Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Compounds from the Seeds of Myristica fragrans and Their Cytotoxic Activity

  • Cuong, To Dao (College of Pharmacy, Catholic University of Daegu) ;
  • Lim, Chae-Jin (College of Pharmacy, Catholic University of Daegu) ;
  • Trang, Tran Thi Thu (College of Pharmacy, Catholic University of Daegu) ;
  • Bae, Yoon-Ho (College of Pharmacy, Catholic University of Daegu) ;
  • Thu, Nguyen Van (College of Pharmacy, Catholic University of Daegu) ;
  • Tung, Nguyen The (College of Pharmacy, Catholic University of Daegu) ;
  • Hung, Tran Manh (Faculty of Medicine and Pharmacy, Duy Tan University) ;
  • Woo, Mi-Hee (College of Pharmacy, Catholic University of Daegu) ;
  • Choi, Jae-Sue (Department of Food Science and Nutrition, Pukyoung National University) ;
  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu)
  • Received : 2012.04.10
  • Accepted : 2012.05.16
  • Published : 2012.06.30
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Abstract

Six lignan compounds, 1-(17,21-dihydroxyphenyl)-9-(12,13-dihydroxyphenyl)-1-nonanone (malabaricone C) (1), 7'-(3',4'-methylenedioxyphenyl)-8,8'-dimethyl-7-(3,4-dihydroxyphenyl)-butane (2), 7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7-(3-methoxy-4-hydroxyphenyl)-butane (3), 7-(4-hydroxy-3-methoxyphenyl)-7'-(3',4'-methylenedioxyphenyl)-8,8'-lignan-7-methyl ether (4), (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-hydroxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (5), and (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-acetoxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (6), were isolated from the seeds of Myristica fragrans. The chemical structures of these compounds were determined on the basis of spectroscopic analyses including 2D NMR. Compounds 1 - 6 were evaluated for their cytotoxic activity against the HL-60, MCF-7, and A549 cancer cell lines in in vitro.

Keywords

References

  1. Banerjee, D., Maity, B., Bandivdeker, A.H., Bandyopadhyay, S.K., and Chattopadhyay, S., Angiogenic and cell proliferating action of the natural diarylnonanoids, malabaricone B and malabaricone C during healing of indomethacin-induced gastric ulceration. Pharm. Res. 25, 1601-1609 (2011).
  2. Chong, Y.M., Yin, W.F., Ho, C.Y., Mustafa, M.R., Hadi, A.H., Awang, K., Narrima, P., Koh, C.L., Appleton, D.R., and Chan, K.G., Malabaricone C from Myristica cinnamomea exhibits anti-quorum sensing activity. J. Nat. Prod. 74, 2261-2264 (2011). https://doi.org/10.1021/np100872k
  3. Duan, L., Tao, H.D., Hao, X.J., Gu, Q.Q., and Zhu, W.M., Cytotoxic and Antioxidative Phenolic Compounds from the Traditional Chinese Medical Plant, Myristica fragrans. Plant. Med. 75, 1241-1245 (2009). https://doi.org/10.1055/s-0029-1185506
  4. Halliwell, B. and Gutteridge, J.M.C., Free radicals in Biology and Medicine, 3rd ed. Oxford Univ. Pres. (2000).
  5. Janssen, J., Laekeman, G.M., Peiters, L.A., Totte, J., Herman, A.G., and Vlietinck, A.J., Nutmeg oil: Identification and quantitation of its most active constituents as inhibitors of platelet aggregation. J. Ethnopharmacol. 29, 179-188 (1990). https://doi.org/10.1016/0378-8741(90)90054-W
  6. Jin, D.Q., Lim, C.S., Hwang, J.K., Ha, I., and Han, J.S., Anti-oxidant and anti-inflammatory activities of macelignan in murine hippocampal cell line and primary culture of rat microglial cells. Biochem. Biophys. Res. Commun. 331, 1264-1269 (2005). https://doi.org/10.1016/j.bbrc.2005.04.036
  7. Kim Van, L.T., Hung, T.M., Thuong, P.T., Ngoc, T.M., Kim, J.C., Jang, H.S., Cai, X.F., Oh, S.R., Min, B.S., Woo, M.H., Choi, J.S., Lee, H.K., and Bae, K., Oleanane-type triterpenoids from Aceriphyllum rossii and their cytotoxic activity. J. Nat. Prod. 72, 1419-1423 (2009). https://doi.org/10.1021/np900273z
  8. Kim, S.H., Lee, D.H., Kwon, S.H., Lim, B.H., Lee, S.H., and Min, B.C., Isolation and Quantitative Determination Method Validation of myristicin from Myristica fragrans Houttuyn. Korean J. Pharmacogn. 38, 19-21 (2007).
  9. Kwon, H.S., Kim, M.J., Jeong, H.J., Yang, M.S., Park, K.H., Jeong, T.S., Lee, W.S., Low-density lipoprotein (LDL)-antioxidant lignans from Myristica fragrans seeds. Bioorg. Med. Chem. Lett. 18, 194-198 (2008). https://doi.org/10.1016/j.bmcl.2007.10.098
  10. Lai, C.C., Huang, F.M., Yang, H.W., Chan, Y., Huang, M.S., Chou, M.Y., and Chang, Y.C., Antimicrobial activity of four root canal sealers against endodontic pathogens. Clin. Oral. Invest. 5, 236-239 (2001). https://doi.org/10.1007/s00784-001-0135-2
  11. Maity, B., Yadav, S.K., Patro, B.S., Tyagi, M., Bandyopadhyay, S.K., and Chattopadhyay, S., Molecular mechanism of the anti-inflammatory activity of a natural diarylnonanoid, malabaricone C. Free Radic. Biol. Med. 2012 Feb 15. [Epub ahead of print].
  12. Mello-Filho, A.C., Meneghini, R. Iron is the intracellular metal involved in the production of DNA damage by oxygen radicals. Mutat. Res. 251, 109-113 (1991). https://doi.org/10.1016/0027-5107(91)90220-I
  13. Miyazawa, M., Asahara, H., and Ameoka, H., O-demethylation of meso-dimethyl dihydroguaiaretic acid in spodoptera litura. Phytochemistry 46, 1173-1175 (1997). https://doi.org/10.1016/S0031-9422(97)80005-2
  14. Morita, T., Jinno, K., Kawagishi, H., Arimoto, Y., Suganuma, H., Inakuma, T., and Sugiyama, K., Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/dgalactosamine- induced liver injury. J. Agric. Food. Chem. 51, 1560-1565 (2003). https://doi.org/10.1021/jf020946n
  15. Mukherjee, P.K., Kumar, V., and Houghton, P.J., Screening of Indian medicinal plants for acetylcholinesterase inhibitory activity. Phytother. Res. 21, 1142-1145 (2007). https://doi.org/10.1002/ptr.2224
  16. Navarro, E., Alonso, S.J., Navarro, R., Trujillo, J., and Jorge, E., Elenoside increases intestinal mobility. World J. Gastroenterol 28, 7143-7148 (2006).
  17. Orabi, K.Y., Mossa, J.S., and El-Feraly, F.S., Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans). J. Nat. Prod. 54, 856-859 (1991). https://doi.org/10.1021/np50075a017
  18. Patro, B.S., Bauri, A.K., Mishra, S., and Chattopadhyay, S., Antioxidant activity of Myristica malabarica extracts and their constituents. J. Agric. Food. Chem. 53, 6912-6918 (2005). https://doi.org/10.1021/jf050861x
  19. Patro, B.S., Tyagi, M., Saha, J., and Chattopadhyay, S., Comparative nuclease and anti-cancer properties of the naturally occurring malabaricones. Bioorg. Med. Chem. 18, 7043-7051 (2010). https://doi.org/10.1016/j.bmc.2010.08.011
  20. Pham, V.C., Jossang, A., Sevenet, T., and Bodo, B., Cytotoxic acylphenols from Myristica maingayi. Tetrahedron 56, 1707-1713 (2000). https://doi.org/10.1016/S0040-4020(00)00074-0
  21. Potter, G.A., Patterson, L.H., Wanogho, E., Perry, P.J., Butler, P.C., Ijaz, T, Ruparelia, K.C., Lamb, J.H., Farmer, P.B., Stanley, L.A., and Burke, M.D., The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer 86, 774-778 (2002). https://doi.org/10.1038/sj.bjc.6600197
  22. Rao, K.V. and Chattopadhyay, S.K., Regioselective cleavage of the methylenedioxy group: Conversion of (-)-austro- bailignan 5 to (-)- dihydroguaiaretic acid. J. Org. Chem. 55, 142-1429 (1990).
  23. Shinohara, C., Mori, S., Ando, T., and Tsuji, T., Arg-gingipain inhibition and anti-bacterial activity selective for Porphyromonas gingivalis by malabaricone C. Biosci. Biotechnol. Biochem. 63, 1475-1477 (1999). https://doi.org/10.1271/bbb.63.1475
  24. Skoglund, L.A. and Jorkjend, L., Postoperative pain experience after gingivectomies using different combination of local anaesthetic agents and periodontal dressings. J. Clin. Periodontol. 18, 204-209 (1991). https://doi.org/10.1111/j.1600-051X.1991.tb01135.x
  25. Yang, S., Na, M.K., Jang, J.P., Kim, K.A., Kim, B.Y., Sung, N.J., Oh W.K., and Ahn, J.S., Inhibition of protein tyrosine phosphatase 1B by lignans from Myristica fragrans. Phytother. Res. 20, 680-682 (2006). https://doi.org/10.1002/ptr.1935