Purification and Identification of New Acyl-conjugated Teasterones in Lily Pollen

Asakawa, Seiichi; Abé, Hiroshi; Nishikawa, Naoko; Natsume, Masahiro; Koshioka, Masaji

doi:10.1271/bbb.60.1416

Cited by 50 publications

(25 citation statements)

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“…The metabolic processes that inactivate bioactive BRs include dehydrogenation at C-3 and C-23 (Hai et al, 1996;Watanabe et al, 2000), epimerization at C-2, C-3, and C-24 (Suzuki et al, 1993;Nishikawa et al, 1995), hydroxylation at C-20, C-25, and C-26 (Voigt et al, 1993;Kolbe et al, 1996;Yokota et al, 1996), side chain cleavage at C-20/22 (Kolbe et al, 1996), and sulfonation at C-22 (Rouleau et al, 1999). In addition, active BRs are inactivated through conjugation by esterification at C-3 (Kolbe et al, 1995;Asakawa et al, 1996) and glycosylation at C-2, C-3, C-23, C-25, and C-26 (Bajguz, 2007).…”

Section: Bia1 Is a Bahd Acyltransferase-like Protein Involved In The mentioning

confidence: 99%

“…The natural product of an esterified form of BRs, TE-3b-myristate, was isolated from Lilium longiflorum (Asakawa et al, 1994;Soeno et al, 2000). TE3b-laurate was also detected in L. longiflorum (Asakawa et al, 1996). The esterified metabolites also include conjugates of 3,24-diepiCS and 3,24-diepiBL with acyl components, such as laurate, myristate, and palmitate in Ornithopus sativus (Kolbe et al, 1995).…”

Section: Bia1 Is a Bahd Acyltransferase-like Protein Involved In The mentioning

confidence: 99%

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Genetic Evidence for the Reduction of Brassinosteroid Levels by a BAHD Acyltransferase-Like Protein in Arabidopsis

et al. 2012

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Brassinosteroids (BRs) are a group of steroidal hormones involved in plant development. Although the BR biosynthesis pathways are well characterized, the BR inactivation process, which contributes to BR homeostasis, is less understood. Here, we show that a member of the BAHD (for benzylalcohol O-acetyltransferase, anthocyanin O-hydroxycinnamoyltransferase, anthranilate N-hydroxycinnamoyl/benzoyltransferase, and deacetylvindoline 4-O-acetyltransferase) acyltransferase family may play a role in BR homeostasis in Arabidopsis (Arabidopsis thaliana). We isolated two gain-of-function mutants, brassinosteroid inactivator1-1Dominant (bia1-1D) and bia1-2D, in which a novel BAHD acyltransferase-like protein was transcriptionally activated. Both mutants exhibited dwarfism, reduced male fertility, and deetiolation in darkness, which are typical phenotypes of plants defective in BR biosynthesis. Exogenous BR treatment rescued the phenotypes of the bia1-1D mutant. Endogenous levels of BRs were reduced in the bia1-1D mutant, demonstrating that BIA1 regulates endogenous BR levels. When grown in darkness, the bia1 loss-of-function mutant showed a longer hypocotyl phenotype and was more responsive to exogenous BR treatment than the wild-type plant. BIA1 expression was predominantly observed in the root, where low levels of BRs were detected. These results indicate that the BAHD acyltransferase family member encoded by BIA1 plays a role in controlling BR levels, particularly in the root and hypocotyl in darkness. Taken together, our study provides new insights into a mechanism that maintains BR homeostasis in Arabidopsis, likely via acyl conjugation of BRs.

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Section: Bia1 Is a Bahd Acyltransferase-like Protein Involved In The mentioning

confidence: 99%

Section: Bia1 Is a Bahd Acyltransferase-like Protein Involved In The mentioning

confidence: 99%

Genetic Evidence for the Reduction of Brassinosteroid Levels by a BAHD Acyltransferase-Like Protein in Arabidopsis

et al. 2012

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“…Rouleau et al (1999) identified an inducible steroid sulfotransferase (BNST3) in Brassica napus that preferentially sulfonates early BR-biosynthetic intermediates, such as 24-epiCT, at the C-22 hydroxy group. Another possibility is that the pools of 22-OH-3-one and 3-epi-6-deoxoCT may be stabilized by reversible glucosylation or acylation, which have been suggested to regulate TE and BL levels (Asakawa et al, 1996;Poppenberger et al, 2005).…”

Section: Novel C-23 Hydroxylation Shortcutsmentioning

confidence: 99%

C-23 Hydroxylation byArabidopsisCYP90C1 and CYP90D1 Reveals a Novel Shortcut in Brassinosteroid Biosynthesis

et al. 2006

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Brassinosteroids (BRs) are biosynthesized from campesterol via several cytochrome P450 (P450)-catalyzed oxidative reactions. We report the functional characterization of two BR-biosynthetic P450s from Arabidopsis thaliana: CYP90C1/ ROTUNDIFOLIA3 and CYP90D1. The cyp90c1 cyp90d1 double mutant exhibits the characteristic BR-deficient dwarf phenotype, although the individual mutants do not display this phenotype. These data suggest redundant roles for these P450s. In vitro biochemical assays using insect cell-expressed proteins revealed that both CYP90C1 and CYP90D1 catalyze C-23 hydroxylation of various 22-hydroxylated BRs with markedly different catalytic efficiencies. Both enzymes preferentially convert 3-epi-6-deoxocathasterone, (22S,24R)-22-hydroxy-5a-ergostan-3-one, and (22S,24R)-22-hydroxyergost-4-en-3-one to 23-hydroxylated products, whereas they are less active on 6-deoxocathasterone. Likewise, cyp90c1 cyp90d1 plants were deficient in 23-hydroxylated BRs, and in feeding experiments using exogenously supplied intermediates, only 23-hydroxylated BRs rescued the growth deficiency of the cyp90c1 cyp90d1 mutant. Thus, CYP90C1 and CYP90D1 are redundant BR C-23 hydroxylases. Moreover, their preferential substrates are present in the endogenous Arabidopsis BR pool. Based on these results, we propose C-23 hydroxylation shortcuts that bypass campestanol, 6-deoxocathasterone, and 6-deoxoteasterone and lead directly from (22S,24R)-22-hydroxy-5a-ergostan-3-one and 3-epi-6-deoxocathasterone to 3-dehydro-6-deoxoteasterone and 6-deoxotyphasterol.

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“…First, pollen is a rich source of endogenous BRs (25). Second, during lily pollen development, the conjugated teasterone is found at the microspore stage, and its decrease is correlated with the increased level of free BRs (26). Third, experiments with Prunus avium indicated that BRs induce pollen tube elongation (27).…”

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confidence: 99%

Brassinosteroids control male fertility by regulating the expression of key genes involved in Arabidopsis anther and pollen development

Zhu

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

262

195

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The development of anther and pollen is important for male reproduction, and this process is coordinately regulated by many external and internal cues. In this study, we systematically examined the male reproductive phenotypes of a series of brassinosteroid biosynthetic and signaling mutants and found that, besides the expected cell-expansion defects, these mutants also showed reduced pollen number, viability, and release efficiency. These defects were related with abnormal tapetum and microspore development. Using both real-time quantitative RT-PCR and microarray experiments, we found that the expression of many key genes required for anther and pollen development was suppressed in these mutants. ChIP analysis demonstrated that BES1, an important transcription factor for brassinosteroid signaling, could directly bind to the promoter regions of genes encoding transcription factors essential for anther and pollen development, SPL/NZZ, TDF1, AMS, MS1, and MS2. Taken together, these data lead us to propose that brassinosteroids control male fertility at least in part via directly regulating key genes for anther and pollen development in Arabidopsis. Our work provides a unique mechanism to explain how a phytohormone regulates an essential genetic program for plant development.male fertility | regulatory network | signaling | chromatin immunoprecipitation

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Purification and Identification of New Acyl-conjugated Teasterones in Lily Pollen

Cited by 50 publications

References 1 publication

Genetic Evidence for the Reduction of Brassinosteroid Levels by a BAHD Acyltransferase-Like Protein in Arabidopsis

Genetic Evidence for the Reduction of Brassinosteroid Levels by a BAHD Acyltransferase-Like Protein in Arabidopsis

C-23 Hydroxylation byArabidopsisCYP90C1 and CYP90D1 Reveals a Novel Shortcut in Brassinosteroid Biosynthesis

Brassinosteroids control male fertility by regulating the expression of key genes involved in Arabidopsis anther and pollen development

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