cytotoxic germacranolide sesquiterpene lactones fromCarpesium triste var.manshuricum

Kim, Mi Ran; Hwang, Bang Yeon; Jeong, Eun-Sook; Lee, Young Moo; Yoo, Hwan‐Soo; Chung, Youn Bok; Hong, Jin Tae; Moon, Dong-Cheul

doi:10.1007/bf02977648

Cited by 14 publications

(12 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 10 – 14 were identified as (2 S , 4 R , 5 R , 6 R , 7 S , 8 S , 9 R , 10 S , 2″ R ) -2,5-epoxy-5,10-dihydroxy-6-angeloyloxy-9-2-methylbutyryloxy-germacran-8,12-olide ( 10 ) 14 , 25 , 26 , (2 S , 4 R , 5 R , 6 R , 7 S , 8 S , 9 R , 10 S , 2″ S )-2,5-epoxy-5,10-dihydroxy-6-angeloyloxy-9-2-methylbutyryloxy-germacran-8,12-olide ( 11 ) 14 , 25 , 26 , (2 S , 4 R , 5 R , 6 R , 7 S , 8 S , 9 R , 10 S )-2,5-epoxy-5,10-dihydroxy-6-angeloyloxy-9-angeloyloxy-germacran-8,12-olide ( 12 ) 8 , 14 , 25 , 26 , 2 α ,5-epoxy-5,10-dihydroxy-6 α -angeloyloxy-9 β -3-methylbutyryloxy-germacran-8,12-olide ( 13 ) 18 – 20 , 25 , 26 , and 2 α ,5-epoxy-5,10-dihydroxy-6 α -angeloyloxy-9 β -isobutyryloxy-germacran-8,12-olide ( 14 ) 9 , 19 , 20 , 26 by comparison of their MS, 1 H NMR, and 13 CNMR spectral with reported data. The conclusions were also confirmed by the 1 H- 1 H COSY, HSQC, HMBC, and NOESY spectra.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Zhang

Chen

et al. 2018

Sci Rep

View full text Add to dashboard Cite

Five sets of germacrane isomers (1/8/17, 2/7/10/11/13/16/18, 3/4/5/14/20, 6/12/15, and 9/19) with different skeletal types, including seven new ones (1–3, 8–9, and 15–16) were isolated from the whole plant of Carpesium divaricatum. Among them, there are six pairs of stereoisomers (1/8, 2/13, 4/14, 6/12, 7/11 and 10/11). The planar structures and relative configurations of the new compounds were elucidated by detailed spectroscopic analysis. The absolute configurations of 4, 10, 11, and 17 were established by circular dichroism (CD) spectra and X-ray crystallographic analyses, and the stereochemistry of the new compounds 1–3, 8–9, and 15–16 were determined by similar CD spectra with 4, 10, 11, and 17, respectively. The confusion in the literature about subtypes I and II of germacranolides was clarified in this paper. The NMR data of 10–11, and the absolute configurations of the known compounds 4–6, 13–14, and 17–20 were reported for the first time. Compounds 13, 17, and 18 showed cytotoxicity against human cervical (HeLa), colon (LoVo) and stomach cancer (BGC-823) cell lines with IC50 values in the range 4.72–13.68 μM compared with the control cis-platin (7.90–15.34 μM).

show abstract

Section: Resultsmentioning

confidence: 99%

“…In addition, compounds 10 and 11 were usually reported as a mixture from C. triste 25 , 26 . Although both of them were separated successfully in the literature 14 , the NMR data have not been reported.…”

Section: Resultsmentioning

confidence: 99%

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Zhang

Chen

et al. 2018

Sci Rep

View full text Add to dashboard Cite

show abstract

“…1A) was isolated from the airdried whole plant of Carpesium triste var. manshuricum (950 g) as described previously (Kim et al 2007). Test material was dissolved in DMSO; the final concentration of DMSO in cell culture media was less than 0.1%.…”

Section: Test Materialsmentioning

confidence: 99%

“…manshuricum, which is used in folk medicine in Korea as an antipyretic, analgesic, and anti-inflammatory treatment. Recent studies indicate that EDAG shows cytotoxic activity against several cancer cells (Kim et al 1999;Kim et al 2007). However, the effect of EDAG on nitric oxide synthase and its molecular mechanism has not yet been studied.…”

Section: Introductionmentioning

confidence: 99%

A germacranolide sesquiterpene lactone suppressed inducible nitric oxide synthase by downregulating NF-κB activity

Lee

Jung

Kwon

et al. 2011

Can. J. Physiol. Pharmacol.

Self Cite

View full text Add to dashboard Cite

A germacranolide sesquiterpene lactone, 2α,5-epoxy-5,10-dihydroxy-6α-angeloyloxy-9β-(3-methylbutyloxy)-germacran-8α,12-olide (EDAG), isolated from Carpesium triste var. manshuricum, showed inhibitory activity in the production of nitric oxide (NO) and the expression of inducible nitric oxide synthase (iNOS) mRNA and protein in LPS-activated macrophage cells. Molecular analysis reveals that these suppressive effects are correlated with the inhibition of NF-κB activation by EDAG. Immunoblotting showed that EDAG suppressed the LPS-induced degradation of I-κBα and decreased nuclear translocation of p65. Furthermore, EDAG showed reduced phosphorylation of ERK1/2 and p38 MAPK, whereas activation of JNK was not changed. These data suggest, at least in part, that EDAG utilizes the signal cascades of ERK1/2, p38 MAPK, and NF-κB for the suppression of iNOS gene expression.

show abstract

“…The parent nucleus of the germacranes contains a special ten member ring with different post-modification to produce diverse structural features. A survey of the literature has shown that a large number of germacranolides are isolated from the genus Carpesium , but their absolute configurations have rarely been reported67812131920212223.…”

mentioning

confidence: 99%

New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity

Zhang

et al. 2016

Sci Rep

View full text Add to dashboard Cite

Eight highly oxygenated germacranolides (1–8) including four new ones (2–5) were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by NMR experiment and HRESIMS data. The absolute configuration of 1 was established by circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2–5 were determined by similar CD spectra with 1. Compound 2 is the first hydroperoxyl germacrane from the genus Carpesium. The 13C NMR data of 1, NMR data of 6–7, and their absolute configurations were reported for the first time. Two new compounds (2 and 4) and two known compounds (6 and 8) exhibited potent cytotoxicity against human cervical cancer (HeLa) cells, superior to that of the positive control doxorubicin.

show abstract

cytotoxic germacranolide sesquiterpene lactones fromCarpesium triste var.manshuricum

Cited by 14 publications

References 20 publications

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

A germacranolide sesquiterpene lactone suppressed inducible nitric oxide synthase by downregulating NF-κB activity

New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity

Contact Info

Product

Resources

About