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Planta Med 2023; 89(02): 134-139
DOI: 10.1055/a-1822-1486
Biological and Pharmacological Activity
Original Papers

Sesquiterpene Lactones with Astrodaucane Skeleton from Astrodaucus orientalis

Hossein Hashempour
1   Department of Chemistry, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran
,
Farshid Herfati
1   Department of Chemistry, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran
,
Hassan Valizadeh
1   Department of Chemistry, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran
,
Fatemeh Mahmoudi-Kordi
2   Department of Biology, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran
,
Samad Nejad Ebrahimi 
3   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran
,
Matthias Hamburger 
4   Pharmaceutical Biology, Pharmacenter, University of Basel, Basel, Switzerland
,
Mahdi Moridi Farimani
3   Department of Phytochemistry, Medicinal Plants and Drugs Research Institute, Shahid Beheshti University, Evin, Tehran, Iran
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Abstract

Four 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.

Key words

Astrodaucus orientalis - Apiaceae - sesquiterpene lactone - Astrodaucane - Germacryl cation - Eudesmane

Supporting Information

    NMR spectra of compounds 1–4 and Identification of Compounds 5 and 6 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 17 October 2021

Accepted after revision: 09 April 2022

Accepted Manuscript online:
09 April 2022

Article published online:
10 January 2023

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