Isaac Scientific Publishing

Modern Organic Chemistry Research

Phytochemical Investigation of the Stem Bark of Tecomella Undulata (Sm.) Seem

Download PDF (382.7 KB) PP. 159 - 171 Pub. Date: November 1, 2017

DOI: 10.22606/mocr.2017.24002

Author(s)

  • Mohammed Ali*
    Phytochemistry Research Laboratory, Faculty of Pharmacy, Jamia Hamdard, New Delhi - 110 062, India
  • Hameed Hasan Abra

    Phytochemistry Research Laboratory, Faculty of Pharmacy, Jamia Hamdard, New Delhi - 110 062, India
  • Shahnaz Sultana

    Phytochemistry Research Laboratory, Faculty of Pharmacy, Jamia Hamdard, New Delhi - 110 062, India; Present address: College of Pharmacy, Jazan University, Jazan, Saudi Arabia
  • Showkat Rassol Mir

    Present address: College of Pharmacy, Jazan University, Jazan, Saudi Arabia

Abstract

Tecomella undulata (Sm.) Seem. (Bignoniaceae) occurs as a shrub or small tree in southern Asia and Saudi Arabia and its stem bark is used in folklore medicine. Phytochemical investigation of a methanolic extract of the stem bark led to the isolation of ten compounds characterized as n- undecanyl octadecanoate (undecanyl stearate, 1), n-eicosanyl cinnamate (2), n-hexadecanyl caffeate (3), stigmast-5-en-3β-ol-3-O-β-D-arabinopyranosyl-4'4'→2a)-dihydrolapachyl-2', 3'-didecanoate (β-sitosterol arabinosyl dihydrolapachyl diester , 4), vanillic acid (5), 2,7-dimethoxy-3-(6'-hydroxynonan-1'-oxy)-naphtho-1,4-quinone (tecomellanaphtho-quinone A, 6), 2,7-dimethoxy-3-(12'-hydroxypentadecan-1'-oxy)-naphtho-1,4-quinone (tecomellanaphthoquinone B, 7), 2-n-tetracosanyl - 7,8 - dimethoxy - 3 - (1'',4'' – dimethoxy - 7''- hydroxy-(3 → 2'')-naphthyl) naphthoquinone (tetracosanyl undulatol, 8), 7,8-dimethoxy -3 (2')-(1',4'-dimethoxy-7'-hydroxyl-(3→2')- naphthyl)-naphthoquinone-7'-O-β-D-glucopyranosyl-(2a→1b)-O-β-D-glucopyranosyl-(2b→1c)-O-β-D-glucopyranosyl-(2c→1d)-O-β-D-glucopyranoside (undulatol teraglucoside, 9) and 4-hydroxy-3-methoxybenzoate 7-O-β-D-galacturunofuranosyl-(2a→1b)-O-β-D-glucofuranosyl-(2b→1c)-O-β-D-arabinopyranosyl-(2c→1d)-O-β-D-[(arabinopyranosyl)8]--(2k→1L)-O-β-D-arabinopyranoside (vanillic acid dodecaglycoside, 10). The structures of these phytoconstituents, isolated for the first time from the stem bark, have been established on the basis of spectral data analysis and chemical reactions.

Keywords

Tecomella undulata, stem bark, chemical constituents, isolation, structural elucidation.

References

[1] S. Arya, O.P. Toky, S.M. Harris and P.J.C. Harris, “Tecomella undulata (Rohira): a valuable tree of the thar desert,” International Tree Crops Journal, vol. 7, no. 3, pp. 139–147, 1992.

[2] Anonymous, “The Wealth of India; Raw materials”. NISCAIR, CSIR, New Delhi, 2005, vol. 10, pp. 130-133., 2005.

[3] R. Dhir and G.S. Shekhawat, “Critical review on Tecomella undulata: a medicinally potent endangered plant species of Indian Thar desert”, International Journal of Current Research, vol. 4, no. 6, pp. 36-44, 2012.

[4] S.S. Katewa and P.K. Galav, “Traditional herbal medicines from Shekhawati region of Rajasthan,” Indian Journal of Traditional Knowledge, vol. 4, pp. 237-245, 2005.

[5] A.K. Meena and M.M. Rao, “Folk herbal medicines used by the Meena community in Rajasthan,” Asian Journal of Traditional Medicine, vol. 5, no. 5, pp. 19-31, 2005.

[6] K.L. Meena and B.L. Yadav, “Studies on ethnomedicinal plants conserved by Garasia tribes of Sirohi district Rajasthan India,” Indian Journal of Natural Products and Resources, vol. 1, pp. 500-506, 2010.

[7] K.M. Nadkarni, “Indian Materia Medica,” Popular Prakashan: Mumbai, India, 2000, vol. 1, pp. 56-57.

[8] R.B. Tareen, T. Bibi, M.A. Khan, M, Ahmad and M. Zafar, “Indigenous knowledge of folk medicine by the women of Kalat and Khuzdar regions of Balochistan, Pakistan,” Pakistan Journal of Botany, vol. 42, pp. 1465-1485, 2010.

[9] R. Rohilla and M. Garg, “Phytochemistry and pharmacology of Tecomella undulata”, International Journal of Green Pharmacy, vol. 8, no. 1, pp. 1-6, 2014.

[10] P.B. Upadhyay, S. Roy and A. Kumar A, “Traditional uses of medicinal plants among the rural communities of Churu district in the Thar Desert, India,” Journal of Ethnopharmacology, vol. 113, pp. 387-399, 2007.

[11] S.R. Gupta, K.K. Malik, T.R. Seshadri, “Lapachol from the heartwood of Tecomella undulate and a note on its reaction,” Indian Journal of Chemistry, vol. 7, pp.457?459, 1969.

[12] K.C. Joshi, P. Singh and R.T. Pardasani, “Quinones and other constituents from the roots of Tecomella undulata,” Planta Medica, vol. 1977, vol. 31, pp. 14?16, 1977.

[13] K.C. Joshi, A.K. Sharma, P. Singh P, “A new ferulic ester from Tecomella undulata,” Planta Medica, vol. 40, pp. 71?72, 1986.

[14] D. Pandya, R.B. Dhankecha, K.D. Rathod, M.B. Dhameliya, T.R. Desai and V.L. Patel, “Pharmacognostic and Phytochemical evaluation of leaves of Tecomella undulata,” International Journal of Biological and Pharmaceutical Research, vol. 3, pp. 164?168, 2012.

[15] P. Singh, P. Khandelwal, N. Hara, T. Asai and Y.Fujimoto, “Radermachol and napthoquinone derivatives from Tecomella undulata complete 1H and 13C NMR assignments of radermachol with aid of computational 13C shift prediction”, Indian Journal of Chemistry, vol., 47B, pp. 1865?1870, 2008.

[16] M.M. Azam, “Anti-HIV agents and other compounds from Tecomella undulata,” Oriental Journal of Chemistry, vol. 15, pp. 375–377, 1999.

[17] M.M. Azam and A. Ghanim, “Tecomella undulata: A Potential of anti-AIDS agents,” Ann Arid Z, vol. 39, pp. 93-96, 2000.

[18] V.B. Pandey and B. Dasgupta, “A new ester glycoside from the bark of Tecomella undulata,” Experentia, vol. 26, pp. 1187?1188, 1970.

[19] V.K. Gujral, S.R. Gupta and A. Verma, “New chromone glycoside from Tecomella undulata,”

[20] K.S. Verma, G.R. Sood, S.R. Gupta and V.K. Gujral, “Structure and configuration of tecoside, a new irridoid glucoside from Tecomella undulata,” Journal of Chemical Society, Perkin Transaction, vol. 1, pp. 2473-2477, 1979.

[21] K.C. Joshi, L. Prakash and L.B. Singh, “6?O?veratryl catalposide: A new iridoid glycoside from Tecomella undulata,” Phytochemistry, vol. 14, pp. 1441?1442, 1975.

[22] C.P. Khare, “Indian Herbal Remedies, Rational western therapy, Ayurvedic and other traditional usage,” Society of new age herbals Publication, New Delhi, 2004, pp. 67-69.

[23] A.Q. Laghari, S. Memon, A. Nelofar and A.H. Laghari, “Structurally diverse alkaloids from Tecomella undulate G. Don flowers,” Journal of King Saudi University Science, vol. 26, pp. 300-304, 2014.

[24] N. Akhtar, M. Ali and M.S. Alam, “New steroidal glycosides from the stem bark of Mimusops elengi,” Chemistry of Natural Compounds, vol. 46, no. 4, pp. 549-553, 2010.

[25] W.S. Jung, I.M. Chung, M. Ali and A. Ahmad, “New steroidal glycoside ester and aliphatic acid from the fruits of Lycium chinensis,” Journal of Asian Natural Product Research, vol. 14, no. 4, pp. 301-307, 2012.

[26] M. Mustafa and M. Ali, “New steroidal lactones and homomonoterpenic glucoside from fruits of Malva sylvestris L.,” Acta Poloniac Pharmaceutical Drug Research, vol. 68, no. 3, pp. 393-401, 2011.