Regiolone and Isosclerone, Two Enantiomeric Phytotoxic Naphthalenone Pentaketides: Computational Assignment of Absolute Configuration and Its Relationship with Phytotoxic Activity

被引：61

作者：

Evidente, Antonio ^{[1
]}

Superchi, Stefano ^{[2
]}

Cimmino, Alessio ^{[1
,3
]}

Mazzeo, Giuseppe ^{[2
]}

Mugnai, Laura ^{[4
]}

Rubiales, Diego ^{[3
]}

Andolfi, Anna ^{[1
]}

Villegas-Fernandez, Angel M. ^{[3
]}

机构：

[1] Univ Naples Federico II, Dipartimento Sci Suolo Pianta Ambiente & Prod Ani, I-80055 Portici, Italy

[2] Univ Basilicata, Dipartimento Chim, I-85100 Potenza, Italy

[3] CSIC, Inst Sustainable Agr, Cordoba 14080, Spain

[4] Univ Florence, Dipartimento Biotecnol Patol Vegetale, I-50144 Florence, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 28期

关键词：

Phytotoxicity; Configuration determination; Circular dichroism; Biological activity; Ab initio calculations; AB-INITIO CALCULATION; OPTICAL-ROTATION; CHIROPTICAL PROPERTIES; JUGLANS-REGIA; METABOLITES; ESCA; CONSTITUENTS; DERIVATIVES; BOTRYTIS;

D O I：

10.1002/ejoc.201100941

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute configurations of regiolone and isosclerone, two enantiomeric bioactive naphthalenone pentaketides produced by fungi and plants, have been unambiguously assigned by ab initio computational prediction of their theoretical optical rotatory powers and electronic circular dichroism spectra. Isosclerone is produced by the plant pathogen Botrytis cinerea, whereas regiolone is produced by B. fabae. The phytotoxic activities of the two compounds were tested for comparison on faba bean (host of both pathogens) and vine plants (host of only B. cinerea); the (R) configuration at C-4 was found to be a fundamental structural feature for bioactivity.

引用

页码：5564 / 5570

页数：7

共 55 条

[21] New Bioactive 2,3-Epoxycyclohexenes and Isocoumarins from the Endophytic Fungus Phomopsis sp from Laurus Azorica [J].