Continuous Research on the Extraction of Stilbenes from Gnetum montanum Markgr. in Vietnam

Thi Viet Thanh Nguyen1, , Tien Thang Nguyen1
1 Hanoi University of Science and Technology, Ha Noi, Vietnam

Main Article Content

Abstract

Gnetum montanum Markgr. belongs to the Gnetaceae family. Gnetum montanum Markgr. is distributed in the northern mountainous parts of Vietnam and is used as a Vietnamese herbal medicine for the treatment of rheumatoid arthritis, muscular strain and malaria. Previous phytochemical investigations on Gnetum plants have revealed an abundance of flavonoids and stilbenoids. With the goal of isolating compounds from this species in Vietnam, in the continous phytochemical investigation of stem of Gnetum montanum Markgr., we used extraction methods with increasing polar solvents and modern chromatography methods such as thin-layer chromatography (TLC), column chromatography (CC), and high-performance liquid chromatography (HPLC). They were two dimeric stilbenes gneafricanin F (1), gnetuhainin Q (2) together with a stilbene 2,3', 5'-trihydoxy-trans-stilbene (3) and a flavonoid homoeriodictyol (4). Their structures were elucidated by ESI-MS, 1D-NMR, and 2D-NMR combined with comparison with published spectral data.

Article Details

References

[1] Nguyen Tien Ban, List of Plant Species Vietnam, Agricultural Publishing House, volume II, pp. 284, 2003.
[2] Li-Qin W., You-Xing Z., Jiang M., Ai-Qun J. & Jun Zhou, Stilbene derivatives from Gnetum montanum Markgr. f. megalocarpum Markgr, Helvetica Chimica Acta, vol. 91, pp. 159-164, Jan. 2008. https://doi.org/10.1002/hlca.200890007
[3] Lin M., Li J. B., Li S. Z., Yu D. Q., adn Liang X. T, A dimeric stilbene from Gnetum parvifolium, Phytochemistry, vol. 31, pp. 633-638, Feb. 1992. https://doi.org/10.1016/0031-9422(92)90050-Z
[4] Chun-Suo Y., Mao L., Xin L. & Ying-Hong W. Stilbene derivatives from Gnetum cleistostachyum, Journal of Asian Natural Products Research, 7 (2), pp. 131-137, 2005. https://doi.org/10.1016/S0031-9422(02)00670-2
[5] Kaisheng H., Rong-Li L., Yinghong W., and Lin M. Three New Stilbene Trimers from the Lianas of Gnetum hainanense, Planta Medica, vol. 67, iss. 1, pp. 61-64, 2001. https://doi.org/10.1055/s-2001-10875
[6] Sakagami Y., Sawabe A., Komemushi S., All Z., Tanaka T., Iliya I., and linuma M., Antibacterial activity of stilbene oligomers against vancomycin- resistant Enterococci (VRE) and methicillin-resistant Staphylococcus aureus (MRSA) and their synergism with antibiotics, Biocontrol Sciense., vol. 12, iss. 1, pp. 7-14, 2007. https://doi.org/10.4265/bio.12.7
[7] Ibrahim I., Toshiyuki T., Zulfiqar A., Munekazu I., Miyuki F., Ken-ichi N., Yoshiaki S., Jin M., Dedy D., Nobuyasu M., and Makoto U, Six Flavonostilbenes from Gnetum afircanum and Gnetum gnemon, Heterocycles, vol. 60, pp. 159-166, 2003. https://doi.org/10.3987/com-02-9632
[8] Ka-Wing C., Mingfu W., Feng C., and Chi-Tang H, Oligostilbenes from Gnetum species and anticarcinogenic and antiinflammatory activities of oligostilbenes, ACS Symposium Series, vol. 987, pp. 36-58, Sep. 2008. https://doi.org/10.1021/bk-2008-0987.ch004
[9] Le Huu Tho, Pham Cong Trinh, Nguyen Xuan Hai, DoVan Nhat Truong, and Nguyen Thi Thanh Mai, Alkaloid compounds from Bep leaves, Gnetum gnemon L., Vietnam Journal of Chemistry, vol. 57 (4e3, 4), pp. 95-99, Aug. 2019.
[10] Nguyen Ba Anh, Trieu Huy Diet, Hoang Viet Dung, and Nguyen Xuan Nhiem, Isolation and structural determination of two stilbenoid compounds from Gnetum latifolium Blume, family Gnetaceae, Journal of Pharmacy, vol. 459(54), pp. 44-48, 2014.
[11] Le Thi Hong Nhung, Nguyen The Huu, Nguyen Thi Hoang Anh, and Ngo Anh Bang, Isolation and structural determination of some stilbenoid compounds from Gnetum latifolium, Journal of Science and Technology, Hanoi University of Industry, vol. 58 (2), pp. 118-121, 2022,
[12] Do Tat Loi Vietnamese medicinal plants and herbs. Medical Publishing House. p. 662, 2004.
[13] Vu Thi Lan Phuong, Research on chemical compositions of Gnetum montanum Markgr., Hai Phong University Science Journal. vol. 34, по. 5, pp. 45-50, 2019.
[14] Nguyen Thi Viet Thanh, Dang Thanh Tung, Some Chemical Components from Gnetum montanum Markgr. in Vietnam, Journal of Science and Technology: Engineering and Technology for Sustainable Development, vol. 34, iss. 3, pp. 23-30, 2024. https://doi.org/10.51316/jst.175.etsd.2024.34.3.4
[15] Ibrahim Iliyaa, Toshiyuki Tanaka, Munekazu linuma, Zulfiqar Ali, Miyuki Furasawa, Ken-ichi Nakaya, Nobuyasu Matsuurac and Makoto Ubukata, Four dimeric stibenes in stem lianas of Gnetum africanum, Heterocycles, vol. 57, no. 8, pp. 1507-1512, 2002. https://doi.org/10.3987/com-02-9527
[16] Ying-Hong Wang., Kai-Sheng Huang & Mao Lin, Four new Stilbene Dimers from the Lianas of Gnetum Hainanense, Journal of Asian Natural Products Research, vol. 3, iss. 3, pp. 169-176, 2001. https://doi.org/10.1080/10286020108041387
[17] Zhang, Yan, Shen, Mingyun, Cui, Sunliang, Hou, TingJun, Synthesis and antiproliferative evaluation of 2-hydroxylated (E)-stilbenes, Bioorganic & Medicinal Chemistry Letters, vol. 24, iss. 23, pp. 5470-5472, 2014. https://doi.org/10.1016/J.bmcl.2014.10.009
[18] Wagner, H., V.M. Chari, and J. Sonnenbichler, 13C-NMR-spektren natürlich vorkommender flavonoide, Tetrahedron Letters, vol. 17, iss. 21, pp. 1799-1802, May 1976. https://doi.org/10.1016/S0040-4039(00)93787-0