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Cytotoxic Sesquiterpene Lactones from Kauna lasiophthalma Griseb.

Maldonado, Eliana LU ; Svensson, Daniel LU ; Oredsson, Stina LU and Sterner, Olov LU (2014) In Scientia Pharmaceutica 82(1). p.147-160
Abstract
Two new eudesmane derivatives (3 and 8) were isolated from the ethanol extract of the aerial parts of Kaunia lasiophthalma Griseb, together with 14 known eudesmane, germacrane, and guaiane sesquiterpenes, and four flavones. The structures and relative configurations of all the compounds were established by NMR spectroscopy and high-resolution mass spectrometry. The anticancer activity of sesquiterpenes 1, 3, 6-9, 11, 12, 14, and 16 was evaluated in vitro with the breast cancer cell lines HCC1937, JIMT-1, L56Br-C1, MCF-7, and SK-BR-3, and compared with the cytotoxicity in the non-cancerous breast epithelial cell line MCF-10A. All compounds were found to possess anticancer activity, and compound 1 was the most potent in all of the... (More)
Two new eudesmane derivatives (3 and 8) were isolated from the ethanol extract of the aerial parts of Kaunia lasiophthalma Griseb, together with 14 known eudesmane, germacrane, and guaiane sesquiterpenes, and four flavones. The structures and relative configurations of all the compounds were established by NMR spectroscopy and high-resolution mass spectrometry. The anticancer activity of sesquiterpenes 1, 3, 6-9, 11, 12, 14, and 16 was evaluated in vitro with the breast cancer cell lines HCC1937, JIMT-1, L56Br-C1, MCF-7, and SK-BR-3, and compared with the cytotoxicity in the non-cancerous breast epithelial cell line MCF-10A. All compounds were found to possess anticancer activity, and compound 1 was the most potent in all of the investigated cancer cell lines with IC50 values ranging between 2.0 and 6.2 μM. In order to demonstrate the importance of the α-methylene-γ-lactone/ester moiety present in all compounds for the effects on the cells, the methyl cysteine adduct 21 was prepared from 9 and found to be inactive or considerably less potent. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Scientia Pharmaceutica
volume
82
issue
1
pages
147 - 160
publisher
scipharm.at
external identifiers
  • pmid:24634851
  • scopus:84896890125
ISSN
2218-0532
DOI
10.3797/scipharm.1310-18
language
English
LU publication?
yes
id
f5c2333f-9949-429f-a508-b363ae896a17 (old id 4383150)
date added to LUP
2014-04-25 10:52:24
date last changed
2017-10-29 04:04:20
@article{f5c2333f-9949-429f-a508-b363ae896a17,
  abstract     = {Two new eudesmane derivatives (3 and 8) were isolated from the ethanol extract of the aerial parts of Kaunia lasiophthalma Griseb, together with 14 known eudesmane, germacrane, and guaiane sesquiterpenes, and four flavones. The structures and relative configurations of all the compounds were established by NMR spectroscopy and high-resolution mass spectrometry. The anticancer activity of sesquiterpenes 1, 3, 6-9, 11, 12, 14, and 16 was evaluated in vitro with the breast cancer cell lines HCC1937, JIMT-1, L56Br-C1, MCF-7, and SK-BR-3, and compared with the cytotoxicity in the non-cancerous breast epithelial cell line MCF-10A. All compounds were found to possess anticancer activity, and compound 1 was the most potent in all of the investigated cancer cell lines with IC50 values ranging between 2.0 and 6.2 μM. In order to demonstrate the importance of the α-methylene-γ-lactone/ester moiety present in all compounds for the effects on the cells, the methyl cysteine adduct 21 was prepared from 9 and found to be inactive or considerably less potent.},
  author       = {Maldonado, Eliana and Svensson, Daniel and Oredsson, Stina and Sterner, Olov},
  issn         = {2218-0532},
  language     = {eng},
  number       = {1},
  pages        = {147--160},
  publisher    = {scipharm.at},
  series       = {Scientia Pharmaceutica},
  title        = {Cytotoxic Sesquiterpene Lactones from Kauna lasiophthalma Griseb.},
  url          = {http://dx.doi.org/10.3797/scipharm.1310-18},
  volume       = {82},
  year         = {2014},
}