• Title/Summary/Keyword: Sesquiterpene

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Microbial transformation of the sweet sesquiterpene (+)-hernandulcin

  • Yang, Hyun-Ju;Kim, Hyun-Jung;Whang, Yun-Ae;Choi, Jung-Kap;Lee, Ik-Soo
    • Natural Product Sciences
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    • v.5 no.3
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    • pp.151-153
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    • 1999
  • (+)-Hernandulcin is a sweet bisabolane-type sesquiterpene first isolated from Lippia dulcis Trev. (Verbenaceae). This oily compound is 1000-1500 times sweeter than sucrose but with poor solubility in water. Microbial transformation was employed to improve its water solubility, and a variety of microorganisms were screened for their ability to convert (+)-hernandulcin to more polar metabolites. Scale-up fermentation with Glomerella cinguiata, a fungal strain, has resulted in the isolation of a more polar metabolite (2).

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Isolation of Isoamberboin and Isolipidiol from Whole Plants of Youngia japonica (L.) DC. (뽀리뱅이 전초로부터 Isoamberboin과 Isolipidiol의 분리)

  • Jang, Dae-Sik;Ha, Tae-Joung;Choi, Sang-Uk;Nam, Sang-Hae;Park, Ki-Hun;Yang, Min-Suk
    • Korean Journal of Pharmacognosy
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    • v.31 no.3
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    • pp.306-309
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    • 2000
  • Two sesquiterpene lactones were isolated from methanol extracts of the whole plants of Youngia japonica (L.) DC. by the silica gel column chromatography and recrystallization. On the basis of spectrometric studies including $^1H-NMR,\;^{13}C-NMR,\;DEPT,\;^1H-^1H\;COSY,\;^{13}C-^1H\;COSY$, IR and MS, compounds 1 and 2 were identified as derivatives of 10(14)-guaien-12, 6-olide, isoamberboin and isolipidiol, respectively. This is the first report on the isolation of isoamberboin and isolipidiol from Youngia japonica (L.) DC.

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Antibiotic Components from the Rhizomes of Curcuma zedoaria

  • Jeong, Choon Sik;Shim, Sang Hee
    • Natural Product Sciences
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    • v.21 no.3
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    • pp.147-149
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    • 2015
  • Two terpenoids, including one uniquely aromatized one (1), were isolated from CH2Cl2-soluble fraction of MeOH extracts of Curcuma zedoaria. They were identified to be a sesquiterpene ketolactone (1) and orobanone (2), respectively on the basis of their NMR data. The structure of compound 1 was confirmed by X-ray chrystallography and the reported NMR assignments for 1 were revised in this study. Antibiotic activities for compounds 1 and 2 were evaluated using disk diffusion assay. Compound 1 showed potent antibacterial activities against Listeria monocytogenes and Staphylococcus pseudointermedius while compound 2 was active against Bacillus cereus.

Inhibitors of Nitric Oxide Production from Artemisia princeps

  • Li, Dayu;Han, Xiang Hua;Hong, Seong-Su;Lee, Chul;Lee, Moon-Soon;Lee, Dong-Ho;Lee, Mi-Kyeong;Hwang, Bang-Yeon
    • Natural Product Sciences
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    • v.16 no.3
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    • pp.143-147
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    • 2010
  • The chromatographic separation of a methanol extract of Artemisia princes led to the isolation of two sesquiterpene lactones, artecanin (1) and canin (2), together with a flavonoid, eupatilin (3). Their structures were determined by 1D, 2D-NMR and MS data analysis. All of the isolates were evaluated for their potential to inhibit the LPS-induced production of nitric oxide in murine macrophage RAW 264.7 cells. Compounds 1 - 3 inhibited nitric oxide production with $IC_{50}$ values of 19.5, 20.4 and 25.1 ${\mu}M$, respectively.

Cangorins F-J , Five Additional Oligo-Nicotinated Sesquiterpene Polyesters from Maytenus Ilicifolia

  • Hideji Itokawa;Osamu Shirota;Hiroshi Morita;Koichi Takeya;Yoichi Iitaka
    • Korean Journal of Plant Resources
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    • v.7 no.1
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    • pp.77-87
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    • 1994
  • The isolation and structure elucidation Of five new oligo-nicotinated sesquiterpene polyesters with a dihydroagarofuran core from Maytenus ilicifolia, named cangorins F, G,H,1 and J [1-5], is described. The strurtures of these compounds, which possessed nicotinyl,benroyl, and areryl groups as esterifying moieties, were elucidaied by $^IH- and ^{13}C$-nmrspectroscopic studies, inrlusive of hereronuclear correlation, long-range correlation, and nOespectra, along with mass and cd spectral dara, and the X-ray crystallographic analysis of 1.

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Phytochemical Constituents of Carpesium macrocephalum $F_R$. et $S_{AV}$.

  • Kim, Mi-Ran;Lee, Seung-Kyu;Kim, Chang-Soo;Kim, Kyung-Soon;Moon , Dong-Cheul
    • Archives of Pharmacal Research
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    • v.27 no.10
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    • pp.1029-1033
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    • 2004
  • From the methanol extract of the whole plants of Carpesium macrocephalum $F_R$. et $S_{AV}$., five sesquiterpene lactones (1: carabron, 2: tomentosin, 3: ivalin, 4: 4H-tomentosin, 5: carabrol) and three terpenoids (6: loliolide, 7: vomifoliol, 8: citrusin C) were isolated. The structures and stereochemistry of compounds 1-8 were established on the basis of chemical analysis as well as 1D- and 2D-NMR spectroscopy. Among them, compounds 2, 4, and 6-8 were isolated for the first time from Carpesium species.

In vitro Biological Activity of Germacranolide sesquiterpene lactones

  • Kim, Myung-Ju;Lee, Jae-Sug;Baek, Seung-Hwa
    • Advances in Traditional Medicine
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    • v.9 no.2
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    • pp.192-199
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    • 2009
  • Bioactivity-directed isolation has led to the isolation of (-)-ent-costunolide (1) as the major active compound from Hepatostolonophora paucistipula. This compound (1) was determined by spectroscopic data interpretation. This sesquiterpene lactone (1) inhibited the growth of the dermatophytic fungus Trichophyton mentagrophytes ATCC 28185, (4 mm inhibition zone at $15{\mu}g$/disc), cytotoxic activity to murine leukaemia cell lines ATCC CCL 46 P 388D1 ($IC_{50}$ 687 ng/ml, at $0.075{\mu}g$/disk), BSC monkey kidney cell lines (100% of well at $15{\mu}g$/disk) and antiviral activity to Herpes simplex virus (0.25 mg/ml, 100% of well at $7.5{\mu}g$/disk) and Polio virus (0.125 mg/ml, 100% of well at $3.75{\mu}g$/disk). These results suggest that (-)-ent-costunolide (1) has potential antimicrobial and cytotoxic agents.

Zerumbone, Sesquiterpene Photochemical from Ginger, Inhibits Angiogenesis

  • Park, Ju-Hyung;Park, Geun Mook;Kim, Jin-Kyung
    • The Korean Journal of Physiology and Pharmacology
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    • v.19 no.4
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    • pp.335-340
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    • 2015
  • Here, we investigated the role of zerumbone, a natural cyclic sesquiterpene of Zingiber zerumbet Smith, on angiogenesis using human umbilical vein endothelial cells (HUVECs). Zerumbone inhibited HUVECs proliferation, migration and tubule formation, as well as angiogenic activity by rat aorta explants. In particular, zerumbone inhibited phosphorylation of vascular endothelial growth factor receptor-2 and fibroblast growth factor receptor-1, which are key regulators of endothelial cell function and angiogenesis. In vivo matrigel plug assay in mice demonstrated significant decrease in vascularization and hemoglobin content in the plugs from zerumbone-treated mice, compared with control mice. Overall, these results suggest that zerumbone inhibits various attributes of angiogenesis, which might contribute to its reported antitumor effects.