首页|Noncanonical Strigolactone Analogues Highlight Selectivity for Stimulating Germination in Two Phelipanche ramosa Populations

Noncanonical Strigolactone Analogues Highlight Selectivity for Stimulating Germination in Two Phelipanche ramosa Populations

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  • NSTL
  • Amer Chemical Soc
Strigolactones (SLs) are plant hormones exuded in the rhizosphere with a signaling role for the development of arbuscular mycorrhizal (AM) fungi and as stimulants of seed germination of the parasitic weeds Orobanche, Phelipanche, and Striga, the most threatening weeds of major crops worldwide. Phelipanche ramosa is present mainly on rape, hemp, and tobacco in France. P. ramosa 2a preferentially attacks hemp, while P. ramosa 1 attacks rapeseed. The recently isolated cannalactone (14) from hemp root exudates has been characterized as a noncanonical SL that selectively stimulates the germination of P. ramosa 2a seeds in comparison with P. ramosa 1. In the present work, (?)-solanacol (5), a canonical orobanchol-type SL exuded by tobacco and tomato, was established to possess a remarkable selective germination stimulant activity for P. ramosa 2a seeds. Two cannalactone analogues, named (±)-SdL19 and (±)-SdL118, have been synthesized. They have an unsaturated acyclic carbon chain with a tertiary hydroxy group and a methyl or a cyclopropyl group instead of a cyclohexane A-ring, respectively. (±)-SdL analogues are able to selectively stimulate P. ramosa 2a, revealing that these minimal structural elements are key for this selective bioactivity. In addition, (±)-SdL19 is able to inhibit shoot branching in Pisum sativum and Arabidopsis thaliana and induces hyphal branching in the AM fungus Rhizophagus irregularis, like SLs.

Taulera Quentin、Andna Lucile、Miesch Laurence、Rochange Soizic、Pouvreau Jean-Bernard、Boyer Franc?ois-Didier、Fornier Suzanne Daignan、de Saint Germain Alexandre、Retailleau Pascal、Pillot Jean-Paul

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Universite? de Toulouse, CNRS, UPS, Toulouse INP

Universite? de Strasbourg, Institut de Chimie, UMR 7177, E?quipe Synthe?se Organique et Phytochimie

Nantes Universite?, CNRS, US2B, UMR 6286

Universite? Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301

Universite? Paris-Saclay, INRAE, AgroParisTech, Institut Jean-Pierre Bourgin (IJPB)

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2022

10.1021/acs.jnatprod.2c00282

Journal of natural products

Journal of natural products

CCR
ISSN：0163-3864
年,卷(期)：2022.85(8)
  • 3
  • 89