Liriogerphines A–D, a Class of Sesquiterpene–Alkaloid Hybrids from the Rare Chinese Tulip Tree Plant

Abstract

Liriogerphines A–D (1–4, respectively), an unprecedented class of hybrids of germacranolide-type sesquiterpenoids and aporphine-type alkaloids, were isolated from the rare medicinal plant Liriodendron chinense. Their structures were elucidated by comprehensive spectroscopic analyses combined with electronic circular dichroism calculations and X-ray crystallographic data. Biosynthetically, an aza-Michael addition reaction is proposed to be involved in the assemblies of this class of hybrids. Compound 4 exhibited cytotoxicity against leukemia cells via inducing apoptosis and inhibiting Bcl-2 expression.

Antioxidant, Antimicrobial, and Anti-Inflammatory Effects of Liriodendron chinense Leaves

“…chinense has been recorded in the Compilation of Countrywide Herbal Medicine of China. Traditionally, it is recognized for its therapeutic functions in dispelling wind and dampness, dispersing cold, relieving coughs, and reducing inflammation . An expanding body of research has underscored Liriodendron’s efficacy in mitigating hyperuricemic nephropathy associated with inflammation and renal fibrosis, its proficiency in mitigating lipid oxidation, and its antimicrobial attributes. , Nevertheless, the bulk of these studies have gravitated toward investigating L.…”

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“…2 Liriogerphines A–D, from the Chinese tulip tree Liriodendron chinense , are a new class of sesquiterpenoid–alkaloid hybrids. 3 It is proposed that the biosynthesis of the liriogerphines involves an aza-Michael addition of an aporphine or proaporphine alkaloid to a germacranolide. The structures of sophoraline 1 , thiocytochalasin A 2 and liriogerphine A 3 were all confirmed by X-ray analyses.…”