Sesquiterpene compounds fromInula viscosa

Fontana, Gianfranco; Rocca, S. La; Passannanti, Salvatore; Paternostro, Mariapia

doi:10.1080/14786410701415681

Cited by 54 publications

(30 citation statements)

References 10 publications

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“…The β-orientation of the hydroxyl group at C-5 was assigned based on carbon shift data. 22 Therefore 3 was assigned to (2β,5β-dihydroxycadin-3-en-12-oic acid) (tanacetolide C).…”

Section: Resultsmentioning

confidence: 99%

Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum

et al. 2015

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New sesquiterpenes tanacetolide A-C (1-3) were isolated from a Tanacetum sinaicum extract together with known compounds (4-10). Structures were elucidated on the basis of MS and NMR spectroscopic data. All compounds were evaluated for the inhibition of inducible nitric oxide (NO) production in a mouse peritoneal macrophage system. Iso-secotanapartholide-3-O-methyl ether (4) produced potent inhibition of NO production (IC50 = 1.0 µM). At the protein expression level, 4 elicited concentration-dependant down-regulation of inducible nitric oxide synthase.

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“…The β-orientation of the hydroxyl group at C-5 was assigned based on carbon shift data. 22 Therefore 3 was assigned to (2β,5β-dihydroxycadin-3-en-12-oic acid) (tanacetolide C).…”

Section: Resultsmentioning

confidence: 99%

Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum

et al. 2015

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“…Therefore, S configuration on C-2 of 2 was suggested and all relevant chiral centers in 2 were assigned as 1S, 2S, 4S, 5S, 8S and 10R configurations. Structures of 3-14 were identified by comparison of 1 H-and C 13 -NMR, FAB-MS spectral data and optical rotation values with those previously reported to be budlein B (3), 23) 6β-hydroxytomentosin (4), 24) 6-deacetoxybritanin (5), 25) 4-epipulchellin (6), 26) britanin (7), 27) tomentosin (8), 28) (+)-dihydroquercetin (9), 29) (−)-syringaresinol (10), 30) quercetagetin 3,4′-dimethy ether (11), 31) luteolin (12), 32) britanin G (13) 33) and inuchinenolide C (14) 34) (see the Supplementary materials). These compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were tested for inhibitory activities of DNA topoisomerases I and II (Fig.…”

Section: Resultsmentioning

confidence: 99%

DNA Topoisomerase Inhibitory Activity of Constituents from the Flowers of Inula japonica

et al. 2016

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Key words Inula japonica; topoisomerase I; topoisomerase IIInula japonica THUNB. (Asteraceae) is a traditional herbal medicine and is widely distributed in Korea, Japan and China, and the flowers of this plant have been used to relieve phlegm, peptic disorder, inflammation and detumescence.1) Some terpenes 2-7) and flavonoids 8,9) have previously been isolated from this medicinal plant and have been reported to possess diverse biological activities, such as anti-diabetes, 10) antihypolipidemia, 11) hepatoprotective, 12) anti-inflammatory 7) and anti-tumor 1,2,13) effects. We have been isolating compounds that inhibited topoisomerases I and II from the source of medicinal plants. [14][15][16][17][18] DNA topoisomerases are enzymes that control DNA topology in the cell and are targets of anticancer drugs. 19,20) Topoisomerase I cleaves and reseals one DNA strand at a time and does not require ATP for the complementary strand to pass through the enzyme-linked strand break, thereby effecting DNA relaxation. Topoisomerase II cleaves both strands of DNA during catalysis. In a reaction coupled to ATP binding and hydrolysis, these proteins cleave one DNA duplex, transport a second duplex through the break, and then religate the cleaved duplex. 21) Camptothecin (CPT) and etoposide (VP-16) are typical inhibitors of topoisomerases I and II, respectively. 19) In this paper, we report isolation of fourteen compounds from the flowers of I. japonica and their DNA topoisomerases I and II inhibitory activities and cytotoxicities. Results and DiscussionTwo new (1, 2) and twelve known compounds (3-14) were isolated by various chromatographic separations from the EtOAc extract of the flowers of I. japonica (Fig. 1) C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra of 1 showed seventeen peaks due to three methyl, four methylene, five methine and five quaternary carbons. The corresponding proton signals were determined by 1 H-detected heteronuclear multiple quantum coherence (HMQC) spectrum.The

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“…[10][11][12][13][14] It has been shown to exhibit anti-fungal and anti-proliferative activities and to induce apoptosis in cancer cell lines. In this study, the ethanol extract of Inulae flos was partitioned with different solvents and the ethyl acetate fraction showed anti-inflammatory activities (data not shown).…”

Section: Resultsmentioning

confidence: 99%

Suppressive Effect of Tomentosin on the Production of Inflammatory Mediators in RAW264.7 Cells

Park

Kim

et al. 2014

Biological & Pharmaceutical Bulletin

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In this study, tomentosin, a sesquiterpene lactone was isolated from Inulae flos and its biological activities were investigated. The effects of tomentosin on the production of inflammatory mediators as well as on nuclear factor (NF)-κB and mitogen-activated protein (MAP) kinase activation were evaluated in RAW264.7 cells. Tomentosin decreased the production of nitric oxide (NO) and prostaglandin E 2 (PGE 2 ) by suppressing the protein expression of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2, respectively. Additionally, tomentosin reduced the release of pro-inflammatory cytokines, such as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6). Tomentosin not only attenuated lipopolysaccharide (LPS)-induced NF-κB activation via the abrogation of inhibitory (I)κBα degradation and caused a subsequent decrease in nuclear p65 level, but it also suppressed the phosphorylation of MAP kinases (p38 and c-Jun N terminal kinase (JNK)). These results indicate that tomentosin exerts anti-inflammatory activities through the inhibition of inflammatory mediators (NO, iNOS, PGE 2 , COX-2, TNF-α, and IL-6) by regulating NF-κB activation and phosphorylation of p38/JNK kinases in macrophages, thus suggesting that tomentosin could be a potential agent for the treatment of inflammatory diseases. Key words tomentosin; inflammatory mediator; nuclear factor (NF)-κB; mitogen-activated protein (MAP) kinaseInflammation is the host response to infection and injury, but if it is left uncontrolled, the inflammatory mediators become involved in the pathogenesis of many inflammatory disorders.1) Macrophages play a crucial role in both the specific and non-specific immune responses to microbial and viral infections. When activated by stimuli such as lipopolysaccharide (LPS), macrophages produce a variety of inflammatory mediators such as prostaglandin E 2 (PGE 2 ) and nitric oxide (NO) and pro-inflammatory cytokines including tumor necrosis factor-α (TNF-α), interleukin-1beta (IL-1β) and IL-6.Expression of these inflammatory mediators is regulated by the activation of nuclear factor-kappaB (NF-κB).2) Also, inflammatory mediators including cytokines or mitogenactivated protein (MAP) kinases such as p38 and c-Jun N terminal kinase (JNK) stimulate the pathways by activating the inhibitor κB kinase (IKK).3,4) In unstimulated cells, NF-κB is located in the cytoplasm as an inactive complex bound to its inhibitory protein (IκB). During the process of inflammation, the IKK phosphorylates IκB, inducing its ubiquitination and degradation of IκBα. The free NF-κB then translocates to the nucleus, where it binds to κB-binding sites in the promoter regions of target genes and regulates the expression of various genes, including inducible NO synthase (iNOS) and cyclooxygenase 2 (COX-2), and inflammatory cytokines. 5-7)Our previous studies have shown that the ethanol extract of Inulae flos is a potent inhibitor of inflammatory mediators. 8)Recently, it was shown that britanin isolated from Inulae flos inhibited the production of inflammatory medi...

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Sesquiterpene compounds fromInula viscosa

Cited by 54 publications

References 10 publications

Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum

Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum

DNA Topoisomerase Inhibitory Activity of Constituents from the Flowers of <i>Inula japonica</i>

Suppressive Effect of Tomentosin on the Production of Inflammatory Mediators in RAW264.7 Cells

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