Sesquiterpenoid Derivatives from Ferula ferulioides. V.

Kojima, Keisuke; Isaka, Kimio; Purev, Ondognii; Zevgeegiin, Oyun; Gombosurengyin, Purevsuren; Davgiin, Khishgee; Mizukami, Hajime; Ogihara, Yukio

doi:10.1248/cpb.49.1072

Cited by 33 publications

(33 citation statements)

References 9 publications

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“…The HMBC experiment suggested that the structure of 5 was similar to that of 4. 14) However, the NMR spectra of 5 differed slightly from those of 4, especially C-1Ј and 2-Me, indicating 5 may be a diastereomer of 4 at the chiral centers C-2 and C-3. The relative configuration of the dimethyldihydrofuran moiety at C-2 and C-3 was determined on the basis of the difference NOE experiments.…”

Section: Resultsmentioning

confidence: 95%

“…14) When the RAW 264.7 were incubated with LPS and IFNg, NO production increased sharply. These compounds showed inhibitory activities (1: IC 50 ϭ30.2Ϯ1.7 mM; 2: IC 50 ϭ29.0Ϯ1.0 mM; 3: IC 50 ϭ30.7Ϯ0.9 mM; 4: IC 50 ϭ27.8Ϯ 4.6 mM; 5: IC 50 ϭ27.3Ϯ2.3 mM; 6: IC 50 ϭ87.5Ϯ11.7 mM, nϭ3).…”

Section: Resultsmentioning

confidence: 99%

“…Compounds commonly found in this genus are sesquiterpenes [4][5][6][7][8][9][10] (especially daucanes, humulanes, and guaianes), sesquiterpene coumarins, and sesquiterpene chromones. [11][12][13][14][15] F. fukanensis has been used as a traditional medicine for treatment of rheumatoid arthritis and bronchitis. In our investigation of in vitro anti-inflammatory screening of medicinal herbal extracts, the 80% aqueous methanol extract of the roots of F. fukanensis was observed to inhibit nitric oxide (NO) production in a lipopolysaccharide (LPS) activated murine macrophage-like cell line.…”

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confidence: 99%

“…The cells were incubated at 37°C for approximately 8 h. Total RNA was isolated from the cell pellet using a RNA isolation kit (QIAGEN, Hilden, Germany). Total RNA (250 ng) was reverse-transcribed into cDNA by oligo(dT) [12][13][14][15][16][17][18] primer. The PCR sample contained 30 ml of the reaction mixture, comprised of 50 mM KCl, 5 mM MgCl 2 , 0.2 mM dNTP, 0.6 units of Ampli Taq GOLD (Applied Biosystems, CA, U.S.A), and 0.4 mmol of sense and antisense primers.…”

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confidence: 99%

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Sesquiterpene Coumarins from Ferula fukanensis and Nitric Oxide Production Inhibitory Effects (2)

Motai

Kitanaka

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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Four new sesquiterpene coumarin derivatives, fukanemarin B (1), fukanefuromarin E (2), fukanefuromarin F (3) and fukanefuromarin G (5) were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated based on spectral evidence, especially heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The 80% aqueous methanol extract of the roots of Ferula fukanensis (FFE) and the sesquiterpene coumarin derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-g g (IFN-g g).

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Sesquiterpene Coumarins from Ferula fukanensis and Nitric Oxide Production Inhibitory Effects (2)

Motai

Kitanaka

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Compounds commonly found in this genus are sesquiterpene coumarins and sesquiterpene chromones. [7][8][9][10][11][12][13] In our continuing investigations of the in vitro anti-inflammatory effects of medicinal herbal extracts, an 80% aqueous methanol (MeOH) extract of the roots of F. fukanensis (FFE) was observed to inhibit nitric oxide (NO) production in a lipopolysaccharide (LPS)-activated murine macrophagelike cell line. 2) Macrophages play major roles in immunity and the inflammatory responses involved with host defense.…”

mentioning

confidence: 99%

Sesquiterpene Coumarins from <i>Ferula fukanensis</i> and Their Pro-inflammatory Cytokine Gene Expression Inhibitory Effects

Motai

Daikonya

Kitanaka

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Six new sesquiterpene coumarin derivatives, fukanefuromarin H-M (1-6), were isolated from an 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectroscopic evidence, particularly heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The sesquiterpene coumarin derivatives inhibited nitric oxide (NO) and inducible NO synthase (iNOS), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) gene expression in a murine macrophage-like cell line (RAW264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-γ (IFN-γ).

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Chloroform Extract of Underground Parts of Ferula heuffelii: Secondary Metabolites and Spasmolytic Activity

Pavlović

Krunić

Nikolić

et al. 2014

Chemistry & Biodiversity

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Plants from the genus Ferula L. (Apiaceae) were used for various purposes in traditional medicine of different nations throughout the history. Ferula heuffelii Griseb. ex Heuffel is a perennial species endemic for Balkan peninsula. Ten compounds which belong to classes of prenyl-furocoumarin-, prenyl-dihydrofurochromone-, prenyl-benzoyl- and prenyl-benzoylfuranone-type sesquiterpenoids, as well as sesquiterpene coumarins and phenylpropanoids, were, for the first time, isolated from the CHCl3 extract of the underground parts of this plant and identified. Furthermore, extract and three isolated compounds, i.e., latifolone (1), dshamirone (4), and (2S*,3R*)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2,3-dihydro-7-hydroxy-2,3-dimethylfuro[3,2-c]coumarin (6) were, for the first time, evaluated for their in vitro antispasmodic activities in three experimental models: spontaneous contraction, and ACh- and KCl-induced contraction of an isolated rat ileum. The extract (0.1-1.3 mg/ml) and compound 6 (1-10 μg/ml) exhibited dose-dependent effect in all three models. Compound 1 (1-6 μg/ml) affected spontaneous contractions and those induced by KCl, while compound 4 (8 μg/ml) displayed only moderate activity with ACh-induced contractions. It can be concluded that tested compounds contribute to exhibited antispasmodic activity of crude extract. Additionally, extract (0.1-1.3 mg/ml) was tested for in vitro relaxant activity on an isolated rat trachea, and relaxed the KCl-induced contractions in a dose-dependent manner.

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Sesquiterpenoid Derivatives from Ferula ferulioides. V.

Cited by 33 publications

References 9 publications

Sesquiterpene Coumarins from Ferula fukanensis and Nitric Oxide Production Inhibitory Effects (2)

Sesquiterpene Coumarins from Ferula fukanensis and Nitric Oxide Production Inhibitory Effects (2)

Sesquiterpene Coumarins from <i>Ferula fukanensis</i> and Their Pro-inflammatory Cytokine Gene Expression Inhibitory Effects

Chloroform Extract of Underground Parts of Ferula heuffelii: Secondary Metabolites and Spasmolytic Activity

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