<<

ISSN 2278- 4136

ZDB-Number: 2668735-5

IC Journal No: 8192 Volume 1 Issue 6

Online Available at www.phytojournal.com

Journal of and

Phytochemistry of Medicinal

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: [email protected]] 2. Center for & Bio-Technology Research and Training, Bhopal, India

Medicinal plants are a rich source of bioactive 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 for these phytochemicals and assessing their potential in protecting against different types of diseases Keyword: Phytochemicals, , , , Saponins, and Phenolics.

1. Introduction In wide-ranging dietary phytochemicals are found Phytochemicals (from the Greek word phyto, in , vegetables, legumes, whole grains, nuts, meaning ) are biologically active, naturally , fungi, herbs and spices[3]. Broccoli, occurring chemical compounds found in plants, cabbage, carrots, onions, garlic, whole wheat which provide health benefits for humans further bread, tomatoes, grapes, cherries, strawberries, than those attributed to macronutrients and raspberries, beans, legumes, and soy foods are micronutrients[1]. They protect plants from common sources[6]. Phytochemicals accumulate disease and damage and contribute to the plant’s in different parts of the plants, such as in the color, aroma and flavor. In general, the plant , stems, , , fruits or seeds7. chemicals that protect plant cells from Many phytochemicals, particularly the pigment environmental hazards such as pollution, stress, , are often concentrated in the outer drought, UV exposure and pathogenic attack are layers of the various plant tissues. Levels vary called as phytochemicals[2,3]. Recently, it is from plant to plant depending upon the variety, clearly known that they have roles in the processing, cooking and growing conditions[8]. protection of human health, when their dietary Phytochemicals are also available in intake is significant. More than 4,000 supplementary forms, but evidence is lacking that phytochemicals have been cataloged[4] and are they provide the same health benefits as dietary classified by protective function, physical phytochemicals[4]. characteristics and chemical characteristics[5] and About 150 phytochemicals have been studied in These compounds are known as secondary detail[4]. plant metabolites and have biological properties

Vol. 1 No. 6 2013 www.phytojournal.com Page | 168 Journal of Pharmacognosy and Phytochemistry

such as antioxidant activity, antimicrobial effect, modulation of detoxification , 2. The Journey of Medicinal Plant Research stimulation of the immune system, decrease of An assessment of the previous trends and impact platelet aggregation and modulation of hormone of research into the phytochemistry on medicinal and anticancer property. There are plants of the world is quite desirable before more than thousand known and many unknown considering recent trends. After centuries of phytochemicals. It is well-known that plants empirical use of herbal preparation, the first produce these chemicals to protect themselves, isolation of active principles alkaloids such as but recent researches demonstrate that many , strychnine, etc. in the early phytochemicals can also protect human against 19th century marked a new era in the use of diseases[9]. medicinal plants and the beginning of modern medicinal plants research. Emphasis shifted away from plant derived with the tremendous development of synthetic pharmaceutical and microbial fermentation after 1945. Plant metabolites were mainly investigated from a 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 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 by the Fig.1: Phytochemistry of medicinal plants. French , Peletier & Caventou. In the mid-nineteenth century, a German , Phytochemicals are not essential nutrients and are Hoffmann obtained Aspirin from the bark of the not required by the human body for sustaining willow. With the active principles in medicinal life, but have important properties to prevent or to plants identified and isolated, plant-based fight some common diseases. Many of these prescriptions began to be substituted more and benefits suggest a possible role for more with pure substances, which were more phytochemicals in the prevention and treatment powerful and easier to prescribe and administer11. of disease, Because of this property; many Phytomedicine almost went into extinction during researchers have been performed to reveal the the first half of the 21st century due to the use of beneficial health effects of phytochemicals. The the ‘more powerful and potent synthetic ’. purpose of the present review is to provide an However, because of the numerous side effects of overview of the extremely diverse these drugs, the value of medicinal plants is being phytochemicals presents in medicinal plants. rediscovered as some of them have proved to be

Vol. 1 No. 6 2013 www.phytojournal.com Page | 169

Journal of Pharmacognosy and Phytochemistry

as effective as synthetic with fewer or normalizing blood pressure and clotting, and no side effects and contraindications. It has been improving arterial elasticity[3,13]. Phytochemicals proved that although the effects of natural may detoxify substances that cause cancer. They remedies may seem slower, the results are appear to neutralize free radicals, inhibit enzymes sometimes better on the long run especially in that activate carcinogens, and activate enzymes chronic diseases[12]. that detoxify carcinogens. For example, according to data summarized by Meagher and 3. Biological Activities of Phytochemicals Thomson, prevents the formation of The phytochemicals present in plants are new capillaries that are needed for tumor growth responsible for preventing disease and promoting and metastasis[5]. The physiologic properties of health have been studied extensively to establish relatively few phytochemicals are well their efficacy and to understand the underlying understood and more many research has focused mechanism of their action. Such studies have on their possible role in preventing or treating included identification and isolation of the cancer and heart disease[3]. Phytochemicals have chemical components, establishment of their also been promoted for the prevention and biological potency both by in vitro and in vivo treatment of diabetes, high blood pressure, and studies in experimental animals and through macular degeneration[4]. While phytochemicals epidemiological and clinical-case control studies are classified by function, an individual in man. Study findings suggest that compound may have more than one biological phytochemicals may reduce the risk of coronary function serving as both an antioxidant and heart disease by preventing the oxidation of low- antibacterial agent13. Bioactive and Disease- density lipoprotein (LDL) cholesterol, reducing preventing phytochemicals present in plant are the synthesis or absorption of cholesterol, shown in Table 1.

Table 1. Bioactive Phytochemicals In Medicinal Plants.

Classification Main groups of compounds Biological function

NSA , hemicellulose, gums, Water holding capacity, delay in nutrient (Non- poly- mucilages, pectins, lignins absorption, binding toxins and bile acids saccharides.) Antibacterial & Terpenoids, alkaloids, phenolics Inhibitors of micro-organisms, reduce the risk of fungal infection

Antioxidants Polyphenolic compounds, flavonoids, free radical quenching, inhibition of , tocopherols, ascorbic acid lipid peroxidation

Anticancer Carotenoids, , curcumine, Inhibitors of tumor, inhibited development of Flavonoids lung cancer, anti-metastatic activity Detoxifying Reductive acids, tocopherols, phenols, Inhibitors of procarcinogen activation, Agents indoles, aromatic isothiocyanates, coumarins, inducers of drug binding of carcinogens, flavones, carotenoids, retinoids, cyanates, inhibitors of tumourogenesis phytosterols

Other Alkaloids, terpenoids, volatile flavor Neuropharmacological agents, anti- oxidants, compounds, biogenic amines cancer chemoprevention

Vol. 1 No. 6 2013 www.phytojournal.com Page | 170

Journal of Pharmacognosy and Phytochemistry

4. Classification of Phytochemicals class of chemical compounds where the (-OH) The exact classification of phytochemicals bonded directly to an aromatic hydrocarbon could have not been performed so far, because group. Phenol (C6H5OH) is considered the of the wide variety of them. In resent year simplest class of this group of natural Phytochemicals are classified as primary or compounds. Phenolic compounds are a large and secondary constituents, depending on their complex group of chemical constituents found in [15] role in plant metabolism. Primary constituents plants . They are plant secondary metabolites, include the common , amino acids, and they have an important role as defence , purines and pyrimidines of nucleic compounds. phenolics exhibit several properties acids, ’s etc. Secondary constituents beneficial to humans and its antioxidant are the remaining plant chemicals such as properties are important in determining their role alkaloids, , flavonoids, , plant as protecting agents against free radical-mediated disease processes. Flavonoids are the largest , curcumines, saponins, phenolics, [16] flavonoids and glucosides[14]. Literature group of plant phenols and the most studied . survey indicate that phenolics are the most Phenolic acids form a diverse group that includes numerous and structurally diverse plant the widely distributed hydroxybenzoic and phytocontituents. (Figure 2). 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 Other phenols that possess one carboxylic acid 10% functional group. Naturally occurring phenolic acids contain two distinctive carbon frameworks: the hydroxycinnamic and hydroxybenzoic Terpenoi Phenolics structures (Figure3). Hydroxycinnamic acid ds & 45% compounds are produced as simple esters with Steroids glucose or hydroxy carboxylic acids. Plant 27% phenolic compounds are different in molecular , and are characterized by hydroxylated [17] Alkaloids aromatic rings . These compounds have been 18% studied mainly for their properties against oxidative damage leading to various degenerative diseases, such as cardiovascular diseases, inflammation and cancer. Indeed, tumour cells, Fig.2: Pie chart representing the major groups of plant including leukaemia cells, typically have higher Phytochemicals. levels of reactive oxygen species (ROS) than normal cells so that they are particularly sensitive [18] to oxidative stress . Many papers and reviews 5. Phenolics describe studies on bioavailability of phenolic Phenolic phytochemicals are the largest category acids, emphasizing both the direct intake through of phytochemicals and the most widely food consumption and the indirect bioavailability distributed in the plant kingdom. The three most deriving by gastric, intestinal and hepatic [19] important groups of dietary phenolics are metabolism . flavonoids, phenolic acids, and polyphenols. Phenolic are hydroxyl group (-OH) containing

Vol. 1 No. 6 2013 www.phytojournal.com Page | 171

Journal of Pharmacognosy and Phytochemistry

Table 2: The Major Classes of Phenolic Compounds in Plants

S.N. Number of carbon Basic skeleton Class 1. 6 C6 Simple phenols Benzoquinones

2. 7 C6-C1 Phenolic acids

3. 8 C6-C2 Acetophenones Tyrosine derivatives

4. 9 C6-C3 Hydroxycinnamic acid, Coumarins

5. 10 C6-C4 Naphthoquinones

6. 13 C6- C1-C6 Xanthones

7. 14 C6- C2-C6 Stilbenes

8. 15 C6- C3-C6 Flavonoids

9. 18 (C6- C3)2 Lignans

10. 30 (C6- C3-C6 ) 2 Bioflavonoids

11. N (C6- C3-C6)n Condensed tannins

In addition Phenolic acid compounds and natural compounds such as sterols, alcohols, functions have been the subject of a great number glucosides and hydroxyfatty acids. Varied of agricultural, biological, chemical and medical biological activities of phenolic acids were studies. In recent years, the importance of reported. Increases bile secretion, reduces blood antioxidant activities of phenolic compounds and cholesterol and lipid levels and antimicrobial their potential usage in processed foods as a activity against some strains of bacteria such as natural antioxidant compounds has reached a new staphylococcus aureus are some of biological level and some evidence suggests that the activities of phenolic acids[21]. Phenolics acid biological actions of these compounds are related possesses diverse biological activities, for to their antioxidant activity[20]. instance, antiulcer, anti- inflammatory, antioxidant22, cytotoxic and antitumor, 5.1 Activity of Phenolic Acids antispasmodic, and antidepressant activities[23]. Phenolic compounds are famous group of secondary metabolites with wide pharmacological 6. Flavonoids activities. Phenolic acid compounds and functions Flavonoids are polyphenolic compounds that are have been the subject of a great number of ubiquitous in nature. More than 4,000 flavonoids agricultural, biological, chemical and medical have been recognised, many of which occur in studies. Phenolic compounds in many plants are vegetables, fruits and beverages like tea, coffee polymerized into larger molecules such as the and drinks[24]. The flavonoids appear to have proanthocyanidins (PA; condensed tannins) and played a major role in successful medical lignins. Moreover, phenolic acids may arise in treatments of ancient times, and their use has food plants as or esters with other persisted up to now. Flavonoids are ubiquitous

Vol. 1 No. 6 2013 www.phytojournal.com Page | 172

Journal of Pharmacognosy and Phytochemistry

among vascular plants and occur as aglycones, flavonols ) or its dihydroderivative (flavanones glucosides and methylated derivatives. More than and flavan-3-ols ). The position of the benzenoid 4000 flavonoids have been described so far substituent divides the flavonoids into two within the parts of plants normally consumed by classes: flavone (2-position) and (3- humans and approximately 650 flavones and position). Most flavonoids occur naturally 1030 flavanols are known[25]. Small amount of associated with in conjugated form and, aglycones (i.e., flavonoids without attached within any one class, may be characterized as sugar) are frequently present and occasionally monoglycosidic, diglycosidic, etc. The glycosidic represent a considerably important proportion of linkage is normally located at position 3 or 7 and the total compounds in the plant. the carbohydrate unit can be L-rhamnose, D- Figure 4, represents major flavonoids’ structures. glucose, glucorhamnose, galactose or The six-membered ring condensed with the arabinose[26]. benzene ring is either -pyrone (flavones and

COOH COOH COOH COOH O H

H O O H OCH 3 O H O H

[1] [2] [3] [4]

COOH COOH COOH COOH

H 3 CO OCH 3 OCH 3 O H O H O H O H

[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 inflammatory as well as antitumor activities but Flavonoids have gained recent attention because the best-described property of almost every group of their broad biological and pharmacological of flavonoids is their capacity to act as powerful activities in these order Flavonoids have been antioxidants which can protect the human body reported to exert multiple biological property from free radicals and reactive oxygen species. including antimicrobial, cytotoxicity, anti- The capacity of flavonoids to act as antioxidants

Vol. 1 No. 6 2013 www.phytojournal.com Page | 173

Journal of Pharmacognosy and Phytochemistry

depends upon their molecular structure. The activity, inhibition, antimicrobial position of hydroxyl groups and other features in activity, oestrogenic activity, anti-allergic the of flavonoids are activity, antioxidant activity, vascular activity and important for their antioxidant and free radical cytotoxic antitumor activity[27]. Flavonoids scavenging activities. On the other hand constitute a wide range of substances that play flavonoids such as luteolin and cathechins, are important role in protecting biological systems better antioxidants than the nutrients antioxidants against the harmful effects of oxidative processes such as vitamin C, vitamin E and β-carotene. on macromolecules, such as carbohydrates, Flavonoids have been stated to possess many proteins, lipids and DNA[28] . useful properties, containing anti-inflammatory

O O O

O H O O O 2-phenyl-chromen-4-one 3-Hydroxy-2-phenyl-chromen- 2-phenyl-chromen-4-one Flavones 4-one Flavanol Flavanone

O O O

O H O H O O

3-Hydroxy-2-phenyl 3-phenyl-chromen-4-one 2-phenyl-chromen-3-ol chromen-4-one Is o f la v o n e Flavan-3-ols F la v a n o n o l

+ O 3-Hydroxy-2-phenyl chromenylium Anthocyanidine or Flavylium salt OH Fig.4. Chemical structures of some representative flavonoids.

7. groups: Gallotannins, ellagitannins, complex From a chemical point of view it is difficult to tannins, and condensed tannins[34,35,36] (Figure 5). define tannins since the term encompasses some very diverse oligomers and polymers[29,30]. It (1) Gallotannins are all those tannins in which might be said that the tannins are a heterogeneous galloyl units or their meta-depsidic derivatives group of high molecular weight polyphenolic are bound to diverse polyol-, catechin-, or compounds with the capacity to form reversible triterpenoid units. and irreversible complexes with proteins (2) Ellagitannins are those tannins in which at (mainly), polysaccharides (cellulose, least two galloyl units are C–C coupled to each hemicellulose, pectin, etc.), alkaloids, nucleic other, and do not contain a glycosidically linked acids and minerals, etc[31,32,33]. On the basis of catechin unit. their structural characteristics it is therefore possible to divide the tannins into four major

Vol. 1 No. 6 2013 www.phytojournal.com Page | 174

Journal of Pharmacognosy and Phytochemistry

(3) Complex tannins are tannins in which a legume forages, legume like Acacia spp., catechin unit is bound glycosidically to a Sesbania spp., in grasses i.e; sorghum, corn, gallotannin or an ellagitannin unit. etc[37]. Several health benefits have been (4) Condensed tannins are all oligomeric and recognized for the intake of tannins and some polymeric proanthocyanidins formed by linkage epidemiological associations with the decreased of C-4 of one catechin with C-8 or C-6 of the frequency of chronic diseases have been next monomeric catechin. established[38]. Tannins are found commonly in fruits such as grapes, persimmon, blueberry, tea, chocolate,

Tannin

Gallotannin Ellagitannin Complex tannin Condense tannin

Fig.5. Classification of tannins.

7.1 Activity of Tannins incidence of deadly illnesses such as AIDS and In , especially in Asian (Japanese and various cancers+42]. The search for new lead Chinese) natural healing, the tannin-containing compounds for the development of novel plant extracts are used as astringents, against pharmaceuticals has become increasingly diarrhoea, as , against stomach and important, especially as the biological action of duodenal tumours[39], and as antiinflammatory, tannin-containing plant extracts has been well , antioxidant and haemostatic documented[43,44]. pharmaceuticals[40]. Tannins are used in the dyestuff industry as caustics for cationic dyes 8. Alkaloids (tannin dyes), and also in the production of inks Alkaloids are that contains (iron gallate ink). In the food industry tannins are heterocyclic , are basic in used to clarify wine, beer, and fruit juices. Other character. The name of alkaloids derives from the industrial uses of tannins include textile dyes, as “alkaline” and it was used to describe any antioxidants in the fruit juice, beer, and wine nitrogen-containing base[45]. Alkaloids are industries, and as coagulants in rubber naturally synthesis by a large numbers of Production41. Recently the tannins have attracted organisms, including animals, plants, bacteria and scientific interest, especially due to the increased fungi. Some of the fires natural products to be

Vol. 1 No. 6 2013 www.phytojournal.com Page | 175

Journal of Pharmacognosy and Phytochemistry

isolated from medicinal plants were alkaloids to the heterocyclic ring system they contain are when they first obtained from the plants materials listed below. in the early years of 19th century, it was found that they were nitrogen containing bases which Pyrrolidine alkaloids: they contain pyrrolidine formed salts with acid. Hence they were known ( tetrahydropyrrole) ring system. E.g Hygrine found in Erythroxylum leaves. as the vegetable alkalis or alkaloids and these alkaloids are used as the local anesthetic and Pyridine alkaloids: they have piperidine 46] stimulant as + . Almost all the alkaloids (hexahydropyridine) ring system. E.g Coniine, piperine have a bitter taste. The quinine for and isopelletierine. example is one of the bitterest tasting substances known and is significantly bitter (1x10-5) at a Pyrrolidine-pyridine alkaloids: the heterocyclic ring molar concentration[47]. system present in there alkaloids is Pyrrolidine- pyridine.E.g Myosmine, alkaloid found in Alkaloids are so numerous and involve such a (Nicotiana tabacum) plant. variety of molecular structure that their rational classification is difficult. However, the best Pyridine-piperidine alkaloids:This family of alkaloids approach to the problem is to group them into contains a pyridine ring system join to a piperidine ring families, depending on the type of heterocyclic system the simplest member is Anabasine alkaloid ring system present in the [48]. For isolated from poisonous Asiatic plant anabasis aphyllan. historicxal reasons as also because of their Quinoline Alkaloids: These have the basic heterocyclic structural complexities, the nomenclature of ring system quinoline .E.g Quinine occurs in the bark of alkaloids has not been systematized. The names cinchona .It has been used for centuries for treatment of individual members are, therfour, generally of malaria.Synthetic drugs such as primaquinine have derived from the name of the plant in which they largely replace quinine as an anti-malarial. occur, or from their characteristic physiological activity.the various classes of alkaloids according Isoquinoline alkaloids: They contain heterocyclic rig system isoquinoline. E.g Opium alkaloids like narcotine, papaverine, morphine, , and heroine.

O O

N C H 3 N C H 3 N C H C H 3 H H 3 Hygrine [1] Coniine [2] Isopelletierine [3]

CH 3CO

N

NH N N N H H C C H NH N N 3 3 6 2 N H 3 C H

Nicotine [4] Mysomine [5] Anabasine [6] Primaquinine [7]

CH CH CH2 CH2 HO H O CH HC CH2

CH3CO N O

N C H 3 H O

Vol. 1 No. 6 2013 www.phytojournal.com Page | 176

Journal of Pharmacognosy and Phytochemistry

Quinine [8] Morphine [9] Fig. 6. Structures of the important naturally occurring alkaloids.

8.1. Activity of Alkaloids are widespread in nature, mainly in plants as Alkaloids are significant for the protecting and constituents of essential oils. Their building survival of plant because they ensure their block is the hydrocarbon isoprene, survival against micro-organisms (antibacterial CH2=C(CH3)-CH=CH2. hydrocarbons and antifungal activities), and therefore have molecular formula (C5H8) n and herbivores (feeding deterrens) and also against they are classified according to the number of other plants by means of allelopathically active isoprene units[53]. chemicals[49]. The useof alkaloids containing plants as dyes, spices, drugs or poisons can be 9.1 Hemiterpenoids: Consist of a single traced back almost to the beginning of isoprene unit. The only hemiterpene is the civilization. Alkaloids have many Isoprene itself, but oxygen-containing pharmacological activities including derivatives of isoprene such as isovaleric acid antihypertensive effects ( many indole and prenol is classify as hemiterpenoids. alkaloids), antiarrhythmic effect (, spareien), antimalarial activity (quinine), 9.2 Monoterpenoids: Biochemical andanticancer actions (dimeric indoles, modifications of such as vincristine, vinblastine). These are just a few oxidation or rearrangement produce the related example illustrating the great economic monoterpenoids. Monoterpenoids have two importanceof this group of plant isoprene units. Monoterpenes may be of two constituents[50]. Some alkaloids have stimulant types i.e linear (acyclic) or contain rings e.g. property as and nicotine, morphine are Geranyl pyrophosphate, Eucalyptol, Limonene, used as the analgesic and quinine as the Citral, Camphor and Pinene. antimalarial drug[46]. 9.3 Sesquiterpenes: Sesquiterpenes have three 9. Terpenoids isoprene units e.g. Artemisinin, Bisabolol and The terpenoids are a class of natural products Fernesol, oil of flowers, or as cyclic which have been derived from five-carbon compounds, such as Eudesmol, found in isoprene units. Most of the terpenoids have Eucalyptus oil. multi cyclic structures that differ from one another by their functional groups and basic 9.4 Diterpenes: It composed for four isoprene carbon skeletons. These types of natural lipids units. They derive from geranylgeranyl can be found in every class of living things, and pyrophosphate. There are some examples of therefore considered as the largest group of diterpenes such as cembrene, kahweol, natural products[51]. Many of the terpenoids are taxadiene and cafestol. Retinol, retinal, and commercially interesting because of their use as phytol are the biologically important flavours and fragrances in foods and cosmetics compounds while using diterpenes as the base. examples menthol and sclareol or because they are important for the quality of agricultural 9.5 Triterpenes: It consists of six isoprene products, such as the flavour of fruits and the units e.g. Lanosterol and squalene found in fragrance of flowers like linalool[52]. Terpenes wheat germ, and olives.

Vol. 1 No. 6 2013 www.phytojournal.com Page | 177

Journal of Pharmacognosy and Phytochemistry

9.6 Tetraterpenoids: It contains eight isoprene units which may be acyclic like lycopene, monocyclic like gamma-carotene, and bicyclic like alpha- and betacarotenes.

O

CHO

α-Pinene [1] Limonine [2] Citral [3] Camphor [4] Abietic acid [5]

CH 2 OH CHO

Vitamin A [6] Retinene [7]

OH

OH Eudesmol [8] Farnesol [9]

HO

Lanosterol [10] Squalene [11]

β-Carotene [12]

Lycopene [13]

Fig. 7: Structures of the important terpenes of each class.

Vol. 1 No. 6 2013 www.phytojournal.com Page | 178

Journal of Pharmacognosy and Phytochemistry

9.7 Activity of Terpenes Among plant secondary metabolites terpenoids 10. Saponin are a structurally most diverse group; they Saponins are a group of secondary metabolites function as phytoalexins in plant direct defense, found widely distributed in the plant kingdom or as signals in indirect defense responses which They form a stable foam in aqueous solutions involves herbivores and their natural enemies[54]. such as soap, hence the name “saponin”. Many plants produce volatile terpenes in order to Chemically, saponins asa group include attract specific insects for or otherwise compounds that are glycosylated steroids, to expel certain animals using these plants as triterpenoids, and alkaloids. Two main food. Less volatile but strongly bitter-tasting or types of steroid aglycones are known, spirostan toxic terpenes also protect some plants from and furostan derivatives (Figure 8A,B, being eaten by animals (antifeedants)[55]. Last, but respectively). The main triterpene aglycone is a not least, terpenes play an important role as signal derivative of oleanane (Figure 8C)[57]. The compounds and growth regulators carbohydrate part consists of one (phytohormones) of plants, as shown by or more sugar moieties containing glucose, preliminary investigations. In addition, terpenoids galactose, xylose, arabinose, rhamnose, or can have medicinal properties such as anti- glucuronic acid glycosidically linked to a carcinogenic (e.g. perilla alcohol), antimalarial sapogenin (aglycone). Saponins that have one (e.g. artemisinin), anti-ulcer, hepaticidal, sugar molecule attached at the C-3 position are antimicrobial or (e.g. glycyrrhizin) called monodesmoside saponins, and those that activity and the sesquiterpenoid antimalarial drug have a minimum of two sugars, one attached to artimisinin and the diterpenoid anticancer drug the C-3 and one at C-22, are called bidesmoside taxol.[53,56]. saponins[58].

Fig.8: Basic structure of steroid (A & B) and triterpenoid saponin (C)

10.1 Activity of Saponins plants, and their multiple effects in animal cells The physiological role of saponins in plants is not and on fungi and bacteria, only a few have yet fully understood. While there is a number of a addressed their function in plant cells. Many publication describing their identification in saponins are known to be antimicrobial, to inhibit

Vol. 1 No. 6 2013 www.phytojournal.com Page | 179

Journal of Pharmacognosy and Phytochemistry

mould, and to protect plants from attack. 12. Acknowledgement Saponins may be considered a part of plants’ The authors express gratitude Dr. Shobna Bajpai defence systems, and as such have been included maroo, Principal Sarojini Naidu Government in a large group of protective molecules found in Girls (Post Graduate Autonomous) College and plants named phytoanticipins or CMBT Laboratory, Bhopal, for kind support. phytoprotectants[59]. Saponin mixtures present in plants and plant products possess diverse 13. References biological effects when present in the animal 1. Hasler CM, Blumberg JB. Symposium on body. Extensive research has been carried out Phytochemicals: and . Journal of Nutrition 1999; 129: 756S-757S. into the membrane-permeabilising, 2. Gibson EL, Wardel J, Watts CJ. Fruit and immunostimulant, hypocholesterolaemic and Vegetable Consumption, Nutritional Knowledge anticarcinogenic properties of saponins and they and Beliefs in Mothers and Children. Appetite have also been found to significantly affect 1998; 31: 205-228. growth, feed intake and reproduction in animals. 3. Mathai K. Nutrition in the Adult Years. In Krause’s Food, Nutrition, and Diet Therapy, 10th These structurally diverse compounds have also ed., ed. L.K. Mahan and S. Escott-Stump, 2000; been observed to kill protozoans and molluscs, to 271: 274-275. be antioxidants, to impair the digestion of 4. American Cancer Society. Phytochemicals. and the uptake of vitamins and minerals in the Available at gut, to cause hypoglycaemia, and to act as http://www.cancer.org/eprise/main/docroot/ETO/c [60,61,62] ontent/ETO_5_3X_Phytochemicals, June 2000. antifungal and antiviral . 5. Meagher E, Thomson C. Vitamin and Mineral Therapy. In Medical Nutrition and Disease, 2nd 11. Conclusion ed., G Morrison and L Hark, Malden, Nature is a unique source of structures of high Massachusetts: Blackwell Science Inc, 1999; 33- phytochemical diversity, many of them 58. 6. Moorachian ME. Phytochemicals: Why and How? possessing interesting biological activities and Tastings, 2000; 4-5. medicinal properties. In the context of the 7. Costa MA, Zia ZQ, Davin LB, Lewis NG. Chapter worldwide spread different diseases such as Four: Toward Engineering the Metabolic AIDS, chronic diseases and a variety of cancers, Pathways of Cancer-Preventing Lignans in Cereal an intensive search for new lead compounds for Grains and Other Crops. In Recent Advances in Phytochemistry, vol. 33, Phytochemicals in the development of novel pharmacological Human Health Protection, Nutrition, and Plant therapeutics is extremely important. With the Defense, ed. JT Romeo, New York, 1999; 67-87. present information are reported in this review, it 8. King A, Young G. Characteristics and Occurrence is difficult to establish clear functionality and of Phenolic Phytochemicals. Journal of the structure–activity relationships regarding the American Dietetic Association, 1999; 24: 213-218. 9. Narasinga Rao. Bioactive phytochemicals in effects of phytochemicals in biological systems Indian foods and their potential in health activity. This is largely due to the occurrence of a promotion and disease prevention. Asia Pacific vast number of phytochemicals with similar Journal of Clinical Nutrition, 2003: 12 (1): 9-22 chemical structures, and to the complexity of 10. Hamburger M, Hostettmann K. Bioactivity in physiological reactions. Moreover, given the Plants: The Link between Phytochemistry and Medicine. Phytochemistry, 1991; 30: 3864-3874. number of phytochemicals isolated so far, nature 11. Harvey A. Strategy for discovering drugs from must still have many more in store. With the previously unexploited natural products. Drug advances in synthetic methodology and the Discovery Today, 2000; 5: 294-300. development of more sophisticated isolation and 12. Akunyili DN. The role of regulation of medicinal analytical techniques, many more of these plants and phytomedicine in socio-economic development, AGM/SC of the Nigerian Society of phytochemicals should be identified. Pharmacognosy. 13. Abuja, 2003; 1-7. 14. Hahn NI. Is Nature’s Cure for What Ails Us? A Look at the Research. Journal of

Vol. 1 No. 6 2013 www.phytojournal.com Page | 180

Journal of Pharmacognosy and Phytochemistry

the American Dietetic Association, 1998; 98: 974- overview. Methods Enzyme molecule, 1990; 186: 976. 1-85 15. Walton NJ, Mayer MJ, Narbad A. Molecules of 30. Harborne JB. An overview of antinutritional Interest: Vanillin. Phytochemistry, 2003; 63: 505- factors in higher plants. In: Secondary plants 515. products. Antinutritional and beneficial actions in 16. Dai J, Mumper R. Plant phenolics: extraction, animal feeding Caygill JC and Mueller-Harvey I, analysis and their antioxidant and anticancer eds. Nottingham Univ Press, UK, 1999; 7-16. properties. Molecules, 2010; 15: 7313-7352. 31. Schofield P, Mbugua DM, Pell AN. Analysis of 17. Balasundram N, Sundram K, Saman S. Phenolic condensed tannins: a review. Animal Feed Science Compounds in Plants and Agriindustrial by- Technology, 2001; 91: 21-40. Products: Antioxidant Activity, Occurrence, and 32. Vansoest PJ. Nutritional ecology of the ruminant, Potential Uses. , 2006; 99: 191- 2nd ed. Cornell Univ Press. Ithaca, NY, 1994; 476. 203. 33. Mueller-harvey I, Mcallan AB. Tannins: Their 18. Mandal SM, Chakraborty D, Dey S. Phenolic biochemistry and nutritional properties. Advances acids act as signaling molecules in plant–microbe in biochemistry and , Vol. symbioses. Plant Signal Behav, 2010; 5: 359-368. 1 Morrison IM ed. JAI Press Ltd, London (UK), 19. Battisti V, Maders LD, Bagatini MD, Santos KF, 1992; 151-217. Spanevello RM, Maldonado PA, Brulé AO, 34. Mangan JL. Nutritional effects of tannins in Araújo Mdo C, Schetinger MR, Morsch VM. animal feeds. Nutrition Research and Reviews, Measurement of oxidative stress and antioxidant 1988; 1: 209-231. status in acute lymphoblastic leukemia patients. 35. Mc-Leod MN. Plant tannins: Their role in forage Clin Biochem, 2008; 41: 511-518. quality. Nutrition Abstract Review, 1974; 44: 803- 20. Lafay S and Gil-Izquierdo A. Bioavailability of 812. phenolic acids. Phytochemical Reviews, 2008; 7: 36. Mole S, Waterman PG. Tannic acid and 301-311. proteolytic enzymes: enzyme inhibition or 21. Gryglewski RJ, Korbut R, Robak J. On the substrate deprivation? Phytochemistry, 1987; 26: mechanism of antithrombotic action of flavonoids. 99-102. Biochemical , 1987; 36: 317-321. 37. Giner-Chavez BI. Condensed tannins in tropical 22. Silva EM, Souza JNS, Rogez H, Rees JF, forages. Doctoral Thesis. Cornell University. Larondelle Y. Antioxidant activities and Ithaca, NY, 1996. polyphenolic contents of fifteen selected plant 38. Serrano J, Puupponen-Pimia R, Dauer A, Aura A, species from the Amazonian region. Food Saura-Calixto F. Tannins: current knowledge of Chemistry, 2007; 101: 1012-18. food sources, intake, bioavailability and biological 23. Ghasemzadeh, A, Jaafar, HZE, Rahmat, A. effects. Molecular Nutrition Food Research, 2009; Antioxidant activities, total Phenolics and 53: S310–29. flavonoids content in two varieties of Malaysia 39. De Bruyne T, Pieters L, Deelstra H, Vlietinck A. Young Ginger ( Zingiber officinale Roscoe). Condensed vegetables tannins: biodiversity in Molecules, 2010; 15: 4324-4333. structure and biological activities. Biochemical 24. Pridham JB. In: Phenolics in Plants in Health and System Ecology, 1999; 27: 445–59. Disease, Pergamon Press, New York, 1960; 34-35. 40. Dolara P, Luceri C, De Filippo C, Femia AP, 25. Harborne JB, Baxter H. The handbook of natural Giovannelli L, Carderni G, Cecchini C, Silvi S, flavonoids, Volume 1 and 2. Chichester, UK: John Orpianesi C, Cresci A. Red wine polyphenols Wiley and Sons, 1999. influence carcinogenesis, intestinal microflora, 26. Pretorius JC. Flavonoids: A Review of Its oxidative damage and profiles of Commercial Application Potential as Anti- colonic mucosa in F344 rats. Mutation Research, Infective Agents. Current - 2005; 591: 237–46. Anti Infective Agents, 2003; 2: 335-353. 41. Gyamfi MA, Aniya Y. Antioxidant properties of 27. Tapas AR, Sakarkar DM, Kakde RB. Flavonoids Thonningianin A, isolated from the African as Nutraceuticals: A Review.Tropical Journal of medicinal herb, Thonningia sanguine. Biochemical Pharmaceutical Research, 2008; 7: 1089-1099. Pharmacology, 2002; 63: 1725–37. 28. Atmani D, Nassima C, Dina A, Meriem B, Nadjet 42. Blytt HJ, Guscar TK, Butler LG. Antinutritional D, Hania B, Flavonoids in Human Health: From effects and ecological significance of dietary Structure to Biological Activity.Current Nutrition condensed tannins may not be due to binding and & Food Science, 2009; 5: 225-237. inhibiting digestive enzymes. Journal of Chemical 29. Halliwell B, Gutteridge JMC. Role of free radicals Ecology, 1988; 14: 1455-1465. and catalytic metal in human disease, An 43. Palavy K, Priscilla MD. Standardisation of selected Indian medicinal herbal raw material

Vol. 1 No. 6 2013 www.phytojournal.com Page | 181

Journal of Pharmacognosy and Phytochemistry

containing polyphenols as major constituents. phylogenetic analysis. Proc Natl Acad Sci Journal Pharmaceutical sciences, 2006; 68: 506- USA,1998; 95: 4126–4133. 509. 58. Lasztity R, Hidvegi M, Bata A. Saponins in food. 44. Mueller-Harvey I. Tannins: their nature and Food Review International, 1998; 14: 371-390. biological significance. In: Secondary plants 59. Lacaille-Dubois MA, Wagner H. Bioactive products. Antinutritional and beneficial actions in saponins from plants: An update. In Studies in animal feeding Caygill JC and Mueller-Harvey I, Natural Products Chemistry; Atta-Ur-Rahman, ed. eds. Nottingham Univ Press (UK), 1999; 17-70. Elsevier Science. Amsterdam, 2000; 21: 633-687. 45. Mueller-Harvey I, McAllan AB. Tannins. Their 60. Morrissey JP, Osbourn AE. Fungal resistance to biochemistry and nutritional properties. In: plant antibiotics as a mechanism of pathogenesis. Advances in plant cell biochemistry and Microbiological and Molecular Biological biotechnology, Vol. 1 Morrison IM, ed. JAI Press Reviews, 1999; 63: 708–724. Ltd, London (UK), 1992; 151-217. 61. Takechi M, Matsunami S, Nishizawa J, Uno C, 46. Rao RVK, Ali N, Reddy MN. Occurrence of both Tanaka Y. Haemolytic and antifungal activities of sapogenins and alkaloid lycorine in Curculigo saponins or anti-ATPase and antiviral activities of orchioides. Indian Journal Pharma Science, 1978; cardiac glycosides. Planta Medica, 1999; 65: 585– 40: 104-105. 586. 47. Mishra SN. Analytical methods for analysis of 62. Traore F, Faure R, Ollivier E, Gasquet M, Azas N, total alkaloids in of Withania spp. Proc. All Debrauwer L, Keita A, Timon-David P, Balansard India workshop on M&AP, Faizabad, 1989; 492- G. Structure and antiprotozoal activity of 95. triterpenoid saponins from Glinus oppositifolius. 48. Krishnan R, Chandravadana MV, Ramachander Planta Medica, 2000; 66: 368–371. PR, Bharathkumar H. Inter-relationships between 63. George F, Zohar K, Harinder PS, Makkar, Klaus growth and alkaloid production in Catharanthus B. The biological action of saponins in animal roseus G. Don. Herba Hungarica, 1983; 22: 47-54. systems: a review. British Journal of Nutrition, 49. Molyneux RJ, Nash RJ, Asano N. Alkaloids: 2002; 88: 587–605. Chemical and Biological Perspectives, Vol. 11, Pelletier SW, ed. Pergamon, Oxford, 1996; 303. 50. Wink M, Schmeller T, Latz-Briining B. Modes of action of allelochemical alkaloids: Intraction with neuroreceptors, DNA and other molecular targets. Journal of , 1998; 24: 1888- 1937. 51. Elbein AD, Molyneux RJ. Comprehensive Natural Products Chemistry, Vol. 3, Barton D and Nakanishi K, ed. Amsterdam, 1999; 129. 52. Harborne JB, Tomas-Barberan FA. Ecological Chemistry and Biochemistryof Plant Terpenoids, Clarendon, Oxford, 1991. 53. Langenheim JH. Higher plant terpenoids: A phytocentric overview of their ecological roles. Journal of Chemical Ecology, 1994; 20: 1223- 1280. 54. McCaskill D, Croteau R. Some caveats for bioengineering metabolism in plants. Trends Biotechnology, 1998; 16: 349–355 55. Degenhardt J, Gershenzon J, Baldwin IT, Kessler A. Attracting friends to feast on foes: Engineering terpene emission to make crop plants more attractive to herbivore enemies. Current Opinion Biotechnology, 2003; 14: 169–176. 56. Dudareva N, Pichersky E, Gershenzon J. Biochemistry of plant volatiles. , 2004; 135: 1893–1902. 57. Bohlmann J, Meyer-Gauen G, Croteau R. Plant terpenoid synthases: and

Vol. 1 No. 6 2013 www.phytojournal.com Page | 182