Eudesmane Sesquiterpenes and Other Constituents from <i>Aster himalaicus</i>

Xie, Wei Dong; Weng, Cheng Wu; Niu, Yu; Lai, Peng Xiang; Row, Kyung Ho

doi:10.1002/cbdv.200900007

Cited by 12 publications

(9 citation statements)

References 14 publications

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“…The structure of OEL, isolated from Aster himalaicus, was identified by spectral data, as previously described [14] ( Figure 1A). Purified OEL (>98%) was dissolved in dimethylsulfoxide (DMSO) at 10 mmol/L as a stock and diluted as necessary, according to experimental requirements.…”

Section: Chemicals and Reagentsmentioning

confidence: 97%

“…More than 20 aster species have been used in traditional Chinese medicine to treat snakebites, fever, cold, tonsillitis, and pneumonia [14] . In the present study, we examined 1-oxoeudesm-11(13)-eno-12,8a-lactone (OEL), a novel, eudesmane-type sesquiterpene compound isolated from the Chinese herb, Aster himalaicus, which we described in our previous report [14] . We also investigated the anti-cancer activity and mechanisms of action of OEL in the human malignant glioma cell lines, U87 and A172.…”

Section: Introductionmentioning

confidence: 99%

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1-Oxoeudesm-11(13)-eno-12,8a-lactone induces G2/M arrest and apoptosis of human glioblastoma cells in vitro

et al. 2012

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Aim:To investigate the effects of 1-oxoeudesm-11(13)eno-12,8a-lactone (OEL), a novel eudesmane-type sesquiterpene isolated from Aster himalaicus, on the cell cycle and apoptosis in human glioblastoma cells in vitro. Methods: Human malignant glioblastoma cell lines U87 and A172 were used. The cytotoxicity of OEL was examined using the MTT assay. Cell apoptosis was assessed with DAPI staining and flow cytometry. DNA damage was determined by measuring the phosphorylation of H2AX using immunofluorescence staining and Western blotting. Cell cycle profiles were measured with flow cytometry. The mRNA expression of p53 and p21Waf1/Cip1 was investigated using real-time PCR. The protein expression of γ-H2AX, caspase-9, caspase-3, p53, p21Waf1/Cip1, cyclin B1, and cdc2 was analyzed with Western blotting. Results: Treatment of the malignant glioblastoma cells with OEL inhibited the cell growth in dose-and time-dependent manners (the values of IC 50 at 48 and 72 h were 29.5 and 16.99 μmol/L, respectively, in U87 cells; 7.2 and 9.5 μmol/L, respectively, in A172 cells). OEL (10-30μmol/L) induced apoptosis and G 2 /M phase arrest in both U87 and A172 cells. OEL induced the phosphorylation of cdc2, a G 2 /M phase cyclin-dependent kinase, and decreased the expression of cyclin B1 required for progression through the G 2 /M phase in U87 cells. The compound remarkably increased the phosphorylation of H2AX in U87 cells. Moreover, OEL increased the mRNA and protein levels of p53 and its target gene p21Waf1/Cip1 in U87 cells. The compound also induced p53 phosphorylation. Pretreatment with PFT-α, a specific inhibitor of p53 transcriptional activity, could partially reverse the inhibition of OEL on the viability of U87 and A172 cells. Conclusion: OEL suppresses the growth of human glioblastoma cells in vitro via inducing DNA damage, p53-mediated cell cycle arrest and apoptosis, thus warrants further studies as a lead compound of anti-glioblastoma drug.

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Section: Chemicals and Reagentsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

1-Oxoeudesm-11(13)-eno-12,8a-lactone induces G2/M arrest and apoptosis of human glioblastoma cells in vitro

et al. 2012

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“…The investigation of the structure diversities, structure-activity relationships and biosynthetic approaches of the sesquiterpenoid constitutes in traditional Chinese medicines to screen for cytotoxic leads to drug has been the principal subject of our researchs. 8,9) Ligularia fischeri (LEDEB.) TURCZ.…”

Section: Notementioning

confidence: 99%

Fischerisin A and B, Cytotoxic Sesquiterpenoid-Geranylhydroquinones from Ligularia fischeri

Xie

Weng

et al. 2011

Chem. Pharm. Bull.

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NoteSesquiterpenoids are the characteristic secondary metabolites of the Asteraceae family.1) Some of them showed a wide range of biological and pharmacological properties including insect antifeedant,2) anti-inflammatory activity, 3) antibacterial activity, 4) antimalarial activity, 5) cytotoxicity, 6) and nuclear factor kB (NF-kB) inhibition activity 7) etc. The investigation of the structure diversities, structure-activity relationships and biosynthetic approaches of the sesquiterpenoid constitutes in traditional Chinese medicines to screen for cytotoxic leads to drug has been the principal subject of our researchs. 8,9) Ligularia fischeri (LEDEB.) TURCZ. (Asteraceae) has long been used as a folk medicine in China for the treatment of coughs, inflammations, jaundice, scarlet fever, rheumatoidal arthritis, and hepatic diseases.10) In the mid1970s, Japanese researchers initially isolated furanoeremophilane-type sesquiterpenoids from this plant for the first time.11) Subsequent phytochemical researches of this plant collected in different region have resulted in the isolation of many eremophilane-type lactones and norsesquiterpene derivatives. [12][13][14] Recently, we reported the structures of eremophilane dimers and an eremophilane lactam from this plant. 15,16) This paper describes the isolation and structure elucidation of two sesquiterpenoid-geranylhydroquinone hybrids, namely fischerisin A (1) and fischerisin B (2), isolated from the roots of L. fischeri. To the best of our knowledge, these two compounds represent a kind of unprecedented sesquiterpenoid derivative. In addition, the in vitro cytotoxicity of both compounds against cultured human oral epidermoid carcinoma (KB) and human breast cancer (MCF-7) cell lines was also evaluated. Results and DiscussionThe petroleum ether (60-90°C)-Et 2 O-CH 3 OH (1 : 1 : 1) extract of the root of L. fischeri was chromatographed on a silica gel column with a gradient of hexane-acetone as eluent. After the sequential purification, fischerisin A (1) and fischerisin B (2) were finally obtained from the part of hexane-acetone (10 : 1).Fischerisin A (1) During the course of screening natural sesquiterpenoids for new antitumor agents, two novel compounds, fischerisin A (1) and fischerisin B (2), were isolated from the roots of Ligularia fischeri. Their structures were elucidated by interpretation of their IR, high resolution-mass spectrometry (HR-MS), 1D-and 2D-NMR data. Fischerisin A and B are the first representatives of a novel sesquiterpenoid-geranylhydroquinone hybrid, and both compounds exhibited in vitro cytotoxicity against cultured human oral epidermoid carcinoma (KB) and human breast cancer (MCF-7) cell lines with IC 50 values of 9.7 and 10.2 m mM, and 9.8 and 17.8 m mM, respectively.

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“…The genus Aster (Compositae) is composed of approximately 250 species of plants. More than 20 Aster species in China have been used in traditional Chinese medicine for treating snake bites, fever, cold, tonsillitis, and pneumonia (Xie et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

“…A novel eudesmane-type sesquiterpene compound, 1-oxoeudesm-11(13)-eno-12,8a-lactone (OEL), was isolated from the Chinese herb Aster himalaicus in our previous report (Xie et al, 2010). In order to further understand its anticancer effect and mechanisms, OEL was administered to different cancer cell lines and its role in apoptosis induction was explored.…”

Section: Introductionmentioning

confidence: 99%

1-oxoeudesm-11(13)-ene-12,8α-lactone-induced apoptosis via ROS generation and mitochondria activation in MCF-7 cells

Cui¹,

Zhang²,

Liu³

et al. 2011

Arch. Pharm. Res.

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A novel eudesmane-type sesquiterpene compound, 1-oxoeudesm-11(13)-eno-12,8a-lactone (OEL), was isolated from Aster himalaicus. Its effect on apoptosis in human breast adenocarcinoma (MCF-7) cells was investigated. MTT assay showed that OEL substantially reduced the viability of KB, MCF-7, U87, A172, and MG-63 cells. MCF-7 cells were used to further evaluate the antitumor effects and anticancer mechanisms of OEL. OEL-induced apoptosis was characterized by chromatin condensation, formation of apoptotic bodies, and phosphatidylserine on extracellular surface; these effects were confirmed by DAPI nuclear staining and flow cytometry. Increased expression of Bax and deceased expression of Bcl-2 were also observed in OEL-treated MCF-7 cells. Moreover, OEL induced the loss of mitochondria membrane potential, release of cytochrome C, activation of caspase-9, and generation of reactive oxygen species. These findings indicate that reactive oxygen species generation and mitochondria activation were involved in apoptosis induced by OEL in MCF-7 cells. The results from our study demonstrated that OEL may be a promising pro-apoptotic compound that could be used to develop novel anticancer drugs.

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Eudesmane Sesquiterpenes and Other Constituents from Aster himalaicus

Cited by 12 publications

References 14 publications

1-Oxoeudesm-11(13)-eno-12,8a-lactone induces G2/M arrest and apoptosis of human glioblastoma cells in vitro

1-Oxoeudesm-11(13)-eno-12,8a-lactone induces G2/M arrest and apoptosis of human glioblastoma cells in vitro

Fischerisin A and B, Cytotoxic Sesquiterpenoid-Geranylhydroquinones from Ligularia fischeri

1-oxoeudesm-11(13)-ene-12,8α-lactone-induced apoptosis via ROS generation and mitochondria activation in MCF-7 cells

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