Chemical identification of 18-hydroxycarlactonoic acid as an LjMAX1 product and in planta conversion of its methyl ester to canonical and non-canonical strigolactones in Lotus japonicus

Mori, Narumi; Sado, Aika; Xie, Xiaonan; Yoneyama, Kaori; Asami, Kei; Seto, Yoshiki; Nomura, T.; Yamaguchi, Shinjiro; Yoneyama, Koichi; Akiyama, Kazuo

doi:10.1016/j.phytochem.2020.112349

Cited by 34 publications

(24 citation statements)

References 47 publications

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“…46) Recently, another clade of cytochrome P450 CYP722C functioning downstream of MAX1 was shown to directly convert CLA to orobanchol, presumably via 18-HO-CLA, although formation of the B/C ring structure with the recombinant enzyme was not stereoselective. 47) In birdsfoot trefoil (Lotus japonicus), 18-HO-CLA has been detected as an endogenous compound 48) and also in other plant species (K. Yoneyama, unpublished data). These results clearly indicate that the biosynthesis from β-carotene to CLA is a common pathway for SLs but further steps after formation of CLA may differ with each plant species and thus with each SL.…”

Section: Biosynthetic Pathway Of Slsmentioning

confidence: 99%

Recent progress in the chemistry and biochemistry of strigolactones

Yoneyama

2020

J. Pestic. Sci.

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Strigolactones (SLs) are plant secondary metabolites derived from carotenoids. SLs play important roles in the regulation of plant growth and development in planta and coordinate interactions between plants and other organisms including root parasitic plants, and symbiotic and pathogenic microbes in the rhizosphere. In the 50 years since the discovery of the first SL, strigol, our knowledge about the chemistry and biochemistry of SLs has advanced explosively, especially over the last two decades. In this review, recent advances in the chemistry and biology of SLs are summarized and possible future outcomes are discussed.

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Section: Biosynthetic Pathway Of Slsmentioning

confidence: 99%

Recent progress in the chemistry and biochemistry of strigolactones

Yoneyama

2020

J. Pestic. Sci.

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“…Canonical SLs are further divided intostrigol‐ and orobanchol‐type, according to the stereochemistry of asymmetric carbon atoms at C3a and C8b: C3a R and C8b S configuration in strigol‐type SLs, including 5‐deoxystrigol (5DS, 18 ) and its derivatives, such as strigol ( 19 ), strigyl acetate ( 20 ), strigone ( 21 ), sorgolactone ( 22 ), sorgomol ( 23 ), ent ‐2′‐ epi ‐orobanchol ( 24 ) and ent ‐2′‐ epi ‐orobanchol acetate ( 25 ), and C3a S and C8b R configuration in orobanchol‐type SLs such as 4‐deoxyorobanchol (4DO, 26 ) and 4DO derivatives, including orobanchol ( 27 ), 7‐hydroxyorobanchol ( 28 ), orobanchyl acetate ( 29 ), 7‐OXO‐orobanchol ( 30 ), 7‐hydroxyorobanchyl acetate ( 31 ), 7‐OXO‐orobanchyl acetate ( 32 ), fabacol ( 33 ), fabacyl acetate ( 34 ), solanacol ( 35 ) and solanacyl acetate ( 36 ) (Yokota et al ., 1998; Xie et al ., 2008; Ueno et al ., 2011; Kohlen et al ., 2012; Kisugi et al ., 2013; Kohlen et al ., 2013; Xie et al ., 2013; Xie, 2016). Non‐canonical SLs with a β‐ionone ring (A ring), including carlactone (CL, 5 ), carlactonic acid (CLA, 6 ), hydroxyl CLs (i.e., 3‐OH‐CL [ 14 ] and 4‐OH‐CL [ 10 ]), hydroxyl CLA (i.e., 18‐OH‐CLA [ 11 ]), methyl carlactonoate (MeCLA, 7 ) and its derivatives (i.e., 18‐OH‐MeCLA [ 12 ], 1″‐OH‐MeCLA [ 8 ], and heliolactone [ 9 ]) have been identified in plants (Baz et al ., 2018; Iseki et al ., 2018; Mori et al ., 2020). In addition, plants produce several non‐canonical SLs with higher structural complexity, for example, Avenaol ( 17 ), Lotuslactone ( 13 ), Zealactone ( 15 ) and Zeapyranolactone ( 16 ) (Charnikhova et al ., 2017, 2018).…”

Section: Sl Functions and Biosynthesismentioning

confidence: 99%

“…MeCLA ( 7 ) is also the precursor of heliolactone ( 9 ), a non‐canonical SL formed in sunflower (Iseki et al ., 2018). It was shown that Lotus japonicus MAX1 ( Lj MAX1/CYP711A9) expressed in yeast microsomes can convert CL ( 5 ) into 18‐OH‐CLA ( 11 ) via the intermediate CLA ( 6 ) (Mori et al ., 2020). Moreover, feeding experiments indicated that 18‐OH‐MeCLA ( 12 ) is transformed to the canonical SL 5DS ( 18 ), directly or via 18‐OH‐CLA ( 11 ) as an intermediate, and to the non‐canonical SL lotuslactone ( 13 ) in L. japonicus (Zhang et al ., 2014; Yoneyama et al ., 2018).…”

Section: Sl Functions and Biosynthesismentioning

confidence: 99%

Plant apocarotenoids: from retrograde signaling to interspecific communication

et al. 2021

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Summary Carotenoids are isoprenoid compounds synthesized by all photosynthetic and some non‐photosynthetic organisms. They are essential for photosynthesis and contribute to many other aspects of a plant's life. The oxidative breakdown of carotenoids gives rise to the formation of a diverse family of essential metabolites called apocarotenoids. This metabolic process either takes place spontaneously through reactive oxygen species or is catalyzed by enzymes generally belonging to the CAROTENOID CLEAVAGE DIOXYGENASE family. Apocarotenoids include the phytohormones abscisic acid and strigolactones (SLs), signaling molecules and growth regulators. Abscisic acid and SLs are vital in regulating plant growth, development and stress response. SLs are also an essential component in plants’ rhizospheric communication with symbionts and parasites. Other apocarotenoid small molecules, such as blumenols, mycorradicins, zaxinone, anchorene, β‐cyclocitral, β‐cyclogeranic acid, β‐ionone and loliolide, are involved in plant growth and development, and/or contribute to different processes, including arbuscular mycorrhiza symbiosis, abiotic stress response, plant–plant and plant–herbivore interactions and plastid retrograde signaling. There are also indications for the presence of structurally unidentified linear cis‐carotene‐derived apocarotenoids, which are presumed to modulate plastid biogenesis and leaf morphology, among other developmental processes. Here, we provide an overview on the biology of old, recently discovered and supposed plant apocarotenoid signaling molecules, describing their biosynthesis, developmental and physiological functions, and role as a messenger in plant communication.

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“…Furthermore, GaCYP722C was shown to catalyze the reaction from CLA to 5‐deoxystrigol (5DS), a strigol‐type canonical SL, in cotton ( Gossypium arboreum ) (Wakabayashi et al ., 2020). Moreover, in Lotus japonicus , LjCYP722C was proposed to function in 5DS biosynthesis downstream of CYP711A9/LjMAX1, which produces 18‐hydroxy‐CLA via CLA (Mori et al ., 2020a; Mori et al ., 2020b). Future analysis of CYP722Cs from various plants will give us clues to understand the diversity of canonical SLs and their biological functions.…”

Section: Sl Biosynthesismentioning

confidence: 99%

“…In L. japonicus , it was recently shown that 18‐hydroxy‐MeCLA, which is likely produced from MeCLA or 18‐hydroxy‐CLA, was converted to lotuslactone (Mori et al ., 2020b). This finding supports the idea that MeCLA and its derivatives are probable precursors of non‐canonical SLs.…”

Section: Sl Biosynthesismentioning

confidence: 99%

Strigolactone biosynthesis, transport and perception

2020

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Summary Strigolactones (SLs) are plant hormones that regulate diverse developmental processes and environmental responses. They are also known to be root‐derived chemical signals that regulate symbiotic and parasitic interactions with arbuscular mycorrhizal fungi and root parasitic plants, respectively. Since the discovery of the hormonal function of SLs in 2008, there has been much progress in the SL research field. In particular, a number of breakthroughs have been achieved in our understanding of SL biosynthesis, transport and perception. The discovery of the hormonal function of SL was quite valuable not only as the identification of a new class of plant hormones, but also as the discovery of the long‐sought‐after SL biosynthetic and response mutants. These mutants in several plant species provided us the genetic resources to address fundamental questions regarding SL biosynthesis and perception. Such mutants were further characterized later, and biochemical analyses of these genetically identified factors have uncovered the outline of SL biosynthesis and perception so far. Moreover, new genes involved in SL transport have been discovered through reverse genetic analyses. In this review, we summarize recent advances in SL research with a focus on biosynthesis, transport and perception.

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Chemical identification of 18-hydroxycarlactonoic acid as an LjMAX1 product and in planta conversion of its methyl ester to canonical and non-canonical strigolactones in Lotus japonicus

Cited by 34 publications

References 47 publications

Recent progress in the chemistry and biochemistry of strigolactones

Recent progress in the chemistry and biochemistry of strigolactones

Plant apocarotenoids: from retrograde signaling to interspecific communication

Strigolactone biosynthesis, transport and perception

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