The model moss Physcomitrella patens and liverwort Marchantia polymorpha possess all enzymatic machinery responsible for the initial stages of jasmonate pathway, including the active 13(S)-lipoxygenase, allene oxide synthase (AOS) and allene oxide cyclase (AOC). At the same time, the jasmonic acid is missing from both P. patens and M. polymorpha. Our GC-MS profiling of oxylipins of P. patens gametophores and M. polymorpha tissues revealed some distinctive peculiarities. The 15(Z)-cis-12-oxo-10,15-phytodienoic acid (12-OPDA) was the major oxylipin in M. polymorpha. In contrast, the 12-OPDA was only a minor constituent in P. patens, while another cyclopentenone 1 was the predominant oxylipin. Product 1 was identified by its MS, 1H-NMR, 1H-1H-COSY, HSQC and HMBC data as 15(Z)-12-oxo-9(13),15-phytodienoic acid, i.e., the iso-12-OPDA. The corresponding C16 homologue, 2,3-dinor-iso-12-OPDA (2), have also been detected as a minor component in P. patens and a prominent product in M. polymorpha. Besides, the 2,3-dinor-cis-12-OPDA (3) was also present in M. polymorpha. Apparently, the malfunction of cyclopentenone reduction by the 12-OPDA reductase in P. patens and (to a lesser extent) in M. polymorpha leads to the isomerization of 12-OPDA and formation of specific cyclopentenones 1 and 2, which are uncommon in flowering plants.

中文翻译：

---

苔藓植物模型中的脂氧合酶途径：12-oxo-9(13),15-phytodienoic acid 是 Physcomitrella patens 中的主要氧化脂

模型苔藓 Physcomitrella patens 和地草地衣拥有负责茉莉酸途径初始阶段的所有酶机制，包括活性 13(S)-脂肪氧化酶、丙二烯氧化合酶 (AOS) 和丙二烯氧化环化酶 (AOC)。同时，P. patens 和 M. polymorpha 中都缺少茉莉酸。我们对 P. patens 配子体和 M. polymorpha 组织的 oxylipins 进行的 GC-MS 分析揭示了一些独特的特性。15(Z)-cis-12-oxo-10,15-phytodienoic acid (12-OPDA) 是 M.polymorpha 中的主要 oxylipin。相比之下，12-OPDA 只是 P. patens 中的次要成分，而另一个环戊烯酮 1 是主要的 oxylipin。产物 1 通过其 MS、1H-NMR、1H-1H-CO​​SY、HSQC 和 HMBC 数据鉴定为 15(Z)-12-oxo-9(13),15-phytodienoic acid，即iso-12-OPDA . 相应的 C16 同系物 2,3-dinor-iso-12-OPDA (2) 也被检测为 P. patens 中的次要成分和 M. polymorpha 中的主要产物。此外，2,3-dinor-cis-12-OPDA (3) 也存在于 M. polymorpha 中。显然，P. patens 和 M. polymorpha 中 12-OPDA 还原酶对环戊烯酮还原的故障导致 12-OPDA 异构化和特定环戊烯酮 1 和 2 的形成，这在开花中并不常见植物。