Browse > Article

Anti-Proliferative Effects of β-Cyclodextrin Inclusion Complexes with Coumarinolignans from Acer mono  

Yim, Soon-Ho (Department of Pharmaceutical Engineering, Dongshin University)
Jung, Da-Woon (School of Life Sciences, Gwangju Institute of Science and Technology)
Williams, Darren R. (School of Life Sciences, Gwangju Institute of Science and Technology)
Geckeler, Kurt E. (Department of Nanobio Materials and Electronics, Gwangju Institute of Science and Technology)
Kim, Kyung Keun (Chonnam National University Medical School)
Shin, Boo Ahn (Chonnam National University Medical School)
Lee, Ik-Soo (College of Pharmacy and Research Institute of Drug Development, Chonnam National University)
Kim, Huyn Jung (College of Pharmacy and Natural Medicine Research Institute, Mokpo National University)
Publication Information
Korean Journal of Pharmacognosy / v.46, no.2, 2015 , pp. 133-139 More about this Journal
Abstract
Two coumarinolignans, cleomiscosins C (1) and D (2) were isolated from the heartwood of Acer mono, together with four compounds, 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (3), 5-O-methyl-(E)-resveratrol-3-O-${\beta}$-D-apiofuranosyl-(1$\rightarrow$6)-${\beta}$-D-glucopyranoside (4), scopoletin (5), and (E)-resveratrol-3-O-${\beta}$-D-glucopyranoside (6). Of them, cleomiscosins C (1) and D (2) were applied to preparing inclusion complex molecules with ${\beta}$-cyclodextrin (${\beta}$-CD) to improve the very poor solubility in cell media. The CD complexes of 1 and 2 exhibited an enhancement of water solubility which is feasible to measure their cytotoxicity using a spectrophotometer in a cell-based assay. Anti-proliferative activity of these complex molecules was successfully estimated on HCT116 human colon cancer cells, and cleomiscosin D (2) showed anti-proliferative effects at the concentration of 1.95~31.2 ${{\mu}g}$/mL in a dose-dependent manner.
Keywords
Acer mono; Coumarionolignans; Cleomiscosins; ${\beta}$-Cyclodextrin inclusion complex; Anti-proliferation;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Ray, A. B., Chattopadhyay, S. K. and Kumar, S. (1985) Structures of cleomiscosins, coumarino-lignoids of Cleome viscosa seeds. Tetrahedron 41: 209-214.   DOI
2 Tanaka, H., Ishihara, M., Ichino, K. and Ito, K. (1988) Total synthesis of coumarinolignans, aquillochin (cleomiscosin C) and cleomiscosin D. Chem. Pharm. Bull. 36: 3833-3837.   DOI
3 Kumar, S., Ray, A. B., Konno, C., Oshima, Y. and Hikino, H. (1988) Cleomiscosin D, a coumarino-lignan from seeds of Cleome viscosa. Phytochemistry 27: 636-638.   DOI
4 Chattopadhyay, S. K., Kumar, S., Kaur, R., Tandon, S. and Rane, S. (2009) Identification and quantification of two antihepatotoxic coumarinolignoids cleomiscosin A and cleomiscosin B in the seeds of Cleome viscosa using liquid chromatography-tandem mass spectrometry. Biomed. Chromatogr. 23: 340-356.   DOI
5 Chattopadhyay, S. K., Kumar, S., Tripathi, S. and Gupta, A. K. (2007) High-performance liquid chromatographic method for identification and quantification of two isomeric coumarinolignoids-cleomiscosin A and cleomiscosin B-in extracts of Cleome viscosa. Biomed. Chromatogr. 21: 1214-1220.   DOI
6 Siddiqui, B. S., Sattar, F. A., Ahmad, F. and Begum, S. (2007) Isolation and structural elucidation of chemical constituents from the fruits of Morinda citrifolia Linn. Arch. Pham. Res. 30: 919-923.   DOI
7 van Gelderen, D. M., de Jong, P. C. and Oterdoom, H. J. (1994) Maples of the world. Timber Press, Portland.
8 Bae, K. H. (2000) The medicinal plants of Korea. Kyo-Hak Publishing Co., Ltd., Seoul, p 302.
9 Lee, G. S., Byun, H. S., Kim, M.-H., Lee, B. M., Ko, S. H., Jung, E. M., Gwak, K. S., Choi, I. G., Kang, H. Y., Jo, H. J., Lee, H. J. and Jeung, E. B. (2008) The beneficial effect of the sap of Acer mono in animal with low-calcium diet-induced osteoporosis-like symptoms. Br. J. Nutr. 100: 1011-1018.   DOI
10 Sharma, U.S., Balasubrmanian, S. V. and Straubinger, R. M. (1995) Pharmaceutical and physical properties of paclitaxel (taxol) complexes with cyclodextrins. J. Pharm. Sci. 84: 1223-1230.   DOI
11 Park, C. H., Son, H. U., Son, M. and Lee, S. H. (2011) Protective effect of Acer mono Max. sap on water immersion restraint stress-induced gastric ulceration. Exp. Ther. Med. 2: 843-848.   DOI
12 Yang, H., Sung, S. H. and Kim, Y. C. (2005) Two new hepatoprotective stilbene glycosides from Acer mono leaves. J. Nat. Prod. 68: 101-103.   DOI
13 Yang, H., Lee, M. K. and Kim, Y. C. (2005) Protective activities of stilbene glycosides from Acer mono leaves against H2O2-induced oxidative damage in primary cultured rat hepatocytes. J. Agric. Food. Chem. 53: 4182-4186.   DOI
14 Karan, M., Sahoo, N. G., Li, L. and Judeh, Z. (2011) Dissolution enhancement of artemisinin with β-cyclodextrin. Chem. Pharm. Bull. 59: 646-652.   DOI
15 Zheng, Y., Haworth, I. S., Zuo, Z., Chow, M. S. S. and Chow, A. H. L. (2005) Physicochemical and structural characterization of quercetin-β-cyclodextrin complexes. J. Pharm. Sci. 94: 1079-1089.   DOI