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从青霉属中鉴定并阐明 Janthitrems A 和 D 的结构,以及测定 Janthitrems A 和 B 的震颤原性和抗昆虫活性。

Identification and Structure Elucidation of Janthitrems A and D from Penicillium janthinellum and Determination of the Tremorgenic and Anti-Insect Activity of Janthitrems A and B.

机构信息

AgResearch Ltd., Ruakura Research Centre , Private Bag 3123 , Hamilton 3240 , New Zealand.

National Research Council Canada , 1411 Oxford Street , Halifax , NS B3H 3ZI , Canada.

出版信息

J Agric Food Chem. 2018 Dec 19;66(50):13116-13125. doi: 10.1021/acs.jafc.8b04964. Epub 2018 Dec 7.

DOI:10.1021/acs.jafc.8b04964
PMID:30482018
Abstract

New compounds, 11,12-epoxyjanthitrem B (1) and 11,12-epoxyjanthitrem C (4), were isolated from Penicillium janthinellum and given the trivial names janthitrem A and janthitrem D, respectively. The known compounds janthitrem B (2) and janthitrem C (3) were also isolated, and NMR assignments were made for all four compounds. This showed that the previously published NMR assignments for 3 needed considerable revision. 1 and 2 were used as model compounds for the more complex, and highly unstable, epoxyjanthitrems that have been isolated from perennial ryegrass infected with the AR37 endophyte and which contain an epoxide group analogous to that of 1. Both 1 and 2 induced tremors in mice and reduced weight gain and food consumption of porina ( Wiseana cervinata) larvae, although 1 showed greater potency. This shows the importance of the epoxy group and suggests that epoxyjanthitrems are likely to be involved in the observed effects of the AR37 endophyte on livestock and insects.

摘要

从青霉属(Penicillium janthinellum)中分离得到了新化合物 11,12-环氧简亭 B(1)和 11,12-环氧简亭 C(4),并分别将其命名为简亭 A 和简亭 D。还分离得到了已知化合物简亭 B(2)和简亭 C(3),并对所有四个化合物进行了 NMR 归属。这表明先前发表的关于化合物 3 的 NMR 归属需要进行相当大的修正。化合物 1 和 2 被用作模型化合物,用于研究从感染 AR37 内生菌的多年生黑麦草中分离得到的更复杂、高度不稳定的环氧简亭,这些环氧简亭含有与化合物 1 类似的环氧基团。化合物 1 和 2 均能引起小鼠震颤,并降低 Porina(Wiseana cervinata)幼虫的体重增加和食物消耗,尽管化合物 1 表现出更强的活性。这表明环氧基团的重要性,并表明环氧简亭可能参与了 AR37 内生菌对家畜和昆虫的观察到的影响。

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