Isolation and Identification of Phenolic Compounds by HPLC and Electrospray Ionization Mass Spectrometry and their Free Radical Scavenging Activity of Shorea tumbuggaia Roxb.
Keywords:
Shorea tumbuggia, stembark, phenolic compounds, liquid chromatography, Electro Spray Ionization mass spectrometry, hydrozen peroxideAbstract
The impetus for developing analytical methods for phenolic compounds in natural products has proved to be multifaceted. The traditional usage of Shorea tumbuggaia as a folklore medicine, the plant parts are administered to counteract different ailments. Hence the present study intended to isolate phenolic compounds from stem bark of Shorea tumbuggaia by using 70% acetone and poly vinyl poly pyrrolidone; and characterized by U.V. Visible spectrometry, High performance liquid chromatography/ electrospray ionization mass spectrometry. And an assessment of the ability of the extracted phenols to scavenge the hydrozen perioxide; sueproxide, DPPH was determined with reference to ascorbic acid by spectrophotometric methods. Total 90 phenolic compounds were obtained at both positive and negative ion modes of LCMS. Among the isolated phenols, 20 phenolic compounds have been identified based on their retention time and m/z values. Namely, Benzoic acid, caffeoyl-5-ferryol quinic acid, thymol, homovanillic acid, eudesmic acid, caffeic acid, 9 CoA, chrysin, pinocembrin, luteolin, quercetin-3-rutinoside, ellagic acid, cohumulone, caffeic acid hexoside, lupulone, deoxy hexoside of ellagic acid, 3’-4-Di hydroxyl 5-6 dimethoxy 7-0-glucoside flavones, oleuropein, pelargonidin-3-rutinoside and heptameric procyanidin. These phenols has 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 of Shorea tumbuggaia could be utility as health beneficial bioactive compounds.
References
. Passardi F, Cosio C, Penel C, Dunand
C. Peroxidases have more functions
than a swiss army knife plant cell
reports 2005 ; 24: 255-265.
. Manach C, Scalbert A, Morand C,
Remesy C, Jimenez L. Polyphenols:
Food sources and bio availability.
Amer J Clin Nutri 2004;79 (5): 727-
. Visioli F, Poli A, Galli C. Antioxidant
and other biological activities of
phenols from Olives and olive oil.
Medicinal Research Review 2002; 22
(1): 65-75.
. Robbins RJ. Phenolic acids in foods;
an overview of analytical
methodology. J Agric Food Chem
;51:2866-2887.
. Santos BC, Garcia VC, Tomas BF
Online identification of flavonoids by
HPLC coupled to diode array
detection. In methods in polyphenol
Analysis. U.K. 2003; 92-127.
. Anderson OM, Jordheim M. The
anthocyanins in Flavonoids chemistry,
Biochemistry and application.
Anderson O.M., Markhand K.R. Eds.
CRC Press; Boca, Raton, FL, 2006
;471-552.
. Stalikas CD. Extraction, separation
and detection methods for phenolic
acids and flavonoids. J Sep Sci 2007;
: 3268-3295.
. Ozyurt D, Ozturk BD, Apak R.
Determination of total flavnoid content
of Urtica dioica L. by a new method.
Adnan Menderes University, 4th
AACD Congress, Turkey,
Proceedings book. 2004.
. Braca A, Sortino C, Politi M, Morelli I,
Mendez J. Antioxidant activity of
flavonoids from Licania licaniaeflora. J
Ethnophar 2002 ;79: 379-381.
. Pourmorad F, Hosseinimehr SJ,
Shahabimajd N. Antioxidant activity,
phenol and flavonoid contents of
some selected Iranian medicinal
plants. African Journal of
Biotechnology 2006;5 (11): 1142-
. Schuler P. Natural antioxidants
exploited commercially, In Food
Antioxidants, Hudson BJF (ed.).
Elsevier, London1990; 99-170.
. Chu Y. Flavonoid content of several
vegetables and their antioxidant
activity. J Sci Food and Agricul 2000;
: 561-566.
. Koleva II, Van Beek TA, Linssen JPH,
de Groot A, Evstatieva LN. Screening
of plant extracts for antioxidant
activity: a comparative study on three
testing methods. Phytochemical
Analysis 2002 ;13: 8-17.
. Mantle D, Eddeb F, Pickering AT.
Comparison of relative antioxidant
activities of British medicinal plant
species in vitro. J Ethnopharmacol
; 72: 47- 51.
. Oke JM, Hamburger MO. Screening
of some Nigerian medicinal plants for
antioxidant activity using 2, 2-
diphenyl- picryl- hydrazyl radical.
African J Biomed Res 2002;5: 77- 79.
. Madhavachetty K, Sivaji K, Tulasi Rao
K. Flowering plants of Chittoor
districtăAndhra Pradesh, India.
Published by Students Offset Printers,
Tirupati 2008;34-35.
. Patil KS, Kenia R, Chaturvedi SC.
Anti-ulcer activity of stembark of
Shorea tumbuggaia. J Natural Reme
;4: 86222.
. Ankanna S, Savithramma N.
Evaluation of secondary metabolites
of Shorea tumbuggaia Roxb. a
globally threatened medicinal tree
taxa of Sheshachalam biosphere
reserve. Int J Phar Pharma Sci 2011
;3(5): 403-405.
. Ankanna S, Savithramma N.
Quantitative analysis of some
secondary metabolites of Shorea
tumbuggaia Roxb. ă an endemic,
endangered and globally threatened
medicinal tree species. J Pharm Res
;4(10): 3582-3584.
. Savithramma N. Shorea tumbuggaia
Roxb. An endemic endangered and
medicinal tree taxon under threat.
Non-wood News 2011;22: 49.
. Ruch RJ, Cheng SJ, Klauning JE.
Prevention of cytoxicity and inhibition
of intercellular communication
antioxidant catechins isolated from
Chinese green tea. Carcinogenesis
;10: 1003-1008.
. Grow-Chin Y, Hui-Yin C. Antioxidant
activity of various tea extracts in
relation to their antimutagenicity. J
Agri Food Chem 1995 ;43: 27-32.
. Hatano T, Kagawa H, Yashuhara T,
Okuda T. Two new flavonoids and
other constituents in licorice roots:
their relative astringency and radial
scavenging effects. Chemical and
Pharmacological Bulletin 1988 ;36:
-7.
. Aaby K, Ekeberg D, Skrede G.
Characterization of Phenolic
compounds in Strawberry fruits by
different HPLC detectors and
contribution of individual compounds
to total anti oxidant capacity. J Agric
Food Chem 2007 ;55: 4395-4406.
. Savarese M, Demarco E, Sacchi R.
Characterization of Phenolic extracts
from Olives (Olea europaea V. Piscio
Ttana) by electrospray ionization
mass spectrometry. Food chemistry
;105: 761-770.
. Hossain MB, Dilip K, Brumton, Nigel,
Martin-Diana A, Barry-Ryan-C.
Characterization of phenolics
composition Pu Laniaceae spices by
LC-ESI-MS/MS. J Agric Food Chem
;58(19): 10576-10581.
. Roman DA, Gomez CAM, Gomez
RM, Segarai CA, Fernandez GA .
Identification of phenolic compounds
in rose mary honey using solid phase
extraction by capillary electrophoresisESI-MS. J Pharmaceutical Biomedical
Analysis2006; 41: 1648-1656.
. Mertz C, Cheynier V, Gunata Z, Brat
P Analysis of Phenolic compounds in
two Black berry species by HPCC with
DAD and Electro spray Ion. Trap
mass spectrometry. J Agric Food
Chem 2007 ; 55: 8616-8624.
. Cardoso SM, Guyot S, Marnet N,
Lopes-da-silva JA, Renard CMGC,
Coimbra, MA. Characterization of
Phenolic extracts from Olive Pulp and
Olive Pomace by electrospray mass
spectrometry. J. of the Science of
Food and Agriculture, 2005;85, 21-32.
. Regalado EL, Sebastian, T, Jorge AP,
Peter et al., Isolation & identification of
phenolic compounds from rum aged in
oak barrels by high speed counter
current chromatography / HPLCDADESIMS and screening for antioxidant
activity. J Chromatography A.
;1218 :7358-7364.
. Mullen W, Yokota T, Lean MEJ,
Crozier A. Analysis of ellagitannins
and conjugates of ellagic acid and
quercetin in raspberry fruits by LCMS.
Phytochemistry 2003;64: 617-624.
. Soong YY, Philip JB. Qualification of
gallicacid and ellagic acid from longan
seed and mango kernel and their
effects on antioxidant activity. Food
Chemistry 2006 ;524-530.
. Zhang Y, Shi P, Haibin Q, Cheng Y.
Characterization of phenolic
compounds in Erigevon breviscapus
by liquid chromatography coupled to
electrospray ionization mass
pectrometry. Rapid. Communication in
Mass spectrometry 2007;21: 2971-
. Magalhaes PJ, Vieira JS, Goncalves
LM, Pacheco JG, Guido LF, Barros
AA. Isolation of phenolic compounds
from hop extracts using
polyvinylpolypyrrolidone:
characterization by high-performance
liquid chromatography-diode array
detection-electrospray tandem mass
spectrometry. J Chromatogr A
;1217 (19): 3258-3268.
. Nour-Eddine-ES Safi Plant
Polyphenols: Extraction structural
characterization, hemisynthesis acid
Antioxidant properties.
Phytochemicals as Nutracenticals
Global approaches to their role in
Nutrition and health. 2007;10: 181-
. Pandhair V, Shekhon BS. Reactive
oxygen species and antioxidants in
plants; An overview. J Plant
Biochemistry Biotechnolgoy 2006; 15:
-78.
. Sandhyarani DK, Potsangbam KS.
Poly phenolic compounds and free
radical scavenging activity in eight
Lamiaceae herbs of Manipur. 2011 ;3
(2), 108-113.
. Ferreres F, Raquel F, Sara B. Ines et
al. Identification of phenolic
compounds in isolated vacuoles of the
medicinal plant Catheranthus roseus
and their interaction with vacuolar
class. III Peroxidase an H2O2 affair, J
Exp Botany 2011 ;1-14.