Chemical Constituents from the Stem Barks of Plumeria rubra L.

Document Type : Original paper

Authors

1 Department of Pharmacutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar (Haryana), India. Herbal Drug Technology, Delhi Pharmaceutical Science and Research University, Puspvihar, Sector 3, New Delhi, India.

2 Phytochemistry Research Laboratory, Faculty of Pharmacy, Jamia Hamdard, New Delhi, India.

3 Department of Pharmacutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar (Haryana), India.

4 Herbal Drug Technology, Delhi Pharmaceutical Science and Research University, Puspvihar, Sector 3, New Delhi, India. College of Pharmacy, Jazan University, Jazan, Saudi Arabia.

5 Herbal Drug Technology, Delhi Pharmaceutical Science and Research University, Puspvihar, Sector 3, New Delhi, India.

Abstract

Background and objectives: Plumeria rubra L. (Apocynaceae) is a deciduous shrub or small tree cultivated in subtropical and tropical countries.  Its bark is prescribed to treat amoebic dysentery,   dropsy, jaundice, scabies, gonorrhea, venereal affections and wounds. In the present research, we aimed to isolate and identify the chemical constituents of the bark of P.   rubra. Method: An air-dried bark powder of P. rubra was exhaustively extracted with methanol.  Methanol was removed afterwards under vacuum to get a dark brown mass. The extract was dissolved and adsorbed on silica gel (60-120 mesh) for preparation of slurry. The slurry was loaded over silica gel column packed in petroleum ether. The column was eluted with organic solvents successively in order of increasing polarity to isolate the chemical constituents. The structures of the phytoconstituents, isolated from the plant for the first time, have been elucidated by analyzing the spectral data and on the basis of chemical reactions. Results: Phytochemical investigation of a methanol extract of the stem bark led to isolate  n-octyl n-octadecanoate (n-octyl stearate, 1), lauryl-O-α-D-glucopyranosyl–(2ʹ→1ʹʹ)-O-β-D-glucopyranoside (lauryl diglucoside, 2), stearyl-α-L-xylopyranosyl–(2ʹ→1ʹʹ)-α-L-xlyopyranosyl-2ʹʹ-(3ʹʹ-oxy-4ʹʹʹ-hydroxy-5ʹʹʹ-methoxy)-benzoic acid (stearyl dixylosyl methoxygallic acid, 3), vanillic acid 4-O-β-D-arabinopyranosyl-(2a→1b)-O-β-D-arabinopyranosyl- (2b→1c)-O-β-D-arabino-pyranosyl-(2c→1d)-O-β-D-arabinopyranosyl-2d-stearate (vanillic acid 4-O-tetra-arabinosyl stearate, 4), vanillic acid 4-O- β-D-arabinopyranosyl-(2a→1b)-β-D-arabinopyranosyl-(2b→1c)-β-D-arabino- pyranosyl-(2c→1d)-β-D-arabinopyranosyl-(2d→1e)-β-D-arabinopyranosyl-(2e→1f)-β-D-arabino-pyranosyl-2f-stearate (vanillic acid 4-O-hexa-arabinosyl stearate, 5), β-D-glucopyranosyl-(2a→1b)-O-β-D-glucopyranosyl-(2b→1c)-O-β-D-glucopyranosyl- (2c→1d)-O-β-D- glucopyranosyl-(2d→1e)-O-β-D-glucopyranosyl-(2e→1f)-O-β-D- glucopyranoside (β-D-hexaglucoside , 6) and β-D-glucopyranosyl-(2a→1b)-O-β-D-glucopyranosyl-(2b→1c)-O-β-D- glucopyranosyl-(2c→1d)-O-β-D- glucopyranosyl-(2d→1e)-O-D- glucopyranosyl-(2e→1f)-O-β-D- glucopyranosyl-(2f→1g)-O-β-D-glucopyranosyl-(2g→1h)-O-β-D-rhamnopyranoside (β-D-heptaglucosyl-β-D-rhamnoside, 7). Conclusion: The stem bark of P.  rubra contained a variety of chemical constituents like  a fatty  ester, acyl  glycosides,  vanillic acid glycosides and polyglycosides. 

Keywords

Main Subjects


[1] Shinde PR, Patil PS, Bairagi VA. Phytopharmacological review of Plumeria species. Sch Acad J Pharm. 2014; 3(2): 217-227.
[2] Johnson T. CRCEthnobotany desk reference.  Boca Raton: CRC Press, 1999.
[3] National Institute of Science Communication and Information Resources (CSIR). The wealth of India- raw materials. New Delhi: NISCAIR (CSIR), 2005.
[4] Khare CP.  Indian medicinal plants. New York: Springer, 2007.
[5] Kirtikar KR, Basu BD. Indian medicinal plants. Allahabad: International Book Distributors, 1995.
[6] Nadkarni KM. Indian materia medica. Bombay: Popular Prakashan , 1976.
[7] Matthias O, Hamburger H, Geoffrey A, Cordell J, Nijsiri R.  Traditional medicinal plants of    Thailand: biologically active constituents of Plumeria rubra. J   Ethnopharmacol.  1991; 33(3): 289-292.
[8] Sharma G,  Chahar MK,  Dobhal S, Sharma N, Sharma TC,  Sharma MC,   Joshi YC,     Dobhal MP. Phytochemical constituents, traditional uses, and pharmacological properties of the genus Plumeria. Chem Biodivers. 2011; 8(8): 1357-1369.
[9] Tembare DR, Gurav S, Kumar S, Tamizhman T. A review of phytochemical constituents and pharmacological activity of Plumeria species. Int J Curr   Pharm Res. 2012; 4(1): 1-6.
[10] Kuigoua GM, Kouam SF, Ngadjui BT, Schulz B, Chaudhary MI, Krohn K. Minor secondary metabolic products from the stem bark of Plumeria rubra Linn. displaying antimicrobial activities. Planta Med. 2010; 76(6): 620-625.
[11] Rastogi Ram P, Mehrotra BN. Compendium of Indian medicinal plants. New Delhi: Lucknow & NISCAIR, 1993.  
[12] Akhtar N, Malik A.  Oleanene type triterpenes from Plumeria rubra. Phytochemistry. 1993; 32(6): 1523-1525.
[13] Kardono LB, Tsauri S, Padmawinata K, Pezzuto JM, Kinghorn AD. Cytotoxic   constituents   of the bark of Plumeria rubra collected in Indonesia. J Nat Prod. 1990;    53(6): 1447-1455.
[14] Akhtar N, Malik A, Ali SN, Kazmi SU. Rubrinol, an antimicrobial triterpene from Plumeria rubra. Fitoterapia. 1994; 65(2):162-166.
[15] Chen YH, Zang S. Xinhua bencao gangyao. Shanghai: Shanghi Science and Technology Press, 1991.
[16] Abe F, Chen RF, Yamauchi T. Studies on the constituents of Plumeria. Part I. Minor   iridoids from the roots of Plumeria acutifolia. Chem Pharm Bull. 1988; 36(8): 2784-2789.
[17] Gopi J, Khatri P, Singh N, Gaud H, Patel R. Phytochemical and pharmacological potential   of Plumeria rubra Linn. (Apocyanaceae): a review. Int J Pharm Sci. 2011; 3(1): 1162-1168.
[18] Choudhary M, Kumar V, Singh S. Phytochemical and pharmacological activity of genus Plumeria: an updated review. Int J Biomed Adv Res. 2014; 5(6): 266-271.
[19] Pino JA, Ferres A, Alvarez D, Rosado A. Volatiles of an alcoholic extract flowers from    Plumeria rubra L. var. acutifolia. Flav Fragr J. 1994; 9(6): 343-345.
[20] Zaheer Z, Konale AG, Patel KA, Khan S, Ahmed RZ. Comparative phytochemical screening of flowers of Plumeria alba and Plumeria rubra.  Asian J Pharm Clin Res.  2010; 3(4): 88-89. 
[21] Lawal OA, Ogunwande IA, Opoku AR. Chemical composition of essential oils of   Plumeria rubra L. grown in Nigeria. European J Med Plants. 2015; 6(1): 55-61. 
[22] Tohar N, Awang K, Mohd MA, Jantan I. Composition of the essential oils of four   Plumeria species grown in Peninsular Malaysia. J Essent Oil Res. 2006; 18(6):  613-617.
[23] Tohar N, Mohd MA, Jantan I, Awang K. A comparative study of the essential oils of the   genus Plumeria Linn. from Malaysia.  Flav Fragr J. 2006; 21(6): 859-863.
[24] Yan-Qing L, Hong-Wu W, Shou-Lian W, Zijun Y. Chemical composition and    antimicrobial activity of the essential oils extracted by microwave-assisted hydrodistillation   from the flowers of two Plumeria species. Anal Lett. 2012; 45(16):  2389-2397.  
[25] Zhang L, Liu H, Chen J. Essential oil extraction from Plumeria rubra L. cv. acutifolia   and analysis of its constituents. HuagongJishu Yu Kaifa. 2010; 39(6): 39-40.
[26] Byamukama R, Jane N, Monica J, oyvind MA, Bernard TK. Anthocyanins   from    ornamental flowers of red frangipani, Plumeria  rubra. Sci Horticult. 2011; 129(4):  840-843.
[27] Obuzor GU, Nweke HC. Analysis of essential oil of Plumeria rubra from Port Harcourt, Nigeria. J Chem Soc Nigeria. 2011; 36(1): 56-60.