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Cembranoids of Soft Corals: Recent Updates and Their Biological Activities |
Marsya Yonna Nurrachma, Deamon Sakaraga, Ahmad Yogi Nugraha, Siti Irma Rahmawati, Asep Bayu, Linda Sukmarini, Akhirta Atikana, Anggia Prasetyoputri, Fauzia Izzati, Mega Ferdina Warsito, Masteria Yunovilsa Putra |
Research Center for Biotechnology, Indonesian Institute of Sciences(LIPI), Jalan Raya Jakarta-Bogor KM. 46, Cibinong, Bogor, West Java, Indonesia |
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Abstract Soft corals are well-known as excellent sources of marine-derived natural products. Among them, members of the genera Sarcophyton, Sinularia, and Lobophytum are especially attractive targets for marine natural product research. In this review, we reported the marine-derived natural products called cembranoids isolated from soft corals, including the genera Sarcophyton, Sinularia, and Lobophytum. Here, we reviewed 72 reports published between 2016 and 2020, comprising 360 compounds, of which 260 are new compounds and 100 are previously known compounds with newly recognized activities. The novelty of the organic molecules and their relevant biological activities, delivered by the year of publication, are presented. Among the genera presented in this report, Sarcophyton spp. produce the most cembranoid diterpenes; thus, they are considered as the most important soft corals for marine natural product research. Cembranoids display diverse biological activities, including anti-cancer, anti-bacterial, and anti-inflammatory. As cembranoids have been credited with a broad range of biological activities, they present a huge potential for the development of various drugs with potential health and ecological benefits.
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Keywords
Cembranoids
Diterpene
Soft corals
Sarcophyton
Sinularia
Lobophytum
Anti-bacterial
Anti-cancer
Anti-inflammatory
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Corresponding Authors:
Asep Bayu, Masteria Yunovilsa Putra
E-mail: asepbayu@yahoo.co.id,asep046@lipi.go.id;mast001@lipi.go.id,masteria.yunovilsa@gmail.com
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Issue Date: 04 June 2021
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1. M. Townsend, K. Davies, N. Hanley, J.E. Hewitt, C.J. Lundquist, A.M. Lohrer, Front. Mar. Sci. 5, 359 (2018) 2. H. Malve, J. Pharm. Bioall. Sci. 8, 83 (2016) 3. E. O. Wilson and F. Peter M., Biodiversity (National Academies Press, Washington, D.C., 1988), p. 989. 4. D. Zeppilli, D. Leduc, C. Fontanier, D. Fontaneto, S. Fuchs, A.J. Gooday, A. Goineau, J. Ingels, V.N. Ivanenko, R.M. Kristensen, R.C. Neves, N. Sanchez, R. Sandulli, J. Sarrazin, M.V. Sørensen, A. Tasiemski, A. Vanreusel, M. Autret, L. Bourdonnay, M. Claireaux, V. Coquillé, L. De Wever, D. Rachel, J. Marchant, L. Toomey, D. Fernandes, Mar. Biodiv. 48, 35 (2018) 5. O.K. Radjasa, Y.M. Vaske, G. Navarro, H.C. Vervoort, K. Tenney, R.G. Linington, P. Crews, Bioorg. Med. Chem. 19, 6658 (2011) 6. S. Aratake, T. Tomura, S. Saitoh, R. Yokokura, Y. Kawanishi, R. Shinjo, J.D. Reimer, J. Tanaka, H. Maekawa, PLoS ONE 7, e30410 (2012) 7. Y. Li, G. Pattenden, Nat. Prod. Rep. 28, 1269 (2011) 8. M.T.R. Almeida, M.I.G. Moritz, K.C.C. Capel, C.D. Pérez, E.P. Schenkel, Rev. Bras 24, 446 (2014) 9. Y. González, D. Torres-Mendoza, G.E. Jones, P.L. Fernandez, Mediators Inflamm. 2015, 1 (2015) 10. E. Fattorusso, P. Luciano, M.Y. Putra, O. Taglialatela-Scafati, A. Ianaro, E. Panza, G. Bavestrello, C. Cerrano, Tetrahedron 67, 7983 (2011) 11. K.H. Lai, W.J. You, C.C. Lin, M. El-Shazly, Z.J. Liao, J.H. Su, Mar. Drugs 15, 327 (2017) 12. D. Rodríguez, Y. Li, H. Dhasmana, C.L. Barnes, J. Nat. Prod. 56, 1101 (1993) 13. M. Gill, W. Steglich, Fortschritte Der Chemie Organischer Naturstoffe/Progress in the Chemistry of Organic Natural Products (Springer, Vienna, 1987). 14. Z. Xi, W. Bie, W. Chen, D. Liu, L. Ofwegen, P. Proksch, W. Lin, Mar. Drugs 11, 3186 (2013) 15. B. Yang, X.-F. Zhou, X.-P. Lin, J. Liu, Y. Peng, X.-W. Yang, Y. Liu, Curr. Org. Chem. 16, 1512 (2012) 16. J.W. Blunt, B.R. Copp, M.H.G. Munro, P.T. Northcote, M.R. Prinsep, Nat. Prod. Rep. 28, 196 (2011) 17. T. Kamada, C.S. Phan, H.S. Tin, C.S. Vairappan, T.S.T. Muhammad, Nat. Prod. Commun. 11, 1077 (2016) 18. M.Y. Putra, A. Saparhadi, F. Karim, T. Murniasih, R.T. Swasono, Squalen Bull. Mar. Fish. Postharvest Biotechnol. 11, 53 (2016) 19. P. Sun, Q. Yu, J. Li, R. Riccio, G. Lauro, G. Bifulco, T. Kurtán, A. Mándi, H. Tang, T.J. Li, C.L. Zhuang, W.H. Gerwick, W. Zhang, J. Nat. Prod. 79, 2552 (2016) 20. W.T. Chen, L.F. Liang, X.W. Li, W. Xiao, Y.W. Guo, Nat. Prod. Bioprospect. 6, 97 (2016) 21. M. Zubair, W. Alarif, K. Al-Footy, M. Ph, M. Ali, S. Basaif, S. Al-Lihaibi, S.-E. Ayyad, Turk. J. Chem. 40, 385 (2016) 22. G.H. Tang, Z.H. Sun, Y.H. Zou, S. Yin, Molecules 21, 587 (2016) 23. M. Shaaban, M.A. Ghani, K.A. Shaaban, J. Chem. Sci. 71, 1211 (2016) 24. W. Li, Y.H. Zou, M.X. Ge, L.L. Lou, Y.S. Xu, A. Ahmed, Y.Y. Chen, J.S. Zhang, G.H. Tang, S. Yin, Mar. Drugs 15, 85 (2017) 25. M.E.F. Hegazy, A.I. Elshamy, T.A. Mohamed, A.R. Hamed, M.A.A. Ibrahim, S. Ohta, P.W. Paré, Mar. Drugs 15, 192 (2017) 26. M. Shaaban, A.M. El-Hagrassi, M.A. Abdelghani, A.F. Osman, J. Biosci. 73, 325 (2017) 27. M.P. Rahelivao, T. Lübken, M. Gruner, O. Kataeva, R. Ralambondrahety, H. Andriamanantoanina, M.P. Checinski, I. Bauer, H.J. Knölker, Org. Biomol. Chem. 15, 2593 (2017) 28. L.F. Liang, W.T. Chen, X.W. Li, H.Y. Wang, Y.W. Guo, Sci. Rep. 7, 1 (2017) 29. H. Januar, N. Zamani, D. Soedharma, E. Chasanah, Pharmacognosy Research 9, 65 (2017) 30. L.F. Liang, W.T. Chen, E. Mollo, L.G. Yao, H.Y. Wang, W. Xiao, Y.W. Guo, Chem. Biodivers. 14, e1700079 (2017) 31. S. Li, F. Ye, Z. Zhu, H. Huang, S. Mao, Y. Guo, Acta Pharm. Sin. B 8, 944 (2018) 32. H. M. Hassan, M. E. Rateb, M. H. Hassan, A. M. Sayed, S. Shabana, M. Raslan, E. Amin, F. A. Behery, O. M. Ahmed, A. B. Muhsinah, T. A. M. Gulder, U. R. Abdelmohsen, Mar. Drugs 17, (2019). 33. Y.W. Ahmed, C.Y. Chen, Y.J. Huang, C.C. Tseng, C.F. Lin, YCWu Dai, J.H. Sheu, Mar. Drugs 16, 210 (2018) 34. C.C. Peng, C.Y. Huang, A.F. Ahmed, T.L. Hwang, C.F. Dai, J.H. Sheu, Mar. Drugs 16, 276 (2018) 35. M. Shaaban, M.Y. Issa, M.A. Ghani, A. Hamed, A.B. Abdelwahab, Nat. Prod. Res. 33, 24 (2019) 36. L.F. Liang, T. Kurtán, A. Mándi, L.G. Yao, J. Li, L.F. Lan, Y.W. Guo, Tetrahedron 74, 1933 (2018) 37. K. Tani, T. Kamada, C.-S. Phan, and C. S. Vairappan, Nat Product Commun. 14, 1934578X1986837 (2019). 38. P. Sun, F.Y. Cai, G. Lauro, H. Tang, L. Su, H.L. Wang, H.H. Li, A. Mándi, T. Kurtán, R. Riccio, G. Bifulco, W. Zhang, J. Nat. Prod. 82, 1264 (2019) 39. G. Li, H. Li, Q. Zhang, M. Yang, Y.C. Gu, L.F. Liang, W. Tang, Y.W. Guo, J. Org. Chem. 84, 5091 (2019) 40. M.E.F. Hegazy, T.A. Mohamed, A.I. Elshamy, A.R. Hamed, M.A.A. Ibrahim, S. Ohta, A. Umeyama, P.W. Paré, T. Efferth, RSC Adv. 9, 27183 (2019) 41. J. Zhang, X. Tang, X. Han, D. Feng, X. Luo, L. Van Ofwegen, P. Li, G. Li, Inorg. Chem. Front. 6, 2004 (2019) 42. M. Yang, X.L. Li, J.R. Wang, X. Lei, W. Tang, X.W. Li, H. Sun, Y.W. Guo, J. Org. Chem. 84, 2568 (2019) 43. G. Li, H. Li, W. Tang, L.G. Yao, L.F. Liang, Y.W. Guo, Bioorg. Chem. 101, 103993 (2020) 44. H.A. Saleh, K.M. Raafat, T.A. Temraz, N. Noureldin, H.G. Breitinger, U. Breitinger, Neurotoxicology 80, 105 (2020) 45. T.Y. Huang, C.Y. Huang, C.H. Chao, C.C. Lin, C.F. Dai, J.H. Su, P.J. Sung, S.H. Wu, J.H. Sheu, Mar. Drugs 18, 452 (2020) 46. T.Y. Huang, C.Y. Huang, S.R. Chen, J.R. Weng, T.H. Tu, Y.B. Cheng, S.H. Wu, J.H. Sheu, Mar. Drugs 19, 8 (2020) 47. M. M. A. Ahmed, M. A. Albadry, E. A. Ragab, E. M. El-Ghaly, S. K. Ismail, Z. Ali, S. I. Khan, A. G. Chittiboyina, and I. A. Khan, Nat. Product Res. 1 (2020). 48. C.C. Peng, C.Y. Huang, A.F. Ahmed, T.L. Hwang, J.H. Sheu, Mar. Drugs 18, 573 (2020) 49. C.Y. Huang, Y.J. Tseng, U. Chokkalingam, T.L. Hwang, C.H. Hsu, C.F. Dai, P.J. Sung, J.H. Sheu, J. Nat. Prod. 79, 1339 (2016) 50. M.P. Rahelivao, M. Gruner, T. Lübken, D. Islamov, O. Kataeva, H. Andriamanantoanina, I. Bauer, H.-J. Knölker, Org. Biomol. Chem. 14, 989 (2016) 51. C.H. Chao, C.Y. Wu, C.Y. Huang, H.C. Wang, C.F. Dai, Y.C. Wu, J.H. Sheu, Mar. Drugs 14, 150 (2016) 52. M. Yang, H. Li, Q. Zhang, Q.-H. Wu, G. Li, K.-X. Chen, Y.-W. Guo, W. Tang, X.-W. Li, Bioorg. Med. Chem. 27, 3469 (2019) 53. M. Wang, J. Jin, L. Li, F. Cao, C. Wang, C.-Y. Wang, Chem. Nat. Compd. 53, 181 (2017) 54. G.F. Qin, X.L. Tang, Y.T. Sun, X.C. Luo, J. Zhang, L. van Ofwegen, P.J. Sung, P.L. Li, G.Q. Li, Mar. Drugs 16, 127 (2018) 55. T.C. Tsai, K.H. Lai, J.H. Su, Y.J. Wu, J.H. Sheu, Mar. Drugs 16, 104 (2018) 56. T. Kamada, M.C. Kang, C.S. Phan, I. Zanil, Y.J. Jeon, C. Vairappan, Mar. Drugs 16, 99 (2018) 57. C.H. Wu, C.H. Chao, T.Z. Huang, C.Y. Huang, T.L. Hwang, C.F. Dai, J.H. Sheu, Mar. Drugs 16, 278 (2018) 58. Q. Wu, X.W. Li, H. Li, L.G. Yao, W. Tang, Z.H. Miao, H. Wang, Y.W. Guo, Bioorg. Med. Chem. Lett. 29, 185 (2019) 59. C.I. Yu, C.Y. Chen, W. Liu, P.C. Chang, C.W. Huang, K.F. Han, I.P. Lin, M.Y. Lin, C.H. Lee, Mar. Drugs 16, 387 (2018) 60. C.S. Jiang, T. Ru, L.G. Yao, Z.H. Miao, Y.W. Guo, Fitoterapia 136, 104176 (2019) 61. M.J. Wu, H. Wang, C.S. Jiang, Y.W. Guo, Bioorg. Chem. 104, 104281 (2020) 62. L.L. Sun, W.S. Li, J. Li, H.Y. Zhang, L.G. Yao, H. Luo, Y.W. Guo, X.W. Li, J. Org. Chem. 86, 3367 (2021) 63. K.O. Al-Footy, W.M. Alarif, M.S. Zubair, M.A. Ghandourah, M.M. Aly, Trop. J. Pharm. Res. 15, 1431 (2016) 64. M. Zhao, S. Cheng, W. Yuan, Y. Xi, X. Li, J. Dong, K. Huang, K. Gustafson, P. Yan, Mar. Drugs 14, 111 (2016) 65. T.A. Mohamed, A.I. Elshamy, T.A. Hussien, J.H. Su, J.H. Sheu, M.E.F. Hegazy, J. Asian Nat. Prod. Res. 19, 201 (2017) 66. P. Roy, R. Ashimine, H. Miyazato, J. Taira, K. Ueda, Molecules 21, 679 (2016) 67. B. R. Peng, M. C. Lu, M. El-Shazly, S. L. Wu, K. H. Lai, and J. H. Su, Marine Drugs 16, (2018). 68. Y.C. Liu, B.R. Peng, K.C. Hsu, M. El-Shazly, S.P. Shih, T.E. Lin, F.W. Kuo, Y.C. Chou, H.Y. Lin, M.C. Lu, Mar. Drugs 18, 382 (2020) 69. P.K. Roy, S. Roy, K. Ueda, Fitoterapia 136, 104162 (2019) 70. Q. Zhang, X.-W. Li, L.-G. Yao, B. Wu, Y.-W. Guo, Fitoterapia 133, 70 (2019) 71. S.W. Li, C. Cuadrado, L.G. Yao, A.H. Daranas, Y.W. Guo, Org. Lett. 22, 4093 (2020) 72. S.W. Li, C. Cuadrado, X.J. Huan, L.G. Yao, Z.H. Miao, A. Hernandez Daranas, Y.W. Guo, Bioorgan Chem. 103, 104223 (2020) 73. K.Y. Peng, N.F. Chen, Z.C. Chen, K.H. Tsui, Z.H. Wen, Y. Di Su, Y.C. Chang, Y.H. Chen, M.C. Lu, L.S. Fang, J.J. Chen, T.Y. Wu, Y.C. Wu, P.J. Sung, Tetrahedron Lett. 57, 4239 (2016) 74. Y.D. Su, C.S. Sung, Z.H. Wen, Y.H. Chen, Y.C. Chang, J.J. Chen, L.S. Fang, Y.C. Wu, J.H. Sheu, P.J. Sung, Int. J. Mol. Sci. 17, 79 (2016) 75. T. Ishii, T. Kamada, C.S. Vairappan, J. Asian Nat. Prod. Res. 18, 415 (2016) 76. W. Cheng, X. Li, F. Yin, L. van Ofwegen, W. Lin, Chem. Biodivers. 14, e1700053 (2017) 77. C.R.T. Ahmed, C.Y. Huang, S.Y. Wang, J.H. Sheu, Mar. Drugs 15, 23 (2017) 78. K. Chakraborty, S. Salas, M. Joy, Nat. Prod. Res. 34, 1678 (2020) 79. G. Porras, A.R. Díaz-Marrero, J.M. de la Rosa, L. D'Croz, N. de Pablo, G. Perdomo, I. Cózar-Castellano, J. Darias, M. Cueto, Tetrahedron 74, 2056 (2018) 80. T. Ishii, T. Kamada, C.-S. Phan, C.S. Vairappan, Sains Malays. 47, 319 (2018) 81. K. Bauer, M. Puyana, L. Castellanos, E. Tello, Rec. Nat. Prod. 13, 243 (2019) 82. F. Castellanos, F. Amaya-García, E. Tello, F.A. Ramos, A. Umaña, M. Puyana, J.A.L.C. Resende, L. Castellanos, Nat. Prod. Res. 33, 3533 (2019) 83. A. Tseng, T. Huang, O. Tai, W. Hwang, S. Dai, Mar. Drugs 17, 461 (2019) 84. N. N. Thi, H. Tran, T. Hong, T. Nguyen Van, C. N. Xuan, N. N. Hoai, T. Do Cong, K. Phan Van, and M. Chau Van, Nat Product Res 34, 385 (2020). 85. P.C. Huang, C.C. Tseng, B.R. Peng, C.C. Hu, N.C. Lin, N.F. Chen, J.J. Chen, Z.H. Wen, Y.C. Wu, P.J. Sung, Tetrahedron 75, 921 (2019) 86. P.J. Sung, C.Y. Lee, C.C. Lin, W.F. Chen, G.H. Lee, Z.H. Wen, L.S. Fang, Y.H. Kuo, Heterocycles 98, 984 (2019) 87. S.L. Molina, A.M. Forero, F.I. Ayala, M. Puyana, S. Zea, L. Castellanos, D. Muñoz, G. Arboleda, A.G. Sandoval-Hernández, F.A. Ramos, Mar. Drugs 18, 4 (2019) 88. Y.F. Chen, W.F. Chen, Z.H. Wen, T.L. Hwang, Z.J. Zhang, P.J. Sung, Phytochem. Lett. 33, 31 (2019) 89. P.C. Huang, W.S. Lin, B.R. Peng, Y.C. Chang, L.S. Fang, G.Q. Li, T.L. Hwang, Z.H. Wen, P.J. Sung, Mar. Drugs 17, 214 (2019) 90. Q. Wu, H. Li, M. Yang, A.Q. Jia, W. Tang, H. Wang, Y.W. Guo, Fitoterapia 134, 481 (2019) 91. P. Francis, K. Chakraborty, Med. Chem. Res. 29, 656 (2020) 92. T.H. Huynh, Y.M. Chang, S.N. Yang, G.H. Lee, Z.H. Wen, Y.J. Wu, T.R. Su, P.J. Sung, J. Mol. Struct. 1223, 128970 (2021) 93. Y.Y. Chen, Y.L. Zhang, G.H. Lee, L.K. Tsou, M.M. Zhang, H.P. Hsieh, J.J. Chen, C.Y. Ko, Z.H. Wen, P.J. Sung, Mar. Drugs 19, 77 (2021) 94. C. H. Wu, C. H. Chao, T. Z. Huang, C. Y. Huang, T. L. Hwang, C. F. Dai, and J. H. Sheu, Marine Drugs 16, (2018). 95. P. Combs, J. Med. Chem. 53, 2333 (2010) |
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