Isolation of Dihydrostilbenes from Macaranga Heynei and their Bioactivities

  • Authors

    • A S. Kamarozaman
    • N Ahmat1
    • A L. Muhammad Low
    • N F. Rajab
    • Z Zamkhuri
    • Z Shaameri
    • N Jaafar Sidik
    • N D. A. Kamaruzzaman
    2019-12-24
    https://doi.org/10.14419/ijet.v7i4.14.27513
  • antibacterial activity, cytotoxicity, dihydrostilbenes, Macaranga heynei

  • Abstract

    Macaranga is known to contain abundant sources of prenylated flavonoids and stilbenoids which possessed broad spectrum of biological activities including anti-inflammatory, antimicrobial, antioxidant and cytotoxicity. These species are widely distributed in New Guinea, Borneo and from West Africa to the south Pacific islands. Although Macaranga comprises a large number of species, this genus has not been widely investigated which prompted us to conduct a study on Macaranga heynei. This research is conducted to isolate and characterise the compounds from M. heynei as well as to access the antibacterial and cytotoxicity of the isolates. The purification from the leaves of M. heynei has successfully yielded three dihydrostilbenes which were analysed by means of NMR, UV-Vis, FTIR, MS and comparison with the literature data. These compounds were characterised as laevifolins A (1) and B (2) as well as macarubiginosin C (3). Laevifolin A (1) exhibited good activity against S.cohnii subsp. urealyticum and moderate activity against S.aureus ATCC 25923 with the IC50 values of 11.65 and 27.13 ï­M respectively. It also displayed pronounced inhibition against HT-29 cells with an IC50 value of 21.20 ï­M. Meanwhile, laevifolin B (2) displayed moderate activity on S.cohnii subsp. urealyticum but strong inhibition against S.aureus ATCC 25923 with the IC50 values of 20.71 and 1.64 ï­M respectively.

     

  • References

    1. [1] WWF Malaysia (2015), About WWF–Malaysia: Forests. http://www.wwf.org.my/about_wwf/what_we_do/forests_main/

      [2] Lim TY, Lim YY, Yule CM (2009), Evaluation of antioxidant, antibacterial and anti-tyrosinase activities of four Macaranga species. Food Chemistry 114, 594–599.

      [3] Phupattanapong L, Wongprasert T (1987), Thai Medicinal Plants. Part 5. Chutima, Bangkok.

      [4] Shinji F, Kanki K, Yukinori M, Tsuyoshi T, Shigeo N (1995), Cytocidal and antimicrobial activities of flavonoids. Natural Medicines 49(3), 322-328.

      [5] Orhan DD, Ozcelik B, Ozgen S, Ergun F (2010), Antibacterial, antifungal and antiviral activities of some flavonoids. Microbiological Research 165, 496–504.

      [6] Jianguo C, Xian X, Xiling D, Jianbo X, Quanxi W, Andrae-Marobela K, Okatch H (2013), Flavonoids profiles, antioxidant, acetylcholinesterase inhibition activities of extract from Dryoathyrium boryanum (Willd.) Ching. Food and Chemical Toxicology 55, 121–128.

      [7] Zakaria I, Ahmat N, Jaafar FM, Widyawaruyanti A (2012), Flavonoids with antiplasmodial and cytotoxic acitivities of Macaranga triloba. Fitoterapia 83, 968–972.

      [8] Paul S, Mizuno CS, Lee HJ, Zheng X, Chajkowisk S, Rimoldi JM, Conney A, Suh N, Rimando AM (2010), In vitro and in vivo studies on stilbene analogs as potential treatment agents for colon cancer. European Journal of Medicinal Chemistry 45, 3702–3708.

      [9] Dvorakova M, Landa P (2017), Anti-inflammatory activity of natural stilbenoids : A review. Pharmacological Research 124, 126–145.

      [10] Trombetta D, Giofre SV, Tomaino A, Raciti R, Saija A, Cristani M, Romeo R, Siracusa L, Ruberto G (2014), Selective COX-2 inhibitory properties of dihydrostilbenes from liquorice leaves–in vitro assays and structure/activity relationship study. Natural Product Communications 9(12), 1761–1764.

      [11] Biondi DM, Rocco C, Ruberto G (2003), New dihydrostilbene derivatives from the leaves of Glychyrrhiza glabra and evaluation of their antioxidant activity. J. Nat. Prod. 66, 477–480.

      [12] Jansen PCM, Westphal E, Wulijarni-Soetjipto N (1997) PROSEA : Plant Resources of South – East Asia 11, Auxiliary Plants. LIPI Press, Jakarta.

      [13] Whitmore TC (2008), The Genus Macaranga: A Prodromus. Kew Publishing, United Kingdom.

      [14] Ilmiawati A, Hakim EH, Syah YM (2015), Prenylated 9,10-dihydrophenanthrenes from Macaranga javanica. Zeitschrift für Naturforschung B 70(9), 659–663.

      [15] Magadula JJ (2014), Phytochemistry and pharmacology of the genus Macaranga: A review. Journal of Medicinal Plant Research. 8(12), 489–503.

      [16] Wiegand I, Hilpert K, Hancock REW (2008), Agar and broth dilution methods to determine the minimal inhibitory concenctration (MIC) of antimicrobial substances. Nature Protocols 3(2), 163–175.

      [17] Skehan P, Storeng R, Scudiero D, Monks A, Mcmahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990), New colorimetric cytotoxicity assay for anticancer-drug screening. JNCI: Journal of the National Cancer Institute 82(13), 1107–1112.

      [18] Ahmat N, Said IM, Latip J, Din LB, Syah YM, Hakim EH (2007), New prenylated dihydrostilbenes from Croton laevifolius. Natural Product Communications 2(11), 1137–1140.

      [19] Kamarozaman AS, Ahmat N, Rahman NFA, Yen KH (2018), Prenylated dihydrostilbenes from Macaranga heynei (Euphorbiaceae). Malaysian Journal of Analytical Sciences 22(2), 258–263.

      [20] Tanjung M, Hakim EH, Syah YM (2017), Prenylated dihydrostilbenes from Macaranga rubiginosa. Chem. Nat. Compd. 53, 215–218.

      [21] El-din MMG, El-gamal MI, Abdel-Maksoud MS, Yoo KH, Baek D, Choi J, Lee H, Oh C-H (2016), Design, synthesis and in vitro antiproliferative and kinase inhibitory effects of pyrimidinylpyrazole derivatives terminating with arylsulfonamido or cyclic sulfamide substituents. Journal of Enzyme Inhibition and Medicinal Chemistry 31(S2), 111–112.

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  • How to Cite

    S. Kamarozaman, A., Ahmat1, N., L. Muhammad Low, A., F. Rajab, N., Zamkhuri, Z., Shaameri, Z., Jaafar Sidik, N., & D. A. Kamaruzzaman, N. (2019). Isolation of Dihydrostilbenes from Macaranga Heynei and their Bioactivities. International Journal of Engineering & Technology, 7(4.14), 133-136. https://doi.org/10.14419/ijet.v7i4.14.27513

    Received date: 2019-02-18

    Accepted date: 2019-02-18

    Published date: 2019-12-24