Isolation and phytotoxicity of apocarotenoids from Chenopodium album

被引:86
作者
DellaGreca, M
Di Marino, C
Zarrelli, A
D'Abrosca, B
机构
[1] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy
[2] Univ Naples 2, Dipartimento Sci Vita, I-81100 Caserta, Italy
来源
JOURNAL OF NATURAL PRODUCTS | 2004年 / 67卷 / 09期
关键词
D O I
10.1021/np049857q
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two new compounds (1, 2) and 16 apocarotenoids (3-18) were isolated from the weed Chenopodium album. The structures of new apocarotenoids were determined to be (3R,6R,7E,9E,11E)-3-hydroxy-13-apo-alpha-caroten-13-one (1) and (6S,7E,9E,11E)-3-oxo-13-apo-alpha-caroten-13-one (2) by spectroscopic, NMR, and MS analysis. Five of the known compounds (5, 6, 13, 15, and 17) were previously reported only as synthetic compounds. Effects of these compounds on germination and growth of Lactuca sativa (lettuce) were studied in the 10(-4)-10(-7) M concentration range.
引用
收藏
页码:1492 / 1495
页数:4
相关论文
共 21 条
[1]   TOBACCO CHEMISTRY .24. (9R)-9-HYDROXY-4-MEGASTIGMEN-3-ONE - NEW TOBACCO CONSTITUENT [J].
AASEN, AJ ;
HLUBUCEK, JR ;
ENZELL, CR .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (03) :285-288
[2]   SYNTHESIS OF OPTICALLY PURE GRASSHOPPER KETONE AND OF ITS DIASTEREOISOMERS AND RELATED-COMPOUNDS [J].
BAUMELER, A ;
BRADE, W ;
HAAG, A ;
EUGSTER, CH .
HELVETICA CHIMICA ACTA, 1990, 73 (03) :700-715
[3]   TOBACCO CHEMISTRY .47. (3S,6R,7E,9R)-4, 7-MEGASTIGMADIENE-3,9-DIOL AND (3S STAR,6R STAR,7E,9S STAR)-4,7-MEGASTIGMADIENE-3,9-DIOL .2. NEW NOR-CAROTENOIDS OF GREEK TOBACCO [J].
BEHR, D ;
WAHLBERG, I ;
NISHIDA, T ;
ENZELL, CR .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1978, 32 (06) :391-394
[4]  
Britton G., 1995, Carotenoids: Spectroscopy, V1B, P13
[5]   Cinnamic acid amides from Chenopodium album:: effects on seeds germination and plant growth [J].
Cutillo, F ;
D'Abrosca, B ;
DellaGreca, M ;
Di Marino, C ;
Golino, A ;
Previtera, L ;
Zarrelli, A .
PHYTOCHEMISTRY, 2003, 64 (08) :1381-1387
[6]  
CUTILLO F, IN PRESS NAT PROD RE
[7]   Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui [J].
D'Abrosca, B ;
DellaGreca, M ;
Fiorentino, A ;
Monaco, P ;
Oriano, P ;
Temussi, F .
PHYTOCHEMISTRY, 2004, 65 (04) :497-505
[8]   Composition of Australian honey extractives .1. Norisoprenoids, monoterpenes, and other natural volatiles from blue gum (Eucalyptus leucoxylon) and yellow box (Eucalyptus melliodora) honeys [J].
Darcy, BR ;
Rintoul, GB ;
Rowland, CY ;
Blackman, AJ .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (05) :1834-1843
[9]  
HARADA N, 1983, CIRCULAR DICHROIC SP, P240
[10]   CAROTENOIDS AND RELATED COMPOUNDS .29. STEREOCHEMISTRY AND SYNTHESIS OF ALLENIC END GROUP - ABSOLUTE-CONFIGURATION OF ZEAXANTHIN [J].
HLUBUCEK, JR ;
HORA, J ;
RUSSELL, SW ;
TOUBE, TP ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (07) :848-852