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Identification of Phenolic Antioxidants in Ipomoea Mauritiana Jacq. Using Spectrophotometric and Mass Spectroscopic Studies

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Identification of Phenolic Antioxidants in Ipomoea Mauritiana Jacq. Using Spectrophotometric and Mass Spectroscopic Studies Short communication Identification of phenolic antioxidants in Ipomoea mauritiana jacq. using spectrophotometric and mass spectroscopic studies Cheruthazhakkat Sulaiman 1*, Sivadasan Pillai Geetha, Balachandran Indira 1Centre for Medicinal Plants Research, Arya Vaidya Sala Kottakkal-676503, Kerala, India Article history: Abstract Received: Feb 16, 2013 Objective: Ipomoea mauritiana is used in both Ayurveda and folk Received in revised form: Jul 17, 2013 medicine systems. The tuberous roots are known to be diuretic, Accepted: Jul 21, 2013 depurative, carminative, and anthelmintic. The objective of the current Vol. 4, No. 2, Mar-Apr 2014, study was to identify phenolic antioxidants from I. mauritiana using 89-96 spectrophotometric and LC-MS analysis. Materials and Methods : An activity-guided fractionation and * Corresponding Author: purification process was used to identify the antioxidative components Tel: +914832806210 from I. mauritiana tuber. Dried mature tubers of I. mauritiana were Fax: +914832746080 extracted with 80% methanol and then partitioned by chloroform, [email protected] ethyl acetate, acetone, and methanol. The acetone fraction showed the strongest 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging Keywords: activity among four fractions and was subjected to separation and Ipomoea mauritiana purification using preparative reverse-phase high-performance liquid Phenolics DPPH chromatography (HPLC). LC-ESI-MS Results : Two compounds were separated from the acetone fraction using preparative LC fraction collector. The purified compounds were screened for their antioxidative potential using DPPH assay. The compounds were subjected to LC-MS analysis in ESI negative mode. One of the compounds was identified as Caffeoyl glucose based on the mass fragmentation. Conclusion: The acetone fraction showed highest radical scavenging activity and the phytoconstituents of the same were identified by LC- MS/MS analysis. Please cite this paper as: Sulaiman C, Sivadasan PG, Balachandran I. Identification of phenolic antioxidants in Ipomoea mauritiana jacq. using spectrophotometric and mass spectroscopic studies. Avicenna J Phytomed, 2014; 4 (2): 89-96. Introduction source plants of ‘ Vidari ’, an Ayurvedic drug. Ipomoea mauritiana Jacq. (Syn. I. ‘Vidari ’ is a component of about 50 paniculata (L.) R. Br.; I. digitata Baker & Ayurvedic formulations including Rendle) is a medicinal plant belonging to the Chyavanaprash. The annual industrial family Convolvulaceae and is one of the requirement of ‘Vidari’ is about 500–1000 AJP, Vol. 4, No. 2, Mar-Apr 2014 89 Sulaiman et al. Metric Tonnes (Ved and Goraya, 2008). The powder is reported to be of beneficial use to Ayurvedic Pharmacopoeia of India correlates persons suffering from or prone to coronary ‘Vidari’ to tubers of Pueraria tuberosa disease problems and diabetes (Moushumi et (Roxb. ex Willd.) DC (Fabaceae) and al., 2010). Kshiravidari to I. mauritiana Jacq. and Phenolic compounds are considered to be specify macro–microscopic characterization secondary metabolites and are derived from and chemical profiling of the raw materials phenylalanine. Phenolics can be defined as for quality standardization (API, 2006). substances which possess an aromatic ring However, as per Ayurvedic descriptions both and have one or more hydroxyl groups. these species are attributed similar properties Plants contain a large variety of phenolic and are substituted by each other derivatives, including benzoic acids, (Venkatasubramanian et al., 2009). Apart cinnamic acid derivatives, flavonoids, from tubers of P. tuberosa and I. mauritiana , isoflavonoids, lignans, and tannins (Shahidi, tubers of Adenia hondala (Gaertn.) de Wilde 2000).There are about 8000 naturally (Passifloraceae) and the pith of Cycas occurring plant phenolics and about half of circinalis L. (Cycadaceae) are also traded as them are flavonoids. These flavonoids are ‘Vidari ’ (Ved and Goraya, 2008). closely related structures, based on the C 15 ‘Vidari ’ is used as aphrodisiac, heterocyclic nucleus of flavones and varying cardiotonic, demulcent, diuretic, refrigerant, chiefly in the number of phenols, such as and galactogogue (Chopra et al., 1992). The phenolics acid, phenyl propanoids, and roots are sweet, cooling in action, appetizer, phenolics quinones (Harborne and Boxter, galactagogue, rejuvenating, stimulant, 1995). It is a most widely distributed natural carminative, and tonic (Sivarajan and product in plants and over 2000 different Balachandran, 1994). It is also used in compounds are reported occurring both in the emaciation, enteric fever, and spermatorrhea free state and as glycosides. The major (Pandey, 2004). general categories are flavones, flavanones, I. mauritiana is a much branched flavanols, anthocyanidins, and isoflavones glabrous twining perennial shrub with large (Mukerjee, 2002). tuberous roots. The species is distributed Mass spectrometry is one of the most throughout India in deciduous and evergreen sensitive methods of molecular analysis and forests and coastal tracts and widely yields information on the molecular weight naturalized in tropical parts of the world. as well as on the structure of the analytes. Leaves simple, alternate, long-petioled, Liquid chromatography-electrospray palmately 5–7 lobed, flowers bisexual, purple ionization mass spectrometry (LC-ESI-MS) in long peduculate axillary cymes, capsule has been recognized as a powerful analytical ovoid, four-celled, four-seeded with wooly tool with its high sensitivity, short run time, seeds (Sivarajan and Balachandran, 1994; and less use of toxic organic solvents (mobile Warrier et al., 1995). It contains phase) as compared with reversed phase phytoconstituents such as taraxerol, taraxerol stand-alone HPLC coupled with diode-array acetate, β-sitosterol, scopoletin, and 7-O-β- detector (Liu et al., 2005). LC coupled with Dglycopyranosyl scopoletin (Khan et al., mass spectrometry (LC-MS) is better suited 2009). Distinct microscopic as well as for the analysis of non-volatile polar phytochemical characters of tubers of I. compounds in their natural form. Generation mauritiana have been developed for quality of free radicals or reactive oxygen species control of crude drugs (Karthik et al., 2009). (ROS) during metabolism and other activities Regular intake of I. mauritiana tuber root beyond the antioxidant capacity of a AJP, Vol. 4, No. 2, Mar-Apr 2014 90 Identification of phenolic antioxidants in Ipomoea mauritiana biological system gives rise to oxidative apparatus. After filtration, the filtrate was stress (Zheng and Wang, 2001), which plays concentrated to dryness by rotary evaporator a role in heart diseases, neuro-degenerative at 48 °C, then weighed and diluted to 200 ml diseases, cancer, and ageing process (Astley, with 80% methanol. The solution was 2003). washed with 30 ml petroleum ether (2×15 This concept is supported by increasing ml) to remove lipids. Twenty ml of absolute evidence indicating that oxidative damage ethanol (2×10 ml) was used to precipitate plays a role in the development of chronic, protein from the solution. After age-related degenerative diseases, and that centrifugation at 10000 rpm for 20 min, the dietary antioxidants can oppose this, thus supernatant was concentrated by rotary lower the risk of those diseases (Atoui et al., evaporator at 48 °C. It was then fractionated 2005). Antioxidants are substances that when into 50 ml each of chloroform, ethyl acetate, present in low concentrations, compared with acetone, and methanol using liquid-liquid those of an oxidisable substrate significantly solvent extraction techniques. delay or prevent oxidation of that substance (Halliwell and Gutteridge, 1989). Estimation of total phenolic content (TPC) In the present study, different fractions of Total phenolic content was determined in I. mauritiana were screened for their all of the fractions. The assay was based on antioxidant activity and mass spectral studies the reduction of phosphomolybdate ion of were carried out for the identification of Folin-Ciocalteu reagent by the phenolate ion major constituents in active fraction. of the samples (Singleton et al., 1965). A desired amount of plant extract, distilled water, and 1 N Folin-Ciocalteu reagent was taken into a tube and mixed Materials and Methods thoroughly. After an interval of 3 min, 2 ml Plant material of 2% sodium carbonate solution was added Mature tubers of I. mauritiana were and the mixture was allowed to stand for 30 collected from the germplasm maintained at min with intermittent shaking. The Centre for Medicinal Plants Research absorbance of the mixture was measured at (CMPR), Arya Vaidya Sala (AVS), 750 nm using spectrophotometer. Different Kottakkal, Kerala, India and authenticated by gallic acid standards were used for obtaining the Plants Systematics Division of the centre. a standard curve. The total phenolic content The collected plant material was then shade was expressed as gallic acid equivalents dried and powdered. (GAE) in mg/g of sample. Chemicals DPPH radical scavenging activity DPPH was purchased from Sigma The method described by Tepe et al. Chemicals (Bangalore, India), while formic (2005) was used with minor modifications. acid and acetonitrile (LC-MS grade) were One ml of 500 µM DPPH in methanol was obtained from Burdick & Jackson, USA. All mixed with equal volume of the extract other reagents used were of analytical grade solution in phosphate buffer (pH 7.4). The (E Merck, India). mixture was slightly shaken and kept in dark for 20 min. The
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