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Reinereins A and B, new onocerane triterpenoids from Reinwardtiodendron cinereum

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Abstract

Bioactivity guided separation of Reinwardtiodendron cinereum barks methanol extract led to the isolation of two new onocerane triterpenoids, reinereins A and B (1 and 2), together with three known onocerane triterpenoids. Their structures were elucidated on the basis of NMR spectroscopic data. In vitro cytotoxic activities of the isolated compounds against several type of cancer cells were evaluated.

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References

  1. Mabberley DJ (2011) Meliaceae Flowering plants Eudicots: Sapindales, Cucurbitales, Myrtaceae. Kubitzki K., Springer, p 185-211

  2. Nugroho AE, Hirasawa Y, Hosoya T, Awang K, Hadi AHA, Morita H (2010) Bisleucocurine A, a novel bisindole alkaloid from Leuconotis griffithii. Tetrahedron Lett 51:2589–2592

    Article  CAS  Google Scholar 

  3. Hirasawa Y, Shoji T, Arai T, Nugroho AE, Deguchi J, Hosoya T, Uchiyama N, Goda Y, Awang K, Hadi AHA, Shiro M, Morita H (2010) Bisleuconothine A, an eburnane-aspidosperma bisindole alkaloid from Leuconotis griffithii. Bioorg Med Chem Lett 20:2021–2024

    Article  CAS  Google Scholar 

  4. Hirasawa Y, Hara M, Nugroho AE, Sugai M, Zaima K, Kawahara N, Goda Y, Awang K, Hadi AHA, Litaudon M, Morita H (2010) Bisnicalaterines B and C, Atropisomeric Bisindole Alkaloids from Hunteria zeylanica, Showing Vasorelaxant Activity. J Org Chem 75:4218–4223

    Article  CAS  Google Scholar 

  5. Nugroho AE, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Shirota O, Ekasari W, Widyawaruyanti A, Morita H (2012) Antiplasmodial indole alkaloids from Leuconotis griffithii. J Nat Med 66:350–353

    Article  CAS  Google Scholar 

  6. Nagakura Y, Nugroho AE, Hirasawa Y, Hosoya T, Rahman A, Kusumawati I, Zaini NC, Morita H (2013) Sanjecumins A and B: new limonoids from Sandoricum koetjape. J Nat Med 67:381–385

    Article  CAS  Google Scholar 

  7. Wong CP, Deguchi J, Nugroho AE, Kaneda T, Hadi AHA, Morita H (2013) Ceramicines from Chisocheton ceramicus as lipid-droplets accumulation inhibitors. Bioorg Med Chem Lett 23:1786–1788

    Article  CAS  Google Scholar 

  8. Morita H, Nugroho AE, Nagakura Y, Hirasawa Y, Yoshida H, Kaneda T, Shirota O, Ismail IS (2014) Chrotacumines G-J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity. Bioorg Med Chem Lett 24:2437–2439

    Article  CAS  Google Scholar 

  9. Wong CP, Seki A, Horiguchi K, Shoji T, Arai T, Nugroho AE, Hirasawa Y, Sato F, Kaneda T, Morita H (2015) Bisleuconothine A induces autophagosome formation by interfering with AKT-mTOR signaling pathway. J Nat Prod 78:1656–1662

    Article  CAS  Google Scholar 

  10. Nugroho AE, Hashimoto A, Wong CP, Yokoe H, Tsubuki M, Kaneda T, Hadi AHA, Morita H (2018) Ceramicines M-P from Chisocheton ceramicus: isolation and structure–activity relationship study. J Nat Med 72:64–72

    Article  CAS  Google Scholar 

  11. Nugroho AE, Sugiura R, Momota T, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Morita H (2015) Dysosesquiflorins A and B, sesquiterpenoids from Dysoxylum densiflorum. J Nat Med 69:411–415

    Article  CAS  Google Scholar 

  12. Mori R, Nugroho AE, Hirasawa Y, Wong CP, Kaneda T, Shirota O, Hadi AHA, Morita H (2014) Opaciniols A-C, new terpenoids from Garcinia opaca. J Nat Med 68:186–191

    Article  CAS  Google Scholar 

  13. Wong C, Shimada M, Nugroho AE, Hirasawa Y, Kaneda T, Hadi AHA, Osamu S, Morita H (2012) Ceramicines J-L, new limonoids from Chisocheton ceramicus. J Nat Med 66:566–570

    Article  CAS  Google Scholar 

  14. Kiang AK, Tan EL, Lim FY, Habaguchi K, Nakanishi K, Fachan L, Ourisson G (1967) Lansic acid, a bicyclic triterpene. Tetrahedron Lett 8:3571–3574

    Article  Google Scholar 

  15. Nishizawa M, Nishide H, Kosela S, Hayashi Y (1983) Structure of lansiosides: biologically active new triterpene glycosides from Lansium domesticum. J Org Chem 48:4462–4466

    Article  CAS  Google Scholar 

  16. Tanaka T, Ishibashi M, Fujimoto H, Okuyama E, Koyano T, Kowithayakorn T, Hayashi M, Komiyama K (2002) New onoceranoid triterpene constituents from Lansium domesticum. J Nat Prod 65:1709–1711

    Article  CAS  Google Scholar 

  17. Habaguchi K, Watanabe M, Nakadaira Y, Nakanishi K, Kiang AK, Lim FY (1968) The full structures of lansic acid and its minor congener, an unsymmetric onoceradienedione. Tetrahedron Lett 9:3731–3734

    Article  Google Scholar 

  18. Alexandra NM, Samuel R, Chase MW, Caroline MP, Greger H (2005) Aglaia (Meliaceae): an evaluation of taxonomic concepts based on DNA data and secondary metabolites. Am J Bot 92:534–543

    Article  Google Scholar 

  19. Dong S-H, Zhang C-R, Dong L, Wu Y, Yue J-M (2011) Onoceranoid-Type triterpenoids from Lansium domesticum. J Nat Prod 74:1042–1048

    Article  CAS  Google Scholar 

  20. Tilaar M, Wih WL, Ranti AS, Wasitaatmadja SM, Suryaningsih Junardy FD, Maily (2008) Review of Lansium domesticum correa and its use in cosmetics. Bol Latinoam Caribe Plant Med Aromat 7:183–189

    CAS  Google Scholar 

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Acknowledgements

This work was supported by Grants in-Aid for Scientific Research from JSPS, Japan.

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Correspondence to Hiroshi Morita.

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Nugroho, A.E., Inoue, D., Wong, C.P. et al. Reinereins A and B, new onocerane triterpenoids from Reinwardtiodendron cinereum. J Nat Med 72, 588–592 (2018). https://doi.org/10.1007/s11418-018-1188-8

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  • DOI: https://doi.org/10.1007/s11418-018-1188-8

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