Mycobiology

The Korean Society of Mycology (한국균학회)
권호 표지
DOI QR코드

DOI QR Code

Antimicrobial and Cytotoxic Activity of Di-(2-ethylhexyl) Phthalate and Anhydrosophoradiol-3-acetate Isolated from Calotropis gigantea (Linn.) Flower

  • Habib, M. Rowshanul (Department of Biochemistry and Molecular Biology, Rajshahi University) ;
  • Karim, M. Rezaul (Department of Biochemistry and Molecular Biology, Rajshahi University)
  • Published : 2009.03.31
Download PDF
⟨ Previous Next ⟩

Abstract

A phytochemical study on the flower of Calotropis gigantea (Linn.) using silica gel column chromatography and preparative thin layer chromatography, led to the first time isolation of Di-(2-ethylhexyl) phthalate (compound 1) and anhydrosophoradiol-3-acetate (compound 2). The structures of these compounds were confirmed by spectroscopic analyses (IR, HRTOFMS and NMR). The antibacterial and antifungal activities of ethyl acetate extract, compound 1 and compound 2 were measured using the disc diffusion method. Ethyl acetate extract and compound 1 presented better results than compound 2. The minimum inhibitory concentrations (MICs) of the extract and compounds were found to be in the range of $16{\sim}128{\mu}g/ml$. The cytotoxicity ($LC_{50}$) against brine shrimp nauplii (Artemia salina) were also evaluated and found to be 14.61 ${\mu}g/ml$ for ethyl acetate, 9.19 ${\mu}g/ml$ for compound 1 and 15.55 ${\mu}g/ml$ for compound 2.

Keywords

References

  1. Adak, M., and Gupta, J. K. 2006. Evaluation of anti-inflammatory activity of Calotropis gigantea (AKANDA) in various biological systems. Nepal. Med. Coll. J. 8:156-61
  2. Anjaneyulu, V. and Row, L. R. 1968. The triterpenes of Calotropis gigantea Linn. Curr. Sci. 6:156-157
  3. Amade, P., Mallea, M. and Bouaicha, N. 1994. Isolation, structure identification and biological activity of two metabolites produced by Penicillum olsonii Bainier and Sartory. J. Antibiot. 47:201-207 https://doi.org/10.7164/antibiotics.47.201
  4. Argal, A. and Pathak, A. K. 2006. CNS activity of Calotropis gigantea roots. J. Ethnopharmacol. 106:142-145 https://doi.org/10.1016/j.jep.2005.12.024
  5. Basile, A., Giordano, S. Lopez-Saez, J. A. and Cobianchi, R. C. 1999. Antibacterial activity of pure flavonoids isolated from mosses. Phytochemistry 52:1479-1482 https://doi.org/10.1016/S0031-9422(99)00286-1
  6. Basu, K. P. and Nath, M. C. 1934. Calosterol, a sterol present in the milky juice of Calotropis gigantea. Biochem. J. 28:1561-1564 https://doi.org/10.1042/bj0281561
  7. Chitme, H.R., Chandra, R. and Kaushik, S. 2005. Evaluation of antipyretic activity of Calotropis gigantea (Asclepiadaceae) in experimental animals. Phytother. Res. 19:454-456 https://doi.org/10.1002/ptr.1672
  8. Chitme, H. R., Chandra, R. and Kaushik, S. 2004. Studies on anti-diarrhoeal activity of Calotropis gigantea R.Br. in experimental animals. J. Pharm. Pharm. Sci. 7:70-75
  9. Ghani, A., 2003. Medicinal Plants of Bangladesh, pp. 141. Asiatic Society of Bangladesh, Dhaka
  10. Gourlay, T., Samartzis, I., Stefanou, D. and Taylor, K. 2003. Inflammatory response of rat and human neutrophils exposed to di-(2-ethyl-hexyl)-phthalate-plasticized polyvinyl chloride. Artificial Organs 27:256-260 https://doi.org/10.1046/j.1525-1594.2003.07107.x
  11. Gupta, J. and Ali, M. 2000. Rare chemical constituents from Calotropis gigantea roots. Indian. J. Pharm. Sci. 62:29-32
  12. Habib, M. R., Nikkon, F., Rahman, M., Haque, M.E. and Karim, M.R. 2007. Isolation of stigmasterol and β-sitosterol from methanolic extract of root bark of Calotropis gigantea (linn). Pakistan J. Biol. Sci. 10:4174-4176 https://doi.org/10.3923/pjbs.2007.4174.4176
  13. Karaman, I., Sahin, F., Gulluce, M., Ogutcu, H., Sngul, M. and Adiguzel, A. 2003. Antimicrobial activity of aqueous and methanol extracts of Juniperus oxycedrus L. J. Ethnopharmacol. 85:231-235 https://doi.org/10.1016/S0378-8741(03)00006-0
  14. Kartikar, K. R. and Basu, N. 1994. Indian Medicinal Plants, pp.1607 Lolit Mohan Basu, Allahabad, India
  15. Kim, M., Lee, H., Hahm, K., Moon, Y. and Woo, E. 2004. Pentacyclic triterpenoids and their cytotoxicity from the stem bark of Styrax japonicas. et Z. Arch. Pharm. Res. 27:283-286 https://doi.org/10.1007/BF02980060
  16. Kitagawa, I., Zhang, R. S., Park, J. D., Baek, N. I., Takeda, Y., Yoshikawa, M. and Shibuya, H. 1992. Indonesian medicinal plants. I. Chemical structures of calotroposides A and B, two new oxypregnane-oligoglycosides A and B, from the root of Calotropis gigantea (Asclepiadaceae). Chem. Pharm. Bull.(Tokyo) 40:2007-2013 https://doi.org/10.1248/cpb.40.2007
  17. Kiuchi, F., Fukao, Y., Maruyama, T., Obata, T., Tanaka, M., Sasaki, T., Mikage, M., Haque, M. E. and Tsuda, Y., 1998. Cytotoxic principles of a Bangladeshi crude drug, akond mul (roots of Calotropis gigantea L.). Chem. Pharm. Bull. (Tokyo) 46:528-530 https://doi.org/10.1248/cpb.46.528
  18. Lee, K. H., Kim, J. H., Lim, D. S. and Kim, C. H. 2000. Antileukaemic and anti-mutagenic effects of Di-(2-ethylhexyl) phthalate isolated from Aloe vera Linn. J. Pharm. Pharmacol. 52:593-598 https://doi.org/10.1211/0022357001774246
  19. Lhinhatrakool, T. and Sutthivaiyakit, S. 2006. 19-Nor- and 18, 20-epoxy-cardenolides from the leaves of Calotropis gigantea. J. Nat. Prod. 69:1249-51 https://doi.org/10.1021/np060249f
  20. Mavar-Manga, H., Haddad, M., Pieters, L., Baccelli, C., Penge, A. and Quetin-Lectercq, J. 2008. Anti-inflammatory compounds from leaves and root of Alchornea cordifolia (Schumach. & Thonn.) Müll. Arg. J. Ethnopharmacol. 115:25-29 https://doi.org/10.1016/j.jep.2007.08.043
  21. Meyer, B. N., Ferrigni, N. R., Putnam, J. E., Jacobsen, L. B., Nichols, D. E. and Mclaughlin J. L. 1982. Brine shrimp: a convenient general bioassay for active plant constituents, Planta. Med. 45:31-33 https://doi.org/10.1055/s-2007-971236
  22. Mueen, A. K. K., Rana, A. C. and Kixit, V. K. 2005. Calotropis species (Asclepiadaceae)-A comprehensive review. Pharmacognosy Magazine 1:48-52
  23. Mukherjee, P. K., Saritha, G. S. and Suresh, B. 2002. Antimicrobial potential of two different Hypericum species available in India. Phytother. Res. 16:692-695 https://doi.org/10.1002/ptr.1016
  24. Oie, L., Hersoug, L. G. and Madsen, J. O. 1997. Residential exposure to plasticizers and its possible role in the pathogenesis of asthma. Environ. Health Perspect. 105:972-978 https://doi.org/10.2307/3433878
  25. Pari, K., Rao, P. J., Devakumar, C. and Rastogi, J. N. 1998. A novel insect antifeedant nonprotein amino acid from Calotropis gigantea. J. Nat. Prod. 61:102-104 https://doi.org/10.1021/np970255z
  26. Pathak, A. K. and Argal, A. 2007. Analgesic activity of Calotropis gigantea flower. Fitoterapia 78:40-42 https://doi.org/10.1016/j.fitote.2006.09.023
  27. Rao, G. N., Kumar, P. M., Dhandapani, V. S., Krishna, T. R. and Hayashi, T. 2000. Constituents of Cassia auriculata. Fitoterapia 71:82-83 https://doi.org/10.1016/S0367-326X(99)00108-2
  28. Reiner, R. 1982. Detection of antibiotic activity. In: Antibiotic - An Introduction, pp. 21-27. Roche Scientific Services, Switzerland
  29. Rois, J. J., Reico, M. C. and Villar A. 1988. Antimicrobial Screening of natural products, J. Enthopharmocol. 23:127-149 https://doi.org/10.1016/0378-8741(88)90001-3
  30. Sastry, V. M. V. S. and Rao, G. R. K. 1995. Dioctyl phthalate and antibacterial compound from the marine brown alga-Sargassum wightii. J. Appl. Phycol. 7:185-186 https://doi.org/10.1007/BF00693066
  31. Sen, S., Sahu, N. P. and Mahato, S. B. 1992. Flavonol glycosides from Calotropis gigantea. Phytochemistry 31:2919-2921 https://doi.org/10.1016/0031-9422(92)83668-O
  32. Shibuya, H., Zhang, R., Park, J. D., Back, N. I., Takeda, Y., Yoshikawa, M. and Kitagawa, I. 1992. Chemical structures of Calotroposides C, D, E, F and G, five additional new oxypregnane-oligoglycosides from the root of Calotropis gigantea(Asclepiadaceae). Chem. Pharm. Bull. 40:2647-2653 https://doi.org/10.1248/cpb.40.2647
  33. Thakur, S., Das, P., Itoh, T., Imai, K. and Matsumoto, T. 1984. Latex extractables of Calotropis gigantea. Phytochemistry 23:2085-2087 https://doi.org/10.1016/S0031-9422(00)84985-7
  34. Toth-Soma, L. T., Gulyas, S., Szegletes, Z. 1993. Functional connection between and extracellular secretion in species of Euphorbia genus. Acta. Biol. Hung. 44:433-443

Cited by

  1. Structure and Biological Activity of Several Classes of Compounds from the Brown Alga Sargassum pallidum vol.49, pp.5, 2013, https://doi.org/10.1007/s10600-013-0781-z
  2. Isolation of antibacterial compounds from hairy vetch (Vicia villosa) against grapevine crown gall pathogen vol.54, pp.4, 2013, https://doi.org/10.1007/s13580-013-0028-8
  3. Biosynthesis of silver nanoparticles using Myristica fragrans seed (nutmeg) extract and its antibacterial activity against multidrug-resistant (MDR) Salmonella enterica serovar Typhi isolates vol.24, pp.17, 2017, https://doi.org/10.1007/s11356-017-9065-7
  4. Preparation, Characterization, Photocatalytic, Sensing and Antimicrobial Studies of Calotropis gigantea Leaf Extract Capped CuS NPs by a Green Approach vol.27, pp.S1, 2017, https://doi.org/10.1007/s10904-017-0672-z
  5. Review of the state of the art of preparative thin-layer chromatography vol.40, pp.4, 2017, https://doi.org/10.1080/10826076.2017.1294081
  6. Sedative and anxiolytic effects of ethanolic extract of Calotropis gigantea (Asclepiadaceae) leaves vol.4, pp.22211691, 2014, https://doi.org/10.12980/APJTB.4.2014C1147
  7. Antimicrobial activities of methanolic extract of Carissa opaca roots and its fractions and compounds isolated from the most active ethyl acetate fraction vol.5, pp.7, 2015, https://doi.org/10.1016/j.apjtb.2015.05.006
  8. vol.120, pp.1, 2018, https://doi.org/10.1002/jcb.27439