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Biological Evaluation of Terrestrial and Marine Plant Originated Labdane Diterpenes (A Review)

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Pharmaceutical Chemistry Journal Aims and scope

Recent progress on studies of labdane diterpenoids is compiled. Seventy seven biologically active labdane diterpenes isolated from various higher plants, mosses, liverworts, algae, etc. are reported. The absolute configurations of compounds 1 – 77 were established using extensive spectroscopic techniques. The wide range of biological activities possessed by these diterpenoids suggests that thorough evaluation of some structure-activity relationships is overdue. In this review, data on the natural sources, isolation, structure and biological activities of labdane diterpenoids isolated from various plants are summarized.

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References

  1. B. De las Heras, S. Hortelano, N. Giron, et al., J. Pharmacol., 152, 249 – 255 (2007).

  2. A. Castrillo, B. De las Heras, S. Hortelano, and B. Rodriguez, J. Biol. Chem., 276, 15854 – 15860 (2001).

  3. B. De las Heras and S. Hortelano. Inflamm. Allergy Drug Targets 8, 28 – 39 (2009).

  4. N. Gurusamy, I. Lekli, S. Mukherjee, D. Ray, et al., Cardiovasc. Res., 86, 103 – 112 (2010).

    Article  CAS  PubMed  Google Scholar 

  5. J. D. Cocker, T. G. Halsall, and A. Bowers. J. Chem. Soc., Issue 0, 4259 – 4262 (1956).

  6. J. D. Cocker and T. G. Halsall. J. Chem. Soc., Issue 0, 4262 – 4271 (1956).

  7. M. P. Gupta, 270 Iberoamerican Medicinal Plants, Andres Bello Convention Edition, Bogota, Colombia (1995), pp. 73 – 84.

  8. H. Soicke and E. Leng-Peschlow. Planta Medica, 53, 37 – 39 (1987).

    Article  CAS  PubMed  Google Scholar 

  9. B. B. Jarvis, S. Wang, C. Cox, et al., Natural Toxins, 4, 58 – 71 (1996).

    Article  CAS  PubMed  Google Scholar 

  10. I. Rizzo, E. Varsavky, M. Haidukowski, and H. Frade, Toxicon 35, 753 – 757 (1997).

    Article  CAS  PubMed  Google Scholar 

  11. G. E. Feresin, A. Tapia, S. N. Lopez, and S. A. Zacchino, J. Ethnopharmacol., 78, 103 – 107 (2001)

    Article  CAS  PubMed  Google Scholar 

  12. K. Chakraborty, A. P. Lipton, R. Paul, et al., Food Chem., 119, 1399 – 1408 (2010).

    Article  CAS  Google Scholar 

  13. U. Hawas, S. Eltomy, R. Nassif, et al., Natur. Prod. Res. (2013).

  14. R. R. Kulkarni, K. Shurpali, V. G. Puranic, et al., J. Natur. Prod., 76, 1836 – 1841 (2013).

    Article  CAS  Google Scholar 

  15. S. Ghosh, K. Indukari, S. Bondalapati, et al., Eur. J. Med. Chem., 66, 101 – 105 (2013).

    Article  CAS  PubMed  Google Scholar 

  16. D. S. A. Cassiano, A. G. M. Pacheco, et al., Natur. Prod. Res. (2013).

  17. D. da Silva, L. Luiza, N. M. Silva, et al., J. natur. Prod., 71, 1291 – 1293 (2008).

  18. M. Z. Sultan, Y. M. Jeon, S. S. Moon. Planta medica 74, 449 – 452 (2008).

  19. P. Waridel, J. L. Wolfender, and J. B. Lachavanne, Phytochemistry 64, 1309 – 1317 (2003).

    Article  CAS  PubMed  Google Scholar 

  20. Environment Canada Biological Test Methods, Growth Inhibition Test Using the Fresh Water Alga Selenastrum capricornutum. Environmental Protection Series: 1 / RM / 25 (1992).

  21. F. T. M. Creasel, Algaltoxkit: Freswater Toxicity Test with Microalgae. Standard Operational Procedure, Deinze, Belgium (1996).

  22. P. Waridel, J. L. Wolfender, J. B. Lachavanne, and K. Hostettmann. Phytochemistry, 65, 945 – 954 (2004).

    Article  CAS  PubMed  Google Scholar 

  23. T. Cangiano, M. DellaGreca, A. Fiorentino, et al., J. Chem. Ecol., 28, 1091 – 1102 (2000).

    Article  Google Scholar 

  24. C. J. Zheng, B. K. Huang, Y. Wang, et al., Bioorg. Med. Chem., 18, 175 – 181 (2010).

    Article  CAS  PubMed  Google Scholar 

  25. T. H. Kim, H. Li, Q. Wua, H. J. Lee, et al., J. Ethnopharmacol., 146, 760 – 767 (2013).

    Article  CAS  PubMed  Google Scholar 

  26. S. Khan, O. Shehzad, H. G. Jin, et al., J. Natur. Prod., 75, 67 – 71 (2012).

    Article  CAS  Google Scholar 

  27. S. A. Rao, B. Rajanikanth, and R. Seshadri, J. Agric. Food Chem., 37, 740 – 743 (1989).

    Article  CAS  Google Scholar 

  28. S. G. Achut, and C. Bandyopadhyaya, J. Agric. Food Chem., 32, 57 – 59 (1984).

  29. S. Singh, R. Singh, S. Banerjee, et al., Food Chemistry 131, 375 – 379 (2012).

    Article  CAS  Google Scholar 

  30. K. Awang, N. H. Abdullah, A. Hamid, et al., J. Biomed. Biotechnol., 876458 (2012).

  31. The Wealth of India, C. S. I. R, New Delhi, 5:13 (1959).

  32. T. Mosmann. J. Immunol. Meth., 65, 55–63 (1983).

    Article  CAS  Google Scholar 

  33. P. P. Reddy, R. R. Rao, J. Shashidhar, et al., Bioorg. Med. Chem. Lett., 19, 6078 – 6081 (2009).

    Article  CAS  PubMed  Google Scholar 

  34. S. Block, C. Stevigny, P. G. De, et al., Planta Medica, 68, 647 – 649 (2002).

    Article  CAS  PubMed  Google Scholar 

  35. S. Block, C. Baccelli, B. Tinant, et al., J. Quetin-Leclercq, 65, 1165 – 1171 (2004).

    CAS  Google Scholar 

  36. X. H. Cai, X. D. Luo, J. Zhou, and X. J. Hao. Helv. Chim. Acta, 88, 2938 – 2943 (2005).

    Article  CAS  Google Scholar 

  37. X. H. Cai, Y. Y. Wang, P. J. Zhao, et al., Phytochemistry, 71, 1020 – 1024 (2010).

    Article  CAS  PubMed  Google Scholar 

  38. Y. Asakawa, Phytochemistry, 65, 623 – 669 (2004).

    Article  CAS  PubMed  Google Scholar 

  39. Y. Asakawa, Pure Appl. Chem., 79, 557 – 580 (2007).

    Article  CAS  Google Scholar 

  40. . Y. Q. Shi, X. J. Qu, Y. X. Liao, et al., Eur. J. Pharmacol., 584, 66 – 71 (2008).

    Article  CAS  PubMed  Google Scholar 

  41. Y. Asakawa, M. Toyota, M. von Konrat, and J. E. Braggins, Phytochemistry, 62, 439 – 452 (2003).

    Article  CAS  PubMed  Google Scholar 

  42. C. Chaichantipyuth, A. Petsom, P. Taweechotipatr, et al., Heterocycles, 65, 809 – 822 (2005).

    Article  CAS  Google Scholar 

  43. X. A. Dominguez, C. Cisneros, T. E. Guajardo, et al., Phytochemistry, 14, 1665 – 1666 (1975)

    Article  CAS  Google Scholar 

  44. D. F. Zinkel andW. B. Clarke, Phytochemistry, 24, 1267 – 1271 (1985).

  45. D. X. Guo, F. Xiang, X. N. Wang, et al., Phytochemistry, 71, 1573 – 1578 (2010).

    Article  CAS  PubMed  Google Scholar 

  46. N. Miyoshi, Y. Nakamura, Y. Ueda, et al., Cancer Lett., 199, 113 – 119 (2003).

    Article  CAS  PubMed  Google Scholar 

  47. S. K. Chen, H. Li, P. Y. Chen, in Chinese Flora (Zhongguo Zhiwu Zhi), Science Press, Beijing (1997), Vol. 7, pp. 30 – 31.

  48. Y. Li, T. T. Wang, J. Zhao, et al., Food Chem., 131, 972 – 976 (2012).

    Article  CAS  Google Scholar 

  49. C. Demetzos, C. Harvala, S. Philianos, and A. L. Skaltsounis, J. Natur. Prod., 53, 1365 – 1368 (1990).

  50. C. Demetzos, B. Stahl, T. Anastassaki, et al., Planta Medica, 65, 76 – 78 (1999).

    Article  CAS  PubMed  Google Scholar 

  51. K. Dimas, D. Kokkinopoulos, C. Demetzos, et al., Leuk. Res., 23, 217 – 234 (1999).

    Article  CAS  PubMed  Google Scholar 

  52. K. Dimas, M. Papadaki, C. Tsimplouli, et al., Biomed. Pharmacother., 60, 127 – 133 (2006).

    Article  CAS  PubMed  Google Scholar 

  53. K. Dimas, C. Demetzos, P. Ioannidis, and T. Trangas, Leuk. Res., 25, 449 – 454 (2001).

    Article  CAS  PubMed  Google Scholar 

  54. R. Hegnauer, Chemotaxonomy of Plants, Birkhauser Verlag, Basel–Stuttgart (1964), Vol. 3, p. 108.

  55. E. Gunther, The Essential Oils, Van Nostrand, New York (1950), Vol. 4, pp. 45 – 52.

  56. D. J. Newman, G. M. Cragg, and K. M. Snader, J. Natur. Prod., 66, 1022 – 1037 (2003).

  57. C. Demetzos, S. Mitakou, M. Couladis, et al., Planta Medica, 60, 590 – 591 (1994).

    Article  CAS  PubMed  Google Scholar 

  58. I. Chinou, C. Demetzos, C. Harvala, et al., Planta Medica, 60, 34 – 36 (1994).

    Article  CAS  PubMed  Google Scholar 

  59. C. Matsingou, K. Dimas, and C. Demetzos. Biomed. Pharmacother., 60, 191 – 199 (2006).

    Article  CAS  PubMed  Google Scholar 

  60. P. Zhang, W. Huang, Z. Song, et al., Phytochem. Lett., 1, 103 – 106 (2008).

    Article  CAS  Google Scholar 

  61. N. Chimnoi, C. Sarasuk, N. Khunnawutmanotham, et al., Phytochem. Lett., 2, 184 – 187 (2009).

    Article  CAS  Google Scholar 

  62. M. T. Akam, P. Tane, H. K. Wabo, et al., J. Natur. Prod. Commun., 1, 449 – 452 (2006).

    CAS  Google Scholar 

  63. S. Saeidina, A. R. Gohari, A. R. Shahverdi, et al., Pharm. Res, 1, 428 – 430 (2009).

    Google Scholar 

  64. V. T. Sielinou, J. C. Vardamide, and A. E. Nkengfack,. Phytochem. Lett., 5, 409 – 413 (2012).

    Article  CAS  Google Scholar 

  65. C. L. Zani, T. M. Alves, R. Queiroz, et al., Phytochemistry, 53, 877 – 880 (2000).

    Article  CAS  PubMed  Google Scholar 

  66. E. M. Souza-Fagundes, A. B. Queiroz, O. A. Martins Filho, et al., Mem. Inst. Oswaldo Cruz, 97, 1207 – 1212 (2002).

    Article  PubMed  Google Scholar 

  67. E. M. Souza-Fagundes, G. Gazzinelli, G. G. Parreira, et al., Int. J. Immunopharmacol., 3, 383 – 392 (2003).

    Article  CAS  Google Scholar 

  68. E. Scio, A. Ribeiro, M. A. A. Tania, et al., Phytochemistry, 64, 1125 – 1131 (2003).

    Article  CAS  PubMed  Google Scholar 

  69. R. Q. Licea, R. M. Castillo, R. G. Flores, et al., Molecules, 17, 11229 – 11241 (2012).

    Article  Google Scholar 

  70. L. S. Ok, C. S. Zin, C. S. Un,, et al., J. Natur. Prod., 68, 1471 – 1474 (2005).

    Article  Google Scholar 

  71. L.W. Xin, C. C. Bin, and C. Bing, J. Asian Natur. Prod. Res., 7, 95 – 105 (2005).

  72. A. W. W. Vanwyk, C. A. Gray, C. E. Whibley, et al., J. Natur. Prod., 71 , 420 – 425 (2008).

    Article  CAS  Google Scholar 

  73. S. S. Valere, T. Pierre, N. Bonaventure, et al., Tetrahedron, 63, 8993 – 8998 (2007).

    Article  Google Scholar 

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Authors and Affiliations

  1. Phytochemistry Division, CSIR-National Botanical Research Institute, Lucknow, U. P., 226001, India

    Mahesh Pal, Tripti Mishra, Anil Kumar & Shri Krishana Tewari

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  1. Mahesh Pal
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  2. Tripti Mishra
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Correspondence to Mahesh Pal.

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Pal, M., Mishra, T., Kumar, A. et al. Biological Evaluation of Terrestrial and Marine Plant Originated Labdane Diterpenes (A Review). Pharm Chem J 50, 558–567 (2016). https://doi.org/10.1007/s11094-016-1490-2

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  • DOI: https://doi.org/10.1007/s11094-016-1490-2

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