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
[21]   Strategies of cruciferous pathogenic fungi: Detoxification of the phytoalexin cyclobrassinin by mimicry [J].
Pedras, MSC ;
Okanga, FI .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1999, 47 (03) :1196-1202
[22]   Phytoalexins from crucifers: synthesis, biosynthesis, and biotransformation [J].
Pedras, MSC ;
Okanga, FI ;
Zaharia, IL ;
Khan, AQ .
PHYTOCHEMISTRY, 2000, 53 (02) :161-176
[23]   Effect of glutathione-S-transferase polymorphisms on the cancer preventive potential of isothiocyanates:: An epidemiological perspective [J].
Seow, A ;
Vainio, H ;
Yu, MC .
MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 2005, 592 (1-2) :58-67
[24]   A NEW AND SIMPLE SYNTHESIS OF 1-HYDROXYINDOLE DERIVATIVES [J].
SOMEI, M ;
KAWASAKI, T .
HETEROCYCLES, 1989, 29 (07) :1251-1254
[25]   THE CHEMISTRY OF INDOLES .25. SYNTHETIC STUDY FOR 1-METHOXYINDOLES AND 1-METHOXY-2-OXINDOLES [J].
SOMEI, M ;
SATO, H ;
KOMURA, N ;
KANEKO, C .
HETEROCYCLES, 1985, 23 (05) :1101-1106
[26]   Synthesis, absolute configuration, and enantiomeric enrichment of a cruciferous oxindole phytoalexin, (S)-(-)-spirobrassinin, and its oxazoline analog [J].
Suchy, M ;
Kutschy, P ;
Monde, K ;
Goto, H ;
Harada, N ;
Takasugi, M ;
Dzurilla, M ;
Balentová, E .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) :3940-3947
[27]   STUDIES ON STRESS METABOLITES .7. NOVEL SULFUR-CONTAINING PHYTOALEXINS FROM THE CHINESE CABBAGE BRASSICA-CAMPESTRIS L SSP PEKINENSIS (CRUCIFERAE) [J].
TAKASUGI, M ;
MONDE, K ;
KATSUI, N ;
SHIRATA, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (01) :285-289
[28]   STUDIES ON STRESS METABOLITES .6. SPIROBRASSININ, A NOVEL SULFUR-CONTAINING PHYTOALEXIN FROM THE DAIKON RHAPHANUS-SATIVUS L VAR HORTENSIS (CRUCIFERAE) [J].
TAKASUGI, M ;
MONDE, K ;
KATSUI, N ;
SHIRATA, A .
CHEMISTRY LETTERS, 1987, (08) :1631-1632
[29]   Quantitative determination of intact glucosinolates in broccoli, broccoli sprouts, brussels sprouts, and cauliflower by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry [J].
Tian, QG ;
Rosselot, RA ;
Schwartz, SJ .
ANALYTICAL BIOCHEMISTRY, 2005, 343 (01) :93-99
[30]   Chemical composition of the volatile extracts from Brassica oleracea L. var. botrytis "Romanesco' cauliflower seeds [J].
Valette, L ;
Fernandez, X ;
Poulain, S ;
Lizzani-Cuvelier, L ;
Loiseau, AM .
FLAVOUR AND FRAGRANCE JOURNAL, 2006, 21 (01) :107-110