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确证水稻和烟草产生的独脚金内酯的立体化学结构。

Confirming stereochemical structures of strigolactones produced by rice and tobacco.

机构信息

Weed Science Center, Utsunomiya University, 350 Mine-machi, Utsunomiya 321-8505, Japan.

出版信息

Mol Plant. 2013 Jan;6(1):153-63. doi: 10.1093/mp/sss139. Epub 2012 Nov 30.

DOI:10.1093/mp/sss139
PMID:23204500
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3548624/
Abstract

Major strigolactones (SLs) produced by rice (Oryza sativa L. cv. Nipponbare) and tobacco (Nicotiana tabacum L. cv. Michinoku No. 1) were purified and their stereochemical structures were determined by comparing with optically pure synthetic standards for their NMR and CD data and retention times and mass fragmentations in ESI-LC/MS and GC-MS. SLs purified from root exudates of rice plants were orobanchol, orobanchyl acetate, and ent-2'-epi-5-deoxystrigol. In addition to these SLs, 7-oxoorobanchyl acetate and the putative three methoxy-5-deoxystrigol isomers were detected by LC-MS/MS. The production of 7-oxoorobanchyl acetate seemed to occur in the early growth stage, as it was detected only in the root exudates collected during the first week of incubation. The root exudates of tobacco contained at least 11 SLs, including solanacol, solanacyl acetate, orobanchol, ent-2'-epi-orobanchol, orobanchyl acetate, ent-2'-epi-orobanchyl acetate, 5-deoxystrigol, ent-2'-epi-5-deoxystrigol, and three isomers of putative didehydro-orobanchol whose structures remain to be clarified. Furthermore, two sorgolactone isomers but not sorgolactone were detected as minor SLs by LC-MS/MS analysis. It is intriguing to note that rice plants produced only orobanchol-type SLs, derived from ent-2'-epi-5-deoxystrigol, but both orobanchol-type and strigol-type SLs, derived from 5-deoxystrigol were detected in tobacco plants.

摘要

主要的 Strigolactones (SLs) 由水稻(Oryza sativa L. cv. Nipponbare)和烟草(Nicotiana tabacum L. cv. Michinoku No. 1)产生,并通过与光学纯合成标准品的 NMR 和 CD 数据以及电喷雾 LC/MS 和 GC-MS 中的保留时间和质谱碎片进行比较,确定了其立体化学结构。从水稻植株根分泌物中纯化的 SLs 为 Orobanchol、Orobanchyl Acetate 和 Ent-2'-epi-5-deoxystrigol。除了这些 SLs 之外,通过 LC-MS/MS 还检测到 7-氧 Orobanchyl Acetate 和三个可能的三甲氧基-5-去氧 Strigol 异构体。7-氧 Orobanchyl Acetate 的产生似乎发生在早期生长阶段,因为仅在培养的第一周收集的根分泌物中检测到。烟草的根分泌物至少含有 11 种 SLs,包括 Solanacol、Solanacyl Acetate、Orobanchol、Ent-2'-epi-Orobanchol、Orobanchyl Acetate、Ent-2'-epi-Orobanchyl Acetate、5-去氧 Strigol、Ent-2'-epi-5-去氧 Strigol 和三个结构尚未澄清的假定去氢 Orobanchol 异构体。此外,通过 LC-MS/MS 分析还检测到两个 Sorgolactone 异构体,但不是 Sorgolactone,它们是次要的 SLs。值得注意的是,水稻植株仅产生来源于 Ent-2'-epi-5-去氧 Strigol 的 Orobanchol 型 SLs,但在烟草植株中检测到来源于 5-去氧 Strigol 的 Orobanchol 型和 Strigol 型 SLs。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/cd553054e9c2/mpphys_sss139_f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/362132edcb2c/mpphys_sss139_f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/83a096e810e1/mpphys_sss139_f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/394214294298/mpphys_sss139_f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/c8c46299ddc2/mpphys_sss139_f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/c8c3019a84e6/mpphys_sss139_f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/cd553054e9c2/mpphys_sss139_f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/362132edcb2c/mpphys_sss139_f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/83a096e810e1/mpphys_sss139_f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/394214294298/mpphys_sss139_f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/c8c46299ddc2/mpphys_sss139_f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/c8c3019a84e6/mpphys_sss139_f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/37ad/3548624/cd553054e9c2/mpphys_sss139_f0006.jpg

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