Further Results about Chemical Constituents of Heterostemma grandiflorum Cost.
Main Article Content
Abstract
Heterostemma grandiflorum Cost. is a flowering plant of Asclepiadaceae family, distributed in Hoa Binh, Hanoi, Ha Nam,... provinces. We have reported first results about chemical constituents and cytotoxicity of H. grandiflorum collected in Me Linh, Hanoi in the previous paper. Further study on dichloromethane and butanol extracts of H. grandiflorum’s twigs and leaves, 8 compounds have been isolated. Their structures were elucidated by the 1D and 2D NMR spectroscopy and comparison with published data. They include two flavonoids: apigenin and thalassiolin C; a phenolic: vanillic acid; two triterpenes: 3b-stearyloxy-urs-12-ene, and 3b-acetoxy-22,23,24,25,26,27-hexanordammaran-20-one; and three nitrogen-containing compounds: heteromin A, uracil, and uridine. With exceptions to apigenin and heteromin A, the rest six compounds were found for the first time from Heterostemma genus.
Keywords:
Heterostemma grandiflorum, flavonoid, triterpene, nitrogen-containing compounds.
References
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[3] W. W Fu, C. H. Tan, P. Y. Zhuang, S. M. Yang, H. F. Luo, J. J. Tan, P. Liu, D. Y. Zhu, Purinium Derivatives with Antitumor Activities from Heterostemma alatum Wight, Heterocycles, Vol. 83, No. 6, 2011, pp. 1405-1408, https://doi.org/10.3987/com-11-12204.
[4] Dictionary of Natural Product on DVD. 2018.
[5] K. T. Tam, N. T. T. Linh, L. T. H. Nhung, N. T. Tam, N. T. H. Anh, Study on Chemical Constituents and Biological Activity of Heterostemma grandiflorum Cost., J. Sci. & Tech, Hanoi University of Industry, Vol. 56, No. 6, 2020, pp. 130-132.
[6] K. S. Kumar, V. Sabu, G. Sindhu, A. A. Rauf, A. Helen, Isolation, Identification and Characterization of Apigenin from Justicia gendarussa and Its Anti-inflammatory Activity, Int. Immunopharmacol, Vol. 59, No. 6, 2018, pp.157-167, https://doi.org/10.1016/j.intimp.2018.04.004.
[7] X. Zhou, F. Wang, R. Zhou, X. Song, M. Xie, Apigenin: A Current Review on Its Beneficial Biological Activities, Journal of Food Biochemistry, 2017, pp. e12376, https://doi.org/10.1111/jfbc.12376.
[8] D. C. Rowley, M. S. T. Hansen, D. Rhodes, C. A. Sotriffer, H. Ni, J. A. McCammon, F. D. Bushman, W. Fenical, Thalassiolins A-C: New Marine-derived Inhibitors of HIV cDNA Integrase, Bioorg, Med. Chem, Vol. 10, No. 11, 2002, pp. 3619-3625, https://doi.org/10.1016/s0968-0896(02)00241-9.
[9] H. R. A. Ghareib, M. S. Abdelhamed, O. H. Ibrahim, Antioxidative Effects of the Acetone Fraction and Vanillic Acid from Chenopodium murale on Tomato Plants, Weed Biol, Manag, Vol. 10, No. 1, 2010, pp. 64-72, https://doi.org/10.1111/j.1445-6664.2010.00368.x.
[10] R. R. S. Miranda, G. D. F. Silva, L. P. Duarte, I. C. P. Fortes, S. A. V Filho, Structural Determination of 3β-Stearyloxy-urs-12-ene from Maytenus salicifolia by 1D and 2D NMR and Quantitative 13C NMR Spectroscopy, Magn. Reson. Chem, Vol. 44, No. 2, 2006, pp. 127-131, https://doi.org/10.1002/mrc.1734.
[11] J. D. P. Trees, I. S. Bellido, M. S. Gonzalez, S. Vicente, Tetracyclic Triterpenes and Nerolidol Derivatives from Santolina oblongifolia, Phytochemistry, Vol. 25, No. 1, 1986, pp. 185-190, https://doi.org/10.1016/s0031-9422(00)94526-6.
[12] J. Kitajima, K. Kimizuka, Y. Tanaka, New Drammarane-type Acetylated Triterpenoids and Their Related Compounds of Ficus pumila Fruit, Chem, Pharm. Bull, Vol. 47, No. 8, 1999, pp. 1138-1140.
[13] C. Peinador, J. O. M. Quintela, M. J. Moreira, A Short and Facile Synthesis for Heteromine A, Tetrahedron, Vol. 53, No. 24, 1997, pp. 8269-8272.
[14] Y. L. Lin, H.P. Lee, J. C. Ou, Y. H. Kuo, Three New Purinium Derivatives, Heteromines A, B, and C from Heterostemma brownii, Heterocycles, Vol. 43, No. 4, 1996, 43, 781-786, https://doi.org/10.3987/COM-95-7325.
[15] R. E. Hurd, B. R. Reid, NMR Spectroscopy of the Ring Nitrogen Protons of Uracil and Substituted Uracils; Relevance to a Base Pairing in the Solution Structure of Transfer RNA, Nucleic Acids Res, Vol. 4, No. 8, 1977, 4, pp. 2747-2755, https://doi.org/10.1093/nar/4.8.2747.
[16] F. N. Yalcin, T. Ersoz, P. Akbay, I. Calis, Phenolic, Megastigmane, Nucleotide, Acetophenon and Monoterpene Glycosides from Phlomis samia and P. carica, Turk. J. Chem, Vol. 27, No. 6, 2003, pp. 703-711.