Hundiwale Jogendra C et al. / Journal of Pharmacy Research 2012,5(4),1924-1929 Review Article Available online through ISSN: 0974-6943 www.jpronline.info A current update on phytopharmacology of the genus Hundiwale Jogendra C.*1, Patil Avinash V. 2, Kulkarni Mohan V. 3, Patil D.A.4 and Mali Ravindra G. 5 1. Dept. of Life Sciences, North Maharashtra University, Jalgaon , Maharastra, India 2. Smt. Sharadchandrika Suresh Patil College of Pharmacy, Chopda, Dist. Jalgaon Maharastra, India 3. Division of Biochemistry, Dept. of Chemistry, University of Pune, Poona, Maharastra, India 4. Dept. of Botany, S.S.V.P. Sanshta’s LK Dr. P.R. Ghogrey Science College, Dhule, Maharastra, India 5. L. B. Rao Institute of Pharmaceutical Education and Research, Shri B. D. Rao College Campus, Khambhat-388 620, Maharastra, India Received on:11-01-2012; Revised on: 17-02-2012; Accepted on:19-04-2012

ABSTRACT The genus Alternanthera, (family: ) is interesting from both pharmacological and phytochemical perspectives. Very few species in this genus have a long history of use in traditional medicinal systems. Alternanthin B, the most important constituent isolated is known to posse’s antitumor activity. Very few additional data are available on the phytochemical and biological activities of pure compounds from Alternanthera. It is tragedy that due to modernization, industrialization and enhanced needs, natural harmony is getting disturbed. It is, therefore, essential to study and conserve them before they become extinct. This paper gives a critical assessment of the literature to date and aims to focus the pharmaceutical potential of the genus that has been underestimated and requires closer attention.

KEY WORDS: Amaranthaceae, Alternanthera, Phytopharmacology, Flavonoids, Saponins 1.INTRODUCTION: Amaranthaceae is a cosmopolitan family consisting of 64 genera and about stigmas; or styles 2 or 3 papillosely stigmatic on the lower face, erect or 800 species, mostly abundant in tropical regions of America, Africa and recurved. Fruit a membranous utricle, rarely a circumscissilely or irregularly India. The Family represented by herbs, few shrubs and a large number of the rupturing capsule, very rarely a berry, enclosed in or supported by the per- amaranthaceous species are ubiquitous weeds [20]. The genus Alternanthera sistent perianth. Seed inverted or erect, orbicular, ovate or reniform, com- an important representative of the family Amaranthaceae was established pressed; testa crustaceous; embryo horseshoe-shaped or annular, surround- by Forsskal in 1775. The genus comprises approximately 80 species which ing a floury albumen. The mostly occur in tropical, subtropical or are widespread in the tropical and subtropical regions of New World. A. temperate regions [28]. philoxeroides has been found to be quite rich in iron content and may be used as salad. This species may also be used for production of methane gas and 2.2 Ethnobotanical studies: tertiary filtration system for domestic sewage. Thus glimpses the nutritional Several species of the genus Alternanthera are widely used in traditional and economical potential of genus. The genus is reported to contain amino medicine and are as summarized in the Table 1. Some of the species from the acids, flavone glycosides, steroids [59], saponins [53], lipids [25], and vita- genus Alternanthera are consumed as wild vegetable also [46] mins [49]. The genus finds potential claims in the viral diseases [7], as an immunomodulator [17], protective against cancer [11], antimalarial [21] and 3. PHYTOCHEMICAL STUDIES: in the treatment of diarrhea [63]. In this paper, a contemporary summary of The chemistry of this genus is complex with wide variety of phytochemical biological, pharmacological and other miscellaneous research on Alternanthera constituents. The genus is enriched with flavonoids and glycosides. Some species is presented and critically evaluated. Amongst the various species, species of the genus reported to contain alkaloids, and several other compo- only six species have been phytochemically investigated. nents including sugars, amino acids, hydrocarbons and steroids. Following are the important phytochemical reports on the various species of 2. ETHNOBOTANY OF ALTERNANTHERA: Alternanthera.

2.1 Botanical Description 3.1 Betaine: are opposite or alternate; stipules O. Flowers are usually hermaphro- Betaine compounds are chemically compatible osmolytes aiding adaptation dite (rarely polygamous or dioecious), small, usually in terminal simple or to saline and dry conditions and it has been demonstrated that applications of paniculate spikes, cymes or clusters (the outer flowers of a cluster some- betaines in low amounts to plants has resulted in significant enhancement of times deformed); bracts hyaline or scarious; never leafy; bracteoles 2, sca- the ability of plants to resists attack by fungi and root knot nematodes [14]. brous. Perianth usually of 5 free or slightly connate hyaline or scarious Glycine betaine produced by wide variety of marine organisms having di- persistent sepals, imbricate in bud. Stamens 1-5, opposite the sepals usually verse effect on the enzymatic reactions of living organisms [48] and also included; filaments usually connate below or united with intervening mem- posses antimicrobial activity [31]. Gerald Blunden and et al examined aerial branous staminodes in a hypogynous cup; anthers 1-, 2- celled. Ovary 1- parts of 23 species distributed in 10 genera of the Amaranthaceae for the celled, ovoid, ellipsoid or lobose; ovules one or more, amphitropous, erect or presence of betaine. Glycine betaine was isolated from all the species studied suspended from short or long free basal funicles; style sometimes simple or and eight out of nine species of Amaranthus revealed presence of trigonelline. obsolete with capitellate or small stigma, sometimes 2-3-fid with acute Amongst nine species two species were from Alternanthera. From the data obtained they have justified classification of Amaranthaceae as a betaine *Corresponding author. accumulating family [14]. Dr. Hundiwale Jogendra C. Smt. Sharadchandrika Suresh Patil 3.2. Flavonoids: College of Pharmacy, Flavonoids are polyphenols that occur universally in dietary and medicinal Chopda-425 107, Dist. plants and exhibit a wide variety of biological activities such as antioxidant, Jalgaon ,Maharastra, India anti-inflammatory, anticancer, antiviral, and antibacterial [22]. A number of flavonoids and flavone glycosides have been isolated and identified from Alternanthera species (Table 2).

Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1924-1929 Hundiwale Jogendra C et al. / Journal of Pharmacy Research 2012,5(4),1924-1929 Table 1: Traditional uses of the various species of genus Alternanthera

Plant resource part used Traditional uses Method of application Reference

A.sessilis Leaves and stems Stomach and gastric problems, Leaves and stems are roasted Jubilee et al. 2006 [24] posse’s antiulcer activity. and taken orally Leaves and shoots Galactagogue,fodder, for night - Mishra S.B. et al. 2008 [37] blindness and increase flow of milk in cattle. Shoots Wild vegetables - Kar and Borthakur 2008 [27] Whole plant Alleviate dementia, to create a - Michael Adam et al. 2007 [36] disease-free youth state and significant vigor Whole plant Diarrhea, leprosy, skin - Dhole et al. 2009 [10] diseases and fever Leaves Stomachache Half Kg of leaves mixed with Shivanna et al. 2009 [54] pepper and salt and fried in ghee. Fried plant material taken orally, daily once for 2-3 days Root, stem and Blood dysentery Decoction is taken twice a day Sunilkumar Sen et al. 2008 [57] Whole plant Blood and skin diseases - Hemen Sarma et al. 2008 [18] Whole plant Growth of hair and Juice of plant Mithun Sikdar, et al. 2008 [38] induces lactation in women Leaves Eye diseases Periodical consumption Ramarao, et al. 2005 [45] of leaves A. pungens Whole plant Measles Paste is applied externally Kamal Elkhalifa et al. 2006 [26] Aerial parts Against grippes, headache An infusion is prepared with a Agra et al. 2007 [1] and abdominal pain handful of fresh plant in one liter of water Inflorescences As vermifuge A spoonful decoction in a cup Agra et al. 2007 [1] of water drunk before breakfast once a day A. dentate Aerial parts Anti-inflammatory, analgesic - Beatriz et al. 2006 [6] and antibiotic A. tenella Colla Aerial parts Diuretic - Beatriz et al. 2006 [6] Leaves Diuretic, anti-pyretic, antiseptic of An infusion of a spoonful in a Agra et al. 2007 [1] urinary tract and against gripes cup of water. Drunk as tea Roots Amenorrhea, inflammations, A decoction of handful of roots Agra et al. 2007 [1] ovarian diseases, and in treatment in one liter of water. It is drunk of female sterility as water. A. brasiliana Inflorescences In treatment of colds and grippes, An infusion of a spoonful in a Agra et al. 2007 [1] headaches and as expectorant cup of water Leaves Antipyretic An infusion of a spoonful in Agra et al. 2007 [1] a cup of water Roots Diarrhea Decoction of fresh roots Agra et al. 2007 [1] in a cup of water Aerial parts Antimicrobial Aqueous extract Gilsane, et al. 2008 [15] A. philoxeroides Whole plant Influenza Syrup International conference proceedings, 1991 [41] Whole plant Vegetable - Rahman et al. 2007 [44] A. porrigens Leaf and flower Hepatic pain, Influenza, Aqueous infusion Omar Malagon et al. 2007[39] Kidney problems A. repens Whole plant Vegetable - Bye et al.1990 [47] A. bettzickiana Whole plant Wild edible - Arinathan et al. 2007 [5]

Table 2: Flavonoids and related compounds from the genus Alternanthera No. Compounds Plant resource Reference

01 Alternanthin A. philoxeroides Bing-Nan Zhou et al 1988 [7] 02 Vitexin, Isovitexin, 2”-O-*-L- rhamnopyrosylvitexin, 2”-O-b-D Aerial parts of A. maritima Salvador et al 2004 [35] glucopyranosylvitexin, Isorhamnetin-3- O-robinoside, Isorhamnetin-3- O- rutinoside, Kaempferol, Quercetin-3-methyl ether 03 Acacetin-8-C-[a-L-rhamnopyranosyl-((1g2)-b-D-glucopyranoside)], 2”- Ethanolic extract of A. tenella colla Salvador et al 2006 [51] O- a-L-rhamnopyranosyl-vitexin, 2”- O -b-D-glucopyranosyl-vitexin, Vitexin, Quercetin, kaempferol

OCH OCH3 3 OH OR 2

OR O HO O 2 OR 3 CH3 O OH CH3 O H H H H H H H H H OR 1 O H H OR 3 H OH O OH 1 R1 = R2 = R3 = H 2 R1 = H, R2 = R3 = Ac 3 R1 = R2 = R3 = Ac Figure 1: Novel Alternanthin from A. philoxeroides 4 R1 = R2 = Me, R3 = H

Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1924-1929 Hundiwale Jogendra C et al. / Journal of Pharmacy Research 2012,5(4),1924-1929 3.3. Saponins: 3. 5. Other Phytoconstituents: Saponins are steroid or triterpenoid glycosides found in plants and plant Besides this, many other phytochemicals have been isolated. Following is a products. Several biological effects have been ascribed to saponins such as brief account of these miscellaneous phytochemicals. Fang et al [12] isolated membrane-permeabilising, immunostimulant, antioxidant, hypocholestero nine chemical constituents from Alternanthera philoxeroides and identified laemic, hypoglycemic, and anticarcinogenic properties. These compounds as phaeophytin a (1), phaeophytin a (2), oleanoic acid (3), beta-sitosterol have also been observed to kill protozoa and molluscs. They also impair the (4), 3 beta-hydroxystigma-5-en-7-ones (5), alphamethylenecycloartanol (6), digestion of protein and vitamins and mineral uptake in the gut. They also cycloeucalcenol (7), phytol (8) and the structures were elucidated by spec- have antifungal and antiviral activity [30]. Triterpene also found to exhibit troscopy. Jin-Bo Fang et al [11] isolated alternanthin B and N-trans-feruloyl- anti-HIV reverse transcriptase activity [50]. Sanoko et al isolated four new 3, 5-dimethoxytyramine and other four compounds from the aerial parts of triterpene saponins from the methanolic extract of the aerial parts of Alternanthera philoxeroides (Figure 3) and evaluated antitumor activity of Alternanthera repens (Figure 2). Their structure have been elucidated using the isolated compounds NMR techniques as 2 *, 3 b- di hydroxyurs- 12, 20 (30)- dien- 28- oic acid OR 3- O- { O- b- D- glucopyranosyl – (1g2)-O- *- L- arabinopyranosyl- HO O (1g2)-O-[ b- D-xylopyranosyl-(1g3)] b- D- glucopyranoside}; 2 *, 3 b- di OH hydroxyurs- 12, 20 (30)- dien- 28- oic acid 3- O- {O- b- D- quinovopyranosyl H C 3 O – (1g2)- O- *- L- arabinopyranosyl-(1g2)- O-[ b- D-xylopyranosyl-(1>3)] HO 1 R = H b- D- glucopyranoside}; 2 *, 3b- di hydroxyurs- 12, 20 (30)- dien- 28- oic OH O 3 R = Me acid 3- O- { O- *- L- arabinopyranosyl – (1g2)-O- [b- D-xylopyranosyl- OH (1g3)] b- D- glucopyranoside}; 2 *, 3 b- di hydroxyurs- 12, 20 (30)- dien- 28- oic acid 3-O- {O- b- D- xylopyranosyl – (1g3)- b- D- glucopyranoside}. R 1

Compound 1-4 were purified by a Sephadex LH-20 column and RP HPLC R 2 O from the methanol extract [53]. . H 3CO N R 3 H . R1 R2 R3 H O 2 OMe OH OMe 4 OMe OH H . . COOH 5 H OH H OH HO O . OH HO O O OR O O . . H CO N HO 3 OH H HO OH OH HO O . Figure 3: Alternanthin B and selected compounds from A. philoxeroides O . HO 1 R = HO 2 R= . O O Ragasa et al [43] reported that the chloroform extract of the air dried leaves of OH O O HO Alternanthera sessilis afforded a mixture of diasteriomers of new ionone HO OH derivatives (Figure 4), whose structures were elucided by spectral analysis. HO HO OH The mixture of diasteriomers showed low antimicrobial activity against Pseudomonas aeruginosa and Trichophyton mentagrophytes. O H 3 R= 4 R = H O . O . H O O H CH OH 2 CH3 Figure 2: Novel triterpene saponins from A. repens OH . . R R' . . 3. 4. Lipids and vitamins: O Kallappa M. Hosamani et al [25] reported that Alternanthera sessilis (Linn) 1 a R = H, R’ = OH R.Br. seed oil contains a moderate source of hydroxyl fatty acid (ricinoleic 1 b R = OH, R’ = H O acid, 22.1%), along with the other normal fatty acids such as myristic (3.9%), palmitic (16.9%), stearic (5.9%), oleic (26.0%), and linoleic (25.2%). These fatty acids have been determined and characterized by GLC, TLC, UV, FTIR H 1 13 (Fourier Transform Infrared), H NMR, C NMR, MS and chemical trans- . . formations [25]. O Shridhar and Lakshminarayana [49] studied the lipid classes, fatty acids, and Figure 4: Novel Ionone derivatives from A. sessilis tocopherols of leaves of six edible plant species. Young leaves of Tamarindus Souza et al [56] isolated two O-glycosides and three C-glycosides from indica, Oxalis corniculata, Rumex vesicularis, Alternanthera sessilis, butanolic fraction of crude ethanolic extract prepared from aerial parts of Trigonella foenumgraecum and Talinum triagulare respectively yielded, 1.16, Alternanthera maritima and studied the effect against human PMNLs. 1.47, 0.47, 0.54, 1.50, and 2.42% lipids (dry weight) on extraction with chloroform-methanol. According to them leaves of A. sessilis contained good Gowik et al [16] isolated phosphoenolpyruvate carboxylase (PEPCase) amounts of a-tocopherol (22mg of dry weight) and ß-tocopherol (6.22mg of cDNAs from the C (4) plant Alternanthera pungens H.B.K., the C (3) / C (4) dry weight).

Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1924-1929 Hundiwale Jogendra C et al. / Journal of Pharmacy Research 2012,5(4),1924-1929 intermediate plant A. tenella colla, and the C (3) plant A. sessilis (L.) R.Br. of-way. This study utilized floating and rooted plant species in hydroponic and investigated the kinetic properties of the corresponding recombinant solution to monitor the uptake of trace levels of the herbicide from an aque- PEPCase proteins and their phylogenetic relationships. Phosphoenolpyru- ous concentration of 24 µg/ml. The four plant species evaluated included vate carboxylase (PEPCase) is a key enzyme of C (4) photosynthesis. Ge- Eichhornia crassipses, Alternanthera philoxeroides, Hydrophila lacustris nomic southern blot experiments and sequence analysis of the 3’ untranslated and Lemna minor. This study proved the bioaccumulation of herbicide regions of genes indicated the existence of PEPCase multigene family in all MSMA in four plant species. three plants. Chen et al [9] reported that the Chinese crude drug “Han-lian-cao”, in Taiwan was derived from the entire plant or aerial part of Eclipta prostrate L. and Xinhui Bi et al [61] presented molecular composition and compound-spe- Alternanthera sessilis R. Brown. cific carbon and hydrogen stable isotope ratios of leaf wax h-alkanes for 26 species utilizing C3, C4 and CAM photosynthetic pathways. They included Rajput and Rao [29] achieved secondary growth in Achyranthes aspera, Alternanthera bettzickiana (Regel) Nicols, ‘Rubiginosa’, Alternanthera polygamous, Alternanthera pungens, Alternanthera sessilis and Alternanthera versicolor Regel species from the genus Alternanthera for and Alternanthera triandra by the development of a cambial variant resulting their studies. in successive rings of xylem and phloem. Each new cambium was developed at a distance about to three cells external to the phloem produced by the 4. PHARMACOLOGICAL ACTIVITIES: previous cambium. Development phloem and xylem was not synchronous. The various traditional and clinical uses of Alternanthera for the treatment of They noticed that phloem mother cells differentiated in to sieve tube ele- various disorders have been given some validation by modern pharmacologi- ments, companion cells and axial parenchyma. On the other hand xylem was cal studies. The various pharmacological activities of the genus are shown in composed of axial elements with absence of radial elements in all xylem rings Table 3 of stem. They occasionally observed vessels as radial and tangential mul- Table 3: Pharmacological activity of the genus Alternanthera. tiples. Sr. No. Name of the Extract Utilized Pharmacological activity Patil and Shrivastava utilized [40] A. bettzichiana plant mate- Alternanthera sp. 01 A. philoxeroides Petroleum ether and ethyl acetate Antiviral effect [62, 42] rial adsorbent for the removal Cr 02 A. pungens Ethanolic Diuretic activity [8] (VI) from aqueous solutions due 03 A. brasiliana Hydroalcoholic extract of aerial parts Analgesic activity [34] to easy availability and low cost. 04 A. lanceolata Ethanolic Antimalarial activity [21] 05 A. repens Hexane, Chloroform, methanol and aqueous extracts Antidiarrhoeal activity [63] Batch adsorption studies dem- 06 A. brasiliana Callus culture Extract Antinociceptive effects [33] onstrate that the adsorbent pre- 07 A. pungens, A. tenella, Leaf extracts Immunological reactivity [13] pared from A. bettzichiana A. hypochondrachus, A.sessilis 08 A. sessilis Chloroform extract of leaves Antimicrobial activity [43] (Regel) Nicols plant material 09 A. tenella Colla Aqueous extract Immunomodulatory property [17] (ABPM) has significant capac- 10 A. repens Crude extract of whole plant Antiprotozoal activity [58] ity for adsorption of Cr (VI) 11 A. maritima Ethanolic extract of aerial parts and roots Antimicrobial activity [52] 12 A. pungens and A. sessilis Whole plant extract in equal volume pet ether Nutritional value [60] from aqueous solution. They in- and aqueous sodium chloride (25%w/v) cluded pH, contact time, adsorp- 13 A. philoxeroides Petroleum ether extract Antiviral and cytotoxicity Studies [23] tion dosage and initial Cr (VI) 14 A. sessilis Ethanolic extract Antioxidant activity [55] 15 A. philoxeroides Ethanolic extract of aerial part Antitumor activity [11] concentration parameters for in- 16 A. sessilis Ethanolic extract Diuretic activity [3] vestigation. The adsorbent pro- 17 A. tenella Hot and Cold aqueous extracts Immunomodulatory and anti-inflammatory effects [32] cess of Cr (VI) was tested by using Langmuir and freundlich 5. TISSUE CULTURE STUDIES: models. Macedo et al [33] established callus cultures of 7. CONCLUSIONS using 2, 4-D as a growth regulator in media. The extracts prepared from callus The world has now been immeasurably fascinated by the medicinal and their cultures exhibited antinociceptive effects in mice and seems to be more effec- miraculous results in all respects. Critical assessment of literature to date and tive than the plant extracts. They concluded that pharmacological action is aims to show that genus and its pharmaceutical potential has been underes- due to the presence of steroids and / or terpenes. timated. Actually, it requires attention at microscopic level. Genus is counted to be a type of weed and the weeds are defined to, “a plant whose virtues Alveera Singh et al [2] developed micropropagation protocol for Alternanthera have not been yet discovered and a plant in wrong place.” This reflects sessilis using leaf explants. They utilized different concentrations and com- negative nature of weeds. The persona from the medical world runs after binations of auxins and cytokinins for callus formation, shoot regeneration, those plants who have been seated in the range of medicinal plants. But, the and root formation. According to them MS medium supplemented with 1mg/ plants which have already been named weeds can occupy unparallel place in l BAP and 1mg/l 2, 4-D was found to be suitable for callus induction and 1mg/ the natural components of the environment by carving their roles, Jimson l IAA and 1mg/l BAP concentration for shoot multiplication. weed (Datura stramonium) for instance.

Hundiwale et al [19] developed simple and efficient micropropagation pro- The genus Alternanthera is enriched with flavonoids, saponins, vitamins, tocol for Alternanthera bettzichiana using shoot tips and apical meristem as glycosides and other secondary metabolites. Clearly, members of the genus explants. Alternanthera posse’s significant pharmacological potential and promising activities of the extracts in the context of ethnomedicinal knowledge, espe- 6. MISCELLANEOUS STUDIES: cially in the field of anti-inflammatory, immunomodifying, antitumor, anti- Anderson et al [4] screened four vascular aquatic plants for uptake of mono- bacterial etc. The Ayurveda have already recognized Alternanthera pungens, sodium methanearsonate (MSMA). MSMA is used extensively for weed Alternanthera sessilis, and Alternanthera philoxeroides as landmarks. With control in non-edible crops and for chemical mowing along roadside rights- only a few exceptions, the pharmacological studies have focused mainly on

Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1924-1929 Hundiwale Jogendra C et al. / Journal of Pharmacy Research 2012,5(4),1924-1929 crude extracts, and many of phytoconstituents with its putative mechanisms Amaranthaceae, Biochemical systematics and Ecology, 27 (1), responsible for different pharmacological actions, remain unknown. The col- 1999, 87-92. lected information provides a resource for future characterization of the 15. Gilsane L, Von Poser, Cesar Avancini, Jose M Wiest, Rodrigo Dall genus Alternanthera in terms of ethno pharmacological, phytochemical and Agnol, and Juliana Schulte Haas, Antimicrobial activity of plants biological standards. used in the prevention and control of bovine mastitis in Southern , Lat. Am. J. Pharm, 27(6), 2008, 894-899. 8. ACKNOWLEDGEMENT: 16. 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Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1924-1929