TY - JOUR

T1 - Identification of early quassinoid biosynthesis in the invasive tree of heaven (Ailanthus altissima) confirms evolutionary origin from protolimonoids

AU - Chuang, Ling

AU - Liu, Shenyu

AU - Biedermann, Dave

AU - Franke, Jakob

N1 - Funding Information: This work was financially supported by the Fonds der Chemischen Industrie, the Emmy Noether programme of the Deutsche Forschungsgemeinschaft (DFG) (FR 3720/3-1) and the SMART BIOTECS alliance between the Technische Universität Braunschweig and the Leibniz Universität Hannover, supported by the Ministry of Science and Culture (MWK) of Lower Saxony. We also thank the DFG for the provision of NMR equipment (INST 187/686-1). In addition, this work was supported by the LUH compute cluster, which is funded by the Leibniz Universität Hannover, the Lower Saxony Ministry of Science and Culture (MWK) and the German Research Association (DFG).

PY - 2022/8/23

Y1 - 2022/8/23

N2 - The tree of heaven, Ailanthus altissima (MILL.) SWINGLE, is a globally invasive plant known to secrete allelopathic metabolites called quassinoids. Quassinoids are highly modified triterpenoids. So far, nothing has been known about the biochemical basis of quassinoid biosynthesis. Here, based on transcriptome and metabolome data of Ailanthus altissima, we present the first three steps of quassinoid biosynthesis, which are catalysed by an oxidosqualene cyclase and two cytochrome P450 monooxygenases, resulting in the formation of the protolimonoid melianol. Strikingly, these steps are identical to the first steps of the biosynthesis of limonoids, structurally different triterpenoids from sister plant families within the same order Sapindales. Our results are therefore not only important to fully understand the biosynthesis of complex triterpenoids in plants, but also confirm the long-standing hypothesis that quassinoids and limonoids share an evolutionary origin. In addition, our transcriptome data for Ailanthus altissima will be beneficial to other researchers investigating the physiology and ecology of this invasive tree.

AB - The tree of heaven, Ailanthus altissima (MILL.) SWINGLE, is a globally invasive plant known to secrete allelopathic metabolites called quassinoids. Quassinoids are highly modified triterpenoids. So far, nothing has been known about the biochemical basis of quassinoid biosynthesis. Here, based on transcriptome and metabolome data of Ailanthus altissima, we present the first three steps of quassinoid biosynthesis, which are catalysed by an oxidosqualene cyclase and two cytochrome P450 monooxygenases, resulting in the formation of the protolimonoid melianol. Strikingly, these steps are identical to the first steps of the biosynthesis of limonoids, structurally different triterpenoids from sister plant families within the same order Sapindales. Our results are therefore not only important to fully understand the biosynthesis of complex triterpenoids in plants, but also confirm the long-standing hypothesis that quassinoids and limonoids share an evolutionary origin. In addition, our transcriptome data for Ailanthus altissima will be beneficial to other researchers investigating the physiology and ecology of this invasive tree.

KW - Ailanthus altissima

KW - plant biochemistry

KW - protolimonoids

KW - quassinoids

KW - specialised metabolism

KW - transcriptomics

KW - tree of heaven

KW - triterpene

UR - http://www.scopus.com/inward/record.url?scp=85139446057&partnerID=8YFLogxK

U2 - 10.3389/fpls.2022.958138

DO - 10.3389/fpls.2022.958138

M3 - Article

AN - SCOPUS:85139446057

VL - 13

JO - Frontiers in Plant Science

JF - Frontiers in Plant Science

SN - 1664-462X

M1 - 958138

ER -