In vitro and in silico Evaluations of Chemical Constituents from the Rhizomes of Aglaonema simplex (Blume) Blume as Hyaluronidase Inhibitor

Main Article Content

Thongchai Khammee
Sawittree Rujitanapanich
Sutthiduean Chunhakant
Amornmart Jaratrungtawee
Mayuso Kuno

Abstract

From rhizomes extract of Wan Khan Mak [Aglaonema simplex (Blume) Blume] long-chain ester, butyl stearate (1) and a phytosterol, b-sitosterol (2) were isolated. The structures of two isolated compounds were elucidated by using analysis of their spectroscopic data, and compared with the reported value of the known compounds. The isolated compounds were further evaluated for in vitro hyaluronidase enzyme inhibition assay. Compound 2 (IC50 = 888.5±44.9 µg/mL) exhibited mild hyaluronidase inhibitory activity as compared with the standard 6-O-palmitoylascorbic acid (IC50 = 186.1±3.9 µg/mL). Moreover, a molecular docking study of the highest hyaluronidase inhibitor was carried out to understand the binding mode of the inhibitors into the binding site of hyaluronidase.

Downloads

Download data is not yet available.

Article Details

Section
วิทยาศาสตร์กายภาพ
Author Biographies

Thongchai Khammee

Department of Chemistry, Faculty of Science and Technology, Phranakhon Rajabhat University, Changwattana Road, Bangkhen, Bangkok 10220

Sawittree Rujitanapanich

Department of Chemistry, Faculty of Science and Technology, Phranakhon Rajabhat University, Changwattana Road, Bangkhen, Bangkok 10220

Sutthiduean Chunhakant

Department of Chemistry, Faculty of Science and Technology, Phranakhon Rajabhat University, Changwattana Road, Bangkhen, Bangkok 10220

Amornmart Jaratrungtawee

Bruker Switzerland AG, 10th Floor, Sathorn City Tower, South Sathorn Road, Thungmahamek, Sathorn, Bangkok 10120

Mayuso Kuno

Department of Chemistry, Faculty of Science, Srinakharinwirot University, Sukhumvit 23, Wattana, Bangkok 10110

References

Abdul-Aziz, M., MacLusky, N.J., Bhavnani, B.R. and Casper, R.F., 1995, Hyaluronidase activity in human semen: Correlation with fertilization in vitro, Fertil. Steril. 64: 1147-1153.
Aktan, F., 2004, iNOS-mediated nitric oxide production and its regulation, Life Sci. 75: 639-653.
Botzki, A., Rigden, D.J., Braun, S., Nukui, M., Salmen, S., Hoechstetter, J. and Buschauer, A., 2004, L-Ascorbic acid 6-hexadecanoate, a potent hyaluronidase inhibitor: X-ray structure and molecular modeling of enzyme-inhibitor complexes, J. Biol. Chem. 279: 45990-45997.
Buhren, B.A., Schrumpf, H., Hoff, N.P., Bölke, E., Hilton, S. and Gerber, P.A., 2016, Hyaluronidase: from clinical applications to molecular and cellular mechanisms, Eur. J. Med. Res. 21: 5-12.
Chao, K.L., Muthukumar, L. and Herzberg, O., 2007, Structure of human hyaluronidase-1, a hyaluronan hydrolyzing enzyme involved in tumor growth and angiogenesis, Biochemistry 46: 6911-6920.
Chen, L., Deng, H., Cui, H., Fang, J., Zuo, Z., Deng, J. and Zhao, L., 2017, Inflammatory responses and inflammation-associated diseases in organs, Oncotarget 9: 7204-7218.
Girish, K.S., Kemparaju, K., Nagaraju, S. and Vishwanath, B.S., 2009, Hyaluronidase inhibitors: A biological and therapeutic perspective, Curr. Med. Chem. 16: 2261-2288.
Kontoyianni, M., McClellan, L.M. and Sokol, G.S., 2004, Evaluation of docking performance: Comparative data on docking algorithms, J. Med. Chem. 47: 558-565.
Ndlovu, G., Fouche, G., Tselanyane, M., Cordier, W. and Steenkamp, V., 2013, In vitro determination of the anti-aging potential of four Southern African medicinal plants, BMC Complem. Altern. M. 13: 304-311.
Okoro, I.S., Tor-Anyiin, T.A., Igoli, J.O., Noundou, X.S. and Krause, R.W.M., 2017, Isolation and characterisation of stigmasterol and -sitosterol from Anthocleista djalonensis A. Chev, Asian J. Chem. Sci. 3(4): 1-5.
Perry, L.M. and Metzger, J., 1980, Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses, Cambridge MIT Press, London.
Scotti, L., Singla, R.K., Ishiki, H.M., Mendonca, F.J.B., da Silva, M.S., Barbosa Filho, J.M. and Scotti, M.T., 2016, Recent advance ment in natural hyaluronidase inhibitors, Curr. Top. Med. Chem. 16: 2525-2531.
Stern, C.D., 1984, Mini-review: Hyaluronidases in early embryonic development, Cell Biol. Int. Rep. 8: 703-717.
Santisuk, T., Peter, K.L., Sookchaloem, D., Hetterscheid, W.L.A., Gusman, G., Jacobsen, N., Idei, T. and Van, D.N., 2012, Flora of Thailand, Volume 11, Part 2: Acoraceae & Araceae, Bangkok office of the Forest Herbarium, Department of National Park, Wildlife and Plant Conservation, Bangkok.
Tshilanda, D.D., Mpiana, P.T., Onyamboko, D.N., Mbala, B.M., Ngbolua, K.T., Tshibangu, D.S. and Kasonga, T.K., 2014, Antisickling activity of butyl stearate isolated from Ocimum basilicum (Lamiaceae), Asian Pac. J. Trop. Biomed. 4: 393-398.