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Isolation and Identification of Phenolic Compounds from Boswellia Ovalifoliolata Bal

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Isolation and Identification of Phenolic Compounds from Boswellia Ovalifoliolata Bal Available online on www.ijddt.com International Journal of Drug Delivery Technology 2014; 4(1); 14-21 ISSN: 0975 4415 Research Article Isolation and Identification of Phenolic Compounds from Boswellia ovalifoliolata Bal. & Henry and Their Free Radical Scavenger Activity Savithramma N, *Linga Rao M, Venkateswarlu P Department of Botany, S.V. University, Tirupati-517502, A.P, India Available online: 1st January 2014 ABSTRACT Boswellia ovalifoliolata Bal. and Henry (Burseraceae) is a potential medicinal tree used traditionally in the treatment of ulcers, inflammation, arthritis, obesity and diabetes. The present study aimed to isolate phenolic compounds from stem bark and gum and test for the ability of the extracted phenols of Boswellia ovalifoliolata. Total 78 phenolic compounds were obtained when the plant materials were processed through 70% acetone and poly vinyl poly pyrrolidone; and characterized by U.V. Visible spectrometry, High performance liquid chromatography/ electrospray ionization mass spectrometry. Among the isolated phenols, 28 phenolic compounds have been identified based on their retention time and m/z values. These phenols have showed good antioxidant activity the highest hydrogen peroxide (H2O2) radical scavenging effect of the isolated phenolic compounds has been recorded at 81.8% when compared to the DPPH; and superoxide ion activities with reference to ascorbic acid. This study illustrate the rich array of phenolic compounds and their free radical scavenging activity of stem bark and gum of Boswellia ovalifoliolata could be utility as health beneficial bioactive compounds. Key words: Boswellia ovalifoliolata, stembark, gum, phenolic compounds, Electro Spray Ionization mass spectrometry, hydrozen peroxide INTRODUCTION orally in small quantities (10 ml) two times a day to cure Boswellia ovalifoliolata Bal. and Henry is an endemic, hydrocoel (Vedavathy et al., 1995). Equal mixture of gum endangered, globally threatened medicinal taxon belongs and stem bark in one tea spoonful given daily with sour to the family Burseraceae (Savithramma, 2006). This milk on empty stomach for a month to cure stomach ulcers deciduous medium sized tree occurs at an altitudinal range (Nagaraju and Rao, 1990). Tribals (Nakkala, Sugali and of 250-600 m on Seshachalam hill range of Eastern Ghats Chenchu) and local healers of surrounding villages making of India. Seshachalam hills are habours large number of deep incisions on the main trunk to extract the gum but endemic, endangered, rare, threatened and key stone unknowingly causes damage to immature plants leading to species due to its vivid geographical conditions and depletion of this species in its natural habitat. Herbal climatic factors which are favourable for the distribution medicines are crude plant drugs used by tribals and rural of unique endemic plant wealth (Savithramma et al., folk and has also been studied for biological synthesis of 2010). The fresh leaf juice used to prevent throat ulcers silver nanoparticles and antimicrobial activity (Savithramma and Sulochana, 1998). Decoction of the (Savithramma et al., 2011; Savithramma et al., 2011; stem bark 10 – 25 ml per day reduces rheumatic pains Savithramma et al., 2011), phytochemical screening (Nagaraju and Rao, 1990). The gum obtained from the (Savithramma et al., 2010), quantification of trunk which is highly medicated, this gum is sold in the phytochemicals (Savithramma and Bhumi, 2011), local market by the native tribals as Konda sambrani in antiulcer activity (Venkateswarlu et al., 2012) and Telugu language. Small lumps of fresh light yellow antihyperlipidermic activity (Geetha and Ganapathy, coloured liquid oozes out from the stem and hardens on 2013). exposure. Amyrins are the chief constituents of the gum Phenolic compounds are one of the most diverse groups of together with resin acids and volatile acids. Shade dried phytochemicals that are universally distributed in fruits, gum is powdered dissolved in water and mixed with curd vegetable and herbs. Approximately 8000 phenolic and given orally to cure amoebic dysentery (Sudhakar, compounds have been isolated from natural resources. 1998). Gum powder of Boswellia ovalifoliolata and Polyphenols in nature generally occur as conjugates of Boswellia serrata and fruit powder of Pedalium murex sugar, usually o-glycosides, phenolic acids contain two mixed in equal parts and made into paste and apply distinctive carbon frame works, the hydroxyl cinnamic and externally on the affected part of the testicle to cure hydroxyl benzoic structures (Santos et al., 2003). hydrocoel. Gum powder mixed with white precipitate of Although the basic skeleton remains the same, the numbers pounded stem of Tinospora cardifolia and honey given and positions of the hydroxyl groups on the aromatic ring *Author for correspondence: E-mail: [email protected] Savithramma N et al. / Isolation and Identification… Table 1: Identified phenolic compounds in stembark and gum of B. ovalifoliolata S. Pseudo molecular Stem Molecular formula Compound Gum No. ion m/z values Bark 1. 125 Guaiacol G + - C H O + + 2. 169 7 6 5 Gallic acid C H O + - 3. 175 6 5 6 Ascorbic acid C H O + - 4. 301 15 5 7 Quercetin C H O + - 5. 315 16 11 7 Isorhamnetin C H O + - 6. 329 20 25 4 Carnosol C H O + - 7. 331 20 27 4 Carnosic acid C H O + + 8. 377 25 32 13 Oleuropein C H O + - 9. 388 21 23 7 Medioresinol C H O + - 10. 435 21 23 10 Phloridzin 11. 488 Coumaroyl hexose + - 12. 489 Kuempferol acetylhexoside + - C H O + - 13. 533 9 8 4 Caffeic acid hexoside 14. 595 Quercetin-3 pentosylhexoside + + 15. 121 C7H6O2 Benzoic acid - + C H O - + 16. 152 8 10 3 Hydroxytyrosol C H O - + 17. 153 7 5 4 Protocatechuic acid C H O - + 18. 165 9 10 3 Phloretic acid C H O - + 19. 191 16 18 9 Chlorogenic acid C H O - + 20. 353 16 17 9 Chlorogenisic acid 21. 377 5-coumaroylquinic acid - + 22. 409 Coumaric acid - + C H O - + 23. 447 21 19 11 Luteolin-7- glucoside 24. 449 Cyanidin-3-glucoside - + 25. 483 1,5-di coumaroylquinic acid - + C H O - + 26. 515 25 23 12 Dicaffeoylquinic acid 27. 711 Quercetin-7-hexoside-3-hexoside - + 28. 1008 Heptamericprocyanidin - + Table 2: Free radical scavenging activity of stembark and gum of B. ovalifoliolata Sample 8 µl 15 µl 30 µl SB 46.34% 58.66% 81.8% Hydrogen Peroxide G 18.75 % 27.75 % 71.7% SB 19.22% 19.22% 58.81 % DPPH G 12.54% 23.12 % 31.13 % SB 14.52% 35.22% 56.2 % Superoxide G 6.15% 8.25 % 11.15 % make the difference and establish the variety. Many ageing and inflammatory activity (Braca et al., 2002). activities have been reported for most of the phenolic Recently there has been an upsurge of interest in the compounds from plants they act as anti-oxidant, anti- therapeutic potentials of medicinal plants as antioxidants inflammatory, anti-viral and anti carcinogenic agents in reducing free radical induced tissue injury (Pourmorad (Visioli et al., 2002). et al., 2006). Besides well known and traditionally used Natural antioxidants such as phenols, flavonoids and natural antioxidants from tea, wine, fruits, vegetables and tannins are increasingly attracting attention because they spices are already exploited commercially either as are natural disease preventing, health promoting and anti- antioxidant additives or a nutritional supplements. ageing substances (Ozyurt et al., 2004). Antioxidants may Number of plant species have been investigated in the serve the task of reducing oxidative damage in humans search for novel antioxidants (Koleva et al., 2002). Still induced by free radicals and reactive oxygen species under there is a demand to find more information concerning the oxidative stress conditions. These conditions can cause antioxidant potential of plant species. Hence the present 15 DNA and protein damage, lipid peroxidation, cancer, Page IJDDT, January-March 2014, 4(1), 14-21 Savithramma N et al. / Isolation and Identification… Fig 1: Mass spectra of phenolic extract of stembark of B. ovalifoliolata spectra obtained in + Ve ion mode fragmentation Fig 2: Mass spectra of phenolic extract of stembark of B. ovalifoliolata spectra obtained in the – Ve ion mode fragmentation study to isolate the polyphenols compound and tested the PVPP. The remaining PVPP was re-extracted twice again antioxidant activity of Boswellia ovalifoliolata. with 200 mL of fresh extraction solvent for the same period time that was used before. The combined extracts were MATERIAL AND METHODS evaporated at room temperature by rotary evaporation to Extraction of polyphenols from stembark and gum: remove the organic solvent (acetone). Stembark and gum of Boswellia ovalifoliolata were HPLC-ESI-MS/MS analysis: The qualitative study of the collected from Tirumala hills, Chittoor District of Andhra phenolic compounds in all samples was performed by Pradesh, India during July, 2012. The materials were HPLC coupled on-line with electrospray ionization (ESI) washed thoroughly and shade dried. mass spectrometry. The HPLC system (Agilent 1100 30 g of stem bark and gum powders reduced in a mortar series) consisted of a low-pressure quaternary pump and consequently extracted with 500 mL of (Agilent 1100 series) and an auto-sampler. A quadropole dichloromethane by ultra-sonication for about 30 min and ion trap mass spectrometer (Agilent 1100) equipped with shaken by vortex for 30 min to remove hydrophilic an ESI source in the positive and negative ion mode and compounds. Dilapidated powder were extracted with 500 Xcalibur software Version 1.4 (Finningan) were used for mL of acetone/water (70:30, v/v) by sonication for 15 min data acquision and processing. and shaking for more 15 min to extract polyphenols. 150 Free Radical Scavenging Activity: Hydrogen Peroxide mL of each stembark and gum water extract (pH adjusted scavenging activity of Boswellia ovalifoliolata stembark to 4.0) was mixed with 5 g of PVPP (30 mg/mL) for 15 extract and gum were determined using a modification of 16 min of shaking for adsorption of phenolic compounds to the method of Ruch et al (1989).
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