Echiumin E, an Aryl Dihydronaphthalene Lignan from the Australian Invasive Plant Paterson's Curse (Echium plantagineum)

Ju Jin; Darren C Holland; Anthony R Carroll; Matthew Zunk

doi:10.1021/acs.jnatprod.2c00151

Echiumin E, an Aryl Dihydronaphthalene Lignan from the Australian Invasive Plant Paterson's Curse (Echium plantagineum)

J Nat Prod. 2022 Oct 28;85(10):2474-2479. doi: 10.1021/acs.jnatprod.2c00151. Epub 2022 Sep 20.

Authors

Ju Jin^{1

2}, Darren C Holland^{3

4}, Anthony R Carroll^{3

4}, Matthew Zunk^{1

2}

Affiliations

¹ School of Pharmacy and Medical Science, Griffith University, Gold Coast Campus, Queensland 4222, Australia.
² Menzies Health Institute Queensland, Griffith University, Gold Coast Campus, Queensland 4222, Australia.
³ School of Environment and Science, Griffith University, Southport, Queensland 4222, Australia.
⁴ Griffith Institute for Drug Discovery, Griffith University, Nathan, Queensland 4111, Australia.

PMID: 36126331
DOI: 10.1021/acs.jnatprod.2c00151

Abstract

A new aryl dihydronaphthalene lignan, echiumin E (1), and four known compounds, echiumin A, globoidnan A, (-)-rabdosiin, and rosmarinic acid (2-5), were isolated from the Australian invasive plant Echium plantagineum (Paterson's curse) for the first time. Echiumin E (1) was characterized by 1D/2D NMR spectroscopy and MS spectrometry, with its absolute configuration assigned through comparison of experimental and TDDFT-calculated ECD data. Echiumin E (1) along with compounds 3-5 were screened in vitro against three cancer cell lines (SH-SY5Y, HeLa, and PC-3) and a prostate stromal (normal) cell line (WPMY-1) using a resazurin reduction assay. Echiumin E (1) was found to be active toward HeLa cells (IC₅₀ 0.21 μM).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Australia
Echium* / chemistry
Echium* / metabolism
HeLa Cells
Humans
Lignans* / metabolism
Lignans* / pharmacology
Male
Neuroblastoma*
Plants

Substances

Lignans