Chemical Composition of the Essential oil of The Leaves of Pimenta diocia (L.) Merr. & Pimenta racemosa (Mill.) cultivated in Egypt and Evaluation of Their in-vitro Antioxidant and Antidiabetic Activities
Keywords:
Pimenta diocia (L.) Merr., racemosa, essential oil, antioxidants, in-vitro antidiabetic, α-amylase, α-glucosidase, glucose uptake and yeast cellsAbstract
The aim of the study is to identify and characterize the chemical composition of the essential oil of both leaves of Pimenta diocia (L.) Merr. and Pimenta racemosa (Mill.) as well as to evaluate their in-vitro antioxidant and anti-diabetic potency. Both leaves essential oil was analyzed by GC-MS analysis. Different in-vitro antioxidant tests were employed, namely, 1,1-diphenyl-2-picrylhydrazyl (DPPH), ferric thiocyanate (FTC), ferric reducing antioxidant power, thiobarbituric acid (TBA) and β-carotene-linoleate bleaching assay. Also, the present work aims to evaluate the α-amylase and α-glucosidase inhibition as well as glucose uptake by yeast cells of essential oils. Essential oil analysis of the leaves of Pimenta racemosa (Mill.) showed high amounts of eugenol (37.95%), β-Myrecene (21.01%), α-Pinene (17.82%), linalool (6.15%) and limonene (5.93%). GC-MS data of leaves essential oil revealed the presence of eugenol (30.17%), limonene (17.24), α-Pinene (16.78%), linalool (9.71), 1,8 cineole (8.31%) and β-myrecene (5.21%) . Pimenta diocia (L.) Merr. and Pimenta racemosa (Mill.) leaves essential oil having antioxidant effect using various methods. In most of the oil samples and assays the antioxidant activity was higher than the one revealed by the positive control BHT. Both plants essential oil showed potent inhibition of α-Amylase at concentration 2.00 mg as it was inhibited by (75 and 63 %); with IC50 (0.95 and 1.13); respectively as well as inhibition of α-glucosidase enzyme by (61.42 and 53.00%) with IC50 (3.17 and 4.25); respectively. Also the percentage of glucose uptake by Pimenta diocia (L.) Merr. and Pimenta racemosa (Mill.) leaves essential oil at 2.00 mg/ml in the presence of 25 mM glucose is (63.49% and 49.61%); respectively. Conclusion: the present study clearly identified the Egyptian chemotype of Pimenta diocia (L.) Merr. and Pimenta racemosa (Mill.) leaves essential oil, it also displayed safe and promising antidiabetic and antioxidant properties. Therefore the essential oil of both species can be utilized as a natural antioxidant and antidiabetic as well as health benefits.
References
- Bailey LH, Manual of cultivated Plants. The Macmillan Company, New York (1968). [2]- Charles DJ. Simon JE. “Comparison of extraction methods for the rapid determination of essential oil content and composition of Basil”. Journal of the American Society for Horticultural Science, 115(1990), (458-462). [3]- Kapoor IPS. Chemistry and in vitro antioxidant activity of volatile oil and oleoresins of black pepper (Piper nigrum). Journal of Agricultural and Food Chemistry, 57 (2009), (5358-5364). [4]- Marques FA, Wendler EP, Baroni ACM, de Oliveira PR, Sasaki BS, Guerrero J. “Leaf essential oil composition of Pimenta pseudocaryophyllus (Gomes) L. R. Landrum native from Brazil”. Journal of Essential Oil Research, 22(2) (2010), (150-152). [5]- Rao PS, Navinchandra S, Jayaveera KN, “An important spice, Pimenta dioica (Linn.) Merill: A review”. International Current Pharmaceutical Journal, 1(8) (2012), (221-225). [6]- Paula JAM, Reis JB, Ferreira LHM, Menezes ACS, Paula JR. “Gênero Pimenta: aspectos botânicos, composição química e potencial farmacológico”. Revista Brasileira de Plantas Medicinais, 12(3) (2010), (363-379). [7]- Weiss EA. Spice Crops. New York: CABI Publishing, (2002): (131-132). [8]- Boning CR, “Native and Exotic Plants Grown for Scent and Flavor”. Florida's Best Herbs and Spices Florida: Pineapple Press Inc., 1st edn. (2010), (32-33). [9]- Contreras-Moreno B, Rojas J, Celis M, Rojas L, Méndez L, Landrum L. “Componentes volátiles de las hojas de Pimenta racemosa (Mill.) var. racemosa (Mill.) JW Moore (Myrtaceae) de Táchira–Venezuela”. Bol Latinoam Caribe Plant Med Aromat 13(3) (2014a), (305-310). [10]- Jirovetz L, Buchbauer G, Stoilova I, Krastanov A, Stoyanova A. “Spice Plants: Chemical Composition and Antioxidant Properties of Pimenta Lindl. Essential Oils. Part 1: Pimenta dioica (L.) Merr. Leaf oil from Jamaica”. Ernaehrung (Vienna, Austria) 31(2007): 55-62. [11]- Alitonou GA, Noudogbessi JP, Sessou P, Tonouhewa A, Avlessi F, Menut C, Sohounhloue DC “Chemical composition and biological activities of essential oils of Pimenta racemosa (Mill.) from Benin”. Int J Biosci 2(2012), (1-12). [12]- Leyva MI, Tacoronte JE, Navarro A, Montada D, Bello A, Marquetti MC “Estudio de laboratorio del aceite escencial de Pimenta racemosa (Myrtales: Myrtaceae) y su posible utilización para el control de Musca domestica (Diptera: Muscidae)”. Rev CENIC Ciencias Biológicas 38(1) (2007), (18-19). [13]- Tajkarimi MM, Ibrahim SA, Cliver DO “Antimicrobial herb and spice compounds in food”. Food Control 21(9) (2010), (1199-1218). [14]- Kim J, Lee YS, Lee SG, Shin SC, Park IK. “Fumigant antifungal activity of plant essential oils and components from West Indian bay (Pimenta racemosa (Mill.)) and thyme (Thymus vulgaris) oils against two phytopathogenic fungi”. Flavour Fragr J 23(4) (2008), (272-277). [15]- Nesrin S, Sevil O, Mahmut G, Kerim G, Osman EO, Moustafa MK “Determination of antimicrobial activity and chemical composition of pimento & ginger essential oil”. Indian J. Pharm. Educ. Res. 51(3) (2017), (230-233). [16]- El-Gizawy HA, Hussein MA. “Fatty acids Profile, Nutritional Values, Anti-diabetic and Antioxidant Activity of the Fixed Oil of Malva parviflora growing in Egypt”. International journal of Phytomedicine. 7(2015), (219-230). [17]- Patel DK, Kumar R, Prasad SK, Sairam K, Hemalatha S. “Antidiabetic and in vitro antioxidant potential of Hybanthus enneaspermus(Linn) F. Muell in streptozotocin induced diabetic rats”. Asian Pac J Trop Biomed. 1(4) (2011), (316- 322). [18]- Malviya N, Jain S, Malviya S. “Anti-diabetic potential of medicinal plants”. Acta Pol Pharm. 67(2) (2010), (113- 118). [19]- Jung M, Park M, Lee HC, Kang YH, Kang ES, Kim SK. “Antidiabetic agents from medicinal plants”. Curr Med Chem. 13(10) (2006), (1203-1218). [20]- Ponnusamy S, Ravindran R, Zinjarde S, Bhargava S, Kumar AR. Evaluation of traditional Indian anti-diabetic medicinal plants for human pancreatic amylase inhibitory effect in vitro. Evidence Based Complement Alternat Med 51(5) (2011), (647- 653). [21]- Shimada K, Fujikawa K, Yahara K, Nakamura T “Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion”. J Agric Food Chem 40(1992), (945- 948). [22]- Osawa T, Namiki T “A novel type of antioxidant isolated from leaf wax of Eucalyptus leaves”. J Agric Food Chem 45(1981), (735-739). [23]- Benzie IFF, Strain JJ. “The ferric reducing ability of plasma (FRAP) as a measure of “ antioxidant power : The FRAP assay” . Anal Biochem 239(1996), (70 – 76). [24]- Ottolenghi A “Thiobarbituric acid (TBA) method”. Arch Biochem Biophys 77(1959), (355). [25]- Velioglu YS, Mazza G, Gao L, Oomah BD. “Antioxidant activity and total phenolics in selected fruits, vegetables, and grain products”. J Agric Food Chem 46(1998): (4113-4117). [26]- Jayaprakasha GK, Sign RP, Sakariah KK “Antioxidant activity of grape seed (Vitis vinifera) extracts on peroxiation models in vitro”. Food Chem 73(2001), (285-290). [27]- Miller G. L. “Use of dinitrosalicylic acid reagent for determination of reducing sugar”. Analytical Chemistry, 31(1959), (426-428). [28]- Bachhawat A, Shihabudeen MS, Thirumurugan K. “Screening of fifteen Indian Ayurvedic plants for α- glucosidase inhibitory activity and enzyme kinetics”. International Journal of Pharmacy and Pharmaceutical Sciences 3(2011),(267-274). [29]- Cirillo VP. “Mechanism of Glucose Transport across the Yeast Cell Membrane”. J Bacteriol, 84(1962), (485–491). [30]- Tucker AO, Maciarello MJ, Landrum LR. “Volatile Leaf Oils of Caribbean Myrtaceae. II. Pimenta dioica (L.) Merr. of Jamaica”. Journal of Essential Oil Research, 3(3) (1991a): 195-196. [31]- Pino JA, Rosado A. “Chemical Compostion of the Leaf Oil of Pimenta dioica L. from Cuba”. Journal of Essential Oil Research, 8(3) (1996), (331-332). [32]- Tucker AO, Maciarello MJ, Landrum LR “Volatile leaf oils of Caribbean Myrtaceae. IV. Pimenta jamaicensis (Britton & Harris) Proctor of Jamaica”. J. Essent. Oil Res. 4(1) (1992a), (93-94). [33]- Tucker AO, Maciarello MJ, Adams RP, Landrum LR, Zanoni TA. “Volatile Leaf Oils of Caribbean Myrtaceae. I. Three varieties of Pimenta racemosa (Mill.) (Miller) J. Moore of the Dominican Republic and the commercial bay oil”. Journal of Essential Oil Research, 3(5) (1991b), (323-329). [34]- Bello A, Rodriguez ML., Castineira N, Urquiola A, Rosado A, Pino JA “Chemical Composition of the Leaf Oil of Pimenta racemosa (Mill.) J.Moore from Western Cuba”. Journal of Essential Oil Research, 7(1995), (423-424). [35]- Dolores G, Antonio A, Paz T, Angeles F, Teresa S. “Gas Chromatographic-Mass Spectrometry Study of the Essential Oils of Pimenta racemosa (Mill.) var. terbinthina and P. racemosa var. grisea” Verlag der Zeitschrift fur Naturforschung, Tubingen (2002). [36]- Yoshimura M, Amakura Y, Yoshida T. “Polyphenolic Compounds in Clove and Pimento and their Antioxidative Activities”. Biosci Biotech and Biochem J. 75(11) (2011): (2207-2212). [37]- El-gizawy HA and Hussein MA. “Isolation, Structure Elucidation of Ferulic and Coumaric acids from Fortunella japonica Swingle leaves and their Structure Antioxidant activity relationship”. Free radical and antioxidant. 7(1) (2017), (23-30). [38]- Zhou F, Ji B, Zhang H, Jiang H, Yang Z, Li J, Ren Y, Yan W. Synergistic effect of Thymol and carvacrol combined with chelators and organic acids against Salmonella Typhimurium. J. Food Prot. 70(2007): (1704-1709). [39]- Hussein MA. “A Convenient Mechanism for the Free Radical Scavenging Activity of Resveratrol”. International Journal of Phytomedicine 3(2011), (459-469). [40]- Hussein MA, El-gizawy HA, Gobba NA, Mosaad YO. “Synthesis of Cinnamyl and Caffeoyl Derivatives of Cucurbitacin-Eglycoside Isolated from Citrullus colocynthis Fruits and their Structures Antioxidant and Anti-inflammatory Activities Relationship”. Current Pharmaceutical Biotechnology. 18(2017), (677-693). [41]- Olivera P, Mila J and Mladen M. “Chemical Composition and Antioxidant Activity of Essential Oils of Twelve Spice Plants”. Croatica Chemica ACTA,79 (4) (2006), (545-552). [42]- Gulcin I, “Antioxidant activity of eugenol: a structure- activity relationship study”. Journal of Medicinal Food. Vol. (14) 9, (2011). [43]- Marshall JJ. Hypothesized that negatively charged residues of pilaic acid from membrane. Am Chem Soc Symposium Series. 15(1975), (244-66). [44]- Jaffe WG, Lette CLV. “Heat labile growth inhibiting factors in bens (Phaseolus vulgaris)”. J Nutr 94(1968), (203-10). [45]- Sima AAF, Chakrabarti S. Long term suppression of post prandial hyperglycemia with acarbose retards the development of neuropathies in the BB/W-rat. Diabetologia 35(2004), (325-30). [46]- Carrascosa JM, Molero JC, Fermin Y, Martinez C, Andres A, Satrustegui J. “Effect of chronic treatment with acarbose on glucose and lipid metabolism in obese diabetic wistar rats”. Diabetes Obes Metab 3(2001), (240-248). [47]- Teusink B., Diderich J.A., Westerhoff H.V., Van D.K. and Walsh M.C. Intracellular glucose concentration in derepressed yeast cells consuming glucose is high enough to reduce the glucose transport rate by 50%, J. Bacteriol., 180(1998), (556-562). [48]- Kannur DM, Hukkeri VI. and Akki KS. Antidiabetic activity of Caesalpinia bonducella seed extracts in rats, Fitoterapia, 77(2006), (546-549). [49]- Pyiyanka S, Ramesha H, Sachin B, Garikapati V, Arvind M, Atul A, Vihal S, Mahemud L, Rakesh S, Ramanamurthy B, Mahesh J, Hirekodathakallu V, Ashok p. “Potential dual role of eugenol in inhibiting advanced glycation end products in diabetes: proteomic and mechanistic insights”. Scientific Reports 6(2016), Article No.: 18798. [50]- Murali R, Karthikeyan A, Saravanan R “Protective effects of D-limonene on lipid peroxidation and antioxidant enzymes in streptozotocin- induced diabetic rats”. Basic & Clin Pharmacol & Toxicol. 112 (3) (2013), (175-81). [51]- More TA, Kulkarni BR, Nalawade ML and Arvindekar AU. “Antidiabetic activity of linalool and limonene in streptozotocin-induced diabetic rat: a combinatorial therapy approach,” International Journal of Pharmacy and Pharmaceutical Sciences, 6,(8) (2014), (159–163). [52]- Shukla S., Mehta P., Mehta A., Vyas S.P. and Bajpai V.K. “Preliminary phytochemical and antifungal screening of various organic extracts of Caesalpinia bonducella seeds”, Romanian Biotechnological Letters, 16(2011), (6384- 6389).
