Sesquiterpene Lactones with Astrodaucane Skeleton from Astrodaucus orientalis

Planta Med DOI: 10.1055/a-1822-1486Four sesquiterpene lactones, astrodaucanolide A – D (1–4) with
unique structures, toghether with two known phenylpropanoid esters (5 and
6) were isolated from a flower extract of Astrodaucus
orientalis. The structures were established by 1D and 2D NMR
spectroscopy and high-resolution mass spectrometry (HRESIMS), and the absolute
configuration of 1–4 was determined by electronic circular
dichroism (ECD). Compounds 1–4 novel architecture represents a new
class of sesquiterpenes with new skeleton. A putative biosynthetic pathway for
their scaffold is proposed with a germacryl cation as the precursor. The
suggested biosynthesis pathway is similar to that of eudesmane sesquiterpenes
with a different direction of protonation which then leads to the new skeleton,
named astrodaucane by the 1,2-methyl migration. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Planta Medica - January 10, 2023 Category: Drugs & Pharmacology Authors: Hashempour, Hossein Herfati, Farshid Valizadeh, Hassan Mahmoudi-Kordi, Fatemeh Ebrahimi, Samad Nejad Hamburger, Matthias Farimani, Mahdi Moridi Tags: Original Papers Source Type: research