Structural elucidation and bioactivity of novel secondary metabolites from Carex distachya

被引:18
作者
Fiorentino, A [1 ]
D'Abrosca, B [1 ]
Izzo, A [1 ]
Pacifico, S [1 ]
Monaco, P [1 ]
机构
[1] Univ Naples 2, Dipartimento Sci Vita, I-81100 Caserta, Italy
关键词
Carex distachya Desf; carexanes; prenyl stilbenes; NMR analysis; phytotoxicity; Lactuca sativa;
D O I
10.1016/j.tet.2006.01.066
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
Four new carexanes and a new seco-derivative metabolite have been isolated and characterized from the herbaceous plant Carex distachya Desf. All of the structures have been elucidated on the basis of spectroscopic data. These compounds derive from the cyclization of prenylate stylbenoid precursors. The seco-carexane is formed by a further oxidative cleavage of the C-7-C-8 bond. The absolute configurations have been determined by Mosher's method using appropriate chemical correlations. All of the carexanes A-H have been tested for their phytotoxicity against Lactuca sativa. The bioassays showed an inhibitory effect on seed germination for all compounds described in this report. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3259 / 3265
页数:7
相关论文
共 15 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]
Carexanes:: prenyl stilbenoid derivatives from Carex distachya [J].
D'Abrosca, B ;
Fiorentino, A ;
Golino, A ;
Monaco, P ;
Oriano, P ;
Pacifico, S .
TETRAHEDRON LETTERS, 2005, 46 (32) :5269-5272
[3]
Low molecular weight phenols from the bioactive aqueous fraction of Cestrum parqui [J].
D'Abrosca, B ;
DellaGreca, M ;
Fiorentino, A ;
Monaco, P ;
Zarrelli, A .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (13) :4101-4108
[4]
Benzocoumarins from the rhizomes of Juncus acutus [J].
DellaGreca, M ;
Fiorentino, A ;
Isidori, M ;
Previtera, L ;
Temussi, F ;
Zarrellia, A .
TETRAHEDRON, 2003, 59 (26) :4821-4825
[5]
THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792
[6]
HILL RA, 2005, NAT PROD REP, V22, P559
[7]
Five new prenylated stilbenes from the root bark of Lonchocarpus chiricanus [J].
Ioset, JR ;
Marston, A ;
Gupta, MP ;
Hostettmann, K .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (06) :710-715
[8]
STEREOCHEMISTRY OF 2 TETRASTILBENES FROM CAREX SPECIES [J].
KAWABATA, J ;
MISHIMA, M ;
KURIHARA, H ;
MIZUTANI, J .
PHYTOCHEMISTRY, 1995, 40 (05) :1507-1510
[9]
Search for a standard phytotoxic bioassay for allelochemicals.: Selection of standard target species [J].
Macías, FA ;
Castellano, D ;
Molinillo, JMG .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (06) :2512-2521
[10]
A GROWTH-INHIBITORY FACTOR FROM LAMBSQUARTERS (CHENOPODIUM-ALBUM) [J].
MALLIK, MAB ;
PUCHALA, R ;
GROSZ, FA .
JOURNAL OF CHEMICAL ECOLOGY, 1994, 20 (04) :957-967