Purification, characterization, crystal structure and NO production inhibitory activity of three new sesquiterpenoids from homalomena occulta
Two new isodaucane-type sesquiterpenoids, namely (1R,4S,5S,6R,7S,10R)-isodauc-6,7,10-triol, C15H28O3, (1), and (1R,4S,5S,6S,7S,10R)-isodauc-6,7,10-triol, (2), and a new eudesmane-type sesquiterpenoid, 1β,4β,5α-trihydroxyeudesmane, (3), were obtained from the rhizomes of homalomena occulta with the aid of column chromatography. Their structures were elucidated based on extensive spectroscopic analyses, including 1D NMR, 2D NMR and HRESIMS. The structure of (1) was confirmed by single-crystal X-ray diffraction and the absolute configuration was assigned with respect to that of the precursor. The single-crystal structure reveals that adjacent molecules of (1) embrace through two groups of intermolecular O-H...O hydrogen bonds to generate a two-dimensional sheet with a 63-net topology. The three compounds were evaluated for their activity against lipopolysaccharide-induced production of nitrogen oxide (NO) in RAW 264.7 cells, and (1) showed an inhibitory effect on NO production, with IC50 values of 5.7±0.22 µM.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2018 |
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| Erschienen: |
2018 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:74 |
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| Enthalten in: |
Acta crystallographica. Section C, Structural chemistry - 74(2018), Pt 11 vom: 01. Nov., Seite 1440-1446 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Qi [VerfasserIn] |
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| Links: |
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| Themen: |
Crystal structure |
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| Anmerkungen: |
Date Completed 21.11.2018 Date Revised 21.11.2018 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1107/S2053229618013815 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM290314402 |
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| 245 | 1 | 0 | |a Purification, characterization, crystal structure and NO production inhibitory activity of three new sesquiterpenoids from homalomena occulta |
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| 500 | |a Date Revised 21.11.2018 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Two new isodaucane-type sesquiterpenoids, namely (1R,4S,5S,6R,7S,10R)-isodauc-6,7,10-triol, C15H28O3, (1), and (1R,4S,5S,6S,7S,10R)-isodauc-6,7,10-triol, (2), and a new eudesmane-type sesquiterpenoid, 1β,4β,5α-trihydroxyeudesmane, (3), were obtained from the rhizomes of homalomena occulta with the aid of column chromatography. Their structures were elucidated based on extensive spectroscopic analyses, including 1D NMR, 2D NMR and HRESIMS. The structure of (1) was confirmed by single-crystal X-ray diffraction and the absolute configuration was assigned with respect to that of the precursor. The single-crystal structure reveals that adjacent molecules of (1) embrace through two groups of intermolecular O-H...O hydrogen bonds to generate a two-dimensional sheet with a 63-net topology. The three compounds were evaluated for their activity against lipopolysaccharide-induced production of nitrogen oxide (NO) in RAW 264.7 cells, and (1) showed an inhibitory effect on NO production, with IC50 values of 5.7±0.22 µM | ||
| 650 | 4 | |a Journal Article | |
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| 650 | 4 | |a NO production inhibition | |
| 650 | 4 | |a crystal structure | |
| 650 | 4 | |a eudesmane | |
| 650 | 4 | |a isodaucane | |
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| 700 | 1 | |a Ma, Li |e verfasserin |4 aut | |
| 700 | 1 | |a Qu, Zhaoxia |e verfasserin |4 aut | |
| 700 | 1 | |a Hou, Guige |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Yanan |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Chunhua |e verfasserin |4 aut | |
| 700 | 1 | |a Zhao, Feng |e verfasserin |4 aut | |
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