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Isolation of triterpenoids from the stem bark of Albizia julibrissin and their inhibition activity on ACAT-1 and ACAT-2

Abstract

The dried stem bark of Albizia julibrissin was extracted in 70% aqueous EtOH, and concentrated extracts were partitioned with EtOAc, n-BuOH, and H2O, successively. From the EtOAc fraction, three triterpenoids were isolated through repeated silica gel and octadecyl silica gel column chromatography. Based on nuclear magnetic resonance spectrometry (NMR), mass spectrometry, and infrared spectroscopy spectroscopic data, the chemical structures of the compounds were determined to be lupeol (1), betulinic acid (2), and oleanolic acid (3). This was the first report in which compounds 1, 2, and 3 were isolated from the stem bark of A. itjulibrissin. Since the NMR data for some compounds have been incorrectly or incompletely identified in previous literature, the NMR were revised on the basis of 2-D NMR experiments. Compounds 1, 2, and 3 showed inhibition activity on ACAT-1 with values of 89.3±3.7%, 61.2±3.4%, and 52.5±0.7%, respectively, at a concentration of 50 μg/mL and on ACAT-2 with values of 44.3±2.1%, 55.5±0.3%, and 22.0±2.6%, respectively, at a concentration 50 μg/mL.

References

  • Accad M, Smith SJ, Newland DL, Sanan DA, King LE, Linton MF, Fazio S, and Farese RJ (2000) Massive xanthomatosis and altered composition of atherosclerotic lesions in hyperlipidemic mice lacking acyl CoA: cholesterol acyltransferase 1. J Clin Invest 105, 711–719.

    Article  CAS  Google Scholar 

  • Ahmad VU and Rahman AU (1994) In Handbook of Natural Products Data, pp. 111. Elsevier Science, Amsterdam, Netherlands.

    Google Scholar 

  • Balanehru S and Nagarajan B (1991) Protective effect of olenolic acid and ursolic acid against lipid peroxidation. Biochem Int 24, 981–990.

    CAS  Google Scholar 

  • Brown MS, Dana SE, and Goldstein JL (1975) Cholsterol ester formation in cultured human fibroblasts. J Appl Biol Chem 250, 4025–4027.

    CAS  Google Scholar 

  • Buhman KF, Accad M, and Farese Jr RV (2000) Mammalian acyl-CoA: cholesterol acyltransferase. Biochim. Biophs Act 1529, 142–154.

    CAS  Google Scholar 

  • Chamsuksai P, Choi JS, and Woo WS (1981) 3′,4′,7-Trihydroxyflavone in Albizzia julibrissin. Arch Pharm Res 4, 129–131.

    Article  CAS  Google Scholar 

  • Choi SJ, Yang MC, Choi SU, and Lee KR (2006) Cytotoxic terpenes and lignans from the roots of Ainsliaea acerifolia. Arch Pharm Res 29, 203–208.

    Article  CAS  Google Scholar 

  • Fotie J, Bohle DS, Leimanis ML, Georges E, Rukunga G, and Nkengfack AE (2006) Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda. J Nat Prod 69, 62–67.

    Article  CAS  Google Scholar 

  • Higuchi H, Fukui K, Kinjo J, and Nohara T (1992) Four new glycosides from Albizziae Cortex. III. Chem Pharm Bull 40, 534–535.

    Article  CAS  Google Scholar 

  • Ikeda T, Fujiwara S, Araki K, Kinjo J, Nohara T, and Miyoshi T (1997) Cytotoxic glycosides from Albizzia julibrissin. J Nat Prod 60, 102–107.

    Article  CAS  Google Scholar 

  • Jeong TS, Kim JR, Kim KS, Cho KH, Bae KH, and Lee WS (2004) Inhibitory effects of multi-substituted benzylidenzethiazolidine-2,4-diones on LDL oxidation. Bioorg Med Chem 12, 4017–4023.

    Article  CAS  Google Scholar 

  • Kang SS and Woo WS (1983) Sapogenins from Albizzia julirissin. Arch Pharm Res 6, 25–28.

    Article  CAS  Google Scholar 

  • Kang TH, Jeong ST, Kim NY, Higuchi R, and Kim YC (2000) Sedative activity of two flavonol glycosides isolated from the flowers of Albizzia julibrissin Durazz. J Ethnopharmacol 71, 321–323.

    Article  CAS  Google Scholar 

  • Kinjo F, Fukui K, Higuchi H, and Nohara T (1991a) The first isolation of lignin tri- and tetra-glycosides. Chem Pharm Bull 39, 1623–1625.

    Article  CAS  Google Scholar 

  • Kinjo J, Higuchi H, Fukui K, and Nohara T (1991b) Lignoids from Albizziae Cortex.. A biodegradation pathway of syringaresinol. Chem Pharm Bull 39, 2952–2955.

    Article  CAS  Google Scholar 

  • Lee CH, Jeong TS Choi YK, Hyun BW, Oh GT, Kim EH, Kin JR, Han JI, and Bok SH (2001) Anti-atherogenic effect of citrus flavonoids, maringin and naringenin, associated with hepatic AC AT and aortic VCAM-1 and MCP-1 in high cholesterol-fed rabbits. Biochem Biophys Res Commun 284, 681–688.

    Article  CAS  Google Scholar 

  • Lee DY, Jung LK, Lyu HN, Jeong TS, Lee YH, and Baek NI (2009) Triterpenoids from the fruits of Cornus kousa Burg, as human acyl-CoA: cholesterol acyltransferase inhibitors. Food Sci Biotechnol 18, 223–227.

    CAS  Google Scholar 

  • Mahato SB and Kundu AP (1994) 13C NMR spectra of pentacyclic triterpenoids-a complilation and some salient features. Phytochemistry 37, 1517–1575.

    Article  CAS  Google Scholar 

  • Matsunaga S, Tanaka R, and Akagi M (1988) Triterpenoids from Euphorbia Maculat. Phytochemistry 27, 535–537.

    Article  CAS  Google Scholar 

  • Namba T (1980) In Colored Illustrations of Wakan Yaku (II), pp. 157–158. Hoikusha Publishing Co., Osaka, Japan.

    Google Scholar 

  • Rrecher P and Chan CT (1980) Properties of acyl-CoA:cholesterol ancyltransferase in aortic microsomes from atherosclerotic rabbits. Biochim Biophys Acta 617, 458–471.

    Google Scholar 

  • Rudel LL, Lee RG, and Cockman TL (2001) Acyl coenzyme A: cholesterol acyltransferase types 1 and 2: Structure and function in atherosclerosis. Curr Opin Lipidol 12, 121–127.

    Article  CAS  Google Scholar 

  • The Pharmacopoeia Committee of People’s Republic of China (1995) In Pharmacopoeia (I), pp. 119–120. People Health Press, Beijing, China.

    Google Scholar 

  • Wei DH, Qiao SY, and Zhao YM (2004) Advances in study on bark of Albizzia julibrissin. China J Chin Mater Med 29, 619–624.

    CAS  Google Scholar 

  • You YH, Woo WS, Choi JS, and Kang SS (1982) Isolation of a new sapogenin from Albizzia julibrissin. {Arch Pharm Res} 5, 33–38.

    Article  CAS  Google Scholar 

  • Zou K, Tong WY, Liang H, Cui JR, Tu GZ, Zhao YY, and Zhang RY (2005) Diastereoisomeric saponins from Albizia julibrissin. Carbohydrate Res 340, 1329–1334.

    Article  CAS  Google Scholar 

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Correspondence to Nam-In Baek.

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Baek, MY., Cho, JG., Lee, DY. et al. Isolation of triterpenoids from the stem bark of Albizia julibrissin and their inhibition activity on ACAT-1 and ACAT-2. J. Korean Soc. Appl. Biol. Chem. 53, 310–315 (2010). https://doi.org/10.3839/jksabc.2010.048

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