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Planta Med 2022; 88(05): 380-388
DOI: 10.1055/a-1554-2866
Biological and Pharmacological Activity
Original Papers

New Guaianolide Sesquiterpene Lactones and Other Constituents from Pyrethrum pulchrum

Uugangerel Erdenetsogt 
1   Mongolian National University of Medical Sciences, Ulaanbaatar, Mongolia
,
Suvd Nadmid
1   Mongolian National University of Medical Sciences, Ulaanbaatar, Mongolia
,
Christian Paetz
2   Max Planck Institute for Chemical Ecology, Jena, Germany
,
Hans-Martin Dahse
3   Leibniz Institute for Natural Product Research and Infection Biology, Hans-Knöll-Institute (HKI), Jena, Germany
,
Kerstin Voigt
3   Leibniz Institute for Natural Product Research and Infection Biology, Hans-Knöll-Institute (HKI), Jena, Germany
,
Choijamts Gotov
4   Otoch Manramba University of Mongolia, Ulaanbaatar, Mongolia
,
Wilhelm Boland
2   Max Planck Institute for Chemical Ecology, Jena, Germany
,
Enkhmaa Dagvadorj 
1   Mongolian National University of Medical Sciences, Ulaanbaatar, Mongolia
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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 lines

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.

  • Supporting Information


Publikationsverlauf

Eingereicht: 16. September 2020

Angenommen nach Revision: 14. Juli 2021

Artikel online veröffentlicht:
05. August 2021

© 2021. Thieme. All rights reserved.

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