Shirish S. Pingale et al. / Journal of Pharmacy Research 2012,5(2),1076-1082 Review Article Available online through ISSN: 0974-6943 http://jprsolutions.info Recent Developments in Research of Celocia Argentea: A Review

Shirish S. Pingalea*, Sunita Salunke-Gawalib, Anil G. Markandeyac and Narayan P. Firkec a *Department of Chemistry, ACS College, Narayangaon, Pune 410 504, India bDepartment of Chemistry, University of Pune, Pune 411 007, India c Department of Chemistry, Fergusson College, Pune 411 004, India Received on:10-11-2011; Revised on: 15-12-2011; Accepted on:12-01-2012

ABSTRACT We herein report the recent developments of Celocia argentea research. Asian origin Celocia argentea is belongs to family and commonly known as Cockscomb. This weed spread in all the continents with major as Asia and Africa. The is also reported as crop for leafy vegetable. Natural and abundant availability of Celocia argentea draw scientist’s attention towards its various applications. The plant is enrich with natural products as carbohydrates, lipids, amino acids, peptides, phenols, phenolic acids, flavonoids, terpenes, terpenoids, steroids, alkaloids which includes celogenamide A, celogentin, A–D, H, J and K, moroidin, celosian, citrusin C, cristatain, nicotinic acid, betalains, amaranthin, isoamaranthin, betalamic acid, miraxanthin V (Dopaamine-BX), 3-methoxytyramine-BX and (S)-Tryptophan-BX. The plant is well known as traditional medicine for diarrhea, bleeding piles, bleeding nose, cold, gastrointestinal diseases, gonorrhea, jaundice, fever, haematological, gynecological, uterus disorder, rheumatoid arthritis, sores, ulcers, skin eruptions, snakebite and as an abortifacient. Whereas it is also reported for its pharmacological activity such as antioxidant property, anti-diabetic activity, antihepatotoxic activity, antiviral activity, anti-inflammatory activity, antimitotic (antitumor) activity, wound healing activity, anti-microbial activity and skin depigmentation. The plant is patented for its cosmetic applications such as skin whitening agent. Celocia argentea is recognized as biosorbents and fertilizer. This review highlights recent and almost all the components associated with Celocia argentea.

Key words: Amaranthaceae, Pharmacology, Betalains, Celogenamide, Celogentins. INTRODUCTION

An Indian origin, Celocia argentea, (Synonyms: argentea; Semen celosiae) (Family: Amaranthaceae) commonly known as cockscomb, is a plant of tropical origin and known for its very brilliant colors [1]. Plant grows as a weed during the rainy season throughout Asia, Africa and America. Plant bears simple and spirally arranged leaves, often pinkish or white flowers while fruits are globular and seeds are black[2]. Genetic diversity of 16 populations of Celocia argentea and 6 populations of Celocia cristata L. was investigated in China using sequence-related amplified polymor- phism (SRAP)[3]. Celocia argentea var. Cristata (L) along with like Aerva lanata (S), Alocasia macrorhiza (L), Ammania baccifera (L), Asparagus racemosus (S), Celocia argentea var. Cristata (L), Chlorophytum bharuchae (L), Commelina forsskalaei (WP), Digeria muricata (L), Glinus oppositifolius (WP), Gnaphalium pulvinatum (L), etc. are routinely used as leafy vegetable[4]. The taxonomical hierarchy of Celocia argentea is as follows: Kingdom: Plantae Super division: Spermatophyta Division: Magnoliophyta Class: Magnoliopsida Order: Carypphyllales Figure 1. Celocia argentea (Cockscomb) Family: Amaranthaceae Genus: Celocia Celocia argentea, whole plant is known for its used in treatment of diar- Species: C. argentea L. rhea, piles, bleeding nose, disinfectant, inflammation, haematological and gynaecologic disorders[5]. In India, the plant is well known for treatment of mouth sores, blood diseases and used as an aphrodisiac[6]. *Corresponding author. Dr. Shirish S. Pingale Recently, the three novel triterpenoid saponins, celosin E, celosin F and Head, PG Department of Chemistry, celosin G together with a known compound cristatain, were isolated from Gramonnati Mandal’s Arts, the seeds of Celocia argentea (Amaranthaceae) and characterized using Commerce and Science College, extensive NMR and MS technique. The antitumor and anti-inflammatory Narayangaon, (Affiliated to University activities of the four compounds were tested in vitro[7]. Phytochemical of Pune),Pune - 410 504, [8] Maharashtra, India. analysis of Celocia argentea reveals betalains , nicotinic acid, celogenamide A[9], celogentin A–D, H, J[10] and K[11], moroidin[12]. The inflorescence of Celocia argentea has been studied for the removal of methylene blue from wastewater as cheap and eco-friendly biosorbents. Inflorescence of Celocia argentea along with stem of Cicer aritinum and cob of Zea mays was used

Journal of Pharmacy Research Vol.5 Issue 2.February 2012 1076-1082 Shirish S. Pingale et al. / Journal of Pharmacy Research 2012,5(2),1076-1082 in the batch adsorption study with variation of amount of adsorbent, con- (0.02%) isolation yield has reported[12]. Celogenamide A 7, a cyclic peptide centration, temperature and pH. Inflorescence of Celocia argentea found from the seeds of Celocia argentea has been isolated and characterized to be effective for removal of methyl blue up to 76% for 0.125 gm of using 2D NMR and MS-MS. The seeds of Celocia argentea were crushed adsorbent at pH 8 to 10[13]. There is budding interest in the Celocia argentea and extracted with methanol and purified with column chromatography for its phytochemical constituents and the pharmacological activity. followed by C18 HPLC (CH3CN-0.1% CF3CO2H, 3:7) affords Celogenamide A 7 (0.0002%)[9]. Recently, the total synthesis of celogentin C has been 1.PHYTOCHEMICAL CONSTITUENTS achieved in 23 steps starting from simple amino acid building block. Effi- cient palladium-catalyzed C-H functionalization strategy was employed 1.1.Primary Metabolites to construct the key Leu-Trp linkage of this bicyclic compound[16]. Primary metabolites are the substances responsible for development, growth and reproduction in living organisms. These make energy available for anabo- H N NH2 lism and catabolism. Carbohydrates, proteins and vitamins are the often O found in living organisms. O H H N O NH N N H H 1.1.1.Carbohydrates O HN Carbohydrates are the polyhydroxylated aldehydes and ketone, which are NH CO R O N 2 apparent result of photosynthesis. Sucrose as a carbohydrate, disaccharide O N has been accounted along with b-sitosterol[14] in seeds of Celocia argentea N N which serves as storage of energy. HN H H O 1.1.2.Lipids 4 lipids occur in a plant on the surfaces, which are responsible for membrane integrity and energy storage. Lipids consist of fatty acids, waxes, Celogentin A 4: R=H glycerides, phospholipids, sterols, vitamins A, D, E and K. Celocia argentea Celogentin B 5: R=His has been found to consist of b-sitosterol 1, palmitic acid and stigmasterol 2, Celogentin D 5a: R=His-Lys daucosterol 3 and oleanolic acid[14]. H2N NH O HN O H H N H N H N HN H H O H O O NH NH H H O N H H 2 O HO N COOH HO 1 N N HN H Stimgasterol H b-Sitosterol O 6 Celogentin C H OH

H H O Me Me O O H OH N N H O H N N 3 N H HO O N OH O O O OH HN H NH N Daucosterol O O O 1.1.1.Amino Acids, Peptides and Protein NH HO Amino acids are molecules containing an amine group, a carboxylic 7 acid group and a side-chain that varies between different amino acids; these HOOC are the basic unit of proteins and peptides. Amino acids are the building Celogenamide A blocks of metabolic processes. Amino acids mostly are water soluble and present apart as peptide in the plant tissue are known as free amino acid, NH2 these are indicator of physiological and health status of the plant. Seed of Celocia argentea has been analysed for protein contain and found to have 18 kinds of amino acids, of which 8 kinds are essential amino acids. Celogentin K 8, a cyclic peptide proved by NMR, MS-MS and CD spectra from the seeds of Celocia argentea has been reported. The seeds of Celocia In 2001, the novel bicylic peptides, celogentins A 4, B 5, C 6 were isolated argentea were extracted with methanol and subjected to amino silica gel with known moroidin from the seed of Celocia argentea. The structures of column (Diaion HP-20) for separation followed by C18 HPLC affords newly isolated compounds were unambiguously proved by NMR and chemi- celogentin K 8 (0.00002 % yield). Moroidin 9 isolated from seeds of Celocia cal means. These compounds are found have inhibition activity against argentea was crystallized from methanol–water as colorless needles, de- polymerization of tubulin[15]. The Celogentins A 4 (0.0002% yield), B 5 compose at 280 0C. The structure of Moroidin 9 was proved unambigu- (0.0001%), and C 6 (0.001%) as colorless solids together with moroidin 9 ously by single crystal X-ray diffraction[11].

Journal of Pharmacy Research Vol.5 Issue 2.February 2012 1076-1082 Shirish S. Pingale et al. / Journal of Pharmacy Research 2012,5(2),1076-1082

H N NH2 O O H H N NH N N HN H H NH HN O O NH OH H N C O O H O O H O O NH H2N COOH H N N H HN N H H CO2H 12 O HN (S)-Tryptophan H O O C N CO O H 8 H Celogentin K 1 3 (S )- T ry p to p ha n B e ta xan thin 2 R H3CO H N NH 2 O N O H H HO N N H N N H H N H H O O N H O O O N N N H HOOC N COOH N N H H N H H C OOR 1 O 14 9 3-Methoxyramine-Betaxanthin

M oroidin 9: R 1=R 2= H 1.1.Secondary Metabolites C elogentin E 9a: R 1= Asp, R 2=H C elogentin F 9b: R 1= Arg, R 2= H 1.1.1.Phenols and Phenolic acid C elogentin G 9c: R 1=H , R2 =M e Phenols and phenolic acids are the secondary metabolites which are syn- C elogentin H 9d : R1= As p, R 2=M e thesized from carbohydrates. The six compounds including Eugenyl O-b- C elogentin J 9e: R1 =A rg, R 2= M e D-glucopyranoside (citrusin C) were isolated from the leaves of Celocia argentea which shows Tyrosinase inhibitory and superoxide scavenging The six bicyclic peptides, celogentins D 5a, E-H (9a-9d) and J 9e have been activity[18]. isolated from the seeds of Celocia argentea. The usual chromatographic separation yields Celogentins D 5a (0.00004%), E 9a (0.0008%), F 9b The six compounds isolated from the leaves of Celocia argentea 1-(4-O-b- (0.001%), G 9c (0.0007%), H 9d (0.00004%), and J 9e (6, 0.00003%) as glucopyranosyl-3-methoxyphenyl) propan-2-ene (citrusin C 15), 3-O-b - colorless solids together with celogentins A–C (4-6) and moroidin 9. The glucopyranosyl-1H-indole (indican 16), (7E)-6,9-dihydromegastigma-7-ene- structure of these peptides were analysed by NMR, Celogentins E-H (9a- 3-one-9-O-b -glucopyranoside 17, (3Z)-hexenyl-1-O-(6-O-ß - 9d) and J 9e showed potent inhibition of tubulin polymerization[10] . rhamnopyranosyl-b-glucopyranoside) 18, (3Z)-hexenyl-1-O-b-D- glucopyranoside 19 and trans-ferulic acid 20. Among the found compound 1.1.1.Betalain (citrusin C 15) showed good skin depigmentation effect[18]. A phenolic Betalains are water soluble pigments which comprise red-violet betacyanins glycoside, 4-O-b-D-glucopyranosyl-2-hydroxy-6-methoxyacetophenone 21 and yellow betaxanthins. Surprisingly they are also found in higher fungi. along with known compounds, 4-O-b-D-apifuranosyl-(1®2)-b-D- Betalains are vital as food colouring and their antioxidant for protection glucopyranosyl-2-hydroxy-6-methoxyacetophenone 22, eugenyl-O-b-D- against oxidative stress[17]. The betalains of red, orange and yellow inflores- glucopyranoside 15, sucrose, quercetin-3-O-b-D-glucopyranoside 23, cences of common Cockscomb (Celocia argentea var. Cristanta) were com- isorhamnetin-3-O-b-D-glucopyranoside 24, rhamnatin-3-O-b-D- pared and found to be qualitatively identical to that Celocia argentea var. glucopyranoside 25, isorhamnetin-3-O-ß-L-rhamnopyranosyl-(1® 2)-b- Plumosa. Along with betacyanins occurring in yellow inflorescences a dopam- D-glucopyranoside 26, b-sitosterol 1, stigmasterol 2, stigmasterol-3-O-b- ine-derived betacyanins, 2-decscarboxyl-betanidin was ascertained. These D-glucopyranoside 27, were isolated from the plant Celocia argentea[19]. betalains were Amaranthin, Isoamaranthin, Betalamic acid 10, Miraxanthin V (Dopaamine-BX) 11, (S)-Tryptophan 12, (S)-Tryptophan-BX 13, 3- OH methoxytyramine-BX 14; The comparison study were carried out by HPLC- O PDA and Mass spectrometry[8]. HO O HO O OH 15 HO H3CO H Eugenyl-O-b-D-glucopyranoside (citrucin C) HO N H H N OH HOOC N COOH H O 10 H O OC N COOH HO Betalamic acid H HO O 11 OH 16 M iraxanthin V 3-O-b-glucopyranosyl-1H-indole (indican)

Journal of Pharmacy Research Vol.5 Issue 2.February 2012 1076-1082 Shirish S. Pingale et al. / Journal of Pharmacy Research 2012,5(2),1076-1082

OH O

O H HO O HO OH 17 H OH OH H H (7E)-6,9-dihydromegastigma-7-ene-3-one-9-O-b-glucopyranoside HO O O 27 HO OH OH Stigmasterol-3-O-b-D-glucopyranoside O O 18 1.1.1.Flavonoids OH Flavonoids are large groups of phenolic plant constituents containing two OH O benzene ring joined by oxygen containing pyrene ring. Flavonoids play an HO O HO important role in a plant as a defense and signaling compounds in reproduc- OH tion, pathogenesis and symbiosis. Several classes of flavonoids were re- ported for their antiproliferative activity against human cancer cell. The (3Z)-hexenyl-1-O-(6-O-b-L-rhamnopyranosyl-b-D-glucopyranoside) two isoflavones, 5-Methoxy-6,7-methylenedioxy-2'-hydroxyisoflavone 28 OH and its 2'-methoxy derivative: tlatlancuayin 29 were isolated from aerial parts of Celocia argentea[20]. HO O O O O OH O HO O OMe OH 19 O O (3Z)-hexenyl-1-O-b-D-glucopyranoside O O O O 29 OH OH OH 28 5-Methoxy-6,7-methylenedioxy-2'-hydroxyisoflavone Tlatlancuayin OCH3 O HO O COCH3 HO 1.1.Metabolites- Isoprenoids OH 20 21 OCH 3 1.1.1.Diterpenes 4-O-b-D-glucopyranosyl-2-hydroxy-6-methoxyacetophenone Diterpenes, C20 are a group of compounds that consists of 4 five carbon COOH (C5) units called isoprene. These compounds are well known for their pharmacological, toxicological activities and bitter taste. Gibberellic acid 30 OH OH trans-ferulic acid is a simple gibberellin, a tetracyclic diterpene acid and acts as plant hor- O mone. Similar effect was observed for promoted seedling by oligogalacturonic HO O COCH3 HO acids[21]. O O OH OCH HO O 3 22 CO CH2 OH OH HO 4-O-b-D-apifuranosyl-(1® 2)-b-D-glucopyranosyl-2-hydroxy-6-methoxyacetophenone COOH 30

OH Gibberellic acid OCH3 HO HO 1.1.1.Steroids Phytostreroids represents a wide range of polarities especially, in account O OH O OH OH OH of its existence of polar, non-polar conjugates and the possibility of charged forms. Steroids contain a specific arrangement of four cycloalkane rings HO O O HO O O that are joined to each other. These rings are named as A, B, C and D vary HO O OH HO O OH by functional groups. Steroidal saponins are close with triterpenoid sa- OH 23 OH 24 ponins and broadly distributed in secondary metabolites of plant, marine organism. The definition of saponins is derived based on their surfactant or Quercetin-3-O-b-D-glucopyranoside Isorhamnetin-3-O-b-D-glucopyranoside detergent properties. Steroidal saponins, Cristatain 31, with four other saponins, Celosin A 32, B 33, C 34, D 35 were isolated from the seeds OCH3 OH [22] HO of Celocia cristata . The structures of celosin A 32 and celosin B 33 were HO determined by 1D and 2D-NMR spectral analysis[14,23]. O OH OH O OMe OH O The newly isolated celosin E 36, celosin F 37, celosin G 38 and cristatain 31 HO O from seeds of Celocia argentea were identified and characterized by NMR OHHO O OH HO O O O O and MS technique. Dried Semen celosiae was ground to a coarse powder HO O OH 26 and extracted with 50% ethanol at room temperature and subsequently OH 25 OH subjected to column chromatographic separation yields Celosin E 36 (15 OH mg), Celosin F 37 (18 mg), Celosin G 38 (13 mg) and Cristatain 31 (10 mg) Rhamnetin-3-O-b-D-glucopyranoside [24] Isorhamnetin-3-O-b-L-rhamnopyranosyl-(1®2)-b-D-glucopyranoside for 10 Kg of starting dried material .

Journal of Pharmacy Research Vol.5 Issue 2.February 2012 1076-1082 Shirish S. Pingale et al. / Journal of Pharmacy Research 2012,5(2),1076-1082

O

COOH O H HO O H O O HOOC H O C O O H O O H HO O HO CHO O H OH 31 COOH O HO O Cristatain H O HOOC O O HO O O O H HO CHO 32 OH H O O C O H H O O O O O H O O H 38 HO Celosin A OH C e losin G 1.NUTRITIONAL VALUE

1.1. Vitamins Vitamins are the organic compounds required in tiny amount by an organ- COOH ism. The word vitamin is derived from vital (means important). Most of the HO vitamins are not synthesized by human body and are obtained from the HOOC diet. The vitamin C, L-ascorbic acid exhibits a remarkable biological activity O HO O O as antioxidant and protects the body against oxidative stress. HO CHO 33 OH OH O O Fresh edible green leaves of Celocia argentea, Amaranthus hybridus, Celosin B H O HO C O O H Solanum nodiflorum, and Corchorus olitorius were studied for their chro- OH nological content of vitamin C. The steam-blanched and dehydrated veg- O H etable leaves retain almost all vitamin C. While 0.05% of sodium sulfite/ 3 4 O [25] [26] O sodium metabisulfite and household refrigeration significantly enhanced the retention of ascorbic acid in the processed leaves. The fresh and welted O O O H leave of Celocia argentea after steam cooked and variation in the food O O H preparation found loss in the content of vitamin C[27,28]. C e l o si n C O H H O O H C OOH 2.ETHNOPHARMACOLOGY In Aravalli hills of Rajasthan, the seed paste of Celocia argentea used to OH cure ovarian and uterine diseases[29,30]. Crude alcoholic extracts of Datura O O alba and Celocia argentea leaves were studied against pathogens isolated O from infected burn patients by disc-diffusion method and results show the OH extract of Datura alba having two fold antibacterial activity than Celocia O OH OH argentea as compared with silver sulphadiazine ointment[31]. Celocia OH HO O argentea widely used in Indian folk medicine for the treatment of diabetes O H O mellitus[32]. O H 35

C elosin D COOH In China, Celocia argentea (Amaranthaceae) is well known for cold, gas- HO trointestinal, diseases, gynecological diseases, rheumatoid arthritis[33] and HOOC as fertility regulating agent[34]. The traditional Yao communities of China O HO O use the stem, leaf, flower and seed of Celocia argentea for the treatment of HO COOH 36 hemorrhoids, leucorrhea, profuse uterine bleeding[35]. OH In USA, midwifery, rural Honduras practice Celocia argentea for encour- Celosin E aging lactation and its decoction for hemorrhage[36]. In Riau province, Sumatra (Indonesia) antibacterial assay of extracts of 114 species were tested and Celocia argentea was found to have activity against cough and jaundice[37]. In Vietnam, Celocia argentea plant is used as hemostatics herbal[38]. In screening of Taiwanese crude flower extract of Celocia argentea was found antibacterial activity against Streptococcus mutants[39] Celocia argentea as reported to have activity against snakebite[40]. COOH COOH HO 3.PHARMACOLOGY

O HO O 3.1.Anti-oxidant Activity HO COOH 37 The antioxidant property of Nigerian green leaves was studied with evalu- OH ation of total phenol and L-ascorbic acid content of the species. The study includes plant such as 22 other plants along with Celocia argentea, the Celosin F spectrophotometry method was adopted for evaluation of polyphenols as

Journal of Pharmacy Research Vol.5 Issue 2.February 2012 1076-1082 Shirish S. Pingale et al. / Journal of Pharmacy Research 2012,5(2),1076-1082 [41] Tannic Acid Equivalent (TAE) and ascorbic acid . GC-MS studies showed compounds, stigmasterol 2 showed fair inhibitory activities against SGC- that caffeic acid was absent in Celocia argentea and Talinum triangulare [19] [42] 7901 and BEL-7404 cells . Recently, Kobayashi group demonstrate among the studied plant . The aqueous extract of Celocia argentea leaves Celogentin C 6, the only family member to possess a proline residue in its attenuated Cd-induced oxidative stress in the animals, with the best result right-hand ring and exhibits the greatest potency (IC 0.8 µM), against at 400 mg kg-1 body weight. The action of extract as scavenging of free 50 known anticancer agent vinblastine (IC 3.0 µM). While the Moroidin 9 [12] radicals accounts for the action as an antioxidant[43]. The Betalains isolated 50 from family Celocia argentea and other species of Amaranthaceae are known and moroidin-type compounds, Celogentins E-H (9a-9d) and J 9e, are roughly equipotent with vinblastine (IC 2.0-4.0 µM) and substantial for antioxidant and radical scavenging properties for protection against 50 [10] [17, 44, 45] activity by celogentins A 4 , B 5, and D 5a (IC 20-30 µM) . A new cyclic certain stress–related disorders . 50 peptide with a 3-hydroxyoxindole ring, Celogentin K 8 isolated from the 3.2.Anti-diabetic activity seeds of Celocia argentea shows a weak inhibitory effect on polymeriza- An alcoholic extract of Celocia argentea seeds is used for the treatment of tion of tubulin (20% inhibition at 100 mM) as compared to that of moroidin 9, (IC 3.0 mM)[11,15, 52]. diabetes mellitus. The evaluation of anti-diabetic activity was verified by 50 blood glucose and body weight of alloxan-induced diabetic rats (27.8% at 3.7.Skin Depigmentation 250 mg kg-1 and 38.8% at 500 mg kg-1 body weight). Continual administra- The six compounds including Eugenyl O-b-D-glucopyranoside (citrusin tion of the seed extract significantly (p<0.01) reduced the blood glucose in C) were isolated from the leaves of Celocia argentea which shows 47.20 % alloxan-induced diabetic rats for two weeks with prevention of body weight [32,46] Tyrosinase inhibitory and 4.35 % superoxide scavenging activity. Citrusin lost . C showed strong tyrosinase inhibitory activity among other phenolic gly- cosides and hence used and skin depigmentation agent[18]. 3.3.Anti-hepatotoxic Activity The water extract of Celocia argentea was investigated for hepatoprotective 3.8.Wound Healing Activity effect in comparison of Cassia obtusifolia, Cucurbita moschata and Cur- Celocia argentea has been known as traditional medicine for sores, ulcers, cuma aeruginosa. In this study it was found that among the other species and skin eruptions. The alcoholic extract of Celocia argentea in an oint- the water extract of Celocia argentea is the most effective[47]. These experi- ment formulated studied for wound healing effectiveness using a rat burn ments were carried out on the CCl4 induced and D-galactosamine/li- wound model and postulated that this may be due to mitogenic and motogenic popolysaccharide, induced liver injury in mice. In same context Celosian promotion of dermal fibroblasts[53]. found in seed are also found to inhibit increase of serum enzymes (GPT, GOT, LTH) and bilirubin levels[47, 48]. The Celocian induced the tumor 4.TOXICITY necrosis factor-alpha (TNF-a) production in mice along with production of Pharmacological activity illustrates the beneficial or adverse effects of interleukin-1 ß (IL-1 ß) and nitric oxide (NO) in macrophage cell line J774.1 a drug on living organism. The main kind of biological activity is a in a concentration-dependent manner (1 to 1000 micrograms/ml)[49]. substance’s toxicity; the acute toxicity of Celocia argentea is reported[54]. Even at highest dose, 8gm.kg-1 body weights have found no toxicity effect Significant hepatoprotective effects was implicit due to the antioxidant of Celocia argentea leaves extract. capability of Celocia argentea and proved by CCl4 induced hepatotoxicity in mice, using celosin A 32 and celosin B 33 celosin C 34 and celosin D 35 5.CONCLUSION with oral doses 1.0, 2.0 and 4.0 mg kg-1[14]. Celocia argentea (Cockscomb) is an admired Asian, tropical, brilliant col- ors weed and documented for its diverse applications. This review has 3.4.Antiviral Activity focused for collection of recent phytochemical and ethnopharmacological Ethanolic extract of Celocia argentea leaves has been reported to have no information about the plant. This review is one of its kinds which describes anti-viral activity against measles virus (MV) on Hep-2 cells for pre-inocu- the food chemistry research of Celocia argentea. The review highlights lative and post-inoculative treatment. However, ethanolic extract of Hibis- novel and latest natural product isolated Celosin E, F and G and its in-vitro cus sabdariff leaves shows anti-viral activity against measles virus (MV) at anti-tumor and anti-inflammatory activity. Ethnopharmacological study 5, 10, 15 mg ml-1[50]. reveals that plant has been reported for its usefulness against gastrointesti- nal and gynecological disorder; however the present study shows that it has 3.5.Anti-inflammatory Activity been poorly explored. Celocia argentea has been studied for skin whitening In vitro anti-inflammatory activity of celosin E 36, celosin F 37, celosin G and yet to be explore for its application towards dermatological disorder. It 38 and cristatain 31 isolated from the seeds of Celocia argentea were tested is surprise to know that Celocia argentea has been reported traditionally for its against Indomethacin as a positive control and lipopolysaccharide for snakebite and as an abortifacient. Activities such as anti-oxidant, anti- (LPS) as a negative control. The celosin F 37 shows the comparable anti- inflammatory, anti-mitotic, anti-hepatotoxic, wound healing property have [7] inflammatory activity from its IC50 values . The seed extract of Celocia been studied in the great deal except anti-diabetic. Due to presence of argentea on intraperitoneal administration for 7 days before tumor inocula- phenols and phenolic acids Celocia argentea shows Tyrosinase inhibitory tion significantly inhibits liver metastatic caused by intraportal injection of and superoxide scavenging activity. Betalains, responsible for brilliant colour colon 26-L5 carcinoma cell, the same extract also shows immunomodulating of Celocia argentea have been characterized by spectroscopic method and properties[51]. found importance in food colouring as well as remedial medicine for oxida- tive stress. Celocia argentea seed in particular has been endearing with 3.6.Anti-miotic (Antitumor) Activity bicyclic peptides, Celogentin A-J and Moroidin, few of it are found to have The celosin E 36, celosin F 37, celosin G 38 and cristatain 31 isolated from inhibition activity such as tubulin polymerization. Celocia argentea has the seeds of Celocia argentea were tested for their in vitro antitumor activi- chemotypic similarity with the species Celocia cristata for few saponins ties toward five human cancer cell lines (SHG44, HCT116, CEM, MDA- like Celosin A-B and Cristatain. Celocia argentea also found as one of the MB-435 and HepG2) by the 3-(4,5- dimethylthiazol-2-yl)-2,5- promising vegetable for growing population of the globe. The newest num- diphenyltetrazolium bromide (MTT) assay. The cristatain 31 demonstrate ber of research articles explicates the budding interest in the Celocia argentea better cytotoxic activity among 36, 37, 38 and 31 against for its phytochemical constituents and the pharmacological activity. Hydroxydaunomycin hydrochloride (DOX) as a positive control[7]. The methanolic extract of Celocia argentea seeds found to contain 4-O-b-D- 6.ACKNOWLDEGEMENT apifuranosyl-(1 ® 2)2-b -D-glucopyranosyl-2-hydroxy-6- We thank to Deccan Education Society and Principal, Fergusson College for methoxyacetophenone 22 and 11 known compounds, among the isolated their continuous encouragement. We also thank to Board of Colleges and

Journal of Pharmacy Research Vol.5 Issue 2.February 2012 1076-1082 Shirish S. Pingale et al. / Journal of Pharmacy Research 2012,5(2),1076-1082 University Development (BCUD), Pune University, Pune, India and Uni- 26. Faboya OOP, The effect of pre-process handling conditions on the versity Grant Commission (UGC), New Delhi, India for their financial ascorbic acid content of green leafy vegetables, Food Chem., 38, 1990, support. 297-303. 27. Fafunso M, Bassir O, Effect of cooking on the vitamin C content of 7.REFERENCES fresh leaves and wilted leaves, J. Agri. Food Chem., 24, 1976, 354-355. 28. Fafunso M, Bassir O, Variations in the loss of vitamin C in leafy 1. Koh HL, Chua TK, Tan CH, A Guide to Medicinal Plant, an Illustrated, vegetables with various methods of food preparation, Food Chem., 2, Scientific and Medicinal Approach, World Scientific, Singapore, 2009, 1977, 51-55. 292. 29. Jain A, Katewa SS, Galav PK,Sharma P, Medicinal plant diversity of 2. Wee YC, A Guide to Medicinal Plants, Singapore Science Centre Publi- Sitamata wildlife sanctuary, Rajasthan, India, J. Ethnopharmacol., 102, cation, Singapore,1992. 2005, 143-157. 3. Feng N, Xue Q, Guo QH, Zhao R,Guo ML, Genetic Diversity and 30. Katewa SS, Chaudhary BL,Jain A, Folk herbal medicines from tribal Population Structure of Celosia argentea and Related Species Revealed area of Rajasthan, India, J. Ethnopharmacol., 92, 2004, 41-46. by SRAP, Biochem. Genet., 47, 2009, 521-532. 31. Gnanamani A, Shanmuga Priya K, Radhakrishnan N, Babu M, Antibac- 4. Uusiku NP, Oelofse A, Duodu KG, Bester MJ, Faber M, Nutritional terial activity of two plant extracts on eight burn pathogens, J. value of leafy vegetables of sub-Saharan Africa and their potential Ethnopharmacol., 86, 2003, 59. contribution to human health: A review, J. Food Compos. Anal., 23, 32. Vetrichelvan T, Jegadeesan M, Devi B, Anti-diabetic activity of alco- 2010, 499-509. holic extract of Celosia argentea LINN. seeds in rats, Biol. Pharm. 5. Wiart C, Medicinal plants of Southeast Asia, Pelanduk Publications, Bull., 25, 2002, 526-528. 2000. 33. Zheng XL, Xing FW, Ethnobotanical study on medicinal plants around 6. Jain SK, DeFilipps RA, Medicinal plants of India, 1-2, United State of Mt.Yinggeling, Hainan Island, China, J. Ethnopharmacol., 124, 2009, America Reference Publication Inc., US, 1991. 197-210. 7. Wu QB, Wang Y, Guo ML, Triterpenoid Saponins from the Seeds of 34. Kong YC, Jing-Xi X, But PPH, Fertility regulating agents from tradi- Celosia argentea and Their Anti-inflammatory and Antitumor Activi- tional Chinese medicines, J. Ethnopharmacol., 15, 1986, 1-44. ties, Chem. Pharm. Bull., 59, 2011, 666-671. 35. Li S, Long C, Liu F, Lee S, Guo Q, Li R,Liu Y, Herbs for medicinal baths 8. Schliemann W, Cai YZ, Degenkolb T, Schmidt J,Corke H, Betalains of among the traditional Yao communities of China, J. Ethnopharmacol., Celosia argentea, Phytochemistry, 58, 2001, 159-165. 108, 2006, 59-67. 9. Morita H, Suzuki H,Kobayashi Ji, Celogenamide A, a New Cyclic Pep- 36. Ticktin T, Dalle SP, Medicinal plant use in the practice of midwifery in tide from the Seeds of Celosia argentea, J. Nat. Prod., 67, 2004, 1628- rural Honduras, J. Ethnopharmacol., 96, 2005, 233-248. 1630. 37. Grosvenor PW, Supriono A, Gray DO, Medicinal plants from Riau 10. Suzuki H, Morita H, Iwasaki S, Kobayashi J, New antimitotic bicyclic Province, Sumatra, Indonesia. Part 2: antibacterial and antifungal ac- peptides, celogentins D, H, and J, from the seeds of Celosia argentea, tivity, J. Ethnopharmacol., 45, 1995, 97-111. Tetrahedron, 59, 2003, 5307-5315. 38. Dung N, Loi DT, Selection of traditional medicines for study, J. 11. Suzuki H, Morita H, Shiro M,Kobayashi Ji, Celogentin K, a New Cyclic Ethnopharmacol., 32, 1991, 57-70. Peptide from the Seeds of Celosia argentea and X-Ray Structure of 39. Chen CP, Lin CC, Tsuneo N, Screening of Taiwanese crude drugs for Moroidin., Tertrahedron, 60, 2004, 2489-95. antibacterial activity against Streptococcus mutans, J. Ethnopharmacol., 12. Morita H, Shimbo K, Shigemori H, Kobayashi J, Antimitotic activity 27, 1989, 285-295. of moroidin, a bicyclic peptide from the seeds of Celosia argentea, 40. Houghton PJ, Osibogun IM, Flowering plants used against snakebite, J. Bioorg. Med. Chem. Lett., 10, 2000, 469-471. Ethnopharmacol., 39, 1993, 1-29. 13. Mundhe KS, Bhave AA, Torane RC, Deshpande NR, Kashalkar RV, 41. Akindahunsi A, Salawu S, Antioxidant indices of some green leafy Removal of cationic dye from aqueous solution using raw agro wastes as vegetables, Trop. Sci., 45, 2005, 33-35. non-conventional low- cost adsorbent., Orient. J. Chem., 25, 2009, 42. Salawu SO, Akindahunsi AA, Comuzzo P, Chemical Composition and 953-959. in vitro Antioxidant Activities of Some Nigerian Vegetables, J. Pharm. 14. Xue QA, Sun ZL, Guo ML, Wang Y, Zhang G,Wang XK, Two new Toxic., 1, 2006, 429-437. compounds from Semen celosiae and their protective effects against 43. Malomo SO, Ore A, Yakubu MT, In vitro and in vivo antioxidant CCl -induced hepatotoxicity, Natural Product Research, 25, 2011, 772- 4 activities of the aqueous extract of Celosia argentea leaves, Indian J 780. Pharmacol., 43, 2011, 278-285. 15. Kobayashi J, Suzuki H, Shimbo K, Takeya K,Morita H, Celogentins A- 44. Cai Y, Sun M,Corke H, Antioxidant Activity of Betalains from Plants C, new antimitotic bicyclic peptides from the seeds of Celosia argentea, of the Amaranthaceae, J. Agri. Food Chem., 51, 2003, 2288-2294. J. Org. Chem., 66, 2001, 6626-6633. 45. Cai YZ, Sun M, Corke H, Characterization and application of betalain 16. Feng Y,Chen G, Total Synthesis of Celogentin C by Stereoselective C- pigments from plants of the Amaranthaceae, Trends Food Sci. Tech., H Activation, Angewandte Chemie, 49, 2010, 958-961. 2005, 370. 17. Strack D, Vogt T,Schliemann W, Recent advances in betalain research, 46. Barlocco D, Perez MJP, Monitor: molecules and profiles, Drug Discov. Phytochemistry, 2003, 247. Today, 7, 2002, 1064-1065. 18. Sawabe A, Nomura M, Fujiharay Y, Tada T, Hattori F, Shiohara S, 47. Hase K, Kadota S, Basnet P, Namba T,Takahashi T, Hepatoprotective Shimomura K, Matsubara Y, Komemushi S, Okamoto T, Saburou K, Effects of Traditional Medicines. Isolation of the Active Constituent Isolation and Synthesis of Cosmetic Substances from African Dietary from Seeds of Celosia argentea, Phytother. Res., 10, 1996, 387-392. Leaves, Celosia argentea L. for Skin Depigmentation, J. Oleo. Sci., 51, 48. Hase K, Xiong Q, Kadota S, Bioactive Natural Products (Part F), Atta- 2002, 203-206. ur-Rahman, Volume 25, Part 6, Elsevier, 2001, 459-482. 19. Shuo S, Xiao D, Ming-An O, Zu-Jian W,Lian-Hui X, A new phenolic 49. Hase K, Basnet P, Kadota S, Namba T, Immunostimulating activity of glycoside and cytotoxic constituents from Celosia argentea., J. Asian Celosian, an antihepatotoxic polysaccharide isolated from Celosia Nat. Product. Res., 12, 2010, 821-827. argentea., Plant Med., 63, 1997, 216-129. 20. Jong TT, Hwang CC, Two Rare Isoflavones from Celosis argentia, 50. Sunday OA, Munir AB, Akeeb OO, Bolanle AA, Badaru SO, Antiviral Planta Med., 61, 1995, 584-585. effect of Hibiscus sabdariffa and Celosia argentea on measles virus, 21. Suzuki T, Tomita-Yokotani K, Yoshida S, Takase Y, Kusakabe I, Afr. J. Microbiol. Res., 4, 2010, 293-296. Hasegawa K, Preparation and isolation of oligogalacturonic acids and 51. Hayakawa Y, Fujii H, Hase K, Ohnishi Y, Sakukawa R, Kadota S, Namba their biological effects in Cockscomb (Celosia argentea L.) seedlings, T, Saiki I, Anti-metastatic and immunomodulating properties of the J. Plant Growth Regul., 21, 2002, 209-215. water extract from Celosia argentea seeds., Biol. Pharm. Bull., 21, 22. Wang Y, Lou Z, Wu QB,Guo ML, A novel hepatoprotective saponin 1998, 1154-1159. from Celosia cristata L., Fitoterapia, 81, 2010, 1246-1252. 52. Ma B, Banerjee B, Litvinov DN, He L,Castle SL, Total Synthesis of the 23. Sun ZL, Wang Y, Guo ML, Li YX, Two new hepatoprotective saponins Antimitotic Bicyclic Peptide Celogentin C, J. Am. Chem. Soc., 132, from Semen celosiae, Fitoterapia, 81, 2010, 375-380. 2008, 1159-1171. 24. Wu QB, Wang Y, Guo ML, Triterpenoid Saponins from the Seeds of 53. Priya KS, Arumugam G, Rathinam B, Wells A,Babu M, Celosia argentea Celosia argentea and Their Anti-inflammatory and Antitumor Activi- Linn. leaf extract improves wound healing in a rat burn wound model, ties, Chem. Pharm. Bull., 59, 2011, 666-671. Wound Repair Regen., 12, 2004, 618-625. 25. Badifu GIO, Effect of long-term storage of processed Nigeria-grown 54. Pingale SS, Markadeya AG and Gawali SA, Toxicity Study of Celocia edible leafy green vegetables on vitamin C content, J. Agri. Food Chem., argentea, Int. Res. J. Pharm, 2(1), 2011, 263-266. 39, 1991, 538-541. Source of support: Nil, Conflict of interest: None Declared Journal of Pharmacy Research Vol.5 Issue 2.February 2012 1076-1082