Absolute configuration of podophyllotoxin related lignans from Bursera fagaroides using vibrational circular dichroism

Phytochemistry

Volumn 72, Issue 17, 2011, Pages 2237-2243

  Velázquez Jiménez, René ^a   Torres Valencia, J Martín ^a   Cerda García Rojas, Carlos M ^b   Hernández Hernández, Juan D ^c   Román Marín, Luisa U ^c   Manríquez Torres, J Jesús ^a   Gómez Hurtado, Mario A ^a   Valdez Calderón, Alejandro ^a   Motilva, Virginia ^d   García Mauriño, Sofía ^d   Talero, Elena ^d   Ávila, Javier ^d   Joseph Nathan, Pedro ^b  

^a UNIVERSIDAD AUTÓNOMA DEL ESTADO DE HIDALGO   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

^c UNIVERSIDAD MICHOACANA DE SAN NICOLÁS DE HIDALGO   (Mexico)

^d UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Absolute configuration; Bursera fagaroides; Burseraceae; Cytotoxicity; Podophyllotoxin derivatives; Vibrational circular dichroism

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ANTINEOPLASTIC AGENT; BENZOFURAN DERIVATIVE; DEOXYPODOPHYLLOTOXIN; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; MORELENSIN; PLANT EXTRACT; PODOPHYLLOTOXIN; YATEIN;

ADENOCARCINOMA; ARTICLE; BURSERACEAE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; COLON TUMOR; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOTHERAPY; PLANT EXUDATE; TUMOR CELL LINE;

4-BUTYROLACTONE; ADENOCARCINOMA; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BENZOFURANS; BURSERA; CELL LINE, TUMOR; CIRCULAR DICHROISM; COLONIC NEOPLASMS; DIOXOLES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHYTOTHERAPY; PLANT EXTRACTS; PLANT EXUDATES; PODOPHYLLOTOXIN;

BURSERA FAGAROIDES; BURSERACEAE;

EID: 80053643525     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.07.017     Document Type: Article

References (26)

1. J.M. Batista Jr., A.N.L. Batista, D. Rinaldo, W. Vilegas, Q.B. Cass, V.S. Bolzani, M.J. Kato, S.N. López, M. Furlan, and L.A. Nafie Absolute configuration reassignment of two chromanes from Peperomia obtusifolia (Piperaceae) using VCD and DFT calculations Tetrahedron: Asymmetr. 21 2010 2402 2407
2. E. Bianchi, K. Sheth, and J.R. Cole Antitumor agents from Bursera fagaroides (Burseraceae) (β-peltatin-A-methylether and 5′-desmethoxy- β-peltatin-A-methylether) Tetrahedron Lett. 32 1969 2759 2762
3. C.F. Brewer, J.D. Loike, S.B. Horwitz, H. Sternlicht, and W.J. Gensler Conformational analysis of podophyllotoxin and its congeners. Structure-activity relationship in microtubule assembly J. Med. Chem. 22 1979 215 221 (Pubitemid 9137308)
4. J. Casanovas, A. Namba, R. Da Silva, and C. Alemán DFT-GIAO study of aryltetralin lignan lactones: Conformational analyses and chemical shifts calculations Bioorg. Chem. 33 2005 484 492 (Pubitemid 41674461)
5. J.R. Cole, E. Bianchi, and E.R. Trumbull Antitumor agents from Bursera microphylla. II. Isolation of a new lignan: burseran J. Pharm. Sci. 58 1969 175 176
6. G.M. Cragg, and D.J. Newman Nature: a vital source of leads for anticancer drug development Phytochem. Rev. 8 2009 313 331
7. E. Debie, P. Bultinck, L.A. Nafie, and R.K. Dukor CompareVOA 2010 Biotools, Inc., Jupiter FL, USA
8. P.M. Dewick Medicinal Natural Products: A Biosynthetic Approach third ed. 2009 John Wiley & Sons Chichester pp. 154-155
9. J.L. Hartwell, and A.W. Schrecker Components of podophyllin. V. The constitution of podophyllotoxin J. Am. Chem. Soc. 73 1951 2909 2916
10. J.D. Hernández, L.U. Román, J. Espiñeira, and P. Joseph-Nathan Ariensin, a new lignan from Bursera ariensis Planta Med. 47 1983 215 217 (Pubitemid 13096860)
11. J.D. Hernández-Hernández, L.U. Román-Marín, C.M. Cerda-García-Rojas, and P. Joseph-Nathan Verticillane derivatives from Bursera suntui and Bursera kerberi J. Nat. Prod. 68 2005 1598 1602 (Pubitemid 41789564)
12. R. Ikeda, T. Nagao, H. Okabe, Y. Nakano, H. Matsunaga, M. Katano, and M. Mori Antiproliferative constituents in Umbelliferae plants III. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm Chem. Pharm. Bull. 46 1998 871 874 (Pubitemid 28257495)
13. S.D. Jolad, R.M. Wiedhopf, and J.R. Cole Cytotoxic agents from Bursera morelensis (Burseraceae): deoxypodophyllotoxin and a new lignan, 5′-desmethoxydeoxy-podophyllotoxin J. Pharm. Sci. 66 1977 892 893 (Pubitemid 8123821)
14. A. Jutiviboonsuk, H. Zhang, G.T. Tan, C. Ma, N.V. Hung, N.M. Cuong, N. Bunyapraphatsara, D.D. Soejarto, and H.H.S. Fong Bioactive constituents from roots of Bursera tonkinensis Phytochemistry 66 2005 2745 2751 (Pubitemid 41727661)
15. E. Lautié, R. Quintero, M.A. Fliniaux, and M.L. Villarreal Selection methodology with scoring system: application to Mexican plants producing podophyllotoxin related lignans J. Ethnopharm. 120 2008 402 412 (Pubitemid 50325403)
16. P.B. McDoniel, and J.R. Cole Antitumor activity of Bursera schlechtendalii (Burseraceae): isolation and structures determination of two new lignans J. Pharm. Sci. 61 1972 1992 1994
17. L.A. Nafie Vibrational circular dichroism: a new tool for the solution-state determination of the structure and absolute configuration of chiral natural product molecules Nat. Prod. Commun. 3 2008 451 466
18. A. Nakahashi, Y. Yaguchi, N. Miura, M. Emura, and K. Monde A vibrational circular dichroism approach to the determination of the absolute configurations of flavorous 5-substituted-2(5H)-furanones J. Nat. Prod. 74 2011 707 711
19. T. Nakanishi, Y. Inatomi, H. Murata, K. Shigeta, N. Iida, A. Inada, J. Murata, M.A. Perez Farrera, M. Iinuma, T. Tanaka, S. Tajima, and N. Oku A new and known cytotoxic aryltetralin-type lignans from stems of Bursera graveolens Chem. Pharm. Bull. 53 2005 229 231 (Pubitemid 40873691)
20. S. Peraza-Sánchez, and L.M. Peña-Rodríguez Isolation of picropolygamain from the resin of Bursera simaruba J. Nat. Prod. 55 1992 1768 1771 (Pubitemid 23023265)
21. T.J. Petcher, H.P. Weber, M. Kuhn, and A. Von Wartburg Crystal structure and absolute configuration of 2′-bromopodophyllotoxin - 0.5 ethyl acetate J. Chem. Soc. Perkin Trans. 2 1973 288 292
22. A.W. Schrecker, and J.L. Hartwell Components of podophyllin XX. The absolute configuration of podophyllotoxin and related lignans J. Org. Chem. 21 1956 381 382
23. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 82 1990 1107 1112 (Pubitemid 20213250)
24. K. Yasunaka, F. Abe, A. Nagayama, H. Okabe, L. Lozada-Pérez, E. López-Villafranco, E. Estrada-Muñiz, A. Aguilar, and R. Reyes-Chilpa Antibacterial activity of crude extracts from Mexican medicinal plants and purified coumarins and xanthones J. Ethnopharmacol. 97 2005 293 299 (Pubitemid 40222032)
25. D.B.M. Wickramaratne, W. Mar, H. Chai, J.J. Castillo, N.R. Farnsworth, D.D. Soejarto, G.A. Cordell, J.M. Pezzuto, and A.D. Kinghorn Cytotoxic constituents of Bursera permollis Planta Med. 61 1995 80 81
26. Y. Xia, J. You, Y. Zhang, and Z. Su Synthesis, anti-virus and anti-tumor activities of dibenzylbutyrolactone lignans and their analogues J. Chem. Res. 9 2009 565 569