Title : Lotuslactone, a non-canonical strigolactone from Lotus japonicus - Xie_2019_Phytochemistry_157_200
Author(s) : Xie X , Mori N , Yoneyama K , Nomura T , Uchida K , Akiyama K
Ref : Phytochemistry , 157 :200 , 2019
Abstract :

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.

PubMedSearch : Xie_2019_Phytochemistry_157_200
PubMedID: 30439621

Related information

Inhibitor Avenaol    MeCLA
Substrate Avenaol    MeCLA    MeCLA    Lotuslactone    Zealactone    Heliolactone

Citations formats

Xie X, Mori N, Yoneyama K, Nomura T, Uchida K, Akiyama K (2019)
Lotuslactone, a non-canonical strigolactone from Lotus japonicus
Phytochemistry 157 :200

Xie X, Mori N, Yoneyama K, Nomura T, Uchida K, Akiyama K (2019)
Phytochemistry 157 :200