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Two new quassinoids and other constituents from Picrasma javanica wood, and their biological activities

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Abstract

Picrasma javanica Blume (Simaroubaceae) is a medium-sized tree that is distributed widely in tropical Asia. In our previous study, we isolated quassinoids from P. javanica bark collected in Myanmar, and reported their antiproliferative activities. In our ongoing research for the discovery of bioactive compounds from Myanmar medicinal plants, two new quassinoids, (16R)-methoxyjavanicin B (1) and (16S)-methoxyjavanicin B (2), along with seven known compounds (3–9), were isolated during the phytochemical investigation of the CHCl3 soluble portion of the MeOH extract of P. javanica wood. The structures of the new compounds were elucidated by analyses of their spectroscopic data (1D- and 2D-NMR, HRESIMS, and CD). A cytotoxicity assay revealed that compound 8 showed moderate activities against all tested cancer cell lines, the human lung (A549), breast (MCF7), and cervical (HeLa), and the normal fibroblast cell line, with IC50 values ranging from 48.6 to 65.9 μM. Furthermore, the antibacterial assay demonstrated that 1 and 2 had the highest activities (MIC value of 1.6 μM each), followed by 5 and 3 (MIC values of 3.1 and 6.3 μM, respectively) against the Gram-positive bacterium B. subtilis.

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Acknowledgements

This work was supported in part by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan (JSPS KAKENHI Grants JP 17K08333, JP15H05138, JP17H02203, JP26303005, and JP17H05435), and Grants from the Kobayashi International Scholarship Foundation (Hiroyuki Morita), the Kanae Foundation for the Promotion of Medical Science (Hiroyuki Morita), and the Takahashi Industrial and Economic Research Foundation (Hiroyuki Morita).

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Authors and Affiliations

  1. Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama, 930-0194, Japan

    Prema, Chin Piow Wong, Maurice Ducret Awouafack, Nwet Nwet Win & Hiroyuki Morita

  2. Department of Chemistry, University of Yangon, Yangon, 11041, Myanmar

    Prema, Yi Yi Win & Hla Ngwe

  3. Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41 Shinagawa-ku, Tokyo, 142-8501, Japan

    Alfarius Eko Nugroho & Hiroshi Morita

  4. Natural Products Chemistry Research Unit, Department of Chemistry, Faculty of Science, University of Dschang, P. O. Box 67, Dschang, Cameroon

    Maurice Ducret Awouafack

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  1. Prema
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  2. Chin Piow Wong
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  3. Alfarius Eko Nugroho
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  4. Maurice Ducret Awouafack
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  6. Nwet Nwet Win
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  7. Hla Ngwe
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Correspondence to Hiroshi Morita or Hiroyuki Morita.

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Prema, Wong, C.P., Nugroho, A.E. et al. Two new quassinoids and other constituents from Picrasma javanica wood, and their biological activities. J Nat Med 73, 589–596 (2019). https://doi.org/10.1007/s11418-018-01279-z

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  • DOI: https://doi.org/10.1007/s11418-018-01279-z

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