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.

1
 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.

2
 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.

3
 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.

4
 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.

5
 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.

6
 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

β-oxidation also provides energy.

7
 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

organism’s 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.

8
 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.

9
 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

10
 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.

11
 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.

12
 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 Falcarinol

OH
occurring hydrocarbon
derivatives characterized by O

one or more acetylenic groups O COOH

Wyerone acid
in their structures.

– Araliaceae(五加科),
OH
Campanulaceae(桔梗科), Safynol
HO

Apiaceae(繖形花科),
Asteraceae, Pittosporaceae(海 OH

桐科), and some fungi. 1,2-dihdroxytrideca-5,7,9,11-tetrayne OH

13
14
 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.

15
 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)

16
 Myrcene

Greek Bay (Laurus nobilis) Hops (Humulus lupulus)

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.

Geraniol and Linalool

OH
OH

Geraniol Linalool

Geraniol is isomeric with linalool, constitutes the

citronella
major part of the oil of roses and is also found in
essential oils of citronella, lemon grass, and others.

17
 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.

α-cedrene
α-muurolene δ-cadinene α-cadinol

logifloene juniperol nootkatin chanootin

18
 cadinenes

Wormwood
(Artemisia maritima)

O
O
O
santonin

caryophyllene Dandelion (Taraxacum officinale )

Cloves (Syzygium aromaticum) OH

O
O

tetrahydroridentin B

19
 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.

20
Commonly Occurring Brown-rot and
White-rot Fungi

White rot fungi Brown rot fungi

Coriolus versicolor Laetiporus sulphureus

Lenzites betulina Antrodia taxa

Pycnoporus coccineus Fomitopsis pinicola

Trichaptum abietinum Phaeolus schweinitzii

Oligoporus lowei

Extractives of Taiwania against White-

rot Fungi
Taiwania Heartwood

MeOH extraction

MeOH Extractives

Hex Fr.

Chl. Fr.

EtoAc Fr.
MeOH Fr.

21
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

Suginol
Hinokiol
C. v. Ferruginol
α-Cedrol
α-Cadinol
Helioxanthin
Taiwanin C
L. s.
Savinin
Taiwanin A

0 20 40 60 80 100
Antifungal index

22
Effectiveness of α-Cadinol against
White-rot and Brown-rot Fungi

• Among the compounds

isolated from Taiwania
heartwood, α-cadinol
has demonstrated to
possess the highest
antifungal effectiveness.
O
H

O
H
H

O
H
H

23
Quantification of the Cadinane Skeletal Sesquiterpenoids
Distribution in Different Parts of Taiwania
O
H
H

T-cadinol
The amounts of hexane extractives and essential
O
H
H

1
oils distilled from various parts of Taiwania

T-muurolol
H

2
H

O
H

α-cadinol
H

GC chromatograms of essential oils distilled

from Taiwania heartwood.

Amounts of Cadinanes in Various Parts of Taiwania

8
t-cadinol
Amounts of cadinanes (mg/kg)

6.49
t-muurolol
6 α-cadinol
total cadinols

2
1.77

0.36
0.04
0
n-Hex
Essential oil extracts
Leafs Sapwood Heartwood Heartwood

24
 Antifungal Indices of α-Cadinol, T-Cadinol,
and T-Muurolol
equatorial
hydroxyl group

trans ring junction

Fungi α-Cadinol T-Cadinol T-Muurolol

C. v. 100 47.1 38.8

L. s. 100 100 82

Diterpenoids

• Diterpenoids constitute a major

part of oleoresin.

• This group can be divided into geranyl-linalool β-epimanool

acylic, bicyclic, tricyclic,
tetracyclic, and macrocyclic
structural types.
cis-abienol manoyloxide
• Diterpenoids are present either
as hydrocarbons or as
derivatives with hydroxyl,
pimaral
cembrene
carbonyl, or carboxyl groups. pimarol

25
 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

26
 Phenolic Compounds
H2COH
CH2
CH
CH CH
CHO CH2

OCH3
OCH3 OCH3
OH O GLUCOSE OH

Vanillin Coniferin Eugenol

CHO O
CH3O OCH3

CH3O OCH3 OCH3

OH OH O

Syringaldehyde Guaiacol 2,6-Dimethoxy

benzoquinone

Summery of the Biogenetic Connection between a Selection

of Familiar Phenolic metabolites

27
Summery of the Biogenetic Connection between a Selection
of Familiar Phenolic metabolites

Summery of the Biogenetic Connection between a

Selection of Familiar Phenolic metabolites

28
 Lignans
Isolation 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%

29
 Lignans
Commercialization

• 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

30
• 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.

31
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.

32
 Color Compounds Isolated from
Taiwania Heartwood
O O
O O
HO
O O
O O O O
O O O HO
O

O O O O O
O O O
Taiwanin A Savinin Helioxanthin Pluviatolide

OH OH
OH
HO H
HO O

CHO
H CHO
OMe O O

Taiwanin I Ferruginol T-Cadinol Secoabietane dialdehyde

33
 Cytotoxicity of Lignans and Sesquiterpenoids from Taiwania
Heartwood (ED50 values in mM)

Taiwanin A

Taiwanin E

Dimethylmatairesinol
α-Cadinol

Cytotoxicity of Dibenzyl-γ-butyrolactone Type of

Lignans Isolated from Taiwania Heartwood

O
O
O
• An unsaturated double bond
O
O
O
O between C7-C8 and/or C7’-C8’
is associated with stronger
O O
O
O cytotoxicity.

O
• The presence of two 3, 4-
R
O
dimethoxyphenyl groups in
R
lignans may increase the
R
cytotoxicity, as dimethyl-
R
matairesinol was stronger than
arctigenin and hinokinin

34
 Cytotoxicity of Dibenzyl-γ-butyrolactone Type of
Lignans Isolated from Taiwania Heartwood

O
O
O
• An unsaturated double bond
O
O
O
O between C7-C8 and/or C7’-C8’
is associated with stronger
O O
O
O cytotoxicity.

O
• The presence of two 3, 4-
R
O
dimethoxyphenyl groups in
R
lignans may increase the
R
cytotoxicity, as dimethyl-
R
matairesinol was stronger than
arctigenin and hinokinin

Cytotoxicity of Dibenzyl-γ-butyrolactone Type of

Lignans Isolated from Taiwania Heartwood

O
O
O
• An unsaturated double bond
O
O
O
O between C7-C8 and/or C7’-C8’
is associated with stronger
O O
O
O cytotoxicity.

O
• The presence of two 3, 4-
MeO
O
dimethoxyphenyl groups in
MeO
lignans may increase the
OMe
cytotoxicity, as dimethyl-
MeO
matairesinol was stronger than
arctigenin and hinokinin

35
 Cytotoxicity of Arylnaphthalide Type of Lignans
Isolated from Taiwania Heartwood

• Taiwanin E showed the

O
OH
O
O strongest cytotoxicity
O
O
O
O
O
O
in this group.
O O O

O O O
• It appears that the
O O O
hydroxyl group at the
C7 position enhances
the cytotoxicity.

Cytotoxicity of Arylnaphthalide Type of Lignans

Isolated from Taiwania Heartwood

• Taiwanin E showed the

O
OH
O
O strongest cytotoxicity
O
O
O
O
O
O
in this group.
O O O

O O O
• It appears that the
O O O
hydroxyl group at the
C7 position enhances
the cytotoxicity.

36
 Flavonoids/Tannins
Isolation of Flavonoids
• Isolation of flavonoids accomplished
through solvent extraction
– Hot water
– Alcohols
• Solvent fractionation of extract
• Salting out
• Crystallization

Flavonoids/Tannins
Isolation 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

37
Blockade of tumor induction by
EGCG
OH
OH

HO O
OH
OH
O
OH C OH
O
OH

(-)-epigallocatechin-3-
gallate
RH: procarcinogens
(aflatoxins, poly-cyclic aromatic
hydrocarbons, and nitrosamines)

GST: glutathione S-transferase

GlcT: UDP-glucuronyl transferase
ROS: reactive oxygen
(superoxide anion, hydrogen peroxide,
hydroxyl radical, nitric oxide,
peroxynitrite, and nitric dioxide anion)

Chemical Composition of Tea

• Caffein: 3-4 %

• Catechins (including Tannin): 15-30 %

• Flavonols and Metal: 5 %

¾P,K, Ca, Mg, Mn, Zn, Cu, Al

• Vitamins: A, B1, B2, C, E, Nicotinic acid

38
 Flavonoids/Tannins
Polymerization Reactions
• Condensed tannins are
formed through the O

polymerization of flavan-3-ol OH
(catechin) and flavan–3,4- OH
Flavan-3,4-diols
diols (leucoanthocyanidins) (Leucoanthocyanidins)
– In tree, polymerization
through acidic enzymatic O

non-oxidative coupling
OH
– 2-50 units
Flavan-3-ols
• Typically 2-8 (Catechins)
– Linkages can be through a
variety of sites

Flavonoids/Tannins
Polymerization Reactions

3'
• Examples of linkages 2'
4'
– 4 alpha – 8 8 B
O 2 5'
7
– 4 beta – 8 A C 6'
6 3
– 4 beta – 6
5 4
• Stereochemistry
• A variety of monomers

39
 Flavonoids/Tannins
Polymerization Reactions
OH OH OH
OH OH OH

HO O O O O
HO
-H2O
OH + OH OH
(H )
OH OH OH OH

OH
OH +H
+

OH O OH
HO
OH OH
OH
OH OH
O HO O
HO OH
+ HO O
-H OH
OH
OH OH (+)
OH
OH

Flavonoids/Tannins
Polymerization Reactions
• Flavan-3-ols are
OH
incapable of O
HO OH
polymerizing without
OH
OH
flavan 3,4-diol HO
HO

• Flavan-3-ol form
terminating unit O OH O
OH

HO OH
OH
OH

40
 Flavonoids/Tannins
Polymerization Reactions
OH
OH
• All 4-8 linkages
HO O

OH
• This structure has OH OH
OH
been isolated from HO O

OH
pine bark OH
OH
OH

HO O

OH
OH

Flavonoids/Tannins
Polymerization Reactions

• Flavan-3-ols can
OH
polymerize through OH

an oxidative HO O
enzymatic coupling OH
OH
reaction forming OH O
O
oligo and polymeric HO

materials
OH O
– Linkages 8-6’
– Causes loss of
brightness in wood

41
 Flavonoids/Tannins
Location 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

42
 Condensed Tannins
Properties
• 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 Tannins
Sources
• Condensed tannins more prevalent in
hardwoods but present in softwoods
– Wattle (Acacia - Southern Africa)

– Quebracho (Schnopsis - South America)

– Mangrove (Rhizophora -)

– Hemlock (North America)

43
 Condensed Tannins
Biological 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 Tannins
Biological 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”

44
 Hydrolyzable Tannins
Structure
• Polymers of a sugar (usually glucose) with one or
more polyphenolic carboxylic acids: linked through
ester linkages
• Gallotannins: Gallic acid polymer
• Ellagitannins: Ellagic Acid
OH
polymer
HO OH OH
HO

O C O C O
OH O
HO OH O C O
OH

OH
HOOC OH
COOH OH

Digallic Acid Ellagic Acid

Gallic Acid

Hydrolyzable Tannins
Polymer Structure Example
OH
OH

OH
O OH
Sugar
HO
O
HO O O O
O OH
O O
O OH
HO O OH

HO HO O
OH
OH
O OH n

OH
O

45
 Hydrolyzable Tannins
Tree 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 Tannins
Uses
• 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

46
Stilbene 二苯乙烯類之化合物是以α，β-Diphenyl
ethylene 為骨架之化合物稱之，廣泛地分
佈在針葉樹皮及闊葉樹之許多樹種。由於
具有共軛雙鍵，此類化合物為反應性極強
之化合物，除了在製漿蒸煮過程中會與藥
劑反應外，並會阻止可溶性之木質素磺酸
鹽的形成，阻礙木質素的溶解。此外，二
苯乙烯類亦與木材之抗蟻性有密切的關
係。

Alkaloids

• Derived from plants

• With a basic character (hence the term

alkaloid from alkali)

• Contained a nitrogen based heterocylic

ring within their molecules

47
• Alkaloids can be
sub-categorized
according to:
– Monocyclic
alkaloids
– Bicyclic alkaloids
– Polycyclic alkaloids

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Opium Narcotic analgesics
Papaver 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 OR

currently grown in SE Asia.

O
Morphine is purified from N CH3
opium and is a very potent R=H morphine
HO
painkiller. R = CH3 codeine

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
Ma huang anxiety. FDA suggest that those with heart
(disease or high blood pressure), thyroid,
Ephedra sinica,
diabetes or prostrate problems may be
Ephedra intermedia,
affected adversely. It should definitely NOT
Ephedra equisetina
be taken with antihypertensive or
antidepressant drugs.
CH3 CH3
H C N CH3 H C N CH3
H H
H C OH HO C H

l-ephedrine d-pseudoephedrine

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 Catharanthus roseus
長春花

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.

Berberis fremontii
小檗

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