Cytotoxic Orbitide from the Latex of Croton urucurana

被引：19

作者：

Candido-Bacani, Priscila de M. ^{[1
,2
]}

Figueiredo, Patricia de O. ^{[1
]}

Matos, Maria de F. C. ^{[2
]}

Garcez, Fernanda R. ^{[1
]}

Garcez, Walmir S. ^{[1
]}

机构：

[1] Univ Fed Mato Grosso do Sul, Inst Quim, BR-79074460 Campo Grande, MS, Brazil

[2] Univ Fed Mato Grosso do Sul, Ctr Ciencias Biol & Saude, BR-79070900 Campo Grande, MS, Brazil

来源：

JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 11期

关键词：

CYCLIC HEPTAPEPTIDE; DRAGONS BLOOD; PEPTIDES; NONAPEPTIDE; EUPHORBIACEAE; MAHAFACYCLIN; CYCLOGOSSINE; NOMENCLATURE; PHARMACOLOGY; OCTAPEPTIDE;

D O I：

10.1021/acs.jnatprod.5b00724

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The bioactive ethyl acetate phase obtained from the latex of Croton urucurana Baillon afforded a novel orbitide (1), [1-9-N alpha C]-crourorb A1, that proved active against NCI-ADR/RES (ovary, multidrug-resistance phenotype) cells with the same potency as doxorubicin (positive control) and inactive up to the highest concentration tested against nontumor NIH/3T3 cells. The structure elucidation was based on 1D and 2D NMR spectroscopy, further supported by HRESIMS data and by application of Marfey's method for determination of the absolute configuration of its amino acid residues. This is the first orbitide obtained from C. urucurana.

引用

页码：2754 / 2760

页数：7

共 43 条

[1]

Altei W. F., 2009, ANN M BRAZ SOC BIOCH, V41

[2] Jatrophidin I, a cyclic peptide from Brazilian Jatropha curcas L.: Isolation, characterization, conformational studies and biological activity [J].

Altei, Wanessa F. ;

Picchi, Douglas G. ;

Abissi, Barbara M. ;

Giesel, Guilherme M. ;

Flausino, Otavio, Jr. ;

Reboud-Ravaux, Michele ;

Verli, Hugo ;

Crusca, Edson, Jr. ;

Silveira, Edilberto R. ;

Cilli, Eduardo M. ;

Bolzani, Vanderlan S. .

PHYTOCHEMISTRY, 2014, 107 :91-96

[3] Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature [J].

Arnison, Paul G. ;

Bibb, Mervyn J. ;

Bierbaum, Gabriele ;

Bowers, Albert A. ;

Bugni, Tim S. ;

Bulaj, Grzegorz ;

Camarero, Julio A. ;

Campopiano, Dominic J. ;

Challis, Gregory L. ;

Clardy, Jon ;

Cotter, Paul D. ;

Craik, David J. ;

Dawson, Michael ;

Dittmann, Elke ;

Donadio, Stefano ;

Dorrestein, Pieter C. ;

Entian, Karl-Dieter ;

Fischbach, Michael A. ;

Garavelli, John S. ;

Goeransson, Ulf ;

Gruber, Christian W. ;

Haft, Daniel H. ;

Hemscheidt, Thomas K. ;

Hertweck, Christian ;

Hill, Colin ;

Horswill, Alexander R. ;

Jaspars, Marcel ;

Kelly, Wendy L. ;

Klinman, Judith P. ;

Kuipers, Oscar P. ;

Link, A. James ;

Liu, Wen ;

Marahiel, Mohamed A. ;

Mitchell, Douglas A. ;

Moll, Gert N. ;

Moore, Bradley S. ;

Mueller, Rolf ;

Nair, Satish K. ;

Nes, Ingolf F. ;

Norris, Gillian E. ;

Olivera, Baldomero M. ;

Onaka, Hiroyasu ;

Patchett, Mark L. ;

Piel, Joern ;

Reaney, Martin J. T. ;

Rebuffat, Sylvie ;

Ross, R. Paul ;

Sahl, Hans-Georg ;

Schmidt, Eric W. ;

Selsted, Michael E. .

NATURAL PRODUCT REPORTS, 2013, 30 (01) :108-160

[4] Curcacycline B, a cyclic nonapeptide from Jatropha curcas enhancing rotamase activity of cyclophilin [J].

Auvin, C ;

Baraguey, C ;

Blond, A ;

Lezenven, F ;

Pousset, JL ;

Bodo, B .

TETRAHEDRON LETTERS, 1997, 38 (16) :2845-2848

[5] Pohlianins A, B and C, cyclic peptides from the latex of Jatropha pohliana ssp molissima [J].

Auvin-Guette, C ;

Baraguey, C ;

Blond, A ;

Xavier, HS ;

Pousset, JL ;

Bodo, B .

TETRAHEDRON, 1999, 55 (38) :11495-11510

[6] Cyclogossine B, a cyclic octapeptide from Jatropha gossypifolia [J].

AuvinGuette, C ;

Baraguey, C ;

Blond, A ;

Pousset, JL ;

Bodo, B .

JOURNAL OF NATURAL PRODUCTS, 1997, 60 (11) :1155-1157

[7] Isolation, structure and synthesis of mahafacyclin B, a cyclic heptapeptide from the latex of Jatropha mahafalensis [J].

Baraguey, C ;

Blond, A ;

Cavelier, F ;

Pousset, JL ;

Bodo, B ;

Auvin-Guette, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (17) :2098-2103

[8] Mahafacyclin A, a cyclic heptapeptide from Jatropha mahafalensis exhibiting β-bulge conformation [J].

Baraguey, C ;

Blond, A ;

Correia, I ;

Pousset, JL ;

Bodo, B ;

Auvin-Guette, C .

TETRAHEDRON LETTERS, 2000, 41 (03) :325-329

[9]

Baraguey C., 1998, J CHEM SOC P1, V18, P3033

[10] Labaditin, a cyclic peptide with rich biotechnological potential: preliminary toxicological studies and structural changes in water and lipid membrane environment [J].

Barbosa, S. C. ;

Cilli, E. M. ;

Dias, Luis G. ;

Stabeli, Rodrigo G. ;

Ciancaglini, P. .

AMINO ACIDS, 2011, 40 (01) :135-144

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