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http://dx.doi.org/10.20307/nps.2022.28.3.115

Cytotoxic Neoflavonoids and Chalcones from the Heartwood of Dalbergia melanoxylon  

Chung, Ha Sook (College of Science and Technology, Duksung Women's University)
Publication Information
Natural Product Sciences / v.28, no.3, 2022 , pp. 115-120 More about this Journal
Abstract
Ten compounds, consisting of neoflavonoids (1-5), isoflavonoids (6 and 7), flavanone (8), and chalcones (9 and 10) were isolated from the ethyl acetate and n-butanol-soluble fractions of the heartwood of Dalbergia melanoxylon. The chemical structures were identified on the basis of spectroscopic evidence and compared to previously reported spectra. Compounds 1-10 were evaluated for cytotoxicity against HCT116 human colorectal cancer, MDA-MB-231 human metastatic breast cancer, and A2058 human melanoma cell lines. Among them, compounds 3 and 10 showed the strongest cytotoxic activity with IC50 values of 11.92±1.07 μM, 10.83±1.02 μM, and 14.37±1.02 μM, 13.62±1.09 μM against HCT116 and MDA-MB-231 cell lines, respectively. Compounds 9 and 10 also had cytotoxic activity with IC50 values of 13.49±1.18 μM and 9.82±0.91 μM against A2058 cell lines, respectively. To the best our knowledge, compounds 2 and 5-10 were isolated from this source for the first time.
Keywords
Dalbergia melanoxylon; heartwood; HCT116; MDA-MB-231; A2058; neoflavonoid; chalcone;
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1 Barragan-Huerta, B. E.; Peralta-Cruz, J.; Gonzalez-Laredo, R. F.; Karchesy, J. Phytochem. 2004, 65, 925-928.   DOI
2 Jenkins, M.; Oldfield, S.; Aylett, T. International Trade in African Blackwood; Fauna and Flora International: UK, 2002, p 7.
3 Gundidza, M.; Gaza, N. J. Ethnopharmacol. 1993, 40, 127-130.   DOI
4 Matata, D. Z.; Ngassapa, O. D.; Machumi, F.; Mainen, J. M. Evid. Based Complement. Alternat. Med. 2018, 2018, 3034612-3034627.
5 Mutai, P.; Heydenreich, M.; Thoithi, G.; Mugumbate, G.; Chibale, K.; Yenesew, A. Phytochem. Lett. 2013, 6, 671-675.
6 Ducki, S.; Forrest, R.; Hadfield, J. A.; Kendall, A.; Lawrence, N. J.; McGown, A. T.; Rennison, D. Bioorg. Med. Chem. Lett. 1998, 8, 1051-1056.   DOI
7 Erdei, E.; Torres, S. M. Expert Rev. Anticancer Ther. 2010, 10, 1811-1823.   DOI
8 Peng, F.; Du, Q.; Peng, C.; Wang, N.; Tang, H.; Xie, X.; Shen, J.; Chen, J. Phytother. Res. 2015, 29, 969-977.   DOI
9 Park, J. D.; Lee, Y. H.; Back, N. I.; Kim, S. I.; Ahn, B. Z. Kor. J. Pharmacogn. 1995, 26, 323-326.
10 Xiang, S.; Chen, H.; Luo, X.; An, B.; Wu, W.; Cao, S.; Ruan, S.; Wang, Z.; Weng, L.; Zhu, H.; Liu, Q. J. Exp. Clin. Cancer Res. 2018, 37, 184-199.
11 Haass, N. K.; Schumacher, U. Exp. Dermatol. 2014, 23, 471-472.   DOI
12 Guon, T. E.; Chung, H. S. Nat. Prod. Sci. 2016, 22, 209-215.   DOI
13 Guon, T. E.; Chung, H. S. Oncol. Lett. 2017, 14, 1703-1710.
14 Guon, T. E.; Chung, H. S. Nat. Prod. Sci. 2017, 23, 227-234.   DOI
15 Yin, X.; Huang, A.; Zhang, S.; Liu, R.; Ma, F. Molecules 2018, 23, 2163-2173.   DOI
16 Sacande, M.; Vautier, H.; Sanon, M.; Schmit, L. SEED LEAFLET, No. 135; Dalbergia melanoxylon Guill. & Perr: UK, 2007.
17 Wa ng, M.; Ma , G.; Sha o, F.; Liu, R.; Chen, L.; Liu, Y.; Ya ng, L.; Meng, X. Nat. Prod. Res. 2022, 36, 735-741.   DOI
18 Li, Q.; Wu, J.; Wang, Y.; Lian, X.; Wu, F.; Zhou, L.; Huang, Z.; Zhu, S. Holzforschung 2017, 71, 939-949.   DOI
19 Liu, Y.; Shu, J. C.; Wang, M. F.; Xu, Z. J.; Yang, L.; Meng, X. W.; Duan, W. B.; Zhang, N.; Shao, F.; Liu, R. H.; Chen, L. Y. Phytochem. 2021, 189, 112845.
20 Vihervaara, A.; Liippo, J. Contact Dermatitis 2019, 81, 294-296.
21 Donnelly, D. M. X.; O'Reilly, J.; Whalley, W. B. Phytochem. 1975, 14, 2287-2290.   DOI
22 Gautam, J.; Kumar, P.; Kushwaha, P.; Khedgikar, V.; Choudhary, D.; Singh, D.; Maurya, R.; Trivedi, R. Menopause 2015, 22, 1246-1255.   DOI
23 Donnelly, B. J.; Donnelly, D. M. X.; O'Sullivan, A. M.; Prendergast, J. P. Tetrahedron 1969, 25, 4409-4414.   DOI
24 Van Heerden, F. R.; Vincent Brandt, E.; Roux, D. G. Phytochem. 1980, 19, 2125-2129.   DOI
25 Mutai, P.; Heydenreich, M.; Thoithi, G.; Mugumbate, G.; Chibale, K.; Yenesew, A. Phytochem. Lett. 2013, 6, 671-675.
26 Wang, H.; Dong, W. H.; Zuo, W. J.; Liu, S.; Zhong, H. M.; Mei, W. L.; Dai, H. F. Fitoterapia 2014, 95, 16-21.   DOI
27 Lin, S.; Liu, R. H.; Ma, G. Q.; Mei, D. Y.; Shao, F.; Chen, L. Y. Nat. Prod. Res. 2020, 34, 2794-2801.   DOI
28 Wu, S. F.; Chang, F. R.; Wang, S. Y.; Hwang, T. L.; Lee, C. L.; Chen, S. L.; Wu, C. C.; Wu, Y. C. J. Nat. Prod. 2011, 74, 989-996.
29 Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Mitchell, J. B. Cancer Res. 1987, 47, 936-942.
30 Chan, S. C.; Chang, Y. S.; Kuo, S. C. Phytochem. 1997, 46, 947-949.
31 Umehara, K.; Nemoto, K.; Matsushita, A.; Terada, E.; Monthakantirat, O.; De-Eknamkul, W.; Miyase, T.; Warashina, T.; Degawa, M.; Noguchi, H. J. Nat. Prod. 2009, 72, 2163-2168.
32 Zeng, L.; Yuan, S.; Shen, J.; Wu, M.; Pan, L.; Kong, X. Mol. Med. Rep, 2018, 17, 3935-3943.
33 Xiong, L.; Guo, W.; Yang, Y.; Gao, D.; Wang, J.; Qu, Y.; Zhang, Y. Mol. Cell. Biochem. 2021, 476, 2729-2738.
34 Choi, C. W.; Choi, Y. H.; Cha, M. R.; Kim, Y. S.; Yon, G. H.; Kim, Y. K.; Choi, S. U.; Kim, Y. H.; Ryu, S. Y. J. Korean Soc. Appl. Biol. Chem. 2009, 52, 375-379.
35 Donnelly, D. M. X.; Sheriden, M. H. In The Flavonoid: Neoflavonoids; Harborne, J. B. Ed; Chapman & Hall, UK, 1988, pp 211-232.
36 Yahara, S.; Ogata, T.; Saijo, R.; Konishi, R.; Yamahara, J.; Miyahara, K.; Nohara, T. Chem. Pharm. Bull. 1989, 37, 979-987.   DOI
37 An, R. B.; Jeong, G. S.; Kim, Y.C. Chem. Pharm. Bull. 2008, 56, 1722-1724.
38 Guo, L. B.; Wang, L. Chin. Tradit. Herb. Drugs 2008, 39, 1147-1149.
39 Wa ttenberg, L. W.; Coccia , J. B.; Ga lbra ith, A. R. Cancer Lett. 1994, 83, 165-169.   DOI
40 Monthakantirat, O.; De-Eknamkul, W.; Umehara, K.; Yoshinaga, Y.; Miyase, T.; Warashina, T.; Noguchi, H. J. Nat. Prod. 2005, 68, 361-364.   DOI
41 Guon, T. E.; Yoon, K. M.; Chung, H. S. J. Kor. Tea Soc. 2015, 21, 59-64.