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列当醇的结构解析与生物合成

Structure Elucidation and Biosynthesis of Orobanchol.

作者信息

Wakabayashi Takatoshi, Ueno Kotomi, Sugimoto Yukihiro

机构信息

Graduate School of Agricultural Science, Kobe University, Kobe, Japan.

Faculty of Agriculture, Tottori University, Tottori, Japan.

出版信息

Front Plant Sci. 2022 Feb 9;13:835160. doi: 10.3389/fpls.2022.835160. eCollection 2022.

DOI:10.3389/fpls.2022.835160
PMID:35222492
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8863659/
Abstract

Strigolactones (SLs), a class of phytohormones that regulate diverse developmental processes, were initially characterized as host-derived germination stimulants for seeds belonging to the genera , , and . Orobanchol (), which is detected in the root exudates of several plants and recognized as a prevalent SL, was first isolated from the root exudates of red clover as a germination stimulant for in 1998. However, the structure of this stimulant proposed at that time was disputable considering its predicted germination-inducing activity for . The genuine structure of orobanchol was elucidated following a decade-long controversy, which ultimately facilitated the understanding of the importance of SL stereochemistry in seed germination. Recently, studies focusing on clarifying the biosynthesis pathway of orobanchol are being conducted. Cytochrome P450 monooxygenases are involved in orobanchol biosynthesis downstream of carlactonoic acid (CLA) via two pathways: either through 4-deoxyorobanchol or direct conversion from CLA. Substantial progress in the identification of more SL structures and clarification of their biosynthetic mechanisms will further contribute in the comprehension of their structural diversity's functional importance and agricultural applications. Herein, we have reviewed the history leading to the discovery of the genuine structure of orobanchol and the current understanding of its biosynthetic mechanisms.

摘要

独脚金内酯(SLs)是一类调节多种发育过程的植物激素,最初被表征为列当属、独脚金属和百蕊草属种子的宿主衍生萌发刺激物。1998年,从红三叶草的根分泌物中首次分离出一种在几种植物的根分泌物中都能检测到且被认为是一种普遍存在的独脚金内酯——列当醇(orobanchol),它作为一种萌发刺激物可刺激埃及列当种子萌发。然而,考虑到其对列当属种子预测的萌发诱导活性,当时提出的这种刺激物的结构存在争议。经过长达十年的争论,列当醇的真实结构得以阐明,这最终促进了对独脚金内酯立体化学在列当属种子萌发中重要性的理解。最近,人们正在开展专注于阐明列当醇生物合成途径的研究。细胞色素P450单加氧酶通过两条途径参与列当醇在独脚金烯酸(CLA)下游的生物合成:要么通过4-脱氧列当醇,要么直接从CLA转化。在鉴定更多独脚金内酯结构及其生物合成机制的阐明方面取得的实质性进展,将进一步有助于理解其结构多样性的功能重要性和农业应用。在此,我们回顾了导致列当醇真实结构发现的历程以及目前对其生物合成机制的理解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c97/8863659/ff17cce43857/fpls-13-835160-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c97/8863659/b0728aa0e2cf/fpls-13-835160-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c97/8863659/ff17cce43857/fpls-13-835160-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c97/8863659/b0728aa0e2cf/fpls-13-835160-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7c97/8863659/ff17cce43857/fpls-13-835160-g002.jpg

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本文引用的文献

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Sci Adv. 2021 Sep 17;7(38):eabh4048. doi: 10.1126/sciadv.abh4048.
2
Strigolactone biosynthesis catalyzed by cytochrome P450 and sulfotransferase in sorghum.高粱中细胞色素 P450 和磺基转移酶催化的独脚金内酯生物合成。
New Phytol. 2021 Dec;232(5):1999-2010. doi: 10.1111/nph.17737. Epub 2021 Oct 3.
3
CYP722C from Gossypium arboreum catalyzes the conversion of carlactonoic acid to 5-deoxystrigol.陆地棉 CYP722C 催化卡尔拉酮酸转化为 5-脱甲氧基野麦畏。
Global changes in gene expression during compatible and incompatible interactions of faba bean (Vicia faba L.) during Orobanche foetida parasitism.蚕豆(Vicia faba L.)与列当(Orobanche foetida)共生和非共生互作过程中基因表达的全球变化。
PLoS One. 2024 Apr 16;19(4):e0301981. doi: 10.1371/journal.pone.0301981. eCollection 2024.
4
High-density linkage mapping and genetic dissection of resistance to broomrape ( Forsk.) in pea ( L.).豌豆(L.)对列当(Forsk.)抗性的高密度连锁图谱构建与遗传解析
Front Plant Sci. 2023 Jul 10;14:1216297. doi: 10.3389/fpls.2023.1216297. eCollection 2023.
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A Stereoselective Strigolactone Biosynthesis Catalyzed by a 2-Oxoglutarate-Dependent Dioxygenase in Sorghum.高粱中 2- 酮戊二酸依赖的双加氧酶催化的立体选择性独脚金内酯生物合成。
Plant Cell Physiol. 2023 Sep 15;64(9):1034-1045. doi: 10.1093/pcp/pcad060.
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Perspectives on the metabolism of strigolactone rhizospheric signals.独脚金内酯根际信号的代谢研究视角
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The tomato MAX1 homolog, SlMAX1, is involved in the biosynthesis of tomato strigolactones from carlactone.番茄 MAX1 同源物 SlMAX1 参与了从 carlactone 生物合成番茄独脚金内酯的过程。
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