Skip to main content

Advertisement

Log in

Evaluation of the anti-osteoporosis and antioxidant activities of phenolic compounds from Euphorbia maculata

  • Article
  • Published:
Journal of the Korean Society for Applied Biological Chemistry Submit manuscript

Abstract

Antioxidant and anti-osteoporosis activities of extracts and chemical constituents from the whole plant of Euphorbia maculata were investigated. The MeOH extract, as well as EtOAc and H2O fractions (10.0 μg/mL), exhibited potent antioxidant activities. Their oxygen radical absorbance capacity and cupric ion reducing antioxidant capacity values were 27.07±0.31 to 28.47±0.36 and 43.86±0.26 to 46.67±0.34 fold higher than those of 1.0 μM Trolox, respectively. The MeOH extract and EtOAc fraction (at 10.0 μg/mL) also significantly suppressed excessive bone resorption by osteoclasts with tartrate-resistant acid phosphatase (TRAP) activity values of 154.90±4.25 and 163.95±9.77%, respectively. Bioassay guided isolation of the EtOAc and H2O fractions afforded 19 known compounds (119). Of these, compounds 18, and 1315 showed good antioxidant activity based on peroxyl radical-scavenging and reducing capacity assays, whereas compounds 1, 4, 7, and 14 showed the most significant inhibitory effect with TRAP activity values ranging from 121.31±1.41 to 110.00±3.74% relative to the control.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Amakura Y, Kawada K, Hatano T, Agata I, Sugaya T, Nishibge S, Okuda T, and Yoshida T. (1997) Four new hydrolyzable tannins and an acylated flavonol glycoside from Euphorbia maculata. Can J Chem 75, 727–33.

    Article  CAS  Google Scholar 

  • Aruoma OI, Deiana M, Jenner A, Halliwell B, Kaur H, Banni S, Corongiu FP, Dessi MA, and Aeschbach R. (1998) Effect of hydroxytyrosol found in extra virgin olive oil on oxidative DNA damage and on low-density lipoprotein oxidation. J Agric Food Chem 46, 5181–7.

    Article  CAS  Google Scholar 

  • Boyle WJ, Simonet WS, and Lacey DL. (2003) Osteoclast differentiation and activation. Nature 423, 337–42.

    Article  CAS  Google Scholar 

  • Chung KT, Wong TY, Wei CI, Huang YW, and Lin Y. (1998) Tannins and human health: a review. Crit Rev Food Sci Nutr 38, 421–64.

    Article  CAS  Google Scholar 

  • Ercil D, Kaloga M, Radtke OA, Sakar MK, Kiderlen AF, and Kolodziej H. (2005) O-galloyl flavonoids from Geranium pyrenaicum and their in vitro antileishmanial activity. Turk J Chem 29, 437–43.

    CAS  Google Scholar 

  • Gao DF, Xu M, Yang CR, Xu M, and Zhang YJ. (2010) Phenolic Antioxidants from the Leaves of Camellia pachyandra Hu. J Agric Food Chem 58, 8820–4.

    Article  CAS  Google Scholar 

  • Halleen JM, Raisanen SR, Alatalo SL, and Vaananen HK. (2003) Potential function for the ROS-generating activity of TRACP. J Bone Miner Res 18, 1908–11.

    Article  CAS  Google Scholar 

  • Hu FB and Willett WC. (2002) Optimal diets for prevention of coronary heart disease. J Am Med Assoc 288, 2569–78.

    Article  CAS  Google Scholar 

  • Isobe T, Ito N, and Noda Y. (1980) Minor flavonoids of Polygonum nodosum. Phytochemistry 19, 1877.

    Article  CAS  Google Scholar 

  • Isobe T, Kanazawa K, Fujimura M, and Noda Y. (1981) Flavonoids of Polygonum sieboldi and P. filiforme. Bull Chem Soc Jpn 54, 3239.

    Article  CAS  Google Scholar 

  • Kang W, Wang J, and Cao N. (2012) Inhibitory activity of Euphorbia humifusa for α-glucosidase in vitro and in vivo. Chem Nat Compd 48, 886–8.

    Article  CAS  Google Scholar 

  • Kazuma K, Noda N, and Suzuki M. (2003) Malonylated flavonol glycosides from the petals of Clitoria ternatea. Phytochemistry 62, 229–37.

    Article  CAS  Google Scholar 

  • Kiem PV, Nguyen XC, Nguyen XN, Thu VK, Ban NK, Minh CV, Tai BH, Hai TN, Lee SH, Jang HD, and Kim YH. (2011) Antioxidant activity of a new C-glycosylflavone from the leaves of Ficus microcarpa. Bioorg Med Chem Lett 21, 633–7.

    Article  CAS  Google Scholar 

  • Kim HY, Moon BH, Lee HJ, and Choi DH. (2004) Flavonol glycosides from the leaves of Eucommia ulmoides O. with glycation inhibitory activity. J Ethnopharmacol 93, 227–30.

    Article  CAS  Google Scholar 

  • Kong YY, Yoshida H, Sarosi I, Tan HL, Timms E, Capparelli C, Morony S, Oliveira-Dos-Santos AJ, Van G, Itie A, Khoo W, Wakeham A, Dunstan CR, Lacey DL, Mak TW, Boyle WJ, and Penninger JM. (1999) OPGL is a key regulator of osteoclastogenesis, lymphocyte development and lymph-node organogenesis. Nature 397, 315–23.

    Article  CAS  Google Scholar 

  • Kurihara H, Fukami H, Asami S, Toyoda Y, Nakai M, Shibata H, and Yao XS. (2004) Effects of Oolong tea on plasma antioxidative capacity in mice loaded with restraint stress assessed using the oxygen radical absorbance capacity (ORAC) assay. Biol Pharm Bull 27, 1093–8.

    Article  CAS  Google Scholar 

  • Lim YA, Mei MC, Kusumoto IT, Miyashiro H, Hattori M, Gupta MP, and Correa M. (1997) HIV-1 reverse transcriptase inhibitory principles from Chamaesyce hyssopifolia. Phytother Res 11, 22–7.

    Article  CAS  Google Scholar 

  • Li XC, Elsohly HN, Hufford CD, and Clark AM. (1999) NMR assignments of ellagic acid derivatives. Magn Reson Chem 37, 856–9.

    Article  CAS  Google Scholar 

  • Li YL, Li J, Wang NL, and Yao XS. (2008) Flavonoids and a new polyacetylene from Bidens parviflora willd. Molecules 13, 1931–41.

    Article  CAS  Google Scholar 

  • Matsunaga S, Tanaka R, and Akagi M. (1988) Triterpenoids from Euphorbia maculata. Phytochemistry 27, 535–7.

    Article  CAS  Google Scholar 

  • Park SY, Kim JS, Lee SY, Bae KH, and Kang SS. (2008) Chemical constituents of Lathyrus davidii. Nat Prod Sci 14, 281–8.

    CAS  Google Scholar 

  • Pietta PG. (2000) Flavonoids as antioxidants. J Nat Prod 63, 1035–42.

    Article  CAS  Google Scholar 

  • Rui-Lin N, Tanaka T, Zhou J, and Tanaka O. (1982) Phlorizin and trilobatin, sweet dihydrochalcone-glucosides from leaves of Lithocarpus litseifolius (Hance) Rehd. (Fagaceae). Agric Biol Chem 46, 1933–4.

    Article  CAS  Google Scholar 

  • Sontakke AN and Tare RS. (2002) A duality in the roles of reactive oxygen species with respect to bone metabolism. Clin Chim Acta 318, 145–8.

    Article  CAS  Google Scholar 

  • Sudjaroen Y, Hull WE, Erben G, Wuertele G, Changbumrung S, Ulrich CM, and Owen RW. (2012) Isolation and characterization of ellagitannins as the major polyphenolic components of Longan (Dimocarpus longan Lour) seeds. Phytochemistry 77, 226–37.

    Article  CAS  Google Scholar 

  • Tanaka T, Nonaka G, and Nishioka I. (1990) Tannins and related compounds. ai]C. Reaction of dehydrohexahydroxydiphenic acid esters with bases, and its application to the structure determination of pomegranate tannins, granatins A and B. Chem Pharm Bull 38, 2424–8.

    Article  CAS  Google Scholar 

  • Ternai B and Markham KR. (1976) Carbon-13 NMR studies of flavonoids. I. Flavones and flavonols. Tetrahedron 32, 565–9.

    Article  CAS  Google Scholar 

  • Wei W, Pan Y, Chen Y, Lin C, Wei T, and Zhao S. (2005) Carboxylic acids from Phyllanthus urinaria. Chem Nat Compd 41, 17–21.

    Article  CAS  Google Scholar 

  • Xue HG, Wang H, Li DZ, Xue CY, and Wang QZ. (2008) Differentiation of the traditional Chinese medicinal plants Euphorbia humifusa and E. maculata from adulterants by TaqMan real-time polymerase chain reaction. Planta Med 74, 302–4.

    Article  CAS  Google Scholar 

  • Zhang HL, Nagatsu A, Okuyama H, Mizukami H, and Sakakibara J. (1998) Sesquiterpene glycosides from cotton oil cake. Phytochemistry 48, 665–8.

    Article  CAS  Google Scholar 

  • Zhang JK, Yang L, Meng GL, Yuan Z, Fan J, Li D, Chen JZ, Shi TY, Hu HM, Wei BY, Luo ZJ, and Liu J. (2013) Protection by salidroside against bone loss via inhibition of oxidative stress and bone-resorbing mediators. PLoS One 8, e57251.

    Article  Google Scholar 

  • Zheng G, Xu L, Wu P, Xie H, Jiang Y, Chen F, and Wei X. (2009) Polyphenols from longan seeds and their radical-scavenging activity. Food Chem 116, 433–6.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Hae Dong Jang or Young Ho Kim.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Luyen, B.T.T., Tai, B.H., Thao, N.P. et al. Evaluation of the anti-osteoporosis and antioxidant activities of phenolic compounds from Euphorbia maculata . J Korean Soc Appl Biol Chem 57, 573–579 (2014). https://doi.org/10.1007/s13765-014-4157-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13765-014-4157-2

Keywords

Navigation