Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Cytotoxic Constituents from the Stem Bark of Chisocheton pentandrus

  • Retnowati, Rurini (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Brawijaya) ;
  • Sulistyarti, Hermin (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Brawijaya) ;
  • Wahidah, Nikmatus Zahro (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Brawijaya) ;
  • Syarifah, Anisa Lailatusy (Academy of Pharmacy of Putra Indonesia) ;
  • Salam, Suprianto (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran) ;
  • Nurlelasari, Nurlelasari (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran) ;
  • Safari, Agus (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran) ;
  • Harneti, Desi (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran) ;
  • Tanjung, Mulyadi (Department of Chemistry, Faculty of Science and Technology, Universitas Airlangga) ;
  • Hidayat, Ace Tatang (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran) ;
  • Maharani, Rani (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran) ;
  • Supratman, Unang (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran) ;
  • Shiono, Yoshihito (Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University)
  • Received : 2020.11.17
  • Accepted : 2021.02.09
  • Published : 2021.03.31
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Abstract

Eight cytotoxic constituents, consisting of six triterpenoids, cabralealactone (1), cabraleadiol (2), prototiamin A (3), 23-desmethyllimocin B (5), melianodiol (7) and indicalilacol (8) along with one limonoid, neemfruitins A (4) and one protolimonoid, protoxylocarpin G (6), were isolated from the extract of n-hexane of the stembark of Chisocheton pentandrus. The chemical structures were identified on the basis of spectroscopic evidence and compared to previously reported spectra. These isolated compounds appear for the first time in the plant. Compounds 1 - 8 were evaluated for their cytotoxic effect against MCF-7 breast cancer lines in vitro. Among the isolated compounds, melianodiol (7) showed the strongest cytotoxic activity with IC50 values of 16.8 µM.

Keywords

References

  1. Katja, D. G.; Farabi, K.; Nurlelasari.; Harneti, D.; Mayanti, T.; Supratman, U.; Awang, K.; Hayashi, H. J. Asian Nat. Prod. Res. 2017, 19, 194-200. https://doi.org/10.1080/10286020.2016.1196671
  2. Shilpi, J. A.; Saha, S.; Chong, S. L.; Nahar, L.; Sarker, S. D.; Awang, K. Chem. Biodivers. 2016, 13, 483-503. https://doi.org/10.1002/cbdv.201400373
  3. Awang, K.; Lim, C. S.; Mohamad, K.; Hiroshi, M.; Hirasawa, Y.; Takeya, K.; Thoison, O.; Hadi, A. H. A. Bioorg. Med. Chem. 2007, 15, 5997-6002. https://doi.org/10.1016/j.bmc.2007.05.049
  4. Tan, Q. G.; Luo, X. D. Chem. Rev. 2011, 111, 7437-7522. https://doi.org/10.1021/cr9004023
  5. Yang, M. H.; Wang, J. S.; Luo, J. G.; Wang, X. B.; Kong, L. Y. J. Nat. Prod. 2009, 72, 2014-2018. https://doi.org/10.1021/np900485t
  6. Mohamad, K.; Hirasawa, Y.; Litaudon, M.; Awang, K.; Hadi, A. H. A.; Takeya, K.; Ekasari, W.; Widyawaruyanti, A.; Zaini, N. C.; Morita, H. Bioorg. Med. Chem. 2009, 17, 727-730. https://doi.org/10.1016/j.bmc.2008.11.048
  7. Supratman, U.; Naibaho, W.; Salam, S.; Maharani, R.; Hidayat, A. T.; Harneti, D.; Nurlelasari.; Shiono, Y. Phytochem. Lett. 2019, 30, 81-87. https://doi.org/10.1016/j.phytol.2019.01.034
  8. Chong, S. L.; Hematpoor, A.; Hazni, H.; Sofian-Azirun, M.; Litaudon, M.; Supratman, U.; Murata, M.; Awang, K. Phytochem. Lett. 2019, 30, 69-73. https://doi.org/10.1016/j.phytol.2018.12.013
  9. Najmuldeen, I. A.; Hadi, A. H. A.; Mohamad, K.; Awang, K.; Ketuly, K. A.; Mukhtar, M. R.; Taha, H.; Nordin, N.; Litaudon, M.; Gueritte, F.; Nugroho, A. E.; Morita, H. Heterocycles 2012, 84, 1265-1270. https://doi.org/10.3987/COM-11-S(P)31
  10. Fang, X.; Di, Y. T.; Hao, X. J. Current Organic Chemistry 2011, 15, 1363-1391. https://doi.org/10.2174/138527211795378254
  11. Haldar, S.; Kolet, S. P.; Thulasiram, H. V. Green Chemistry 2013, 15, 1311-1317. https://doi.org/10.1039/c3gc40193f
  12. Nagoor, N. H.; Muttiah, N. S. J.; Lim, C. S.; In, L. L. A.; Mohamad, K.; Awang, K. PLoS One. 2011, 6, e23661. https://doi.org/10.1371/journal.pone.0023661
  13. Wong, C. P.; Shimada, M.; Nagakura, Y.; Nugroho, A. E.; Hirasawa, Y.; Kaneda, T.; Awang, K.; Hadi, A. H. A.; Mohamad, K.; Shiro, M.; Morita, H. Chem. Pharm. Bull. 2011, 59, 407-411. https://doi.org/10.1248/cpb.59.407
  14. Yang, M. H.; Wang, J. S.; Luo, J. G.; Wang, X. B.; Kong, L. Y. Bioorg. Med. Chem. 2011, 19, 1409-1417. https://doi.org/10.1016/j.bmc.2011.01.007
  15. Bordoloi, M.; Saikia, B.; Mathur, R. K.; Goswami, B. N. Phytochemistry 1993, 34, 583-584. https://doi.org/10.1016/0031-9422(93)80054-V
  16. Nurlelasari.; Katja, D. G.; Harneti, D.; Wardayo, M. M.; Supratman, U.; Awang, K. Chem. Nat. Compd. 2017, 53, 83-87. https://doi.org/10.1007/s10600-017-1916-4
  17. Supriatno.; Nurlelasari.; Herlina, T.; Harneti, D.; Maharani, R.; Hidayat, A. T.; Mayanti, T.; Supratman, U.; Azmi, M. N.; Shiono, Y. Nat. Prod. Res. 2018, 25, 1-7. https://doi.org/10.1080/14786410903244954
  18. Supratman, U.; Salam, S.; Naibaho, W.; Fajar, M.; Nurlelasari.; Katja, D. G.; Harneti, D.; Maharani, R.; Hidayat, A. T.; Lesmana, R.; Nafiah, M. A.; Shiono, Y. Phytochem. Lett. 2020, 35, 63-67. https://doi.org/10.1016/j.phytol.2019.11.002
  19. Nagaya, H.; Tobita, Y.; Nagae, T.; Itokawa, H.; Takeya, K.; Halim, A. F.; Abdel-Halim, O. B. Phytochemistry 1997, 44, 1115-1119. https://doi.org/10.1016/S0031-9422(96)00681-4
  20. Phongmaykin, J.; Kumamoto, T.; Ishikawa, T.; Suttisri, R.; Saifah, E. Arch. Pharm. Res. 2008, 31, 21-27. https://doi.org/10.1007/s12272-008-1115-8
  21. Happi, G. M.; Kouam, S. F.; Talontsi, F. M.; Lamshoft, M.; Zuhlke, S.; Bauer, J. O.; Strohmann, C.; Spiteller, M. J. Nat. Prod. 2015, 78, 604-614. https://doi.org/10.1021/np5004164
  22. Chianese, G.; Yerbanga, S. R.; Lucantoni, L.; Habluetzel, A.; Basilico, N.; Taramelli, D.; Fattorusso, E.; Taglialatela-Scafati, O. J. Nat. Prod. 2010, 73, 1448-1452. https://doi.org/10.1021/np100325q
  23. Kumar, C. S. S. R.; Srinivas, M.; Yakkundi, S. Phytochemistry 1996, 43, 451-455. https://doi.org/10.1016/0031-9422(96)00226-9
  24. Pudhom, K.; Sommit, D.; Nuclear, P.; Ngamrojanavanich, N.; Petsom, A. J. Nat. Prod. 2009, 72, 2188-2192. https://doi.org/10.1021/np900640u
  25. Puripattanavong, J.; Weber, S.; Brecht, V.; Frahm, A. W. Planta Med. 2000, 66, 740-745. https://doi.org/10.1055/s-2000-9901
  26. Kurimoto, S.; Takaishi, Y.; Ahmed, F. A.; Kashiwada, Y. Fitoterapia 2014, 92, 200-205. https://doi.org/10.1016/j.fitote.2013.11.004
  27. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107-1112. https://doi.org/10.1093/jnci/82.13.1107
  28. Hadisaputri, Y. E.; Miyazaki, T.; Suzuki, S.; Yokobori, T.; Kobayashi, T.; Tanaka, N.; Inose, T.; Sohda, M.; Kuwano, H. Ann. Surg. Oncol. 2012, 19, S589-S596. https://doi.org/10.1245/s10434-011-2097-1
  29. Chavoshi, H.; Vahedian, V.; Saghaei, S.; Pirouzpanah, M. B.; Raeisi, M.; Samadi, N. Asian Pac. J. Cancer Prev. 2017, 18, 2243-2247.