Synthesis and anti-influenza activity of a series of triterpene furoyloxy-acylates

A series of lupane, oleanane and ursane furoyloxy-triterpenoids were synthesised <i>via</i> acylation with 2-furoyl chloride and subsequently tested for anti-influenza activity against the pandemic influenza virus A/Puerto Rico/8/1934 (H1N1). Among them, 3<i>β</i>-furoyloxy-oleanolic and 3<i>β</i>-furoyloxy-ursolic acids were the most potent with IC<sub>50</sub> values 17 and 1 <i>µ</i>M with selectivity indexes of 32 and 26, respectively. The molecular structure of compound <b>11</b> was determined by X-ray diffraction analysis.

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Publication Details

Journal
Natural Product Research
Published
2025-10-17
DOI
https://doi.org/10.1080/14786419.2025.2569807
Primary Topic
Natural product bioactivities and synthesis
Type
article
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article

Synthesis and anti-influenza activity of a series of triterpene furoyloxy-acylates

Dmitriy Polovyanenko, И. Е. Смирнова, Yu. V. Gatilov, О. Б. Казакова et al.
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article

Synthesis and anti-influenza activity of a series of triterpene furoyloxy-acylates

Dmitriy Polovyanenko, И. Е. Смирнова, Yu. V. Gatilov, О. Б. Казакова, Alexandrina S. Volobueva, Владимир В. Зарубаев, Maria Niukalova
article en

Abstract

A series of lupane, oleanane and ursane furoyloxy-triterpenoids were synthesised <i>via</i> acylation with 2-furoyl chloride and subsequently tested for anti-influenza activity against the pandemic influenza virus A/Puerto Rico/8/1934 (H1N1). Among them, 3<i>β</i>-furoyloxy-oleanolic and 3<i>β</i>-furoyloxy-ursolic acids were the most potent with IC<sub>50</sub> values 17 and 1 <i>µ</i>M with selectivity indexes of 32 and 26, respectively. The molecular structure of compound <b>11</b> was determined by X-ray diffraction analysis.

Natural Product Research
Novosibirsk Institute of Organic Chemistry (RU), Saint Petersburg Pasteur Institute (RU), Ufa Institute of Chemistry (RU), Institute of Virology of the Slovak Academy of Sciences (SK)
Openalex Percentile: Top 74%
Natural product bioactivities and synthesis
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