Isolation of Four Flavanones from the Leaves of Macaranga Hypoleuca (Rchb.f. & Zoll.) Müll.Arg

  • Authors

    • H. Muhamad Nazeri
    • N. Ahmat
    • K. Abdul Khalil
    2019-12-24
    https://doi.org/10.14419/ijet.v7i4.14.27564
  • Euphorbiaceae, flavonoid, flavanone, Macaranga hypoleuca, phenolic compound

  • Abstract

    Macaranga is a large genus belongs to Euphorbiaceae family which commonly distributed in the tropical region of Africa, South-East Asia, China, and India. The plant of this genus contain flavonoids and stilbenes bearing various terpenyl groups including prenyl, geranyl and farnesyl groups. The leaves of M. hypoleuca were collected from reserved forest UiTM Jengka Pahang, Malaysia, and the dried powdered leaves were macerated in methanol at room temperature. The crude methanol extract was subjected to liquid-liquid partition using n-hexane and ethyl acetate to obtain hexane, ethyl acetate and aqueous fractions. The ethyl acetate fraction was semi purified using vacuum liquid chromatography (VLC) to give nine major fractions (MHL1-MHL9). Fraction MHL3 was further purified by column chromatography (CC) and preparative thin layer chromatography (p-TLC) to give two pure compounds, 8-prenylnaringenin (1) and sakuranetin (5,4’-dihydroxy-7-methoxyflavanone) (3). Meanwhile, fraction MHL6 was purified using column chromatography (CC) and p-TLC to yield another two pure compounds, 6-(3-hydroxy-3-methyl)naringenin (2) and 7-O-methyleriodictyol (4). The chemical structure of these isolated compounds were determined based on their 1D and 2D NMR, UV, and IR data. From this study, four flavanones were isolated from the leaves of M. hypoleuca.

     

     

  • References

    1. [1] A. Essiett and K. Ajibesin, “Antimicrobial Activities of Some Euphorbiaceae Plants Used in the Traditional Medicine of Akwa Ibom State of Nigeria,†Ethnobot. Leafl., vol. 14, no. June 1, 2010, pp. 654–64, 2010.

      [2] J. M. Joseph, “Phytochemistry and pharmacology of the genus Macaranga: A review,†J. Med. Plants Res., vol. 8, no. 12, pp. 489–503, Mar. 2014.

      [3] R. Zakaria et al., “The distribution of,†vol. 19, no. 2, pp. 91–99, 2008.

      [4] N. S. Aminah, A. N. Kristanti, and M. Tanjung, “Antioxidant activity of flavonoid compounds from the leaves of Macaranga gigantea,†vol. 6, no. July 2012, pp. 688–692, 2014.

      [5] S. Phommart, P. Sutthivaiyakit, N. Chimnoi, S. Ruchirawat, and S. Sutthivaiyakit, “Constituents of the leaves of Macaranga tanarius,†J. Nat. Prod., vol. 68, no. 6, pp. 927–930, 2005.

      [6] T. Y. Lim, Y. Y. Lim, and C. M. Yule, “Evaluation of antioxidant, antibacterial and anti-tyrosinase activities of four Macaranga species,†Food Chem., 2009.

      [7] S. Kumazawa, M. Murase, N. Momose, and S. Fukumoto, “Analysis of antioxidant prenylflavonoids in different parts of Macaranga tanarius , the plant origin of Okinawan propolis,†pp. 16–20, 2014.

      [8] I. Zakaria, N. Ahmat, F. M. Jaafar, and A. Widyawaruyanti, “Flavonoids with antiplasmodial and cytotoxic activities of Macaranga triloba,†Fitoterapia, vol. 83, no. 5, pp. 968–972, 2012.

      [9] K. Matsunami et al., “Absolute configuration of (+)-pinoresinol 4-O-[6’’-O-galloyl]-beta-D-glucopyranoside, macarangiosides E, and F isolated from the leaves of Macaranga tanarius.,†Phytochemistry, vol. 70, no. 10, pp. 1277–85, Jul. 2009.

      [10] R. M. Ngoumfo et al., “Inhibitory Effect of Macabarterin , a Polyoxygenated Ellagitannin from Macaranga barteri , on Human Neutrophil Respiratory Burst Activity,†pp. 1906–1910, 2008.

      [11] C. Ito et al., “A new flavonoid and other new components from Citrus plants,†Chem. Pharm. Bull., vol. 36, no. 9, pp. 3292–3295, 1988.

      [12] S. Tahara, M. Tanaka, and W. Barz, “Fungal metabolism of prenylated flavonoids,†Phytochemistry, vol. 44, no. 6, pp. 1031–1036, 1997.

      [13] N. B. Perry, “Antiviral and Antifungal Flavonoids, plus a Triterpene, from Hebe cupressoides,†Planta Med., vol. 60, pp. 491–492, 1994.

      [14] L. Abu-Niaaj, M. Abu-Zarga, S. Sabri, and S. Abdalla, “Isolation and biological effects of 7-O-methyleriodictyol, a flavanone isolated from Artemisia monosperma, on rat isolated smooth muscles,†Planta Med., vol. 59, no. 1, pp. 42–45, 1993.

      [15] D.-S. Yang et al., “Cytotoxic prenylated bibenzyls and flavonoids from Macaranga kurzii,†Fitoterapia, vol. 99, pp. 261–266, Dec. 2014.

      [16] L. K. Omosa et al., “Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia,†South African J. Bot., vol. 91, pp. 58–62, 2014.

      [17] B. Modak, A. Rivas, and E. Vallejos, “Antiviral activity in vitro and in vivo of natural flavonoids isolated from Heliotropium sinuatum against infectious salmon anemia virus (ISAV),†Bol. Latinoam. y del Caribe Plantas Med. y Aromáticas., vol. 11, no. 4, pp. 377–384, 2012.

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  • How to Cite

    Muhamad Nazeri, H., Ahmat, N., & Abdul Khalil, K. (2019). Isolation of Four Flavanones from the Leaves of Macaranga Hypoleuca (Rchb.f. & Zoll.) Müll.Arg. International Journal of Engineering & Technology, 7(4.14), 206-209. https://doi.org/10.14419/ijet.v7i4.14.27564

    Received date: 2019-02-19

    Accepted date: 2019-02-19

    Published date: 2019-12-24