Unusual sesquiterpene glucosides from Amaranthus retroflexus

被引：48

作者：

Fiorentino, Antonio

DellaGreca, Marina

D'Abrosca, Brigida

Golino, Annunziata

Pacifico, Severina

Izzo, Angelina

Monaco, Pietro

机构：

[1] Seconda Univ Napoli, Dipartimento Sci Vita, I-81100 Caserta, Italy

[2] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

来源：

TETRAHEDRON | 2006年 / 62卷 / 38期

关键词：

Amaranthus retroflexus; Amaranthaceae; nerolidol glucosides; amarantholidosides; NMR analysis; phytotoxic effect; autotoxic effect; Taraxacum officinale;

D O I：

10.1016/j.tet.2006.07.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Implementing the phytochemical study of the weed Amaranthus retroflexus, four new sesquiterpene glucosides were isolated from the methanolic extract of the plant. The structures of these metabolites are determined on the basis of the mass spectrometry, and I D and 2D NMR spectroscopies (DQ-COSY, TOCSY, HSQC, HSQC-TOCSY, HMBC, and NOESY). Two compounds are characterized by a new aglycone and differed from the site of glucosylation. The other two compounds are dimeric diastereoisomers. All the glucoside sesquiterpenes were tested on the wild species Taraxacum officinale to evaluate the role of this weed in the habitat and on the seed of A. retroflexus to verify the potential autotoxic effect of the plant. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：8952 / 8958

页数：7

相关论文

共 14 条

[1]

Amarantholidols and amarantholidosides:: new nerolidol derivatives from the weed Amaranthus retroflexus [J].

D'Abrosca, B ;

De Maria, P ;

DellaGreca, M ;

Fiorentino, A ;

Golino, A ;

Izzo, A ;

Monaco, P .

TETRAHEDRON, 2006, 62 (04) :640-646

[2]

Structural characterization of phytotoxic terpenoids from Cestrum parqui [J].

D'Abrosca, B ;

DellaGreca, M ;

Fiorentino, A ;

Monaco, P ;

Natale, A ;

Oriano, P ;

Zarrelli, A .

PHYTOCHEMISTRY, 2005, 66 (22) :2681-2688

[3]

Natural products as sources for new mechanisms of herbicidal action [J].

Duke, SO ;

Romagni, JG ;

Dayan, FE .

CROP PROTECTION, 2000, 19 (8-10) :583-589

[4]

ALPHA-PHENYLETHYLAMINE BASED CHIRAL PHOSPHOLIDINES - NEW AGENTS FOR THE DETERMINATION OF THE ENANTIOMERIC EXCESS OF CHIRAL ALCOHOLS, AMINES AND THIOLS BY MEANS OF P-31 NMR [J].

HULST, R ;

DEVRIES, NK ;

FERINGA, BL .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :699-708

[5]

Allelopathic effects of foliage extracts from four Chenopodiaceae species on seed germination [J].

Jefferson, LV ;

Pennacchio, M .

JOURNAL OF ARID ENVIRONMENTS, 2003, 55 (02) :275-285

[6]

Germination and growth inhibitors from wheat (Triticum aestivium L.) husks [J].

Kato, T ;

Saito, N ;

Kashimura, K ;

Shinohara, M ;

Kurahashi, T ;

Taniguchi, K .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (22) :6307-6312

[7]

Application of chiral bidentate NMR solvents for assignment of the absolute configuration of alcohols: scope and limitation [J].

Kobayashi, Y ;

Hayashi, N ;

Kishi, Y .

TETRAHEDRON LETTERS, 2003, 44 (40) :7489-7491

[8]

Toward the creation of NMR Databases in chiral solvents: Bidentate chiral NMR solvents for assignment of the absolute configuration of acyclic secondary alcohols [J].

Kobayashi, Y ;

Hayashi, N ;

Kishi, Y .

ORGANIC LETTERS, 2002, 4 (03) :411-414

[9]

Application of Hansch's model to guaianolide ester derivatives:: A quantitative structure-activity relationship study [J].

Macías, FA ;

Velasco, RF ;

Castellano, D ;

Galindo, JCG .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (09) :3530-3539

[10]

HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096