• 제목/요약/키워드: cytotoxic sesquiterpenes

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Isolation of Cytotoxic Compounds from the Leaves of Xanthium strumarium L.

  • Ahn, Jong-Woong;No, Zae-Sung;Ryu, Shi-Yong;Zee, Ok-Pyo;Kim, Seong-Kie
    • Natural Product Sciences
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    • 제1권1호
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    • pp.1-4
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    • 1995
  • MeOH extract of the leaves of Xanthium strumarium L. were found to have cytotoxic activities against five human tumor cell lines. Cytotoxicity-guided chromatographic fractionation led to the isolation of the ${\alpha}-methylene$ containing sesquiterpenes, xanthatin, 8-epi-xanthatin and 8-epi-tomentosin. 8-epi-Xanthatin was found to be far more cytotoxic than 8-epi-tomentosin, which lacks the conjugated enone moiety present in 8-epi-xanthatin.

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Cytotoxic Activities of Brominated Sesquiterpenes from the Red Alga Laurencia okamurae

  • Ryu, Geon-Seek;Park, Soo-Hee;Choi, Byoung-Wook;Lee, Nam-Ho;Hwang, Hye-Jung;Ryu, Shi-Yong;Lee, Bong-Ho
    • Natural Product Sciences
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    • 제8권3호
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    • pp.103-107
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    • 2002
  • Four known sesquiterpenes, laurinterol (1), isolaurinterol (2), aplysinal (3) and aplysin (4) were isolated from the Korean red alga Laurencia okamurae off Cheju Island, Korea. Their structures were identified by comparison with the literature data. Compounds 1-4 showed potent cytotoxicity against A549, SK-OV-3, SKMEL-2, XF498, and HTl5 cell lines with $EC_{50}$ values ranging from 1.2 to 17.6 ${\mu}g/ml$.

Cytotoxic Compounds from the Stem Bark of Magnolia obovata

  • Min, Byung-Sun;Youn, Ui-Joung;Bae, Ki-Hwan
    • Natural Product Sciences
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    • 제14권2호
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    • pp.90-94
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    • 2008
  • Two sesquiterpenes (1 - 2), a tetralone (3), and two phenylpropanoids (4 - 5) were isolated from the stem bark of Magnolia obovata Thunberg (Magnoliaceae) through repeated column chromatography. Their structures were identified as ${\beta}-eudesmol$ (1), cryptomeridiol (2), 4R-4,8-dihydroxy-${\beta}-tetralone$ (3), trans-pcoumaryl aldehyde (4), and p-coumaric acid (5) on the basis of spectroscopic analysis including two dimensional NMR and mass. Compounds 1 - 3 were tested in vitro for their cytotoxic activity against the K562, HeLa, A549, and HCT116 cancer cell lines. However, compounds 1 - 3 were inactive in this assay system.

Biological Characterization of the Chemical Structures of Naturally Occurring Substances with Cytotoxicity

  • Park, Hee-Juhn;Jung, Hyun-Ju;Lee, Kyung-Tae;Choi, Jong-Won
    • Natural Product Sciences
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    • 제12권4호
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    • pp.175-192
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    • 2006
  • Screening for the cytotoxicity from plant origin is the first stage for anti-cancer drug development. A variety of terpenoids with exomethylene, epoxide, allyl, $\alpha,\beta-unsaturated$ carbonyl, acetylenes, and $\alpha-methylene-\gamma-lactone$ induces apoptosis and/or differentiation as well as cytotoxicity through the ROS signal transduction pathways. These are found among monoterpenes, sesquiterpenes, triterpenes, flavonoids, coumarins, diarylheptanoids, and even organosulfuric compounds. The most essential characteristics of natural cytotoxic substances is to possess the strong electrophilicity that is susceptible to nucleophilic biomolecules in the cell. Thiol-reductants and superoxide dismutase can block or delay apoptosis. Thus, ROS and the resulting cellular redox-potential changes can be parts of the signal transduction pathway during apoptosis. Disturbance of the balance of oxireduction by the pigment of natural quinones also caused the induction of the differentiation and apoptosis. Saponins with the cytotoxicity are restricted to their monodesmosides, rather than to bisdesmosides. Those saponins exhibited calcium ion-mediated apoptosis in addition to cytotoxicity whereas they showed also differentiation without extracellular calcium ion. The properties on cytotoxicity, apoptosis, and differentiation were assumed to depend on resultant oxidative stress to the cells. In this review, we describe a spectrum of cytotoxic compounds with various action mechanisms.

Cytotoxic and ACAT-inhibitory Sesquiterpene Lactones from the Root of Ixeris dentata forma albiflora

  • Ahn, Eun-Mi;Bang, Myun-Ho;Song, Myoung-Chong;Park, Mi-Hyun;Kim, Hwa-Young;Kwon, Byoung-Mog;Baek, Nam-In
    • Archives of Pharmacal Research
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    • 제29권11호
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    • pp.937-941
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    • 2006
  • Ixeris dentata forma albiflora was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$. Eight sesquiterpenes were isolated through repeated silica gel and octadecyl silica gel ($C_{18},\;ODS$) column chromatography of the EtOAc and n-BuOH fractions. Physicochemical analysis using NMR, MS and IR revealed the chemical structures of the sesquiterpenes, which were zaluzanin (1), 9a-hydroxyguaian-4(15), 10(14), 11 (13)-triene-6, 12-olide(2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguaian$-4(15), 10(14)-diene-6, 12-olide (3), $3-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguauan$-10(14)-ene-6, 12-olide (4), ixerin M (5), glucozaluzanin C (6), crepiside I (7), and ixerin D (8). This is the first time that these sesquiterpene lactones have been isolated from this plant. Compounds 1, 2 and 7 revealed relatively high cytotoxicities on human colon carcinoma cell and lung adeno-carcinoma cell, while compounds 5 and 7 showed acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory activity.

Evaluation of Antioxidant and Anticancer Activity of Steam Extract from The Bamboo Species

  • Kim, Ji-Su;Lee, Hyung Chul;Jo, Jong-Soo;Jung, Ji Young;Ha, Yeong Lea;Yang, Jae-Kyung
    • Journal of the Korean Wood Science and Technology
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    • 제42권5호
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    • pp.543-554
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    • 2014
  • Natural plant extract has been the subject of intense research aiming in elucidating the underlying mechanisms of their chemopreventive effects upon various forms of human cancers. The objective of our study was to evaluate the natural antioxidants and anticancer agent potential of Phyllostachys. The chemical composition of steam extract from Phyllostachys was carried out using GC-MS. The steam extract of Phyllostachys was dominated by monoterpenes (62.96% - 71.36%) and sesquiterpenes (23.58% - 33.13%) as the main compounds. The antioxidant activities of the steam extract was determined using a DPPH scavenging and hydrogen peroxide scavenging activity test systems. Furthermore, the amounts of total phenolics in steam extract were determined spectrometrically The steam extract of P. pubescens and P. bambusoides were presented the high activity (69.4% and 64.0%, respectively.). The steam extract from Pyllostachys species showed a hydrogen peroxide scavenging activity of approximately 50.4% - 54.6% when compared to that of the standard gallic acid. The anticancer activities of steam extract were determined using a MTT assay. Assessment of the cytotoxic effect of the steam extract on PC-3 cells showed that the P. bambusoides (20.85%) and P. pubescens (20.41%) were superior in induced cytotoxicity compared with the steam extract of P. nigra var. henonis (1.15%). Findings from this study indicated that steam extract of P. bambusoides and P. pubescens possessed potential as medicinal drug especially in prostate cancer treatment.