Isolation, spectroscopic characterization and molecular modeling studies of mixture of curcuma longa, ginger and seeds of fenugreek

Members of the Zingiberaceae such as turmeric (Curcuma longa L.) and ginger (Zingiber officinale Rosc.) and fenugreek accumulate at high levels in their rhizomes important pharmacologically active metabolites that appear to be derived from the phenylpropanoid pathway. The major constituens of these spices are in ginger, the gingerols, in turmeric these are the curcuminoids and in fenugreek 5, 7-dihydroxy-2-(4-hydroxyphenyl)-6(3,4,5-trihydroxy-6(hydroxymethyl)tetrahydro-2H-pyran-2-yl)chroman-4one,diosgenin.The compound has been synthesized from the mixture of curcuma longa rhizome, ginger and seeds of fenugreek. The novel compound having chemical name is 2-(5-(3,5-dihydroxy-6-(4-hydroxy-2-(methylperoxyamino)tetrahydro-2H-pyran-3-yloxy)4-phenyltetrahydro-2H-pyran-2-yloxy)-2-(methylperoxyamino)-6-(2,4,5-trihydroxy-6(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)tetrahydro-2H-pyran-3-yloxy)-5-hydroxy6-methyl-4-(methylperoxyamino)dihydro-2H-pyran-3(4H)-one. The compound is characterized by various spectroscopic techniques. The compound has triclinic crystal system and the molecular structure has been optimized by MM2 calculation. Key–words :Curcuma, Rhizome, Ginger, Shoagol, Fenugreek, Spectroscopy, Molecular Modeling Introduction Turmeric, ginger and fenugreek are very important spices for cooking vegetarian as well as non-vegetarian foods in Indian subcontinent. These spices are common food adjuncts that impart color, flavor and aroma. Curcuma longa, commonly known as turmeric is also widely used as colorings agent and known for its medicinal properties . Many research studies have been conducted on Curcumalonga L. (turmeric), in particular with regard to Parashuram Mishra et al./Int.J. PharmTech Res.2009,1(1) 80 its secondary metabolites as sources of antioxidants .However, there is no recorded data pertaining to the abundance and quality of curcuminoids from the turmeric grown in Indian subcontinent .On the basis of emerging scientific data on turmeric from various parts of the Indian subcontinent with regard to its therapeutic values , we have decided to establish oleoresin yields and the chemical fingerprints for the turmeric grown in Indian subcontinent. The aforementioned paucity in the literature is resolved as a result of the data generated from is research work performed on the turmeric grown in India. Curcumalonga L. is a perennial rhizomatous erect herb from the Zingiberaceae family that belongs to the class Monocotyledons . Some of the therapeutically active compounds in the oleoresin extracted from the rhizomes of C.longa are called curcuminoids. Curcuminoids are inherent compounds of the species C. longa and are responsible for the antioxidant activity of the oleoresin . There are three main compounds of this pigmented curcuminoid complex, namely, curcumin chemically name is[(E,E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5dione],demethoxycurcumin[feruloyl(4-hydroxycinnamoyul)methane],and bisdemethoxycurcumin or bis(4-hydroxylcinnamoyl)methane (Figure 1).Curcumin (C21H20O6) constitutes 50–60% of the curcuminoids found in C. longa. In addition to the curcuminoids, there are essential oils containing monocyclic monoterpenes, sesquiterpene (bisabolanes and germacranes), arabinogalactans and ar-turmerone . The confluence of healthy living and eating has been the impetus for the scientific disciplines of functional foods and nutraceuticals . Although there have been many characterization studies of the turmeric rhizome , there is still uncertainty with regard to the effects of extracting freshly processed rhizomes versus dried milled rhizomes on the quantity and quality of their oleoresins. The phenolic secondary metabolites, curcumi-noids, play an important role in the quality of turmeric-containing foods because they affect the organoleptic traits of the foods in terms of aroma, flavor, and taste. The stability of curcuminoids, their biosynthesis, and degradation are influential to food quality. In terms of biosynthesis, one of the key enzymes, phenylalanine ammonia-lyase, can be induced by different environmental stress conditions . Appropriate post harvesting processing of the rhizome can sustain phenolic quality of plant material . These novel scientific findings will no doubt build leverage for the turmeric grown in Indian subcontinent in the marketplace, benefiting the various Indian spice houses and commercial exporters of the spice. Ginger (Zingier officinale Roscoe; family Zingiberaceae) is a monocotyledonous, sterile cultigens thought to have originated in India or Southeast Asia, from where it was introduced to other parts of the world . Both fresh and dried ginger rhizomes are used Parashuram Mishra et al./Int.J. PharmTech Res.2009,1(1) 81 worldwide as a spice, and ginger and ginger extracts are used extensively in the food, beverage, and confectionary industries in the production of products such as marmalade, pickles, chutney, ginger beer, ginger wine, liquors, biscuits, and other bakery products. The unique flavor properties of ginger arise from the combination of pungency and aromatic essential oil. Ginger is also widely used in both traditional and contemporary natural medicine. It has been used medicinally in India since ancient times and is mentioned in Vedic texts dating back to around 4000 BCE 28 .Ginger is included in the British, European, Chinese, and Japanese pharmacopoeias, as well as in many other national pharmacopoeias, and the World Health Organization has published a monograph for Rhizoma Zingiberis. The medicinal uses of ginger are diverse and include the treatment of dyspepsia, colic, diarrhea, colds and flu, and poor appetite. It is also recommended as an anti-inflammatory agent in rheumatic and muscular disorders and to increase longevity . Clinical trials support the use of ginger preparations in the prevention of motion sickness . and vomiting in pregnancy ,while the evidence is more ambiguous in the case of musculoskeletal disorders. The main pungent compounds in fresh ginger are a series of homologous phenolic ketones known as gingerols (Figure 3). The gingerols are thermally unstable and are converted under high temperature to shogaol (after shoga, the Japanese word for ginger;) . Shogaols, which are more pungent than gingerols, are the major pungent compounds in dried ginger .The active ingredient in turmeric is curcumin and that in ginger are gingrol and hexahydrocurcumin Both these compounds prevent oxidation of oils and fats. Trigonella foenum graecum Linn belongs to the family Leguminosae and it is popularly known as Fenugreek . Trigonella foenum graecum Linn is native to the area from Indian subcontinent and also much cultivated in India and China. Fenugreek is one such plant whose seeds and leaves are used not only as food but also as an ingredient in traditional medicines . In India, the seeds of fenugreek were used in Ayurveda and Siddha to treat fever, dysentery heart diseases and diabetic while in Unani system, this plant issued as a resolvent, aphrodisiac, diuretic, emmenagogue and tonic. In China, fenugreek seed swear used as a galactogogue to encourage lactation .The past phytochemical investigations on the seeds reveals the presence of Diosgenin, Trigonelline, Gitogenin, Vicenins 1 and 2, Vitexin, Quercetin, Luteolin, Kaempferol, Sitosterol etc., moreover the endosperm of the seeds is rich in galactomannan..The major constituents of fenugreek are given in figure. Several synthetic spasmogens and spasmolytics have been used in the field of medicine [, in spite of their side effects and minimum therapeutic index. Even though many drugs are available with spasmogenic and spasmolytic properties, search for a drug of plan origin Parashuram Mishra et al./Int.J. PharmTech Res.2009,1(1) 82 with maximum potency and minimum side effects continues. Since no scientific report of the previous investigations detail are available on the effect of fenugreek on the isolated smooth muscles, the present study was undertaken to screen the isolatation mixture of curcuma rhizome, ginger and seeds of fenugreek and characterized by physical techniques. Figure1 Three curcuminoid structure Parashuram Mishra et al./Int.J. PharmTech Res.2009,1(1) 83 Figure 2: Structures of the major pungent compounds in ginger, gingerol and shogaols. Figure 3. Structure of diosgenin. Parashuram Mishra et al./Int.J. PharmTech Res.2009,1(1) 84 Figure4..5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3,4,5-trihydroxy-6(hydroxymethyl) tetrahydro-2H-pyran-2-yl)chroman-4-one The mixture of tumeric, ginger and seeds of fenu greek generally used in joint pain relief in rural area of subcontinent as well as heart desease.The aim of this paper is to isolate a mixture of the spices and spectroscopy studies of isolated compound. On the basis of experimental observation the structure of the proposed compound can be established.