Chemical Constituents from Fruit of Melia azedarach L. in Vietnam
Main Article Content
Abstract
Two flavonoids (apigenin and quercetin 3-O-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside]), a coumarin (scopoletin), a phenolic (vanillic acid), a triterpenoid (taraxerol) and two steroids (β-sitosterol and β-sitosterol-3-O-β-D-glucopyranoside) were isolated from the methanolic extract of the fruits of Melia azedarach L., using silica gel column chromatography methods. The structures of these compounds were elucidated using a combination of UV, IR, 1D and 2D NMR techniques (¹H-, ¹³C-NMR, COSY, HSQC and HMBC), MS analyses, and the comparison with the literature data. This is the first isolation of the compounds from Melia azedarach growing in Vietnam.
Keywords
Melia azedarach, Meliaceae, flavonoid, scopoletin, apigenin, taraxerol
Article Details
References
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[17] Jun, H.; Wei, M.; Ning, L.; and Wang, K. J. Antioxidant and Anti-inflammatory flavonoids from the flowers of ChuJu, a medical cultivar of Chrysanthemum morifolium Ramat, J. Mex. Chem. Soc., (2017), 61(4), 282-289.
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[20] Sang W. C.; Ki H. K.; Il K. L.; Sang U. C.; Shi Y. R.; and Kang R. L., Phytochemical Constituents of Bistorta manshuriniensis, Nat. Prod. Sci., (2009), 15(4), 234-240.
[21] Rasool, N.; Khan, A. Q.; and Malik, A., A taraxerane type triterpene from Euphorbia tirucalli, Phytochem., (1989), 28, 1193-1195.
[22] Kuo, H. Y.; Yeh, M. H., Chemical constituents of heartwood of Bauhinia purpurea, J. Chin. Chem. Soc., (1997), 44, 379-383.
[2] Phạm Hoàng Hộ (1999). Cây cỏ Việt Nam. Nhà xuất bản Trẻ.
[3] Nguyễn Kim Đào (2003). Danh lục các loài thực vật Việt Nam, Tập II, Nxb Nông Nghiệp, Hà Nội, 987-1007.
[4] Namba, T. The Encyclopedia of Wakan-Yaku (Traditional Sino-Japanese Medicines) with Color Pictures, Hoikusya, Osaka, (1994), I, 247.
[5] Okada, M. Newly Revised Illustrated Medicinal Plants of World, Hokuryukan Publishing Co., Ltd., Tokyo, (2002), 262.
[6] Vishnukanta; Rana, A. C. M. azedarach: A phytopharmacological review, Pharmacogn. Rev., (2008), 2, 173-179.
[7] Tan, Q. G.; Luo, X. D. Meliaceous limonoids: chemistry and biological activities, Chem. Rev., (2011), 111, 7437-7522.
[8] Carpinella, M. C.; Defago, M. T.; Valladares, G.; Palacios, S. M. Antifeedant and insecticide properties of a limonoid from M. azedarach (Meliaceae) with potential use for pest management, J. Agric. Food Chem., (2003), 51, 369-374.
[9] Liu, H. B.; Zhang, C. R.; Dong, S. H.; Dong, L.; Wu, Y.; Yue, J. M. Limonoids and triterpenoids from the seeds of M. azedarach, Chem. Pharm. Bull., (2011), 59, 1003-1007.
[10] Nakatani, M.; Huang, R. C.; Okamura, H.; Iwagawa, T.; Tadera, K.; Naoki, H. Three new antifeeding meliacarpins from Chinese M. azedarach Linn., Tetrahedron, (1995), 51, 11731-11736.
[11] Ntalli, N. G.; Cottiglia, F.; Bueno, C. A.; Alche, L. E.; Leonti, M.; Vargiu, S.; Bifulco, E.; Menkissoglou-Spirowdi, U.; Caboni, P. Cytotoxic tirucallane triterpenoids from M. azedarach fruits, Molecules, (2010), 15, 5866-5877.
[12] Ochi, M.; Kotsuki, H.; Ishida, H.; Tokoroyama, T. Limonoids from M. azedarach Linn. var. japonica Makino. II. The natural hydroxyl precursor of sendanin, Chem. Lett., (1978), 99-102.
[13] Su, Z. S.; Yang, S. P.; Zhang, S.; Dong, L.; Yue, J. M. Meliacarbins A-K: eleven limonoids from the twigs and leaves of M. azedarach, Helv. Chim. Acta., (2011), 94, 1515-1526.
[14] Wu, S. B.; Bao, Q. Y.; Wang, W. X.; Zhao, Y.; Xia, G.; Zhao, Z.; Zeng, H.; Hu, J. F. Cytotoxic triterpenoids and steroids from the bark of M. azedarach, Planta Med., (2011), 7, 922-928.
[15] Zhou, H.; Hamazaki, A.; Fontana, J. D.; Takahashi, H.; Esumi, T.; Wandscheer, C. B.; Tsujimoto, H.; Fukuyama, Y. New ring C-seco limonoids from Brazilian M. azedarach and their cytotoxic activity, J. Nat. Prod., (2004), 67, 1544-1547.
[16] Kim, M.; Kim, S. K.; Park, B. N.; Lee, K. H.; Min, G. H.; Seoh, J. Y.; Park, C. G.; Hwang, E. S.; Cha, C. Y.; Kook, Y. H. Antiviral effects of 28-deacetylnomilinon herpes simplex virus-1 replication, Antiviral Res., (1999), 43, 103-112.
[17] Jun, H.; Wei, M.; Ning, L.; and Wang, K. J. Antioxidant and Anti-inflammatory flavonoids from the flowers of ChuJu, a medical cultivar of Chrysanthemum morifolium Ramat, J. Mex. Chem. Soc., (2017), 61(4), 282-289.
[18] Lallemand, J. Y. and Duteil, M. ¹³C NMR spectra of quercetin and rutin, Magnetic Resonance in Chemistry, (1977), 9(3), 179-180.
[19] Mofiz Uddin Khan, N. M. and Sagar H. Md., Scopoletin and β-sitosterolglucoside from roots of Ipomoea digitata, J. Pharmacog. Phytochem., (2015), 4(2), 5-7.
[20] Sang W. C.; Ki H. K.; Il K. L.; Sang U. C.; Shi Y. R.; and Kang R. L., Phytochemical Constituents of Bistorta manshuriniensis, Nat. Prod. Sci., (2009), 15(4), 234-240.
[21] Rasool, N.; Khan, A. Q.; and Malik, A., A taraxerane type triterpene from Euphorbia tirucalli, Phytochem., (1989), 28, 1193-1195.
[22] Kuo, H. Y.; Yeh, M. H., Chemical constituents of heartwood of Bauhinia purpurea, J. Chin. Chem. Soc., (1997), 44, 379-383.