Structural diversity of strigolactones and their distribution in the plant kingdom

Xie, Xiaonan

doi:10.1584/jpestics.j16-02

Cited by 71 publications

(59 citation statements)

References 56 publications

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“…SLs are produced and exuded at extremely low quantities, being active at pico‐ to nanomolar concentrations, and have been reported in a variety of plant species (Andreo‐Jimenez et al, ; Delaux et al, ; Xie, ). A single plant species can produce various types of SLs, and even different varieties of the same plant species appear to synthesize a blend of SL molecules in different quantities (Ruyter‐Spira, Al‐Babili, van der Krol, & Bouwmeester, ; Xie, Yoneyama, & Yoneyama, ).…”

Section: Sl Production In Plants Under Abiotic Stressesmentioning

confidence: 99%

“…SLs are mainly produced by the roots, and that their production in the roots is much higher than in the aerial tissues under normal growth conditions (Brewer et al, ; Visentin et al, ; Xie, ; Xie et al, ). In contrast to roots, little and no effects on SL contents were observed in the shoots of L. japonicus and sorghum, respectively, under P‐deficient ( L. japonicus ) or P‐deficient and N‐deficient (sorghum) conditions (Liu et al, ; Yoneyama, Yoneyama, et al, ).…”

Section: Sl Production In Plants Under Abiotic Stressesmentioning

confidence: 99%

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Strigolactones in plant adaptation to abiotic stresses: An emerging avenue of plant research

Mostofa

Nguyen

et al. 2018

Plant Cell & Environment

161

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Phytohormones play central roles in boosting plant tolerance to environmental stresses, which negatively affect plant productivity and threaten future food security. Strigolactones (SLs), a class of carotenoid-derived phytohormones, were initially discovered as an "ecological signal" for parasitic seed germination and establishment of symbiotic relationship between plants and beneficial microbes. Subsequent characterizations have described their functional roles in various developmental processes, including root development, shoot branching, reproductive development, and leaf senescence. SLs have recently drawn much attention due to their essential roles in the regulation of various physiological and molecular processes during the adaptation of plants to abiotic stresses. Reports suggest that the production of SLs in plants is strictly regulated and dependent on the type of stresses that plants confront at various stages of development. Recently, evidence for crosstalk between SLs and other phytohormones, such as abscisic acid, in responses to abiotic stresses suggests that SLs actively participate within regulatory networks of plant stress adaptation that are governed by phytohormones. Moreover, the prospective roles of SLs in the management of plant growth and development under adverse environmental conditions have been suggested. In this review, we provide a comprehensive discussion pertaining to SL-mediated plant responses and adaptation to abiotic stresses.

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Section: Sl Production In Plants Under Abiotic Stressesmentioning

confidence: 99%

Section: Sl Production In Plants Under Abiotic Stressesmentioning

confidence: 99%

Strigolactones in plant adaptation to abiotic stresses: An emerging avenue of plant research

Mostofa

Nguyen

et al. 2018

Plant Cell & Environment

161

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“…Since then, the number of isolated SLs has increased steadily. Today, there are more than 25 known natural SLs (Ćavar, Zwanenburg, & Tarkowski, ; Xie, ) characterized by a common structure consisting of butenolide ring (D‐ring) coupled in R ‐configuration via an ethol ether bridge to a tricyclic lacton (ABC‐ring) in canonical SLs, such as strigol, or to a less conserved moiety in non‐canonical ones (Al‐Babili & Bouwmeester, ; Jia, Baz, & Al‐Babili, ). Stereoconfiguration of the B/C junction, modifications of the ABC ring and structural variations of non‐canonical SLs give rise to the diversity of natural SLs (Al‐Babili & Bouwmeester, ; Jia et al, ; Zwanenburg & Pospíšil, ).…”

Section: Introductionmentioning

confidence: 99%

Suicidal germination as a control strategy for Striga hermonthica (Benth.) in smallholder farms of sub‐Saharan Africa

Kountche

Jamil

Yonli

et al. 2019

Plants People Planet

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Societal Impact Statement Infestation by the parasitic plant Striga hermonthica is a severe threat to food security in sub‐Saharan Africa, impacting the production of the major staple crops pearl millet and sorghum, equating to 7–10 billion $ losses. Using Striga seed dependency on host‐released germination stimulants, we have developed and validated a method for addressing the problem of accumulated parasite seedbanks—the major obstacle in combating Striga infestation in African rain‐fed fields. Application of our method promises to alleviate the problem posed by this pernicious weed by increasing crop production for smallholder farmers. Summary The root parasitic plant Striga hermonthica is a major threat to global food security, causing enormous losses in yields of the main staple crops in sub‐Saharan Africa, which include pearl millet, sorghum, maize and rice. Sustainable Striga control should ideally lead to the depletion of the vast, long‐lived Striga seedbank, and this can be achieved by inducing suicidal seed germination through application of strigolactone (SL) analogs in the absence of host plants. However, this “suicidal germination” strategy has not been evaluated under the natural rain‐fed conditions that prevail in Striga‐prone regions. We have developed and validated a protocol for suicidal germination in laboratory and natural conditions in Striga‐infested rain‐fed African fields. Three SL analogs were tested and these resulted to between 65% and 55% reduction in Striga emergence in pearl millet and sorghum fields, respectively. We conclude that suicidal germination is an effective method for reducing the Striga seedbank. Moreover, the minimal demands of our protocol, in terms of water consumption and amount of selected SL analogs, make it affordable and applicable at a large scale in African rain‐fed agriculture, holding promise for sustainable cleaning of heavily Striga‐infested fields in sub‐Saharan Africa.

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“…Thus, the chemical structure of 1 was determined to be methyl (2E,3E)-4-((R,S)-3,3-dimethyl-2-(3-methylbut-2-en-2-yl)-5-oxotetrahydrofuran-2-yl)-2-((((R)-4-methyl-5-oxo-2,5-dihydrofran-2-yl) oxy) methylene) but-3-enoate, which was named methyl zealactonoate. 6) Although 1 contains only the D-ring moiety of canonical SLs and thus is classified as a non-canonical SL, 2) feeding experiments with 13 C-CL confirmed that 1 is synthesized from CL in maize plants (Supplemental Fig. S7).…”

mentioning

confidence: 87%

“…5) SL1 and SL2 were found to have the molecular weights of 348 and 276, respectively. Herein we report the isolation and structure determination of SL2, named methyl zealactonoate, 6) and its germination stimulation activities on S. hermonthica, Phelipanche ramosa, and Orobanche minor seeds.…”

mentioning

confidence: 99%

Methyl zealactonoate, a novel germination stimulant for root parasitic weeds produced by maize

Xie

Kisugi

Yoneyama

et al. 2017

Journal of Pesticide Science

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One of the germination stimulants for root parasitic weeds produced by maize (Zea mays) was isolated and named methyl zealactonoate (1). Its structure was determined to be methyl (2E,3E)-4-((RS)-3,3-dimethyl-2-(3-methylbut-2-en-2-yl)-5-oxotetrahydrofuran-2-yl)-2-((((R)-4-methyl-5-oxo-2,5-dihydrofran-2-yl)oxy)methylene)but-3-enoate using by 1D and 2D NMR spectroscopy and ESI and EI-MS spectrometry. Feeding experiments with 13 C-carlactone (CL), a biosynthetic intermediate for strigolactones, confirmed that 1 is produced from CL in maize. Methyl zealactonoate strongly elicits Striga hermonthica and Phelipanche ramosa seed germination, while Orobanche minor seeds are 100-fold less sensitive to this stimulant. © Pesticide Science Society of Japan Keywords: maize, strigolactones, germination stimulant, parasitic weeds. Maize (Zea mays) is a major host of the root parasitic weeds known as witchweeds, Striga hermonthica and S. asiatica, and has been reported to produce several strigolactones (SLs). 1,2)Among known SLs, strigol was isolated as the major Striga seed germination stimulant in maize root exudates.3) In addition to this SL, sorgomol and 5-deoxystrigol were found in maize root exudates. 4) Recently, Jamil et al. reported the detection of novel germination stimulants tentatively called SL1 and SL2 in maize root exudates based on LC-MS/MS analysis.5) SL1 and SL2 were found to have the molecular weights of 348 and 276, respectively. Herein we report the isolation and structure determination of SL2, named methyl zealactonoate, 6) and its germination stimulation activities on S. hermonthica, Phelipanche ramosa, and Orobanche minor seeds.The crude EtOAc extract (350.7 mg) of root exudates collected over 5 weeks from ca. 800 maize seedlings grown hydroponically was purified using silica gel column chromatography (CC) with stepwise elution using n-hexane and EtOAc. The 30% and 40% EtOAc fractions which were found via LC-MS analysis to contain SL1 and SL2 were combined and further purified by silica gel CC (25% EtOAc in n-hexane). Since SL1 was found to be a mixture of at least two isomers with very similar chromatographic behaviors, we focused on the purification of SL2. The fractions containing SL2 were combined and purified by HPLC on an ODS column followed by HPLC on an ODS-CN column to afford pure germination stimulant 1 (7.83 mg) as an amorphous solid.The molecular formula of 1 was established to be C 20 H 24 O 7 on the basis of protonated and sodium adduct ions obtained by HR-ESI-TOF-MS, indicative of nine degrees of unsaturation. The molecular ion observed at m/z 376 [M] + in GC-MS also supported this molecular formula.The 1 H NMR spectrum of 1 displayed two singlet methyl protons at 0.73 and 0.99 ppm, two methyl protons with small coupling (<2 Hz) at 1.25 and 1.64 ppm; one oxygenated methyl proton at 3.35 ppm; two geminal coupled methylene protons at 1.90 and 2.25 ppm, five olefinic protons at 4. 71, 4.94, 5.20, 5.53, and 7.45 ppm; and two coupled olefinic protons with 16.75 Hz, suggesting the trans olefin...

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Structural diversity of strigolactones and their distribution in the plant kingdom

Cited by 71 publications

References 56 publications

Strigolactones in plant adaptation to abiotic stresses: An emerging avenue of plant research

Strigolactones in plant adaptation to abiotic stresses: An emerging avenue of plant research

Suicidal germination as a control strategy for Striga hermonthica (Benth.) in smallholder farms of sub‐Saharan Africa

Methyl zealactonoate, a novel germination stimulant for root parasitic weeds produced by maize

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