• Journal of Environmental Science International
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• v.26 no.11
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• pp.1285-1295
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• 2017

Chrysanthemum boreale Makino is widely distributed in Korea, China, Japan and Southeast Asian countries. C. boreale is one of the herbs used for treating various inflammatory diseases in oriental medicine. The present study was conducted to identify biologically active compounds from the leaves and stems of C. boreale. We isolated two sesquiterpene sactones from the leaves and stems of C. boreale using silica gel column chromatography and recyclic high perfomance liquid chromatography. The lactones were characterized by their spectroscopic data (NMR, IR, MASS). These compounds were subjected to Farnesyl Protein Transferase (FPTase) inhibition, Nitric Oxide (NO) release inhibition and apoptosis inhibition. The structur of the following isolated compound were elucidated 8,10-${\small{O}$-Acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 4,10-dihydroxy-8-${\small{O}$-Acetyl-2,11(13)-guaiadiene-12,6-olide. In the NO release inhibition assay, compound 2 showed strong activities, with an $IC_{50}$ value of $7{\mu}g/mL$, whereas compound 1 did not exhibit significant activity with an $IC_{50}$ value of over $14{\mu}g/mL$ against murine macrophage.

• Korean Journal of Pharmacognosy
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• v.41 no.2
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• pp.103-107
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• 2010

Extensive phytochemical investigation of the methanol extract from the whole plant of Youngia japonica (Asteraceae) led us to the isolation of a new guaiane-type sesquiterpene (1), together with three related guaianolides, youngiajaponicoside A (2), crepiside H (3) and crepeside E (4). The chemical structure of 1 was elucidated by the aid of spectroscopic analyses including 2D-NMR experiments (COSY, HMBC, HMQC and ROESY). The isolated components (1-4) were evaluated for the inhibitory effect on the proliferation of four cultured human tumor cell lines such as A549, SK-OV-3, SK-MEL-2 and HCT-15, in vitro.

• Natural Product Sciences
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• v.23 no.2
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• pp.92-96
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• 2017

A sesquiterpene was purified from Artemisia iwayomogi methanolic extract during the course of searching anti-inflammatory principle from medicinal plants. A sesquiterpene identified as armefolin inhibited the production of nitric oxide (NO) and attenuated inducible nitric oxide synthase (iNOS) protein level in lipopolysaccharide (LPS)-activated RAW 264.7 cells. Armefolin also down-regulated mRNA expressions of iNOS and pro-inflammatory cytokines, interleukin-$1{\beta}$ and interleukin-6 in LPS-activated macrophages. Moreover, armefolin suppressed the degradation of inhibitory-${\kappa}B{\alpha}$ (I-${\kappa}B{\alpha}$) in LPS-activated macrophages. These data suggest that armefolin from A. iwayomogi can suppress the LPS-induced production of NO and the expression of iNOS gene through inhibiting the degradation of I-${\kappa}B{\alpha}$. Taken together, armefolin from A. iwayomogi might be a candidate as promising anti-inflammatory agent.

• Natural Product Sciences
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• v.14 no.1
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• pp.51-55
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• 2008

Three sesquiterpene-lignans, eudeshonokiol B (1), eudesobovatol B (2), and clovanemagnolol (3), were isolated from the stem bark of Magnolia obovata, together with magnolol (4), honokiol (5), and obovatol (6) on the basis of spectroscopic and physicochemical analyses including 2D NMR and Mass. Compounds 1 - 3 were belongs to a unique class of natural products made up of a sesquiterpene and biphenyl-type neolignan via an ether bond. All the isolated compounds were tested in vitro for their cytotoxic activity against the HeLa, A549, and HCTll6 cancer cell lines. Compounds 1 - 6 showed the cytotoxic activity against tested cancer cell lines, with $IC_{50}$ values ranging from 7.1 to 14.4 ${\mu}g/mL$.

• Archives of Pharmacal Research
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• v.27 no.6
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• pp.619-623
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• 2004

Tissue factor (TF, tissue thromboplastin) is a membrane bound glycoprotein, which acceler-ates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor for activated factor VII (Vila). The TF-factor Vila complex (TF/VIIa) proteolytically activates factors IX and X, which leads to the generation of thrombin and fibrin clots. In order to isolate TF inhibitors, by means of a bioassay-directed chromatographic separation technique, from the leaves of Eriobotrya japonica Lindley (Rosaceae), a known sesquiterpene glycoside (2) and ferulic acid (3) were isolated as inhibitors that were evaluated using a single-clotting assay method for determining TF activity. Another sesquiterpene glycoside (1) was also isolated but was inactive in the assay system. Compound 3 was yielded by alkaline hydrolysis of compound 2. The structures of compounds 1, 2, and 3 were identified by means of spectral analysis as $3-O-{\alph}-L-rhamnopyranosyl-(1{\rightarrow}4)-a-L-rhamnopyranosyl-(1{\rightarrow}2)-[{\alph}-L-rhamnopyrano-syl-(1{\rightarrow}6)]-{\beta}-D-glucopyranosyl nerolidol$ (1), $3-O-{\alph}-L-rhamnopyranosyl-(1{\rightarrow}4)-{\alph}-L-rhamnopyr-anosyl-(1{\rightarrow}2)-[{\alph}-L-(4-trans-feruloyl)-rhamnopyranosyl-(1{\rightarrow}6)]-{\beta}-D-glucopyranosyl$ nerolidol (2) and ferulic acid (3), respectively. Compounds 2 and 3 inhibited 50% of the TF activity at con-centrations of 2 and $369{\;}\mu\textrm{m}/TF$ units, respectively.

• Korean Journal of Pharmacognosy
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• v.43 no.1
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• pp.6-9
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• 2012

The $CH_2Cl_2$ soluble part of the leaves of Helianthus tuberosus L. (Compositae) exhibited a potent cytotoxic activity against the cultured human tumor cell lines including A-549, SK-OV-3, SK-MEL-2, XF498 and HCT-15 in vitro. Bioassaydirected fractionation of the $CH_2Cl_2$ soluble part of this plant led to the isolation of four cytotoxic sesquiterpene lactones having ${\alpha}$-methylene-${\gamma}$-lactone ring in the molecule. On the basis of physical and spectral evidences, their structures were characterized as ${\Delta}^{4,15}$-isoatripliciolide tiglate (1), ${\Delta}^{4,15}$-isoatripliciolide methacrylate (2), budlein A isobutylate (3) and budlein A tiglate (4). The ${\Delta}^{4,15}$-isoatripliciolide tiglate (1) showed the most potent cytotoxic activity ($0.26{\mu}M<ED_{50}<2.16{\mu}M$) against all of the cell lines tested.

• Journal of the Korean Wood Science and Technology
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• v.44 no.2
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• pp.253-263
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• 2016

Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Ten additional species of white rot fungi were inoculated in medium containing nutrients such as $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ at $28^{\circ}C$ for 25 days. After 10 days of incubation, eudesmane-type sesquiterpenes, ${\beta}$-eudesmane and ${\beta}$-eudesmol, were only synthesized during the growth phase of P. brumalis. Experiments excluding one nutrient at a time were conducted to determine the effects of inorganic nutrients on sesquiterpene biosynthesis. In conclusion, GC-MS analysis showed that biosynthesis of sesquiterpenes was differentially regulated by inorganic nutrients such as $MgSO_4$, $C_4H_{12}N_2O_6$, and $KH_2PO_4$. We found $MgSO_4$ supplementation to be vital for eudesmane-type sesquiterpene biosynthesis in P. brumalis; nitrogen ($C_4H_{12}N_2O_6$) and phosphate ($KH_2PO_4$) inhibited the synthesis of P. brumalis metabolites. Magnesium is a known cofactor of sesquiterpene synthase, which promotes ${\beta}$-eudesmol synthesis. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

• Applied Biological Chemistry
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• v.42 no.2
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• pp.176-179
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• 1999

In the bioactivity test of nine sesquiterpene lactons isolated from Hemisteptia lyrata, Chrysanthemum zawadskii and Chrysanthemum boreale, we investigated their antimicrobial activities against ten bacteria and six phytopathogenic fungi. Hemistepsin A and hemistepsin B isolated from H. lyrata and tulipinolide isolated from C. boreale exhibited strong antibacterial activity. In the antifungal test, hemistepsin B, angeloylcumambrin B, tigloylcumambrin B and costunolide showed broad activity. Both antibacterial and antifungal experiments exhibited quite clear specificity against microbial strains.

• Archives of Pharmacal Research
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• v.23 no.1
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• pp.54-58
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• 2000

To elucidate the molecular mechanisms for the suppression of LPS-induced nitric oxide (NO) production by a dehydrocostus lactone (DL) from Saussurea lappa, we examined the preventive effect of this compound on $NF-{\kappa}B$ activation in LPS-treated RAW 264.7 macrophages and U937 human monocytic cells. The results suggest that the suppression of NO production is mediated by the inhibitory action on the i-NOS gene expression through the inactivation of $NF-{\kappa}B$ and this sesquiterpene lactone can act as a pharmacological inhibitor of the $NF-{\kappa}B$ activation.

• Archives of Pharmacal Research
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• v.26 no.7
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• pp.521-525
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• 2003

Phytochemical works on the aerial parts of Aster oharai (Compositae) led to the isolation of a new sesquiterpene hydroperoxide, 7$\alpha$-hydroperoxy-3, 11-eudesmadiene (2) and seven known compounds, teucdiol B (1), $\alpha$-spinasterol (3), oleanolic acid (4), $\alpha$-spinasterol 3-Ο-$\beta$-D-glucopyranoside (5), methyl 3,5-di-Ο-caffeoyl quinate (6), 3,5-di-Ο-caffeoylquinic acid (7), 3,4-di-Ο-caffeoylquinic acid (8). The chemical structures of 1-8 were established by chemical and spectroscopic methods. Compound 2 showed cytotoxicity against cultured human tumor cell lines in vitro, SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), and HCT15 (colon) with $ED_{50}$ values ranging from 3.86-17.21 $\mu$g/mL.