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Phytochemistry of Medicinal Plants

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Medicinal plants are a rich source of bioactive phytochemicals or bionutrients. Studies carried out during the past 2–3 decades have shown that these phytochemicals have an important role in preventing chronic diseases like cancer, diabetes and coronary heart disease. The major classes of phytochemicals with disease-preventing functions are dietary fibre, antioxidants, anticancer, detoxifying agents, immunity-potentiating agents and neuropharmacological agents. Each class of these functional agents consists of a wide range of chemicals with differing potency. Some of these phytochemicals have more than one function. There is, however, much scope for further systematic research in screening Indian medicinal plants for these phytochemicals and assessing their potential in protecting against different types of diseases
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ISSN 2278- 4136
ZDB-Number: 2668735-5
IC Journal No: 8192
Volume 1 Issue 6
Online Available at www.phytojournal.com
Journal of Pharmacognosy and Phytochemistry
Vol. 1 No. 6 2013 www.phytojournal.com Page | 168
Phytochemistry of Medicinal Plants
Mamta Saxena*1, Jyoti Saxena1, Rajeev Nema2, Dharmendra Singh2 and Abhishek Gupta2
1. Sarojini Naidu Government Girls Post Graduate (Autonomous) College, Shivaji Nagar, Bhopal - 462016
(M.P.), India. [E-mail: mamtasaxena00@yahoo.co.in]
2. Center for Microbiology & Bio-Technology Research and Training, Bhopal, India
Medicinal plants are a rich source of bioactive phytochemicals or bionutrients.
Studies carried out during the past 2
3 decades have shown that these phytochemicals have an important role in preventing chronic diseases like cancer,
diabetes and coronary heart disease. The major classes of phytochemicals with disease-preventing functions are
dietary fibre, antioxidants, anticancer, detoxifying agents, immunity-potentiating agents and neuropharmacological
agents. Each class of these functional agents consists of a wide range of chemicals with differing potency. Some of
these phytochemicals have more than one function. There is, however, much scope for further systematic research in
screening Indian medicinal plants for these phytochemicals and assessing their potential in protecting against
different types of diseases
Keyword: Phytochemicals, Alkaloids, Terpenoids, Flavonoids, Saponins, Tannins and Phenolics.
1. Introduction
Phytochemicals (from the Greek word phyto,
meaning plant) are biologically active, naturally
occurring chemical compounds found in plants,
which provide health benefits for humans further
than those attributed to macronutrients and
micronutrients[1]. They protect plants from
disease and damage and contribute to the plant’s
color, aroma and flavor. In general, the plant
chemicals that protect plant cells from
environmental hazards such as pollution, stress,
drought, UV exposure and pathogenic attack are
called as phytochemicals[2,3]. Recently, it is
clearly known that they have roles in the
protection of human health, when their dietary
intake is significant. More than 4,000
phytochemicals have been cataloged[4] and are
classified by protective function, physical
characteristics and chemical characteristics[5] and
About 150 phytochemicals have been studied in
detail[4].
In wide-ranging dietary phytochemicals are found
in fruits, vegetables, legumes, whole grains, nuts,
seeds, fungi, herbs and spices[3]. Broccoli,
cabbage, carrots, onions, garlic, whole wheat
bread, tomatoes, grapes, cherries, strawberries,
raspberries, beans, legumes, and soy foods are
common sources[6]. Phytochemicals accumulate
in different parts of the plants, such as in the
roots, stems, leaves, flowers, fruits or seeds7.
Many phytochemicals, particularly the pigment
molecules, are often concentrated in the outer
layers of the various plant tissues. Levels vary
from plant to plant depending upon the variety,
processing, cooking and growing conditions[8].
Phytochemicals are also available in
supplementary forms, but evidence is lacking that
they provide the same health benefits as dietary
phytochemicals[4].
These compounds are known as secondary
plant metabolites and have biological properties
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such as antioxidant activity, antimicrobial effect,
modulation of detoxification enzymes,
stimulation of the immune system, decrease of
platelet aggregation and modulation of hormone
metabolism and anticancer property. There are
more than thousand known and many unknown
phytochemicals. It is well-known that plants
produce these chemicals to protect themselves,
but recent researches demonstrate that many
phytochemicals can also protect human against
diseases[9].
Fig.1: Phytochemistry of medicinal plants.
Phytochemicals are not essential nutrients and are
not required by the human body for sustaining
life, but have important properties to prevent or to
fight some common diseases. Many of these
benefits suggest a possible role for
phytochemicals in the prevention and treatment
of disease, Because of this property; many
researchers have been performed to reveal the
beneficial health effects of phytochemicals. The
purpose of the present review is to provide an
overview of the extremely diverse
phytochemicals presents in medicinal plants.
2. The Journey of Medicinal Plant Research
An assessment of the previous trends and impact
of research into the phytochemistry on medicinal
plants of the world is quite desirable before
considering recent trends. After centuries of
empirical use of herbal preparation, the first
isolation of active principles alkaloids such as
morphine, strychnine, quinine etc. in the early
19th century marked a new era in the use of
medicinal plants and the beginning of modern
medicinal plants research. Emphasis shifted away
from plant derived drugs with the tremendous
development of synthetic pharmaceutical
chemistry and microbial fermentation after 1945.
Plant metabolites were mainly investigated from
a phytochemical and chemotaxonomic viewpoint
during this period. Over the last decade, however,
interest in drugs of plant and probably animal
origin has grown steadily[10]. Utilization of
medicinal plants has almost doubled in Western
Europe during that period. Ecological awareness,
the efficacy of a good number of
phytopharmaceutical preparations, such as
ginkgo, garlic or valerian and increased interest
of major pharmaceutical companies in higher
medicinal plants as sources for new lead
structures has been the main reasons for this
renewal of interest. With the development of
chemical science and pharmacognosy physicians
began to extract chemical products from
medicinal plants. A few examples of the products
extracted from medicinal plants are - in 1920,
quinine was isolated from Cinchona by the
French pharmacist, Peletier & Caventou. In the
mid-nineteenth century, a German chemist,
Hoffmann obtained Aspirin from the bark of the
willow. With the active principles in medicinal
plants identified and isolated, plant-based
prescriptions began to be substituted more and
more with pure substances, which were more
powerful and easier to prescribe and administer11.
Phytomedicine almost went into extinction during
the first half of the 21st century due to the use of
the ‘more powerful and potent synthetic drug’.
However, because of the numerous side effects of
these drugs, the value of medicinal plants is being
rediscovered as some of them have proved to be
Journal of Pharmacognosy and Phytochemistry
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as effective as synthetic medicines with fewer or
no side effects and contraindications. It has been
proved that although the effects of natural
remedies may seem slower, the results are
sometimes better on the long run especially in
chronic diseases[12].
3. Biological Activities of Phytochemicals
The phytochemicals present in plants are
responsible for preventing disease and promoting
health have been studied extensively to establish
their efficacy and to understand the underlying
mechanism of their action. Such studies have
included identification and isolation of the
chemical components, establishment of their
biological potency both by in vitro and in vivo
studies in experimental animals and through
epidemiological and clinical-case control studies
in man. Study findings suggest that
phytochemicals may reduce the risk of coronary
heart disease by preventing the oxidation of low-
density lipoprotein (LDL) cholesterol, reducing
the synthesis or absorption of cholesterol,
normalizing blood pressure and clotting, and
improving arterial elasticity[3,13]. Phytochemicals
may detoxify substances that cause cancer. They
appear to neutralize free radicals, inhibit enzymes
that activate carcinogens, and activate enzymes
that detoxify carcinogens. For example,
according to data summarized by Meagher and
Thomson, genistein prevents the formation of
new capillaries that are needed for tumor growth
and metastasis[5]. The physiologic properties of
relatively few phytochemicals are well
understood and more many research has focused
on their possible role in preventing or treating
cancer and heart disease[3]. Phytochemicals have
also been promoted for the prevention and
treatment of diabetes, high blood pressure, and
macular degeneration[4]. While phytochemicals
are classified by function, an individual
compound may have more than one biological
function serving as both an antioxidant and
antibacterial agent13. Bioactive and Disease-
preventing phytochemicals present in plant are
shown in Table 1.
Table 1. Bioactive Phytochemicals In Medicinal Plants.
Classification
Main groups of compounds
Biological function
NSA
(Non-starch poly-
saccharides.)
mucilages, pectins, lignins
Water holding capacity, delay in nutrient
absorption, binding toxins and bile acids
Antibacterial &
Antifungal
Terpenoids, alkaloids, phenolics
Inhibitors of micro
-
organisms, reduce the risk
of fungal infection
Antioxidants
Polyphenolic compounds, flavonoids,
carotenoids, tocopherols, ascorbic acid
Oxygen free radical quenching, inhibition of
lipid peroxidation
Anticancer
Carotenoids, polyphenols, curcumine,
Flavonoids
Inhibitors of tumor, inhibited development of
lung cancer, anti-metastatic activity
Detoxifying
Agents
Reductive acids,
tocopherols, phenols,
indoles, aromatic isothiocyanates, coumarins,
flavones, carotenoids, retinoids, cyanates,
phytosterols
Inhibitors of procarcinogen activation,
inducers of drug binding of carcinogens,
inhibitors of tumourogenesis
Other
Alkaloids,
terpenoids, volatile flavor
compounds, biogenic amines
Neuropharmacological agents, anti
-
oxidants,
cancer chemoprevention
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4. Classification of Phytochemicals
The exact classification of phytochemicals
could have not been performed so far, because
of the wide variety of them. In resent year
Phytochemicals are classified as primary or
secondary constituents, depending on their
role in plant metabolism. Primary constituents
include the common sugars, amino acids,
proteins, purines and pyrimidines of nucleic
acids, chlorophyll’s etc. Secondary constituents
are the remaining plant chemicals such as
alkaloids, terpenes, flavonoids, lignans, plant
steroids, curcumines, saponins, phenolics,
flavonoids and glucosides[14]. Literature
survey indicate that phenolics are the most
numerous and structurally diverse plant
phytocontituents. (Figure 2).
Fig.2: Pie chart representing the major groups of plant
Phytochemicals.
5. Phenolics
Phenolic phytochemicals are the largest category
of phytochemicals and the most widely
distributed in the plant kingdom. The three most
important groups of dietary phenolics are
flavonoids, phenolic acids, and polyphenols.
Phenolic are hydroxyl group (-OH) containing
class of chemical compounds where the (-OH)
bonded directly to an aromatic hydrocarbon
group. Phenol (C6H5OH) is considered the
simplest class of this group of natural
compounds. Phenolic compounds are a large and
complex group of chemical constituents found in
plants[15]. They are plant secondary metabolites,
and they have an important role as defence
compounds. phenolics exhibit several properties
beneficial to humans and its antioxidant
properties are important in determining their role
as protecting agents against free radical-mediated
disease processes. Flavonoids are the largest
group of plant phenols and the most studied[16].
Phenolic acids form a diverse group that includes
the widely distributed hydroxybenzoic and
hydroxycinnamic acids. Phenolic polymers,
commonly known as tannins, are compounds of
high molecular weight that are divided into two
classes: hydrolyzable and condensed tannins.
6. Phenolic acids
The term “phenolic acids”, in general, designates
phenols that possess one carboxylic acid
functional group. Naturally occurring phenolic
acids contain two distinctive carbon frameworks:
the hydroxycinnamic and hydroxybenzoic
structures (Figure3). Hydroxycinnamic acid
compounds are produced as simple esters with
glucose or hydroxy carboxylic acids. Plant
phenolic compounds are different in molecular
structure, and are characterized by hydroxylated
aromatic rings[17]. These compounds have been
studied mainly for their properties against
oxidative damage leading to various degenerative
diseases, such as cardiovascular diseases,
inflammation and cancer. Indeed, tumour cells,
including leukaemia cells, typically have higher
levels of reactive oxygen species (ROS) than
normal cells so that they are particularly sensitive
to oxidative stress[18]. Many papers and reviews
describe studies on bioavailability of phenolic
acids, emphasizing both the direct intake through
food consumption and the indirect bioavailability
deriving by gastric, intestinal and hepatic
metabolism[19].
Phenolics
45%
Alkaloids
18%
Terpenoi
ds &
Steroids
27%
Other
10%
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Table 2: The Major Classes of Phenolic Compounds in Plants
S.N.
Number of carbon atom
Basic skeleton
Class
1.
6
C
6
Simple phenols
Benzoquinones
2.
7
C
6
-
C
1
Phenolic acids
3.
8
C
6
-
C
2
Acetophenones
Tyrosine derivatives
4.
9
C
6
-
C
3
Hydroxycinnamic acid, Coumarins
5.
10
C
6
-
C
4
Naphthoquinones
6.
13
C
6
-
C
1
-
C
6
Xanthones
7.
14
C
6
-
C
2
-
C
6
Stilbenes
8.
15
C
6
-
C
3
-
C
6
Flavonoids
9.
18
(C
6
-
C
3
)
2
Lignans
10.
30
(C
6
-
C
3
-
C
6
)
2
Bioflavonoids
11.
N
(C
6
-
C
3
-
C
6
)
n
Condensed tannins
In addition Phenolic acid compounds and
functions have been the subject of a great number
of agricultural, biological, chemical and medical
studies. In recent years, the importance of
antioxidant activities of phenolic compounds and
their potential usage in processed foods as a
natural antioxidant compounds has reached a new
level and some evidence suggests that the
biological actions of these compounds are related
to their antioxidant activity[20].
5.1 Activity of Phenolic Acids
Phenolic compounds are famous group of
secondary metabolites with wide pharmacological
activities. Phenolic acid compounds and functions
have been the subject of a great number of
agricultural, biological, chemical and medical
studies. Phenolic compounds in many plants are
polymerized into larger molecules such as the
proanthocyanidins (PA; condensed tannins) and
lignins. Moreover, phenolic acids may arise in
food plants as glycosides or esters with other
natural compounds such as sterols, alcohols,
glucosides and hydroxyfatty acids. Varied
biological activities of phenolic acids were
reported. Increases bile secretion, reduces blood
cholesterol and lipid levels and antimicrobial
activity against some strains of bacteria such as
staphylococcus aureus are some of biological
activities of phenolic acids[21]. Phenolics acid
possesses diverse biological activities, for
instance, antiulcer, anti- inflammatory,
antioxidant22, cytotoxic and antitumor,
antispasmodic, and antidepressant activities[23].
6. Flavonoids
Flavonoids are polyphenolic compounds that are
ubiquitous in nature. More than 4,000 flavonoids
have been recognised, many of which occur in
vegetables, fruits and beverages like tea, coffee
and fruit drinks[24]. The flavonoids appear to have
played a major role in successful medical
treatments of ancient times, and their use has
persisted up to now. Flavonoids are ubiquitous
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among vascular plants and occur as aglycones,
glucosides and methylated derivatives. More than
4000 flavonoids have been described so far
within the parts of plants normally consumed by
humans and approximately 650 flavones and
1030 flavanols are known[25]. Small amount of
aglycones (i.e., flavonoids without attached
sugar) are frequently present and occasionally
represent a considerably important proportion of
the total flavonoid compounds in the plant.
Figure 4, represents major flavonoids’ structures.
The six-membered ring condensed with the
benzene ring is either -pyrone (flavones and
flavonols ) or its dihydroderivative (flavanones
and flavan-3-ols ). The position of the benzenoid
substituent divides the flavonoids into two
classes: flavone (2-position) and isoflavone (3-
position). Most flavonoids occur naturally
associated with sugar in conjugated form and,
within any one class, may be characterized as
monoglycosidic, diglycosidic, etc. The glycosidic
linkage is normally located at position 3 or 7 and
the carbohydrate unit can be L-rhamnose, D-
glucose, glucorhamnose, galactose or
arabinose[26].
COOH COOH
O H
COOH
O H
OCH 3
COOH
O H
O H
OH
[1] [2] [3] [4]
COOH COOH
O H
OCH 3
COOH
O H
O H
H3CO
O H
OCH 3
COOH
[5] [6] [7 ] [8]
Hydroxybenzoic acid are Benzoic acid [1], Salicylic acid [2], Vailinilic acid [3], Gallic acid [4] and Hydroxycinnamic aid
are Cinnamic acid [5], Ferulic acid [6], Sinapic acid [7] and Caffeic acid [8].
Fig. 3. Structures of the important naturally occurring phenolic acids.
6.1 Activity of Flavonoids
Flavonoids have gained recent attention because
of their broad biological and pharmacological
activities in these order Flavonoids have been
reported to exert multiple biological property
including antimicrobial, cytotoxicity, anti-
inflammatory as well as antitumor activities but
the best-described property of almost every group
of flavonoids is their capacity to act as powerful
antioxidants which can protect the human body
from free radicals and reactive oxygen species.
The capacity of flavonoids to act as antioxidants
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depends upon their molecular structure. The
position of hydroxyl groups and other features in
the chemical structure of flavonoids are
important for their antioxidant and free radical
scavenging activities. On the other hand
flavonoids such as luteolin and cathechins, are
better antioxidants than the nutrients antioxidants
such as vitamin C, vitamin E and β-carotene.
Flavonoids have been stated to possess many
useful properties, containing anti-inflammatory
activity, enzyme inhibition, antimicrobial
activity, oestrogenic activity, anti-allergic
activity, antioxidant activity, vascular activity and
cytotoxic antitumor activity[27]. Flavonoids
constitute a wide range of substances that play
important role in protecting biological systems
against the harmful effects of oxidative processes
on macromolecules, such as carbohydrates,
proteins, lipids and DNA[28] .
O
O
O
O
O H
O
O
2 -p he ny l- ch r om e n -4 -o ne
F l av o n e s
3- H y d ro x y- 2 -p h e ny l -c h ro m e n-
4- o n e
F lav an ol
2 -p he n yl -ch r om e n -4 -o ne
F la v an o ne
O
O
O H
O
O
O
O H
3 -H y d r o x y- 2 -p h e n yl
c h r o m e n - 4 - o n e
F la v a n o n o l
3 - p h e n y l - c h r o m e n - 4 - o n e
Is o f l av o n e
2 - p h e n y l - c h r o m e n - 3 - o l
F l a v a n - 3 - o l s
O+
OH
3-Hydroxy-2-phenyl chromenylium
Anthocyanidine or Flavylium salt
Fig.4. Chemical structures of some representative flavonoids.
7. Tannin
From a chemical point of view it is difficult to
define tannins since the term encompasses some
very diverse oligomers and polymers[29,30]. It
might be said that the tannins are a heterogeneous
group of high molecular weight polyphenolic
compounds with the capacity to form reversible
and irreversible complexes with proteins
(mainly), polysaccharides (cellulose,
hemicellulose, pectin, etc.), alkaloids, nucleic
acids and minerals, etc[31,32,33]. On the basis of
their structural characteristics it is therefore
possible to divide the tannins into four major
groups: Gallotannins, ellagitannins, complex
tannins, and condensed tannins[34,35,36] (Figure 5).
(1) Gallotannins are all those tannins in which
galloyl units or their meta-depsidic derivatives
are bound to diverse polyol-, catechin-, or
triterpenoid units.
(2) Ellagitannins are those tannins in which at
least two galloyl units are C–C coupled to each
other, and do not contain a glycosidically linked
catechin unit.
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(3) Complex tannins are tannins in which a
catechin unit is bound glycosidically to a
gallotannin or an ellagitannin unit.
(4) Condensed tannins are all oligomeric and
polymeric proanthocyanidins formed by linkage
of C-4 of one catechin with C-8 or C-6 of the
next monomeric catechin.
Tannins are found commonly in fruits such as
grapes, persimmon, blueberry, tea, chocolate,
legume forages, legume trees like Acacia spp.,
Sesbania spp., in grasses i.e; sorghum, corn,
etc[37]. Several health benefits have been
recognized for the intake of tannins and some
epidemiological associations with the decreased
frequency of chronic diseases have been
established[38].
Tannin
Gallotannin Ellagitannin Complex tannin Condense tannin
Fig.5. Classification of tannins.
7.1 Activity of Tannins
In medicine, especially in Asian (Japanese and
Chinese) natural healing, the tannin-containing
plant extracts are used as astringents, against
diarrhoea, as diuretics, against stomach and
duodenal tumours[39], and as antiinflammatory,
antiseptic, antioxidant and haemostatic
pharmaceuticals[40]. Tannins are used in the
dyestuff industry as caustics for cationic dyes
(tannin dyes), and also in the production of inks
(iron gallate ink). In the food industry tannins are
used to clarify wine, beer, and fruit juices. Other
industrial uses of tannins include textile dyes, as
antioxidants in the fruit juice, beer, and wine
industries, and as coagulants in rubber
Production41. Recently the tannins have attracted
scientific interest, especially due to the increased
incidence of deadly illnesses such as AIDS and
various cancers+42]. The search for new lead
compounds for the development of novel
pharmaceuticals has become increasingly
important, especially as the biological action of
tannin-containing plant extracts has been well
documented[43,44].
8. Alkaloids
Alkaloids are natural product that contains
heterocyclic nitrogen atoms, are basic in
character. The name of alkaloids derives from the
“alkaline” and it was used to describe any
nitrogen-containing base[45]. Alkaloids are
naturally synthesis by a large numbers of
organisms, including animals, plants, bacteria and
fungi. Some of the fires natural products to be
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isolated from medicinal plants were alkaloids
when they first obtained from the plants materials
in the early years of 19th century, it was found
that they were nitrogen containing bases which
formed salts with acid. Hence they were known
as the vegetable alkalis or alkaloids and these
alkaloids are used as the local anesthetic and
stimulant as cocaine+46]. Almost all the alkaloids
have a bitter taste. The alkaloid quinine for
example is one of the bitterest tasting substances
known and is significantly bitter (1x10-5) at a
molar concentration[47].
Alkaloids are so numerous and involve such a
variety of molecular structure that their rational
classification is difficult. However, the best
approach to the problem is to group them into
families, depending on the type of heterocyclic
ring system present in the molecule[48]. For
historicxal reasons as also because of their
structural complexities, the nomenclature of
alkaloids has not been systematized. The names
of individual members are, therfour, generally
derived from the name of the plant in which they
occur, or from their characteristic physiological
activity.the various classes of alkaloids according
to the heterocyclic ring system they contain are
listed below.
Pyrrolidine alkaloids: they contain pyrrolidine
( tetrahydropyrrole) ring system. E.g Hygrine found in
Erythroxylum coca leaves.
Pyridine alkaloids: they have piperidine
(hexahydropyridine) ring system. E.g Coniine, piperine
and isopelletierine.
Pyrrolidine-pyridine alkaloids: the heterocyclic ring
system present in there alkaloids is Pyrrolidine-
pyridine.E.g Myosmine, Nicotine alkaloid found in
tobacco (Nicotiana tabacum) plant.
Pyridine-piperidine alkaloids:This family of alkaloids
contains a pyridine ring system join to a piperidine ring
system the simplest member is Anabasine alkaloid
isolated from poisonous Asiatic plant anabasis aphyllan.
Quinoline Alkaloids: These have the basic heterocyclic
ring system quinoline .E.g Quinine occurs in the bark of
cinchona tree.It has been used for centuries for treatment
of malaria.Synthetic drugs such as primaquinine have
largely replace quinine as an anti-malarial.
Isoquinoline alkaloids: They contain heterocyclic rig
system isoquinoline. E.g Opium alkaloids like narcotine,
papaverine, morphine, codeine, and heroine.
N
CH3
CH3
O
N
H
CH3N
HCH3
O
Hygrine [1] Coniine [2] Isopelletierine [3]
N
N
CH 3
N
N
N
N
H
N
CH 3CO
NH
CH3C3H6NH 2
H
Nicotine [4] Mysomine [5] Anabasine [6] Primaquinine [7]
CH CH
OH
N
CH2
CH2
CH CH CH2
CH
3CO
OH
OH
N CH3
O
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Quinine [8] Morphine [9]
Fig. 6. Structures of the important naturally occurring alkaloids.
8.1. Activity of Alkaloids
Alkaloids are significant for the protecting and
survival of plant because they ensure their
survival against micro-organisms (antibacterial
and antifungal activities), insects and
herbivores (feeding deterrens) and also against
other plants by means of allelopathically active
chemicals[49]. The useof alkaloids containing
plants as dyes, spices, drugs or poisons can be
traced back almost to the beginning of
civilization. Alkaloids have many
pharmacological activities including
antihypertensive effects ( many indole
alkaloids), antiarrhythmic effect (quinidine,
spareien), antimalarial activity (quinine),
andanticancer actions (dimeric indoles,
vincristine, vinblastine). These are just a few
example illustrating the great economic
importanceof this group of plant
constituents[50]. Some alkaloids have stimulant
property as caffeine and nicotine, morphine are
used as the analgesic and quinine as the
antimalarial drug[46].
9. Terpenoids
The terpenoids are a class of natural products
which have been derived from five-carbon
isoprene units. Most of the terpenoids have
multi cyclic structures that differ from one
another by their functional groups and basic
carbon skeletons. These types of natural lipids
can be found in every class of living things, and
therefore considered as the largest group of
natural products[51]. Many of the terpenoids are
commercially interesting because of their use as
flavours and fragrances in foods and cosmetics
examples menthol and sclareol or because they
are important for the quality of agricultural
products, such as the flavour of fruits and the
fragrance of flowers like linalool[52]. Terpenes
are widespread in nature, mainly in plants as
constituents of essential oils. Their building
block is the hydrocarbon isoprene,
CH2=C(CH3)-CH=CH2. Terpene hydrocarbons
therefore have molecular formula (C5H8) n and
they are classified according to the number of
isoprene units[53].
9.1 Hemiterpenoids: Consist of a single
isoprene unit. The only hemiterpene is the
Isoprene itself, but oxygen-containing
derivatives of isoprene such as isovaleric acid
and prenol is classify as hemiterpenoids.
9.2 Monoterpenoids: Biochemical
modifications of monoterpenes such as
oxidation or rearrangement produce the related
monoterpenoids. Monoterpenoids have two
isoprene units. Monoterpenes may be of two
types i.e linear (acyclic) or contain rings e.g.
Geranyl pyrophosphate, Eucalyptol, Limonene,
Citral, Camphor and Pinene.
9.3 Sesquiterpenes: Sesquiterpenes have three
isoprene units e.g. Artemisinin, Bisabolol and
Fernesol, oil of flowers, or as cyclic
compounds, such as Eudesmol, found in
Eucalyptus oil.
9.4 Diterpenes: It composed for four isoprene
units. They derive from geranylgeranyl
pyrophosphate. There are some examples of
diterpenes such as cembrene, kahweol,
taxadiene and cafestol. Retinol, retinal, and
phytol are the biologically important
compounds while using diterpenes as the base.
9.5 Triterpenes: It consists of six isoprene
units e.g. Lanosterol and squalene found in
wheat germ, and olives.
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9.6 Tetraterpenoids: It contains eight isoprene
units which may be acyclic like lycopene,
monocyclic like gamma-carotene, and bicyclic
like alpha- and betacarotenes.
CHO
O
α-Pinene [1] Limonine [2] Citral [3] Camphor [4] Abietic acid [5]
CH 2OH
CHO
Vitamin A [6] Retinene [7]
OH
OH
Eudesmol [8] Farnesol [9]
OH
Lanosterol [10] Squalene [11]
β-Carotene [12]
Lycopene [13]
Fig. 7: Structures of the important terpenes of each class.
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Vol. 1 No. 6 2013 www.phytojournal.com Page | 179
9.7 Activity of Terpenes
Among plant secondary metabolites terpenoids
are a structurally most diverse group; they
function as phytoalexins in plant direct defense,
or as signals in indirect defense responses which
involves herbivores and their natural enemies[54].
Many plants produce volatile terpenes in order to
attract specific insects for pollination or otherwise
to expel certain animals using these plants as
food. Less volatile but strongly bitter-tasting or
toxic terpenes also protect some plants from
being eaten by animals (antifeedants)[55]. Last, but
not least, terpenes play an important role as signal
compounds and growth regulators
(phytohormones) of plants, as shown by
preliminary investigations. In addition, terpenoids
can have medicinal properties such as anti-
carcinogenic (e.g. perilla alcohol), antimalarial
(e.g. artemisinin), anti-ulcer, hepaticidal,
antimicrobial or diuretic (e.g. glycyrrhizin)
activity and the sesquiterpenoid antimalarial drug
artimisinin and the diterpenoid anticancer drug
taxol.[53,56].
10. Saponin
Saponins are a group of secondary metabolites
found widely distributed in the plant kingdom
They form a stable foam in aqueous solutions
such as soap, hence the name “saponin”.
Chemically, saponins asa group include
compounds that are glycosylated steroids,
triterpenoids, and steroid alkaloids. Two main
types of steroid aglycones are known, spirostan
and furostan derivatives (Figure 8A,B,
respectively). The main triterpene aglycone is a
derivative of oleanane (Figure 8C)[57]. The
carbohydrate part consists of one
or more sugar moieties containing glucose,
galactose, xylose, arabinose, rhamnose, or
glucuronic acid glycosidically linked to a
sapogenin (aglycone). Saponins that have one
sugar molecule attached at the C-3 position are
called monodesmoside saponins, and those that
have a minimum of two sugars, one attached to
the C-3 and one at C-22, are called bidesmoside
saponins[58].
Fig.8: Basic structure of steroid (A & B) and triterpenoid saponin (C)
10.1 Activity of Saponins
The physiological role of saponins in plants is not
yet fully understood. While there is a number of a
publication describing their identification in
plants, and their multiple effects in animal cells
and on fungi and bacteria, only a few have
addressed their function in plant cells. Many
saponins are known to be antimicrobial, to inhibit
Journal of Pharmacognosy and Phytochemistry
Vol. 1 No. 6 2013 www.phytojournal.com Page | 180
mould, and to protect plants from insect attack.
Saponins may be considered a part of plants’
defence systems, and as such have been included
in a large group of protective molecules found in
plants named phytoanticipins or
phytoprotectants[59]. Saponin mixtures present in
plants and plant products possess diverse
biological effects when present in the animal
body. Extensive research has been carried out
into the membrane-permeabilising,
immunostimulant, hypocholesterolaemic and
anticarcinogenic properties of saponins and they
have also been found to significantly affect
growth, feed intake and reproduction in animals.
These structurally diverse compounds have also
been observed to kill protozoans and molluscs, to
be antioxidants, to impair the digestion of protein
and the uptake of vitamins and minerals in the
gut, to cause hypoglycaemia, and to act as
antifungal and antiviral[60,61,62].
11. Conclusion
Nature is a unique source of structures of high
phytochemical diversity, many of them
possessing interesting biological activities and
medicinal properties. In the context of the
worldwide spread different diseases such as
AIDS, chronic diseases and a variety of cancers,
an intensive search for new lead compounds for
the development of novel pharmacological
therapeutics is extremely important. With the
present information are reported in this review, it
is difficult to establish clear functionality and
structure–activity relationships regarding the
effects of phytochemicals in biological systems
activity. This is largely due to the occurrence of a
vast number of phytochemicals with similar
chemical structures, and to the complexity of
physiological reactions. Moreover, given the
number of phytochemicals isolated so far, nature
must still have many more in store. With the
advances in synthetic methodology and the
development of more sophisticated isolation and
analytical techniques, many more of these
phytochemicals should be identified.
12. Acknowledgement
The authors express gratitude Dr. Shobna Bajpai
maroo, Principal Sarojini Naidu Government
Girls (Post Graduate Autonomous) College and
CMBT Laboratory, Bhopal, for kind support.
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Lignans, ubiquitous constituents of vascular plants, have a number of properties that are of use to humans: some can protect against the onset of various cancers,1 whereas others have antimitotic, antiviral, antibacterial, and antifungal properties.2 Certain lignans can also function, for example, as antioxidants, platelet activating factor receptor antagonists, and anti-tubercular agents, and others are disinfectants, moth repellants, and insecticides.3–5 Because of their important applications from a health and economic perspective, intensified efforts are being expended to both understand and manipulate their biosynthetic pathways. Accordingly, this chapter highlights progress being made towards deciphering the 8–8’ linked lignan metabolic pathway and its utility to the bioengineering of human foodstuffs.
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The digestive enzymes alkaline phosphatase and 5'-nucleotide phosphodiesterase, solubilized from bovine intestinal mucosa and purified to homogeneity, were found to be strongly inhibited in vitro by condensed tannins (proanthocyanidins) purified from sorghum seeds and from quebracho. Tannin inhibition was prevented and reversed by the detergent Triton X-100 (protein-binding agent), by soluble polyvinylpyrrolidone (tannin-binding agent), or by phosphatidylcholine (membrane component). When tested as a crude particulate membrane fraction more characteristic of their in vivo condition, both enzymes were inhibited much less than either purified enzyme at the same tannin concentration. Because the enzymes appear to be relatively insensitive to inhibition by tannin in conditions which mimic in vivo conditions, and because the proportion of the dietary tannin which is available to interact with these enzymes in the digestive tract is likely to be rather small, we suggest that the antinutritional effects and ecological significance of dietary tannins are not due to tannin inhibition of these or other digestive enzymes by direct binding to them.
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Characteristics of higher plant terpenoids that result in mediation of numerous kinds of ecological interactions are discussed as a framework for this Symposium on Chemical Ecology of Terpenoids. However, the role of terpenoid mixtures, either constitutive or induced, their intraspecific qualitative and quantitative compositional variation, and their dosage-dependent effects are emphasized in subsequent discussions. It is suggested that little previous attention to these characteristics may have contributed to terpenoids having been misrepresented in some chemical defense theories. Selected phytocentric examples of terpenoid interactions are presented: (1) defense against generalist and specialist insect and mammalian herbivores, (2) defense against insect-vectored fungi and potentially pathogenic endophytic fungi, (3) attraction of entomophages and pollinators, (4) allelopathic effects that inhibit seed germination and soil bacteria, and (5) interaction with reactive troposphere gases. The results are integrated by discussing how these terpenoids may be contributing factors in determining some properties of terrestrial plant communities and ecosystems. A terrestrial phytocentric approach is necessitated due to the magnitude and scope of terpenoid interactions. This presentation has a more broadly based ecological perspective than the several excellent recent reviews of the ecological chemistry of terpenoids.
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Plant saponins are a group of naturally occuring triterpene or steroid glycosides which include a large number of biologically and pharmacologically active compounds. Saponins have been shown in both in vitroand in vivoexperimental test systems during the last decade to possess a broad spectrum of biological and pharmacological activities. This review will summarize some of the recent advances concerning cancer-related activity, immunostimulating, immunoadjuvant, antihepatotoxic, antiphlogistic, antiallergic, molluscicidal, hemolytic, antifungal, antiviral, and hypoglycemic activities. In addition, the effects on the cardiovascular system and the central nervous system will be discussed together with other miscellaneous effects. Studies of structure/activity relationships and mechanism of action will be presented.