Ecological Roles of Tryptanthrin, Indirubin and N-Formylanthranilic Acid in Isatis indigotica: Phytoalexins or Phytoanticipins?

被引:9
作者
Pedras, M. Soledade C. [1 ]
Abdoli, Abbas [1 ]
To, Q. Huy [1 ]
Thapa, Chintamani [1 ]
机构
[1] Univ Saskatchewan, Dept Chem, 110 Sci Pl, 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
Brassicaceae; Isatis indigotica; alkaloid; antifungal activity; bioactive compounds; crucifer; isotopic labeling; phytoalexin; phytoanticipin; METABOLIC PRODUCTS; BIOSYNTHESIS; MICROORGANISMS; IDENTIFICATION; NASTURLEXINS; ALKALOIDS; SHIKIMATE; DEFENSES; INDOLES;
D O I
10.1002/cbdv.201800579
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
Leaves of the plant species Isatis indigotica Fortune ex Lindl. (Chinese woad) produce the metabolites tryptanthrin, indirubin and N-formylanthranilic acid upon spraying with an aqueous solution of copper chloride but not after spraying with water. The antifungal activities of these metabolites against the phytopathogens Alternaria brassicicola, Leptosphaeria maculans and Sclerotinia sclerotiorum established that tryptanthrin is a much stronger growth inhibitor of L. maculans than the phytoalexin camalexin. The biosynthetic precursors of tryptanthrin and N-formylanthranilic acid are proposed based on the deuterium incorporations of isotopically labeled compounds. The overall results suggest that tryptanthrin is a phytoalexin and indirubin and N-formylanthranilic acid are phytoanticipins in the plant species I. indigotica and that chemical diversity and biodiversity are intimately connected.
引用
收藏
页数:11
相关论文
共 31 条
[1]   Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine [J].
Adachi, J ;
Mori, Y ;
Matsui, S ;
Takigami, H ;
Fujino, J ;
Kitagawa, H ;
Miller, CA ;
Kato, T ;
Saeki, K ;
Matsuda, T .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (34) :31475-31478
[2]   Systematics and phylogeny of the Brassicaceae (Cruciferae): an overview [J].
Al-Shehbaz, I. A. ;
Beilstein, M. A. ;
Kellogg, E. A. .
PLANT SYSTEMATICS AND EVOLUTION, 2006, 259 (2-4) :89-120
[3]   Silica supported perchloric acid catalyzed rapid N-formylation under solvent-free conditions [J].
Ansari, Mohd Imran ;
Hussain, Mohd Kamil ;
Yadav, Nisha ;
Gupta, Puneet K. ;
Hajela, K. .
TETRAHEDRON LETTERS, 2012, 53 (16) :2063-2065
[4]  
Bailey J. A., 1982, PHYTOALEXINS
[5]   METABOLIC PRODUCTS OF MICROORGANISMS .156. SYNTHESIS AND BIOSYNTHESIS OF SUBSTITUTED TRYPTANTHRINS [J].
FIEDLER, E ;
FIEDLER, HP ;
GERHARD, A ;
KELLERSCHIERLEIN, W ;
KONIG, WA ;
ZAHNER, H .
ARCHIVES OF MICROBIOLOGY, 1976, 107 (03) :249-256
[6]   BIODEGRADATION OF THE INDOLIC SYSTEM OF GRAMINE IN HORDEUM-VULGARE [J].
GHINI, AA ;
BURTON, G ;
GROS, EG .
PHYTOCHEMISTRY, 1991, 30 (03) :779-784
[8]   5-Bromoindirubin 3′-(O-oxiran-2-ylmethyl)oxime: A long-acting anticancer agent and a suicide inhibitor for epoxide hydrolase [J].
Ichimaru, Yoshimi ;
Fujii, Takeshi ;
Saito, Hiroaki ;
Sano, Makoto ;
Uchiyama, Taketo ;
Miyairi, Shinichi .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (17) :4665-4676
[9]   Progress in the studies on tryptanthrin, an alkaloid of history [J].
Jahng, Yurngdong .
ARCHIVES OF PHARMACAL RESEARCH, 2013, 36 (05) :517-535
[10]   Recent synthetic and medicinal perspectives of tryptanthrin [J].
Kaur, Ramandeep ;
Manjal, Sundeep Kaur ;
Rawal, Ravindra K. ;
Kumar, Kapil .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (17) :4533-4552