Document Type : Original Article


1 Phytochemistry Research Laboratory, School of Pharmaceutical Education and Research, Jamia Hamdard, New Delhi-110 062, India

2 College of Pharmacy, Jazan University, Jazan, Saudi Arabia

3 Regional Research Institute of Unani Medicine, CCRUM, Aligarh, 202 001, India

4 Maharishi Arvind College of Pharmacy, Jaipur-302 023, India


Fraxinus excelsior L. (Oleaceae) is used to treat diarrhoea, dysentery, jaundice, joint pain, malaria, sores, swelling and wounds. The leaves of Senna sulfurea (Collad.) H. S. Irwin et Barneby (Leguminosae) are effective to cure blennorrhagia, diabetes, dysentery, gonorrhea and skin diseases. Prosopis cineraria (L.) Druce, (Fabaceae) is taken to alleviate anxiety, asthma, bronchitis, dysentery, dyspepsia, fever, leprosy, leucoderma, muscle tremors, piles, rheumatism and tremors. Our study was planned to isolate chemical constituents of the methanolic extracts obtained from the leaves of F. excelsior, S. sulfurea and P. cineraria and to characterized their structures. The air-dried plant materials were exhaustively extracted with methanol separately in a Soxhlet. The concentrated methanolic extracts were adsorbed on silica gel (60-120 mesh) for the preparation of slurries. The dried slurries were chromatographed over silica gel columns individually packed in petroleum ether. The columns were eluted with petroleum ether, chloroform and methanol successively in order of increasing polarity to isolate a variety of phytoconstituents. Phytochemical investigation of the leaves of F. excelsior afforded (Z,Z,Z)-n-tetratriacont-3,5,15-triene (1), n-hexatriacontane (2), (Z,Z,Z)-n-octatriacont-11,13,20-triene (3), phytanic acid (3,7,11,15-tetramethylhexadecanoic acid, 4), 26-hydroxystigmasterol-18-oic acid (5) and α-L-xylose (6). The leaves of S. sulfurea furnished isoliquiritigenin (7) and 4-methoxy-α-L-xylopyranosyl-(3→1′)-O-α-L-4′-methoxyxylopyranoside (di-4-methoxy-α-L-xyloside, 8). The leaves of P. cineraria on subjection to silica gel column chromatography led to isolate glyceryl-1-oleioyl-2-myristioyl-3-O-hydroxydihydrocinnamate (9), 2,3,4-trihydroxybenzyl n-hexadecanyl ether (10) and salicyloyl O-α-D-glucopyranosyl-2′-oleate (11). Their structures were established on the basis of spectral data analysis and chemical reactions.

Graphical Abstract

Chemical constituents from the leaves of Fraxinus excelsior L., Senna sulfurea (Collad.) H. S. Irwin et Barneby and Prosopis cineraria (L.) Druce


Akhtar, N., Ali, M., Alam, M.S., 2010. New steroidal glycosides from the stem bark of Mimusops elengi. Chem. Nat. Compd. 46(4), 549-553.
Anonymous, 2003. The Wealth of India-Raw Materials. NISCOM (CSIR), New Delhi, Vol. 4, p. 399.
Anonymous, 2012. Assessment report on Fraxinus excelsior L. or Fraxinus angustifolia Vahl, folium. European Medicine Agency. EMA/HMPC/239269/2011, London, United Kingdom. 1-16.
Bai, N., He, K., Ibarra, A., Bily, A., Roller, M., Chen, X., Ruhl, R., 2010. Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and PPARα activation activity. J. Nat. Prod. 73(1), 2-6.
Bruneton, J., 1999. Coumarins. In: Bruneton J. Pharmacognosy, Phytochemistry, Medicincal Plants. 2nd Edition. Lavoisier Publishing Inc., Paris. pp. 263-267.
Carnat, A., Lamaison, J.L., Duband, F., 1990. Teneurs en principaux constituants de la feuille de frêne, Fraxinus excelsior L. Plantes Méd Phytotér. 24, 145-151.
Damtoft, S., Franzyk, H., Jensen, S.R., 1992. Excelsioside, a secoiridoid glucoside from Fraxinus excelsior. Phytochemistry 31, 4197-4201.
Duke, J.A., Bogenschutz-Godwin, M.J., du Cellier, J., Duke, P.A.K., 2002. European ash (Fraxinus excelsior L.) In: Duke JA, Bogenschutz-Godwin MJ, duCellier J, Duke PAK. Handbook of Medicinal Herbs. CRC Press, Boca Ranton, London, New York, Washington D.C., p. 280.
Egan, P., Middleton, P., Shoeb, M., Byres, M., Kumarasamy, Y., Middleton, M., 2004. Gl 5, a dimer of oleoside, from Fraxinus excelsior (Oleaceae). Biochem. Syst. Ecol. 32, 1069-1071.
Ellinghaus, P., Wolfrum, C., Assmann, G., Spener, F., Seedorf, U., 1999. Phytanic acid activates the peroxisome proliferator-activated receptor α (PPARα) in sterol carrier protein 2-/sterol carrier protein x-deficient mice. J. Biol. Chem. 274(5), 2766-2772.
El-Sayed, M.M., Abdel- Aziz, M.M., Abdel-Gawad, M.M., Abdel-Hameed, E.S.S., Ahmed, W.S., Abdel-Lateef, E.E., 2013. Chemical constituents and cytotoxic activity of Cassia glauca Lam. leaves. Life Sci. J. 10(3), 1617-1625.
Gaedcke, F., 1993. Fraxinus. In: Hänsel, R., Keller, K., Rimpler, H., Schneider, G., 1993. editors. Hagers Handbuch der Pharmazeutischen Praxis. Drogen E-O, Springer-Verlag, Berlin, 5, 188-200.
Gangal, S., Sharma, S., Rauf, A., 2009. Fatty acid composition of Prosopis cineraria seeds. Chem. Nat. Comp. 45(5), 705-707.
Garg, A., Mittal, S.K., 2013. Review on Prosopis cineraria: A potential herb of Thar desert. Drug Invent. Today 5, 60-65.
Ghazanfar, S.A., Alsabahi, A.M.A., 1993. Medicinal plants of northern and central Oman (Arabia). Econ Bot. 47(1), 89-98.
Gruenwald, J., Brendler, T., Jaenicke, C., 2007. Ash, Faxinus excelsior. In: Gruenwald, J., Brendler, T., Jaenicke, C., Editors. PDR for herbal medicines. Thomson, pp. 53-54.
Hemlata, Kalidhar, S.B., 1994. Chemical composition of Cassia glauca Lam. Indian J. Pharmaceut. Sci. 56(1), 33-34.
Iossifova, T., Kostova, I., Evstatieva, L., 1997. Secoiridoids and hydroxycoumrains in Bulgarian Fraxinus species. Biochem. Syst. Ecol. 25, 271-274.
Janbaz, K.H., Haider, S., Imran, I., Zia-Ul-Haq, M., Martino, L.D., Feo, V.D., 2012. Pharmacological evaluation of Prosopis cineraria (L.) Druce in gastrointestinal, respiratory, and vascular disorders. Evidence-Based Complem. Altern. Med. doi:10.1155/2012/735653.
Jung, W.S., Chung, I.M., Ali, M., Ahmad, A., 2012. New steroidal glycoside ester and aliphatic acid from the fruits of Lycium chinensis. J. Asian Nat. Prod. Res. 14(4), 301-307.
Kerr G., 1998. A review of black heart of ash (Fraxinus excelsior L). Forestry 71(1), 49-56.
Khan, S.T., Riaz, N., Afza, N., Nelofar, A., Malik, A., Ahmed, E., Hussain, S., 2006. Studies on the chemical constituents of Prosopis cineraria. J. Chem. Soc. Pak. 28(6), 619-622.
Kittur, B.S., Srinivas, Y., Deshpande, S.R., 2015. Evaluation of leaf and stem extracts from Cassia glauca L. for antimicrobial activity. Int. J. Pure Appl. Zool. 3(1), 98-102.
Kostova, I., Iossifova, T., 2007. Chemical components of Fraxinus species. Fitoterapia 78, 85-106.
Kritikar, K.R., Basu, B.D., 1990. Indian Medicinal Plants, Periodical experts, New Delhi, pp. 910-911; p. 2333.
Kumar, D., Arora, S., Verma, A., 2013. Fatty acid composition and antimicrobial and antioxidant activity of Cassia glauca seed extracts. Int. J. Phytopharmacol. 4(2), 113-118.
Liu, Y., Singh, D., Nair, M.G., 2012. Pods of Khejri (Prosopis cineraria) consumed as a vegetable showed functional food properties. J. Funct. Foods. 4(1), 116-121.
Ma, C.-J., Li, G.-S., Zhang, D.-L., Liu, K., Fan, X., 2005. One step isolation and purification of liquiritigenin and isoliquiritigenin from Glycyrrhiza uralensis Risch. using high-speed counter-current chromatography. J. Chromatogr. A. 1078, 188-192.
Malik, A., Kalidhar, S., 2007. Phytochemical examination of Prosopis cineraria L. (Druce) leaves. Indian J. Pharmaceut. Sci. 69(4), 576-578.
Mustafa, A., Ali, M., 2011. New steroidal lactones and homomonoterpenic glucoside from fruits of Malva sylvestris L. Acta Poloniac Pharmac. Drug Res. 68(3), 393-401.
Nadkarni, K.M., 2000. Indian Materia Medica, Vol. 1, Popular Prakashan, Mumbai, India, 290, 1011-1014.
Oddo, E., Saiano, F., Alonzo, G., Bellini, E., 2002. An investigation of the seasonal pattern of mannitol content, in deciduous and evergreen species of the Oleaceae grooving in northern Sicily. Ann. Bot. 90, 239-243.

Quattrocchi, U., 2012. CRC World Dictionary of Medicinal and Poisonous Plants: Common Names, Scientific Names, Eponyms, Synonyms, and Etymology. CRC Press, Boca Raton, Florida, 3417.

Rai, K.N., Kaushalendra, K., Singh, J., 1997. Chemical constituents from the pods of Cassia glauca Lam. Asian J. Chem. 9(3), 558-560.

Sanz, M., de Simón, B.F., Cadahía, E., Esteruelas, E., Muñoz, A.M., Hernández , T., Estrella, I., Pinto, E., 2012. LC-DAD/ESI-MS/MS study of phenolic compounds in ash (Fraxinus excelsior L. and F. americana L.) heartwood. Effect of toasting intensity at cooperage. Mass Spectrom. 47(7), 905-918.

Sato, Y., He, J.X., Nagai, H., Tani, T., Akao, T., 2007. Isoliquiritigenin, one of the antispasmodic principles of Glycyrrhiza ularensis roots, acts in the lower part of intestine.Biol Pharm. Bull.30(1), 145-149.
Seki, K., Hashimoto, S.,  Sato, N.,  Harada, Y.,  Ishii, K.,  Inokuchi, H.,  Kanbe, J.-I., 1977. Vacuum-ultraviolet photoelectron spectroscopy of hexatriacontane (nC36H74) polycrystal: A model compound of polyethylene. J. Chem. Physics. 66, 3644.
Sharma, S., Soni, P.L., 1994. Structural investigation of Prosopis cineraria (Kherzi) seed galacto-mannan. Indian J. Chem. 33B, 355-361.
Sultana, S., Ali, M., Mir, S.R., 2018. Chemical constituents from the aerial parts of Jasminum auriculatum Vahl and seeds of Holarrhena pubescens Wall. ex G. Don. Acta Sci. Pharm. Sci. 2(3), 16-21.
Tahirović, A., Bašić, N., 2016. Determination of phenolic content and antioxidant capacity of Fraxinus excelsior L. and Fraxinus angustifolia Vahl. leaves and bark extracts. Rad. Šumar. fak. Univ. Sarajevu 46(1), 29-41.
Usvalampi, A., Turunen, O., Valjakka, J., Pastinen, O., Leisola, M., Nyyssölä, A., 2012. Production of L-xylose from L-xylulose using Escherichia coli L-fucose isomerase. Enzyme Microb. Tech. 50, 71-76.
Warrier, P.K., Nambiar, V.P.K., Ramankutty, C., 1996. Indian Medicinal Plants: A Compendium of 500 species. Orient Longman Pvt. Ltd., Hyderabad, p. 423.
van den Brink, D.M., Wanders, R.J.A., 2006. Phytanic acid: production from phytol, its breakdown and role in human disease. Cell. Mol. Life Sci. 63(15), 1752-1765.
Yassa, N., Masoomi, F., Rankouhi S.E.R., Hadjiakhoondi A., 2009. Chemical composition and antioxidant activity of the extract and essential oil of Rosa damascena from Iran, Population of Guilan. DARU J. Pharmac. Sci. 17(3), 175-180.