Chemical Investigation and Antimicrobial Activity of Medicinal Plant Toddalia asiatica Lam

https://doi.org/10.22146/ijc.46643

Wilmar Maarisit(1*), Misran Lawani(2)

(1) Department of Pharmacy, Faculty of Mathematics and Natural Sciences, Christian University of Indonesia Tomohon, Jl. Raya Talete II Kuranga Tomohon, P.O. Box 112, Tomohon 95441, South Sulawesi, Indonesia
(2) Department of Agricultural Product Technology, Faculty of Agriculture, Khairun University, Jl. Raya Kampus Unkhair Gambesi Ternate, Ternate 97719, North Maluku, Indonesia
(*) Corresponding Author

Abstract


Medicinal plants have become important sources of natural products, which have been used in the development of therapeutic agents. Four new coumarins (1-4) have been isolated together with five known metabolites (5-9) from the medicinal plant T. asiatica. The structures of 1-9 were assigned based on their spectroscopic data. Compounds (1-9) inhibited the growth of the Gram-negative bacteria E. coli and Gram-positive bacteria S. aureus at a concentration of 25 and 50 μg/disc. Compounds (2-4) inhibited the phytopathogenic fungus C. cucurbitarum at 50 μg/disc.


Keywords


natural products; Toddalia asiatica; antimicrobial activity; NMR

Full Text:

Full Text PDF


References

[1] Orwa, J.A., Jondiko, I.J.O., Minja, R.J.A., and Bekunda, M., 2008, The use of Toddalia asiatica (L) Lam. (Rutaceae) in traditional medicine practice in East Africa, J. Ethnopharmacol., 115 (2), 257–262.

[2] Hirunwong, C., Sukieum, S., Phatchana, R., and Yenjai, C., 2016, Cytotoxic and antimalarial constituents from the roots of Toddalia asiatica, Phytochem. Lett., 17, 242–247.

[3] Hu, J., Shi, X., Chen, J., Mao, X., Zhu, L., Yu, L., and Shi, J., 2014, Alkaloids from Toddalia asiatica and their cytotoxic, antimicrobial and antifungal activities, Food Chem., 148, 437–444.

[4] Ishii, H., Kobayashi, J.I., Sakurada, E., and Ishikawa, T., 1992, The absolute stereochemistries of (+)-toddalolactone and its related chiral coumarins from Toddalia asiatica (L.) Lam. (T. aculeata Pers.) and their optical purities, J. Chem. Soc., Perkin Trans. 1, 13, 1681–1684.

[5] Kokwaro, J.O., 1993, Medical Plants of East Africa, Kenya Literature Bureau, Nairobi, 212.

[6] Ishii, H., Kobayashi, J., Ishikawa, M., Haginiwa, J., and Ishikawa, T., 1991, Studies on the chemical constituents of rutaceae++ plants LXVI. The chemical constituents of Toddalia asiatica l. Lam. Toddalia aculeata (L.) Lam. (T. Aculeata Pers.) (1). Chemical constituents of the root bark, Yakugaku Zasshi, 111 (7), 365–375.

[7] Combes, G., and Gaignault, J.C., 1984, The coumarins in Toddalia asiatica, Fitoterapia, 55 (3), 161–170.

[8] Zhang, X., Sun, W., Yang, Z., Liang, Y., Zhou, W., and Tang, L., 2017, Hemostatic chemical constituents from natural medicine Toddalia asiatica root bark by LC-ESI Q-TOF MS, Chem. Cent. J., 11, 55.

[9] Li, W., Zhang, J.S., Huang, J.L., Jiang, M.H., Xu, Y.K., Ahmed, A., Yin, S., and Tang, G.H., 2017, New prenylated coumarins from the steams of Toddalia asiatica, RSC Adv., 7 (49), 31061–31068.

[10] Liu, Y., Guo, J., Xiao, Z., Peng, D., and Song, K., 2020, Adsorption of chelerythrine from Toddalia asiatica (L.) Lam. by ZSM-5, Adv. Polym. Technol., 2020, 9408921.

[11] Irudayaraj, S.S., Sunil, C., Duraipandiyan, V., and Ignacimuthu, S., 2013, In vitro antioxidant and antihyperlipidemic activities of Toddalia asiatica (L) Lam. leaves in Triton WR-1339 and high fat diet induced hyperlipidemic rats, Food Chem. Toxicol., 60, 135–140.

[12] Thirugnanasampandan, R., Jayakumar, R., and Prabhakaran, M., 2012, Analysis of chemical composition and evaluation of antigenotoxic, cytotoxic and antioxidant activities of essential oil of Toddalia asiatica (L.) Lam., Asian Pac. J. Trop. Biomed., 2 (3), S1276–S1279.

[13] Balasubramaniam, A., Manivannan, R., Paramaguru, R., Mazumder, P.M., and Vijayakumar, M., 2012, Evaluation of anti-inflammatory and antioxidant activities of Stem Bark of Toddalia asiatica (L.) Lam. using different experimental models, Pharmacologia, 3 (5), 144–149.

[14] Ceballos, R., Sankoli, S.M., Ramnath, S., Venkataramegowda, S., Murthy, G.S., and Ceballos R.M., 2013, Evaluation of phytochemicals and in vitro antioxidant studies of Toddalia asiatica leaf, J. Med. Plants, 5 (4), 202–205.

[15] Vázquez, R., Riveiro, M.E., Vermeulen, M., Mondillo, C., Coombes, P.H., Crouch, N.R., Ismail, F., Mulholland, D.A., Baldi, A., Shayo, C., and Davio, C., 2012, Toddaculin, a natural coumarin from Toddalia asiatica, induces differentiation and apoptosis in U-937 leukemic cells, Phytomedicine, 19 (8-9), 737–746.

[16] Shan, X.F., Meng, Q.F., Kang, Y.H., Bian, Y., Gao, Y.H., Wang, W.L., and Qian, A.D., 2011, Isolation of active compounds from methanol extracts of Toddalia asiatica against Ichthyophthirius multifiliis in goldfish (Carassius auratus), Vet. Parasitol., 199 (3-4), 250–254.

[17] Borah, R., Kalita, M.C., Kar, A., and Talukdar, A.K., 2010, Larvicidal efficacy of Toddalia asiatica (Linn.) Lam against two mosquito vectors Aedes aegypti and Culex quinquefasciatus, Afr. J. Biotechnol., 9 (16), 2527–2530.

[18] Stephen, I.S., Sunil, C., Duraipandiyan, V., and Ignacimuthu, S., 2012, Antidiabetic and antioxidant activities of Toddalia asiatica (L.) Lam. leaves in Streptozotocin induced diabetic rats, J. Ethnopharmacol., 43 (2), 515–523.

[19] Kimang’a, A., Gikunku, J., Kariuki, D., and Ogutu, M., 2015, Safety and analgesic properties of ethanolic extracts of Toddalia asiatica (L) Lam. (Rutaceae) used for central and peripheral pain management among the East African ethnic communities, Ethiop. J. Health Sci., 26 (1), 55–64.

[20] Lin, T.T., Huang, Y.Y., Tang, G.H., Cheng, Z.B., Liu, X., Luo, H.B., and Yin, S., 2014, Prenylated coumarins: Natural phosphodiesterase-4 inhibitors from Toddalia asiatica, J. Nat. Prod., 77 (4), 955–962.

[21] He, N., Wang, P., Wang, P., Ma, C., and Kang, W., 2018, Antibacterial mechanism of chelerythrine isolated from root of Toddalia asiatica (Linn) Lam, BMC Complement Altern. Med., 18, 261.

[22] Karunai, R.M., Balachandran, C., Duraipandiyan, V., Agastian, P., and Ignacimuthu, S., 2012, Antimicrobial activity of Ulopterol isolated from Toddalia asiatica (L.) Lam. A traditional medicinal plant, J. Ethnopharmacol., 140 (1), 161–165.

[23] Roy, P.K., Maarisit, W., Roy, M.C., Taira, J., and Ueda, K., 2012, Five new diterpenoids from an Okinawan soft coral, Cespitularia sp., Mar. Drugs, 10 (12), 2741–2748.

[24] Maarisit, W., and Ueda, K., 2013, Antimicrobial Metabolites from a marine-derived fungus, Indonesian J. Pharm., 24 (3), 163–169.

[25] Maarisit, W., Yano, K., Miyazato, T., Roy, P.K., Taira, J., and Ueda, K., 2015, Structures and bioactivities of xenicanes from an Okinawan soft coral Xenia sp., Heterocycles, 91 (3), 505–514.

[26] Watanabe, A., Kumagai, M., Mishima, T., Ito, J., Otoki, Y., Harada, T., Kato, T., Yoshida, M., Suzuki, M., Yoshida, I., Fujita, K., Watai, M., Nakagawa, K., and Miyazawa, T., 2015, Toddaculin, isolated from of Toddalia asiatica (L.) Lam., inhibited osteoclastogenesis in RAW 264 cells and enhanced osteoblastogenesis in MC3T3-E1 cells, PLoS ONE, 10 (5), e0127158.

[27] Morrison, R.T., and Boyd, R.N., 1992, Organic Chemistry, 6th Ed., Prentice Hall, New Jersey.

[28] Silverstein, R.M., Webster F.X., and Kiemle, D.J., 2005, Spectrometric Identification of Organic Compounds, 7th Ed., John Wiley & Sons, Inc., New York.



DOI: https://doi.org/10.22146/ijc.46643

Article Metrics

Abstract views : 375 | views : 421


Copyright (c) 2020 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.