Back
 JACEN  Vol.1 No.1 , November 2012
Analysis of apigenin in Blumea balsamifera Linn DC. and its inhibitory activity against aldose reductase in rat lens
Abstract: To investigate the therapeutic potentials of na- tural sources, stepwise polarity fractions of Blumea balsamifera were tested for their ability to inhibit aldose reductase (AR) activity in rat lenses. Of these, the ethyl acetate (EtOAc) fraction exhibited a unique AR inhibitory activity (IC50 value, 0.11 μg/mL). Apigenin was identified from the active EtOAc fraction and exhibited high AR inhibitory activity (IC50 value, 4.03 μM). The content of apigenin was measured in B. balsamifera (0.47 mg/g) by HPLC/UV analysis. Our result suggests that B. balsamifera could be a useful natural source for the development of a novel AR inhibitory agent against diabetic complications.
Cite this paper: D. Lee, S. Mok, C. Choi, E. Cho, H. Kim and S. Lee, "Analysis of apigenin in Blumea balsamifera Linn DC. and its inhibitory activity against aldose reductase in rat lens," Journal of Agricultural Chemistry and Environment, Vol. 1 No. 1, 2012, pp. 28-33. doi: 10.4236/jacen.2012.11005.
References

[1]   Osaki, N., Koyano, T., Kowithayakorn, T., Hayashi, M., Komiyama, K. and Ishibashi, M. (2005) Sesquiterpenoids and plasmin-inhibitory flavonoids from Blumea balsamifera. Journal of Natural Products, 68, 447-449. doi:10.1021/np049622e

[2]   Zhari, I., Norhayati, I. and Jaafar, L. (1999) Malaysian herbal monograph. Malaysian Monograph Committee, Kuala Lumpur, 9-12.

[3]   Perry, L.M. (1980) Medicinal plants of east and southeast Asia. Massachusetts Institute of Technology Press, Cambridge, 87.

[4]   Santos, A.C. (1981) Philippines plants and their contained natural products. National Relief Charities, Manila, 2121.

[5]   Ruangrungsi, N., Tantivatana, P., Tappayuthpijarn, P., Borris, R.P. and Cordell, G.A. (1985) Traditional medicinal plants of Thailand VI. Isolation of cryptomeridiol from Blumea balsamifera (Compositae). Journal of the Science Society of Thailand, 11, 47-50. doi:10.2306/scienceasia1513-1874.1985.11.047

[6]   Ahmad, F.B. and Ismail, G. (2003) Medicinal plants used by Kadazandusun communities around crocker range. ASEAN Review of Biodiversity and Environmental Conservation, 1, 1-10.

[7]   Asolkar, L.V., Kakkar, K.K. and Chakre, O.J. (1992) Second supplement to glossary of Indian medicinal plants with active principles, Part-1 (A-K). CSIR, New Delhi, 414.

[8]   Ragasa, C.Y., Co, A.L. and Rideout, J.A. (2005) Antifungal metabolites from Blumea balsamifera. Natural Product Sciences, 19, 231-237. doi:10.1080/14786410410001709773

[9]   Kubota, H., Kojima-Yuasa, A., Morii, R., Huang, X., Norikura, T., Rho, S.N. and Matsui-Yuasa, I. (2009) Anti-obesity effect of Blumea balsamifera extract in 3T3-L1 preadipocytes and adipocytes. The American Journal of Chinese Medicine, 37, 843-854. doi:10.1142/S0192415X09007326

[10]   Xu, S.B., Chen, W.F., Liang, H.Q., Lin, Y.C., Deng, Y.J. and Long, K.H. (1993) Protective action of blumeatin against experimental liver injuries. Chinese Pharmacological Bulletin, 14, 376-378.

[11]   Norikura, T., Kojima-Yuasa, A., Shimizu, M., Huang, X., Xu, S., Kametani, S., Rho, S.K., Kennedy, D.O. and Matsui-Yuasa, I. (2008) Anticancer activity and mechanisms of Blumea balsamifera extract in hepatocellular carcinoma cells. The American Journal of Chinese Medicine, 36, 411-424. doi:10.1142/S0192415X08005862

[12]   Ruangrungsi, N., Tappayuthpijaran, P. and Tantivatana, P. (1981) Traditional medicinal plants of Thailand I. Isolation and structure elucidation of two new flavonoids, (2R,3R)-dihydroquercetin-40-methyl ether and (2R,3R)-dihydroquercetin-40,7-dimethyl ether from Blumea balsamifera. Journal of Natural Products, 44, 541-545. doi:10.1021/np50017a005

[13]   Barua, N.C. and Sharma, R.P. (1992) (2R,3R)-7,50-dimethoxy-3,5,20-trihydroxyflavanone from Blumea balsamifera. Phytochemistry, 31, 4040. doi:10.1016/S0031-9422(00)97584-8

[14]   Fazilatun, N., Zhari, I., Nornisah, M. and Mas Rosemal, H.M.H. (2001) Phytochemical investigation on Blumea balsamifera DC. Journal of Tropical Medicinal Plants, 2, 17-22.

[15]   Fazilatun, N., Zhari, I., Nornisah, M. and Mas Rosemal, H.M.H. (2004) Free radical-scavenging activity of organic extracts and of pure flavonoids of Blumea balsamifera DC leaves. Food Chemistry, 88, 243-252. doi:10.1016/j.foodchem.2004.01.041

[16]   Sato, S. and Kador, P.F. (1990) Inhibition of aldehyde reductase by aldose reductase inhibitors. Biochemical Pharmacology, 40, 1033-1042. doi:10.1016/0006-2952(90)90490-C

[17]   Stochmal, A., Simonet, A.M., Macias, F.A., Oliveira, M.A., Abreu, J.M., Nash, R. and Oleszek, W. (2001) Acylated apigenin glycosides from alfalfa (Medicago sativa L.) var. Artal. Phytochemistry, 57, 1223-1226. doi:10.1016/S0031-9422(01)00204-7

[18]   Lee, S., Kim, K.S., Jang, J.M., Park, Y., Kim, Y.B. and Kim, B.K. (2002) Phytochemical constituents from the herba of Artemisia apiacea. Archives of Pharmacal Research, 25, 285-288. doi:10.1007/BF02976627

[19]   Duthie, G. and Crozier, A. (2000) Plant-derived phenolic antioxidants. Current Opinion in Clinical Nutrition & Metabolic Care, 3, 447-451. doi:10.1097/00075197-200011000-00006

[20]   Miean, K.H. and Mohamed, S. (2001) Flavonoid (myricetin, quercetin, kaempferol, luteolin, and apigenin) content of edible tropical plants. Journal of Agricultural and Food Chemistry, 49, 3106-3112. doi:10.1021/jf000892m

[21]   Kim, H.P., Mani, I., Iversen, L. and Ziboh, V.A. (1998) Effects of naturally-occurring flavonoids and biflavonoids on epidermal cyclooxygenase and lipoxygenase from guinea-pigs. Prostaglandins, Leukotrienes and Essential Fatty Acids, 58, 17-24. doi:10.1016/S0952-3278(98)90125-9

[22]   Singh, J.P., Selvendiran, K., Banu, S.M., Padmavathi, R. and Sakthisekaran, D. (2004) Protective role of apigenin on the status of lipid peroxidation and antioxidant defense against hepatocarcinogenesis in Wistar albino rats. Phytomedicine, 11, 309-314. doi:10.1078/0944711041495254

[23]   Khan, T.H. and Sultana, S. (2006) Apigenin induces apoptosis in Hep G2 cells: Possible role of TNF-α and IFN-γ. Toxicology, 217, 206-212. doi:10.1016/j.tox.2005.09.019

[24]   Cai, J., Zhao, X.L., Liu, A.W., Nian, H. and Zhang, S.H. (2011) Apigenin inhibits hepatoma cell growth through alteration of gene expression patterns. Phytomedicine, 18, 366-373. doi:10.1016/j.phymed.2010.08.006

[25]   Shukla, S. and Gupta, S. (2009) Apigenin suppresses insulin-like growth factor I receptor signaling in human prostate cancer: An in vitro and in vivo study. Molecular Carcinogenesis, 48, 243-252. doi:10.1002/mc.20475

[26]   Gupta, S., Afaq, F. and Mukhtar, H. (2002) Involvement of nuclear factor-kappa B, Bax and Bcl-2 in induction of cell cycle arrest and apoptosis by apigenin in human prostate carcinoma cells. Oncogene, 21, 3727-3738. doi:10.1038/sj.onc.1205474

[27]   Shukla, S. and Gupta, S. (2007) Apigenin-induced cell cycle arrest is mediated by modulation of MAPK, PI3K- Akt, and loss of cyclin D1 associated retinoblastoma dephosphorylation in human prostate cancer cells. Cell Cycle, 6, 1102-1114. doi:10.4161/cc.6.9.4146

[28]   Shukla, S., MacLennan, G.T., Flask, C.A., Fu, P., Mishra, A., Resnick, M.I. and Gupta, S. (2007) Blockade of β-catenin signaling by plant flavonoid apigenin suppresses prostate carcinogenesis in TRAMP mice. Cancer Research, 67, 6925-6935. doi:10.1158/0008-5472.CAN-07-0717

[29]   Hu, X.W., Meng, D. and Fang, J. (2008) Apigenin inhibited migration and invasion of human ovarian cancer A2780 cells through focal adhesion kinase. Journal of Carcinogenesis, 29, 2369-2376. doi:10.1093/carcin/bgn244

[30]   Kaur, P., Shukla, S. and Gupta, S. (2008) Plant flavonoid apigenin inactivates Akt to trigger apoptosis in human prostate cancer: An in vitro and in vivo study. Journal of Carcinogenesis, 29, 2210-2217. doi:10.1093/carcin/bgn201

[31]   Lee, W.J., Chen, W.K., Wang, C.J., Lin, W.L. and Tseng, T.H. (2008) Apigenin inhibits HGF promoted invasive growth and metastasis involving blocking PI3K/Akt pathway and β4 integrin function in MDA-MB-231 breast cancer cells. Toxicology and Applied Pharmacology, 226, 178-191. doi:10.1016/j.taap.2007.09.013

[32]   Lee, Y.M., Kim, N.H., Kim, J.M., Kim, Y.S., Jang, D.S., Kim, J.H., Bae, K.H. and Kim, J.S. (2008) Screening of inhibitory effect on aldose reductase of Korean herbal medicines and preventive effect of Catalpa bignonioides against xylose-induced lens opacity. Korean Journal of Pharmacognosy, 39, 165-173.

[33]   Franzen, C.A., Amargo, E., Todorovi?, V., Desai, B.V., Huda, S., Mirzoeva, S., Chiu, K., Grzybowski, B.A., Chew, T.L., Green, K.J. and Pelling, J.C. (2009) The chemopreventive bioflavonoid apigenin inhibits prostate cancer cell motility through the focal adhesion kinase/Src signaling mechanism. Cancer Prevention Research, 2, 830-841. doi:10.1158/1940-6207.CAPR-09-0066

[34]   Lee, Y.H., Lee, I.R., Woo, W.S. and Park, C.H. (1988) Flavonoids of Elscholtzia cristata. Archives of Pharmacal Research, 11, 247-249. doi:10.1007/BF02861317

[35]   Lee, H.B., Kwak, J.H., Zee, O.P. and Yoo, S.J. (1994) Flavonoids from Circum rhinoceros. Archives of Pharmacal Research, 17, 273-277. doi:10.1007/BF02980460

[36]   Avallone, R., Zanoli, P., Puia, G., Kleinschnitz, M., Schreier, P. and Baraldi, M. (2000) Pharmacological profile of apigenin, a flavonoid isolated from Matricaria chamomilla. Biochemical Pharmacology, 59, 1387-1394. doi:10.1016/S0006-2952(00)00264-1

[37]   Zanoli, P., Avallone, R. and Baraldi, M. (2000) Behavioral characterization of the flavonoids apigenin and chrysin. Fitoterapia, 71, S117-S123. doi:10.1016/S0367-326X(00)00186-6

[38]   Collins, J.G. and Corder, C.N. (1977) Aldose reductase and sorbitol dehydrogenase distribution in substructures of normal and diabetic rat lens. Investigative Ophthalmology and Visual Science, 16, 242-243.

[39]   Kawanishi, K., Ueda, H. and Moriyasu, M. (2003) Aldose reductase inhibitors from the nature. Current Medicinal Chemistry, 10, 1353-1374. doi:10.2174/0929867033457304

[40]   Yawadio, R., Tanimori, S. and Morita, N. (2007) Identification of phenolic compounds isolated from pigmented rices and their aldose reductase inhibitory activities. Food Chemistry, 101, 1616-1625. doi:10.1016/j.foodchem.2006.04.016

[41]   Kim, H.M., Lee, J.M., Lee, K.H., Ahn, Y.H. and Lee, S. (2011) Aldose reductase inhibition by luteolin derivatives from Parasenecio pseudotaimingasa. Natural Product Sciences, 17, 367-371.

[42]   Mok, S.-Y., Lee, J.M., Kim, H.M., Lee, D.G., Yoon, Y.-H., Cho, E.J. and Lee, S. (2011) Inhibition of aldose reductase on rat lens by tartary buckwheat. Natural Product Sciences, 17, 230-233.

[43]   Mok, S.-Y., Lee, S., Kim, H.M., Lee, J.M., Lee, D.G., Ahn, Y.H., Park, C.-G., Cho, E.J. and Lee, S. (2011) Inhibition of rat lense aldose reductase by flavonoids from dandelions. Natural Product Sciences, 17, 130-134.

 
 
Top