Metabolism of Chiral Ionylideneacetic Acids on the Abscisic Acid Biosynthetic Pathway in<i>Cercospora</i>

Yamamoto, Hirotaka; Inomata, Masahiro; Tsuchiya, Shinobu; Nakamura, Makoto; Oritani, Takayuki

doi:10.1271/bbb.64.2644

Cited by 13 publications

(10 citation statements)

References 21 publications

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“…Additionally, after a series of reactions of cyclization, isomerization, desaturation and hydroxylation from FPP, ABA is synthesized [13,14]. However different species employ different biosynthetic intermediates.…”

Section: Introductionmentioning

confidence: 99%

Sequencing and Transcriptional Analysis of the Biosynthesis Gene Cluster of Abscisic Acid-Producing Botrytis cinerea

Gong

Shu

Yang

et al. 2014

IJMS

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Botrytis cinerea is a model species with great importance as a pathogen of plants and has become used for biotechnological production of ABA. The ABA cluster of B. cinerea is composed of an open reading frame without significant similarities (bcaba3), followed by the genes (bcaba1 and bcaba2) encoding P450 monooxygenases and a gene probably coding for a short-chain dehydrogenase/reductase (bcaba4). In B. cinerea ATCC58025, targeted inactivation of the genes in the cluster suggested at least three genes responsible for the hydroxylation at carbon atom C-1' and C-4' or oxidation at C-4' of ABA. Our group has identified an ABA-overproducing strain, B. cinerea TB-3-H8. To differentiate TB-3-H8 from other B. cinerea strains with the functional ABA cluster, the DNA sequence of the 12.11-kb region containing the cluster of B. cinerea TB-3-H8 was determined. Full-length cDNAs were also isolated for bcaba1, bcaba2, bcaba3 and bcaba4 from B. cinerea TB-3-H8. Sequence comparison of the four genes and their flanking regions respectively derived from B. cinerea TB-3-H8, B05.10 and T4 revealed that major variations were located in intergenic sequences. In B. cinerea TB-3-H8, the expression profiles of the four function genes under ABA high-yield conditions were also analyzed by real-time PCR.

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Section: Introductionmentioning

confidence: 99%

Sequencing and Transcriptional Analysis of the Biosynthesis Gene Cluster of Abscisic Acid-Producing Botrytis cinerea

Gong

Shu

Yang

et al. 2014

IJMS

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“…The 1 H-NMR spectrum of 4 displayed three methyl singlets at δ 0.99 (3H, CH 3 -14), 1.04 (3H, CH 3 -15) and 2.12 (3H, CH 3 -12); three mutually coupled methylene groups at δ 1.35 (2H, m, CH 2 -2), 1.52 (2H, m, CH 2 -2) and 2.07 (2H, m, CH 2 -2); three olefinic protons at δ 4.53 (1H, br s, H-13a), 4.81 (1H, br s, H-13b) and 5.95 (1H, s, H-10), respectively. In addition, three methine protons at δ 1.59 (1H, d, J = 8.0 Hz, H-6), 2.92 (1H, dd, J = 8.0, 1.9 Hz, H-7) and 3.04 (1H, br s, H-8), along with the 13 C-NMR signals of two sets of carbon-carbon double bond at δ 109.0 (C-13), 115.1 (C-10), 147.7 (C-5) and 157.4 (C-9); two oxymethine carbons of one oxirane ring at δ 59.1 (C-8) and 60.3 (C-7); and one carboxylic acidic carbonyl carbon at δ 171.6 (C-11), evidenced the basic skeleton of 4 as γ-ionylideneacetic acid [ 28 ] with oxirane functionality. The 2 J , 3 J -heteronuclear multiple bond correlation (HMBC) correlations ( Figure 3 ) from CH 3 -14 to C-1, -2, -6; from CH 3 -12 to C-8, -9; from H-6 to C-1, -5, -7; from H-8 to C-7, -9, -10; from H-10 to C-9, -11; and from CH 2 -13 to C-4, -6, respectively, further determined the locations of oxirane and terminal methylene groups to be at C-7/C-8 and C-5.…”

Section: Resultsmentioning

confidence: 99%

“…The UV maxima at 264 nm and IR absorption bands at 3399 and 1686 cm −1 suggested the presence of hydroxyl and α,β-conjugated carbonyl functionalities in 5 . The 1 H and 13 C-NMR spectral characteristics of 5 ( Table 1 and Table 2 ) also constructed the γ-ionylideneacetic acid basic skeleton as shown above [ 28 ]. The 2 J , 3 J -HMBC correlations ( Figure 4 ) from CH 3 -14 to C-1, -2, -6; from CH 3 -12 to C-8, -9, -10; from H-6 to C-1, -5, -8; from H-8 to C-6, -12; from H-10 to C-11, -12; and from CH 2 -13 to C-4, -6, respectively, further determined the locations of hydroxyl and terminal methylene groups to be at C-2 and C-5.…”

Section: Resultsmentioning

confidence: 99%

Hepatoprotective Principles and Other Chemical Constituents from the Mycelium of Phellinus linteus

Huang,

Wang,

Kuo

et al. 2018

Molecules

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In the dimethylnitrosamine (DMN)-induced hepatic fibrosis Wistar rat model, the mycelium extract of Phellinus linteus (PLE) (20 mg/Kg) displayed significant protection against hepatic fibrosis. The present investigation characterized eleven new ionone derivatives, phellinulins D–N (4–14), from the P. linteus mycelium extract and the relative stereochemical structures were constructed according to the spectroscopic and spectrometric analytical results. Some purified compounds were examined for their inhibitory effects on activated rat hepatic stellate cells (HSCs) and several isolates did exhibit significant protection. The results indicated that the mycelium of P. linteus could be explored as a hepatoprotective drug or healthy food candidate in the near future.

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“…In addition, different fungal species employ different biosynthetic intermediates. It has been reported that ABA was synthesized via 1′,4′-dihydroxy-γ-ionylideneacetic acid in Cercospora cruenta 2223, while 1′,4′-trans-diol-ABA was detected as the main ABA intermediate in B. cinerea and Cercospora pini-densiflorae 2124, and 1′-deoxy-ABA was identified as a more important intermediate than 1′,4′-trans-diol-ABA in Cercospora rosicola 25. Therefore, the genes responsible for fungal ABA biosynthesis should be quite distinct from plants.…”

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confidence: 99%

Comparative transcriptome analysis between an evolved abscisic acid-overproducing mutant Botrytis cinerea TBC-A and its ancestral strain Botrytis cinerea TBC-6

Ding

Zhang

Zhong

et al. 2016

Sci Rep

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Abscisic acid (ABA) is a classical phytohormone which plays an important role in plant stress resistance. Moreover, ABA is also found to regulate the activation of innate immune cells and glucose homeostasis in mammals. Therefore, this ‘stress hormone’ is of great importance to theoretical research and agricultural and medical applications. Botrytis cinerea is a well-known phytopathogenic ascomycete that synthesizes ABA via a pathway substantially different from higher plants. Identification of the functional genes involved in ABA biosynthesis in B. cinerea would be of special interest. We developed an ABA-overproducing mutant strain, B. cinerea TBC-A, previously and obtained a 41.5-Mb genome sequence of B. cinerea TBC-A. In this study, the transcriptomes of B. cinerea TBC-A and its ancestral strain TBC-6 were sequenced under identical fermentation conditions. A stringent comparative transcriptome analysis was performed to identify differentially expressed genes participating in the metabolic pathways related to ABA biosynthesis in B. cinerea. This study provides the first global view of the transcriptional changes underlying the very different ABA productivity of the B. cinerea strains and will expand our knowledge of the molecular basis for ABA biosynthesis in B. cinerea.

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Metabolism of Chiral Ionylideneacetic Acids on the Abscisic Acid Biosynthetic Pathway inCercospora

Cited by 13 publications

References 21 publications

Sequencing and Transcriptional Analysis of the Biosynthesis Gene Cluster of Abscisic Acid-Producing Botrytis cinerea

Sequencing and Transcriptional Analysis of the Biosynthesis Gene Cluster of Abscisic Acid-Producing Botrytis cinerea

Hepatoprotective Principles and Other Chemical Constituents from the Mycelium of Phellinus linteus

Comparative transcriptome analysis between an evolved abscisic acid-overproducing mutant Botrytis cinerea TBC-A and its ancestral strain Botrytis cinerea TBC-6

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