Resolution and absolute configuration assignment of a natural racemic chromane from Peperomia obtusifolia (Piperaceae)

Chirality

Volumn 21, Issue 9, 2009, Pages 799-801

  Batista Jr , João Marcos ^a   López, Silvia Noelí ^a   Da Silva Mota, Jonas ^b   Vanzolini, Kenia Lourenço ^c   Cass, Quezia Bezerra ^c   Rinaldo, Daniel ^a   Vilegas, Wagner ^a   Da Silva Bolzani, Vanderlan ^a   Kato, Massuo Jorge ^d   Furlan, Maysa ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^b UNIVERSIDADE ESTADUAL DE MATO GROSSO DO SUL   (Brazil)

^c FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

^d UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Absolute configuration; Circular dichroism; Enantioseparation; Natural products; Optical rotation

Indexed keywords

3,4 DIHYDRO 5 HYDROXY 2,7 DIMETHYL 8 (3'' METHYL 2'' BUTENYL) 2 (4' METHYL 1',3' PENTADIENYL) 2H 1 BENZOPYRAN 6 CARBOXYLIC ACID; CHROMAN DERIVATIVE; UNCLASSIFIED DRUG;

BIOSYNTHESIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFERENCE PAPER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; OPTICAL ROTATION; PEPEROMIA; PEPEROMIA OBTUSIFOLIA; PHYTOCHEMISTRY; PLANT LEAF; PRIORITY JOURNAL; RACEMIC MIXTURE;

BENZOPYRANS; BIOLOGICAL PRODUCTS; CHROMANS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; OPTICAL ROTATION; PEPEROMIA; PLANT LEAVES; STEREOISOMERISM;

EID: 70350561090     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20676     Document Type: Conference Paper

References (11)

1. Wanke S, Jaramillo A, Borsch T, Samain MS, Quandt D, Neinhuis C. Evolution of Piperales-matK gene and trnK intron sequence data reveal lineage specific resolution contrast. Mol Phylogenet Evol 2007;42:477-497. (Pubitemid 44802761)
2. Batista JM Jr, Lopes AA, Ambrósio DL, Regasini LO, Kato MJ, Bolzani VS, Cicarelli RMB, Furlan M. Natural chromenes and chromene derivatives as potential anti-trypanosomal agents. Biol Pharm Bull 2008;31:538-540.
3. Kato MJ, Furlan M. Chemistry and evolution of the Piperaceae. Pure Appl Chem 2007;79:529-538.
4. Tanaka T, Asai F, Iinuma M. Phenolic compounds from Peperomia obtusifolia. Phytochemistry 1998;49:229-232.
5. Burke SJ, Jacobs H, Mclean S, Reynolds WF. Structural and spectral assignment by 2D NMR of a new prenylated benzopyrancarboxylic acid and structural reassignment of a related compound. Magn Reson Chem 2003;41:145-146. (Pubitemid 36166019)
6. Snatzke G, Ho PC. Rules for benzene Cotton-effects. Tetrahedron 1971;27:3645-3653.
7. Cichewicz RH, Kenyon VA, Whitman S, Morales NM, Arguello JF, Holamn TR, Crews P. Redox inactivation of human 15-lipoxygenase by marine-derived meroditerpenes and synthetic chromanes: arche-types for a unique class of selective and recyclable inhibitors. J Am Chem Soc 2004;126:14910-14920. (Pubitemid 39532173)
8. Iwata N, Wang N, Yao X, Kitanaka S. Structures and histamine release inhibitory effects of prenylated orcinol derivatives from Rhododendron dauricum. J Nat Prod 2004;67:1106-1109. (Pubitemid 38971668)
9. Lago JHG, Ramos CS, Casanova DCC, Morandim AA, Bergamo DCB, Cavalheiro AJ, Bolzani VS, Furlan M, Guimaraes EF, Young MCM, Kato MJ. Benzoic acid derivatives from Piper species and their fungitoxic activity against Cladosporium cladosporioides and C. sphaerospermum. J Nat Prod 2004;67:1783-1788. (Pubitemid 39602351)
10. Velozo LSM, Ferreira MJP, Santos MIS, Moreira DL, Emerenciano VP, Kaplan MAC. Unsual chromenes from Peperomia blanda. Phytochemistry 2006;67:492-496.
11. Stocker A, Fretz H, Frick H, Ruttimman A, Woggon WD. The substrate specificity of tocopherol cyclase. Bioorg Med Chem 1996;4:1129-1134.