Malaysian Journal of Analytical Sciences Vol 22 No 2 (2018): 258 - 263

DOI: 10.17576/mjas-2018-2202-10

 

 

 

PRENYLATED DIHYDROSTILBENES FROM Macaranga heynei (EUPHORBIACEAE)

 

(Dihidrostilbena Terprenil daripada Macaranga heynei (Euphorbiaceae))

 

Aisyah Salihah Kamarozaman1,2,3*, Norizan Ahmat2,3, Nur Fariza Abd Rahman1, Khong Heng Yen4

 

1Centre of Foundation Studies,

Universiti Teknologi MARA, Selangor Branch, Dengkil Campus, 43800 Dengkil, Selangor, Malaysia

2Faculty of Applied Sciences,

Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia

3Atta-ur-Rahman Institute for Natural Product Discovery,

Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor, Malaysia

4Faculty of Applied Sciences,

Universiti Teknologi MARA, Sarawak Branch, Samarahan Campus, 94300 Kota Samarahan, Sarawak, Malaysia

 

*Corresponding author:  aisyah2910@puncakalam.uitm.edu.my

 

 

Received: 4 December 2016; Accepted: 1 December 2017

 

 

Abstract

Macaranga is the largest genus in Euphorbiaceae which consists of approximately 300 species and are widely distributed in New Guinea, Borneo and from West Africa to the south Pacific islands. Phytochemical study on the leaves of Macaranga heynei has been conducted. The powder of the leaves of M. heynei was macerated in methanol at room temperature for 24 hours and repeated three times. The crude extract obtained was dissolved in aqueous methanol (80:20) and partitioned with hexane and ethyl acetate. The ethyl acetate crude extract was fractionated by vacuum liquid chromatography (VLC) with hexane:ethyl acetate in increasing polarity to give seven combined fractions (MH 1-7). Fraction MH 2 (1000 mg) was further purified by radial chromatography (RC) with hexane:ethyl acetate in increasing polarity to give six combined subfractions (MH 21-26). Fraction MH 23 (693.7 mg) was further purified by the same chromatographic technique but with different eluent which was chloroform:ethyl acetate in increasing polarity to afford two pure compounds (1) (10 mg) and (2) (12 mg). Based on spectroscopy analysis, the pure compounds were characterized as laevifolins A (1) and B (2).

 

Keywords:  Laevifolin A, laevifolin B, leaves, Macaranga heynei

 

Abstrak

Macaranga merupakan genus terbesar dalam famili Euphorbiaceae yang mengandungi kira-kira 300 spesies dan taburannya meliputi New Guinea, Borneo dan dari Afrika Selatan ke utara kepulauan Pasifik. Kajian fitokimia ke atas daun Macaranga heynei telah dijalankan. Serbuk daun M. heynei direndam dalam metanol pada suhu bilik selama 24 jam dan pengesktrakan diulang sebanyak tiga kali. Ekstrak mentah yang diperolehi telah dilarutkan dalam larutan metanol  (80:20) dan dipisahkan dengan heksana dan etil asetat. Etil asetat mentah difraksinasi menggunakan kromatografi cecair vakum (KCV) dengan heksana:etil asetat mengikut peningkatan kekutuban menghasilkan tujuh fraksi gabungan (MH 1-7). Fraksi MH 2 (1000 mg) selanjutnya ditulenkan dengan menggunakan kromatografi radial (RC) dengan heksana:etil asetat mengikut peningkatan kekutuban menghasilkan enam subfraksi gabungan (MH 21-26). Fraksi MH 23 (693.7 mg) seterusnya ditulenkan dengan menggunakan teknik kromatografi yang sama tetapi menggunakan eluen yang berbeza iaitu kloroform:etil asetat mengikut peningkatan kekutuban menghasilkan dua sebatian tulen (1) (10 mg) dan (2) (12 mg). Berdasarkan analisis spektroskopi, sebatian tulen tersebut dicirikan sebagai laevifolin A (1) dan B (2).

 

Kata kunci:  Laevifolin A, laevifolin B, daun, Macaranga heynei

 

References

1.       Lim, T. Y., Lim, Y. Y. and Yule, C. M. (2009). Evaluation of antioxidant, antibacterial and anti-tyrosinase activities of four Macaranga species. Food Chemistry, 114: 594-599.

2.       Whitmore, T. C. (1967). Studies in Macaranga, an easy genus of Malayan wayside trees. Malayan Nature Journal, 20(3): 89–99.

3.       Corner, E. J. H. (1988). Wayside trees of Malaya. Malayan Nature Society, 1: pp 296–304.

4.       Zakaria, R., Rosley, N. F. N., Mansor, M. and Zakaria, M. Y. (2008). The distribution of Macaranga, genus (family euphorbiaceae) in Penang Island, Peninsular Malaysia. Journal of Bioscience, 19(2): 91-99.

5.       Phupattanapong, L. and  Wongprasert, T. (1987) Thai medicinal plants. Part 5. Chutima: Bangkok.

6.       Orwa, C., Mutua, A., Kindt, R., Jamnadass, R. and Anthony, S. (2009) Agroforestree Database: A tree reference and selection guide version 4.0 from http://www.worldagroforestry.org/sites/treedbs/ treedatabases.asp. [Access online 22nd July 2016].

7.       Sutthivaiyakit, S., Unganon,t S., Sutthivaiyaki,t P. and Suksamrarn, A. (2002). Diterpenylated and prenylated flavonoids from Macaranga denticulata. Tetrahedron, 58: 3619-3622.

8.       Kumazawa, S., Murase, M., Momose, N. and Fukumoto, S. (2014). Analysis of antioxidant prenylflavonoids in different parts of Macaranga tanarius, the plant origin of Okinawan propolis. Asian Pacific Journal of Tropical Medicine, 7(1): 16-20.

9.       Lin, J. H., Ishmatsu, M., Tanaka, T., Nonaka, G. and Nishioka, I. (1990). Tannins and related compounds. XCVI. Structures of macaranins and macarinins, new hydrolyzable tannis possessing macaranoyl and tergalloy ester groups from the leaves of Macaranga sinensis (BAILL.) Muell.-Arg. Chemical and. Pharmaceutical Bulletin, 3: 1844-1851.

10.    Beutler, J. A., Shoemaker, R. H., Johnson, T. and Boyd, M. R. (1998). Cytotoxic geranyl stilbenes from Macaranga schweinfurthii. Journal  Natural Product, 61: 1509-1512.

11.    Salah, M. A., Bedir, E., Toyang, N. J., Khan, I. A., Harries, M. D. and Wedge, D. E. (2003). Antifungal clerodane diterpenes from Macaranga monandra (L) Muell. et Arg. (Euphorbiaceae). Journal of Agricultural and Food Chemistry, 51(26): 7607-7610.

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

13.    Orhan, D. D., Ozcelik, B., Ozgen, S. and Ergun, F. (2010). Antibacterial, antifungal and antiviral activities of some flavonoids. Microbiological Research, 165: 496-504.

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

15.    Das, S., Mitra, I., Batuta, S., Alam, M. N., Roy, K. and Begum, N. A. (2014). Design, synthesis and exploring the quantitative structure–activity relationship of some antioxidant flavonoid analogues. Bioorganic & Medicinal Chemistry Letters, 24(21): 5050-5054.

16.    Ilmiawati, A., Hakim, E. H. and Syah, Y. M. (2015). Prenylated 9,10-dihydrophenanthrenes from Macaranga javanica. Zeitschrift für Naturforschung B, 70(9): 659-663.

17.    Jansen, P. C. M., Westphal, E. and Wulijarni-Soetjipto, N. (1997). PROSEA: Plant resources of south-east asia 11, Auxiliary Plants. LIPI Press: Jakarta.

18.    Ahmat, N., Said, I. M., Latip, J., Din, L. B., Syah, Y. M. and Hakim, E. H. (2007). New prenylated dihydrostilbenes from Croton laevifolius. Natural Product Communications, 2(11): 1137-1140.

 




Previous                    Content                    Next