Vibsane-type diterpenes from leaves and twigs of Viburnum odoratissimum

Fitoterapia

Volumn 109, Issue , 2016, Pages 224-229

  He, Juan ^a   Peng, Li Yan ^a   Tu, Lin ^a   Wu, Xing De ^a   Dong, Liao Bing ^a   Pan, Zheng Hong ^b   Chen, Xuan Qin ^c   Su, Jia ^a   Zhao, Yu ^a   Xu, Gang ^a   Cheng, Xiao ^a   Li, Yan ^a   Zhao, Qin Shi ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Cytotoxicity; Vibsane type diterpenes; Vibsanin X; Vibsanols C H; Viburnum odoratissimum

Indexed keywords

ANTINEOPLASTIC AGENT; CISPLATIN; DITERPENE; UNCLASSIFIED DRUG; VIBSANIN X; VIBSANOL C; VIBSANOL D; VIBSANOL E; VIBSANOL F; VIBSANOL G; VIBSANOL H;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY ASSAY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HEPATOCELLULAR CARCINOMA CELL LINE; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; PLANT LEAF; PRIORITY JOURNAL; VIBURNUM; VIBURNUM ODORATISSIMUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; ISOLATION AND PURIFICATION; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DITERPENES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; PLANT LEAVES; VIBURNUM;

EID: 84956714540     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2016.01.014     Document Type: Article

References (27)

1. Y. Fukuyama, and M. Kubo Chemical diversity of vibsane-type diterpenoids Curr. Top. Phytochem. 10 2011 39 53
2. M. Kubo, Y. Minoshima, D. Arimoto, H. Minami, K. Harada, H. Hioki, and Y. Fukuyama Acetal-bearing rearranged vibsane-type diterpenoids from Viburnum awabuki Heterocycles 77 2009 539 546
3. A.A.H. El-Gamal, S.K. Wang, and C.Y. Duh New diterpenoids from Viburnum awabuki J. Nat. Prod. 67 2004 333 336
4. M. Kubo, T. Fujii, H. Hioki, M. Tanaka, K. Kawazu, and Y. Fukuyama Spirovibsanin A, an unprecedented vibsane-type 18-norditerpene from Viburnum awabuki Tetrahedron Lett. 42 2001 1081 1083
5. Y.C. Shen, C.L. Lin, S.C. Chien, T. Khalil Ashraf, C.L. Ko, and C.H. Wang Vibsane diterpenoids from the leaves and flowers of Viburnum odoratissimum J. Nat. Prod. 67 2004 74 77
6. Y.C. Shen, V.S. Prakash Chaturvedula, L.T. Wang, C.T. Chien, and M.C. Hung New vibsane diterpenes and lupane triterpenes from Viburnum odoratissimum J. Nat. Prod. 65 2002 1052 1055
7. M. Kubo, I.S. Chen, and Y. ukuyama Vibsane-type diterpenes from taiwanese Viburnum odoratissimum Chem. Pharm. Bull. 49 2001 242 245
8. Y. Fukuyama, H. Fujii, H. Minami, H. Takahashi, and M. Kubo Neovibsanin F and its congeners, rearranged vibsane-type diterpenes from Viburnum suspensum J. Nat. Prod. 69 2006 1098 1100
9. M. Kubo, Y. Kishimoto, K. Harada, H. Hioki, and Y. Fukuyama NGF-potentiating vibsane-type diterpenoids from Viburnum sieboldii Bioorg. Med. Chem. Lett. 20 2010 2566 2571
10. X.Q. Chen, Y. Li, J. He, X. Cheng, K. Wang, M.M. Li, Z.H. Pan, L.Y. Peng, and Q.S. Zhao Triterpenoids and diterpenoids from Viburnum chingii Chem. Pharm. Bull. 59 2011 496 498
11. X. Gao, L.D. Shao, L.B. Dong, X. Cheng, X.D. Wu, F. Liu, W.W. Jiang, L.Y. Peng, J. He, and Q.S. Zhao Vibsatins A and B, two new tetranorvibsane-type diterpenoids from Viburnum tinus cv. variegatus Org. Lett. 16 2014 980 983
12. K. Kawazu Diterpene esters with novel skeleton from the leaves of Viburnum awabuki Symp. Pap. - IUPAC Int. Symp. Chem. Nat. Prod. 2 1978 101 103
13. X.Y. Wang, H.M. Shi, and X.B. Li. Chemical constituents of plants from the genus Viburnum Chem. Biodivers. 7 2010 567 593
14. K. Kawazu Bioactive Compounds in leaves of Viburnum odoratissimum Ker. Part 1. Isolation of vibsanines A, B, C, D, E and F from Viburnum odoratissimum Agric. Biol. Chem. 44 1980 1367 1372
15. Y. Fukuyama, H. Minami, K. Takeuchi, M. Kodama, and K. Kawazu Neovibsanines A and B, unprecedented diterpenes from Viburnum awabuki Tetrahedron Lett. 37 1996 6767 6770
16. K.I. Takao, K. Tsunoda, T. Kurisu, A. Sakama, Y. Nishimura, K. Yoshida, and K.I. Tadano Total synthesis of (+)-vibsanin A Org. Lett. 17 2015 756 759
17. Y.W. Mak Jeffrey, and M. Williams Craig Enantioselective total synthesis of (-)-neovibsanin G and (-)-14-epi-neovibsanin G Chem. Commun. 48 2012 287 289
18. H. Imagawa, H. Saijo, H. Yamaguchi, K. Maekawa, T. Kurisaki, H. Yamamoto, M. Nishizawa, M. Oda, M. Kabura, M. Nagahama, J. Sakurai, M. Kubo, M. Nakai, K. Makino, M. Ogata, H. Takahashi, and Y. Fukuyama Syntheses of structurally-simplified and fluorescently-labeled neovibsanin derivatives and analysis of their neurite outgrowth activity in PC12 cells Bioorg. Med. Chem. Lett. 22 2012 2089 2093
19. B.D. Schwartz, J.R. Denton, Y. Lian, H.M.L. Davies, and C.M. Williams Asymmetric [4 + 3] cycloadditions between cinylcarbenoids and dienes: application to the total synthesis of the natural product (-)-5-epi-vibsanin E J. Am. Chem. Soc. 131 2009 8329 8332
20. B.X. Ye, X. Deng, L.D. Shao, Y. Lu, R. Xiao, Y.J. Liu, Y. Jin, Y.Y. Xie, Y. Zhao, L.F. Luo, S. Ma, M. Gao, L.R. Zhang, J. He, W.N. Zhang, Y. Chen, C.F. Xia, M. Deng, T.X. Liu, Q.S. Zhao, S.J. Chen, and Z. Chen Vibsanin B preferentially targets HSP90β, inhibits interstitial leukocyte migration, and ameliorates experimental autoimmune encephalomyelitis J. Immunol. 194 2015 4489 4497
21. X.Q. Chen, L.D. Shao, M. Pal, Y. Shen, X. Cheng, G. Xu, L.Y. Peng, K. Wang, Z.H. Pan, M.M. Li, Y. Leng, J. He, and Q.S. Zhao Hupehenols A-E, selective 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors from Viburnum hupehense J. Nat. Prod. 78 2015 330 334
22. L.D. Shao, J. Xu, X. Gao, J. He, Y. Zhao, L.Y. Peng, H.R. Luo, C.F. Xia, and Q.S. Zhao Synthesis and neurite outgrowth promoting activity of vibsanin B derivatives Tetrahedron Lett. 55 2014 3414 3417
23. L. Tu, G. Xu, Y. Zhao, L.Y. Peng, J. He, N. Guo, and Q.S. Zhao Seven new phenolic glucosides from Viburnum cylindricum Helv. Chim. Acta 92 2009 1324 1332
24. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63
25. L.J. Reed, and H. Muench A simple method of estimating fifty per cent endpoints Am. J. Hyg. 27 1938 493 497
26. M. Kubo, H. Minami, E. Hayashi, M. Kodama, K. Kawazu, and Y. Fukuyama Neovibsanin C, a macrocyclic peroxide-containing neovibsane-type diterpene from Viburnum awabuki Tetrahedron Lett. 40 1999 6261 6265
27. Y. Fukuyama, M. Kubo, H. Minami, H. Yuasa, A. Matsuo, T. Fujii, M. Morisaki, and K. Harada Rearranged vibsane-type diterpenes from Viburnum awabuki and photochemical reaction of vibsanin B Chem. Pharm. Bull. 53 2005 72 80