title: Hinokiresinol is not a precursor of agatharesinol in the norlignan biosynthetic pathway in Japanese cedar.
abstract: 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.
authors.affiliation: Laboratory of Biomass Resources Utilization, Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan. takaimai@agr.nagoya-u.ac.jp
authors.forename: Takanori
authors.initials: T
authors.lastname: Imai
authors.forename: Masaki
authors.initials: M
authors.lastname: Nomura
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Matsushita
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Fukushima
mesh_terms: D003373:Coumaric Acids; D032485:Cryptomeria / Q000378:metabolism*; D003903:Deuterium / Q000378:metabolism; D006813:Humidity; D017705:Lignans / Q000096:biosynthesis*; D010103:Oxygen Isotopes / Q000378:metabolism; D010636:Phenols; D018547:Plant Stems / Q000378:metabolism; D011422:Propionates / Q000378:metabolism
chemical_list: D003373:Coumaric Acids; D017705:Lignans; D010103:Oxygen Isotopes; D010636:Phenols; D011422:Propionates; C445733:agatharesinol; C119821:hinokiresinol; D003903:Deuterium; C495469:p-coumaric acid