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

来源：

CHIRALITY | 2009年 / 21卷 / 09期

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

页码：799 / 801

页数：3

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