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Lotuslactone, a non-canonical strigolactone from Lotus japonicus
Phytochemistry ( IF 3.8 ) Pub Date : 2019-01-01 , DOI: 10.1016/j.phytochem.2018.10.034
Xiaonan Xie , Narumi Mori , Kaori Yoneyama , Takahito Nomura , Kenichi Uchida , Koichi Yoneyama , Kohki Akiyama

Root exudates from Lotus japonicus were found to contain at least three different hyphal branching-inducing compounds for the arbuscular mycorrhizal (AM) fungus Gigaspora margarita, one of which had been previously identified as (+)-5-deoxystrigol (5DS), a canonical strigolactone (SL). One of the two remaining unknown hyphal branching inducers was purified and named lotuslactone. Its structure was determined as methyl (E)-2-(3-acetoxy-2-hydroxy-7-methyl-1-oxo-1,2,3,4,5,6-hexahydroazulen-2-yl)-3-(((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)acrylate, by 1D and 2D NMR spectroscopy, and HR-ESI- and EI-MS. Although lotuslactone, a non-canonical SL, contains the AB-ring and the enol ether-bridged D-ring, it lacks the C-ring and has a seven-membered cycloheptadiene in the A-ring part as in medicaol, a major SL of Medicago truncatula. Lotuslactone was much less active than 5DS, but showed comparable activity to methyl carlactonoate (MeCLA) in inducing hyphal branching of G. margarita. Other natural non-canonical SLs including avenaol, heliolactone, and zealactone (methyl zealactonoate) were also found to be moderate to weak inducers of hyphal branching in the AM fungus. Lotuslactone strongly elicited seed germination in Phelipanche ramosa and Orobanche minor, but Striga hermonthica seeds were 100-fold less sensitive to this stimulant.

中文翻译:

Lotuslactone,一种来自 Lotus japonicus 的非规范独脚金内酯

发现莲藕的根系分泌物含有至少三种不同的诱导丛枝菌根 (AM) 真菌 Gigaspora margarita 的菌丝分枝化合物,其中一种先前已被鉴定为 (+)-5-deoxystrigol (5DS),一种经典的独脚金内酯 (SL)。剩余的两种未知菌丝分枝诱导剂中的一种被纯化并命名为莲花内酯。其结构确定为甲基 (E)-2-(3-acetoxy-2-hydroxy-7-methyl-1-oxo-1,2,3,4,5,6-hexahydroazulen-2-yl)-3- ((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy) 丙烯酸酯,通过 1D 和 2D NMR 光谱,以及 HR-ESI-和 EI-MS。尽管莲花内酯是一种非经典的 SL,包含 AB 环和烯醇醚桥接的 D 环,但它没有 C 环,并且在 A 环部分具有一个七元环庚二烯,如主要的 SL紫花苜蓿。Lotuslactone 的活性远低于 5DS,但在诱导 G. margarita 菌丝分枝方面显示出与甲基内酯 (MeCLA) 相当的活性。还发现其他天然非规范 SL 包括燕麦醇、太阳内酯和玉米内酯(玉米内酯甲酯)是 AM 真菌菌丝分枝的中度至弱诱导剂。Lotuslactone 强烈引发 Phelipanche ramosa 和 Orobanche minor 的种子萌发,但独脚金种子对这种兴奋剂的敏感性低 100 倍。
更新日期:2019-01-01
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