抗癌苦李蕈二萜的存在是中国传统草药川芎中的化学分类标志，尽管苦羟二萜生物合成的分子机制仍不清楚。在这里，我们报告了对川芎的414.98 Mb基因组进行了高质量组装，形成了13个拟染色体。通过系统发育学和生物化学数据，我们揭示了紫薇科植物川芎、黄芩和美丽鼠尾草中三种植物的拟囊体代谢途径，包括开合松萜、阿里碳和苦羟二萜。这有助于确定参与苦李蕈二萜、科拉韦诺尔和异科拉韦诺尔生物合成的基因。我们发现，苦羟二萜的生物合成是通过从开合松萜和阿里碳代谢途径中招募和新功能化基因进化而来的。尽管苦羟二萜生物合成被认为是紫薇科植物共同的起源，但我们的数据显示出不同的进化分支并且在紫薇科中苦羟二萜生物合成的起源是多源的。我们的研究不仅为紫薇科植物中苦羟二萜生物合成途径的进化提供了重要见解，还将有助于未来代谢工程的制备抗癌的苦羟二萜。版权所有©2023该作者。由Elsevier Inc.发表，版权所有。

The presence of anticancer clerodane diterpenoids is a chemotaxonomic marker for the traditional Chinese medicinal plant Scutellaria barbata, although the molecular mechanisms behind clerodane biosynthesis are unknown. Here, we report a high-quality assembly of the 414.98 Mb genome of S. barbata into 13 pseudochromosomes. Using phylogenomic and biochemical data, we mapped the plastidial metabolism of kaurene (gibberellins), abietane, and clerodane diterpenes in three species of the family Lamiaceae (Scutellaria barbata, Scutellaria baicalensis, and Salvia splendens), facilitating the identification of genes involved in the biosynthesis of the clerodanes, kolavenol, and isokolavenol. We show that clerodane biosynthesis evolved through recruitment and neofunctionalization of genes from gibberellin and abietane metabolism. Despite the assumed monophyletic origin of clerodane biosynthesis, which is widespread in species of the Lamiaceae, our data show distinct evolutionary lineages and suggest polyphyletic origins of clerodane biosynthesis in the family Lamiaceae. Our study not only provides significant insights into the evolution of clerodane biosynthetic pathways in the mint family, Lamiaceae, but also will facilitate the production of anticancer clerodanes through future metabolic engineering efforts.Copyright © 2023 The Author. Published by Elsevier Inc. All rights reserved.