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DOI: 10.1055/a-1554-2866
New Guaianolide Sesquiterpene Lactones and Other Constituents from Pyrethrum pulchrum
Abstract
Pyrethrum pulchrum is a rare Mongolian plant species that has been traditionally used as an ingredient in various remedies. Bioactivity-guided fractionation performed on the methanol extract of its aerial parts led to the isolation of 2 previously undescribed guaianolide-type sesquiterpene lactones, namely 1β,10β-epoxy-8α-hydroxyguaia-3,11(13)-dien-6,12-olide (1) and 1,8,10-trihydroxyguaia-3,11(13)-dien-6,12-olide (2), along with the isolation or chromatographic identification of 11 compounds, arglabin (3), 3β-hydroxycostunolide (4), isocostic acid (5), (E)-9-(2-thienyl)-6-nonen-8-yn-3-ol (6), (Z)-9-(2-thienyl)-6-nonen-8-yn-3-ol (7), N 1,N 5,N 10,N 14-tetra-p-coumaroyl spermine (8), chlorogenic acid (9), 3,5-di-O-caffeoylquinic acid (10), 3,5-di-O-caffeoylquinic acid methyl ester (11), 3,4-di-O-caffeoylquinic acid (12), and tryptophan (13). Their structures were assigned based on spectroscopic and spectrometric data. The antimicrobial, antiproliferative and cytotoxic activities of selected compounds were evaluated. The new compounds showed weak to moderate antimicrobial activity. Arglabin (3), the major sesquiterpene lactone found in the methanol extract of P. pulchrum, exhibited the highest activity against human cancer lines, while compound 1 also possesses significant antiproliferative activity against leukemia cells.
Key words
Pyrethrum pulchrum - Asteraceae - sesquiterpene lactone - antiproliferative effect - cytotoxicity - leukemia cell linesSupporting Information
- Supporting Information
Spectroscopic data of known compounds, a list of all isolated compounds (Table 1S); bioactivity data of the plant extract, main fractions and compounds 1 and 2 (Table 2S and 3S), force field optimized structure and CD spectra of compound 1, NMR and mass spectra of compounds 1 – 13 (Fig. 1S–62S), and concentration-response curves of antiproliferative and cytotoxic effects of compounds 1, 3, and 4 (Fig. 63S) are available as Supporting Information.
Publication History
Received: 16 September 2020
Accepted after revision: 14 July 2021
Article published online:
05 August 2021
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