• Title/Summary/Keyword: labdane diterpene

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Isolation of Diterpene from Larix leptolepis Gorden (일본 잎갈나무재로부터 Diterpene의 단리)

  • Hwang, Byung-Ho;Zhao, Julan
    • Journal of the Korean Wood Science and Technology
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    • v.26 no.4
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    • pp.71-77
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    • 1998
  • To elucidate chemical structure of the wood extractive, wood meal of Larix leptolepis Gorden was extracted with 95% ethanol for 72 hours. The extract was fractionated with organic solvents such as n-hexane, chloroform, diethylether, and ethyl acetate. From the hexane somble fraction of the extractives, a new diterpene compound was isolated and identified as 6-acetoxymanool or 13-hydroxy-8(17), 14-labddienyl-6-acetate by IR, $^1H(^{13}C)$-NMR and Mass spectrometry.

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Bioassay-coupled LC-QTOF MS/MS to Characterize Constituents Inhibiting Nitric Oxide Production of Thuja orientalis

  • Park, Dawon;Shin, Hyeji;Byun, Youngjoo;Lee, Ki Yong
    • Natural Product Sciences
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    • v.27 no.4
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    • pp.293-299
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    • 2021
  • The ethyl acetate fractions prepared from the leaves of Thuja orientalis significantly inhibited nitric oxide (NO) production in lipopolysaccharide-stimulated BV2 microglial cells. According to bioassay-coupled LC-QTOF MS/MS, the components near 22 and 25 mins in the mass chromatogram highly inhibited NO production and were expected to be labdane diterpenes, and the active components were characterized via further isolation. The results of the NO production inhibitory assay of the isolated compounds correlated well with the results of bioassay-coupled LC-QTOF MS/MS. Among the identified constituents, NO production inhibitory activities of 16-hydroxy-labda-8(17),13-diene-15,19-dioic acid butenolide (2) and 15-hydroxypinusolidic acid (3) were newly reported. Taken together, these results demonstrated that LC-QTOF MS/MS coupled with NO production inhibition assay was a powerful tool for accurately predicting new anti-inflammatory constituents in the extracts from natural products. Moreover, it provided a potential basis for broadening the application of bioassay-coupled LC-QTOF MS/MS in natural product research.

Isolation and Structure Identification of Antibacterial Substances from the Rhizome of Zingiber mioga Roscoe (양하의 근경에서 항균성 물질 분리 및 구조동정)

  • Kim, Seong-Cheol;Song, Eun-Young;Kim, Kong-Ho;Kwon, Hyeog-Mo;Kang, Sang-Heon;Park, Ki-Hun;Jung, Yong-Hwan;Jang, Ki-Chang
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.246-250
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    • 2003
  • In order to isolate antibacterial substances from the rhizome of Zingiber mioga Roscoe, the ethanol extracts was fractionated according to the activity against Bacillus subtilis, B. cereus and Staphylococcus aureus. Three antibacterial substances were isolated and purified by column chromatography and recrystallization. Compounds I and III showed activity against all the tested bacterias and compound II exhibited the activity against B. subtilis and B. cereus S. aureus. Compound I was examined antimicrobial activity against B. subtilis, B. cereus and S. aureus by optical density using Bioscreen C. Compound I showed strong growth inhibition at 10 ppm on B. subtilis and B. cereus for 72 hrs, and at 25 ppm on S. aureus. On the basis of spectrometric studies including $1^H-NMR$, ${13}^C-NMR$, DEPT, IH-lH COSY, HMQC, HMBC and IR, compounds I, II and III were identified as $(E)-8{\beta}(17)-epoxylabd-12-ene-15,16-dial\;(C_{20}H_{30}O_3,\;MW=318)$, galanolactone $(C_{20}H_{30}O_3\;MW=318)$ and galanal A $(C_{20}H_{30}O_3,\;MW=318)$, respectively. These results are the first reports on the isolation of $(E)-8{\beta}(17)-epoxylabd-12-ene-15,16-dial, galanolactone and galanal A from the rhizome of Zingiber mioga.