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,Journal of Agricultural and Food Chemistry

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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
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2018-11-28 00:00:00 , DOI: 10.1021/acs.jafc.8b04964
Jacob V. Babu ₁ , Alison J. Popay ₁ , Christopher O. Miles _{1,

2} , Alistair L. Wilkins ₃ , Margaret E. di Menna ₁ , Sarah C. Finch ₁

Affiliation

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.

中文翻译：

青霉菌中Janthitrems A和D的鉴定，结构鉴定以及Janthitrems A和B的致震性和抗虫活性的测定

从青霉菌中分离出新的化合物11,12-环氧janthitrem B（1）和11,12-环氧janthitrem C（4），并分别命名为janthitrem A和janthitremD。还分离了已知的化合物janthitrem B（2）和jananthitrem C（3），并对所有四种化合物进行了NMR分配。这表明先前公布的3的NMR分配需要大量修订。1和2用作较复杂和高度不稳定的环氧菊酯的模型化合物，这些化合物已从感染AR37内生菌的多年生黑麦草中分离出来，并含有类似于1的环氧基。既1级2在小鼠和减少体重增加和porina的食物消耗诱导的震颤（Wiseana cervinata）幼虫，虽然1表现出更大的效能。这表明了环氧基的重要性，并表明环氧菊酯可能参与了AR37内生菌对牲畜和昆虫的影响。

更新日期：2018-11-28

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