Hinokiresinol is not a precursor of agatharesinol in the norlignan biosynthetic pathway in Japanese cedar

The biosynthetic relationship between the two norlignans agatharesinol and trans-hinokiresinol was investigated. Fresh sapwood sticks of Cryptomeria japonica were fed with stable isotope-labeled compounds, namely p-coumaryl alcohol-[9,9-(2)H], p-coumaryl alcohol-[9-(18)O] and trans-hinokiresinol-[1-...

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Veröffentlicht in:Journal of plant physiology. - 1979. - 163(2006), 12 vom: 12. Dez., Seite 1221-8
1. Verfasser: Imai, Takanori (VerfasserIn)
Weitere Verfasser: Nomura, Masaki, Matsushita, Yasuyuki, Fukushima, Kazuhiko
Format: Aufsatz
Sprache:English
Veröffentlicht: 2006
Zugriff auf das übergeordnete Werk:Journal of plant physiology
Schlagworte:Journal Article Research Support, Non-U.S. Gov't Coumaric Acids Lignans Oxygen Isotopes Phenols Propionates agatharesinol hinokiresinol 17676-24-3 mehr... Deuterium AR09D82C7G p-coumaric acid IBS9D1EU3J
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245 1 0 |a Hinokiresinol is not a precursor of agatharesinol in the norlignan biosynthetic pathway in Japanese cedar 
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520 |a The biosynthetic relationship between the two norlignans agatharesinol and trans-hinokiresinol was investigated. Fresh sapwood sticks of Cryptomeria japonica were fed with stable isotope-labeled compounds, namely p-coumaryl alcohol-[9,9-(2)H], p-coumaryl alcohol-[9-(18)O] and trans-hinokiresinol-[1-(2)H], and then incubated under high-humidity for approximately 20 days, during which the two norlignans were produced simultaneously. While trans-hinokiresinol was strongly deuterium-labeled after feeding with p-coumaryl alcohol-[9,9-(2)H], agatharesinol was only lightly labeled after feeding with either p-coumaryl alcohol-[9,9-(2)H] or -[9-(18)O]. These results suggest that p-coumaryl alcohol, which is a precursor of hinokiresinol, is not involved in the biosynthesis of agatharesinol. Therefore, the norlignan carbon skeleton of agatharesinol must be framed from different types of phenylpropanoid monomers compared to those utilized by the trans-hinokiresinol pathway. The biosynthesis of these two norlignans seems to branch at an early stage, i.e., before the framing of the norlignan carbon skeleton. Furthermore, agatharesinol was not labeled with deuterium after feeding with (2)H-labeled trans-hinokiresinol, which has the simplest norlignan structure. This result strongly supports the suggestion that the conversion of trans-hinokiresinol to agatharesinol is not part of the biosynthesis of norlignans and that early branching occurs instead 
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700 1 |a Matsushita, Yasuyuki  |e verfasserin  |4 aut 
700 1 |a Fukushima, Kazuhiko  |e verfasserin  |4 aut 
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