Stereochemistry of 16α-hydroxyfriedelin and 3-Oxo-16-methylfriedel- 16-ene established by 2D NMR spectroscopy

Molecules

Volumn 14, Issue 2, 2009, Pages 598-607

  Duarte, Lucienir Pains ^a   Silva De Miranda, Roqueline Rodrigues ^b   Rodrigues, Salomão Bento Vasconcelos ^a   De Fátima Silva, Grácia Divina ^a   Filho, Sidney Augusto Vieira ^c   Knupp, Vagner Fernandes ^d  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^b Campus II   (Brazil)

^c FEDERAL UNIVERSITY OF OURO PRETO   (Brazil)

^d Centro Tecnológico de Minas Gerais Belo Horizonte   (Brazil)

Author keywords

16 hydroxyfriedelin; 3 oxo 16methylfriedel 16 ene; Celastraceae; Salacia elliptica

Indexed keywords

FRIEDELIN; HERBACEOUS AGENT; TRITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SALACIA; STEREOISOMERISM;

DRUGS, CHINESE HERBAL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SALACIA; STEREOISOMERISM; TRITERPENES;

EID: 61449150458     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14020598     Document Type: Article

References (19)

1. Wolf, B.M.; Weisbrode, S.E. Safety evaluation of an extract from Salada oblonga. Food Chem. Toxicol. 2003, 4, 867-870.
2. Yoshikawa, M.; Murakami, T.; Shimada, H.; Matsuda, H.; Yamahara, J.; Tanabe, G.; Muraoka, O. Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the ayurvedic traditional medicine Salacia reticulata in Sri Lanka and India. Tetrahedron Lett. 1997, 38, 8367-8370.
3. Jeller, A.H.; Silva, D.H.S.; Lião. L.M.; Bolzani, V.S.; Furlan; M. Antioxidant phenolic and quinonemethide triterpenes from Cheiloclinium cognatum. Phytochemistry 2004, 65, 1977-1982.
4. Deepa, M.A.; Bai, V.N.; Antibacterial activity of Salacia beddomei. Fitoterapia 2004, 75, 589-591.
5. Kuo, Y.H.; Kuo, L.M.Y. Antitumour and anti-AIDS triterpenes from Celastrus hindsii. Phytochemistry 1997, 44, 1275-1281.
6. Oliveira, M. L. G.; Duarte, L. P.; Silva, G. D. F.; Vieira Filho, S.A.; Knupp, V.F.; Alves; F.G.P. 3-Oxo-12a-hydroxyfriedelane from Maytenus gonoclada: structure elucidation by (1)H and (13)C chemical shifts assignments and 2D-NMR spectroscopy. Magn. Reson. Chem. 2007, 45, 895-898.
7. Oliveira, D.M.; Silva, G.D.F.; Duarte, L.P.; Vieira Filho, S.A. Chemical constituents isolated from roots of Maytenus acanthophylla Reissek (Celastraceae). Bioch. Syst. Ecol., 2006, 34, 661-665.
8. Rizvi, S.H.; Shoeb, A.; Kapil, R.S.; Popli, S.P. Antidesmanol - New Pentacyclic Triterpenoid From Antidesma menasu Miq Ex Tul. Experientia 1980, 36, 146-147.
9. 13C NMR spectra of four triterpenes of the ursane, artane, lupane and friedelane groups. Magn. Reson.Chem. 2000, 38, 201-206.
10. Vieira, H.S.; Takahashi, J.A.; Gunatilaka, A.A.L.; Boaventura, M.A.D. IH and 13C NMR signal assignments of a novel Baeyer-Villiger originated diterpene lactone. Magn. Reson. Chem. 2006, 44, 146-150.
11. Fernandez, A.H.; Cerero, S.M.; Jimenez, F.M. About the Timing of Wagner-Meerwein and Nametkin Rearrangements, 6,2-Hydride Shift, Proton Elimination and Cation Trapping in 2Norbornyl Carbocations Tetrahedron 1998, 54, 4607-4614.
12. Starling, S.M.; Vonwiller, S.C.; Reek, J.N.H. Effect of Ortho Substituents on the Direction of 1,2-Migrations in the Rearrangement of 2-exo-Arylfenchyl Alcohols. J. Org. Chem. 1998, 63, 2262-2272.
13. Kikuchi, T.; Niwa, M.; Yokoi, T.; Kadota, S. Studies on the Neutral Constituents of Pachysandra terminalis SIEB, et ZUCC VIII. Methyl Migration in the Dehydration Reaction of Pachysonol and Pachysandiol-B Derivatives. Chem. Pharm. Bull. 1981, 29, 1819-1826.
14. Hao; X.; Xuehui, L.; Yuxin, C.; Min, Z.; Jiaxiang, S. NMR study on the reaction of rearrangement of 17β-hydroxy-7α-methyl-19-nor-17-α- pregn-5(10)-en-20-yn-3-one. Bopuxue Zazhi 2000, 17, 17-22.
15. Lebedeva, T.L.; Vointseva, I.I.; Gilman, L.M.; Petrovskii; P.V.; Larina, T.A.; Topchiev, A.V. Solvent-induced allylic rearrangements in poly(trichlorobutadiene) chains. Russ. Chem. Bull. 1997, 46, 732-738.
16. Mitsuo, K.; Zhang, L.C.; Kabuto, C.; Sakurai, H. Synthesis and Reactions of Neutral Hypercoordinate Allylsilicon Compounds Having a Tropolonato Ligand Organometallics 1996, 75, 5335-5341.
17. 13C NMR Spectra of pentacyclic triterpenoids - a compilation and some salient features Phytochemistry 1994, 37, 1517-1575.
18. Courtney, J.L.; Shannon, J.S. Studies in mass spectrometry triterpenoids: structure assignment to some friedelane derivatives. Tetrahedron Lett. 1963, 7, 13-20.
19. Matos, F.J.A. Introdução a Fitoquímica Experimental. Editora UFC: Fortaleza, Brazil, 1988; p. 126