Chemical constituents from Lobelia chinensis and their anti-virus and anti-inflammatory bioactivities

Abstract

In total, forty six compounds, including the novel compound lobechine (1), were characterized from the methanol extracts of Lobelia chinensis. The chemical structures of known metabolites were identified by comparing their spectroscopic and physical data with compounds reported in the literature. The structure of lobechine (1) was comprehensively established with the aid of 1D and 2D NMR spectroscopic analyses. In addition, selected isolates were screened for their inhibition of HSV-1 replication, superoxide anion generation, and elastase release. Among the tested compounds, scoparone (10) exhibited significant inhibition of superoxide anion generation with IC50 of 6.14 ± 1.97 μM and lobechine (1) exhibited moderate inhibition of elastase release with IC50 of 25.01 ± 6.95 μM, respectively.

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References

  1. Chaturvedula, V. S. P. and Schilling, J. K., Two new triterpene esters from the twigs of Brachylaena ramiflora from the Madagascar rainforest. J. Nat. Prod., 65, 1222–1224 (2002).

    PubMed  Article  CAS  Google Scholar 

  2. Chen, C. Y., Chang, F. R., and Wu, Y. C., The constituents from the stem of Annona cherimola. J. Chin. Chem. Soc., 44, 313–319 (1997).

    CAS  Google Scholar 

  3. Chen, C. Y., Chang, F. R., Teng, C. M., and Wu, Y. C., Cheritamine, a new N-fatty acyl tryptamine and other constituents from the stems of Annona cherimola. J. Chin. Chem. Soc., 46, 77–86 (1999).

    CAS  Google Scholar 

  4. Chen, Y. H., Chang, F. R., Lu, M. C., Hsieh, P. W., Wu, M. J., Du, Y. C., and Wu, Y. C., New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis Burm. Molecules, 13, 255–266 (2008).

    PubMed  Article  CAS  Google Scholar 

  5. Chiang, Y. M., Liu, H. K., Lo, J. M., Chien, S. C., Chan, Y. F., Lee, T. H., Su, J. K., and Kuo, Y. H., Cytotoxic constituents of the leaves Calocedrus formosana. J. Chin. Chem. Soc., 50, 161–166 (2003).

    CAS  Google Scholar 

  6. Choi, D. Y., Lee, J. Y., Kim, M. R., Woo, E. R., Kim, Y. G., and Kang, K. W., Chrysoeriol potently inhibits the induction of nitric oxide synthase by blocking AP-1 activation. J. Biomed. Sci., 12, 949–959 (2005).

    PubMed  Article  CAS  Google Scholar 

  7. Felpin, F.-X. and Lebreton, J., History, chemistry and biology of alkaloids from Lobelia inflata. Tetrahedron, 60, 10127–10153 (2004).

    CAS  Google Scholar 

  8. Hiermann, A., Kedwani, S., Schramm, H. W., and Seger, C., A new pyrrole alkaloid from seeds of Castanea sativa. Fitoterapia, 73, 22–27 (2002).

    PubMed  Article  CAS  Google Scholar 

  9. Hu, H. B., Jian, Y. F., Cao, H., and Zheng, X. D., Phenolic compounds from Elsholtzia bodinieri Van’t. J. Chin. Chem. Soc., 54, 1189–1194 (2007).

    CAS  Google Scholar 

  10. Huang, X. and Liu, Z., Solid-phase synthesis of 4(1H)-quinolone and pyrimidine derivatives based on a new scaffold-polymer-bound cyclic malonic acid ester. J. Org. Chem., 67, 6731–6737 (2002).

    PubMed  Article  CAS  Google Scholar 

  11. Hwang, T. L., Li, G. L., Lan, Y. H., Chia, Y. C., Hsieh, P. W., Wu, Y. H., and Wu, Y. C., Potent inhibition of superoxide anion production in activated human neutrophils by isopedicin, a bioactive component of the Chinese medicinal herb Fissistigma oldhamii. Free Radic. Biol. Med., 46, 520–528 (2009).

    PubMed  Article  CAS  Google Scholar 

  12. Ishimaru, K., Yonemitsu, H., and Shimomura, K., Lobetyolin and lobetyol from hairy root culture of Lobelia inflata. Phytochemistry, 30, 2255–2257 (1991).

    Article  CAS  Google Scholar 

  13. Ishimaru, K., Sadoshima, S., Neera, S., Koyama, K., Takahashi, K., and Shimomura, K., A polyacetylene gentiobioside from hairy roots of Lobelia inflata. Phytochemistry, 31, 1577–1579 (1992).

    Article  CAS  Google Scholar 

  14. Jang, S. I., Kim, Y. J., Lee, W. Y., Kwak, K. C., Baek, S. H., Kwak, G. B., Yun, Y. G., Kwon, T. O., Chung, H. T., and Chai, K. Y., Scoparone from Artemisia capillaris inhibits the release of inflammatory mediators in RAW 264.7 cells upon stimulation cells by interferon-γ plus LPS. Arch. Pharm. Res., 28, 203–208 (2005).

    PubMed  Article  CAS  Google Scholar 

  15. Kang, J., Choi, M. Y., Kang, S., Kwon, H. N., Wen, H., Lee, C. H., Park, M., Wiklund, S., Kim, H. J., Kwon, S. W., and Park, S., Application of a 1H nuclear magnetic resonance (NMR) metabolomics approach combined with orthogonal projections to latent structure-discriminant analysis as an efficient tool for discriminating between Korean and Chinese herbal medicines. J. Agric. Food Chem., 56, 11589–11595 (2008).

    PubMed  Article  CAS  Google Scholar 

  16. Kawaii, S., Tomono, Y., Katase, E., Ogawa, K., and Yano, M., Isolation of furocoumarins from Bergamot fruits as HL-60 differentiation-inducing compounds. J. Agric. Food Chem., 47, 4073–4078 (1999).

    PubMed  Article  CAS  Google Scholar 

  17. Kiuchi, F., Suzuki, N., Fukumoto, Y., Goto, Y., Mitsui, M., and Tsuda, Y., Chemical transformation of embelin through dimerization during preparation of a decoction. Chem. Pharm. Bull., 46, 1225–1228 (1998).

    CAS  Google Scholar 

  18. Koukoulitsa, C., Karioti, A., Bergonzi, M.C., Pescitelli, G., Di Bari, L., and Skaltsa, H., Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece. J. Agric. Food Chem., 54, 5388–5392 (2006).

    PubMed  Article  CAS  Google Scholar 

  19. Kowalska, I., Stochmal, A., Kapusta, I., Janda, B., Pizza, C., Piacente, S., and Oleszek, W., Flavonoids from barrel medic (Medicago truncatula) aerial parts. J. Agric. Food Chem., 55, 2645–2652 (2007).

    PubMed  Article  CAS  Google Scholar 

  20. Kuo, Y. C., Chen, C. C., Tsai, W. J., and Ho, Y. H., Regulation of herpes simplex virus type 1 replication in Vero cells by Psychotria serpens: relationship to gene expression, DNA replication, and protein synthesis. Antiviral Res., 51, 95–109 (2001).

    PubMed  Article  CAS  Google Scholar 

  21. Kuo, Y. C., Kuo, Y. H., Lin, Y. L., and Tsai, W. J., Yatein from Chamaecyparis obtuse suppresses herpes simplex virus type 1 replication in HeLa cells by interruption the immediate-early gene expression. Antiviral Res., 70, 112–120 (2006).

    PubMed  Article  CAS  Google Scholar 

  22. Kuo, Y. C., Lee, Y. C., Leu, Y. L., Tsai, W. J., and Chang, S. C., Efficacy of orally administered Lobelia chinensis extracts on herpes simplex virus type 1 infection in BALB/c mice. Antiviral Res., 80, 206–212 (2008).

    PubMed  Article  CAS  Google Scholar 

  23. Lai, C.-S., Mas, R. H. M. H., Nair, N. K., Mansor, S. M., and Navaratnam, V., Chemical constituents and in vitro anticancer activity of Typhonium flagelliforme (Araceae). J. Ethnopharmacol., 127, 486–494 (2010).

    PubMed  Article  CAS  Google Scholar 

  24. Lee, C. K. and Chang, M. H., The chemical constituents from the heartwood of Eucalyptus citriodora. J. Chin. Chem. Soc., 47, 555–560 (2000).

    CAS  Google Scholar 

  25. Lee, T. H., Chiou, J. L., Lee, C. K., and Kuo, Y. H., Separation and determination of chemical constituents in the roots of Rhus javanica L. var. roxburghiana. J. Chin. Chem. Soc., 52, 833–841 (2005).

    CAS  Google Scholar 

  26. Monrad, R. N. and Madsen, R., Rhodium-catalyzed decarbonylation of aldoses. J. Org. Chem., 72, 9782–9785 (2007).

    PubMed  Article  Google Scholar 

  27. Nagao, T., Abe, F., Kinjo, J., and Okabe, H., Antiproliferative constituents in plants 10. Flavones from the leaves of Lantana montevidensis Briq. and consideration of structure-activity relationship. Biol. Pharm. Bull., 25, 875–879 (2002).

    PubMed  Article  CAS  Google Scholar 

  28. Nishina, A., Hasegawa, K., Uchibori, T., Seino, H., and Osawa, T., 2,6-Dimethoxy-p-benzoquinone as an antibacterial substance in the bark of Phyllostachys heterocycla var. Pubescens, a species of thick-stemmed bamboo. J. Agric. Food Chem., 39, 266–269 (1991).

    Article  CAS  Google Scholar 

  29. Nord, L. I., Vaag, P., and Duus, J. Ø., Quantification of organic and amino acids in beer by 1H NMR spectroscopy. Anal. Chem., 76, 4790–4798 (2004).

    PubMed  Article  CAS  Google Scholar 

  30. Ouwerkerk, N., Steenweg, M., de Ruijter, M., Brouwer, J., van Boom, J. H., Lugtenburg, J., and Raap, J., One-pot two-step enzymatic coupling of pyrimidine bases to 2-deoxy-D-ribose-5-phosphate. A new strategy in the synthesis of stable isotope labeled deoxynucleosides. J. Org. Chem., 67, 1480–1489 (2002).

    PubMed  Article  CAS  Google Scholar 

  31. Park, B. Y., Min, B. S., Oh, S. R., Kim, J. H., Bae, K. H., and Lee, H. K., Isolation of flavonoids, a biscoumarin and an amide from the flower buds of Daphne genkwa and the evaluation of their anti-complement activity. Phytother. Res., 20, 610–613 (2006).

    PubMed  Article  CAS  Google Scholar 

  32. Quintin, J. and Lewin, G., Semisynthesis of linarin, acacetin, and 6-iodoapigenin derivatives from diosmin. J. Nat. Prod., 67, 1624–1627 (2004).

    PubMed  Article  CAS  Google Scholar 

  33. Sahu, N. P., Achari, B., and Banerjee, S., 7,3-Dihydroxy-4’-methoxyflavone from seeds of Acacia farnesiana. Phytochemistry, 49, 1425–1426 (1998).

    Article  CAS  Google Scholar 

  34. Shibano, M., Tsukamoto, D., Masuda, A., Tanaka, Y., and Kusano, G., Two new pyrrolidine alkaloids, radicamines A and B, as inhibitors of α-glucosidase from Lobelia chinensis Lour. Chem. Pharm. Bull., 49, 1362–1365 (2001).

    PubMed  Article  CAS  Google Scholar 

  35. Shibano, M., Fujimoto, Y., Kushino, K., Kusano, G., and Baba, K., Biosynthesis of 1-deoxynojirimycin in Commelina communis: a difference between the microorganisms and plants. Phytochemistry, 65, 2661–2665 (2004).

    PubMed  Article  CAS  Google Scholar 

  36. Stochmal, A., Piacente, S., Pizza, C., De Riccardis, F., Leitz, R., and Oleszek, W., Alfalfa (Medicago sativa L.) flavonoids. 1. Apigenin and luteolin glycosides from aerial parts. J. Agric. Food Chem., 49, 753–758 (2001).

    PubMed  Article  CAS  Google Scholar 

  37. Takahashi, H., Kittaka, H., and Ikegami, S., Novel synthesis of enantiomerically pure matural inositols and their diastereoisomers. J. Org. Chem., 66, 2705–2716 (2001).

    PubMed  Article  CAS  Google Scholar 

  38. Wang, H., Tian, X., and Chen, Y. Z., Chemical constituents of the aerial part of Celastrus hypoleucus. J. Chin. Chem. Soc., 49, 433–436 (2002).

    CAS  Google Scholar 

  39. Wu, T. S., Chang, F. C., Wu, P. L., Kuoh, C. S., and Chen, I. S., Constituents of leaves of Tetradium glabriflium. J. Chin. Chem. Soc., 42, 929–934 (1995).

    CAS  Google Scholar 

  40. Wu, T. S., Leu, Y. L., and Chan, Y. Y., Aristolochic acid as a defensive substance for the aristolochiaceous plantfeeding swallowtail butterfly, Pachliopta aristolochiae interpositus. J. Chin. Chem. Soc., 47, 221–226 (2000).

    CAS  Google Scholar 

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Correspondence to Yann-Lii Leu.

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Kuo, PC., Hwang, TL., Lin, YT. et al. Chemical constituents from Lobelia chinensis and their anti-virus and anti-inflammatory bioactivities. Arch. Pharm. Res. 34, 715 (2011). https://doi.org/10.1007/s12272-011-0503-7

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Key words

  • Lobelia chinensis
  • Lobechine
  • Superoxide anion generation
  • Elastase release