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Two new naphthalene glucosides and other bioactive compounds from the carnivorous plant Nepenthes mirabilis

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Abstract

Two new naphthalene diglucosides named nepenthosides A (1) and B (2), together with eleven known compounds (3–13), were isolated from the carnivorous plant Nepenthes mirabilis. The structures of these compounds were elucidated based on extensive spectroscopic analysis, including 1D- and 2D-NMR, and MS. The antioxidant activities of compounds 1–13 were evaluated in terms of their peroxyl radical-scavenging (trolox equivalent, TE) and reducing capacities. All isolates showed peroxyl radical-scavenging and reducing activities at concentrations of 1.0 and 10.0 μM. Anti-osteoporotic activities were investigated using murine osteoclastic RAW 264.7 cells. Compounds 1–7 and 9–12 significantly suppressed tartrate-resistant acid phosphatase activity down to 91.13 ± 1.18 to 42.39 ± 1.11 %, relative to the control (100 %) in nuclear factor-κB ligand (RANκL)-induced osteoclastic RAW 264.7 macrophage cells.

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References

  • Arai, M., Y. Shibata, K. Pugdee, Y. Abiko, and Y. Ogata. 2007. Effects of reactive oxygen species (ROS) on antioxidant system and osteoblastic differentiation in MC3T3-E1 cells. IUBMB Life 59: 27–33.

    Article  CAS  PubMed  Google Scholar 

  • Aruoma, O.I., M. Deiana, A. Jenner, B. Halliwell, H. Kaur, S. Banni, F.P. Corongiu, M. Assunta Dessí, and R. Aeschbach. 1998. Effect of hydroxytyrosol found in extra virgin olive oil on oxidative DNA damage and on low-density lipoprotein oxidation. Journal of Agricultural Food Chemistry 46: 5181–5187.

    Article  CAS  Google Scholar 

  • Aung, H.H., L.S. Chia, N.K. Goh, T.F. Chia, A.A. Ahmed, P.W. Pare, and T.J. Mabry. 2002. Phenolic constituents from the leaves of the carnivorous plant Nepenthes gracilis. Fitoterapia 73: 445–447.

    Article  CAS  PubMed  Google Scholar 

  • Boyle, W.J., W.S. Simonet, and D.L. Lacey. 2003. Osteoclast differentiation and activation. Nature 423: 337–342.

    Article  CAS  PubMed  Google Scholar 

  • Budzianowski, J. 1995. Naphthoquinones of Drosera spathulata from in vitro cultures. Phytochemistry 40: 1145–1148.

    Article  CAS  Google Scholar 

  • Cannon, J.R., V. Lojanapiwatna, C.L. Raston, W. Sinchai, and A.H. White. 1980. The quinones of Nepenthes rafflesiana. Australian Journal Chemistry 33: 1075–1093.

    Google Scholar 

  • Chang, Z.W., and D.Q. Yu. 1998. Lignan and acetylenic glycosides from Aster auriculatus. Phytochemistry 48: 711–717.

    Article  Google Scholar 

  • Gondo, M., N. Tanaka, T. Tanaka, K. Shimomura, F. Nakanishi, and K. Ishimaru. 1999. A naphthalene glycoside from callus cultures of Diospyros kaki. Phytochemistry 51: 879–881.

    Article  CAS  Google Scholar 

  • Hideaki, O., M. Takeuchi, S. Inoshiri, T. Sato, and K. Yamasaki. 1989. Phenolic compounds from Coix lachryma-jobi var. Ma-yuen. Phytochemistry 28: 883–886.

    Article  Google Scholar 

  • Hisham, A., G.J. Kumar, Y. Fujimoto, and N. Hara. 1995. Salacianone and salacianol, two triterpenes from Salacia beddomei. Phychochemistry 40: 1227–1231.

    Article  CAS  Google Scholar 

  • Ho, P.H. 2003. Vietnamese plants, vol. 1, 532–533. Ho Chi Minh city: Young publisher.

    Google Scholar 

  • Inagaki, J., N. Watanabe, J. Moon, A. Yagaki, K. Sakata, K. Ina, and S. Luo. 1995. Glycosidic aroma precursors of 2-phenylethyl and benzyl alcohols from Jasminum sambac flowers. Bioscience Biotechnology Biochemistry 59: 738–739.

    Article  CAS  Google Scholar 

  • Jean-Frédéric, F.W., A.W. Ibtisam, A. Marzuki, N.F. Thomas, A.A. Kadir, A.H.A. Hadi, K. Awang, A.A. Latiff, P. Richomme, J. Delaunay, and A. Heimiol. 2001. A new dimeric stilbenoid from Neobalanocarpus heimii. Tetrahedron Letters 42: 4895–14897.

    Article  Google Scholar 

  • Kurihara, H., H. Fukami, S. Asami, Y. Toyoda, M. Nakai, H. Shibata, and X.S. Yao. 2004. Effects of oolong tea on plasma antioxidative capacity in mice loaded with restraint stress assessed using the oxygen radical absorbance capacity (ORAC) assay. Biological & Pharmaceutical Bulletin 27: 1093–11098.

    Article  CAS  Google Scholar 

  • Likhitwitayawuid, K., R. Kaewamatawong, N. Ruangrungsi, and J. Krungkrai. 1998. Antimalarial naphthoquinones from Nepenthes thorelii. Planta Medica 64: 237–241.

    Article  CAS  PubMed  Google Scholar 

  • Loi, D.T. 2004. Vietnamese medicinal plants and medicaments, vol. 1, 776. Hanoi: Health Publishing House.

  • Lorenzo, J., M. Horowitz, and Y. Choi. 2008. Osteoimmunology: interactions of the bone and immune system. Endocrine Reviews 29: 403–440.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

  • Mei, I.C., M.H. Lai, H.Y. Ming, R.R. Wu, and C.N. Lin. 1997. Phenolics from Hypericum geminiflorum. Phytochemistry 44: 943–947.

    Article  Google Scholar 

  • Lee, Min A., H.K. Lee, S.H. Kim, Y.C. Kim, and S.H. Sung. 2010. Chemical constituents of Alnus firma and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia. Planta Medica 76: 1007–1010.

    Article  CAS  PubMed  Google Scholar 

  • Miyase, T., A. Ueno, N. Takizawa, H. Kobayashi, and H. Oguchi. 1987. Studies on the glycosides of Epimedium grandiforum Morr.var.thunbergianum (Miq.) Nakal [II]. Chemical and Pharmaceutical Bulletin 35: 3713–3719.

    Article  CAS  Google Scholar 

  • Monthong, W., S. Pitchuanchom, N. Nuntasaen, and W. Pompimon. 2011. (+)-Syringaresinol lignan from new species Magnolia thailandica. American Journal of Applied Science 8: 1268–1271.

    Article  CAS  Google Scholar 

  • Nazrun, A.S., M. Norazlina, M. Norliza, and S. Ima Nirwana. 2011. Tocotrienols as an anti osteoporotic agent: the progress so far. Internation Journal Osteoporosis Metabolism Disorders 4: 1–14.

    Article  CAS  Google Scholar 

  • Pomilio, A., C. Casabuono, and B. Alicia. 1994. Lignans and a stibenen from Festuca argentina. Phytochemistry 45: 479–483.

    Google Scholar 

  • Rischer, H., A. Hamm, and G. Bringmann. 2002. Nepenthes insignis uses a C2-portion of the carbon skeleton of l-alanine acquired via carnivorous organs, to build up the allelochemical plumbagin. Phytochemistry 59: 603–609.

    Article  CAS  PubMed  Google Scholar 

  • Sontakke, A.N., and T.R. Sare. 2002. A duality in the roles of reactive oxygen species with respect to bone metabolism. Clinica Chimica Acta 318: 145–148.

    Article  CAS  Google Scholar 

  • Srinivasan, S., A. Koenigstein, J. Joseph, L. Sun, B. Kalyanaraman, M. Zaidi, and N.G. Avadhani. 2010. Role of mitochondrial reactive oxygen species in osteoclast differentiation. Annals of New York Academy of Sciences 1192: 245–252.

    Article  CAS  Google Scholar 

  • Tanaka, T., T. Nakashima, T. Ueda, K. Tomii, and I. Kouno. 2007. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chemical and Pharmaceutical Bulletin 55: 899–901.

    Article  CAS  PubMed  Google Scholar 

  • Zhang, J.K., L. Yang, G.L. Meng, Z. Yuan, J. Fan, D. Li, J.Z. Chen, T.Y. Shi, H.M. Hu, B.Y. Wei, and Z.J. Luo. 2013. Protection by salidroside against bone loss via inhibition of oxidative stress and bone-resorbing mediators. PLoS One 8: e57251.

    Article  PubMed Central  CAS  PubMed  Google Scholar 

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Acknowledgments

This work was financially supported by Vietnam National Foundation for Science & Technology Development (No. 104.01–2012.59) and the Priority Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology (2009–0093815), Republic of Korea. The authors are grateful to the Institute of Chemistry, VAST for the provision of the spectroscopic instrument.

Conflict of interest

The authors have declared that there is no conflict of interest.

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    Authors and Affiliations

    1. Institute of Marine Biochemistry (IMBC), Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam

      Nguyen Van Thanh, Nguyen Phuong Thao, Le Duc Dat, Phan Thi Thanh Huong, Nguyen Xuan Cuong, Nguyen Hoai Nam, Phan Van Kiem & Chau Van Minh

    2. College of Pharmacy, Chungnam National University, Daejeon, 305-764, Republic of Korea

      Nguyen Phuong Thao & Young Ho Kim

    3. Department of Food and Nutrition, Hannam University, Daejeon, 305-811, Republic of Korea

      Sang Hyun Lee & Hae Dong Jang

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    1. Nguyen Van Thanh
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    Correspondence to Chau Van Minh or Young Ho Kim.

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    Nguyen Van Thanh and Nguyen Phuong Thao have contributed equally to this work.

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    Thanh, N.V., Thao, N.P., Dat, L.D. et al. Two new naphthalene glucosides and other bioactive compounds from the carnivorous plant Nepenthes mirabilis . Arch. Pharm. Res. 38, 1774–1782 (2015). https://doi.org/10.1007/s12272-015-0576-9

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