Structure of Echivulgarine, a Pyrrolizidine Alkaloid Isolated from the Pollen of Echium vulgare

被引：12

作者：

Cairns, Eric ^{[1
]}

Hashimi, Muhammad Ali ^{[2
]}

Singh, A. Jonathan ^{[2
,3
]}

Eakins, Galen ^{[2
,4
]}

Lein, Matthias ^{[2
,5
]}

Keyzers, Robert ^{[2
,3
]}

机构：

[1] AsureQual Ltd, Lower Hutt 5040, New Zealand

[2] Victoria Univ Wellington, Sch Chem & Phys Sci, Wellington 6140, New Zealand

[3] Victoria Univ Wellington, Ctr Biodiscovery, Wellington 6140, New Zealand

[4] Victoria Univ Wellington, MacDiarmid Inst Adv Mat & Nanotechnol, Wellington 6140, New Zealand

[5] Massey Univ Auckland, New Zealand Inst Adv Study, Ctr Theoret Chem & Phys CTCP, Auckland, New Zealand

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2015年 / 63卷 / 33期

关键词：

structural reassignment; DFT; absolute configuration; qNMR; SOLID-PHASE EXTRACTION; STRUCTURE ELUCIDATION; IN-VITRO; TOXICITY; HEPATOTOXICITY; DERIVATIVES; HONEY;

D O I：

10.1021/acs.jafc.5b02402

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

1,2-Dehydropyrrolizidine alkaloids are common toxic metabolites isolated from plants within the Boraginaceae, in particular from the genera Heliotropium and Echium. Previous studies have deduced the structures of these often potent bioactives based upon mass spectrometric evidence, but these identifications have not established conclusive connectivity and configurational data. Herein, we describe the isolation and full structural characterization of echivulgarine, occurring in the pollen of Echium vulgare and correct the structure previously ascribed to the compound, using a comprehensive combination of both experimental and calculated nuclear magnetic resonance and electronic circular dichroism spectroscopic data.

引用

页码：7421 / 7427

页数：7

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