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Confirming Stereochemical Structures of Strigolactones Produced by Rice and Tobacco

Molecular Plant 2013年第1期6卷 153-163页

作者： Xiaonan Xie Kaori Yoneyama Takaya Kisugi Kenichi Uchida seisuke ito Kohki Akiyama Hideo Hayashi Takao Yokota Takahito Nomura Koichi Yoneyama Weed Science Center Utsunomiya University 350 Mine-machi Utsunomiya 321-8505 Japan Department of Biosciences Faculty of Science and Technology Teikyo University 1-1 Toyosatodai Utsunomiya 320-8851 Japan Graduate School of Life and Environmental Sciences Osaka Prefecture University 1-1 Gakuen-cho Nakaku Sakai Osaka 599-8531 Japan

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-deoxystr- igol. 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.

关键词： germination stimulant Orobanche rice root parasitic plant Striga strigolactone tobacco.

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