Resolution and Absolute Configuration Assignment of a Natural Racemic Chromane from Peperomia obtusifolia (Piperaceae)

被引:30
作者
Batista, Joao Marcos, Jr. [1 ]
Lopez, Silvia Noeli [1 ]
Mota, Jonas da Silva [2 ]
Vanzolini, Kenia Lourenco [3 ]
Cass, Quezia Bezerra [3 ]
Rinaldo, Daniel
Vilegas, Wagner
Bolzani, Vanderlan da Silva [1 ]
Kato, Massuo Jorge [4 ]
Furlan, Maysa [1 ]
机构
[1] Sao Paulo State Univ, UNESP, Dept Organ Chem, Inst Chem,NuBBE Nucleus Bioassays Biosynthesis &, BR-14800900 Araraquara, SP, Brazil
[2] Mato Grosso State Univ UEMS, Dourados, MS, Brazil
[3] Univ Fed Sao Carlos, Dept Chem, BR-13560 Sao Carlos, SP, Brazil
[4] Univ Sao Paulo, Inst Chem, Sao Paulo, Brazil
关键词
natural products; enantioseparation; circular dichroism; optical rotation; absolute configuration; DERIVATIVES; EVOLUTION; ACID;
D O I
10.1002/chir.20676
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The resolution of the natural racemic chromane 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 (1) isolated from the leaves of Peperomia obtusifolia has been accomplished using stereoselective HPLC. The absolute coil figuration of the resolved enantiomers was determined by the analysis of optical rotations and CD spectra. The finding of a racemic mixture instead of an enantiomerically pure metabolite raises questions about the final steps in the biosynthesis of this class of natural products, suggesting that the intramolecular chromane ring formation step may not be enzymatically controlled at all in P. obtusifolia. Chirality 21:799-801, 2009. (C) 2008 Wiley-Liss, Inc.
引用
收藏
页码:799 / 801
页数:3
相关论文
共 11 条
[1]   Natural chromens and chromene derivatives as potential anti-trypanosomal agents [J].
Batista, Joao Marcos ;
Lopes, Adriana Aparecida ;
Ambrosio, Daniela Luz ;
Regasini, Luis Octavio ;
Kato, Massuo Jorge ;
Bolzani, Vanderlan da Silva ;
Barretto Cicarelli, Regina Maria ;
Furlan, Maysa .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2008, 31 (03) :538-540
[2]   Structural and spectral assignment by 2D NMR of a new prenylated benzopyrancarboxylic acid and structural reassignment of a related compound [J].
Burke, SJ ;
Jacobs, H ;
Mclean, S ;
Reynolds, WF .
MAGNETIC RESONANCE IN CHEMISTRY, 2003, 41 (02) :145-146
[3]   Redox inactivation of human 15-lipoxygenase by marine-derived meroditerpenes and synthetic chromanes: Archetypes for a unique class of selective and recyclable inhibitors [J].
Cichewicz, RH ;
Kenyon, VA ;
Whitman, S ;
Morales, NM ;
Arguello, JF ;
Holman, TR ;
Crews, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (45) :14910-14920
[4]   Structures and histamine release inhibitory effects of prenylated orcinol derivatives from Rhododendron dauricum [J].
Iwata, N ;
Wang, NL ;
Yao, XS ;
Kitanaka, S .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (07) :1106-1109
[5]   Chemistry and evolution of the Piperaceae [J].
Kato, Massuo J. ;
Furlan, Maysa .
PURE AND APPLIED CHEMISTRY, 2007, 79 (04) :529-538
[6]   Benzoic acid derivatives from piper species and their fungitoxic activity against Cladosporium cladosporioides and C-sphaerospermum [J].
Lago, JHG ;
Ramos, CS ;
Casanova, DCC ;
Morandim, AD ;
Bergamo, DCB ;
Cavalheiro, AJ ;
Bolzani, VD ;
Furlan, M ;
Guimaraes, EF ;
Young, MCM ;
Kato, MJ .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (11) :1783-1788
[7]   CIRCULAR DICHROISM .46. RULES FOR BENZENE COTTON-EFFECTS [J].
SNATZKE, G ;
HO, PC .
TETRAHEDRON, 1971, 27 (15) :3645-+
[8]   The substrate specificity of tocopherol cyclase [J].
Stocker, A ;
Fretz, H ;
Frick, H ;
Ruttimann, A ;
Woggon, WD .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (07) :1129-1134
[9]   Phenolic compounds from Peperomia obtusifolia [J].
Tanaka, T ;
Asai, F ;
Iinuma, M .
PHYTOCHEMISTRY, 1998, 49 (01) :229-232
[10]   Unusual chromenes from Peperomia blanda [J].
Velozo, LSM ;
Ferreira, MJP ;
Santos, MIS ;
Moreira, DL ;
Emerenciano, VP ;
Kaplan, MAC .
PHYTOCHEMISTRY, 2006, 67 (05) :492-496