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利用米曲霉异源表达对来自柄曲霉的具有C端甲基转移酶结构域的非还原型聚酮合酶进行产物鉴定

Product identification of non-reducing polyketide synthases with C-terminus methyltransferase domain from Talaromyces stipitatus using Aspergillus oryzae heterologous expression.

作者信息

Hashimoto Makoto, Wakana Daigo, Ueda Miki, Kobayashi Daisuke, Goda Yukihiro, Fujii Isao

机构信息

School of Pharmacy, Iwate Medical University, 2-1-1 Nishitokuta, Yahaba, Iwate 028-3694, Japan.

National Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan.

出版信息

Bioorg Med Chem Lett. 2015 Apr 1;25(7):1381-4. doi: 10.1016/j.bmcl.2015.02.057. Epub 2015 Feb 28.

DOI:10.1016/j.bmcl.2015.02.057
PMID:25770780
Abstract

Talaromyces stipitatus ATCC 10500 possesses 17 non-reducing polyketide synthase (NR-PKS) genes. During the course of our functional analysis of PKS genes with a C-terminus methyltransferase domain from T. stipitatus, we expressed tspks2, tspks3 and tspks4 genes in the heterologous host Aspergillus oryzae, respectively. Although the tspks4 transformant gave no apparent product in HPLC analysis, a novel azaphilone pentaketide (3) was identified along with two known related products from the tspks2 transformant. Of four hexaketide products from the tspks3 transformant, two new compounds were identified to be 2-acetyl-7-methyl-3,6,8-trihydroxynaphthalene (4) and its derivative fused with α-methyl-α,β-unsaturated γ-lactone (7).

摘要

柄孢壳菌ATCC 10500拥有17个非还原型聚酮合酶(NR-PKS)基因。在我们对柄孢壳菌中具有C端甲基转移酶结构域的PKS基因进行功能分析的过程中,我们分别在异源宿主米曲霉中表达了tspks2、tspks3和tspks4基因。尽管tspks4转化体在HPLC分析中未产生明显产物,但从tspks2转化体中鉴定出了一种新的氮杂蒽酮五酮(3)以及两种已知的相关产物。在tspks3转化体的四种六酮产物中,鉴定出两种新化合物为2-乙酰基-7-甲基-3,6,8-三羟基萘(4)及其与α-甲基-α,β-不饱和γ-内酯融合的衍生物(7)。

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引用本文的文献

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RSC Adv. 2020 Mar 10;10(17):10197-10220. doi: 10.1039/d0ra00894j. eCollection 2020 Mar 6.
2
Identification of a putative polyketide synthase gene involved in usnic acid biosynthesis in the lichen Nephromopsis pallescens.鉴定参与地衣 Nephromopsis pallescens 中 usnic 酸生物合成的假定聚酮合酶基因。
PLoS One. 2018 Jul 18;13(7):e0199110. doi: 10.1371/journal.pone.0199110. eCollection 2018.
3
Use of a biosynthetic intermediate to explore the chemical diversity of pseudo-natural fungal polyketides.
利用生物合成中间体探索假天然真菌聚酮化合物的化学多样性。
Nat Chem. 2015 Sep;7(9):737-43. doi: 10.1038/nchem.2308. Epub 2015 Aug 3.
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Synthetic biology of fungal natural products.真菌天然产物的合成生物学
Front Microbiol. 2015 Jul 30;6:775. doi: 10.3389/fmicb.2015.00775. eCollection 2015.