Chenopodolin: A Phytotoxic Unrearranged ent-Pimaradiene Diterpene Produced by Phoma chenopodicola, a Fungal Pathogen for Chenopodium album Biocontrol

被引：54
作者：
Cimmino, Alessio [1 ]
Andolfi, Anna [1 ]
Zonno, Maria C. [2 ]
Avolio, Fabiana [1 ]
Santini, Antonello [3 ]
Tuzi, Angela [1 ]
Berestetskyi, Alexander [4 ]
Vurro, Maurizio [2 ]
Evidente, Antonio [1 ]
机构：
[1] Univ Naples Federico II, Dipartimento Sci Chim, I-80126 Naples, Italy
[2] CNR, Ist Sci Prod Alimentari, I-70125 Bari, Italy
[3] Univ Naples Federico II, Dipartimento Farm, I-80131 Naples, Italy
[4] Russian Acad Agr Sci, All Russian Inst Plant Protect, St Petersburg 196608, Russia
来源：
JOURNAL OF NATURAL PRODUCTS | 2013年 / 76卷 / 07期
关键词：
F-SP CUPRESSI; RICE BLAST LEAVES; ASCOCHYTA-CAULINA; IN-VITRO; PIMARANE DITERPENES; PYRICULARIA-ORYZAE; ORYZALEXIN-A; SPHAEROPSIDINS; ASCAULITOXIN; DERIVATIVES;
D O I：
10.1021/np400218z
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
A new phytotoxic unrearranged ent-pimaradiene diterpene, named chenopodolin, was isolated from the liquid culture of Phoma chenopodicola, a fungal pathogen proposed for the biological control of Chenopodium album, a common worldwide weed of arable crops such as sugar beet and maize. The structure of chenopodolin was established by spectroscopic, X-ray, and chemical methods as (1S,2S,3S,4S,5S,9R,10S,12S,13S)-1,12-acetoxy-2,3-hydroxy-6-oxopimara-7-(8),15-dien-18-oic acid 2,18-lactone. At a concentration of 2 mg/mL, the toxin caused necrotic lesions on Mercurialis annua, Cirsium arvense, and Setaria viride. Five derivatives were prepared by chemical modification of chenopodolin ftuictionalities, and some structure-activity relationships are discussed.
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页码：1291 / 1297
页数：7
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