Andre Christelle M, Sansom Catherine E, Plunkett Blue J, Hamiaux Cyril, Massey Lenhy, Chan Andrew, Caddie Manu, Espley Richard V, Perry Nigel B
The New Zealand Institute for Plant and Food Research Limited (PFR), Mt Albert Research Centre, Auckland, 1142, New Zealand.
PFR, Chemistry Department, University of Otago, Dunedin, 9016, New Zealand.
New Phytol. 2025 Jun;246(6):2666-2682. doi: 10.1111/nph.20349. Epub 2024 Dec 23.
The potential of cannabinoids to address public health challenges has stimulated exploration into alternative sources and production technologies. Radula marginata, an endemic Aotearoa/New Zealand liverwort, produces the bibenzyl cannabinoid perrottetinene (PET), analogous to Cannabis psychoactive tetrahydrocannabinol (THC). Structural differences between PET and THC could alter therapeutic interactions and mitigate adverse side effects. To understand the cannabinoid production potential of R. marginata, we analyzed 75 collections from three locations across several seasons, collaborating with kaitiaki Māori (indigenous guardians). Metabolic plasticity of the phytocannabinoids and plant growth was assessed under controlled growth conditions, and in in vitro culture. Perrottetinene diol (trans-PTD), analogous to cannabidiol (trans-CBD), and its acid precursor (PTDA), were identified and fully characterized from nature for the first time. Bibenzyl-4-geranyl (BB4G), analogous to cannabigerol (CBG), and its corresponding acid (BB4GA), were also isolated. Radula marginata showed chemotypes dominated by PET, PTD, or BB4G, in striking analogy to the main Cannabis chemotypes. These site-selective chemotypes persisted after growth under artificial lighting and in in vitro progeny, suggesting genetic control. These results expand phytocannabinoid knowledge through the discovery of PTD analogous to CBD. They add a new dimension to liverwort cannabinoids and suggest convergent evolution of biosynthesis in two distant plant lineages.
大麻素应对公共卫生挑战的潜力激发了人们对替代来源和生产技术的探索。新西兰特有的叶苔类植物边缘叶苔（Radula marginata）能产生联苄类大麻素佩罗替丁烯（PET），类似于大麻中的精神活性成分四氢大麻酚（THC）。PET与THC之间的结构差异可能会改变治疗相互作用并减轻副作用。为了解边缘叶苔的大麻素生产潜力，我们与毛利族守护者（当地守护者）合作，分析了在几个季节里从三个地点采集的75份样本。在可控生长条件下以及体外培养中评估了植物大麻素的代谢可塑性和植物生长情况。首次从自然界中鉴定并全面表征了与大麻二酚（反式CBD）类似的佩罗替丁烯二醇（反式PTD）及其酸前体（PTDA）。还分离出了与大麻萜酚（CBG）类似的联苄-4-香叶基（BB4G）及其相应的酸（BB4GA）。边缘叶苔呈现出以PET、PTD或BB4G为主的化学型，这与大麻的主要化学型极为相似。这些位点选择性化学型在人工光照下生长以及体外子代培养后依然存在，表明存在基因控制。这些结果通过发现与CBD类似的PTD，扩展了植物大麻素的知识。它们为叶苔类大麻素增添了新的维度，并表明在两个远缘植物谱系中生物合成存在趋同进化。
