Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative
The chloroform extract of Valeriana wallichii (V. wallichii) rhizomes was investigated to elucidate the structures responsible for reported antileishmanial activity. Besides bornyl caffeate (1, already been reported by us previously), bioassay-guided fractionation resulted in two additional cinnamic...
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doaj-25bd608536e24e749704e5f211a42c2f2020-11-25T01:02:11ZengMDPI AGMolecules1420-30492015-04-012045740575310.3390/molecules20045740molecules20045740Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone DerivativeJan Glaser0Martina Schultheis1Heidrun Moll2Banasri Hazra3Ulrike Holzgrabe4Institute of Pharmacy and Food Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, GermanyInstitute for Molecular Infection Biology, University of Wuerzburg, Josef-Schneider-Str. 2, 97080 Wuerzburg, GermanyInstitute for Molecular Infection Biology, University of Wuerzburg, Josef-Schneider-Str. 2, 97080 Wuerzburg, GermanyDepartment of Pharmaceutical Technology, Jadavpur University, Kolkata-700032, IndiaInstitute of Pharmacy and Food Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, GermanyThe chloroform extract of Valeriana wallichii (V. wallichii) rhizomes was investigated to elucidate the structures responsible for reported antileishmanial activity. Besides bornyl caffeate (1, already been reported by us previously), bioassay-guided fractionation resulted in two additional cinnamic acid derivatives 2–3 with moderate leishmanicidal activity. The structure of a novel nepetolactone derivative 4 having a cinnamic acid moiety was elucidated by means of spectral analysis. To the best of our knowledge villoside aglycone (5) was isolated from this plant for the first time. The bioassay-guided fractionation yielded two new (compounds 6–7) and two known valtrates (compounds 8–9) with leishmanicidal potential against Leishmania major (L. major) promastigotes. In addition, β-bisabolol (10), α-kessyl alcohol (11), valeranone (12), bornyl isovalerate (13) and linarin-2-O-methylbutyrate (14) were identified. This is the first report on the isolation of 4'-demethylpodophyllotoxin (15), podophyllotoxin (16) and pinoresinol (17) in V. wallichii. In total thirteen known and four new compounds were identified from the extract and their cytotoxic and antileishmanial properties were evaluated.http://www.mdpi.com/1420-3049/20/4/5740V. wallichiiantileishmanialcytotoxicitypodophyllotoxinvaltratesnovel nepetolactone derivative |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Jan Glaser Martina Schultheis Heidrun Moll Banasri Hazra Ulrike Holzgrabe |
spellingShingle |
Jan Glaser Martina Schultheis Heidrun Moll Banasri Hazra Ulrike Holzgrabe Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative Molecules V. wallichii antileishmanial cytotoxicity podophyllotoxin valtrates novel nepetolactone derivative |
author_facet |
Jan Glaser Martina Schultheis Heidrun Moll Banasri Hazra Ulrike Holzgrabe |
author_sort |
Jan Glaser |
title |
Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative |
title_short |
Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative |
title_full |
Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative |
title_fullStr |
Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative |
title_full_unstemmed |
Antileishmanial and Cytotoxic Compounds from Valeriana wallichii and Identification of a Novel Nepetolactone Derivative |
title_sort |
antileishmanial and cytotoxic compounds from valeriana wallichii and identification of a novel nepetolactone derivative |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2015-04-01 |
description |
The chloroform extract of Valeriana wallichii (V. wallichii) rhizomes was investigated to elucidate the structures responsible for reported antileishmanial activity. Besides bornyl caffeate (1, already been reported by us previously), bioassay-guided fractionation resulted in two additional cinnamic acid derivatives 2–3 with moderate leishmanicidal activity. The structure of a novel nepetolactone derivative 4 having a cinnamic acid moiety was elucidated by means of spectral analysis. To the best of our knowledge villoside aglycone (5) was isolated from this plant for the first time. The bioassay-guided fractionation yielded two new (compounds 6–7) and two known valtrates (compounds 8–9) with leishmanicidal potential against Leishmania major (L. major) promastigotes. In addition, β-bisabolol (10), α-kessyl alcohol (11), valeranone (12), bornyl isovalerate (13) and linarin-2-O-methylbutyrate (14) were identified. This is the first report on the isolation of 4'-demethylpodophyllotoxin (15), podophyllotoxin (16) and pinoresinol (17) in V. wallichii. In total thirteen known and four new compounds were identified from the extract and their cytotoxic and antileishmanial properties were evaluated. |
topic |
V. wallichii antileishmanial cytotoxicity podophyllotoxin valtrates novel nepetolactone derivative |
url |
http://www.mdpi.com/1420-3049/20/4/5740 |
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