Recent Developments in Research of Celocia Argentea: a Review
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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 Amaranthaceae and commonly known as Cockscomb. This weed spread in all the continents with major as Asia and Africa. The plant 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: Celosia 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 Plants 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.