Review Article Ravi Kant Upadhyay et al. / Journal of Pharmacy Research 2011,4(4),1179-1185 ISSN: 0974-6943 Available online through http://jprsolutions.info Plant natural products: Their pharmaceutical potential against disease and drug resistant microbial pathogens Ravi Kant Upadhyay Department of Zoology,D D U Gorakhpur University, Gorakhpur 273009, U.P. India Received on: 01-01-2011; Revised on: 04-02-2011; Accepted on:21-03-2011 ABSTRACT Plants contain diverse groups of phytochemicals such as tannins, terpenoids, alkaloids, and flavonoids that possess enormous antimicrobial potential against bacteria, fungi and other microorganisms. These are much safer than synthetic drugsand show lesser side effects. Approximately 25 to 50 % of current pharmaceuticals are derived from plants. Plant products are also used for the treatment of skin urinary, cardiovascular and respiratory diseases, which also show antidiarrheal, hepato-protective, hypoglycemic, lipid lowering, antiseptic, and antioxidant activities. Few important plant products such as coumarin, , benzenoide, , , , terchebulin, terflabin A-tannin, ellagic acid, ethyl acetate, galloyl and , triterpenes, flavonoids, quercetin, pentacyclic triterpenoids, guajanoic acid, saponins, carotenoids, lectins, leucocyanidin, ellagic acid, amritoside, beta- sitosterol, uvaol, oleanolic acid and ursolic acid are considered as prominent antimicrobial agents. Natural products also exhibit high susceptibility to drug resistant microbial pathogens such as methicillin- resistant and methicillin- sensitive strains of Staphylococcus aureus. These effectively check proliferation of MRSA. Some of these natural products are used as alternative medicine which are much safer and show lesser side effects than the synthetic drugs. Plant products have ethnopharmacological importance and are used as traditional medicine and food by local tribes.

Key words: Phytochemicals, antimicrobial activity, drug resistanace

INTRODUCTION The problem of microbial resistance is world wide, which arises due to indiscriminate use of was found effective against multiple drug resistant pathogens. Besides this, few nutraceuticals antimicrobial drugs. Till the date so many antimicrobial drugs failed to control infectious (Serrentino et al., 1991) were also found effective against drug resistant Pseudomonas aeruginosa diseases due to acquiring antibiotic resistance and become a serious public health problem (Adwan et al., 2006). (Peng, 2006). Besides this, synthetic drugs, after entering inside the body, generate so many biochemical aleterations and side effects in patients show cross reactivity inside the body fluid Natural plant products possess enormous antimicrobial potential (Akendengue et al., 2002; and widely inhibit bio-membrane functioning. In addition to it, microbes have generated new Cosentino et al., 1999; Delorenzi et al., 2001) and are used as tradiional medicines to kill enzyme system, which can cleave drug structure and nullify the effect of synthetic drugs. human pathogenic micro-organisms (Scazzocchio et al., 2001; Elizabeth et al., 2002 and Therefore, effective drug dose level of wide spectrum antibiotics has been increased manifold. Buwa et al., 2006). Few plant species such as B. orellana L.(Bixaceae), C. peltata L(Moraceae), There are so many cases of drug resistance, reported from all corners of the world. First C. officinalis Sepium H.B and K(Fabaceae), J. mimisifolia D. don (Bignoniaceae), J. secunda vancomycin resistance was reported in Enterococci and Staphylococcus aureus in 1990. It is P. pulchrum C.DC(Piperaceae), P. paniculta L.(Polygalaceae), and S. amerio (Asteraceae)( a single drug which efficiently controls Staphylococcus aureus infection (Smith et al., 1999). Rojas et al., 2006) are used as folk medicine for the treatment of gingivitis, bronchitis, infected Later on quinopristin /dalfopristin and methicilin resistance was came in to light. However, wounds and topical ulcers. Sesame is a used as a folk medicine in Africa and Asia for the there is no synthetic drug working against methicillin- resistant Staphylococcus aureus. treatment of bruised or erupted skins, cataract and eye pains (Ram et al., 1990) while palm oil Similarly, in many parts of the world, particularly in developed countries, fluoroquinolones is used against intestinal disorders such as diarrhea and dysentery (Gills, 1992). Morespecifically, (Pefloxacin, Ciprofloxacin and Ofloxacin) are recommended for treatment of Staphylococci few plants extracts such as B. pilosa is used as anti-helmintic and anti-protozoan (Bondarenko infection. But these drugs are not providing good clinical results. Hence, efforts have been et al., 1985) while C. peltata as anti diuretic (Caceres et al., 1991) and Orellana is used as made to explore new sources of active antimicrobials of plant origin to combat the infectious anti- malarial and anti-leishmaniasis agent (Irobi et al., 1996). The decoction of the leaves of diseases. These plant products are considered as good pharmaceuticals and some of them are C. officinalis is used to treat amoebiasis. Few ethanomedicinal plants such as Litsea glutinosa, under use as established medicine. Such alternate medicines exibit strong disease curing Vitex peduncularis, Elephantopus scaber contain carbohydrates, tannins, alkaloids and glyco- potential and can combat with drug resistant microbes and kill them. sides (Daisy et al., 2008). These are used by tribals of Orrisa for cure of major urinary tract infection (UTI) caused by pathogens viz. Staphylococcus aureus, Pseudomonas aeruginosa, Plant extract Proteus mirabilis, Enterococcus jaecalis and Escherichia coli (Prusti et al., 2008). Simi- Plants are valuable sources of medicinal compounds that contain broad spectrum biological larly, Stachytarpheta jamaicensis leaves are used as antidiarrheal and antimicrobial medicine activity. Approximately 25 to 50 % of current pharmaceuticals are derived from plants and (Sasidharan et al., 2007). Its methanolic extracts more effeciently kill Escherichia coli, S. show lesser side effects than the synthetic drugs. Normally during their life cycle, plants epidermis and Pseudomonas aeruginosa. Similarly, aqueous extracts of Mallotus oppositifolium encounter various infectious agents’ viz. viruses, bacteria, fungi and other parasites and were found effective against Shigella dysenteriae (Kamgang et al., 2006) while Streblus asper synthesize a variety of secondary metabolites capable of destroying the infectious agents. Both was found effective against microfilaiae at a very low dose 90 -33.5mg/ml (Singh and Singh, plants extracts and phytochemicals were found highly susceptible to antibiotic resistant 1976). It also shows cytotoxicity in cancer cells (Phuthawong et al., 2004). Besides his, few microorganisms. For example, single and combined plant extracts of Rhus coriaria and plans such as Althea officinalis, Origanum vulgare, Plantago lanceolata, Polygonum bistorta, Thymus vulgaris were found highly effective against multiple drug resistant Pseudomonas Satureja hortensis, Solanum dulcamara and Caesalpinia coriaria (Mohana et al., 2006) have aeruginosa (Adwan et al., 2006). Similarly, plant products isolated from Achillea shown very strong antibacterial and antifungal activity. millifolium(yarrow), Caryophyllus aromaticus (clove), Mellisa officinalis (rosemary), Salvia officinalis (sage), Syzygium joabolanum (Jambolan) and Thymus vulgaris (thyme) were found More specifically Terminalia avicenoides (Combretaceae) roots are used to cure dental caries effective against against antibiotic-resistant microbes (Nascimento et al., 2000). Ethyl gallate and skin infections (Gills et al., 1986) while bark extract of T. avicennioides is used as purified from a dried pod of Tara lactam shows susceptibility to methicillin- resistant and vibrocidal and typhocidal (Akinside et al., 1995; Akinyemi et al., 2000). Similarly, methanolic methicillin-sensistive strains of Staphylococcus aureus at 15.6 ìg/ml concentration. It effec- leaf extract of A. conzyoides is effectively used for cure of fibrinogaemia in poultry chicks tively checks proliferation of methicillin- resistant Staphylococcus aureus (Chang et al., (Ogbeche et al., 1997). Leaf extract of Ocimum gratissimum (Lamiaceae), is used for the 2003). Similarly, xanthones isolated from Calophyllum showed very high antimicrobial treatment of diarrhea, Acalpha wilkinsiana (Euphorbiaceae) for treatment of malaria and gas- activity against methicillin- resistant Staphylococcus aureus (MRSA) (Dharmaratne et al., trointestinal disorders (Akinde et al, 1987), Chelidonium majus (Papaveraceae) (Colombo et 1999). More specifically, Kigelia pinnata was found effective against vancomycin resistant al., 1996). Indigofera dendroids (Esimone et al., 1999), Indigofera oblongifera (Dahot et al., Staphylococcus aureus (Peterson, 1998). Triphala mashi is an ayurvedic formulation, which 1999) Cassia alata (Khan et al., 2001) and Indigofera suffruticosa (Leite et al., 2003) are used to cure microbial diseases. However, water extract of dry fruits of Terminalia chebula is used for the treatment of diabetes mellitus (Murali et al., 2004) while ethanolic and aqueous *Corresponding author. extracts of Sesame radiatum leaf showed very good antimicrobial activity against both Gram- Ravi Kant Upadhyay positive and Gram negative bacteria (Shittu et al., 2006;Yogesh et al., 2007). It is also used Department of Zoology, as a blood purifier and improve the mental freshness. It also shows ant-inflammatory, D D U Gorakhpur University, analgesic, anti-arthritic, hypoglycaemic anti-aging properties (Jagetia et al., 2002). Gorakhpur, India 273009 Psidium guajava (Myrtaceae) is also used as a folk medicine that shows multiple diseases Journal of Pharmacy Research Vol.4.Issue 4. April 2011 1179-1185 Ravi Kant Upadhyay et al. / Journal of Pharmacy Research 2011,4(4),1179-1185 curing potential and is used to cure diarrhea, gastroenteritis, sore throats, bleeding gums and residues ,hydrolytic enzymes containing mannose-6-phosphate.and help in glycoprotein syn- other digestive complaints (Lozoya et al., 1990). Similarly, Amazon leaf tea is used for liver thesis and control protein levels in blood. Lectins are used in blood typing, and problem neuralgia, rheumatism and arthritis pain fever diarrhea, coughs, grippe, difficult hemoagglutination test and precipitate glycoconjugates. Concanavalin A is a lectin which is childbirth, asthma, asthenia, hypertension and parasites (Feng et al., 1962). It is also used for used for characterization and purification of sugar containing molecules and cellular structures. control of inflammation of mucous membrane. Bark, roots and leaves are used for diabetes, Lectins show diverse biological activity. For example some larger lectin molecules such as sedative, antispasmodic. It also works as a cardiac relaxant and heart tonic. It contains Jaclin (Favero et al., 1993), MAP30 (Lee-Huang et al., 1995) and GAP31 (Bournibaiar et al., important phyto-constituents such as tannins, triterpenes, polyphenols, flavonoids, quercetin, 1996) were found effective against Cytomegalovirus proliferation (Lewis and Elvin-Lewis pentacyclic triterpenoids, guajanoic acid, saponins, carotenoids, lectins, leucocyanidin, el- 1995). Besides this, lectins found in Guava leaf bind to Escherichia coli and prevent its lagic acid, amritoside, beta- sitosterol, uvaol, oleanolic acid and ursolic acid (Kamath et al., adhesion to the intestinal wall (Rodriguez et al., 2001). It also shows tranquilizing effects on 2008). These phytochemicals showed antidiarrheal, hepatoprotective, hypoglycemic, lipid intestinal smooth muscle and inhibit chemical processes occur in diarrhea and aid in the re- lowering, antibacterial and antioxidant acivities. Guava fruits and leaves are rich source of absorption of water in intestine. Lectins were found effective in diarrhea, dysentery and vitamin C and A, fibres, fatty acids and a good source of pectin. Guava leaves contain gastroenteritis. Lectins from Talisia esculenta have shown antibacterial activity against polyphenols that show antioxidant (Begum et al., 2004) and anti-proliferative effects against Streptococcus mutans (UA 159), Streptococcus sobrinus (6715), Streptococcus sanguinis human mouth epidermal carcinoma and murine leukemia (Manosroi et al., 2006). (ATCC 10556), Streptococcus mitis (ATCC 903) and Streptococcus oralis (Groppo et al., 2007). Lectins isolated from Galanthus nivalis and Hippeastrum inhibited a wide variety of Similarly, Ageratum conzoides is used as traditional medicine (Correa, 1984) for the treatment HIV virus type-1 and HIV-2 strains (balzarini et al., 2004). Algal lectins from Eucheuma serra of pneumonia, wounds and burns (Durodola, 1977). It is used for quick and effective healing and Galaxaura mariginata inhibit the growth of Vibrios vunificus and Vibrio pelaguis (Liao of burn wounds, and is recommended as antirheumatic, anti dysenteric (Vera, 1993) and anti- et al., 2003). lithic agent (Borthakur and Baruah, 1987). It is also used to treat fever, rheumatism (Jaceoud, 1961; Correa, 1984), headache, colic (Menut et al.,1993; Bioka et al.,1993), arthrosis and Polypeptides also helpful in articulation mobility (Marques Neto et al.,1988). Its aqueous extract works as Peptides are positively charged biomolecules, contain 14-15 amino acid residues bound by bactericidal (Almagboul, 1985; Ekundaya et al., 1988) while solvent extract showed inhibitiory disulphide bonds and inhibit microbial growth (Balls et al., 1942). These are effecetor activity against S. aureus, B. subtilus, E. coli and P. aeruginosa (Duradola, 1977; Almagboul molecules which bind with polysaccharide receptors (Sharon and Ofek, 1986) and act upon et al.,1985). It contains various secondary metabolites like flavonoids, alkaloids, cumarins, microbial membranes dislodge them and form ion channels (Terras et al., 1993). Two conyzorigum, a cromene and tannins which were biologically active against diverse pathogens important categories of peptides are cercopins and defensin type having three-disulphide (Vyas and Mulchandani, 1986). Alkaloids mainly Pirrolizidinic group, 1-2- desifropirrolizidinic bridge. Antimicrobial petides (AMPs) are an important aspect of defense in mutlicellular and licopsamine from Ageratum conyzoides shows hepatotoxic activity (Weindenfeld and organisms. Both Drosophila melanogaster and dipterans synthesize eight types of AMPs. Roder, 1991). Similarly, Citrus sp shows antibacterial, antifungal, analgesic and show muscle These target three groups of bacteria, gram positive bacteria (Defensins), gram negative bacteria relaxing activity (Achola, et al.,1994). It contains polymethoxylated flavonoids and coumarin cercopins, drosocin, attacins, diptericin and fungi drosomycin. Insects contain cateionic as secondary metabolite (Afek et al.,1986) which work against two human pathogens Tricho- AMPs having less than 100 amino acids. Besides this, antibacterial proteins widely occur in phyton mentagrophytes and Microsporum canis and two opportunistic bacteria i.e Escheri- plants which help in plant defense.Thionin a peptide isolated from barley and wheat (Mendez chia coli and Staphylococcus aureus. Similarly peel and seed extracts of Atung (Parionarium et al., 1990), which was found highly toxic to yeast and Gram and Gram-positive bacteria glaberrimum Hassk) fruit exhibit strong antimicrobial activity. The seed extracts effectively (Fernandez et al., 1996). Besides this, another peptide Febatin is isolated from faba, beans work against food spoilage, pathogenic bacteria and pathogenic yeast strains. It also work as (Zhang and Lewis 1997) that contains 47 amino acid residues, structurally much similar to a good food preservative and inhibit the growth of fungi, yeast and Bacteria (Moniharapon et thionin effectively work against E.coli, P. aeruginosa and Enterococcus hirae. Thionin is a al., 2004). Similarly, methanolic extract of Khaya senegalensis, Pilio stigma reticulatum, basic peptide having low molecular weight (~5kDa) that containd sulphur rich residues Securidaca longepedunculata and Terminalia avicennoides, Anchomanes difformis, Cassytha (arginine, lysine, and cyctine) and shows toxic effects against bacteria, fungi and yeast cells spp, Lannea kerstingii, Parkia clappertioniana, Striga spp, Adansonia digitata and Prosopis (Garcia-Olmedo et al., 1989; Bohlmann and Apel, 1991; Fernandez et al., 1996). Balls et al., africana have shown strong trypanocidal activity against T. brucei brucei or T. congolense (1942) crytalized a toxic substance named Purothium from wheat endosperm (Triticum aestivum (Atawodi et al., 2003). Besides this, Rhododendron ponticum L, Prunus laurocerasus L, L.) with low molecular weight that contain high sulphur content. Proteins similar to Purothiun Punica granatum L, Anthemis cotula L, Cichorium intybus L, Viscum album L, Pavaver are being isolated from other ceral leaves and ebdosperms such as barley (a and ß-hordothionins) hybridum L, Malva rotundifolia L and Rhus cariaria L. (Dulger et al, 2004) and Linaria (Redman and Fisher, 1969; Ponz et al., 1983; Rodriguez-Palenzuela, 1988), oat (a and ß- corifolia (Desf) have shown strong antimicrobial activity (Gonuz et al., 2005). Few actino- avenohtionins (Bakes and Lasztity, 1981). Thionins also occur in the endosperm of all the mycetes isolates from Phoomdi from Western India have shown antimicrobial activity against species of the genus Triticum and Aegilops (Carbonero and Garcia-Olmedo, 1969). It is highly Bacillus subtilis , Staphylococcus aureus, E. coli, Klebsiella pneumoniae, Micrococcus toxic to yeast and Gram-positive bacteria. Another peptide, Febatin isolated from faba beans, luteus, Mycobacterium phlei, Candida albicans (Singh et al., 2006 ). contains 47 amino acid residues, structurally similar to thionin and effective against E.coli, P.aeruginosa and Enterococcus hirae. Some larger lectin molecule Jaclin (Favero et al 1993), Ayurvedic preparations were also found effective against Aspergillus (Dhuley, 1998) and MAP30 (Lee-Huang et al., 1995) and GAP31 (Bourinbaiar et al., 1996) were found effective Propionibacterium acnes (Paranjpe et al, 1995). Most of these preparations contain terpe- against Cytomegalovirus proliferation (Lewis and Elvin-Lewis 1995). Few plant species noids, flavonoids, benzoic acids and esters and substituted phenolic acids and esters (Amoros contain phenylpropanoids as essential oil constituents, which are made up of a chain of 3 et al., 1992) which were found effective against bacterial and viral infection such as infuenza carbons bound to an aromatic ring of 6 carbons and are mainly derived from phenylalanine. virus. Propolis crude extract was found active against an ancyclovir-resistant mutant of HSV- Another toxic protein was isolated from Pyrularia pubera seeds, a parasitic plant in the order 1, adenovirus type 2, vesicular stomatitis virus and poliovirus (Amoros et al., 1992). Similar as mistletoe (Santalales). The Pyrularia thionin presents four disulphide bridges like cereal activity is reported in Phyllanthus embolica, which contains ascorbic acid (Prakash et al., thionins and share eight consecutive amino acid residues (14 to 21) identical to crambin. 2000), astragalin-flavonal (El- Mekkawy et al., 1995), gallic acid benzenoid, emblicol, However, the group of thionins with the highest degree of similarity to Pyrularia thionin is phyllemblic acid, Emblicanin A, Emblicanin B, , Punigluconin- Tannin represented by the viscotoxins (Vemon et al., 1985) (Bhattacharya et al., 2000), ellagic acid coumarin (Jamwal et al., 1959). Terminalia chebula contains arjungenin, arjunglucoside I (Reddy et al., 1994), gallic acid, benzenoide (Grampurohit Alkaloids et al., 1986), chebulic acid coumarin , corilagin, punicalagin , terchebulin, terflabin A-tannin Alkaloids are heterocyclic secondary plant metabolites which occur in plants containing basic (Lin et al., 1990). Beta sitosterol, gallic acid, ellagic acid, ethyl acetate, galloyl glucose and nitrogen atoms. These are of three different types i.e. true alkaloids (have heterocyclic ring with chebulagic acid have been isolated from fruits of T. belerica. All these compounds are nitrogen), proto-alkaloids does not have heterocyclic ring with nitrogen and pseudo-alkaloids prominent antimicrobial agents. More specifically, phytochemicals such as lectins, tannins, have heterocyclic ring but not derived from amino acids. Few important alkaloids are harmine terpenoids, alkaloids, and flavonoids showed broad spectrum antimicrobial activities (Cowan, (C H N O), harmaline (C H N O), harmalol (C H N O), tetrahydroharmine (C H N O), 1999). These products are successfully used against many pathogenic bacteria (Suresh et al., 13 12 2 13 14 2 12 12 2 13 16 2 harman (C12H10N2), harmine acid; harmanamide, acetylnorharmine and ephedrine are 1992), fungi (Bilgrami et al., 1992), viruses (Pacheco et al., 1993) and for the treatment of skin phenethylamine alkaloids. These are also used as local anesthetic and stimulant. The common diseases and respiratory disorders (Duraipandiyan et al., 2006). Among different metabolites stimulants are caffeine, nicotine and morphine and antimalarial drug quinine. Morphine, an screened from plants terpenoids, tannins, flavonoids and naphthoquinones have shown very alkaloid, isolated from the Opium poppy Papaver somniferum (Fessenden and Fessenden strong antimicrobial (Cowan, 1999), antiplasmodial (El-Tahir et al., 1999) and leishmanicidal 1982) is used for the treatment of bacterial and viral diseases. Both codeine and heroin are activity (Kayser et al., 2003). derivatives of morphines and used as antimicrobial while erberine is potentially used against trypanosomes (Freiburgsaus et al., 1996; Hopp et al., 1976). Clove, Jambolan and pomegran- Plant products ate contain quinoline alkaloids and show synergistic effects against Pseudomonas aeruginosa Lectins (Chandler, 1982). Diterpenoid (alkaloids), commonly isolated from the plants of the buttercup Lectins are positively charged non-enzymatic biomolecules, contain disulphide bonds and family (Jones and Luchsingen 1986; Atta-Ur-Rahman & Chaudhary 1995) have shown inhibit microbial growth (Balls et al., 1942; Zhang and Lewis, 1997). These bind with antimicrobial properties (Omulokoli et al., 1997). Solamargine,a glycoloid from the berries of polysaccharide or glycoproteins receptors on red wood cells extracellularly and also act upon Solanum khasianum is useful against HIV infection (McMahon et al., 1995, Sethi et al., microbial membranes to form ion channels (Terras et al., 1993 and Zhang and Lewis, 1997). 1979). It was also found effective against intestinal infections associated with AIDS (McDevitt These competitively inhibit activity of microbial proteins (Sharon and Ofek, 1986). Some et al, 1996). Some alkaloids also found effectiveagainst Giardia, Entamoeba species and lectins are found on the surface of mammalian liver cells which specifically recognize galactose diarrhoea (Ghoshal et al., 1996).

Journal of Pharmacy Research Vol.4.Issue 4. April 2011 1179-1185 Ravi Kant Upadhyay et al. / Journal of Pharmacy Research 2011,4(4),1179-1185 Flavonoids, flavones and flavanols and pyrogallol are highly oxidized phenols, which inhibit enzyme activity in microbes. Flavonoids are secondary metabolites which possess flavone backbone (2-phenyl-1,4- Eugenol, a polyphenol isolated from olive oil, is a potent antibacterial and antifungal agent. benzopyrone). These are ketone copmounds are collectively known as Vitamin P and citrin. Few plant species such as Salvia sclarea, Salvia glutinosa, Salvia pratensis, Lavandula Flavonoids are “the most common group of polyphenolic compounds which are found angustifolia, Calendula officinalis, Matricaria recutita, Echinacea purpurea, Rhaponticum carthamoides, Juglans regia, Melilotus officinalis, Geranium macrorrhizum, Potentilla ubiquitously in plants”. Flavonoids occur as C6-C3 unit linked to an aromatic ring. These are hydroxylated phenolic substances, which contain one carboxyl group and are synthesized in fruitcosa and Salvia officinalis possess phenolic compounds and show antimicrobial and plants in response to microbial infection. Due to hydroxylation flavonoids show activity antioxidant activity. And show high radical scavenging activity (RSA) (Miliauskas, et al., against infectious agents. There are three categories of flavonoids flavonoids, derived from 2- 2004). phenylchromen-4-one (2-phenyl-1,4-benzopyrone) structure (examples: quercetin, rutin), isoflavonoids, derived from 3-phenylchromen-4-one (3-phenyl-1,4-benzopyrone) structure Quinones: neoflavonoids, derived from 4-phenylcoumarine (4-phenyl-1,2-benzopyrone) structure. Quinones are organic compounds having a fully conjugated cyclic dione structure. These are derived from aromatic compounds by conversion of an even number of –CH= groups into – Flavonoids both flavonols and flavanols are most commonly known for their antioxidant C(=O)– groups with any necessary rearrangement of double bonds. These are highly reactive activity. Mode of action of both flavones and flavanoides is membrane disruption and enzy- natural compounds possess aromatic rings with two ketone substitutions in their chemical matic bindings, which depends on hydroxylation due to presence of hydroxyl groups on their structure . Quinones are common constituents of biologically relevant molecules (e.g. Vitamin rings. Few flavanoids such as glycerrhizin, chrysin and swertifracheside were found active K1 is phylloquinone). These compounds act as oxidizing agent for example benzoquinone. against HIV viruse. Besides this, querctin, a flavanoid compound was found effective against These compounds mostly appear after broughting reaction during fruit and vegetable chopping HSV-1, Poliovirus-1, Parainfluenza virus-3, while other flavanoids like naringin, herperatin or cutting vegetable. Ubiquinone known as coenzyme is an oxidation-reduction compound and catechin were not found so much effective like quercitin (Kaul et. al., 1985). Simialry, and helps in electron transport chain. Vitamin K is a derivative of quinone which possesses Galangin isolated from a herb Helichrysum aureointens are not effective against HSV-1 viruse anti-hemorahagic activity due to its oxidation in body tissues. Quinones form complex with and gram positive bacteria (Meyer et al., 1997) while alpinumis flavone is effective against nucleophilic amino acids found in proteins and show very high antimicrobial activity. These Schistosomal infection (Perrett, et al., 1995). Similarly,Flavanoids isolated from roots of target membrane bound enzymes and cell wall polypeptides more specifically. Glycyrrhiza uralensis, were mainly identified as Pterocarpenes glycyrrhizol A(1) and Antianthraquinones isolated from Cassia italica were found highly active against Bacillus glycyrrhizol B(2), along with five known isoflavonoids, 5-o-methyl glycryol (3), isolycyrol antroacis, Cornybacterium pseudodifothecium, and Pseudomonas aeruginosa, Pseudomo- (4), 6,8-diisoprenyl-5,7, 4’-trihydroxy isoflavone (5), and gancaonin G (6) possess very high nas pseudomalliae (Kazmi, et al., 1994). Hypercicum isolated from Hypericum perforatum is antimicrobial activity (He et al., 2006). More exceptionally,glycyrrhizol A(1) and 6, 8- an anthraquinone which serves as an anti-depressant (Duke, 1985). Quinones also show diisoprenyl-5,7, 4’-trihydroxy isoflavone (5) exhibited potent antibacterial activity against antitumoral activity. Few plant species such as Cassia alata, Cassia occindentalis, Garcinia Streptococcus mutants at an MIC of 1 and 2 microg/ml, while glycyrrhizol B (2)and gancaonin cola and Ocimum basilicum contain quinones which are used as traditional medicine against G(6) showed more moderate activity at the same concentration (He et al., 2006). malaria. These show very low IC50 value 1 microgram/ml (Kayembe et al., 2010). Quinones are well established antimicrobial drugs (Kanok-medhakul et al., 2005, Lauret et al., 2006, Flavonoids isolated from P. guajava leaf effectively cure and treat acne and especially show Eyong et al., 2006), Atovaquonone, lapachol and lapinone are quinones. These are intermedi- anti-inflammatory activity (Qadan et al., 2005). In addition to it quercetin-3-O-alpha-1- ate compounds which are formed before melanin synthesis pathway in human skin and are arabinopyranoside (quaijaverin) isolated from this plant has shown very high activity against ubiquitous in nature. plague pathogen and inhibits the growth of Streptococcus aureus (Abdelrahim et al., 2002). It is also used to fight against infantile diarrhea and infantile rotaviral enteritis. Besides Tannins: flavones were found inhibitory to respiratory syncytial virus (RSV) (Barnard et al., 1993, Kaul Tannins are used for tanning or colouring the leather and help in precipitation of gelatin et al., 1985). Similarly 4,5,6,7-pentamethoxy flavone (tangeritin ) and 3, 4, 5, 6, 7, 8- polyphenols that are obtained from various parts of different plants (Gajendiran and Mahadevan, hexamethoxy flavone (nobiletin ) isolated from C. reticulata and 6, 7-dimethaxy coumarin 1990). Tanins are diverse group of polyphenolic compounds. These possess sufficient hy- isolated from C.lemon have shown very high disease curing potential. Flavonoids reduce droxyls and other suitable groups (such as carboxyls) to form strong complexes with proteins erythrocyte aggregation and sedimentation rates in human blood (Robbins, 1976) and exhibit and other macromolecules. Tannins are strong antimicrobial agents and are normally used for antiviral, antimutagenic and antimicrobial properties (Afek et al., 1986). Therefore, intake of treatment of infection (Anesini et al.,1993; Haslam, 1996)). Tannins penetrate through mem- flavonoid rich food materials reduces the risk of heart diseases due to their antioxidant activites brane, adhere on it and show competitive inhibition of enzymes and bind to cellular envelops. (Young et al., 1999; Tripoli et al., 2007). These are also found active against opportunistic Two categories of tannins, hydroxylizable (gallic acid) and condensed (proantocyanidins) act systemic mycosis, as well as the rising prevalence of drug resistance in human’s pathogenic as strong antimicrobial agents. Tannins are potential insect growth inhibitors which inhibit bacteria (Afek et al., 1986). PMFs (Penta methoxy flavones) are lipophytic compounds when the growth of larvae (Schultz, 1988). Tannins inhibit growth of larvae, effect moulting in usually found in vacuoles or in the wax cuticle of plants. Besides this, these are generally found insects and are inhibitors of reverse transcriptase enzyme. More specifically vegetable tannins attached to sugar moieties (Glycosides) or as free aglycones (Robards et al., 1997) and shown stimulate phagocytic cells, to engulf tumour cells and show wide range of anti-infective strong antibacterial activity (Johann et al., 2007). These compounds play an important role actions. Tannins are toxic to filamentous fungi, yeast, and bacteria. Condensed tannins bind in protection from UV radiation and microbial pathogens (Yousef and Tawil, 1980; Fang et al., cell walls of ruminal bacteria, preventing growth and protease activity. Besides this, tannins 2001). Besides this, flavonoids from C. reticulata kill Schistosoma mansoni and other were found inhibitory to viral reverse transcriptase activity (Kaul et al., 1985). Sagetannins parasitic worms (Hamed and Hetta, 2005). Similarly flavonoids, from onion were found were found active against A. naeslundiis ATCC 12104, with an MIC value of 62.5 microg/ml highly effective against a wide variety of microorganisms (Ekwenye et al., 2005). including methicillin sensitive S. aureus (MRSA) (Liu et al., 2006).

Phenols: Tanins play a role in protection from predation and perhaps in growth regulation. Tannins have Phenols or phenolics are widely distributed organic compounds occur in the plant kingdom. a protective function in the bark of the roots and stems, or any outer layers of plants and possess These molecules primarily help in defense against predators and pathogens. These act as astringent properties due to their high polyphenol content. These form strong complexes with attractants and help in dispersal of seeds and pollens of plants by the insects. Phenolics are proteins, starch and other macromolecules. Tannins can modulate inflammation caused by bioactive phytochemicals consist of single substituted phenolic ring. These are a class of food allergens and pathogenic microflora in the GI tract. These are very strong antimicrobial chemical compounds contain a hydroxyl group bonded directly to an aromatic hydrocarbon agents and inhibit the growth of Kocuria rhizophila, Staphylococcus aureus, Bacillus subtilis, group. Phenolic compounds are primerly synthesized from the product of shikimic acid and Pseudomonas aeruginosa. Tannins effectively kill the GI tract flora and make it free from pathway and possess two or more hydroxy groups bonded to the aromatic ring(s) in the same pathogenic bacteria.The tannins appeared to reduce the phosphorylation of critical intracellular molecule. The simplest examples are the three benzenediols, each having two hydroxy groups kinases and inhibited NF-kappaB p65 activity, which can account for the decrease in MMP on a benzene ring. Few acids are representatives of phenolics, these are ellagic acid, tannic production and in their catalytic activity. Condensed tannins (CT) isolated from Shinnery oak, acids, vanillin, cinnamic acid and caffeic acids are phenylpropane derived compounds, which Post oak, Locust, Blackjack oak , Skunk bush Sericea lespedeza, commercial Quebracho possessing a C3 side chain at a lower level of oxidation and containing no oxygen. Phenols Sumac Plum.inhibit the growth of Escherichia coli, Klebsiella pneumoniae, and Staphylo- are germicidal and disinfectants in nature. coccus aureus at a very low dose (0,2, 4 and 8 mg CT/ml) and high dose levels (0, 50, and 100 mg CT /ml). Besides this, plant tannin extracts are used as alternatives and supplements Phenols are synthesized due to external stimuli such as microbial infections, UV light and to conventional antimicrobial feed additives. ceratin chemicals. These do not involve in primary metabolic processes of growth and development. Phenolic compounds are highly active phytochemicals, which show immense Tannins occur in plant leaves and kill gut microbes after being consumed by ruminants. These antimicrobial potential. These chemicals possess single phenolic ring in their structure. efficiently eliminate Staphylococcus aureus (44.3%), Streptococcus sp. (18%), coagulase- Phenolic compounds such as Cinnamic acid and caffiec acids are highly active phytochemicals, negative staphy-lococci (12.8%) (Waage et al., 1999) and gram-negative rods, Klebsiella sp., which show immense antimicrobial potential against microbes (Jansen et al., 1987; Miliauskar Escherichia coli and Enterobacter sp. (Guifry, 1985 and Min et al, 2008). Tannins isolated et al., 2003). Glycoside oleuropein and its phenolic aglycone inhibit the growth of Geotrichum from the plant species, Solanum trilobatum (Solanaceae-herbs) exhibited antmicrobial activity candidum, Rhizopus sp. and Rhizooctonia solani Oleuropein also inhibit growth of Lactoba- against Staphylococcus aureus, Streptococcus pyrogens, Salmonella typhi, Pseudomonas cillus plantarum (Juven and Henis, 1970). Harborne (1964) reported antimicrobial action of aeruginosa, Proteus vulgaris and Escherichia coli . MIC of the tannins ranged between 1.0 pleuropein against S. cerevisiae, S. oviformis, S. carlsbergensis, C. albicans, C. tropicalis and 2.0 mg/ml while the MBC values ranged between 1.5 and 2.0 mg/ml. Tannins also and C. krusei. Terragon and thyme are also effective against microorganisms. Both catechol possess antiviral (Lin et al., 2004), antibacterial (Akiyama et al., 2001; Funatogawa et al.,

Journal of Pharmacy Research Vol.4.Issue 4. April 2011 1179-1185 Ravi Kant Upadhyay et al. / Journal of Pharmacy Research 2011,4(4),1179-1185 2004), antiparasitic (Bhagavathi et al., 1999; Yang et al., 2000; Tanimura et al, 2005), invariably Gram negative and Gram-positive bacterium Staphylococcus aureus. In addition, antifungal, antimitotic, antioxidant and anti-tumours potential (Purushothaman et al., 1969; to it presence of an aromatic dimethoxy arrangement is apparently favourable against those Shahjahan et al., 2004; Shahjahan et al., 2005). Solanum trilobatum contains rich amount of microorganisms which require special growth factors such as beta-hemolytic Streptococcus, calcium, iron, phosphorus, carbohydrates, fat, crude fibre and minerals in the leaves (Jawahar Streptococcus pneumoniae and Haemophilus influenzae. A combination of these structural et al., 2004). It is used to cure asthma, arrest blood vomiting, to reduce blood glucose level features, two methoxy functions and at least one additional phenolic group as reflected by the and bilious matter phlegmatic rheumatism and several kinds of leprosy. highly oxygenated coumarins, identify promising candidates with antibacterial broad-spec- trum activity. Catechins and gallates: Catechins are a polyphenolic antioxidant plant metabolites. The term catechin is commonly Coumarins i.e. 5-methoxy-6,7-methylenedioxycoumarin,7-(2',3'-epoxy-3'-methylbutyloxy)- used to refer to the related family of flavonoids and the subgroup flavan-3-ols (or simply 6-methoxycoumarin,6,7 methylenedioxycoumarin (ayapin), 6-hydroxy-7-(3'-methylbutyl-2'- flavanols). Catechins are differentiated from the ketone-containing flavonoids such as quercitin en-oxy)-coumarin (prenyletin) and 6-methoxy-7-(3'-methylbutyl-2'-en-oxy)-coumarin and rutin, which are called flavonols. Catechin and epicatechin are epimers, with (-)-epicatechin (prenyletin-methyl-ether) isolated from Pterocaulon spp, Pterocaulon and (+)-catechin being the most common optical isomers found in nature. Catechin was first alopecuroides, Pterocaulon balansae and Pterocaulon polystachyum (Asteraceae) are used to isolated from the plant extract catechu, (Acacia catechu L.) from which it derives its name. treat animal mycoses (Kayser et al., 1999). Among the different components of the active They are present in nearly all teas made from Camellia sinensis, including white tea, green tea, extracts, only the mixture of prenyletin and prenyletin-methyl-ether isolated from Pterocaulon and Oolong tea. Catechins constitute about 25% of the dry weight of fresh tea leaf. polystachyum showed activity against Cryptococcus neoformans, Microsporum Epigallocatechin gallate is the most abundant catechin in tea. Gallocatechin isolated from the gypseum, Trichophyton rubrum and Trichophyton mentagrophytes. Similarly counmarins methanol extracts of guava leaf showed antimutagenic activity against Escherichia coli were found active against Gram-positive (Staphylococcus aureus, beta-hemolytic Streptococ- (Matsuo, et al., 1994). Another stereoisomer, (-)-catechin, is released from the roots of the cus and Streptococcus pneumoniae) and Gram-negative bacteria (Escherichia coli, Klebsiella invasive weed, spotted knapweed. It acts as an herbicide to inhibit competition by a wide pneumoniae, Pseudomonas aeruginosa, Proteus mirabilis and Haemophilus influenzae), range of other plant species. This phytotoxic compound inhibits seed germination and using the microdilution broth method (Kayser et al., 1999). growth. Aqueous extracts of Japanese green tea (Camellia sinensis) showed reverse beta-lactam resistance in methicillin-resistant Staphylococcus aureus (MRSA). Octyl gallate, (-)-epicatechin Besisdes this, coumarin and coumarin derivatives were found active against Bacillus cereus gallate (ECG) and (-)-catechin gallate (CG)\ exhibited direct antibacterial activity against S. MIP 96016, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, and aureus BB568 (16 mg/l) (Stapleton et al., 2004) Staphylococcus aureus ATCC 25923. The inhibitory effects of coumarins are attached with their substitution patterns. Osthenol showed the most effective antibacterial activity against Terpinoids: Gram-positive bacteria with MIC values ranging between 125 and 62.5 microg/ml (de souza These are most diversified group of secondary plant metabolites and are derived from a basic et al., 2005). Similarly coumarins i.e. imperatorin, isoimperatorin, heraclenol, oxypeucedanin structure of 5 carbons (C5H8), most commonly called as isoprenoid unit . These are a large and hydrate and heraclenin isolated from Angelica have shown antimicrobial activity against Gram diverse class of naturally-occurring organic chemicals similar to terpenes. These are classified positive and negative bacteria, oral pathogens and human pathogenic fungi (Widelski et al., on the basis of isoprenoid units found in skeleton. Most of them are multicyclic structures that 2009). The coumarins showed broad spectrum growth inhibitory activity with minimum differ from one another not only in functional groups but also in their basic carbon skeletons. inhibitory concentrations ranging from 0.9 to >12.4 ìm. Terpinoids are phenylpropanoids interact with the cell membrane and accumulate in the lipidic bilayer of bacteria. Terpenoids are used as herbal medicine used for their strong antibacterial, Polyacetylene: antineoplastic, and other pharmaceutical functions. Terpenoids contribute to the scent of It is an organic polymer with the repeat unit (C2H2)n. It consists of a long chain of carbon eucalyptus, the flavors of cinnamon, cloves, and ginger, and the color of yellow flowers. Well- atoms with alternating single and double bonds between them, each with one hydrogen atom. known terpenoids include citral, menthol, camphor, Salvinorin A in the plant Salvia divinorum, One distinguishes trans-polyacetylene, with all double bonds in the trans-configuration, from and the cannabinoids found in Cannabis. The steroids and sterols in animals are biologically cis-polyactylene, with all double bonds in the cis configuration. Each hydrogen atom could be produced from terpenoid precursors. These are most diversified group of secondary plant replaced by a alkyl functional group. Polyacetylene inhibit the growth of S. aureus and B. metabolites, derived from a basic structure of 5 carbons (C5H8) commonly known as iso- subtilis (Estevez-Braun et al., 1994) and effectively work against urinary tract and cutaneous prenoid unit. Terpenoids are classified based on isoprenoid units found in skeleton. These are infections, gastrointestinal disorders, respiratory diseases, parasitic protozoan and helmintes phenylpropanoids which interact with the cell membrane and accumulate in the lipidic bilayer diseases and inflammatory process (Leite et al., 2006). of bacteria (Liu, et al., 2007). Terpenoids or terpenes are active against bacteria, viruses and protozoa, while triterpenoids like beutilinic acid significantly inhibit growth of HIV virus. Glycosides The ethanol soluble fractions of purple clove yields terpenoids, which show excellent activity Glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to against Bacillus subtilis, Staphylococcus aureus and Gram-negative bacteria as well as another group via a glycosidic bond. More specifically glycosides possess sugar which is Candida albicans. Tricholorbdat-A, ditrepenoid, directly inhibits Helicobacter pylori activ- bound to a non-carbohydrate moiety. Formally, a glycoside can be linked by an O- (an O- ity (Cowan 1999; Prabuseenivasan et al., 2006). T. amplexicaule Roth. Contains biologically glycoside), N- (a glycosylamine), S-(a thioglycoside) or C- (a C-glycosyl) glycosidic bond.. active terpenoids such as beta-sitosterol, alpha-amyrin, lupeol, hexacosanoic acid, ceryl This sugar group is known as the glycone and the non-sugar group as the aglycone or genin alcohol and hexacosane. These compounds were found effective against selected pathogenic part of the glycoside. The glycone consist of a single sugar group (monosaccharide) or several bacteria, Escherichia coli, Staphylococcus aureus and fungi, Aspergillus flavus and Penicil- sugar groups (oligosaccharide). In living organisms glycosides play numerous important roles lium chrysogenum etc (Singh and Singh 2003). in self medication. Many plants store inactive glycosides in their cells; which can be activated by enzyme hydrolysis. This causes the sugar part to be broken off, making the chemical. Roots Besides this, few diterpenoids such as 18-beta-D-3’,4’-diacetoxyxylopyransoyl-entkaur-16- of Vanda roxburghii contain a glycosides 17-a-hydroxy 14, 20-epoxy –1-oxo-(22R)-3a-(O-a- ene,18-betaL-3’,5’-diacetoxyarabinofuranoyl-ent, 18-beta-D3’, 6’diacetoxyglucopyransoyl ent- D-glucopyranosyl )-S, 24- with adienolide (VR-2) has shown significant antibacterial and kaur-16-ene, ent-isopimar-8, 15-diene-19-oic acid, isolated from Sagittaria pygmaea have antifungal activity against Bacillus cereus, Bacillus subtilis, Escherichia coli Shigella dysenteriae shown significant antibacterial activity against Streptococcus mutants ATCC25 174 Actino- and Pseudomonas aeruginosa (Ahmed et al., 2001). Vanda roxburghii also contains another myces viscosa ATCC27 044 (Lin, 2007). Diterpenoids and sagittines isolated from Sagittaria i.e. glycoside, melianin (VR-1) which posess good antimicrobial activity against number of sagittifolia, exhibited very high antibacterial activity against the Streptococcus mutants pathogenic bacteria such as Aeromones hydrophilla (ATCC 7966), Listeria monositogenes ATCC 12104, with MIC values between 62.5 and 125 microg/ml. Two clerodane diterpines (ATCC 1911), Escherichia coli (ATCC 11230), Enterobacter aerogenes (ATCC 13048), viz, Kolavenic acid (1) and 16-oxo-cleroda-3, 13(14) E-diene-1s-oic acid (2) isolated from the Corynebacterium xerisis (CCM 2824), Corynebacterium glutamicum (ATCC 13022), Pro- petroleum ether extracts of the seed of Polyalthia longifolia were found active against Bacillus teus vulgaris (ATCC 8427), Serratia marcescens (NRRL3284), Bacillus cereus (ATCC7064), cereus, Bacillus subtilis, Escherichia coli, Shigella flexaneriae and Shigella boydii at a very Bacillus subtilis (ATCC 6633), Bacillus brevis (ATCC 9999), Bacillus sphaericus, Bacillus low concentration i.e. 4-64 µg/ml. Both the compounds have shown significant cytotoxic megaterium, mycobacterium smegmatis (CCM 2067), Sarcina lutea, Micrococcus luteus activities (Islam et al., 2001). Diterpenoids commonly isolated from the plants of the butter- (LA2971), Staphylococcus aureus (ATCC 6538P), Staphylococcus epidermidis (NRR B- cup family (Jones et al., 1986; Atta-Ur-Rahman & Chaudhary 1995) have shown very high 4877), Alcaligenes faecalis (CCM 3763), Alicaligenes eutrophus, Salmonella parathyphi B, antimicrobial properties (Omulokoli et al., 1997). Solamargine,a glycoloid from the berries of Salmonella typhi (ATCC 19439), Salmonella typhimurium (CCM 5445), Erwinia amylovora, Solanum khasianum is useful against HIV infection (McMahon et al., 1995, Sethi et al., Rhodotorula rubra, Sacchromyces cervisiae (ATCC 9763) and fungi Aspergillus oryzae 1979). It was also found effective against intestinal infections associated with AIDS (McDevitt (Dulger et al., 2004), Aspergillus fumigatus, Candida albicans, Hensinela californica and et al, 1996). Rhizopus arijae (Ahmed et al., 2002). The cyanogenic glycosides are a bound form of the animal toxin cyaninde. It si released from glycoside after enzymic hydrolysis. Cyanogen Coumarins: linamarin in Lotus corniculatus is found protective against fungal organisms. Coumarins are formed by fusion of benzene and pyrene rings and show diverse biological activity such as anti-inflammatory, antithrombic and vasodilatory. Few coumarins such as Toxins warfarin are taken as oral anticaugulant. It is also used as potential rodenticide against field and Phytotoxins are secondary metabolites which applied to control microbial pathogens of medical rodents. Coumarin shows antimicrobial activity especially against M. canis and T. plants. Both fungal and bacterial toxins are known as pathotoxins which much ably control mentagrophytes, compounds have shown strong antibacterial activity (Johann et al., 2007). growth of microbes. These are host selective and also repell insects from feeding. These Coumarins also show anti-viral properties and are found effective against Candidiasis. Coumarins phytotoxins are also formed in liquid culture by fungus or bacterium. Phytotoxins are active with a methoxy function at C-7 and present, an OH group at either the C-6 or C-8 position at very low concentrations i.e. 1 X 10-10 mol dm-3. Most phytotoxins have complex structure Journal of Pharmacy Research Vol.4.Issue 4. April 2011 1179-1185 Ravi Kant Upadhyay et al. / Journal of Pharmacy Research 2011,4(4),1179-1185 but are very simple molecules. For example 3-(methyl-thio) panoic acid is produced by the REFERENCES: Cassva pathogen Xanthomonas campestris. It is effective at level of 6 microgram /gm. Most 1. Abdelrahim SI, Almagboul AZ, Omer ME, Elegami A. “Antimicrobial activity of Psidium guajava of phytotoxins are terpinoids, sesquiterpinoid and polyketide based lactones. L.”, Fitoterapia, 73, 2002, 7-8 2. 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Journal of Pharmacy Research Vol.4.Issue 4. April 2011 1179-1185