Alexandre Lumbroso

Strigolactone derivatives for potential crop enhancement applications.

New technologies able to mitigate the main abiotic stresses (i.e., drought, salinity, cold and heat) represent a substantial opportunity to contribute to a sustainable increase of agricultural production. In this context, the recently discovered phytohormone strigolactone is an important area of study which can underpin the quest for new anti-stress technologies. The pleiotropic roles played by strigolactones in plant growth/development and in plant adaptation to environmental changes can pave the way for new innovative crop enhancement applications. Although a significant scientific effort has been dedicated to the strigolactone subject, an updated review with emphasis on the crop protection perspective was missing. This paper aims to analyze the advancement in different areas of the strigolactone domain and the implications for agronomical applications.

Zealactones. Novel natural strigolactones from maize

In the root exudate and root extracts of maize hybrid cv NK Falkone seven putative strigolactones were detected using UPLC-TQ-MS-MS. All seven compounds displayed MS-MS-fragmentation common for strigolactones and particularly the presence of a fragment of m/z 97xa0Da, which may indicate the presence of the so-called D-ring, suggests they are strigolactones. The levels of all these putative strigolactones increased upon phosphate starvation and decreased upon fluridone (carotenoid biosynthesis inhibitor) treatment, both of which are a common response for strigolactones. All seven compounds were subsequently isolated with prep-HPLC-MS. They all exhibited Striga hermonthica seed germination inducing activity just as the synthetic strigolactone analog GR24. The structure of two of the seven compounds was elucidated by NMR spectroscopy as: methyl (2E,3E)-4-(3,3-dimethyl-5-oxo-2-(prop-1-en-2-yl)tetrahydrofuran-2-yl)-2-(((4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)methylene)but-3-enoate (two diastereomers 1a and 1b). Strigolactones (1a/b) are closely related to the methyl ester of carlactonoic acid (MeCLA) and heliolactone. However, they contain a unique 4,4-dimethyltetrahydrofuran-2-one motif as the A-ring instead of the classical (di)methylcyclohexene. Because these compounds were isolated from maize (Zea mays) we called them zealactone 1a and 1b. The implications of this discovery for our view on strigolactones and their biosynthesis are discussed.

Stereodivergent synthesis of iminosugars from stannylated derivatives of (S)-vinylglycinol.

An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS configuration depending on the order of the Sn-Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the α-aminoanion intermediate. The dehydropiperidines 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.

Simplified strigolactams as potent analogues of strigolactones for the seed germination induction of Orobanche cumana Wallr

BACKGROUNDnStrigolactones play an important role in the rhizosphere as signalling molecules stimulating the seed germination of parasitic weed seeds and hyphal branching of arbuscular micorrhiza, and also act as hormones in plant roots and shoots. Strigolactone derivatives, e.g. strigolactams, could be used as suicidal germination inducers in the absence of a host crop for the decontamination of land infested with parasitic weed seeds.nnnRESULTSnWe report the stereoselective synthesis of novel strigolactams, together with some of their critical physicochemical properties, such as water solubility, hydrolytic stability, as well as their short soil persistence. In addition, we show that such strigolactams are potent germination stimulants of O. cumana parasitic weed seeds and do not affect the seed germination and the root growth of sunflower.nnnCONCLUSIONSnThe novel strigolactam derivatives described here compare favourably with the corresponding GR-28 strigolactones in terms of biological activity and physicochemical properties. However, we believe strigolactone and strigolactam derivatives require further structural optimisation to improve their soil persistence to demonstrate a potential for agronomical applications.