OH
Linalool
citronella
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Menthol
OH
Menthol is a well-known monoterpenewhich is found in the
essential oil of peppermint and other members of the mint
family.
Sesquiterpenoids
More than 10000 sesquiterpenoids have been identified,
representing a wide variety compounds of different skeletal types
from acyclic to tetra cyclic systems.
-muurolene -cadinene -cadinol-cedrene
logifloene juniperol nootkatin chanootin
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cadinenes
OO
Osantonin
Wormwood(Artemisia maritima)
caryophyllene
Cloves (Syzygium aromaticum) OH
OO
Dandelion (Taraxacum officinale )
tetrahydroridentin B
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Bioactive Compounds Contributing to Decay Resistance of Taiwania
Wood
Fungi and termites are two of the most harmful organisms to
wooden structures worldwide
To develop methods for prolonging the service life of wood is
one of challenges of wood utilization researchers
As regards decay resistance, Taiwania is classified as the
species with an excellent durability in Taiwan
There are several papers dealing with the antifungal and
antitermitic activities of Taiwania:
.For. Prod. Industries. 1998, 17, 287.
.Holzforschung. 1999, 53, 487.
.Holzforschung. 2000, 54, 241.
. J. Chem. Eco. 2001, 27, 717.
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White rot fungi Brown rot fungi Coriolus versicolor Laetiporus
sulphureus
Lenzites betulina Antrodia taxa
Pycnoporus coccineus Fomitopsis pinicola
Trichaptum abietinum Phaeolus schweinitzii
Oligoporus lowei
Commonly Occurring Brown-rot and White-rot Fungi
Extractives of Taiwania against White-rot Fungi
Taiwania Heartwood
MeOH extraction
MeOH Extractives
Hex Fr.
Chl. Fr.
EtoAc Fr.
MeOH Fr.
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Extractives of Taiwania against Brown-rot Fungi
Taiwania Heartwood
MeOH extraction
MeOH Extractives
Hex Fr.Chl. Fr.
EtoAc Fr.
MeOH Fr.
Antifungal Indices of Compounds Isolated from Taiwania
Heatwood
0 20 40 60 80 100
L. s.
C. v.
Antifungal index
Suginol
Hinokiol
Ferruginol
-Cedrol
-Cadinol
Helioxanthin
Taiwanin C
Savinin
Taiwanin A
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Effectiveness of -Cadinol against White-rot and Brown-rot
Fungi
Among the compounds isolated from Taiwania heartwood,
-cadinolhas demonstrated to possess the highest antifungal
effectiveness.
H
OHH
H
OHH
H
OH
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Quantification of the Cadinane Skeletal Sesquiterpenoids
Distribution in Different Parts of Taiwania
GC chromatograms of essential oils distilled from Taiwania
heartwood.
H
OH
H
H
OH
H
H
OH 1
2
3
T-cadinol
T-muurolol
-cadinol
The amounts of hexane extractives and essential oils distilled
from various parts of Taiwania
0
2
4
6
8
Am
ount
s of
cad
inan
es (m
g/kg
) t-cadinolt-muurolol-cadinoltotal cadinols
Essential oil
Leafs Sapwood Heartwood
n-Hexextracts
Heartwood
Amounts of Cadinanes in Various Parts of Taiwania
6.49
1.77
0.360.04
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Antifungal Indices of -Cadinol, T-Cadinol, and T-Muurolol
Fungi -Cadinol T-Cadinol T-Muurolol
C. v. 100 47.1 38.8
L. s. 100 100 82
equatorial hydroxyl group
trans ring junction
Diterpenoids
Diterpenoids constitute a major
part of oleoresin.
This group can be divided into
acylic, bicyclic, tricyclic,
tetracyclic, and macrocyclic
structural types.
Diterpenoids are present either
as hydrocarbons or as
derivatives with hydroxyl,
carbonyl, or carboxyl groups.
geranyl-linalool -epimanool
cis-abienol manoyloxide
pimaral
pimarolcembrene
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Phenolic Constituents
Heartwood and bark
contain a large variety of
complex aromatic
extractives. Most of them
are phenolic compounds,
and many are derived
from the phenylpropanoid
structure.
Classification of Phenolic Compounds
Numbers of C Basic skeleton Name
6 C6 Benzoquinones
10 C6-C4 Naphthoquinones
14 C6-C2-C6 Stilbenes
15 C6-C3-C6 Flavonoids
17 C6-C3-C2-C6 Norlignans
18 (C6-C3)2 Lignans
n (C6-C3-C6)n Condensed tannins
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Phenolic Compounds
CHO
OCH3OH
Vanillin
OCH3
CH
O
CHH2COH
GLUCOSE
Coniferin
CHO
OCH3OH
CH3O
Syringaldehyde
OHOCH3
Guaiacol
OHOCH3
CH2CHCH2
Eugenol
O
OOCH3CH3O
2,6-Dimethoxybenzoquinone
Summery of the Biogenetic Connection between a Selection of
Familiar Phenolic metabolites
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Summery of the Biogenetic Connection between a Selection of
Familiar Phenolic metabolites
Summery of the Biogenetic Connection between a Selection of
Familiar Phenolic metabolites
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LignansIsolation Procedures
Lignans can be isolated from the bark, fruit, heartwood, leaves,
roots and resin of plants
Most isolation procedures involve solvent extraction,
chromatography separations, and crystallization
Lignan yields can vary from 0-30%
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LignansCommercialization
Large amount of research devoted to investigating medicinal
properties of lignans Particularly from tropical hardwoods and
grasses
Example 1999 reference: 35 lignans isolated from the twigs of
Tazus mairei
Antiviral Antitumor Biocidal Bioactive Agents
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The heartwood of Taiwania is
yellowish red with
distinguished purplish pink
streaks, which fascinates
people very much.
The yellowish red color in
Taiwania is susceptible to
change to dull black after
exposure it to nature
environment.
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Optical Micrographs of Different Parts of Taiwania
Optical Micrograph Observation of Discoloration in Red Taiwania
Heartwood
2 weeks 4 weeks
After exposed Taiwania heartwood under indoors condition, its
color changed from red to dull black.
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Color Compounds Isolated from Taiwania Heartwood
O O
O
O
O
O
OH
H
H OH
O
OO
O
OO
OO
O
OO
O
O
O
OO
OH
OH
OOH
O O
OH
OMe
CHO
OH
CHO
Taiwanin A Savinin Helioxanthin Pluviatolide
Taiwanin I Ferruginol T-Cadinol Secoabietane dialdehyde
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Cytotoxicity of Lignans and Sesquiterpenoids from Taiwania
Heartwood (ED50 values in mM)
Taiwanin A
Taiwanin E
-CadinolDimethylmatairesinol
Cytotoxicity of Dibenzyl--butyrolactone Type of Lignans Isolated
from Taiwania Heartwood
An unsaturated double bond between C7-C8 and/or C7-C8is
associated with stronger cytotoxicity.
The presence of two 3, 4-dimethoxyphenyl groups in lignans may
increase the cytotoxicity, as dimethyl-matairesinol was stronger
than arctigenin and hinokinin
O
O O
OO O
OO
O
OO
O
O
R
R
RR
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Cytotoxicity of Dibenzyl--butyrolactone Type of Lignans Isolated
from Taiwania Heartwood
An unsaturated double bondbetween C7-C8 and/or C7-C8is
associated with stronger cytotoxicity.
The presence of two 3, 4-dimethoxyphenyl groups in lignans may
increase the cytotoxicity, as dimethyl-matairesinol was stronger
than arctigenin and hinokinin
O
O O
OO O
OO
O
OO
O
O
R
R
RR
Cytotoxicity of Dibenzyl--butyrolactone Type of Lignans Isolated
from Taiwania Heartwood
An unsaturated double bondbetween C7-C8 and/or C7-C8is
associated with stronger cytotoxicity.
The presence of two 3, 4-dimethoxyphenyl groups in lignans may
increase the cytotoxicity, as dimethyl-matairesinol was stronger
than arctigenin and hinokinin
O
O O
OO O
OO
O
OO
O
O
OMeMeO
MeO
MeO
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Cytotoxicity of Arylnaphthalide Type of Lignans Isolated from
Taiwania Heartwood
Taiwanin E showed the strongest cytotoxicity in this group.
It appears that the hydroxyl group at the C7 position enhances
the cytotoxicity.
OO
O
OO
O
OO
O
OO
O
OH
O
OO
OO
O
Cytotoxicity of Arylnaphthalide Type of Lignans Isolated from
Taiwania Heartwood
Taiwanin E showed the strongest cytotoxicity in this group.
It appears that the hydroxyl group at the C7 position enhances
the cytotoxicity.
OO
O
OO
O
OO
O
OO
O
OH
O
OO
OO
O
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Flavonoids/TanninsIsolation of Flavonoids
Isolation of flavonoids accomplished through solvent extraction
Hot water Alcohols
Solvent fractionation of extract Salting out Crystallization
Flavonoids/TanninsIsolation of Flavonoids
Flavonoids concentrated in certain parts of plants
Plant sources Pulp of fruits
Broccoli, green peppers, onions, etc.
Green tea, red wine
Herbs
Tree bark
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Blockade of tumor induction by EGCG
O
OC
O
OH
OH
OH
OH
OH
OH
OH
OH
(-)-epigallocatechin-3-gallate
GST: glutathione S-transferaseGlcT: UDP-glucuronyl
transferaseROS: reactive oxygen
(superoxide anion, hydrogen peroxide,hydroxyl radical, nitric
oxide, peroxynitrite, and nitric dioxide anion)
RH: procarcinogens(aflatoxins, poly-cyclic aromatic
hydrocarbons, and nitrosamines)
Chemical Composition of Tea
Caffein: 3-4 %
Catechins (including Tannin): 15-30 %
Flavonols and Metal: 5 %
P,K, Ca, Mg, Mn, Zn, Cu, Al
Vitamins: A, B1, B2, C, E, Nicotinic acid
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Flavonoids/TanninsPolymerization Reactions
Condensed tannins are formed through the polymerization of
flavan-3-ol (catechin) and flavan3,4-diols (leucoanthocyanidins) In
tree, polymerization
through acidic enzymatic non-oxidative coupling
2-50 units Typically 2-8
Linkages can be through a variety of sites
O
OHOH
Flavan-3,4-diols(Leucoanthocyanidins)
O
OH
Flavan-3-ols(Catechins)
Flavonoids/TanninsPolymerization Reactions
Examples of linkages 4 alpha 8 4 beta 8 4 beta 6
Stereochemistry A variety of monomers
O
A
B
C2
3
456
78
2'3'
4'
5'6'
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Flavonoids/TanninsPolymerization Reactions
O
OH
OHOH
OH OH
HO
O
OH
OHOH
OH
HO
O
OH
OHOH
OH
HOO
OH
OHOH
OH
O
O
OH
OHOH
OH
HO
O
OH
OHOH
OH
OH
OHOH
OH
O
HO
HO
(H+)
-H2O
+ H+
(+)
- H+
Flavonoids/TanninsPolymerization Reactions
Flavan-3-ols are incapable of polymerizing without flavan
3,4-diol
Flavan-3-ol form terminating unit
O
OH
O OH
OH
OH
OH
OH
O OH
OHOH
HO HO
HO
HO
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Flavonoids/TanninsPolymerization Reactions
All 4-8 linkages
This structure has
been isolated from
pine bark
O
OH
OHOH
OH
OH
OHOH
OH
O
OH
OHOH
OH
O
HO
HO
HO
Flavonoids/TanninsPolymerization Reactions
Flavan-3-ols can polymerize through an oxidative enzymatic
coupling reaction forming oligo and polymeric materials Linkages
8-6 Causes loss of
brightness in wood
O
OHOH
OH O
OOH
OHOH
O
HO
HO
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Flavonoids/TanninsLocation in Tree: Tannins
Western hemlock Bark: 18% tannins Wood: 2% tannins
Quebracho In wood, tannins found in heartwood Majority (80%)
located in vessel lumina Tannins deposit in dead cell starting at
CML and
ending in secondary wall
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Condensed TanninsProperties
The term condensed tannins refers to a mixture of polyflavonoids
of different MW (500-5000) characterized by different linkages,
functional groups, and stereochemistry.
Protein binding capacity: tannins will bind with proteins
causing them to precipitate. This was the definition of tannins:
compound which
will precipitate proteins.
Condensed TanninsSources
Condensed tannins more prevalent in
hardwoods but present in softwoods
Wattle (Acacia - Southern Africa)
Quebracho (Schnopsis - South America)
Mangrove (Rhizophora -)
Hemlock (North America)
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Condensed TanninsBiological Significance Insects/Animals
Protection of plants against insects/animals Some evidence
for/some against
Bad Taste/Astringency (bitter taste) Appears to be major
factor
Particularly bad for insects not used to tannins
Animals: tannins reduce digestion of food Interaction with
digestion enzymes
Toxic to bacteria
Condensed TanninsBiological Significance - Fungus
Pine calluses: created by fungal invasion
Tree forms calluses as protective tissue
Calluses contain high levels of tannins (Chinese 50-80%)
Concentrations of tannins as low as 0.1% or 0.8 % have been
shown to retard the growth of a large number of parasitic fungi
Quote: Edwin Haslam (tannin chemist)
serious and nagging fear that a part at least of (their)
scientific career(s) has been spent inspecting the loot in the
garbage bin of plant metabolism
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Hydrolyzable TanninsStructure
Polymers of a sugar (usually glucose) with one or more
polyphenolic carboxylic acids: linked through ester linkages
Gallotannins: Gallic acid polymer Ellagitannins: Ellagic Acid
polymer
COOH
OHOHHO
Gallic Acid
OHOH
CO
OH
OHC
HO
O
HOO
Digallic Acid
OH
C
O
OHOH
O
C
HO
O
O
Ellagic Acid
Hydrolyzable TanninsPolymer Structure Example
O
OO
OH
O
O
HO
HO
OH
O
HO
HO
O
OHOHO
OHOH
OH
O
OH
OH
OH
O
O
OH
OHO
O n
Sugar
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Hydrolyzable TanninsTree Information
Rare to nonexistent in softwoods
Hardwoods which contain large amounts:
Oak (gallic and ellagic tannins)
Eucalyptus (Ellagitannins)
Chestnut (gallic tannins)
Myrobalan fruits (cherry plum)
Hydrolyzable tannins located in heartwood
Condensed TanninsUses
Leather tanning: 10,000+ year old industry Vegetable tannins
& chrome Tannins interacting with proteins in hides
Adhesives In phenol formaldehyde systems, tannins
speed up the set:
Oil well drilling fluids: old but effective use: taken over by
chrome lignosulfonates
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Stilbene -Diphenylethylene
Alkaloids
Derived from plants
With a basic character (hence the term
alkaloid from alkali)
Contained a nitrogen based heterocylic
ring within their molecules
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Alkaloids can be sub-categorized according to: Monocyclic
alkaloids Bicyclic alkaloids Polycyclic alkaloids
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OpiumPapaver somniferum - used for 5000 years. Arabs introduced
opium to China in 7th century. Opium addiction became a problem so
Chinese officials outlawed it. England traded opium to China for
goods even though it was illegal in their own country and in China.
China and England fought two wars over the English import of opium,
China lost both, ceded Hong Kong to British at end of first war.
Use of opium in China did not drop until Communist Revolution in
1949. Most opium is currently grown in SE Asia.
Morphine is purified from opium and is a very potent
painkiller.
Narcotic analgesics
OR
OH
N CH3
O
R = H morphineR = CH3 codeine
Ephedra sinica,
Ephedra intermedia,
Ephedra equisetina
Ma huang
Ma Huang or Ephedra has been used in China since 2800 BC It was
used primarily for colds, asthma, hayfever, bronchitis, edema,
arthritis, fever, hypotension and hives. Potency is based upon the
herb's alkaloid content. Side effects include increased blood
pressure, heart rate and anxiety. FDA suggest that those with heart
(disease or high blood pressure), thyroid, diabetes or prostrate
problems may be affected adversely. It should definitely NOT be
taken with antihypertensive or antidepressant drugs.
CCCH3
NH
CH3HH OH C
CCH3
NH
CH3HOH H
d-pseudoephedrinel-ephedrine
-
50
Vinblastine is a drug used in the treatment of cancer. It
interferes with the multiplication of cancer cells and slows or
stops their growth and spread in the body.
Catharanthus roseus
Berberis fremontii
-
51
-
52