An efficient, green, and easy‐to‐scale‐up strategy for target‐oriented isolating cadinene sesquiterpenoids from Eupatorium adenophorum Spreng

Abstract

A green and efficient strategy was established and optimized for target‐oriented extraction, enrichment and separation of cadinene sesquiterpenoids from Eupatorium adenophorum Spreng., using the combination of supercritical fluid extraction, molecular distillation, and industrial preparative chromatography for the first time. The extraction conditions of supercritical fluid extraction were initially optimized by orthogonal experimental design. Under the optimum conditions, the contents of 9‐oxo‐10,11‐dehydroageraphorone and 10Hβ‐9‐oxo‐ageraphorone, which were 55.00% and 6.01%, respectively, were much higher than conventional extraction methods. Then, the molecular distillation enrichment method was established and investigated by response surface methodology technology, which showed strong specificity for enriching target compounds and removing impurities from crude extracts. Under the optimum conditions of molecular distillation, total contents of cadinene sesquiterpenoids were increased to 89.19%. Finally, a total of 146 mg of 9‐oxo‐10,11‐dehydroageraphorone and 29 mg of 10Hβ‐9‐oxo‐ageraphorone were easily obtained by industrial preparative chromatography, from 200 mg of distillation fraction, with purities over 99%. The contents of target components were analyzed by HPLC, and structures of them were identified by high‐resolution MS, 1H‐NMR, and 13C‐NMR spectroscopy. These results indicate that it is a simple, effective, and eco‐friendly strategy, which is easily converted into industrial scale.

Transcriptome and Metabolome Analysis of the Synthesis Pathways of Allelochemicals in Eupatorium adenophorum

“…Cinnamic acid, coumarin, and ferulic acid are phenylpropanoid metabolites, catechin and epicatechin are flavonoids metabolites, and HHO is a sesquiterpene metabolite. − Five DEGs were identified in the phenylpropanoid synthesis pathway ( p < 0.05): two genes ( PAL1 and PAL2 ) annotated as phenylalanine amino lyase (PAL), six β-glucosidase (bglx) genes ( bglx1 , bglx2 , bglx3 , bglx4 , bglx5 , and bglx6 ), two cinnamate-4-hydroxylase (C4H) genes ( C4H1 and C4H2 ), two 4-coumaroyl-CoA ligase (4CL) genes ( 4CL1 and 4CL2 ), and three caffeic acid O -methyltransferase (COMT) genes ( COMT1 , COMT2 , and COMT3 ). Most genes were highly expressed in roots and blades.…”