Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism

Chirality

Volumn 18, Issue 5, 2006, Pages 335-339

  Monde, Kenji ^a   Taniguchi, Tohru ^a   Miura, Nobuaki ^a   Vairappan, Charles S ^b   Suzuki, Minoru ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b UNIVERSITI MALAYSIA SABAH   (Malaysia)

Author keywords

Absolute configuration; Brominated metabolites; DFT calculation; Marine natural products; Sesquiterpene; VCD; Vibrational circular dichroism

Indexed keywords

ACETYLMAJAPOLENE; MAJAPOLENE; SESQUITERPENE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; INFRARED RADIATION; PRIORITY JOURNAL; SPECTROMETRY; VIBRATION;

BROMINE; CARBON TETRACHLORIDE; CIRCULAR DICHROISM; LAURENCIA; METHANOL; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PLANT EXTRACTS; SESQUITERPENES; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 33646358705     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20259     Document Type: Article

References (39)

1. Kobayashi J, Ishibashi M. Marine natural products and marine chemical ecology. In: Barton D, Nakanishi K, Meth-Cohn O, editors. Comprehensive natural products chemistry. Oxford: Elsevier; 1999. p 415-649.
2. Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR Marine natural products. Nat Prod Rep 2005;22:15-61.
3. Faulkner DJ, Highlights of marine natural products chemistry (1972-1999). Nat Prod Rep 2000;17:1-6.
4. Tanaka J, Kuniyoshi M, Tanaka C, Issa HH, Balansa W, Otsuka M, Githige WP, Higa T. Diverse metabolites of coral reef organisms. Pure Appl Chem 2005;77:83-89.
5. Pietra F, Evolution of the secondary metabolite versus evolution of the species. Pure Appl Chem 2002;74:2207-2211.
6. Suzuki M, Vairappan CS. Halogenated secondary metabolites from Japanese species of the red algal genus Laurencia (Rhodomelaceae, Ceramiales). Current Topics in Phytochemistry 2005; (in press).
7. Fernandez JJ, Souto ML, Norte M. Marine polyether triterpenes. Nat Prod Rep 2000;17:235-246.
8. Vairappan CS, Kawamoto T, Miwa H, Suzuki M. Potent antibacterial activity of halogenated compounds against antibiotic-resistant bacteria. Planta Medica 2004;70:1087-1090.
9. Butler A, Carter-Franklin JN. The role of vanadium bromoperoxidase in the biosynthesis of halogenated marine natural products. Nat Prod Rep 2004;21:180-188.
10. Fuller RW, Cardellina IIJH, Jurek J, Scheuer PJ, Alvarado-Lindner B, McGuire M, Gray GN. Steiner JR, Clardy J, Menez E, Shoemaker RH, Newman DJ, Snader KM, Boyd MR Isolation and structure/activity features of halomon-related antitumor monoterpenes from the red alga Portieria hornemunnii. J Med Chem 1994;37:4407-4411.
11. König GM, Wright AD, Linden A. Plocamium hamatum and its monoterpenes: chemical and biological investigations of the tropical marine red alga. Phytochemistry 1999;52:1047-1053.
12. Fuller RW, Cardellina IIJH, Kato Y, Brinen LS, Clardy J, Snader KM, Boyd MR. A pentahalogenated monoterpene from the red alga Portieria homeniannii produces a novel cytotoxicity profile against a diverse panel of human tumor cell lines. J Med Chem 1992;35:3007-3011.
13. Vazquez JT, Chang M, Nakanishi K, Puertitols. novel sesquiterpenes from Laurencia obtuse. Structure elucidation and absolute configuration and conformation based on circular dichroism. J Nat Prod 1988;51:1257-1260.
14. Aknin M, Ahond A, Chiaroni A, Poupat C, Riche C, Kornprobst JM. Isolement, determination structurale et configuration absolue de l'almadioxyde. Tetrahedron Lett 1989;30:559-562 (in French).
15. Howard BM, Fenical W. Structure, chemistry, and absolute configuration of 1(S)-Bromo4(R)-hydroxy-(-)-selin-7-ene from a marine red alga Lauremia Sp. J Org Chem 1977;42:2518-2520.
16. Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J Am Chem Soc 1991;113:4092-4096.
17. Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α- trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 1973;95:512-519.
18. Bijvoet JM, Peerdeman AF, van Bommel AJ. Determination of the absolute configuration of optically active compounds by means of X-rays. Nature 1951;168:271-272.
19. Pham-Tuan H, Larsson C, Hoffmann F, Bergman Å, Fröba M, Hühnerfuss H. Enantioselective semi-preparative HPLC separation of PCB metabolites and their absolute structure elucidation using electronic and vibrational circular dichroism. Chirality 2005;17:266-280.
20. Döbler J, Peters N, Larsson C, Bergman Å, Geidel E, Hühnerfuss H. The absolute structures of separated PCB-methylsulfone enantiomers determined by vibrational circular dichroism and quantum chemical calculations. J Mol Struct 2002;586:159-166.
21. nd ed. New York: Wiley; 2000. p 97-131.
22. Freedman TB, Cao X, Dukor RK, Nafie LA. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003;15:743-758.
23. Polavarapu PL, He J. Chiral analysis using mid-IR vibrational CD spectroscopy. Anal Chem 2004;76:61A-67A.
24. Taniguchi T, Miura N, Nishimura SI, Monde K. Vibrational circular dichroism: Chiroptical analysis of biomolecules. Mol Nutr Food Res 2004;48:246-254.
25. He J, Wang F, Polavarapu PL. Absolute configurations of chiral herbicides determined from vibrational circular dichroism. Chirality 2005;17:81-58.
26. Dunmire D, Freedman TB, Nafie LA, Aeschlimann C, Gerber JG, Gal J. Determination of the absolute configuration and solution conformation of the antifungal agents ketoconazole, itraconazole, and miconazole with vibrational circular dichroism. Chirality 2005;17:8101-8108.
27. Cichewicz RH, Clifford LJ, Ussen PR, Cao X, Freedman TB, Nafie LA, Deschamps JD, Kenyon VA, Flanary JR, Holman TR, Crews P. Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis. Bioorgan Med Chem 2005;13:5600-5612.
28. Devlin FJ, Stephens PJ, Besse P. Are the absolute configurations of 2-(1-hydroxyethyl)-chromen-4-one and its 6-bromo derivative determined by X-ray crystallography correct? A vibrational circular dichroism study of their acetate derivatives. Tetrahedron Asymmetr 2005;16:1557-1566.
29. nd ed. New York: Wiley; 2000. p 621-666.
30. Monde K, Taniguchi T, Miura N, Nishimura SI. Specific band observed in VCD predicts the anomeric configuration of carbohydrates. J Am Chem Soc 2004;126:9496-9497.
31. Suzuki M, Takahashi Y, Mitome Y, Itoh T, Abe T, Masuda M. Brominated metabolites from an Okinawan Laurencia intricata. Phytochemistry 2002;60:861-867.
32. Takahashi Y, Daitoh M, Suzuki M, Abe T, Masuda M. Halogenated metabolites from the new Okinawan red alga Laurencia yonaguniensis. J Nat Prod 2002;65:395-398.
33. Suzuki M, Daitoh M, Vairappan CS, Abe T, Masuda M. Novel halogenated metabolites from the Malaysian Laurencia pannosa. J Nat Prod 2001;64:597-602.
34. Erickson KL, Beutler JA, Gray GN, Cardellina UJH, Boyd MR. Majapolene A, a cytotoxic peroxide, and related sesquiterpenes from the red alga Laurencia majuscula. J Nat Prod 1995;58:1848-1860.
35. The detailed isolation procedure and results of antibacterial activity will be reported elsewhere.
36. Goto H, Osawa E. Corner flapping: a simple and fast algorithm for exhaustive generation of ring conformations. J Am Chem Soc 1989;111:8950-8951.
37. Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ. Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 1996;252:211-220.
38. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr,JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz AP, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara Challacombe AM, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA, Gaussian03, Gaussian, Inc., Pittsburgh, PA; 2003.
39. Stephens PJ. Theory of vibrational circular dichroism. J Phys Chem 1985;89:748-752.