The phytoalexins from cauliflower, caulilexins A, B and C: Isolation, structure determination, syntheses and antifungal activity

被引:48
作者
Pedras, M. Soledade C. [1 ]
Sarwar, Mohammed G. [1 ]
Suchy, Mojmir [1 ]
Adio, Adewale M. [1 ]
机构
[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
Brassica oleracea; Cruciferae; brassicanal C synthesis; brassitin; cauliflower; crucifer; Leptosphaeria maculans; 1-methoxyindolyl-3-acetonitrile; Phoma lingam; phytoalexin; spirobrassinin;
D O I
10.1016/j.phytochem.2006.05.020
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Our continuous search for phytoalexins from crucifers led us to examine phytoalexin production in florets of cauliflower (Brassica oleracea var. botrytis) under abiotic (UV light) elicitation. Four known (isalexin, S-(-)-spirobrassinin, 1-methoxybrassitin, brassicanal C) and three new (caulilexins A-C) phytoalexins were isolated. The syntheses and antifungal activity of caulilexins A-C against the economically important pathogenic fungi Leptosphaeria maculans, Rhizoctonia solani and Sclerotinia sclerotiorum, and the first synthesis of brassicanal C are reported. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1503 / 1509
页数:7
相关论文
共 30 条
[1]  
ACHESON RM, 1984, J CHEM RES M, P1301
[2]   Initial and final products, nitriles, and ascorbigens produced in myrosinase-catalyzed hydrolysis of indole glucosinolates [J].
Agerbirk, N ;
Olsen, CE ;
Sorensen, H .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1998, 46 (04) :1563-1571
[3]  
BAILEY JA, 1982, PHYTOALEXINS, P334
[4]   Correlation analyses of phytochemical composition, chemical, and cellular measures of antioxidant activity of broccoli (Brassica oleracea L. var. italica) [J].
Eberhardt, MV ;
Kobira, K ;
Keck, AS ;
Juvik, JA ;
Jeffery, EH .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (19) :7421-7431
[5]  
Gribble GW, 1998, CHEM SOC REV, V27, P395
[6]   CHEMISTRY OF INDOLE GLUCOSINOLATES - INTERMEDIACY OF INDOL-3-YLMETHYL ISOTHIOCYANATES IN THE ENZYMATIC-HYDROLYSIS OF INDOLE GLUCOSINOLATES [J].
HANLEY, AB ;
PARSLEY, KR ;
LEWIS, JA ;
FENWICK, GR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08) :2273-2276
[7]   Indole-3-carbinol inhibition of androgen receptor expression and downregulation of androgen responsiveness in human prostate cancer cells [J].
Hsu, JC ;
Zhang, J ;
Dev, A ;
Wing, A ;
Bjeldanes, LF ;
Firestone, GL .
CARCINOGENESIS, 2005, 26 (11) :1896-1904
[8]   Oviposition stimulants for the cabbage root fly:: isolation from cabbage leaves [J].
Hurter, J ;
Ramp, T ;
Patrian, B ;
Städler, E ;
Roessingh, P ;
Baur, R ;
de Jong, R ;
Nielsen, JK ;
Winkler, T ;
Richter, WJ ;
Müller, D ;
Ernst, B .
PHYTOCHEMISTRY, 1999, 51 (03) :377-382
[9]   HPLC-DAD-MS/MS ESI characterization of unusual highly glycosylated acylated flavonoids from cauliflower (Brassica oleracea L. var. botrytis) agroindustrial byproducts [J].
Llorach, R ;
Gil-Izquierdo, A ;
Ferreres, F ;
Tomás-Barberán, FA .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (13) :3895-3899
[10]   Glucosinolates in cauliflower as biochemical markers for resistance against downy mildew [J].
Ménard, R ;
Larue, JP ;
Silué, D ;
Thouvenot, D .
PHYTOCHEMISTRY, 1999, 52 (01) :29-35