Antibacterial diterpenes and their fatty acid conjugates from rice leaves

被引:18
作者
Kono, Y [1 ]
Kojima, A
Nagai, R
Watanabe, M
Kawashima, T
Onizawa, T
Teraoka, T
Watanab, M
Koshino, H
Uzawa, J
Suzuki, Y
Sakurai, A
机构
[1] Ibaraki Univ, Sch Agr, Ami, Ibaraki 3000393, Japan
[2] Tokyo Univ Agr & Technol, Fuchu, Tokyo 1838509, Japan
[3] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan
关键词
Oryza sativa; gramineae; rice plant; resistance against Xanthomonas campestris pv. oryzae; antibacterial diterpene; ent-kaurane analogue; myristoyloxy-kaurane; palmitoyloxy-kaurane;
D O I
10.1016/j.phytochem.2004.03.016
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
Six structurally oryzalide-related compounds, oryzadione (1), 2, 3, 4, 5 and 6, were isolated from a neutral fraction of the extract of healthy leaves using a bacterial leaf blight-resistant cultivar of a rice plant, "Norin-27", as a group of antimicrobial substances. Their structures were determined by spectroscopic studies to be kaurane analogues and kaurane analogues conjugated with fatty acids, i.e., 1: ent-15,16-epoxy-kauran-2,3-dione (enol form: ent-15,16-epoxy-2-hydroxy-kauran-1-en-3-one), 2: ent-15,16-epoxy-3beta-hydroxy-kauran-2-one, 3: ent-15,16-epoxy-3-oxa-kauran-2-one, 4: ent-15,16-epoxy-3beta-myristoyloxy-kauran-2-one, 5: ent-15, 16-epoxy-3alpha-palmitoyloxy-kauran-2-one, and 6: ent-15,16-epoxy-2beta-palmitoyloxy-kauran-2-one. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1291 / 1298
页数:8
相关论文
共 7 条
[1]   STRUCTURES OF ORYZALIDE-A AND ORYZALIDE-B, AND ORYZALIC ACID-A, A GROUP OF NOVEL ANTIMICROBIAL DITERPENES, ISOLATED FROM HEALTHY LEAVES OF A BACTERIAL LEAF BLIGHT-RESISTANT CULTIVAR OF RICE PLANT [J].
KONO, Y ;
UZAWA, J ;
KOBAYASHI, K ;
SUZUKI, Y ;
URAMOTO, M ;
SAKURAI, A ;
WATANABE, M ;
TERAOKA, T ;
HOSOKAWA, D ;
WATANABE, M ;
KONDO, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (03) :803-811
[2]  
NAKANISHI K, 1977, Annals of the Phytopathological Society of Japan, V43, P449
[3]  
NAKANISHI K, 1977, Annals of the Phytopathological Society of Japan, V43, P265, DOI 10.3186/jjphytopath.43.265
[4]   NOVEL C-19-KAURANE TYPE OF DITERPENE (ORYZALIDE-A), A NEW ANTIMICROBIAL COMPOUND ISOLATED FROM HEALTHY LEAVES OF A BACTERIAL LEAF BLIGHT-RESISTANT CULTIVAR OF RICE PLANT [J].
WATANABE, M ;
SAKAI, Y ;
TERAOKA, T ;
ABE, H ;
KONO, Y ;
UZAWA, J ;
KOBAYASHI, K ;
SUZUKI, Y ;
SAKURAI, A .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (04) :1103-1105
[5]   STRUCTURES OF ORYZALIC ACID-B AND 3 RELATED-COMPOUNDS, A GROUP OF NOVEL ANTIBACTERIAL DITERPENES, ISOLATED FROM LEAVES OF A BACTERIAL LEAF BLIGHT-RESISTANT CULTIVAR OF RICE [J].
WATANABE, M ;
KONO, Y ;
WATANABE, M ;
UZAWA, J ;
TERAOKA, T ;
HOSOKAWA, D ;
SUZUKI, Y ;
SAKURAI, A ;
TERAGUCHI, M .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (01) :113-117
[6]   Studies on a quantitative analysis of oryzalides and oryzalic acids in rice plants by GC-SIM [J].
Watanabe, M ;
Kono, Y ;
Esumi, Y ;
Teraoka, T ;
Hosokawa, D ;
Suzuki, Y ;
Sakurai, A ;
Watanabe, M .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1996, 60 (09) :1460-1463
[7]  
WATANABE M, 1976, Annals of the Phytopathological Society of Japan, V42, P295, DOI 10.3186/jjphytopath.42.295